SCIENTIFIC ABSTRACT ZAVGORODNIY, N.S. - ZAVGORODNIY, S.V.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001964010010-9
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: March 15, 2001
• Sequence Number: 10
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

- ------------
Termographic characteristics of marls--fr-o-d-the-7Awroolye-fka deposits,
-ka d site
RA0
TSement 96 no.4;0-10 ji-Agf ,6o. (ulak ifal
(Karl)

-SIDOCHENK.O., I.M.; ZAVGORODNIYI N.S.
Producing H70011,and "Soon types of portland cement. roement 27
no.3:19-20 My-Je 161. (MIRA 14:7)
(Pnrtland cement)

ZAVWRODIIIXP V.S,) inall.1 SIDOORKROp I.M.p inisho
Production of high.-otrongth cement at the Awrooleyka cement
acmbine# Much. soob. RIITSemonta no,'l2s24..27 161. (141RA 15:7)
1. Amvroaiyovokiy tsomentwly kombinat,
(Awrosiovka-Camont)

SIDOCHEUKOJV I.M., inzh.; ZAVGORODNI.Y, H.S., Who; ROSIA N.A., inzho
-system of open-pit minin of vol%l# mrl. Gorabur. no.5:20-22 11
161. (MIRA 14:6)
1. Amvrosiyevskiy-tsementnyy.kombinat,-Amvrosiyevka,,_Stalinskoy
oblasti.
(Strip mining-Cold weathe conditions) arl)

ZAVGORMNIY, N .9 MHEDLOV-IIETIIOSYAII O.P.; SIDOCHFNKO,,- I.M.;
STRELKOVA,, I.S.
Determination of slags and gypsum in cements by the thermographic
method. TSement 28 no.2:13--15 ~~-Ap 162. WIRA 15:8)
(cement)

SIDOCIIENKO, I.Mo-, -ZAVOOftODNIY, N.S.; REYGAUZ FIll Lo-v#-
Some defects in design. TSement 27 no.4:13-14 JI-Ag 61.
(MIRA 14- 8)

SIDOGRENKO, I.M., 1!.S., lnzh.; 14ASHKOVICH, M,L, inzh.;
PZYITGAUZEU, L.V., inzh.; Frf-JKIII, V.D., lnzh.; SHTEY124AN, Ye.Ye.,
lnzh,
Introduce the system of the automatic control of clinker firing.
TSoment 30 no. 2:15-17 Mr-Ap 164. .(MIRA 17:5)
1. Amvrosiyevskiy tsomentny-y kombinat i LSPNIJ tresta "Sevzapmon-
tazhavtomatika".

'it 16
O"JO MOM,
;Z,AVVwaLw!
0 A
o* 4
WID MTHOD Nit THIC PlWai=Ag OF STAND,VW SUUMAJ GF, Pk"4-
00 J11i ANGANAU. S.F. z& I. Zxvodakaya laboratoriya, 1949,
0,o a , ~ , 11 YAM -
"it 25, 363-3MMe ~In Rmsim). The stabilizqtion of
pp
eo solutions of potassium permanganate of strength 0.1-0.05N in lose
.. I
thxh 3 hr.* with kaolin Is described,-S.X.
T
muwt
mm
WWI .1
0-
0
-.5 04, 111 A 441411 Lw W All
to tr-4-4---j , y-, ~~, 1,
a to 0 of 4 A N ~.1 a If 0 MM I
o 0 41 0 Is 0 a a0 0 0 * 0 0 0 0 0 0 0 0
410 1: 0-0 0 0 0 0 0 0-0-010 0 0 CO-4 -0- 0 ; -4 o 00 0 wo 4 o o 0 o 0 o 0 *
Vo
v0
.
too
too

ZAV60RODR, S. F.
15. use la th. of
Anjov-tical Abet. S 17:g~
Ir k-liV04), deter-
minatiork d manialiate by hydroly-is to' W(nOj by
,Tan. 1,954 rm,111% of Cop 1(l SO, tic., 4.4,03 low results ex t
---&-anu ral
_h"hQ I'loV ou ffUf%;",V.
8, SMITH

GALKILAp,Ye.l.;-ZAVGORCMIlYp-S.Fe
Use of sodium tripolyphosphate for determining the calcium and
magnesium content in river and mineral waters* Iab.delo 7
no.1106-38 11 161. (MIRA 3-4:10)
1. Yafedra neorganichoskoy i analitichookoy khimii Rostovokogo-
na-Donu meditsinakogo instituta.
(SODnM TRIPIESPHATES) (WATER- -XIALYSIS)

GAIXINA, Ye.l.; ZAVGOHOPNIYO S.F.
Determinatton of calcium and winezium in the blocd eer--=
using ocdium t-ripolyphosphate. Vcp. md. khim. 9 ro.2t20?-209
14r-Ap 163. (MIRA 17.8)
1, Kafedra noorganicheckpy i aiaUticheakoy khimli Rostovskceo-
na-Donu meditsinskogo inotituta.

A ACC=Iaf- im: AP033426 Z/0055/64/OV;/OCV;/0271/0274
AUMCIR: Zav~tqva# N.
TITIB: The refractive index of Cd5b in the noigbborhoca of the absorption oaga
SaMCE: cholhoslovataldy fixicheski zhurnal, v. 14, no. 4, 1964, 271-274
ly
TOPIC TAGS: cadmium antimmide, rof'rective index,, absorption edge,, priam,
frequency dependence
ABSMCT Fig. I of the Bnclosure -si= zes,tho results of an experiment in
which trze priom method was exploited to measure the refractive index of cadniun
catimonido at r8m tempc~aturo in the region of the.absorption eko (2.3 to 3.1.V)4
Tile-indox-v=-daterminc4-th~ough measurement of the angle 8 by wbich a be= of
parallel rays ~= deflected froa~ 1~ts
the prism and through calculatioa according to Snell's law
sin((X +
sin a
Card 1/4

~C=S:10,1 IM: AP4033426
where a is the ariale or rersation cc the prism. 7aree prisms, each of whose
3~efractive edges were parallel to ciao of the crystallographic axes, were' ut
fr= the same p-type,CdSb monocrystal (Impurity concentratiom n x !Z~% =73)
ana then ground and optically polished. A surface' of 10 x 8 mm was irradiated,
vith a :* 10 deg# The radiatioa source was a Nernst filament chopped with a
frequency of 200 cyz. The detecting equilreftt, attached to the moving ~xm of
a Zeiss SGO 1o1 gonicmeter, conzistea of a Glan-Maapsoa polarizer an& an UP
lens. The PbS cell, located belov the diaphragm slit into which the lens focused
the beam, was connected to an amplifier with a synchronous detector. Mie anzle
vaz reaa by a microscope froa the sectione& circle of the gonlometer. The
-s~- -ma~xift-=--obaerved--near-the-absorpti-on edge for all tbree axes haxmonizes
e -the-measured.-values 0- -of-reflectica-R-vas--
-From -th6
calcit!~Lied` accordizig to. e',z4jatjorwbIp----,
1)2
R
+ 1P
rd

ACCESSION M: AP4033426
7ne valuos of R ford the a, b,. and a axe-3 at-0 va-400 to 50 - ev. range 'between
This is in good agroament-with the "luo of 42~ founiL in two
wit
aviouo Papara ed loyin -a-different methol U -
yr by tha author P IT an error. of +VA.,
it dooo n" adroavith the veluo of 2i-07 (n - 2.7) found by F. EmaxUa and
E. Mller (J. ra-chem. Soo. io8.. i9k io48),-but the disereMay is explAined,
by the effect of ourface Jzyors pmsent aa the s=ples employe& in that previous
study.-Nalues for..the dielectric constant gver the same eneri;y range varied frca
20-22 to 23-51-
ASSCSICATIM: Institute of Solid State Acad. Sei*, Prague
SUBI-EETIED: 190at63 DATE ACQ: 92YayO~ MICL: Ol
SUB CCDE: GIP NO M7 SOV: 000 Onm: 008
Card 3/4
7
77 77, 7 -
1~ 4"zzR 'UMPOMYST ;fITT"T,

ACCESSION NR: AP4033426
ENCLOSUREs
L
0 ig
lit
Card 4/4'
-41
""A 'i

UZYMOV, Vladimir Vasillyevich, inzh.1 BOLYAYEV, Ivan Favlovich, kand.-
tekhn.nauk, dotsent- NAZIKYAN, Artem Georgiyevich,, kand.tekhn.nauk;
Simultaneous use of analog, and digital computers in studying processes
in electrical machin6so Izve vyso ucheb, zav.; elektromekh. 6 no.l:
13,24 163, (MIRA 16:5).
1 Nachallnik laboratorii elektronnykh jchislitel'nykh mashin Novo-
charkaoskogo nauchno-issledovatel'skogo inatituta elektrovozootroyeaiya
(for Kleymnov). 2. Kafedra alektriebeskikh maohino apparatov,
matematidheakikh i Behetnoreahayushchikh priborov L ustroystv
Novocherkasqkogo politekhnicheskogo inatituts, (for Bolyakev, Nazikyan).
3. Starshiy inzhener laboratorii vychislitelf kh mashin Novochet-
kanskogo politekhnicheskogo instituta (for Zazzen).
(Eleotri"C machirerg)
(Electric machinery.:-Electromechanical arAlogies)

ZAWOROUMp P.Ye. LEBEWS L.V. (Lmingrad,, Botkinskaya ulop do 21o
~"107i
Plastioaurgery o? the axillary artery using a lavean prosthania,o
Test. khirs, 91 no.7e72-73 JV63' (MIRA l6zl2l)
1. Tz fakulltatskoy khirurgicheskoy klInIki (naebaltnik - profs
VSH,Sitenk) Voyennoo-meditsinakoy ordena lenina akademii imeni
S.MAirova.

GALUSHKOO V.P.; ZAVVsMUDNYA je F.; RODAKO YUOPO
Cathodic reduction of some sparingly soluble cobalt compounds.'
Zhur. prikl. khim* 36 no.-10:2349-2351 0 165. (MIRA M12)
1. Dnepropetrovskiy gosudarstvonnyy univermitet imeni 300-letiya
vosooyedinaniya Ukrainy s Roaaiyey, Submitted Nov. 12,, 1963.

