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2,410,107
Patented Oct. 29, 1946
UNITED STATES "PATENT OFFICE
‘
2,41p,10.1
‘
'
‘
ALKYLATION PROCESS
Alexander N. Sachanen' and Arlie A. O’Kelly,
Woodbury,>N. J., and Claude G. Myers, Bryn
Mawr, Pa., assignors,,~to Socony-Vacuum Oil
Company, Incorporated, a corporation of New
York
No Drawing. Application September 11, 1943,
Serial No. 502,018
20 Claims. (c1. zoo-683.4)
1
2
respectively; or may be conducted in the pres
ence of alkylation catalysts at lower tempera
tures and pressures, thereby assuring. a high
This invention relates to the alkylation of
paraf?nic hydrocarbons with ole?nic hydrocar
bone and is more particularly concerned with the
production of high octane motor fuel by the
catalytic alkylation of normally gaseous paraf
hydrocarbons.
yield of desired alkylate by avoiding extensive
degradation of the reactants, the occurrence of
side and secondary reactions, and appreciable
polymerization-of the ole?nic reactant. The two
Various commercial processes have been proposed
for ultimately effecting the desired polymeriza
ole?nic hydrocarbons. For instance, it is known
?nic hydrocarbons with normally gaseous ole?nic
methods are known as thermal alkylation and as
It is well known in the art to polymerize ole?nic
catalytic alkylation, respectively.
hydrocarbon gases to produce motor fuels hav
Several methods are known for the catalytic
ing constituents of an unsaturated character. 10
tion of the ole?nic hydrocarbons. These proc
esses have been predicated upon the dictates of
the chemical nature of the stocks available as
alkylation of isoparai?nic hydrocarbons with
to alkylate isoparaf?nic hydrocarbons with
ole?nic hydrocarbons in the presence of sulfuric
15
acid, phosphoric acid, metal phosphates, metal
ole?nic hydrocarbons produced in the earlier
halides, activated clays and the like, as catalysts.
In these catalytic alkylation processes, the hy
drocarbon reactants form with the alkylation
catalysts, a, heterogeneous system, during the
paraf?nic hydrocarbon, hereinafter called the
para?’mic reactant, and an ole?nic hydrocarbon,
activity. It must be noted, however, that insofar
well as engineering considerations such as initial
and operation costs; their essential feature being
that in the course of treating the materials, the
stages of the process, are eventually polymerized 20 alkylation‘ operation. Since under alkylation
conditions, the catalytic activity of the alkylation
to'gasoline. Accordingly, hydrocarbon gases may
catalysts appears to be predicated upon contact
be passed along with cracking stock or naphtha
between the catalysts and the gaseous hydrocar
through a cracking stillto crack and polymerize
bon» reactants at the interfaces therebetween, in ~
such gases to gasoline simultaneously with v‘the
cracking or reforming, or para?inic hydrocarbon 25 these processes, the catalysts are used in amounts
varying between 10% and 200% by weight, on the
gases may be separately cracked to ole?nic hy
charge, depending on the catalyst used. Due to
drocarbon gases and these gases are subsequently
these comparatively high amounts, where pos
passed with naphtha through a polymerizing and
sible, recovery and regeneration of the catalysts
reforming still. In some instances, the proc
esses involve the use of catalysts for facilitating 30 have been proposed. This, of course, involves
high initial and‘ operation costs. Further, it is
the cracking and/or polymerization operations.
also known that certain substances called pro
It is also well known in the art, to combine
moters, promote the catalytic action of these
paraffinic hydrocarbons directly with ole?nic hy
alkylation catalysts. .Accordingly, several proc
drocarbons by processes broadly called alkylation
esses have been proposed wherein small amounts
35
processes, to produce motor fuels having con
of these promoters, on the order of about 1% to
stituents of saturated character. In alkylation
3% by weight on the charge, are added to the
processes, a charge comprising a mixture of a
hereinafter called the ole?nic reactant, is sub
jected to high temperature and pressure to pro
duce a saturated alkylate product. Since condi
tions of alkylation also cause polymerization of
the ole?nic reactant, it is necessaryto maintain
a relatively low concentration of the ole?nic re
actant in the charge. rl'he only limit to the pres
sure used appears to be the feasibility of main
taining high pressures. On the other hand, the
catalysts to promote theirv alkylation catalytic
40 as we are aware, no catalytic alkylation process
is known wherein these promoters are used ex
clusively as catalysts.
