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Patentecl Oct. 29, 1946
‘2,410,071
UNITED STATES PATENT OFFICE
2,410,071
.
CATALYTIC ALKYLATION PROCESS
Aaron W. Horton, Detroit, Mich., and John W.
Brooks, Wenonah, and Arlie A. O’Kelly, Wood
bury, N. J., assignors to Socony-Vacuum Oil
Company, Incorporated, a corporation of New
York
No Drawing. Application September 17, 1943,
Serial No. 502,812
14 Claims.
1
(Cl. 260-6834)
2
,
This invention relates to the alkylation of
tures and pressures, on the order of over 900° F.
and over 4000 pounds per square inch gauge,
respectively; or may be conducted in the presence
para?inic hydrocarbons with ole?nic hydro
carbons and is more particularly concerned with
' -the production of high octane motor fuel by the
of alkylation catalysts at lower temperatures
and pressures, thereby assuring a high yield ofv
catalytic alkylation of para?inic hydrocarbons
desired alkylate by avoiding extensive degrada
with ole?nic hydrocarbons.
It is well known in the art to polymerize ole
tion of the reactants, the occurrence of side and
secondary reactions, and appreciable polymeriza
, ?nic hydrocarbon gases to produce motor fuels
having constituents of an, unsaturated character.
tion of the ole?nic reactant. The two methods
Various commercial processes have been proposed 10 are known as thermal alkylation and as catalytic
alkylation, respectively.
for ultimately eifecting the desired polymeriza
tion of the ole?nic hydrocarbons. These processes
have been predicated upon the dictates of the
chemical nature of the stocks available as well
Several methods are known for the catalytic
alkylation of isoparai?nic hydrocarbons with
ole?nic hydrocarbons. For instance, it is known
as engineering considerations such as initial and ,15 to alkylate isopara?inic hydrocarbons with ole
?nic hydrocarbons in the presence of sulfuric
operation costs; their essential feature being that
acid, phosphoric acid, metal phosphates, metal
in the course of treating the materials, the ole?nic
hydrocarbons produced in the earlier stages of
halides, activated clays and the like, as catalysts.
In these catalytic alkylation processes, the hydro
the process, are eventually polymerized to gaso
line. Accordingly, hydrocarbon gases may be ,20 carbon reactants form with the alkylation cata
passed along with cracking stock or naphtha ‘ ' “ lysts, a heterogeneous system during the alkyla
through a cracking still to crack and polymerize
such gases to gasoline simultaneously with the
cracking or reforming, or paraf?nic hydrocarbon
gases may be separately cracked to ole?nic hy
drocarbon gases and these gases are subsequently
tion operation. Since under alkylation condi
tions, the catalytic activity of the alkylation cata
:25
passed with naphtha through a polymerizing and
reforming still. In some instances, the processes
involves the use of catalysts for facilitating the
lysts appears to be predicated upon contact be-v
tween the catalysts and the gaseous hydrocarbon
reactants at the interfaces therebetween, in these
processes, the catalysts are used in amounts vary
ing between 10% and 200% by weight, on the
charge. depending on the catalyst used. Due to
30 these comparatively high amounts, where pos
cracking and/or polymerization operations.
sible, recovery and regeneration of the catalysts
It is also well known in the art, to combine
para?inic hydrocarbons directly with ole?nic
have been proposed. This, of course, involves
hydrocarbons by processes broadly called alkyla
high initial and operation costs. Further, it is
also known that certain substances called pro
tion processes, to produce motor fuels having
constituents of saturated character. In alkyla— 35 moters,_-promote the catalytic action of these
tion processes, a charge comprising a mixture of ‘
alkylation catalysts. Accordingly, several proc
a paraf?nic hydrocarbon, called the paraf?nic re
actant, and an. ole?nic hydrocarbon, called the
ole?nic reactant, is subjected to high tempera
ture and pressure to produce a saturated alkylate 40
product. Since conditions of alkylation also
cause polymerization of the ole?nic reactant,
esses have been proposed wherein small amounts
of these promoters, on the order of about 1% to
it is necessary to maintain a relatively low con
3% by weight on the charge, are added to the
catalysts to promote their alkylation catalytic
activity.
'
A copending application, Ser. No. 502,018, ?led
/ September 11, 1943, in which one of the inventors
of the present application is coinventor, is directed
centration of the ole?nic reactant in the charge.