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Im4yawrizittg eftert of Go akfiN and thus intertem
with *tha adda. r""im. The mte of the coa4ensation
I reactifort of Okfins wkk 0 tertiary C atom with WWS in the
0 Premixt of I is d"wd an semnt of The pdymerizins
a&-tka of I on shese-okli:ts, Tba followitiS nttfs weiv
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ACC NRo Apw=16 SOME CWZ: UW0286/65.70-700102 0101 101
AUT110hSt Isidorovp Vo Vol Akunovp Ve L Dubinskiy, M. G#j Z4vadskiz G. ve;
lonnakov, Y-u. T..j Lurlye, ti, YU or, ti, U. 1.,- Nonanko, _N._Y~.j Plavako, A. U.1
V. it., Sid -ffa 5 S.1 Titov, F. P. Khalev, -UDG--
shchovoll, A. S.; Zavgor,o,dn y No So
ORGg none
TITLE: A reactor for combined pulverizing and burning of a material,, such an cement#
in a high temperature ran stream. Glass eO, No. 11A69
SOURM Byulleten' izobrateniy i tovarnykh znakov, no. 22, 1965j, 101
TOPIC TAM cement, thurmal reactor
ABSTRAM This Author Certificate presents a reactor for combined pulverizing and
burning of a material, such aa comont, in a KiGh tovj)oraturo gas stream. To provide
automatic regulation of the burning and calcification tim for the material in the
reactor# the latter in made in the shape of a flatp lonticular dhambers Hozzlen
of the combustion chambers are built into the piripheral circle of the lentioular
chamber and at an angle to ita radii, An opening in the center of the chamber bottom
is used to discharge the finished burned producto
80 CODEs SUBM DATZI 24MAy6l

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noron f luoride nit a ca" in oremlc elluintry. IV, Cordonsation oLL,'_ianoj --lui
J. an, Chomo.)k (TJSSR)~ Vol. 16p I" -., pp. !495 1504
.45
C he., iAbs., Vol. 41o p. 5477-C
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I14ST OF 01MAX C10,11STRY, AGAD 5`01 USSH
ZAVGOWDN1Y, 5. V. - "Investigation in the Field of ReactJonz of U-n-
saturated Compounds In the Prosorice of- a lbron Fluorido Catalymt.
Sub 25 Nov 52p Inst of Organic Cherdstry, Acad Sci U,'SR. (Dissertation
for the Degree of Doctorates in Chemical Sciences).
-SO: Vechernana Moskva Janrary4ccember 1952

IY A .1 . v
-S. V., TOM EV., V. and PAM XIN YA
"Pronent Trands In Using Boror. Flwride In Catalytic Trnwiforration of
Hydro carbons," Usp. Ithim,., 213 No-4s 195"

ZOG010MI11 so Ve
"Interaction of ethyl etherate of boron fluoride with organic carboxylic
acids and with phenol." (p. 1781)
0% 'roijrnnl of CAnnra (Zhurnal Obshchei Kbimii) 22
S
-1 Ch ry

icides
SSR/Chem stry - Germ' Nov 52
Insecticides
~Catalyst in Organic' Chemis-
loron Fluoride a,~, a
try: VI. The Reacti 1 of o-Chloro Phenol With
on
CYclohexene," S. V~ Zavgorodniy, Voronezh Statel
Lab of Org Chem
~!'Zhur Obshch Khlp"',Vol 22, No 11, PP 1995-1997
Alkylbalogenophenols band alkyl ethers of.halo-
genophenols -have strong germicidal and - Insecti-I
,~6.1dal properties andliherefore are of definite
'Interest. They are -U IsUally obtained by the hal,6-
eanatIon of alkyl-'phpnols or alkylphenyl ethers
and more rarely bi~the action of sics or alkyl
238T'30~
balides on balogeaoph6nols. The dire Ict, alkyla-t
of halogenophenols vith olefins has hardly,
~b6in investigated.!; "The reaction of o-chloro
i)henbl vith cyclol~exene at rocm temp, and in the
loresence of the caiai~st, boron f2uoride ethyl
~Li-ther 'adduc., results'lonly
-in the formation of
the'cy~-Iobexyl of o-chloro p o
ether hen 1. There!
~ii significant polymerization of cyclohexene atr:
:the temp of a boilingliwater bath. Cyclohexyl
dither of o-chloro phen6l is quite stable and is,
i6t.isomerized in the']presence of boroti fluoride,
ethyl ether adduct~when heated for 8 hrs at 120-~~
.14o0
23BT30~~
E,
t2

Z A,!
Chardetil Abst. to of nic chem4".
Vol. 48 No. 9 r
n-MUll dJ. ~Gm S.S.
I "
I'lay 10 M.W. L),-&t C.A. 47, SW7&.
1954 H. L. li.
Org-3nicChoMi,gtry

.: ": ~; ;. ~ 1,%, :.. ~ ~ ~ 1, , i.; , i . -..
, . , , - ; -, , S~;F , ~~ .I , , ,
'Z ~r, -, , , ";' i~ -, :, ,,I I , 1:1 - i~, , : .2:
I- : 1. , , .4 j - ~ y - ., --" I i !L ; - , , , '. ~j 1 ~I ; - , - -, - -g
,, -. - ". 1- ~ , , , , - ~,-
13. r, . I
. r , -, ~ .1 1 ! ~ L , '. i. ,!.. ;~ , , - - ~, .~.

iT, C
An "I
N

lK

TOPGRIYLT,A.V.; ZAVGOROIMIY,S.V.,; PAUSHKIN,Ya.M.; SHUrKIN,M.I., radaktor;
ZZIZMVA.Ye.T., takhnicheekly re-
4aktor
[Boron fluoride and its compounds as catalyzers in organic
chemistry] Ftoristyi bor i ago soedinentia kak katalizatory v
organicbaskoi khImii. Roskva, Izd-vo Akademii nauk SSSR, 1956.
356 P. (HLRA 9:4)
1. Chlon-korrespondent AN SSSR (for Shuykin)
(Boron fluoride)

Z-
USSRI Organic Chemistry - Synthetic organic chemistry
Abs Jour : Referat Zhur - Khimiya, No 4, 1957, n684
E-2
Author : Zavgorodniy S.V., Vakhtin V.G.
Inst : -Vo-rone-zh University
Title : Alkylation of Anisole with Beta-Amylene in the Presence of Catalysts
Ethyletherate of Boron Trifluoride and Boron Fluoride Compound of
Ortho-Phosphoric Acid
Orig Pub : Tx:. Voronezhak. un-ta, 1956, 42, No 2, 37-39
Abstract- On- --alkylation- of anisole - (1) -with - beta-amylene (11) in pretidnce of
BY 3'H3PO4 were obt.ained 4-see-amylanisole (III) as principal reaction
product, 2-see-amylanisole (IV) and diamylanisoles (V). Alkylatioa
In the presence of BF etherate results i.n lower yields. To 9-5g
3
R 3PO4saturated with 5.2 g BF3 ) are added 27 9 1, and at/^-)200, are
added', within 1.5 hours, 35 g II. After 14-16 hours washed with wa-
ter, 5% NaR CO3, dried (to 1700 driving off I and II), yield of
Card 1/2

USSR/ Organic Chemistry - Synthetic organic chemistry E-2
Abs Jour : Referat Zhur - Xhimiya, No 4) 1957, 1i684
alkylate 62%; contains 80% 111, BP 104-106'/5 mm, n2OD 1.5164,
d~o 0.9584; 16% unpurified IV, BP 95-980/5 mm, n2OD 1.501-2,
d20 0.9330, and ^-)4% V. On oxidation of III with 5% HN03
4
there was obtained 4-CH 30C04 COOH, and. on oxidation of IV an
acid of MP 105-1070.
Card 2/2

fut
AUTHORSt Zavgorodniy., S. V.j end Kryuchkovas V. 0. 79-2-.12/58
TITLE: Boron Fluoride as a Catalyst in Organic Chemistry. Part 13. Alkylation
of 2- and 4-Bromophenole with Pseudo-Butylene and Cyclohexone in the
Presence of BY H?O-A, and BF3- WOO Catalysts (Ftoristyy bor kak.
11 1. Alkilirovaniya 2- 14-
katalizator v 9r*ganicheskoy khimli. f
bromofenolovpaevdobutile om i taiklogeksenom v priautstvii katalizatorov
BF3.H3F04 i BF3.0005)2~
PERIODICALs Zhurnal Obahchey Khimiit 1957, vol 27) No 2# pp. 330-333 (U.S.S.R.)
ABSTRACTs Investigation wags conducted to determine the &Ikylation of 2- and 4,bromo
phenols with pseudobutylene and cyclohexone in the presence of two boron
fluoride catalysts. It is shown that the alkylation of 2-bromophenol with
pseudobutylene leads to the formation of phenol Ta--Aucts or mixture of
other and phenol products. In all other-cases the authors obtained only
eater type compounds. The alkylation products derived are identified as:
secondary-butyl-2-bromophenolp secondary-butyl ether of 2-bromopbenol.,
secondary-butyl other or aeoondai7~.Wtyl...2-bromophanolj cyclohexyl eater
of 2-bromophenolp secondu7-butyl other of /+-bronophenal, secon&a7 butyl
Card 1/2 ether,, 2-secondary-butyl-4,-bromophenol and cyclohexyl ester of 4,bromo-
phenol. The effect of the molar ratios of reapnts cnd catalystap and

Boron Fluoride an a Catalyst in Organic Chemistry, Part 13. 79-2-12/58
effect of time and temperature on the total yield of other and phenol
baae compounds is described in a table.
1 table. There are 4 Slavic references.
ASSOCIATION: The Voronezh State University
PRESWED BYt
SUBMI=t March 1, 1956
AVAI LABIX Library of Congress
Card 2/2