'
We have found that para?im'c hydrocarbons
may be e?iciently alkylated with ole?nic hydro
45 carbons to produce high yields of high octane
gasoline by using promoter amounts of alkyla
tion catalysts that form, with the hydrocarbon
reactants, a single homogeneous gaseous phase
during the alkylation operation.
temperature used is limited by thedegradation
of the hydrocarbon reactants in the charge to low 50 vIt is an object of the present invention to
provide an e?icient process for catalytically alkyl
molecular weight hydrocarbons and the occur
ating 'para?inic hydrocarbons with ole?nic hy
rence of side reactions, including polymerization
drocarbons. Another object of the present in
of the ole?nic reactant under high temperature
conditions that substantially reduce the purity of '
the product obtained.
,
Alkylation‘may be conducted at high tempera
vention is to provide an ef?cient process for
55 catalytically alkylating either normal paraf?nic
hydrocarbons or isopara?inic hydrocarbons with
ole?nic" hydrocarbons. A more speci?c object is
tures and pressures, on the order of, over 900° F.
and over 4000 pounds per square inch,‘ gauge, . to provide a process for catalytically alkylating
,3
2,410,107
4
normally gaseous para?inic hydrocarbons with
phase catalysts of our process inherently furnish
normally gaseous ole?nic hydrocarbons to Pro
duce high yields of high octane gasoline. Avery
important object of the present invention is to,
the greatest possible “interfacial contact” be
tween the catalyst and the hydrocarbon reactants
under the conditions of alkylation, e?icient cat
alytic activity with a concomitant high yield of
high grade alkylate is achieved using relatively
small amounts of homogeneous gaseous phase
a?ord a process capable of carrying out the
above objects by using an alkylation catalyst
which forms with the hydrocarbon reactants, a
single homogeneous gaseous phase during the
catalyst.
‘
In view of the foregoing, an operation fea
alkylation operation. Other objects ‘and ad;
vantages of the present invention will become 10 ture of the process of the present invention that
apparent to those skilled ‘in the art from the
following description.
is of considerable practical importance is that
small or promoter amounts of alkylation catalyst
are used. In operation, we use catalysts in
Broadly stated, the present invention provides
a process for alkylating paraf?nic hydrocarbons
~ amounts varying between about 0.5% and about
with ole?nic hydrocarbons which comprises con 15 3%, preferably in amounts varying between about
tacting a para?inic hydrocarbon and an ole?nic
1% and about 1.25% with respect to the total
hydrocarbon in a reaction zone under alkylat
charge of hydrocarbon reactants. These amounts
ing conditions, with promoter ‘amounts ‘of an
are ‘so small that the catalyst may be discarded
alkylation catalyst consisting essentially of a
feasibly, vthereby obviating recovery and regener
‘material that forms with the hydrocarbon re 20 ation problems and eliminating high initial and
actants, a single, homogeneous gaseous phase 7
operation costs. It must be not-ed, however, that
under the alkylation conditions of the reaction
larger amounts of catalyst may be employed if
zone.
desired, although no additional advantages result
An ‘important feature of the present invention
therefrom.
is the fact that, contrary to ‘the known catalytic 25
The homogeneous gaseous phase alkylation
alkylation processes of the "prior art which are
catalysts of the present invention may be solids,
‘only capable of alkylating isoparafdnic hydro
liquids or gases under normal conditions. How
carbons, our process is capable of alkylatihg either
ever, it is essential for the purposes of the pres
normal paraiiinic hydrocarbons or isopara?‘lnic
ent invention,‘ that the catalyst form with the
hydrocarbons with substantially equal ease.
