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Патент USA US2408296

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sept. 24, 1946.
s. c. cARNEY
„ _2,408,294 '
Filed Nov. 13,"194'5
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Patented Sept. 21.4, 1946 Y'
Samuel C. Carney, Bartlesville, Okla., assigner to
Phillips Petroleum C ompany, a corporation of
Application November 13, 1943, Serial No. 510,179
9 Claims. (Cl. E60-683.5)
This invention relates to the conversion of hy
drocarbonsinthe presence of a metal halide'cat~
.Y Aluminum chloride reacts with certain hydrocar
bons, which may be present in the feed stream
alyst. This invention .has particular application
vor formedV in the reactor, forming an undesirable
liquid `sludge of low catalytic activity. The sludge
tothe isomerizationof normal parañins >to iso.
paraiiins. The invention relates, _in its ,preferred
modification, to the Yisomerization of normal'bu
tane to isobutane in the presence oían aluminum
tends to form a coating over the solid aluminum
chloride preventing contact with the hydrocar-v
bons. Sludge formationv represents'a loss of
halide catalyst.
Y f .
aluminum chloride catalyst. Replenishing the
aluminum chloride lost by sludge formation. is
Silit> the’ presenttime, conversion of straight
chain v.paraffins to branchedî chain paraliins of l0, costly andthe sludge itselfis a nuisance in that`
it creates a disposal problem.
the. same4 number ofcarbon atoms per> molecule
` is .assuming increasing importance iin. petroleum
"The idealV solid `catalyst is onejwhich Will’re-v
refining operations. The isomerization yof the
normal paraflins to .isoparaflinsfA is carried out
,commerciallyuwith varying` :degrees of success.
lmain in solid form-under the conditions at which Y
Aluminum halides, ‘particularly’ aluminum chlo
the y.catalyzed reaction takes place so that feed ma
teria] may >be passed> in either liquid or> vapor
phase Lover an extended surface of vthe catalyst.
ride, are among the mostV promising catalysts- for
these reactions. In carryingout isomerization of
paraflins in the presence' of aluminum vchloride
'lî‘lfleldeall catalyst should be selective in itsac
tion, promoting only the desired reaction, and
should not react with eitherthe' feed stream or
the parafñns are> contactedinl liquid or` vapor 20 the reaction products. 'From a consideration of
phase vwith aluminumv chloride> inthe presence
thefphysiclal, chemical,> andcatalytic yproperties
of hydrogen chloride as a promoter.
oflaluminum chloride,v itis evident that. it is far
yfrom ideal as a lsolid -catalyst in spite of its vhigh
practice is to use the aluminum chloride insolid
form, usually _admixed with »or Adeposited* on a
suitable carrier material.Y „Carrier materials may
catalytic activity. '
As` mightY be expected, many attempts .have
been `.made to devise ay mechanical system for
be coated with aluminum chloride by mechani
cal mixing, by fusion of. the aluminum chloride
carrying out the isomerization processwith alu
with the carrier, by ¿impregnating the: carrier un
minum chloride whichV would take into consider
ation the undesirable physical and chemical
der pressure with. molten aluminum chloride, and
by sublimation oftaluminum chloride‘onto» the
properties of this catalyst.
Alternatively, the .aluminum vchloride
[Generally speaking, catalytic operations may
may ber-used in finely divided 'formrsuspended
be'cla‘s'siñed inthe following groups with respect
inA an inert liquid; in liquid phase, particularly
to the'phaserelationship of catalyst and react
in vtheform of the double salt o_f- aluminum chlo
ride with other metal chlorides; orein -the vapor 35
..1-.y Catalyst and> feed in a single liquid phase.
Vv2. Catalyst and feed both in vapor phase.