The only limit to the'pressure used appears to 45 to the process of alkylating parai?nic and iso
para?inic hydrocarbons with ole?nic hydro
carbons, which comprises contacting a para?inic
On the other hand, the temperature used is
or isoparaf?nic hydrocarbon and an ole?nic hy
limited by degradation of the hydrocarbon reac
drocarbon in a‘ reaction zone under alkylating
tants in the charge to low molecular weight hydro
carbons and the occurrence of side reactions, 50 conditions, with small or promoter amounts of
what has been termed therein, a homogeneous
including polymerization of the ole?nic reactant,
gaseous phase alkylation catalyst consisting es
under high temperature conditions, that sub
sentially of a material that forms with the hydro
stantially reduce the purity of the product ob
carbon reactants, a single homogeneous gaseous
alkylation may be conducted at high tempera 55 phase under the alkylation conditions of the reac
be the feasibility of maintaining high pressures. ‘
tained.
.
p
,
'
£410,071‘
4
3
have octane numbers of 89 and 82, respectively,
the importance of the alkylation of isobutane
with propylene in the presence of homogeneous
gaseous phase catalysts under alkylation condi
tions that favor the production of triptane is
manifest. We also found that in actual practice,
it was impossible to obtain triptane exclusively,
appreciable amounts of 2,2-dimethylpentane and
Z-methylhexane being always formed.
The specific classes of homogeneous gaseous
tion zone. The alkylation conditions of the
process of this copending application comprise a
broad temperature range of about 590° F. to about
850° F., preferably, about 650° F. to about 825° F.:
and pressures of at least 500 pounds per square
inch gauge, preferably, at least 1500 pounds per
square inch gauge.
Another copen-ding application, Ser. No. 5G2,-v
813, ?led September 17, 1943, in which the in
ventors of the present application are coinven
tors, is directed to the process of alkylating iso
butane with propylene, which comprises contactf
ing isobutane with propylene in a reaction zone
under closely controlled alkylating conditions,
with promoter or small amounts of the homo
geneous gaseous phase catalysts broadly dis
phase catalysts claimed in the above-noted co~
pending applications are organic halides, and,
more particularly, organic chlorides and organic
bromides.
We have found that elemental halogens are
15
suitable homogeneous gaseous phase alkylation
catalysts and that isoparaillnic and paraliinic
closed in the copending application referred
to
hereinabove, the
closely
controlled ' alky
' hydrocarbons may be e?iciently alkylated with
ole?nic hydrocarbons to produce high yields of
lating conditions including a temperature range
of about 750° F, to about 850° F., preferably, 20 high octane gasoline by using small 01' promoter
amounts of elemental halogens to form with the
about 775° F. to about 825° F., and pres
hydrocarbon reactants, a single homogeneous
sures of at least 2500 pounds per square inch
gaseous phase during the alkylation operation.
gauge. In the alkylation of isobutane with pro
We have also found that elemental halogens are
pylene in the presence of homogeneous gaseous
phase catalysts, we found that the alkylate ob 25 suitable
the catalytic
homogeneous
alkylation
gaseous
of isobutane
phase catalysts
with pro
tained included constituents that are entirely
pylene under the controlled conditions of alkyl
different from the constituents of the hydrocar
ation described in our copending application Ser.
bon alkylate obtained in the alkylation of isobu
No. 502,813, ?led September 1'7, 1943.
tane with propylene in the presence of known
heterogeneous alkylation catalysts, i. e., AlCls, 30 It is an object of the present invention to pro
vide an efficient process for catalytically alkylat
H2SO‘4, and the like. Thus when heterogeneous
ing isoparaf?nic or paraf?nic hydrocarbons with
alkylation catalysts are used, 2,3-dimethylpen
ole?nic hydrocarbons. Another object of the
tame and 2,4-dimethylpentane are important con
present invention is to provide an e?lcient process
stituents of the hydrocarbon alkylate obtained.