30 hydrocarbon reactants being processed, a single,
Another important feature of our process is
homogeneous gaseous phase under the alkylation
the relatively low temperature that may be used.
conditions of the process. Organic halogen com
As a result, degradation of the hydrocarbon re
pounds have been found to be very effective cat
alysts of this type. The organic halogen com
actants in the charge to' low molecular weight
hydrocarbons and the occurrence of side reactions 35 pound eatalysts comprise organic halogen deriva
including polymerization of the ole?nic reactants,
tives of hydrocarbons, wherein halogens have
are substantially completely avoided. Conse
been substituted for part or all of the hydrogen
quently, in the process ‘of the present invention,
of an organic compound. Generally speaking,
we obtain high yields of a high grade product
the preferred catalysts 'of the present invention
7 that is almost entirely paraf‘onic in nature and 40 are organic halogen derivatives of hydrocarbons,
is substantially free from impurities. For in
_ and, particularly, cheap chlorine derivatives,
stance, we have obtained yields of alkylate gaso~
wherein chlorine is substituted onto a non-ring
line in amounts of up to 200% by weight per
portion, if any, of the hydrocarbon. It is to be
pass based on the olefinic vhydrocarbon content
understood herein, that by “derivatives” of hy
in the charge, and the gasoline had an octane
drocarbons, we mean compounds wherein all the
value of 85 C. F. R. motor method.
hydrogen has been substituted, e. g., carbon tet
A most important feature of the present in
rachloride, as well as compounds wherein only
venti'on is the ‘fact that, contrary to the known
part of the hydro-gen has been substituted, e. 8-,
catalytic alkylation processes of the prior art, in
chloroform; the e?iciency of the catalysts appar
which the hydrocarbon reactants being processed
ently being somewhat in proportion to the ease
form with the alkylation catalysts, a' hetero
with which they decompose during the alkyla~
geneous system during the alkylation operation,
tion. We especially prefer to use as our cata
the alkylation process of our invention employs
lysts, chlorinated derivatives of light paraf?nic
alkylation catalysts consisting essentially of ma
hydrocarbons including hydrocarbons of gaso
terials that form with the hydrocarbon reactants
line-boiling range. Thus, at the present time, we
being processed, a single, homogeneous gaseous
consider a chlorinated naphtha or a chlorinated
phase under alkylating conditions. The alkyla
tion catalysts of the present invention vmay be
called, therefore, homogeneous gaseous phase
catalysts in contradistinction to the alkylation 60
catalysts of the prior art, which may be re
ferred to as heterogeneous catalysts. Accord
ingly, as a result of the catalyst being in the
same phase or state as the hydrocarbon reactants
butane as the most feasible homogeneous gaseous
phase catalyst from a practical standpoint.
However, other speci?c catalysts that may be
mentioned by way of nonlimiting example are:
chloroform; carbon tetrachloride; ethyl chloride;
ethylene dichloride; trichlor-acetic acid; chloral;
acetyl chloride; benzoyl chloride; benzyl chlo
ride; dichlor-propane; dichlor-isobutane; iso
butylene dichloride; propylene dichloride; 1,2,3
trichlor-propane; dichloro-difluoro methane; di
being processed, fouling of the catalyst is sub‘ 65
stantially eliminated, and agitation and/0r mix
ing problems are non-extant. Further, since the
chloro-monofluoro methane; methyl-chlor ace
catalytic activity of alkylation catalysts appears
tate; propylene dibromide; dibrom isobutane;
to be predicated somewhat upon contact between
ethyl bromide; propylene tribromide; tertiary
the catalysts and the gaseous hydrocarbon ‘re 70 monobrom butane; and'so forth. 'It is to be un
actants at the interfaces therebetween, it fol
lows that the catalytic e?iciency of a given cat
alyst increases with the increase in area of inter
’facial contact, other variables remaining con
stant. Hence, since the homogeneous gaseous 75
derstood, of course, that free halogens or hydro
gen halides, reacting with hydrocarbons, can be
used to form our homogeneous gaseous phase cat
alysts in situ.