I3. ACatalyst in solid. phase, feed in liquid or va
Although aluminum chloride is a well known
catalyst for a widevariety of reactions other than
por phase.-
4. Catalyst in liquid'phaSe, either as such or in
ing catalyst'certain problems of operation re-` 40. solution; Yfeed in vapor phase or in a second liquid
isomerization, and has long been used as a crack- '
sulting from Vthe physical and chemical proper
v5. Catalyst in vapor phase, feed in liquid phase.
ties'of aluminum chloride have never been` Vsatis- .
factorily, solved.> Aluminum vchloride hasgslight,
VIn groups l and 2 the catalyst and >reactants
but definite, solubility in hydrocarbons., It also
possesses VAsubstantial -volatility at the tempera~
.tures required'fcr hydrocarbon conversion. Due
arev inV the. mostv intimateV contact. Operations
falling Within either groups land 2 >present
desirable operating conditions vbecause of the
nature of the „contact between the Acatalyst and
to the solubility in hydrocarbons'some aluminum `_
chloride is carried out of -the reactor 'inY liquid
‘the reactants; - Processes of the typey classed in
grouppl depend for operation upon complete» mis
The volatility orv vapor. pressure of
the reaction zone.. Solid aluminum'chloride
cibilìty ofcatalyst and reactants. Since vapors
are fully miscible, operation of a process inv ac
cordance with _group 2 may generally ybe more
tends to soften .and run together thereby reduc-l
readily practiced.
aluminum chloride; at` conversion Atemperatures
results in contaminationcf vaporouseffluents.> of
ing thelarea of_» surface available and
clogging -passages ¿betxveenîthe catalyst supports.'
. l
ÈYIfhe process of the present inventionis prefer
55 2lb1y«çarried out in Voperation with catalyst and
sorber C are parts o'fthe same column as illus
trated and described herein. It will be evident
to those skilled in the art that these Zones may
bon vapors and hydrogen chloride as promoter.
The reaction then takes place in vapor phase.
The aluminum chloride vapor is separated from
the hydrocarbon >vapor by absorption with .anti
mony trichloride. Aluminum chloride vapors are
be separated orotherwise arranged While still
maintaining the functions of these elements as
subsequently regenerated by heating the aluminum chloride-antimony trichloride mixture which
effects vaporization of aluminum chloride therefrom. The antimony trichloride, in turn,A .is re
used for absorption of aluminum chloride va
pors. ’The mutual solubility of aluminum chlo
ride and antimony trichloride is known'. It is also
described herein. Each of sections A, B, and C
isof suitable size to eiîect the desired operation,
10 section B being generally larger than sections A
or C to provide the necessary residence time re
quired to allow the reaction to take place to the
,l desired extent. -
Hydrocarbon `feed, normal butane for isomeri
15 zation to isobutane', enters through line 2. The
major portion of the feed passes to heater 3
known that antimony trichloride acts as appro
moter for aluminum chloride in iscmerlzation
of parañins. The present invention utilizes anti--` »
mony trichloride in hydrocarbon conversion re
actions in a new and useful manner.
drocarbon vapors. In the preferred modiñcation
of this invention the still A, reactor B, and ab
hydrocarbons in the vapor phase. When oper
ated in this manner the aluminum chloride cat
alyst is Vaporized and adrnixed with hydrocar
wherein the'nor'mal butane is heated to the op
erating temperature, and from which the vapors
may be passed through valve 4 into the reaction
20 sectìonB or through valve 5 _to the distributor 6
in the lower part of the still A. The normal bu.
tane thus introduced contacts vapors of alumi
num chloride and hydrogen chloride in vapor
ants in vapor phase are:
phase in the reactor where isomerization of nor
1. Solid aluminum chloride with its attendant
25 mal butane to isobutane takes place.
disadvantages is not present in the reactor.
The temperature in the reaction zone is above
2. Perfect contact of catalyst and hydrocarbon
the vaporization temperatureof aluminum chlo
While both are in Vapor phase is attained in the
ride and below the temperature at which u_nde
sirable reactions take place. Aluminum chloride
3. Coating of catalyst with sludge is elimi
sublimes at a temperature of about 178° C'. and
has a boiling point of about 183° C. at atmos
` 4. The process may be operated continuously
pheric pressure; At 21/2 atmospheres pressure
without necessity of interruptions to replace cat
The advantages of operating in accordance with
the present invention with catalyst and react
the boiling point of aluminum chloride is about
190° C. Accordingly, the temperature in the re
An object of this invention is to provide „an im
action'chamber maybe within about 190° C. _to
about 250° C. Preferably the temperature with
proved process for the conversion of hydrocar
bons in the presence of a metal halide catalyst. .
in the reactor is coniined within the limits of
about` 190° C. to about 220° C. The isomeriza
tion of normal .butane to isobutane is exothermic,
mal paraffins to isoparaflins.