On the other hand, in our process, triptane or 35 for catalytically alkylating either normal paraf
?nic hydrocarbons or isoparai?nic hydrocarbons
2,2,3-trimethylbutane, 2,2-dimethylpentane, and
with cle?nic hydrocarbons to produce high yields
Z-methylhexane are the predominant constitu
of high octane gasoline. A more speci?c object
ents of the hydrocarbon alkylate. In our co
is to provide a process for catalytically alkylating
pending application, we postulated the formation
of these three compounds as follows:
40 isobutane with propylene to produce high yields
of high octane gasoline. A. very important object
of the present invention is to afford a process
Isobutane Propylene
CH3
H
capable of carrying out the above objects by using
small or promoter amounts of elemental halogens
that form with the hydrocarbon reactants, a sin
gle homogeneous gaseous phase during the alky
lation operation. Other objects and advantages
of the present invention will become apparent to
those skilled in the art from the following de
50
scription.
.
Broadly stated, our invention provides a proc
ess for alkylating paraf?nic or isopara?inic hy
drocarbons, particularly isobutane, with ole?nic
hydrocarbons, particularly propylene, which com
55 prises contacting the para?inic and ole?nic hy
drocarbons in gaseous phase and in a reaction
zone under alkylating conditions,»with small or
promoter amounts of alkylation catalyst consist
From a motor fuel standpoint, the 2,2-dimethyl
ing essentially of elemental halogens, particu
pentane produced by the first reaction, has any
octane number of about 80 C. F. R. motor method; 60 larly chlorine and bromine, that forms with the
hydrocarbons reactants, a single homogeneous
the triptane produced by‘the second reactionhas
an octane number of well over 100 and'the 2
methylhexane obtained in the third reaction has
gaseous phase under the alkylation conditions of
the reaction zone.
An important feature of the process of the
an octane number of about 45. In view of the
foregoing, in the manufacture of high octane 65 present invention is the fact that, contrary to
the known catalytic alkylation process of the prior
motor fuel by the alkylation of isobutane with
art which are only capable of alkylating isoparaf
propylene, alkylation conditions that favor the
?nic hydrocarbons, our process is capable of al
production of triptane obviously are preferable.
kylating either normal paraftinic or isoparaf?nic
Further, since neohexane which may be produced
by the alkylation of isobutane with ethylene, has 70 hydrocarbons with substantially equal ease.
Another important feature of the process of
an octane number of 93.4, and since 2,3-dimethyl
the present invention is the relatively low tem
pentane and ZA-dimethylpentane which are the
perature that may be used. As a result, degra
predominant constituents of the alkylate obtained
dation of the hydrocarbon reactants in the charge
in the alkylation of isobutane with propylene in
the presence of heterogeneous alkylation catalysts 75 to low molecular weight‘hydrocarbons and the
2,41 0,07 1
6
numbers, respectively, the advantages of ‘employ
pronounced occurrence of side reactions includ
ing polymerization of the ole?nic hydrocarbons
ing bromine as the homogeneous gaseous phase
alkylation catalyst for the‘ manufacture of high
octane motor‘fuel by our process are ‘manifest.
are substantially completely avoided. Conse
quently, in our process, we obtain high yields of
By‘ way of illustrative example, it is possible‘sto
obtain a fraction by our process, containing 10
parts of triptane, 85 parts of 2,2-dimethylpentane
and only 5 parts of Z-methylhexane. This frac
a high grade product that is almost entirely paraf
?nic in nature and is substantially free from
impurities.
,
.
A very important feature of the present in
tion‘ is considerably larger per pass when bro
vention is the fact that, contrary to known cata
lytic processes of the prior art in which the hy 10 mine is used as the catalyst, than when chlorine
is employed. The overall per pass yield of triptane
drocarbon reactants being processedform with
is thus slightly increased While the overall per
the alkylation catalysts, a heterogeneous system
pass yield of 2,2-dimethylpentane is increased ap
during the alkylation operation‘, the alkylatlon
preciably. Therefore, even though the yield of
process of our invention employs alkylation cata
lysts consisting essentially of materials that form 15 triptane is .only slightly increased, it still seems
favorable to produce 80 octane 2,2-dimethylpen
with the hydrocarbon reactants being processed,
tane at the expense of 45 octane 2-methylhexane.
a single homogeneous gaseous phase under alky
The amount of halogen used in our process
lating conditions. The alkylation catalysts of the
varies between about 0.5% and about 3%,and
present invention may be called therefore, homo
geneous phase catalysts in .contradistinction ‘to 20 preferably, between about 1% and about 1.25%,
with respect to the total charge of hydrocarbon
the alkylation catalysts of the prior artwhich
may be referred to as heterogeneous catalysts.
reactants. It must be noted, however, that larger
amounts of halogen may be employed if desired,
Accordingly, as a resultlof the catalyst’s being
although no additional advantages result there
in the same phase or state as the hydrocarbon
reactants being processed. fouling of the catalyst 25
from.
is substantially "eliminated andagitation and/or
,,
~
.