AUTLHOR VDOVTSOVL YE.L.0 UVGORODNIY S.V. ?A - 3152
TITLE Aliqlatiox of Diane 4dra4&rbonx.AlkerqlLti*1
of knisole By Piperyleze,
(Alkilizov AJjs aromatichaskikh sayedinonly d4yono i uglerodoro.
dAut. Alkesiltrovanlis anizola piperilenon. -fteeMILT
PERIODICA1 Daklady Aktdeall Irauk USSR,1957,yol 113PIr 3oPP 59#-593 .0.8 R.)
Reselyed 411957 Reviewed A1957
ABSTUCT A systematio investigation of the reaction on the occasion of the
alkylation of the aromatic oar* with pyperilene (a by-produot obtai.
ned when produsing synthetio rubber by tho-Lebodev method) wto car-
ried out for the puVoss of duteraining the reaotirity of pleryleas
from a double-funational sombinatim By the example of aniaoi it is
shown to be possible to alkylizo the aromatic core with piperyloneg
viso with a yield of 56 - 92%~of the theoratioal quantities of peA-
tall anisole. The anisol* was selseted as the first *xpoTimental ob.
jeat because It represents thosi substaness Vhich have a sufficient
amevmt of movable hydrogens in order in this way to avoid the use of
SAargetio Gatalysers and thus also a Polymerization of the pioryloneo
Molecular compounds of boron fluoride,wero tried out as eatalyzerso
With.s.11 these astalyzers the alkylation process suppresses the pa-
lymerlza"oa of the pi*rTI#Aoo ;Results are, mhovA together in for2
of a table. Tho-struoturs of the postenilo anisoles was proved* Pon-
Card 1/2 tenilanisole was obtained In the presence of DE3.0(C215)2 and is in

Alkylation of Aromatis Compounds By Dions lVdrocarbons. ?A 3152
Alkanylation of Anisole By Piperylene.
its basic mass a 4-(n-molh*XYPh&AYI)-Penton-2(11) vhiah Is men-
tionsd In publiostions as an intermediate produot In the synthesis
2g3-to.(A-orlphanyl)-pentanse The products ottained by alkylation
ia the presence of BF R PO 37 9 PO appar*ntly coAsist es-
sentially of The exyorlmouls are do-
(111th I table sad 7 819vie refor0nods)-
ASSOCIATION State VnIv*raity of Toromesh
PUSENTIM BY TOPOMET A.V.j Member of the Asedeny
SUBMITTIM 15-11A956
AUILABLE Library of CoWess
Card 2/2

79-28-5-37/69
AUTHORS: Zavgorodniyj S. V., Sigovp 0. V., Bayevt 1. Fo
TITLE: esis of 1#4-Diisopropylbenzehe and Some of its
Conversions (Sintez 1,4-diizopropilbenzola I nekotoryye yego
prevrashcheniya) I
PERIODICAL: Zhurnal Obshchey Khimii, 1958, Vol, 28, Nr 5,
ppd 1279 - 1284 (USSR)
ABSTRACT: In the present work the alkylation of the isopropylbenzene
with propylene in the presence of BF 30 H3PO4 waa dealt with,.
When using these three compounds at equimolar ratios
(4 : I : o,26) at 98 - loo0C the lo4-diisopropylbenzene was
obtained in a yield of 73~o (at 52 to 550C - 19%). The oxidation
of the IP4-diisopropylbenzene (in liquid phase) with atmoslbwic
oxygen in the presence of various stimulators In mono- and
dihydrogen peroxide was investigated. During some time of this
oxidation an accumulation of peroxide to a certain maximum
takes place, on which the decomposition begins and the amount
~Card 1/3 decreases. At 11o0C such a maximum is reached after 12-14 hours,

79-28-5-37/69
Synthesis of 1,4-Diisopropylbenzene and Some of its Conversions
at 8500 after 2o-4o hours, depending on the stimulators. The
stimulator mixture, consisting of manganese resinate and
cobalt acetate with an addition of calcium hydrogen peroxide
stimulates oxidation much more than the first two, taken singly.
The addition of sodium ste~arate to the mixture accelerates
the oxidation and makes it possible to obtain 51% hydrogen-
peroxide at 850C during 17 hourof whereas without stRarate
onlY 33% result at 11oOC during 16 hours, on which the decom-
position of the peroxide ptarts. Calcium-hydrogen-peroxide also
accelerates the oxidation and strengthens the hydrogenparoxide
which leads to a deeper oxidation. The oxidation is mainly
directed to the formation of monohydrogen peroxide of the
diisopropylbenzene in the cleavage of which in acidous medium
the 4-inopropylphenol forms in a yield of 9o%. Partially also
dihydrogen peroxide of the diii3opropylbenzone forms which
Card 2/3 then splits into hydroquinone. There are 2 figures) 1 table
Wd 5 "fereuceet 4 of vhich a" Soviet.
ASSOC"IOR: Vomzzh- State Unimrsity

M
AUTAORS: Zave,,orodniyj S. V., Shvetsova, Lo S. SOV/79-26-10-C/6o
TITLE: Alkylation of loopropyl Benzene With Pceudobutylenie In the
Presence of BF 3'H3PO 4(Alkilirovaniye izopropilbonzola
paevdobutilenom v pristitstvii BF 3'H3 PO4
PERIODICAL: Zhurnal obshchey khimii, 1958, Vol 28, Nr lo,
pp 266a - 2670 (USSR)
ABSTRACT: In an earlier paper the authors already showed that the
molecular compound BF 3'H3PO4 proves to be a~h ighly
active catalyst in the alkylation of benzene kith psAido-
butylene. In connection herewith they alco atfqmpted to
alkylate isopropyl benzene in this way ;Y In thi6Icase the
reaction took place with more difficul ; Ise he
yields of the alkylation products were smaller. A-mixture
of isopropyl-aeo.-butyl benzenes wan formed which'con-
visted of about 91% para and 9~5 ortho isomers. The Most
favorable conditions with the highest yields of ioopropyl-
neo.-butyl benzenes are offered by the molar ratios
of. inopropyl benzene, pacudo butylone and catfilyst of
Cnrd 1/2 3-3,5:1:002-0,3, the temperature of 50-600, and the
"j-

'Alkylation of Isopropyl Benzene With Pseudobutylene
in the Presence of BF H PO
3' 3 4
SOV/79-28-lo-6/6o
introduction velocity of pseudo butylene of 1,6-20 e/hour.
In the case of a larger amount of the catalystf thle yi-ld
of isopropyl-sec.-butyl benzenes decreases; it also decreases if
there are more thqn 3 mole Inopropyl benzene per 1
mole pseudo butylone, oven with a larger quantity of the
catalyst. A considerable role Is also played by the veaotion
temperature. The-yiold of inopropyl-seo.-butyl benzenes
is, for instance, 18~6 at 200,'47% at 300--350 and 55cit at
50-600. At 1000 thR~paeu'do butylene in not readily absorbed
by the mixture, with the cataly.94 also gradually losing
its activity, which again cauoon a aivall yield. There are
1 table and 2 reforencen, 2 of which are Soviet.
ASSOCIATION: Voronezhskiy gosudarstvennyy universitet (Voronezh State
University)

AUT.'-dRS: ~gK&2r2~~~ and Sideltnikova, V. Is 20-1-27/58
TITLE: The Alkylation of Diphenyl by Pseudobutylene In the Presence of thr.
Catalyst BF."Y04 (Alkil-irovaniye difenfla psevdobutilencri v priautato
v1j katalizatora 1IF3.113POll)
PERIODICAL: DokladyMI SSSRI 1958., Vol. 118, Nr 1, pps 96-98 (USSR).
ABSTRACT: The authors studied this reaction in different molar ratica of the
two substancen and the catalystj without solvent and dissolved in
CC3~jl at 5o-1-oo0C- It was proved.that this reaction takes place in
mol-ax ratics I. - 4 : 1 1 0.,2 - 0,,3 and yielets monobutyldipherqls. as
maiii producta. Besides at 700C and above an isomerization of psaudo-
butylene to isobutylene taker, place and a mixture of p-secondrbutyl-0
diphenyl. develops. Their relative quantities depend on the temperature
and on other factors. When the ratio of the two reacting substances
and of the catalyst is,2 ! I : 0.,2 and when the temperature is, go0r,
the total yield of monobutyldiphenyl amounts to 36j80/'6 of the tbeon
retically possible. The relative content of p-aecond-butyldiphenyl
and p_tert._butyldipbeWl ia 740/o and 260/o respectively. Tbe most
favorable conditions under which monobutyldiphenyls- with a 58.~6o'o/o
Card 114 yield form-and amount up to 920/o in the result of alkylation, aret

The Alkylation of Dipherjyl by Pseudobutylene in the Presence of the 20-1-n/58
Catalyst BF3 "YOW
the ratio of diphenyl. ; pseudobutylant : catalyst a 1175 : 1 19 0125,
a temperature of 9oOC and the speed of the introduction of pseudobu-
tylene 2.5-3 liters per hour, The reduction of the quantity of catau
lyst to 0~13 Lol under the last-mentioned conditions diminishes the
yield of monobuty1dipheny13 to 32 O/o. The Increase in the quantity
of diphenyl, to 3 and 4 Hol per I Mol poeudobutylene reduces the yield
of monobutyldiphenyin to L9-290/o. But now the polybutyldiphenyls
are absent In the result of alkyintion, The ratio of the reacting subs
stances and the catalyst 1 : I : 0,2 leads to a-)13-45 O/o yield of
monobutyldiphenyls: and a 7-80/o yield of pol;ybutyldipheriyls of the
theoretically possible yields. In a CC14-solution the alkylation pro=
ceeds; very slowly and in molar ratios of the reacting substances and
the catalyst of 1. '. 1 *0 0:15j I *- I ', 0.0., 3 ; I 1 0.,3 it gives yields
of monobuty1dipherrili 12p U and 180/o of the theoretically ones. An
experimental part with the usual data follows. The constants and
yields of the monobromidoB of the two above-mentioned p-butyldiphenyls
and the self-oxidation as well as the splitting up of the hydroperos
xide of p-,second.-butyldiphenyl are described*
There are I table, and 4 references, 3 of which are Slaviv.
Card 2/10
'Cot.. \(O R'6 IV,

AWSOVA, Z.V.; ZAVGCRODNIY, S.V.
Alkylation of anioolo and phanetole by isobutylene In t~4
PQ#& Zhu-.obkhim. 32 no.11;3502-3505
prosence of BF v . H -
N, 162, (MM 15:11)
1. Kiyevskiy politekhnickeekiy institut,
(Anisole) (Phenstole) (Propene)

