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2,410,108
Patented Get. 29, 1946
UNITED; STATES PATENT‘ ‘OFFICE
ALKYLATION.
Alexander
Sachanen and Arlie A. Q’Kelly,
'Woodbury, N. .L, and Claude‘G. M32615, Bryn;
' Mawr,‘ Pas assignors to 'Soriony-Vaouum Oil‘
Gompany, Incorporated, a corporation, of New
York
‘No Drawing. Application September 15, 1944:,
Serial No. 554,342.
20 Claims.
(Cl. 260-.—-683.4)
1.
This invention relates generally, to the alkyla
tion of paraf?nic hydrocarbons with olefinic hy
drocarbons, and is more particularly concerned
with the production of higheoctane motor fuel
by the catalytic alkylationof paraf?nic hydrocar
bons with ole?nic hydrocarbons,
2
pressures employed in’ alkylation operations, de
pend‘ upon whether the alkylation is effected in
the absence or presence of alkylation catalysts.
The two methods are generally referred ‘to’ as
thermal and‘; catalytic alkylation, respectively.
As is well known’, in the art, thermal alkylation
ordinarily involves the use of temperatures of at
least about 909° F. and pressures of the order of
4000; pounds per square inch or higher. At these
,
It is well known in the art to polymerize ole-?nic
hydrocarbon gases to produce motor fuels having
constituents of an unsaturated character. Var
ious commercial‘ processes have been proposed
temperatures, the degradation of the hydrocar
bon reactants in the, charge, and; the occurrenee
of side‘ reactions, including polymerization of‘ the _
ole?nic reactanthis ‘somewhat marked. On the
for ultimately effecting the desired polymeriza
tion of‘ the ole?nic hydrocarbons. These proc
esses have been predicated upon the dictates of
other hand, catalytic alkylation involves the use
the chemical nature of the stocks available, as
of appreciably lower temperatures, thereby assure
well‘ as engineering considerations such as initial 15 ring
a high yield ofv desired alkylate by avoiding
and operation costs; their essential feature being
extensive
degradation of the reactants, the oc
that in the course of‘ treating the materials, the
currence ofgsécqndary rea9ti0n$,,, and appreciable
ole?nic hydrocarbons produced‘ in the earlier
polymerization of, the ole?riic reactant
' ,SevBral methods are, known for. the catalytic
alkylation. oi isonara?inis hydrocarbons with
qlefmip,hydrocarbons- For instance, it is. knqwn
tol'alkylate. isorara?inic hydrocarbons with. Ole
stages ofthe process, are eventually polymerized
into, hydrocarbons boiling within the gasoline 20
boiling range. Accordingly, hydrocarbon gases
maybe passed along with cracking stock or
naphtha through a cracking still, to crack and
polymerize such gases to gasoline simultaneously" ?nic hydrocarbons in, the presence of sulfuric
with the cracking or reforming, or para?inic 25 acid; nhosphoric acid, ‘metal phosphates, metal
ha?dcs. activated clays and the like, as Catalysts
hydrocarbonv gases” may be separately cracked
In. these catalytic alkylation processes, the hydro
into olefinic hydrocarbon gases and these gases
carbon reactants form with the alkylation, cata
are subsequently passed with naphtha through
a polymerizing- and reforming» still. In some
instances, the processes involvethe use of cata
lysts, a heterogeneous system, during the alkyla
30 tion operation. Hence these alkylation catalysts
may be termed heterogeneous alkylation cata
lysts for facilitating‘ the cracking and/or poly
merization operations.
'
lysts. Since under alkylation, conditions, the
catalytic activity of the alkylation catalysts ap
'
It is also ‘well known in the art; to combine
paraf?nici hydrocarbons directly with olefinic
hydrocarbons byprocesses broadly calledj alkyla
tion processes, to produce motor fuels'having con;
stituents of saturated: character». In alkylation
processes, a charge; comprising a miXture'oPa
para?inic hydrocarbon, called the para?inic' re
actant, and an; olefinic hydrocarboncalled the
ole?nic' reactant, is subjected to high-tempera
35
pears to be predicated upon contact between the
catalysts and the gaseous hydrocarbon reactants
at the interfaces therebetween, in these proc
esses,v the catalysts are, used- in amounts ’ varying
between 10% and 200% by weight, on the charge,
40
ture and‘ pressure toproduce a saturated alkylate
product. Since conditions of alkylation also
cause polymerization‘ of‘ the ole?nic reactant, it
isnecessary to maintain a relatively low‘concen 45
tration of the ole?nic- reactant in the charge.