The parai?nic .and'ole?nic hydrocarbons to be
used in our process may be derived from any suit
mixing problems are non-extant. Further, since
the catalytic activity of alkylation catalysts ap
able source, as is well known in the art, and may
pears to be predicated somewhatfupon contact
be used either in the pure state or in admixture
between the catalysts and the gaseous hydrocar 30 with other constituents not undesirable' The
paraf?nic and ole?nie-hydrocarbons usually em
bon reactants at the interfaces therebetween, it
follows that the catalytic ef?ciency of a given
ployed in the preferred operation of manufac
catalyst increases with the increase in area of
turing motor fuels will be the normally gaseous
interfacial contact, other variables remaining
paraf?m'c hydrocarbons‘, except methane and
constant. Hence, since the homogeneous cata 35 ethane, and the normally gaseous ole?nic hydro
lysts of .our process inherently furnish the great
carbons, as is wel1 ‘understood in the art.‘ Here
est possible “interfacial contact” between the
again our .process has ‘a distinct advantage over
catalysts and thevhydrocarbon reactants. under
many of the prior .art processes in that the ole
the conditions of alkylation, e?icient catalytic
?n ethylenelmay be used for alkylating the paraf
activity with a concomitant'high yieldof high 40 ?nic hydrocarbons.- It is well known that eth
grade alkylate is achieved vusing relativelysmall
ylene cannot be used-in many catalytic processes,
amounts of homogeneous gaseous phase catalyst.
including the sulfuric acid process, whereby the
In View of’ the foregoing, an operation feature
of the process of the present invention that is of
supply of available ole?nic hydrocarbons is re
stricted. “Therefore, an important aspect ,of the
considerable practical importance is that small 45 present invention is .the fact that butane, for
or- promoter amounts of elemental halogens are
instance, may be alkylated with ethylene.
used- as alkylation catalysts. These amounts are
A conventional and preferred source of paraf
so small'that they may be discarded feasibly,
?nic and ole?nic hydrocarbons is the ?xed gases
thereby; obviating. recovery and regeneration
obtained around petroleum re?neries.
problems and eliminating high initial- and opera
tion
costs.‘
'
-
'
a
~
7
sired paraf?nic and ol’e?nic hydrocarbons, Or it
I‘
A most important feature'of the present: in
vention is‘ that high yields of high octane motor
may be necessary or desirable to obtain additional
supplies, as is well understood. ‘Additional ole
?nic hydrocarbons, if required, may be formed
from a portion of the para?lnic hydrocarbons.
fuelare obtained by? alkylating is'obu'tane ‘with
propylene in the presence of elemental-halogens,
particularly, chlorine and brominex ' In the. alky
On the other hand, additional para?lnic hydro
lation of isobutane with propylene, we especially
carbons may be admixed to increase the concen
prefer to use bromine‘ as'our catalyst.’ ‘We'havé
found that when bromine'is usedas the homo
geneous gaseous phase catalyst in the process of
the vpresent ‘invention,’ the alkylate ~ contains an
tration of paraf?nic hydrocarbons to a, desired
magnitude.
’
In carrying out our process,- we use tempera
turesv varying between about 590° F. and‘ about
appreciably larger proportion ofthetriptane- and
2,2-dimethylpentane-‘containing fraction. How'
ever, when 'bromineis used," the/concentration: of
the'triptane in the triptane‘; and 2,2-dimethylpen
These
?xed gases may furnish substantially all the de
850° F., and preferably temperatures varying be
' tween about 650° F. and about 825° F.