Certain nitro organic compounds, heterocyclic
2,41 0,107
6
ing an upper limit to the pressure range used is
‘primarily the feasibility of maintaining such
oxygen compounds and elemental halogens as
well as certain organic halides containing a ni
tro-group have been found also to be very e?ec
pressure.
In our process, it is desirable, as in known iso
tive homogeneous gaseous phase catalysts. Ni
para?in-ole?n alkylation processes, .to keep the
‘concentration of the ole?nic hydrocarbons rela
tromethane, propylene oxide, bromine 'and'chlo
rinef and l-chloro l-nitro-propane may be‘mene
tively low during the alkylation reaction in order
to eliminate as much ole?n polymerization as
tioned by way of non-limiting examples. i- These
types of homogeneous gaseous phase catalysts
possible._ Accordingly, it is advisable to main
form the subject matter of separate applications
for Letters Patent, namely, Ser. No. 508,062, ?led 10 tain the ole?n concentration in the charge below
about 25% by volume and preferably, between
October 28, 1943; Ser. No. 513,720, ?led'Decem
about ‘7% and about 12% by volume.
' ber'~10,~1943; Ser. No. 502,812, ?led September 17,
The alkylate product that we obtain ,distills
1943.
'
'
'
»*
-
‘1
over a fairly large boiling range, but a greater
The para?inic and ole?nic'hydrocarb‘ons to be
used in our process may be derived-from any suit 15 part of the alkylate, usually from about 85% to
90%, distills in‘ the 'boiling range of aviation
able source, as is well known in the art, and may
gasolines. The iodine number of the aviation
be used either in the pure state or in admixture
distillate is low, on the order of about 5 to 10',
with other constituents not undesirable. 'The
when the temperature of the process is'rnoderate,
paraf?nic and ole?nic hydrocarbons usually em
ployed in the preferred operation of manufac 20 say, up to 650° F. in batch operation, and up to
700° F. to 800° F. in continuous operation. 'At
turing motor 'fuels will be the normally gaseous
higher temperatures, the iodine number may in
'paramnic hydrocarbons, except methane and
crease up to 20 or 50. As has been'mentioned
ethane, and the normally gaseous ole?nic hydro
hereinabove, the alkylate product consists pre
carbons, as is well understood in the art. Here
dominantly of branched para?'ins.
again our process has a distinct advantage over
To illustrate our invention, we set forth below
many of the prior art processes in that the ole?n
in Tables I and II, typical data obtained in carry
ethylene may be used for alkylating the para?inic
ing outour process:
.
hydrocarbons. It is well known that ethylene is
less reactive in catalytic reactions than some of
Table I .-—Batch operation
the higher ole?nic hydrocarbons, such as the 30
butylenes. For this reason, ethylene cannot be
used in many catalytic processes, including the
Run 1
sulfuric acid process, whereby the supply of avail
able ole?nic hydrocarbons is restricted. There
fore, an important aspect of the present inven 35
tion is the fact that butane, for instance, may be
Paraffin, parts
weig
butane with ethylene substantial quantities of
=
time,
.
.
Product
'
30.
-
320 __________ __
320".‘_______ __ ‘320.
point; ° F.
r
Parts by weight-
10 ___________ __
120 __________ __
135.
Percent
10 ___________ ._
128 .......... __
165.
by
line
based’ on
ole?n.
_
'
,
Structure _____ ..‘__ Appears to be
sired para?inic and ole?nic hydrocarbons, vor it
.
may be- necessary or desirable to obtain addi
Heavy
~
'
Branchedpar-
polymerized
a?‘ins.
Branched par
-
a?ins.
ethylene.
ends
'
______________ __
14..‘ _________ __
13.
(above 320° F.),
tional supplies, as is well understood. Additional 50
weight.
olefinic hydrocarbons, if required,'may be formed
frame, portion of the para?lnic hydrocarbons.
0n the other hand, additional paraf?nic hydro
Table I.--Batch operation (Continued) ’
carbons may be admixed, in ‘order to increase'the '
concentration of para?inic hydrocarbons to a de
'
’ weight of gaso
?xed gases may furnish substantially all the de
'
82.
1% CECIL-“ 1% CHGh.