A.M.)* ZffILIITAP R.I.J FURTICIIEVI" R.F.;
SIV.TAIbVo V.P,; ZAVGOROD?fIY S V
t-ynthesin and autoxidation of isopropyleyclohexy:Lbenzenes
Zhur.ob.khim. 32 no*9;2954-2957 8 '62- (MIRA 115:0-
1. Kiyevskiy politekhnicheskiy institut.
(C=ene) (Oxidation)

NOVIKOVI I.N.1 ZAVGORODNIY, S.V.
Autaxidation of p-dicyclohezilbenzene. Dokl.AN SSSR 148
no.4s853-855 F 163. WRA 1614)
1. Kiyevskly politekhnicheskly inatitut. Predstak~eno
sk-e-ge-mikaft A.V.Topohiyevym.
(Benzene) (oxidation)

ZAVGORODITIY, S.V.*; IRDOUTNA, T.G.; SHUIVJMR. A.Y4,
Boron fluoride as a catal7st in organic chemistr7. Part 14:
Alkylation. of toluene and ethylbenzone by popmdobntylone.
Trudy VGU 57:107-116 159o (MM 13:5)
(Butane) (Tolune) (Beasene)

m
- 7AAVGORODHIY S
~
Boron fluoride as a catalyst in organic chemistry* Part 15:
AUVIation of naphthalene by olefina from by-produate of the
synthetic rubber industry. Trudy VGU 57:117-131 159-
(KIRA 13:5)
(Naphthalene) (Olefins)

ZOGORODITTY, S.V.
-----------
Boron fluart4a as a catalyst In organic chemistry, Part 16:
Alk~lation of gualacol and phonetoln by poeudobutylona.
Trudy VGU 57:133-140 159. (MIRA 1315)
(Guaiacol) (Phenqtole) (Butene)

5 (3)
AUTHORS: Zavgorodniy, S. V., Kryuchkova, Y. G. SOY/79-29-4-64/77
TITLE; Alkylation, of 4-Bromophanol With Propylane And P-Amylene in the
Presence of the ICatalyats BP3 HPO4and BF3 0(02H5)2
[AlkilirovaniYe 4-bromf enola propil enom i P-amilenom v prisutstvii
katalizatorov BF3 H3 PO4 1 BF3 0(C 2HN
PERIODICAL: Zhurnal obshchey kbimiij 1959t Vol 29, lir 41 Pp 1340 - 1343
(USSR)
ABSTRACT: This is a continuation of earlier investigations (Refs 1-0s, In
the present paper the authors investigated the alkylation of
4-bromophanol with propylene in the presence of BF 100 and
3 4
with P-amyleno in the presence of BF 3 O(C2H02 and BF3 HPO4 in
4-bromo-
carbon tetrachloride without solvents. It was found that
phenol yields with propylene and P-amylene in the presence of
BF3H 3PO4 and BF31O(C 2H5)2 only ether products. Two compounds,
the isopropyl other of 4-bromophenol (1) and the isopropyl ether
of isopropyl-4-bromophenol (II) are obtained with propylene. A
Card 113 secondary amyl ether of 4-bromophonol (III) was obtained with

__ ___ - - 1-1- 1.";. 1, i i ~-! .: ", ' -~i; ;a~z' '7~4' :' 1,
Alkylation of 4-Bromophenol With Propylene and BOV/79-29-4-64/77
P-Amylene in the Presence of the Catalysts BF 3 HPO4
and BF3 O(C2H5)2
P-amylene. The molar conditions of the reaoting compounds and
the catalyst 2:1:C,2 are for the alkylation of 4-bromophenol
with propylene in the presence of BF3 H3PO th best &t 300 and
. t,ise
in the case of slow addition of propylen Ids of (I) and
(11), 48 and 141A respectively). These products resulted in the
same total yield'(62%) in the molar ratio 1:2:0?15 of 4-bromo-
phenol, propylene, and catalyst. In this case, however, con-
siderable quantities of resin are producea and the yields in
(1) and (II) amount to 37 and 25~ respectively. The temperature
rise up to 500 increases the resin formation and reduces con-
siderably the yield in alkylation products* The application of
CCI, as solvent reduces the resin formation as well as the yield
in I) and (II). Further data are given in table 1. The alkyla-
tion0f 4-bromophenol with P-amylene in the presence of BF 3 HPO4
in a carbon tetrachloride solution is at room temperature accom-
panied by a polymerization, The yield in ether (III) is here not
Card 2/3 higher than 4qa- In the presence of BF 3 O(C2H 5)2 in the same

k1kylation of 4-Bromophenol With Propylene and SOY/79-29-4-64/77
P-Amylene In the Presence of the Catalysts BF 3 HPO4
and BF O(C H
.3 2 5)2
solution thereaction procooda more smoothly and the yield can
be'inoreased up to 7Z under a certain optimum molar ratio. An
intensive resin formation takes place without solvent. The in-
fluence of the reaction duration and other conditions of the
reacting compounds and the catalyst is illustrated in table 2.
There are 2 tables ana.6 Soviet references.
ASSOCIATION:. Voronezhskiy gosudarstvennyy universitet (Voronezh State'"
University)
SUMITTED: FebruarY 5P 1958
Card 3/3

SOV/79-29-5-8/75
AUTHORS: Zavgorodniy, S. V., Volkov, R. 11.
TITLE; Alkylation of p-Diisopropyl Benzene With Propylene in the Presence
of the Catalyst BF 3'H3PO4 (Alkilirovaniye p-diizopropilbenzola
propilanom, v prisutetvii katalizatora,BF 3#H 3PO 4)
PERIODICAM Zhurnal obshchey khimiit 1959, Vol 29, lir 5t
pp 1447 - 1449 (USSR)
AD15TRACT: In the present paper the alkylation of p-diisopropyl~ benzene with
propylene in the presence of the oatalyst BF 3*H3PO4 in the
temperature range 3 - 105 0 and at a ratio of ~-diiaopropyl bon-
zene, propylene and catalyst 1-5tl: 0-1 - 0-5 was investigated.
Triisopropyl benzenes and tetraisopropyl benzene were found to
be formed, Trii~uopropyl benzenes represent a mixture of 19294-
and 1,3,!5-t4dsopropy1 benzenes. Their relative content in the
mixture is 80-82 and 18 - 20dillp respectively. According to the
conditions:the total yield is 53-84%. The yield in 1,2,4,5-
tetraisopropyl benzene is 5-25r/L Optimum conditions for the
alkylation were determined as followsi the molar ratio of n-
Card 1/2 diisopropyl benzene - propylene - oatalyst 3 1 1 : 0-3p

Alkylation of p-Diisopropyl Benzene With Propylene SOV/79-29-5-8/75
in the Presence of the Catalyst BF H PO
30 3 4
tomperaturo 60 0, rate of propylone introduction 1-5 1/h and
subsequent mixive of the reaction mixture for 40 minutes. Under
those conditiona 81~j triisopropyl benzenes and 15%, 1029495-
totraisopropyl benzerie are obtained. In thin case other pro-
ducts are formed to practically no extent. As can be ooen from
the table the yield is considerably influenced by the quantity of
the catalyst. There arc 1 table and 2 references# 1 of vhich
is Soviet.
ASSOCIATIONs Voronezhokiy gosudarstvennyy univereitet (Voronezh State Uni-
versity)
SUBMITTED; April 11, 1958

S/153/60/003/005/005/016
B013 ZB056
AUTHORS: Zavgorodniyj S.V.t Novikovt I.N.
TITLE., Autooxidation of p-Diisopropyl Benzene
PERIODICAL; Izvestiya vysshikh uchebnykh zavedeniy. Khimiya i
khimi che skaya tekhnologiya, 1960~ Vol-. 3 9 No - 5, pp. 863 867
TEXT- The possibility of oxidation of p-diisopropyl benzene, forming in
-the alkylation of benzene with a propane - propylene mixture in the
presence of BF 3*H3PO4 into hydrogen peroxides, and subsequent cleavage
of the monohydrogen peroxide-into p-isopropyl-phenol, and of the dihydro-,/
k:en peroxide into hydroquinone, was studied in this paper. Autooxidation
of p-diisopropyl benzene at 850, 1100, and 1300C in the presence of
diisopropyl benzene hydrogen peroxide and manganese resinate with alkaline
additionso as woll an cleavage of the hydrogen peroxides into correspond-
Ing phenols, was studied for thic purpose. It was shown that the rate of
oxidation of industrial p-diisopropyl benzene dopenda on itn purity.
NaOH, KOH, Ca (0H)2 and Na 2CO3 were used as additionn. These materials are
Card 113

Aut,ooxidation of P-Dii0opropyl Benzene 3/15 ~60~003/005/005/016
BOT 05
only little effective in themselves, and have all about the same effect.
Their addition (0-5 -1 g per 1 mole of diisopropyl benzene) to the
manganese reninate, however, initiates the autooxidation process, and
permits a deep-reaching oxidation of the hydrocarbon up to the hydrogen
peroxide. Autoozidation becomes specially intensive if p-diisopropyl
benzene is preoxidized in the presence of alkaline additions up to a
content of 2 - 3~* hydrogen peroxide in the solution. Manganese resinate
cr diisopropyl benzene hydrogen peroxide is subsequently added, and oxi-
e.ation is continued withthe blowing-through of air. Under such conditions,
a maximum hydrogen peroxide concentration of;76.'/o was pbtained within 44
hours at 110 � 20C. The experiments showe4 that p-diisopropyl benzene
dihydrogen peroxide is only precipitated if the hydrogen peroxide con-
centration in the hydrocarbon solution is higher than 40%. It may be
assumed that in the oxidation of p-diisopropyl benzene, monohydrogen
peroxide is formed first. Not until this has reached a certain concentra-
tion does it begin to oxidize into p-diisopropyl benzene dihydroeen
peroxide. The cleavage of the dihydrogen peroxide proceeds most smoothly
with concentrated sulfuric acid in ether, the highest hydroquinone yield
being obtained here. Strong resinification can be observed with dilute
Card 2/3