65
InLth’e
alkylation of isobutanewith propylene,‘ however,
tane-containing fraction is always lower-.E'The
higher yield of 2,2-dimethylpentane’ thus ob
tained, is ‘accompanied by a decrease'ginthe 21
we have found, as ‘disclosed in our copending ap
allgylation vreactions ' referred? *to',“ Produce fprode
drocarbons and no aromatics so that the predomi
plication Ser. No. 502,813, ?led September 17, 1943,
that the best yields of desired alkylate ‘are ob
tained when the 'alkylation is conducted at tem
methylhexane. Therefore,'since1it thus appears
peraturesfalling within about 750° F. “to about
that brominefavors the ‘?rst and second alklyla; 70 850°
F., and preferablypabout .7'75° F. to about
tion' reactions referred to hereinabove; ‘while
825° F. The alkylate produced under these con
chlorine favors the-?rst and-third alkylation re
ditions contains-no more than 5% of ole?nic hy
actionsreferred to; and since the ?rst and?second
ucts “that have the highest‘ an'd'higher octane 75 nance of alkylation obtained thereby is a distinct
23,410,071
8
Table I-I.--Co1itinuocts operation
7
featureof the process. Under appreciably high
er temperature conditions, side reactions ‘occur .
that‘ substantially reduce the purity of the prod
uct obtained. In the alkylation of isobutane with
propylene in accordance with the process of the UK
present invention, it must be noted that even
within the preferred temperature range, side re
actions occur that account for substantial por-_
tions of the total alkylate, but a fraction boiling
at 79° C. to 82° C. and consisting of 15 parts of 10
Run 3
Run 4
Para?in, percent by wt _________ __ Isobutane, 90v Iscbutane, 90.
Ole?n, percent by wt ___________ __ Propylene, 10. Propylene, l0.
Catalyst ________________________ __
Chlorine ____ __
Amount of catalyst, wt. % in
2.7 ____ __‘ _____ __
charge.
Temperature, ‘’ F _______________ __
Pressure, #/sq. in. gauge.
Reaction time in minutes. ,
triptane to 85 parts of 2,2-dimethylpentane may
__
_
.
.
‘>5
Bromine.
1.1.
800.
6,000.
25.
Product
be obtained. This reaction product is obtained in
Alkylate yield, weight percent of
15.3 _________ ._ 12.5.
best yields by injecting the reactants. and the
charge.
Alkylate, weight percent boiling
halogen catalyst separately, into the reaction zone
~
at optimum reaction temperature. The method 15 between76° C.—8fi° O ________________ __ 36 ___________ __ 40.
oi.’v conducting alkylation with homogeneous gase
ous phase catalysts embodying this feature forms
It must be noted that run 2, which was made
the subject matter of a copending application, Ser.
under identical conditions as run 1, with the ex
No. 516,242, ?led December 30, 1943.
The pressure to be used in our process may 20 ception that bromine was used as the homoge
neous gaseous phase catalyst, gave a higher yield
vary from about 500 pounds per square inch to
of the 'triptane-containing fraction boiling at 79°
about 6000 pounds per square inch or more, and
C.'to‘82° C; This'appears to be due to the tend
preferably from about 2500 pounds per square inch
ency of bromine to catalyze the reactivity of the
to about 6000 pounds per square inch for the
alkylation of isobutane with propylene, the most 25 tertiary isobutane hydrogen with resultant for
mation of larger amounts of 2,2-dimethylpen
suitable pressure being more or less dependent
tane and triptane, boiling at 80-81° C. This be~
upon the particular temperature involved. In
ing a desirable direction for this particular re
general, the higher the pressure, the higher the
action to go, indicates the advantages of bromine
yield of alkylate. Accordingly, the criterion for
establishing an upper limit to the pressure range 30 over chlorine as the catalyst. Infra red data
used is primarily the feasibility of maintaining
such pressure.
In our ‘process it is desirable, as in known iso
show, however,‘ that the alkylate formed by cat
alysts with chlorine is‘richer in desirable trip
tane than that produced by bromine.
The alkylate produced by our process is con
concentration of the ole?nic hydrocarbons rela 35 taminated by various halogen compounds which
are present in small concentration. These com
tively low during the alkylation reaction in order
para?in-ole?n alkylation processes, to keep the
to eliminate as much ole?n polymerization as
possible.
Accordingly, it is advisable to main
tain the ole?n concentration in the charge be
low about 25% by volume, and preferably between
about 7% and about 12% by volume.
The alkylate product that we obtain distills
over a fairly large boiling range, but a greater
part of the alkylate, usually from about 85% to
about 90%, distills in the boiling range of avia
tion gasolines. The iodine number of the avia
tion distillate is low, on the order of about 5 to
10. As mentioned hereinabove, the alkylate prod
uct consists predominantly of branched paraf
?nic hydrocarbons.
pounds cause a negative susceptibility to tetra
ethyl lead, and, therefore, should be removed.