Still another object of this invention is to pro 40 hence there is a tendency for the temperature to
increase from the bottom to the top of section B.
vide such a process wherein parafñns are isomer
The temperature in section B may be controlled
ized in the presence of a metallic halide catalyst
by injection of normal butane at one or more
wherein the catalyst and reactants are in Vapor
points along the length of the reaction chamber.
The temperature at the top of the reaction cham
A further object of this invention is to provide
ber B is limited to a value below about 200° C.
an improved process for the vapor phase isom
by the addition of fresh normal butane, prefer
erization of normal butane to isobutane inthe I
Another object of this invention is to provide
an improved process for the isomerization of nor
presence of vaporous aluminum chloride as a cat
A still further object of this invention is to pro
vide a process for the separation of aluminum
chloride vapors from hydrocarbon vapors byfab
sorption with antimony trichloride.
Further objects and advantages of this inven
tion will be evident from the following detailed
description of specific applications of the inven
tion and the accompanying drawing illustrating
diagrammatically the described specific embodi
Figure 1 illustrates diagrammatically appa
ratus suitable for carrying out paraflin isomeriza
ably in liquid form to take advantage of the heat
of vaporization. For this purpose, a part of the
normal butane from line `l is passed through line
1 to a distributor 8 _in the reaction chamber B.
Vapors from the reaction chamber, comprising
chloride, ' aluminum
chloride, and antimony trichloride vapors, pass
through the chimney 9 into the absorber C. The
absorberC is provided with vapor-liquid contact
means, as,` for example, packing or bubble plates.
In the absorber the> vapors from the reaction
chamber are brought into contact with liquid an
60 timony trichloride.
The temperature in the ab
sorption section is preferably within the range of
180° C. to about 200° C. The antimony trichlo
tion by the process of this invention.
` '
ride absorbs aluminum chloride vapors from the
Figure 2 illustrates diagrammatically appa
hydrocarbon stream. The mixture of aluminum
ratus suitable for a more general application` of
the process of the present invention to hydrocar 65 chloride and antimony trichloride hows from the
absorber C through the downspout I0 to the va
bon conversion.
porizer or still A. Still A preferably is provided
' With reference to Fig. 1 of the drawing, the
with plates or packing providing vapor-liquid
numeral l designates a column of suitable size
means similar ot that of the absorber.
divided into three sections, A, B, and C. section
Heat is supplied to the still by suitable heating
A constitutes a still in which aluminum chloride
means, e. g., steam coil. In the still the alumi
is vaporized.l Section B is the reaction chamber
in which reaction of the hydrocarbon takes place
num ychloride is _liberated from the antimony tri
chloride and passes up into the reactor B. The
in vapor phase in the presence of aluminum chlo
hydrocarbon vapor'supplied tothe still from the
ride vapors. Section C is an absorber in> which
aluminum chloride vapors are separated frornhy 75 distributor 6 aids in the vaporization of the alu
6 .
min'um 'chlorideby its 'stripping action.v audits
eiïecton .thel partial’npressures in the still., The
7 num` `chloride ,; Sludge which may be; formed in
temperature in the stillV is maintained within the
Vaporized aluminum chloride'enters theN reactor
through line 45 as. will be evident- from the fol
range ofxabout 180° C..toV about'220° C'.
Liquid .antimony trichloride is.v drawn from the
stilland passed by‘pump l2 to the cooler I3;V The
coolerylâ may conveniently be cooled by boi-ling
water'to` obtain a temperature approaching 100°
C. -In any case the antimony trichloride isnot
cooled below about 80° C. since-it solidiiies at '1 31.4°
C. The cooled antimony _trichloride isi ythen
passed through line I4 to the upper part of the
absorber C> for further absorption of` aluminum
chloride vapors, thereby'completing its cycle. A
part of the stream from theabsorber Cfmay be
passed via line l5 to a-catalyst make-,up chamber
l5. Inchamber I6 fresh aluminum .chloride is
the'reactor, :maybe withdrawnithrough line 44.
lowing description of_ operation. The hydrocar
bons leave the reactor in vapor phase through line
4S at a temperature above about75° C. and are
cooled, if necessary, to a temperature belowabout
200°fC. before entering the absorber 41.
temperature inf reactorliß` may be any' tempera
ture necessary for carrying out the reaction. The
isomerization of normal parañins to isoparaiiîns
may be conductedat temperatures in the range
. of Aabout 50° C. to about 250° C.; cracking', gener
ally at temperatures above about 250° C. It willbe
recognized by thosek skilled in the art» thatV the
composition of the feed and other operating» con
ditions` aiîect the reaction and govern the tem'
antimonyl trichloride from the absorber to the
perature at which a given reaction'is> best' carried
still A through line I1.