Autooxidation of p-Diisopropyl Benzene s/i53/6o/oO3/0O5/0O5/O16
B013[B058
uric -acid. ..By- -reproduction of pure dihydrogen peroxide, 96% of
p-di-(,A,oV-_oxy-isopropy f)- -be-nz en,e-w-a-o ___ obtain-ed-in-the-form-of white-
.noodleo,with a molting point of 1400C. Figa.1 - 3 show the effect of the
purity of diinopeopyl bonzoneg tomporature, ond various.admixtures on the
rate -of oxidation* M. Xruthalov and V,V& Podorova aro mentionel. Thore
are 3 figures,-2 tables an(1--5'8oviet references.
ASSOCIATION: Voronezhekiy gosudarstvennyy universitet.Kafedra irganicheskW
khimii (Voronezh State UniverBity.Department of Organic
Chemistry)
SUBMITTED: February 17,1959
Card 3/3'

KRYUCUK07At V.Q,; ZAV(;OI?DDIIIY, $.V.
Alkylbalophenoxyac.atic acids. Zhur.ob.khtm. 30 no.3i
1747-1748 W 160. (MIRA 13:3)
1, Voronsibekly osudarotvonMy univernitat,
Vcatic 4CM)

KRYUGHKOTA, V.G.L_UVGORODMIY, S.T.
AlkIlation of 4-bromoonsisole by propylene, poeudobutylene,
and cyclohexens in the presence of B'3-"3PO4- Zhux.ob.khim.
30 n'0,6;1929-1932 Je 160& (MIRA 13:6)
1. Toronezhakiy gosudarstvennyy universitete
(Anisole) (Alkylation)

8561o
B/079/60/030/007/026/039/XX
21003, W~3' 11.21 BOOI/BO66
AUTHORS: Zavgorodniy, S. V., ZaXtsev, B. A., Yel'ohinov, D. P.
TITLE: kryl-alkylation of PhenoAWith Styreneland a-?Aethyl Styrene
PVRIODICAL., Zhurnal obahchey khimii, 1960, Vol. 30, No- 7, pp. 2196-2199
TEXT: The aryl-alkylation of phenols with aryl olefine has so far been
given little attention, In spite of the practical importance of Its reac-
tion products (Ref. 1). The authors studied the reaction of phenol with
styrene and a-methyl styrene, using the ethyl etherate of boron fluoride
3- 2 5)20 and boron fluoride with 75% orthophoophoric acid as catalysts,
__(C H
In both cases ar yl alky _p_he_n_o'_1_s__ r6jult ed -.--Styrene -gave -a -mix ture -of - mono-
aryl and diaryl alkyl phenols (32 .. 60% yield, according to conditions),
a-methyl styrene p-hydroxy-diphenyl-dimethyl methane (60%), and a small
quantity of resinous products whose composition could not be determined.
In both cases, aryl-alkylation is accompanied by polymerization of the aryl
olefins, which is the main reaction in the case of styrene. a-afethyl
styrene is more stable to polymerization, and Is partially dimerized (in
Card 1/2

85610
Aryl-alkylation of Phenol With Styrene and 3#9/60/030/007/026/039/XX
a-Mothyl Styrene BOOI/BO66
addition to the formation of resinous polymerization products) to give
the crystalline 1,1,3-trimethyl-3-phonyl indan which distills over together
with p-hydroxy-diphonyl-dimethyl methane. The beat yie14 of hydroxy-diphen-
yl-methyl methane was obtained at a molar ratio of 2 : I : 0.06 between
pher.ol gtyrene, and the ethyl etherate of boron fluoride, at a temperature
of 95-~7 and with a reaction time of two hours. In the reaction of phenol
with a-methyl styrene in the presence of the above etherate, the best
yield (60%)-of p-hydroxy-diphen~l-dimethyl methane results at a molar
ratio of 3 1 ; O-15v at 80-83 and with a reaction time of nine hours.
Thiii reaction may be represented in the general form:
BF -O(C It ) I
21,
R R
HO - +CH2-C C:> HO-
(R - 11 or CH 3).
There are 2 tables and 2 referencest I Soviet and 1 German.
ASSOCIATION! Voronezhskiy gosudarstvennyy universitet
(Voronezh State University)
SUBMITTED: July 6, 1959
F

ZATOOROMU, S.V.; SHAUKUDYA, Y.G.
Autooid on of P -ethyl- socebutylbousens. Zbw.obekbix.
30 no-7:2402-2406 JI 160. (MM 1337) t
1. Voronesheldy*gosudArstvemW universitats
Owaseas)
Is

84874
S/079/60/030/010/010/030
B001/B075
AUTHORS: Shalganova, V. G. and Zavgorodniy, S. V.
TITLE: Autooxidationlof Secondary p-B-u-ty-ltoluene
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol. 30, No. 10,
pp. 3223-3226
TEXT: The authors studied the autooxidation of p-sec-butyltoluene and
carried out a quantitative determination of the products of acid splitting
of hydrogen peroxide, as well as of the products obtained from a complete
oxidation of p-see-butyltoluene. The oxidation took place at different
temperatures.Autooxidation carried out by means of atmospheric oxygen in
the presence of manganese resinate, caustic soda, and other additions,
proceeds most conveniently at 110 0C. It was shown that in the presence
of manganese reBinate and alkali the oxidation of the secondary butyl
radical proceeds 1o8 times more easibr than that of the 'primary methyl
group, and 1.2 times more eWly than on the addition of sodium stearate
or cobalt acetate. The main productsof oxidation are p-methyl acetophenone,
p-tolylmethylethyl carbinol, and p-seo-butyl benzoic acid. It was found
Card 1/2
-"~T-P-44P

84874
Alitooxidation of Secondary p-Butyltoluene 3/079/60/030/010/010/030
BOO1/BO75
that p-sec-butyl benzoic acid can be oxidized with atmospheric oxygen to
form p-acetyl benzoic acid in a 30-51o yield, The oxidation rate of p-sec-
~butyltoluene at 1100C.under,different conditions is illustrated in a fig-
ure. Experimental data are given in Tables 1 and 2. There are I figure,
2 tables, and 11 references: 9 Soviet, 1 US, and 1 German.
ASSOCIATION: Voronezhakiy gosudarstvenn y univereitet
(Voronezh State University
SUBMITTED: November 4, 1959
Card 2/2

87523,
S/079J60/030/012/003/027
IZ09 B001/13o64
AUTHORS: Kryuchkovap V. G. and Zavgorodniy, S. V.
TITLE: Alkylation of 2- and 4-Anisole Chloride With PentenG-1 in
the Presence of BF 30 113PO4as Catalyst
-PERIODICAL: Zhurnal obBhohey khimii, 1960, Vol- 30, No. 12,
pp. 3869-3871
TEXT: For several years the authors have studied the alkylation of
phenol halides and anisole halides with olefins in the presence of boron
fluoride catalysts. Alkylation is a very convenient method of synthesiz-
ing interesting alkyl halide phenols which have hitherto been hardly ac-
,ansaible ta la!~oratovy. Thi3 13 a continuation of previous studies de-
af; ribing the rtz~altr. of alkylatimig 2- Ar,1 4-anlsf~li wish ;,antana-l
In tho praoonoo of B?,.sH~POI a* catalyst. In cont.rait tht raac--Ion
4-aninolo 6h1oride vifIl fo~ylenq, Cyalo~JeXg:1.e. InA 4-giz.'_
0014 bromlda ivlth propylone, an4 cyclohaxong (Hof. 1), only
anitiola uhloridoti otres obtlilflott. ;!,-aijtot)lq 0111ot,144 eAlky1n4ol with plentono-1
1-5 times more readily than 4-ani"olo ahlorlda untlar u1milar contlitiona.
The molar ratidd 30:00 between 2-phenol chlorido, pontene and tho caltaly;~t,
-Card 1/2

Alkylation of 2- and 4-Anisole Chloride With
Pentene-1 in the Presence of BF 3&H3PO4 as
Catalyst
87523
S107916010301040210031027
BOOIIB064
and a temperature of 40 0C proved to be the optimum conditions under which
the 4-sec.-amyl-2-anisole chloride yield %as 66~o. To synthesize 2-sec.-
amyl-4-aniaole chloride in a 54% yield, the molar ratio of the reagents
and the catalyst duet be 4:1:0.29 and the temperature 400C. A temperature
between 20 and 60 C has no.essential effect upon the yield in alkylation
products. The ratios of the reagents of 4:1 to 2:1, and the amounts of
catalyst between 0.1 - 0.3 per I mole pentene-1 bear also no influence
upon tbo yields. Tho'beat results are obtained when the calculated amount
of anicolo ohlorido in at once added to tho catalyst and when pentene-I
Is slowly added to this mlxture* When pontene-I is mixed with a part of
anieole chloride, the yield in alkylation produoto io lower* There are
2 tables and 3 Soviet references.
ASSOCIATION; Voronezhskiy gosudaretvennyy universitet
'Voronezh State University)
SUBMITTED: February 4j 1960
Card 2/2

87524
S/079J60/030/012/004/027
S' 30LOO FoolIB064
AUTHORS: Kryuchkoval V. G. and Zavgorodniyp S. V.
TITLE- Demethylation of Alkyl Halide Anisoles
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol- 30, No- 12,
pp. 3872-13873
TEXT: The authors demethylated several alkyl halide anisoles hitherto lit-
tle investigated. This paper does not d1ocano the rate of demothylation
and the finding of the. boot reaction. conditions, but the synthesis of alkyl
hultdo phonolo. Novortholeua,- the roaulto obtainad laud to Intoreating con.
aluaiona on the behavior of the anitiole group toward hydriodio itaid Lind hydro-,
bromio acid. It van found that all monoulkyl aubatituted o- and p-fluoro
anisoles and o- and p-ohloro anisoles can be domethylatod into the correspond-
ing alkyl halide phenols when heated with HI or HBr for a longer time; this
demethylation, is, however, not quantitative- 4-alkyl-2-anisole halides
demothylate more readily. Among the 14 alkyl halide aniaoloo, 4-sec.-amyl-
2-fluoro aninole demethylato moot readily to 4-nec,amyl-2-fluoro phenol
(86% yield) (Table), 2,6-dialkyl-4-anisole halides do not demethylate with
Card 1/~