Removal of these halogen compounds is possible
in a variety of ways, as set forth in copending
applications Ser. No. 477,450, ?led February 27,
1943; Ser. No. 502,504, ?led September 15, 1943;
and Ser. No. 504,436, ?led September 30, 1943.
Although the present invention has been de
scribed in conjunction with ‘preferred embodi
ments, it is to'be understood that modi?cations
and variations ,may be resorted to'without de
parting from thespirit and scope-of‘ the inven
tion as those skilled in the art will readily under
stand.- 1' Such‘variati'ons and vmodi?cations are
considered. to be within the purview and scope of
c
To illustrate our invention, we set forth be
low in Tables I and II, typical data obtained in
carrying out our process:
the appended claims.
We claim:
’
‘
1._ The process of manufacturing high octane
gasoline by alkylating 'isobutane with propylene,
which comprises contacting isobutane and pro
Table I.-Batch operation
pylene in a reaction zone under alkylating con
ditions including a temperature varying between
Run 1
about'775? F. and about 825° F.-and a pressure
Run 2
60 of at least 2500 pounds per square inch, with
Para?in, per cent by wt _________ __ Isobutane, 00. Isobutane, 90.
Ole?n, per cent by wt ___________ ._ Propylene, l0. Propylene, 10.
Chlorine ____ I.
Bromine.
Amount of catalyst, wt. per cent
atalyst__
1 2
1.2. >
in charge.
Temperature, ° F _______________ _.
Pressure, #/sq, in. gauge _________ __
____________________ _,
75
4,000 ________ __
,
750.
4,000.
Reaction time in minutes _______ I.
30 ___________ __
30.
Product
_
Allrylate, weight per cent boillng
et
an excess of isobutane over propylene in said re
action zone so that alkylation is the principal
reaction.
2. In a process of manufacturing high octane
’
Alkylate yield weight, per cent of
charge.
I
an valkylation‘catalyst consisting essentially of
bromine in amounts varying between about 1%
and’ about 1.25% of the charge, and maintaining
16 ___________ _Q 16.
» gasoline by alkylating a light paraffin with a
‘light ole?n in'a reaction zone under alkylating
.70 conditions and in the presence of catalytic mate
rial; the improvement which comprises contact
ing said light paraf?n and light ole?n in gaseous
phase and in said reaction zone under alkylating
conditions including a temperature varying be
75 ;tween ‘about '650" F. and about 825° F. and a
2,410,071
10
pressure of at least 1500 pounds per square inch,
with an alkylation catalyst consisting essentially
of a halogen selected from the group‘ consisting of
at least 1500 pounds per square inch, with an al
kylation catalyst consisting essentially of bro
chlorine and bromine which forms with said
mine, and maintaining an excess of the light par
a?inic hydrocarbon over the light ole?nic hydro
light paraffin and light ole?n, a single homoge
nous gaseous phase under said alkylating condi
the principal reaction.
tions, and maintaining an excess of the paraffinic
reactant over the ole?nic reactant in said reac
tion zone so that alkylation is the principal reac
tion.
,
3. In a process of alkylating a light para?in
with a light ole?n in a reaction zone under alkyl
carbon in said reaction zone so that alkylation is
8. The process of claim 7 wherein the alkyla~
'tion catalyst consists essentially of chlorine.
9. The process of alkylating a paraf?nic hydro
10 carbon with an ole?nic hydrocarbon, which com
prises contacting said para?inic hydrocarbon and
said ole?nic hydrocarbon in a reaction zone un
der alkylating conditions including temperatures
ating conditions and in the presence of catalytic
varying between about 590° F. and about 850° F.
material; the improvement which comprises con
tacting said light paraffin and light ole?n in said 15 and pressures of at least 500 pounds per square
inch, with an alkylation catalyst consisting es
reaction zone under alkylating conditions includ
ing a temperature varying between about 650° F.
and about 825° F. and a pressure of at least 1500
pounds per square inch, with an alkylation cata
sentially of bromine, and maintaining an excess
lyst consisting essentially of a halogen selected
from the group consisting of chlorine and bro
mine, in amounts varying between about 1% and
aobut 1.25% of the charge, and maintaining an
excess of the para?inic reactant over the ole?nic
the principal reaction.
of para?inic hydrocarbon over the ole?nic hydro
carbon in said reaction zone so that alkylation is
10. The process of claim 9 wherein the alkyla
tion catalyst consists essentially of chlorine.