20 out. The temperature in the reactor is immate
The hydrocarbonvapors, lfreed from alumi
rial to the operation of this modification of the
num chloride vapors, leave the column by line 20
present invention, it being essential only that
and passito the condenser 2| ; g Condensate is col
the temperature of the vapors entering the ab
lected` inA the accumulator.k 22 and fed via line` 24
sorber d1 be within. the range of about '15° C.
to the fractionator 25. The fractionator 25 is
to about 200° C.
provided with suitable refluxing and reboiling
In the absorber 41, the hydrocarbon vapors
added, as needed, and-_passes in solution in the
Hydrogen chloride is
containing vaporous aluminum chloride are con
separated from' the hydrocarbons and returned
to ¿column I via line 2,0. Additional hydrogen
chloride may be supplied as needed »through line
21. Fromvfractionator 25, thev hydrocarbons are
means as is customary.
tacted with liquid antimony trichloride which ef
passed through line-_2,8 to. the fractionator 29 in
fects solution ofthe aluminum chloride vapors.
Fresh antimony trichloride may be added tothe
absorber- and saturated antimony trichloride, re
„ moved from theY absorberasî required, e. g.,„«in
Which'the-isobutane is lseparated from unreacted t
the V,manner described in‘connection'with Fig. 1 by _
j normalbutane. ¿The isobutane passes overhead
means of, lines 63 and 64, respectively. Thefab
throughline 30; normal butane is returned 35 sorbed. aluminum’chloride is subsequently vapor
throughfline 3f! to the‘heater 3- as
ize'd from the. antimony> trichloride Iin the vapor
conversion ¿to isobutane.
The foregoing detailed description is speciñc to Y
the isomerization of normal-butane _to isobutane
izer 48 and returned to the reactor 40. through
line 45. The vaporizer 48 is provided with heat
ing means 49 and means 50 for admitting strip
, in the presence of aluminum chloride as catalyst 40 ping vapor .thereto to >'effect Vaporization of alumi
using hydrogen chloride as promoter for the reac
tion. Itis to be understood that inthe process
of the present invention, normal parafûns other
than butane may be employed as feed tothe
isomerization reaction. The aluminum chloride
is promoted by a hydrogen halide, generally hy
drogen chloride is employed because of its avail
ability. It is well knownrthat other metal halides
numchloride. It will be evident to rone skilled
inthe art that the.. absorber and vaporizer may
be so constructed asto be interchangeable, each
serving alternately asfabsorber and vaporizer.
Hydrocarbon vapors freed of aluminum chlo
rideare passed from the absorber 41 to the con
denser 52. Condensate from the condenser col
lects in accumulator 54 from which it is passed
catalyze the isomeriaationreaction and that these
tothe fractionator' 55. `The promoter is'separated
catalysts may be promoted by hydrogen halides. 50 from thehydrocarbons and returned to the reac
Aluminum bromide is known to be a goodrisomer
tor through -line 51; additional promoter may
ization catalyst which may befpromotedby hydro
be added as requiredthrough-line 58. The hydro
gen bromide. It is also known to use mixtures
of _aluminum chloride and aluminum bromide as
carbons are passed fromthe fractionator. 56 to a
second fractionator 60 for separation of product
catalysts for this reaction.