875?4
Domethylation of Alkyl Halido Anivolon 01079160103r,,101210041027
BOW/Bo64
HI and HBr under ordinary conditions; the reason is the blocking-of the
methoxy group by the two alkyl radicals which are in ortho position to it.
At continuous heating of 2-cyclohexYl-4-ohloro anisole with HI, besides
demethylation also a splitting off of the chlorine atom takes place, which
instead of the expected 2-cyclohexYl-4-chloro phenol leads to 2-cyclohexyl
phenol. There are 1 table and 3 references: 2 Soviet and 1 British.
ASSOCIATION: Voronezhskiy gosudarstvennyy universitet
(Voronezh State University)
SUBMITTED:
Card 2/2
February 4, 1960

- . . . I ~ .-1.1-111-17 1_-!1-1-.--Tj~f,i~-- . M,;._..__.,__.,. .--- - Vl__
S/079/60/030/012/011/027
BOOI/BO64
AUTFORS. Shalganova, V. 0. and Z
TITLE: Autooxidation of 4-sec.-butyl-o-xylene
PERIODICAL: Zhurnal obahchey khimii, 1960, Vol. 30, No. 12,
PP. 3964-3967
TEXT: The authors investigated the autooxidation of 4-Bee.-butyl-o-xylene
M with atmospheric oxygen at 1100C in the presence of manganese resinate,
combined with Ca(OH )2 , NaOR, Na2COP sodium atoarato, cobalt acetate. The
compound was oxidized up to the maximum concentration of the hydroperoxide
or the complete vanishing of the-latter from the reaction mass. The maxi-,
mum*concentration of hydroperoxide was found to depend on the type of the
admixture and the amounts of manganese resinate. The maximum concentration
of hydroporoxide (13 %0) in caused by the autooxidation of butyl xylene (1)
in the presence of resinate and Doda with the following products forming
from the reaction mass until the complete vaniehing of hydroperoxide:
3v4.-dimethyl acetophenone (11); o-xylenol-(1p2,4) (III); 1,2-dimothyl-
phonyl-mothyl-othyl carbinol (IV)j 2-mothyl-4-aoc,butyl- and 2-mothyl-
Card 113

Autooxidation of 4-00c.-butyl-o-xylane S/079/60/030/012/011/0-27
BOO1/BO64
5-Dec.-butyl benzoic acid (V); 2-methyl-4-sec.-butyl- and 2-mothyl-5-nec.-
butyl benzyl alcohol (VI). The oxidation of (4-sec.-butyl-o-xylene) in the
presence of manganese resin~te, sodium atoarate, and calcium hydroxide
with atmospheric oxygen (10 I/h) in a timo of 60 h gave a 25-8 ~o yield
of oxidation products. The products (II-VI) form at a molar ratio of
3.75 : 1 : 3 : 5.65 : 2-5. The yield of the oxidation product was 32.3
in the presence of resinate, cobalt acetate, sodium stearate, caustic
soda, and calcium hydroxide. The products III-VI) were obtained in a
molar ratio of 7-5 : 1 : 3 : 26 : 4. From the composition of the oxida-
tiort products it may be concluded that in the oxidation of 4-sec.-butyl-
o-x3,lene all three radicals are oxidized, under the formation of a hydro-
peroxido mixture: 2-methyl-4-sec.-butyl benzyl (VII), 2-methyl-5-sec--
butyl benzyl (VIII), and 3,4-dimethyl-a-methyl-a-ethyl benzyl (IX) which
were all identified by their reduction to alcohols. The time of oxidation
of all three alkyl radicals depends on the character of the additions.
Among two methyl groups, the one in para position to the sec.-butyl group
oxidizee more readily than the other. The sec.-butyl radical. oxidizes
in tho presence of manganeno roninate, oodium atottrate, and calcium
hydroxide twice as rapidly as the methyl radical. Thure are 2 tablei and
Card 2/3

Autooxidation of 4-sec.-butyl-o-xylene S10791601030101210111027
BOOl/BO64
8 Soviet references.
ASSOCIATION: Voronezhskiy gosudarstvennyy universitet (Voronezh State
University)
SUBMITTED: Januaryll, 1960
Card 3/3

1~4 7~2 6 0 0 68991
.AUTHORS: Topchiyev, V., kcademiciany S/020/60/i3l/02/033/071
Kryuchkova, V. G., Zavgorodniy, S. V. BO11/BOO5
l
TITLEs e in the
Alkylation of 4-Fluorophanol With Propylen and Cyolohexen
Presence of the Catalysts BF 3 9H 3PO4 and BY3.O(G2R5)2
PERIODICAM Dolklady Akademii nauk SSSR, 1960, Vol 131, Nr 20 PY 329-311 (USSR)
ABSTRACTs As the reaction of fluorophenols with olefins bad been negleoted
in publications, the authors studied the reaction mentioned in the
title In continuation of their previous papers. 4-fluorophenol
reacts more intonstly than obloro- and bromophonols. Together witb
olefins (with propylene) it forms a rather cor-plex mixture of pro-
duota, loopropylfluorophonolisopropyl other is alwayst isopropyl-
fluorophenol sometimes, formed besides the 4-fluorophenolisopropyl
ether.-The yields in individual products depend on the nature and
quantity ofthe ostalyet, the temperature, and the molar ratios of
the reagents. Thus, only others are formed In the prenence of
BP3'O(C2H5)2 at 600 whereas phenol products are missing, at least
In noticeable quantities. In the presence of BY *H3pO41 the yields
h
e temperature bet-
in phenol compounds are the higher, the higher
ween 46 and 700-The beat conditions for a formation of 4-fluoro-
Card 1/2 phenolisopropyl ether (506 yield) are% molar ratio of fluorophenol,

68992
Alkylation of 4-Fluorophonol With Propylone and s/o2o/60/131/02/033/071
Cyclohexene in the Presence of the Catalysts BOll/BOO5
BF 3OH3PO4 and BF3'0(C2H5)2
propylene and BF3;H3p0j - 31110-4 and 400; the same for isopropyl-
4-fluorophenoliso ropy other is, 511'0-3 and 600 (36% yield), and
0
for isopropyl-4-fluorophenol 3sls-,0.2 and 700 (38% yield). Table 1
lists these results. One product .Only - 4-fluorophanoloyclohoxyl
ether --la formed from 4-fluorophenol with cyclohexane in the pre-
senoe of BF3-H3PO4 with a yield of 70-7% of the theoretical one.
Already after the lot distillation of the alkylate, the product
has a boiling limit of 2-30 (Table 2). The compounds of the ether
type were identified by splitting into corresponding phenols and
transformation of the phenols into phenoxy acetic acids. Table 3
shows the physical and chemical constants of the ;rroducta obtained.
There are 3 tables and 6 references, 6 of which are Soviet.
ASSOCIATIONt Voronezhokly goaudarstvonnyy universitst (Voronezh State Universi-
ty)-
SUBMITTIMs November 19, 1959
Card 2/2

0 0
AUTHORS:
TITLE:
S/020/60/132/03/28/066
Boll/booe
Volkovp R,
Kinetic Peculi,arities.of the IookropX1 Xzlene Autoxidation
in the Liquid Phase
PERIODICAL: Doklady Akademii nauk SSSR9 19609 Vol. 132, No. 3,
pp*- 591-594
TEXT: In this paper the authors continued the previous investigations
(Ref. 1). They now studied the problem mentioned in the title on
polyalkyl benzenes with neighboring substituenta. o-xylene Mt 4-iso-
propyl-o-xylene (II)i 3-isopropyl-o-xylene (III), 2-isopropyl-p-xylene
(IV), 4-isopropyl-m-xylene (V), 2p5-di-ioopropyl-p-xylene (VI) and
o-eymene (VII) were investigated. It was determined that y-laotones
(phthalide-derivatives) also develop during the autoxidation of these
substances, besides alcohols, ketonesp acids etc. From (I) there forms
in the presence of 0.6 Mol-~ cobalt acetate; o-toluio aoid, 5-e% of
phthalidep and 2-5% mixture from toluyl aldshyde and tolyl carbinol.
The highest concentration of hydroperoxide does not exceed 1-1-5%-
Card 1/3

Kinetic Peculiarities of the Inopropyl 3/02 6011321031281066
Xyle-me Autaxidation in the Liquid Phase BO i I Y11OO8
A rather complex inixture develops from (II) at the oxidation. It can be
,seen from Table I that the yield of lactones amounts to approximately
5% of the oxidized hydrocarbon. Other products with two oxidized groups
develop in noticeable quantities at an intensity of the oxidation of
over 30%- (III)-(V) are very slowly oxidized in the presence of
manganese resinateo Cobalt acetate and cobalt isopropyl teluylene
accelerate the process considerablyo It was not possible to direct the
proooss by these two catalysts towards the predominant formation of
hydro peroxides, since these decompose very quickly in the presence of
cobalt salts. (VI) could oxidize at 1100C within 7 hours with 6 mg/Mol
mangs.nese resinate and 10 mg/Mol soda up to a 14 concentration of
hydro peroxides, The ioopropyl-group can be oxidized in II) almost
4 times more easily than the CH3-groupy but in (IV) and ~V) the total
rate of oxidation of the groups placed side by side in only 1-3-1-7
times greater than that of the individually placed groups, owing to
sterio hindrance. Fig. I shows the kinetics of the oxidation products
of (V) at 1300C in the presence of 1 Mol-% cobalt i8opropyl toluylate,
as well as of (IV) at 1600C. The rate of the introduction of air was
Card 2/3

Kinetic Peculiarities of the Isopropyl .3/020/60/132/03/28/066
Xylene Autoxidation in the Liquid Phase BO11/BO08
I 1/min. The composition of the oxidation products of (IV) and (V) is
givon in Table 2. It follows therefrom that lactonee develop at a
conaiderable rate already in the earliest phases. More than 50% lactonee
devolop.at,the oxidation of (VI)t (III) and (V11) give also high yields.
Basod on the ranultoo the authors come to the oonolunion that tho main
cauoe of the high yield of lactonealliae in the ioomerization of the
free radical (no* Scheme). Here ar 1 figuret 2 tables# and 5
referenoonp of which are Soviet.
ASSONATION: Voronezhakiy goeudaretvannyy universitet (Voronezh
--- State University)
PRESHNTED: January 8, 1960,-by A. V. Topchiyevp Academician
SUBMITTED: January 81 1960
Card 3/3