The only limit to the pressureused appears tov
dependingv on the catalyst used. Due to these
comparatively‘ high amounts, where possible, re
covery and regeneration of the catalysts have
been proposed. I'I‘his, of course, involves high
initial and operation‘ costs. Further, it is also
known that certain substances called promoters,
promote the catalytic activity of these alkylation
catalysts. Accordingly, several processes have
been proposed wherein small amounts of these
promoters, on the order of- about 1% to 3% by
be the feasibility of maintaining high pressures. "
weight
on the charge, are added. to the. catalysts
On the other handg'the temperature used is'lim
their alkylation catalytic activity.‘
ited by degradation of the hydrocarbon reactants 50 toApromote
copending
application, Serial'Nurnber 502,018,
in the charge to low molecular weight hydrocar
?led
September
11, 1943, is directed to theprocess
hens, and the occurrence of side reactions, in
eluding polymerization of the ole?nic reactant, . of alkylating» normal paraf?nic or isopara?‘inic
with ole?nic hydrocarbons, which
under‘high temperature conditions, that‘ sub 55 hydrocarbons
comprises
contactinga normal paraffinic or iso
stantially reduce the purity of‘ the product
para?inic hydrocarbon» and an ole?nic hydrocar
obtained.
‘
hot! in» a reaction‘ zone. under alkylating condi
The temperatures and to a certain, extent, the
2,410,108
3
tions, with small or promoter amounts of what
phase alkylation catalyst consisting essentially of
an octane number of 93.4, and since 2,3-dimeth
ylpentane and 2,4-dimethylpentane which are
the predominant constituents of the alkylate ob
a material that forms with the hydrocarbon re
tained in the alkylation of isobutane with pro
has been termed therein, a homogeneous gaseous
actants, a single homogeneous gaseous phase
under the alkylation conditions of the reaction
pylene in the presence of heterogeneous alkyla
tion catalysts, have octane numbers of 89 and 82,
zone. The alkylation conditions of the process
respectively, the importance of the alkylation of
of this copending application, comprise a broad
isobutane with propylene in the presence of
temperature range of about 590° F. to about
homogeneous gaseous phase alkylation catalysts
850° F., preferably, about 650° F. to about 825° F., 10 under alkylation conditions that favor the pro
and pressures of at least 500 pounds per square
duction of triptane is manifest. It was also found
inch gauge, preferably, pressures of at least 1500
that in actual practice, it was impossible to ob
pounds per square inch.
tain triptane exclusively, appreciable amounts of
Another copending application, Serial Number
502,813, ?led September 17, 1943, is directed to
2,2-dimethylpentane and 2-methylhexane being
the process of alkylating isobutane with pro,
The speci?c classes of homogeneous gaseous
phase catalysts disclosed in these copending ap
plications, are organic halogen compounds, and
the claims are directed to the use of chlorine and
bromine derivatives of acyclic hydrocarbons, as
pylene, which comprises contacting isobutane and
propylene in a reaction 'zone under closely con
trolled alkylating conditions, with promoter or
small amounts of the homogeneous gaseous phase
catalysts broadly disclosed in the copending appli
cation referred to hereinbefore, the closely con
always formed.
'
homogeneous gaseous phase alkylation catalysts.
Chloroform, chlorinated naphtha, chlorinated
butane, carbon tetrachloride, ethylene dibromide,
acetyl chloride, propylene dibromide, dibromiso
trolled alkylating conditions including a tempera
ture range of about 750° F. to about 850° F., pref
erably, about 775° F. to about 825° F., and pres 25 butane, ethyl bromide, propylene tribromide, and
sures of at least 2500 pounds per square inch
tertiary monobromo-butane are among the spe
gauge. In the alkylation of isobutane with pro
ci?c chlorine and bromine derivatives of acyclic
pylene in the presence of homogeneous gaseous
hydrocarbons mentioned as suitable homogeneous
phase alkylation catalysts, it was found that the
gaseous phase alkylation catalysts for the alkyl
alkylate obtained included constituents that are 30 ation processes disclosed in these copending ap
entirely different from the constituents of the
plications.