11. The process of manufacturing high-octane
gasoline, which comprises contacting isobutane
‘reactant in said reaction zone so that alkylation 25 and propylene in a reaction zone under alkylating
is the principal reaction.
4. The process of manufacturing triptane by
conditions including temperatures varying be
tween about '7'75° F. and about 825° F. and pres
sures of at least 2500 pounds per square inch, with
alkylating isobutane with propylene, which com
an alkylation catalyst consisting essentially of
prises contacting isobutane and propylene in gas
eous phase and in a reaction zone under alkylat 30 chlorine, and maintaining an excess of isobutane
over propylene in said reaction zone so that al
ing conditionsincluding a temperature varying
kylation is the principal reaction.
between about 775° F. and about 825° F. and a
12. The process of manufacturing triptane,
giépressure of at least 2500 pounds per square inch,
which comprises contacting isobutane and pro
with an alkylation catalyst consisting essentially
of bromine which forms with said isobutane and 35 pylene in a reaction zone under alkylating condi
tions, with an alkylation catalyst consisting es
propylene, a single homogeneous gaseous phase
sentially of a halogen selected from the group
under said alkylating conditions, and maintaining
an excess of isobutane over propylene in said
consisting of chlorine and bromine, and main
reaction zone so that alkylation is the principal
taining an excess of isobutane over propylene in
reaction.
40 said reaction zone so that alkylation is the princi
pal reaction.
5. The process of manufacturing high-octane
13. The process of manufacturing high-octane
gasoline, which comprises contacting isobutane
conditions including temperatures varying be
gasoline, which comprises contacting a light par
a?inic hydrocarbon and a light ole?nic hydrocar
tween about 750° F. and about 850° F. and pres
sures of at least 2500 pounds persquare inch,
with an alkylation catalyst consisting essentially
bon in a reaction zone under alkylating condi
tions, with an alkylation catalyst consisting es
sentially of a halogen selected from the group
of bromine, and maintaining an excess of iso
butane over propylene in said reaction zone so
consisting of chlorine and bromine, and main
taining an excess of light para?inic hydrocarbon
50 over the light ole?nic hydrocarbon in said reac
and propylene in a reaction zone under alkylating
that alkylation is the principal reaction,
6. The process of alkylating isobutane with
propylene, which comprises contacting said iso
butane and said propylene in a reaction zone
under alkylating conditions including tempera
tures varying between about 750° Fl and about
850° F. and pressures of at least 2500 pounds per
square inch, with an alkylation catalyst consist
ing essentially of chlorine, and maintaining an
excess of isobutane over propylene in said re
tion zone so that alkylation is the principal re
action.
14. The process of alkylating a parai?nic hy
drocarbon with an ole?nic hydrocarbon, which
comprises contacting said paraf?nic hydrocarbon
and said ole?nic hydrocarbon in a reaction zone
under alkylating conditions, with an alkylation
catalyst consisting essentially of a halogen select
ed from the group consisting of chlorine and bro
action zone so that alkylation'is the principal 60 mine, and maintaining an excess of the para?inic
hydrocarbon over the ole?nic hydrocarbon in said
7. The process of manufacturing high-octane
reaction zone so that alkylation is the principal
gasoline, which comprises contacting a light par
reaction.
af?nic hydrocarbon and alight ole?nic hydrocar
AARON W. HORTON.
bon in a reaction zone under .alkylating condi 65
JOHN W. BROOKS.
tions including temperatures Varying between
ARLIE A. O’KELLY.
about 650° F. and about 825° F. and pressures of
reaction.
Certi?cate of Correction
v
October 29, 1946.
V i‘iPatent No. 2,410,071.
AARON W. HORTON ET AL.
‘ ‘It is hereby certi?ed that errors appear in the printed speci?cation of the above
nnibered patent requiring correction as follows: Column 1, line 29, for ‘~‘involvesi\\_l
I adinvolpe; column 5, line 20, before “phase” insert gaseous; column 8, lines 31 and
32,;for' “catalysts” read catalysis; column 9, line 23, for “aobut” read about; and that
the said; Letters Patent should be read with these corrections therein that the same
a 7111 “?liformebqihe lieqordoof the caseinrthe?liatent O?ice-.
'
Signed and sealed this 25th day of February, A. D. 1947.
LESLIE FRAZER,
First Assistant Oommz’ssz'oner of Patents.
‘ \4
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