TCFCHMV, A.T., akademik; XUUCHKOVA, T.G.; UTGORODNIT, S.T.
Allwlation of 2-chloroonloole b7 prop7lane,
oyoloboxene in the presence of 27.y0 & DDkIAX BSSR
3 4
DALAN SSSR 133 n0-3:617-619 JI l6o. (MIRA 13t7)
1. Institut neftekbimicbeekogo sinteza, Akodemii nauk SSSR L
Voronezhakiy goeudaratyenmyy universitat.
(Anisole) (Allwlation)

86465
S/020/60/133/004/037/04OXX
B016/BO54
AUTHORS: Volkov, R. N., and Zavgorodniy, S. V.
__TITLEj The Character of Alkylation of Aromatic Hydrocarbons by
Olefins in the Presence of BF H PO
3 3 4
PERTODICALs Doklady Akad6mii nauk SSSR, 1960, Vol. 133# No. 4p
pp. 843-846-
TEXT: The authors.reporl, on the investigatio n of the- following alkylation
reactions in the,presence of the catalyst BF 3 'H3PO41 of benzene by
propylene, cyclohexene, as well as a- and -isobutylene; of binary mixtures
of toluene and benzene$ ethyl benzene, cumenep as well as o-, m-t and
p-xylene by the same olefinal of a mixture of benzene and ethyl benzene,
cumene, and the xylenes by,butylenes and cyclohexene; of a mixture of
m-xylene.with secondary and tertiary butyl benzene by propylene and
'~ -butylene; of benzene mixed with tert, -butyl benzene by cyclohexene; of
cumene, diisopropyl benzene, and a mixture of the latter with benzene, by
Card 1/4

86465
The Character of Alkylation of Aromatic S/020/60/133/004/037/04OXX
Hydrocarbonaby Olefins in the Presence B016/BO54
of BF 3*H3PO4
propylene. These experiments were made to check the assumption saying that
the presenoe of alkyl groups in the benzene ring strongly activates the
subotitution reaction only if the attacking agent has a considerable
positive charge. The authors performed the alkylation an it is described
in Ref. S. They made special experiments to determine the effect of de-
alkylation on the composition of the alkylate. They proved that only
hydrocarbons with tertiary butyl groups are noticeably dealkylated. The
rate of this process only depends on the concentration of the substance
to be dealkylated, and on temperature. Table I shows the alkylation results
of the benzene - toluene mixture. Hence, the authors conclude that neither
the reaction conditions nor the ratio of the reagents can strongly
influence the reaction rate of toluene. The same applies 'to the alkylation
of~-o-the-r--hydrocarbonf~_~y propylene, n-butylene, and cyclohexene. Only in the
roaotion of benzene and -i-ts h-o-m-o-lo-guen-wi-th-inobu-tylgne
temperature and
duration of the experi ment exerted some Influence in thi
Table 2 given the relative reactivities of benzene homologues to varioua
Card 2/4

The Character of Alkylation of Aromatic S1020160113310041037104OXX
Hydrocarbons by Olefins in the Presence B016/BO54
of BF 3*H3PO4
olefine. The catalyst BF 3'H3PO4does not produce a strong 4isproportiona-
tion of primary and secondary alkyl radicalsj nor does it form any "special
complexes" during alkylation. Table 3 shows the composition of the
alkylation products. Hence, the authors conolude that the relations of the
rate oonotants of nucaeaDive reactions do not depend on the intensity of
alkylation of an aromatic hydrocarbon. Therefore, it is possible to fore-
_--cast-the- composition of--the-alkylate---with-relativd -dcc-ura_c_y__. Theau-thars--
mention the phenomenon of hyperconjugation, but do not discuss it. For an
interpretation of several rules observed by them, they must assume that the
alkyl groups are an obstacle not only in ortho-, but also in meta- and
para-substitutions. Generally speaking, alkyl benzenes can reaut faster
(than with benzene) only with such olefins that are polarized by the
catalyst, and form ions with a highly effective charge, which are con-
centrated on the reacting carbon atom. Finally, the authors point out that
the rupture of the n-bond proceeds (,,radually during the formation of a
bond with the aromatic ring. This is confirmed by the difference in
Card 3/4

8646,5
The Character of Alkylation of Aromatic S102 60/133/004/037/04GXX
Hydrocarbona by Olefins in the Presence B016YB054
of BF 3*H3PO4
relative reactivities of alkyl benzenes and u- and IN-butylene. Thero are
3 tables and 9 references: 8 Soviet and 1 US.
ASSOCIATIONt Voronezbskiy gosudarstvennyy universitet (Voronezh State
University)
PRESENTED- March 19, 1960, by A. V. Topchiyev, Academician
SUBMITTED: March 19, 1960
Card 4/4

8h690
8/020/60/134/004/015/023
M6/Bo6o
AUTHORS: Topchiyev, A. V., Academician, Volkov, R. N., and
Zavgorodniy1-~-S-' V-..
TITLE: A~Study of the Rules Governing the Alkylation of XjLenes
With PS2fflen~elin Presence of Br3'H3P04
PERIODICAL; Doklady Akademii nauk 988R, 196ot vol. 134, No. 4,
pp. 844 847
TEM. The rules governing the alkylation of 0- (1), m- (II), and p-xylene
(III)-with propylene in the presence of BF H PO have not been studied
3 3 4
by previous researchers (Ref. 2), nor have their yields of isopropyl
xylene been higher than 52%. The authors of the present paper made a
I'll, re, time of re-
systematic study of the effects of catalysticoncentmba4*tempnlatt;
action, and molar ratio of reagentT--U-P--0-n-fFi-e yield and the composition
of the alkylation product of (I) - (III). In doing so, they established
,the conditions under which it is possible to obtain a 90% yield in
Card 1/4

A Study of the Rules GoIverning the Alkylation S/02o/60/134/oo4/o15/023
of Xylenes With Propylene in Presence of B016/BO60
BF3-113POI
isopropyl xylenes, and clarified the kinetic characteristics of the re-
action. Alkylation and fractional distillation were performed in the same
way as-shown in Ref- 3. The propylation of (I) gives rice to 4-isopropyl-
-o-xylene (IV), 3-isopropyl-o-xylene (V), and 4,5-diisopropyl-o-xylene
(VI), while (II) yields 4-isopropyl-m-xylene (VII), 5-i8opropyl-m-xylene
(VIII), 2-isopropyl-m-xylono (IX), 4,6-diisopropyl-m-xylene M, and
2,5-d.iieopropyl-.m-xylene (XI). The monoalkylate of (111) oxclunively
consists of 2-isopropyl-p-xylene (XII), while its dialkylate mainly con-
sists-of 21,5-diisopropyl-p-xylene (XIII). Table 1 contains the principal
constants of the resulting compounds and the xylene8 employed in the
process. Heretofore, there was no description of M and (VI) to be found
in publications. The authors describe the methods of identifying the
icomorB. Theywere oxidized to form benzene polycarboxylic acid, and
examined both refractometrically and by means of infrared absorption
spectra,. The authors further describe the separation of benzene tricarb-
oxy-1'LC--acidB-, -and- that-o f-their-eB-ters. The dilactone of 2,5-di-((A-oxy-
-isopropyl)-terephthalic acid was obtained from.(Xllr)-by-o-)t-l-dation-~--- --
Card 2/4

84690
A Study of the Rules Governing the-Alkylation 3/020/60/13VOOV015/023
,of Xylenes With Propylene in Presence of Boi6/Bo6o
BF3 *H 3PO4
Moreover, isopropyl xylenes were also identified by self-oxidation.
Results obtained fro m some experiments on xylene propylation are shown in
Table 2 and include composition of reaction mass, yields, ratio of apparent
rate constants of the alkylation. of isopropyl xylenes and initial xylene
(r = k2A1 ). It may be seen from Table 2 that an increase in temperature
and in the concentration of BF 3*H3 PO4 reduces the relative formation rate
of products resulting from secondary alkylation, an had already been
established previously by the first-named author jointly with N. V.
Kuranhev and Ya. M. Paushkin (Ref. 7). The rules governing the iso-
meri:sation of polyalkyl benzenes are formulated as follows: the migration V,
of the isopropyl group has an inner-molecular character, and chiefly
occu:rs whenever there are alkyl radicals in the positions 2,3, 2,4, or
2,3,,5 relative thereto. These rules, in addition to explaining the charac-
ter of the orientation of substituents, allow the process to be controlled
in such a way that the substances desired can be obtained with highest
yields. There are I figure,.2 tables, and 9 refereitces: 8 Soviet and
I US.
Card,3/4

no
A Study of the Rules Governing the Alkylation 6/020/60/13VOOV015/023
of Xylenes With Propylene in Presence of B016/Bo6o
BF.X.H PO
3 4
ASSOCIATION: Voronezhskiy gosudarstvennyy universitet (Voronezh.State
University)
SUBMITTED: April 29, 1960
Card 4/4
Olt'

26288
3/190 61/093/008/ool/0,19
0 D B1199B.220
AUTHORS: Rayevskiy, A. B., Kryuchkova, V4 G., Zavgorodniy, S. V.
TITLE: Effect of alkyl halophenola on the polymerization of styrene
PERIODICAL: Vysokomolokulyarnyye soyedineniyal v. 3, no~ 8, 19611
1121-1124
TEXT: The inhibiting effect of-~henol derivatives on the polymerization of
styrene and its dependence on the structure of the phenol derivatives were
atudied. The compounds mentioned in the legend of the figure were synthe-
cited to this and. Aniaole.halidea were alkylated by olefinp in the pro-
Bence of BF 3' R3PO4 and BF3-O(C.2H5 )2 -at 6000. Domethylation of the anisolo
alkyl halides obtained was performed in the presence of H1, HBr, and acetic
anhydride. Commercial styrene was purified from hydroquinone by treatment
with 20% KOHj dried over Al 0 and distilled in a nitrogen flow. Thj..molar
2 3 " 3 '%~,I!, ~
ratio of styrene to inhibitor was 5,10 :1. For comparison, otyren'e! was
polymerized without inhibitor.. The polymer content P was calculated from
the refractive index: P - (2.05-n 20 _ 3.17)-103. Results: 1) The nature
Card 1/4