hydrocarbon alkylate obtained in the alkylation
The present invention is predicated On the use
of isobutane with propylene in the presence of
of organic halogen compounds, generally, as ho
known heterogeneous alkylation catalysts, i. e.,
AlCls, H2SO4, and the like. Thus, when hetero
geneous alkylation catalysts are used, 2,3-di
methylpentane and 2,4-dimethylpentane are im
portant constituents of the hydrocarbon alkylate
obtained. _On the other hand, when homogene
ous gaseous phase alkylation catalysts are em
ployed, triptane or 2,2,3-trimethylbutane, 2,2
dimethylpentane, and Z-methylhexane may be
the predominant constituents of the hydrocarbon
'alkylate. In this copending application, the for
mation of these three compounds was postulated
as follows:
1.
Isobutane
Propylene
l a
Ell .
(lJHa
ESQ-(I111 + HZC=C—CH3 --_> HzC-C-CHz-CHrCH:
CH3
Ha
’
(I311:
2.
2, 2-dimethylpentane
CH2
CH3 CH3
H3C-—CH+ OH —-——> HsC- ——C—CH3
CH3
CH3
'H: H
2, 2, 3-trimethylbu
tane or triptane
3. , III
ElI
CH:
H|C—(]'J-CH3+H2C=C—CH:; —+ HaC-éH-CHz-CHz-CHz-CH:
CH3
Z-methylhexane
mogeneous gaseous phase alkylation catalysts, in
the alkylation of paraf?nic hydrocarbons with
ole?nic hydrocarbons, under the conditions set
forth hereinbefore.
Accordingly, it is an object of the present in
vention to provide an eflicient process for alkyl
ating isoparaf?nic or normal para?inic hydrocar
. 'bons with ole?nic hydrocarbons.
Another object
is to provide an improved process for catalytically
alkylating either normal para?lnic hydrocarbons
or isoparaf?nic hydrocarbons with ole?nic hydro
carbons. A more speci?c object is to provide a
process for catalytically alkylating normally gase
ous isopara?inic hydrocarbons with normally
gaseous ole?nic hydrocarbons, to produce high
yields of high-octane gasoline. A Very important
object is to afford a process for alkylating isobu
tane with propylene, to produce high yields of
high-octane gasoline. A further object is to pro
vide a process capable of carrying out the above
objects by using small amounts of organic halo
55 gen compounds, as alkylation catalysts, that form,
with the hydrocarbon reactants, a single, ho
mogeneous gaseous phase during the alkylation
operation. Other objects and advantages of the
present invention will become apparent to those
60 skilled in the art from the following description.
Broadly stated, our invention provides a process
for alkylating normal para?inic or isopara?inic
From a motor fuel standpoint, the 2,2-dimethyl
hydrocarbons, particularly isobutane, with ole
pentane produced by the ?rst reaction, has an
?nic hydrocarbons, particularly propylene and
octane number of about 80 CFR. motor method; 65 ethylene, which comprises contacting the par
the triptane produced by the second reaction has
af?nic and ole?nic hydrocarbons in gaseous
an octane number of well over 100, and the
2-methylhexane‘ obtained in the third reaction
has an octane number of about 45.
In view of
phase and in a reaction zone under alkylating
conditions, with small amounts of an alkylation
catalyst consisting essentially of one or more or
the foregoing, in the manufacture of high-octane 70 ganic halogen compounds, that forms with the
motor fuel by the alkylation of isobutane with
hydrocarbon reactants, a single, homogeneous
propylene, alkylation conditions that favor the
gaseous phase under the alkylation conditions of
production ‘of triptane obviously are preferable.
the reaction zone.
Further, since neohexane which may be produced
An important feature of the process of the pres
by the alkylation of isobutane with ethylene, has 75 ent invention is the fact that, contrary to the
Q,.1:.°.8.
5
However, it is likewise essential. tor the: Purposes
known catalytic. alkylationprocesses of the B15191.‘
or our process. that the organic halogen co
pounds that; are. used as alkylation catalysts in
the process of the present: invention, form. with
art which. are only capable of: alkylatingi isopar
a?inic hydrocarbons, our proqe'ssis. capable. of; a1
kylating either normal paraffinic 0r isoparaliinio
the hydrocarbon reactants being; iorocss.se<;l.;,~ a
hydrocarbons with substantially equal ease.
single, homogeneous gaseous phase underthe al
Another important feature is, the relatively low
temperature that. may bev used;
kylation, conditions or the, reaction zone.- Ali
phatic or acyclic. organic halogen compounds.
such as methyl chloracetato, chloral, aoetyl bro-.