55 from unreactedhydrocarbons. The desired prod
`-Figure 2 of the drawing illustrates inra more
uct leaves the fractionator by line 6|; unreacted
generalwa-y the application of the ¿present inven
hydrocarbons kare returned to the reactor 40
tion to hydrocarbon conversion processes in which
through line 62.
an aluminum chloride catalyst is used. Cracking,
Antimony trichloride is liquid at atmospheric
isomerization, orother-reaction promoted by alu 60 pressure at temperatures within the range of
minum chloride may be carried out in the appa
about-'14° C. to about 220° C, This liquid is readily
ratus illustrated. >Reaction takes place inthe
transferred from point to- point in the system.
reactor 4u in the presence of aluminum chloride
- While; aluminum chloride is solid atV tempera
as catalyst and~hydrogen»_ chloride as promoter.
below aboutg180°` C; it should be noted that
The ,aluminum chlorideis preferably present in 65
it has va definite vapor pressure at temperatures
the reactor in vapor phase; it Will be evident,
however, thatV aluminum chloride maybe present ` below'its melting point. The vapor pressuresV of
in the reactor Ain liquid or .vaporr phaseL The
aluminum chloridel atv various temperatures are
approximately as follows :`
hydrocarbon feed enters the reactor through line42. A suitable coolant, preferably hydrocarbons, 70
, t
may Vbe added to the reactor through line 43 as
Aadmitted through line 42 or line_43 if desired.
Liquid hydrocarbons, togetherwith `any- a1umi‘-`
desired. The aluminum chloride is charged to Y(
thereactor in any convenient manner; it may be
'Mm. Hg
C __________________________________ _„
C-, ________________________________ _,
C; _________________________________ __
C ___________________________________ _. 234
_. 513
2,408, 294
Witli‘ molten antimony trichloridein an absorbing
In view of the fact that‘hydrocarbon vapors are
present in large quantities in the reactor, it
zone and thereby .dissolving aluminum chloride
from said mixture -in said >molten antimony trl
chloride while allowing the resulting vaporous
will be readily appreciated that large quantities
of aluminum chloride vapors appear in the hydro
carbon vapors even When using solid aluminum
mixture of unconverted normal parañîn, isopar
chloride at temperatures below the vaporization
temperature. The present invention has Wide ap
añ'in and hydrogen halide to pass through undis
solved, passing the resulting solution of aluminum
chloride in antimony trichloride to a stripping
plication in the removal of aluminum chloride
zone and there stripping the dissolved aluminum
vapors from hydrocarbon vapors in the eiliuents
of hydrocarbon conversion processes in which alu 10 chloride in> vaporous form therefrom, and pass
ing the resulting vaporous aluminum chloride into
minum chloride is used as catalyst.
said reaction zone.
I claim:
6.' A process for the vapor-phase isomerization
1. A process for the conversion of hydrocarbons
of normal parañins to isoparafñns in the presence
in . a reaction catalyzed by aluminum chloride
which comprises contacting the` hydrocarbon With 15 of aluminum chloride which comprises contacting
vapors of a normal paraiiin with aluminum chlo
aluminum chloride in a reaction zone under con
ride vapors in the presence of hydrogen chloride
ditions such that the desired reaction is effected,
at a temperature within the range of about 190° C.
passing vaporous eiiluent from the reaction zone
to about 250° C. in a reaction zone in the absence
containing hydrocarbon vapors and aluminum
chloride vapors into contact with liquid antimony 20 of liquid phase; passing vaporous eilluent of said
reaction zone containing vapors of aluminum
trichloride effecting separation of aluminum chlon
chloride, hydrogen chloride, normal parañin and
ride vapors from the hydrocarbon vapors by solu
isoparaflin into intimate contact with molten an
tion in liquid antimony trichloride, subsequently
timony trichloride at a temperature Within the
liberating aluminum chloride vapors from liquid
range of about 180° C. to about 200° C. in an ab
antimony trichloride, and returning the aluminum
sorption zone thereby dissolving aluminum chlo
chloride to the reaction zone as catalyst.
ride from said vapors while allowing the hydro
2. In a process for conversion of hydrocarbons
gen chloride, normal paraffin and isoparafûn va
in a reaction catalyzed by aluminum chloride, the
pors to pass through undissolved’; passing the re
> improvementY which comprises contacting va
sulting solution of aluminum chloride in anti
porous` eiliuents of the reaction containing alumi 30 mony trichloride to a distillation zone and liber
num chloride vapors in admixture with hydro
ating the aluminum chloride from the antimony
carbon vapors With liquid antimony trichloride
trichloride in said zone at a temperature Within
eiîecting separation of aluminum chloride vapors
the range of about 180° C. to about 220° C. in the
from the hydrocarbon vapors by solution in liquid
35 presence of hydrocarbon vapors as stripping me
antimony trichloride, and subsequently liberating
dium; and passing aluminumv chloride vapors
aluminum chloride vapors from liquid antimony
from the distillation zone to said reaction zone.