S/190/61/003/008/001/019
Effact of alkyl halophenols on B11O/B220
of the halogens and their position influences the inhibiting effsotj
2) 2-alkyl-4-halophenole are stronger inhibitors than 2-halogen-4-alkyl
phenolst 3) fluorine derivatives are stronger inhibitors than chlorine
derivatives; 4) 4-fluorophenols show an increasing inhibiting effect in the
sequence: 2-seo-butyl-; 2-oyolohexyl-; 2-sec-amyl-; 2-icopropyl-4-fluoro-
phenol; 5) the inhibiting effect of 4-chlorine derivatives increases con-
versely$ 6) the nature of the alkyl radical has no essential effect in the
case of 4-alkyl-2-halophenolai 7) Since phenol derivatives have an inhib-
iting effect only in the presence of 0 2f the compounds studied did nolt show
such an effect in the polymerization of styrene in 'a nitrogen atmosphere.
There are I figure, 2 tables, and 7 references. 3 Soviet and 4 non-Soviet .
The most important references to English-language publications read as
follows: Ref. 1: E. 0. Edwards, Go F. P. Harriso Chem. Ind., 1955, 6251
R-ef.2t So G. Food, J. ohem. Boo., 1940t 48. Ref.6: USA Patent 2p 221
809, 1940.
ASSOCIATION: Zavod sintetichaskogo kauohuka. imo So Ho Kirova (Synthetic
Rubber Works imeni So go Kirov).Voronozhakiy gosudarstvennyy
universitat (Voronezh State University)-
Card 2/4

KRYUCIIKOVA, V,G,j ZAVGORODNIY,_.4a,-
AU71ation of 4,,-cbloroanisole by propylwo, pueudobutylene., and
cyciqUexene in the presence of thk catalyst BFI *HjPO4& Izv&v7a*
ucheb,zav,; khim,i khimotekhe 4 no@2:92-93 61, (MM 14:6)
1. Voronezhakiy gosudaratvennyy univernitotp ka-fodra organicheskoy
khInii.
(Anllnolo) (Alkylation)

B I 10
B203
/
AUTHORS: javgorod.R4f__�.! .. K,_, Sigoval V. I.
TITLE; Synthesis of I-ethYl-4-isopropyl benzene and Some Of its
conversions
PERIODICAL: eniyo Khimiya i
Izvestlya vyashikh uchebnykh zaved
-
khimieheskaya tekhnologiya$ v. 49 no- 1# 1961v 99-101
TEXT; In the alkylation of ethyl benzene with propylene (I) and isopropyl
alcohol (II) in the presence of BF 3 H3POV mainly I-athyl-4-isopropyl
benzene is fo rmed (polyalkyl benzenes 7~o maximum). With M,
l
th
ti
f
i
l
f
d
j
0#2,-0#3 molen mum
o
re
e o
e op
BF H PO are requ
one;
per mo
propy
3' 3
4
yield (69A of .
1
the theory) is obtained with the ratio: 3 moles of ethyl
benzene - I mole of propylene - 0.3-moleil of catalyst. With (II)o
0-5-1 moles of BF 3'H3PO4 are required per mole of ieopropyl alcohol; the
optimum yield (61~o of the theory) is obtained with the ratio; 2 moles of
ethyl benzene 1 mole of isopropyl alcohol I mole of catalyst, and at
Card V55
~tn

3/153/61/004/001/004/009
Synthesis of l.-ethyl-4-isopropyl ... B110/B203
86-900C. Alkylation with propylene and BF 3*H3P04 at the molar ratios
4 : 1 : 0.3 and I . I -. 0.2 proceeds slowly at 53-550C (yield 2Wo of the
theory). At 1000C, the reaction proceeds vigorously, the catalyst being
thrown out of the reaction mixture. 0-5 and more than 2 moles of ethyl
benzene per mole of isopropyl. alcohol gives only 5ry/a of the theoretical
yiel.d. Nitration of i-ethyl-4-isopropyl benzene proceeds readily.
Excess bromine gives pentabromo ethyl benzene. Nitric acid oxidizes to
terophthalic acid. In autooxidation with atmospheric oxygen in the
presence of manganese resinate, cobalt acetate, and calcium hydroxideg
mainly the a-oarbon of the ethyl radical is affected, and the hydroperoxide
,of (%-mothyl-p-isopropyl benzyl is formed. Maximum hydroperoxide con-
oent,ration is attained after 2-4 hr (Fig. 1), then decomposition sets in.
With the use of proper amounts of suitable alkali additions, the authors
obtained UP to 37~ of hydroperoxides in the reaction mass after 20 hr.
Thenj.decomposition by 112804 mainly gives p-ieopropyl phenol. Initial
1 0
substances were: industrial ethyl benzene (boiling point - 135-136-5 C)
20 20
d4 0.6655, nD 1-4950); propylene produce d by dehydration of
:Card 2111"

511531611004100110041009
Synthoeia of 1-etl'YI-4-isoProwl B1IOfB2O3
inopropyl alcohol; and freshly prepared BF 3* If3PO 4# Alkylation was
performed by the mothod earlier described by the first author (Ref. 1:
S. V. Zavgorodniy et. al.; Zh, obehohey khimiij 26f 2180 (1956)).
Results are tabulated. l-Ethyl-4-isopropyl benzene is formed almoot
-exclusively (values obtained: boiling point - 193-194OC;
20 20
d4 . o.8626; n D _ 1-4927' MRD - 49-8; calculated: 49.4; published
0 20 20
data: boiling point - 1-94 C; d 0,8625; nD - 1.4927). The follow-
4
ing derivatives were prepared: (1),Pentabromo ethyl benzene by bromina-
tion with Br2 in the presence of Al chips at 00C (white powder,
MP - 137-138-50C). (2) Mononitro-ethyl ioopropyl benzene (34.5% Yield)
by nitration with mixed acid. Highly viscous liquidp mp - 136-1370C
20 20
at 3 mm Hg; d 4 . 1.0535; d D 1-5338. Found: M - 192.5 C11H 15 N02;
calculated: M - 193.0, Oxidation with HI-103givea nitro-terephLiialic
acid (yellow platelets, mp - 263-2650C (from alcohol)). (3) Terephthalic
acid by prolonged heating with 25~ HNO 3 to weak boilingp identified by
Card 315-

S/ 15 31611004100110041009
Synthoois of I-e-'Whyl-4-isoProPY1 B110/B203
conversion with CH OH and concentrated H
3 2c?04to the dimethyl ester of
terep"Ithalic Etold (mP = 139 1400C). Autooxidation of I-ethyl-4-isopropyl
benzene with atmospheric oxygen proceeded in the prouenoo of mangancee
reninate and alkali additions to a decrease of the hydroperoxide con-
centration in the reaction mass. Tile concentration was iodometrically
determined every 2-4 hr (Fig. 1). On decomposition with H 2soV the
hydroperoxide of any concentration yielded p-isopropyl phenol (long,
white needles, mP~- 57-50C (from potr.)Ieum-other)) besides considerable
amounts of resin. With CH 2CICOOH, p--isopropyl phenoxy acetic acid is
formed (small, whita needles, mp = 600C# publiahed; mp = 8100). Th-re
are 2 fibrures, 1 table, and 5 references: 3 Soviet-bloc and 2 non.
Soviet-bloc. The reference to the Englioli-language publication reads as
follows: C. E. Weloh, G. F. flonniont J. Amer. Chem. Soo.t L, 2603
(1941).
.Card 4/5

3/153/61/004/001/006/009
B11O/D2O3
AIJTHORSt Zavgorodniy# S.V.9 Gonsovskayaq T.B*
TITLEs Benzene alkylation with olefine of ecrubber exhaust gases
in the divinyl produotion by the Lqbedev method
PERIODICALt Izveatiya vysohikh.uohebnykh zavedoniy, Xhimiya. i khimi-
cheskays, tekhnologiyap va 4# no# Ir 19619 128 - 131
TEXTt In contrast to the 'Alkylation of aromatics with individual olefinst
the alkylation-vith olefin mixtures has only been dealt with In the book
by M.I. Dalin (Ref. 91 Alkilirovaniye benzola olefinamip Oookhimizdat,
Mti 1957). It is of special interest since olefin mixtures are obtained
in the chemical industry, e.g., 13-15% of ethylene and propylene in the
scrubber exhaust gas in the divinyl production according to S.V. Lebedev
.during rubber synthesis. They could boused for the produution of large
quantities of valuable for synthesis ethyl and isopropyl benzenes instead
of fuels. Fo'r this purpose, the authors studied the benzons alkylation
with ethylene and propyleno of the scrubber exhaust gas in the presence
of AM 2* H2 PO 49 AlCl3t AlCl2-R304 and BF30H,PO4 Favorable conditions
Card~- 1/y

a/153/61/0O4/OO1/oo6/oo9
Benzene alkylation with ... B110/B203
yiolded a quantitative utilization of olefins (mainly ethylene and isopro-
pylene). Ain is the most efficient catalyst. Optimum ratio benzene/
/olefin/cataly2t - 2-5/l/0-05. Optimum temperature - 76-800c, gas velo-
city - 4-5- 5 lZhr. Heret the yield of isopropyl benzene (I) is 90%, that
of ethyl benzene (11) 70%, referred to propylene or ethylene absorption.
-The fraction of M in the alkylate is 32% , that of (11) 51%. Ethylene
conversion' - 77%, propylene conversion m 89%. The efficiency of AICI 2*
*H2PO4 and LIC12*HSO 4- is worse than that of AM 30 With the use of
BY3 ON3PO 40 benzene was only propylated (Tables I and 2). With 0.05 moles
of AIC12*HSO 4 and Oo10 moles of A1C120H,?O 4 per mole of olefin, the pro-
pylation rate is high up to 35 OCp isopropyl ben2ens being mainly formed#
In the eth7lation, hexaethyl benzene is also formed (8-260 in the alkylate).
Higher amounts or catalyst and increase in temPerature to 50 - BOOG In-
crease the ethyl benzene formatioav and reduce slightly the i9opropyl for-
matio-d. Here, almost no hexastbyl benzene ie formed, Thiophefte-frae ben-
zene was used. After divinyl adsorption with eth 1 alcoholl the scrubber
exhaust gas (3-6 % of the alcohol passing through~ contained 12-15% of
Card 2/y
7777
N