Same as run 1.. 625.
___..do ....... __ 3000.
>
Gasoline end
obtained around petroleum re?neries._ These
sired magnitude.
n-Butane, '600.
1.
________________ _.do _______ ._
min.
-_A vconventional and preferred source of par
af?nic and ole?nic hydrocarbons is the ?xed gases 45
‘
>
.
Reaction
the alkylate boiling up to 320% F., produced from
isobutane and ethylene. The importance of this
contribution is obvious.
'
Ethylene, 94__ ___._do _______ __ Ethylene,
Catalyst ________ ._ None_.
Temperature, ° F. 625.-"
Pressure #/sq. in. 3300--.
neohexane are produced. As a matter of fact, we
obtain on an average about 45% of neohexane in 40
Run 3‘
Isobutane,635_ Same as Run
by weight.
ole?mmparts by
alkylated with ethylene. Thus, by reacting iso
Run 2
65
Run 4
'
'
Run 5
Rune‘
In carrying out our process We use tempera
tures varying-between about 590° F. andabout
Paral?lrlié parts by Isobntane, 600. Isobutane, 600. Isobutane, 600.
8509» F. or highen'and, preferably, temperatures
Ole?n h-Eatts by Ethylene, 90. . Propylene, 140 Ethylene, 125.
varying between about 650° Rand about 825° F. 60 Catalyst;v____ _.'._ 0 8g, 1
1% 011013. .,._ Chlornaphtha.
The‘ 'alkylate produced under these conditions
contains no more than 5% ‘of ole?nic hydrocar
bons and no aromatics so that the predominance
of alkylationwobtained thereby is a distinct ‘fea
substantially reduce the purity of the ‘product
obtained:
~‘
-
'
I
.
.
.
r
higher the pressure, the higher the yield of al
kylate. Accordingly, the criterlon'for establish
‘
r
4
'
,
HgOH?Ol
725
,
'
'
_
750.
Pressure, #/sq. in. f
3700.
Reaction
30.
time,v I
~.mm.
I
‘ Product
Gasoline end
point °
, Parts‘ by weight"
Per cent -b y
weight of vgaso
The pressure to be used may vary from about
500'pounds per square inch to about 3000 pounds 70 line based on
ole?n.
per square inch or more, the most suitable pres-'
Structure___v______
sure being-more or less dependent upon the par
H e av y en des
ticular temperature involved. In‘ general, the
>
r
Temperature, "F
ture of the process. Under appreciably higher 65
temperature conditions, side‘ reactions occur that
weig
welg
(above 320° F.),
' parts by weight. '
320.
3,20 _____
119 __________ __
164.
~
160.
132"; _______ ._
’
Branched par
vBranched par
a?ins.
19 ___________ __
:2
27
us.
Branched par
a?ins.
20.
_
acidic?
7
8
Table II .-Continuous operation
hydrocarbon selected from the group consisting
Run?
Para?in, per cent
Is 0 b utane,
88.5.
by weight.
Ole?n, per cent
Ethylene, 11.5.
Catalyst ________ ._
1% OHC]3_ _ -_
Temperature, ° F_
750 __________ _.
by weight.
Run8
Rune
Do.
Do.
1000;
320 __________ _
320.
161 __________ __
56.
weight of gaso
line‘ based on
i
Branched par
a ?ins .
tion catalyst consists essentially of a material se
lected from the group consisting of chlorinated
naphtha and brominated naphtha.
a?ins.
Sp. gravity _____ __
0.673 ________ _
0.677;
l3
18.
4
Octane value, 0.
85.
motor
methods
H e a v y e n d sv
5.
(above 320° F.),
cent by
weight of heavy
5. The process of claim 1 wherein the alkyla
tion catalyst consists essentially of a material se
ZBranched per
Iodine No ...... -_
R.
v10 low-boiling tertiary acyclic hydrocarbons.
4.,’I‘he process of claim 1 wherein the-alkyla
15
'
Structure _______ __
F.
hydrocarbon selected from the group consisting
of chlorine derivatives of low-boiling tertiary
acyclic, hydrocarbons and bromine derivatives of
Do.