7. The process of claim 6 in which said normal
’ 3. In a process for the conversion of hydrocar
paraffin is normal butane and said isoparafl‘ln is
bons in a reaction catalyzed by aluminum chlo 40 isobutane.
ride, the improvement which consists in contact
8. A process for isomerization of normal par
ing vaporous eñ‘luents of the reaction containing
ailins to isoparafûns which comprises contacting
aluminum chloride vapors and hydrocarbon va
said normal' paraiñn with aluminum chloride in
pors With liquid antimony trichloride effecting
a reaction zone in the presence of hydrogen halide
separation of aluminum chloride vapors from the
and at a temperature within the range of'about
hydrocarbon vapors by solution in liquid antimony
50° C. to about 250° C. effecting isomerization of
normal paraffin to isoparafûn, passing vaporous
4. A process for the conversion of hydrocarbons
eflluent of said reaction zone to an absorption
in a reaction catalyzed by aluminum chloride
zone into intimate contact with liquid antimony
which comprises contacting the hydrocarbons 50 trichloride at a temperature Within the range of
with aluminum chloride in a reaction zone, pass
ing vaporous eiiluent from the reaction zone con
about ’75° C. to about 200° C. effecting selective
solution of aluminum chloride vapors contained
therein, passing the solution of aluminum chlo
ride in antimony trichloride to a distillation zone
and vaporizing aluminum chloride from antimony
taining aluminum chloride vapors to an absorp
tion zone into contact with liquid antimony tri
chloride at a temperature in the range of about
75° C. to about 200° C. effecting removal of alu
trichloride in said zone at a temperature in the
minum chloride from said hydrocarbon vapors
by solution in liquid antimony trichloride, passing
antimony trichloride containing aluminum chlo
ridein solution therein from the absorption zone
to a distillation zone, liberating aluminum chlo
ride from antimony trichloride in the distillation
zone by heating to a temperature within the range
range of about 180° C. to about 220° C.; and pass
ing aluminum chloride thus liberated in the dis
tillation zone to the reaction zone.
9. A process for the vapor-phase isomerization
of normal butane to isobutane which comprises
passing vaporous-normal butane into a body of
to the corresponding isoparafñn Which comprises
liquid antimony trichloride having aluminum
chloride dissolved therein and maintained at a
temperature adequate to vaporize said aluminum
chloride therefrom, passing resulting vapors of
normal butane and aluminum chloride upwardly
intimately contacting the normal paraffin in va
por phase with volatilized aluminum chloride
posed above said body of liquid and maintained at
of ‘about 180° C. to about 220° CL, and passing the
liberated aluminum chloride vapors from the dis
tillation zone to the reaction zone.
5. The process of isomerizing a normal paraffin
into and through a separate reaction zone dis
as a catalyst in the presence of an anhydrous 70 isomerization conditions of temperature and pres
sure and substantiallyfree from liquid phase, said
reaction zone being of sufñcient size to eiîect sub
stantial vapor-phase isomerization therein, pass
of time such as to effect isomerization to the iso
ing resulting vapors of normal butane, isobutane
paraiììn, removing the resulting mixture in vapor
state from said reaction zone and scrubbing it 75 and aluminum chloride upwardly into and through
hydrogen halide promoter in a reaction zonesub-V
stantially free from ‘liquid phase and for a period
a separate scrubbing zone disposed above said re
action zone, contacting the last-mentioned vapors
in said scrubbing zone with liquid antimony tri
ohloride to dissolve substantially all of the A1013
from said vapors, recovering from said scrubbing
zone vapors comprising isobutane substantially
free from aluminum chloride, ñowing resulting
solution of aluminum chloride in liquid antimony
trichloride by gravity to said body of liquid anti
mony trichloride through a- path separate from
Y said reaction> zone, and passing liquid antimony
trichloride from said body of liquid antimony
trichloride to said scrubbing zone for use therein ,
to dissolve aluminum chloride from normal bu
tane and isobutane vapors.
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