.____do _______ __
Product
ole?n.
3. The process of claim 1 wherein the alkyla
tion catalyst consists essentially of a halogenated
Same asrun 7. Same as run 7.
Pressure, #’sq. in.
G a s o l i n e end
point, ° F.
P er cent by
of chlorine derivatives of low-boiling acyclic hy
drocarbons and‘ bromine derivatives of low-boil
ing acyclic hydrocarbons.
lected from the group consisting of chlorinated
butane and brominated butane.
6. The process of manufacturing high octane
20 gasoline, which comprises contacting a. normally
gaseous paraf?nic hydrocarbon with a normally
per
gaseous ole?nic hydrocarbon, in gaseous phase in
ends based on
a reaction. zone under alkylating conditions in
cluding a temperature varying between about
ole?n.
25 650° F. and about 825° F. and a pressure in excess
of about 1500 pounds per square inch, with an
It must be noted that run 1 which was made
alkylation catalyst consisting‘ essentially of a
without acatalyst, gave a 10% yield of ethylene
halogenated hydrocarbon selected from the group
polymers. Run 2 which was made under iden
consisting of chlorine derivatives of acyclic hy
tical conditions, with the exception that 1% of
chloroform was used, gave a 128% yield of iso 30 drocarbons and bromine derivatives of acyclic
hydrocarbons, that forms with said normally
para?ins boiling up to 320° F.
gaseousparaf?nic hydrocarbon andwith said nor
The alkylate produced by our process is con
taminated by various halogen compounds which
are present in small concentration. These com-v
pounds cause a negative susceptibility totetra
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 2'1,
1943; Ser. No. 502,504, ?led September 15, 1943;
and Ser. No. 504,436, ?led September 30, 1943.
This application is a continuation-in-part of
our co-pending application Ser. No. 403,870, ?led
July 24, 1941.
>
Although the present invention has been de
mally gaseous ole?nic hydrocarbon, a single,
homogeneous gaseous phase under said alkylating
conditions, in amounts of at least 0.5% by weight
based on the total Weight of said normally gase
ous para?inic hydrocarbon and said normally
gaseous ole?nic hydrocarbon, and maintaining
the normally gaseous paraf?nic hydrocarbon in
40 excess over the normally gaseous ole?nic hydro
carbonv in said reaction zone so that alkylation is
the principal reaction.
7. The process of claim 6 wherein the alkyla
tion catalyst consists essentially of a halogenated
45 hydrocarbon selected from the group consisting
of chlorine derivatives of low-boiling acyclic hy
scribed in conjunction with preferred‘ embodi
drocarbons and- bromine derivatives of low-boil
ments, it is to be understood that modi?cations
ing acyclic hydrocarbons.
and variations may be resorted to without depart
8. The. process of claim 6 wherein the alkyla
ing from the spirit and scope of the invention, as
those skilled in the art will readily'understand. 50 tion catalyst consists essentially of a halogenated
hydrocarbon selected’ from the group-consisting
Such variations and modi?cations are considered
to be within the purview and scope of the ap-.
of- chlorine derivatives of, low-boiling tertiary
pended claims.
acyclic hydrocarbons and bromine derivatives of
'
We claim:
1. The process of alkylating a para?inic hydro
carbon with an ole?nic hydrocarbon, which com
low-boiling tertiary acyclic hydrocarbons,‘
5,5
9. The process of claim 6 whereinthe alkyla
tion catalyst consists essentially of a material se
lected from the. group consisting of chlorinated
prises contacting a para?inic hydrocarbon with
naphtha and brominated naphtha.
an ole?nic hydrocarbon, in gaseous phase in a
reaction zone under alkylating conditions includ
1,0. The process ofv claim 6 wherein the alkyla
ing a temperature varying between about 590° F. 60 tion catalyst consists essentially of. a material
and about 850° F. and a pressure in excess of
selectedfrom the group consisting of chlorinated
about 500 pounds per square inch, with an alkyla
butane and brominatedbutane.
tion catalyst consisting essentially of a halo
11. The process of manufacturing high octane
genated hydrocarbon selected from the group
gasolinei which comprises contacting isobutane
consisting of chlorine derivatives of acyclic hy 65 withethylene, in gaseousphase in a reaction zone
drocarbons and bromine derivatives of acyclic hy
under alkylating conditionsincluding a tempera
drocarbons, that forms with said para?inic hy
ture varying between about 590° F. and’ about
drocarbon and with said ole?nic hydrocarbon, a
850° F. and a pressure in excess of about 500
single, homogeneous gaseous phase under said‘ al
pounds per square inch, with an alkylation cata
kylating conditions, and maintaining the par 70 lyst consisting essentially of a halogenated hydro
af?nic hydrocarbon in excess over the ole?nic
hydrocarbon in said reaction zone so that alkyla
tion is the principal reaction.
carbon. selected from the group consisting of
chlorine derivatives of acyclic hydrocarbons and
bromine derivatives-of acyclichydrocarbons, that
forms with said isobutane and with said ethylene,
tion. catalyst . consists essentially of. ahalogenated 75 a. single,;homogeneous. gaseous phase. under said
2. The process of claim 1 wherein the alkyla
2,410,107
0.
t)
.
rivatives of acyclic hydrocarbons and bromine
alkylating conditions, and maintaining the iso
tion zone so that alkylation is the principal re
action.
12. The process of claim 11 wherein the alkyla
tion catalyst consists essentially of a halogenated
hydrocarbon selected from the group consisting
derivatives of acyclic hydrocarbons, that forms
with said isobutane and with said ethylene, a
single, homogeneous gaseous phase under said
alkylating conditions, in amounts of at least 0.5%
by Weight based on the total weight of said iso
butane and said ethylene, and maintaining the
of chlorine derivatives of low-boiling acyclic hy
drocarbons and bromine derivatives of low-boil
isobutane in excess over the ethylene in said reac
tion zone so that alkylation is the principal reac
butane in excess over the ethylene in said reac
ing acyclic hydrocarbons.
13. The process of claim 11 wherein the alkyla
tion catalyst consists essentially of arhalogenated
hydrocarbon selected from the group consisting
of chlorine derivatives .of low-boiling tertiary
acyclic hydrocarbons and bromine derivatives of
low-boiling tertiary acyclic hydrocarbons.
14. The ‘process of claim 11 wherein the alkyla
tion catalyst consists essentially of a material
selected from the group consisting of chlorinated
naphtha and brominated naphtha.
10
tion.
,
17. The process of claim 16 wherein the alkyla
tion catalyst‘consists essentially of a halogenated '
hydrocarbon selected from the group consisting
of chlorine derivatives of low-boiling acyclic hy
drocarbons and bromine derivatives of low-boil
ing acyclic hydrocarbons.
18. The process of claim 16 wherein the alkyla
tion catalyst consists essentially of a halogenated
hydrocarbon selected from the group consisting
20 of chlorine derivatives of low-boiling tertiary
acyclic hydrocarbons and bromine derivatives of
15. The process of claim 11 wherein the alkyla
low-boiling tertiary acyclic hydrocarbons.
tion catalyst consists essentially of a material
19. The process of claim 16 wherein the alkyla
selected from the group consisting of chlorinated
tion catalyst consists essentially of a material
butane and brominated butane.
16. The process of manufacturing neohexane, 25 selected from the group consisting of chlorinated
naphtha and brominated naphtha.
which comprises contacting isobutane with eth
20. The process of claim 16 wherein the alkyla
ylene, in gaseous phase in a reaction zone under
tion catalyst consists essentially of a material
alkylating ‘conditions including a temperature
selected from the group consisting of chlorinated
varying between about 650° F. and about 825° F.
and a pressure in excess of about 1500 pounds per 30 butane and brominated butane,
ALEXANDER N. SACHANEN.
square inch, with an alkylation catalyst consist
ARLIE A. O’KELLY.
ing essentially of a halogenated hydrocarbon se
CLAUDE G. MYERS.
lected from the group consisting or chlorine de
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