Asia result,
degradation of the hydrocarbon reactants in the
charge to. low molecular weight hydrocarbons and
the pronounced occurrence of side, reactions, in.
cluding polymerization of the ole?nic. hydrocare
bons, are. substantially completely avoided. Con
sequently, in our process, we obtain high yields of
a. high grade product. that, is. almost. entirely: pare
ai’?nic in nature and is substantially free from
midc, dihromoethyl other, trifluoroacetio acid.
isonropyl ?uoride. diiodoethyl. other, irsobutyl
iodide. iodoiorm. dibromo-monoiodo methane.
and the. likes‘. aloicyclic organic. halogen com-.
pounds, such as ?uocyclopropane, bromocyclo;
15
impurities.
A very important feature of the. present inven
tion is the fact that, contrary to known catalytic
,alkylation processes of the prior art in which the
hydrocarbon reactants being processed .form with
the: allrylation catalysts, a heterogeneous system
duringv the alkylation operation, the alkylation
process of our invention, employs alkylation cat
‘alysts consisting essentially of materials that
form with the hydrocarbon reactants being proc
essed, a single homogeneous gaseous phase under
butane and iodocyclobutane; and aromatic hale
ogen compounds. such as p-dihrornohenzene.
benzyl iodide and benzoyl; fluoride; have been
found. to be suitable. catalysts. for the process of
our invention-v Generally speaking. the. pres
ferried catalysts: of our: invention are the. halogen
derivatives of acyclic. alioyolic, and aromatic. by?
drocarhons, particularly the cheap. and readily
available low-boiling hydrocarbons, from, meth+
ans to hyd... carbons. with 1.0 carbon atoms.
a halogen or halogens, have been sub
stituted for part or all the hydrogen of; a hydro
.alkylating conditions. The, alkylation catalysts
carbon, or ' to, a non-ring portion. if any,v of; the v
Accordingly, as a. result of the catalysts’ being in
the same phase or state as the hydrocarbon re
portion. to the ease with which they decompose
hydrocarbon. We especially prefer to use as. our
of the present invention are called, therefore, and
catalysts. halogen. derivatives of loweboi'ling
as noted hereinbefore; homogeneous gaseous
acyclic
hydrocarbons, and the tertiary halogen
phasealkylation catalysts, in contradistinction to 30 derivatives.
of low-boiling acyclic hydrocarbons
the allsylation catalysts of the. priorart which are
are among the most desirable. the cll?oienoy of
referred to as heterogeneous alkylation catalysts.
our catalysts. apparently- being somewhat in pro
actants being processed, fouling of the catalyst 35 during the alkylatiqn operations It is. understood.
of course’. that hydrogen halides and. elemental
is substantially eliminated and agitation and/or
halogens, reacting; with hydrocarbons, can be
mixing-problems are non-extant. Further, since
used to form the» organic halogen compound cat
the catalytic activity of alkylation catalysts ap
alysts-in Situ'z
. >
pears to be predicated somewhat upon contact be
The amounts. of organic halogen compounds
tween the catalysts and the hydrocarbon react 40 .used
in, our process vary between. about 0.5%
ants at the interfaces therebetween, it follows that.
and about 3%, and preferably between about 1%
the catalytic efficiency of a given catalyst in
8111.91 about. 12.5%, with respect. to. the weight. of
creases with the increase in area of interfacial
Contact, other variables remaining constant.
Hence, since the homogeneous gaseous phase al
kylation catalysts of our process inherently fur
nish the greatest possible "inter-facial contact.”
between the catalyst and the. hydrocarbon react- "
the total charge of. hydrocarbon. reactants.- It
' must be noted, however, that. larger amounts may
bev employed if desired, although no additional
advantages seem. to result therefrom.
'
The para?inic and ole?nic hydrocarbons to be
used in our process may be derived from any
ants under the conditions of alkylation, e?iciont 50 suitable source, as is well known in the art, and
catalytic activitywith a concomitant high yield
may beused either in the pure state or in admix
of high grade alkylate is achieved using relative
tore with other constituents not undesirable
ly small amounts of homogeneous. gaseous phase.
Thg para?lnic and ole?nic hydrocarbons usually
alkylation catalyst.
employed. in the preferred operation. of manufac
.In view of the foregoing, an operation teat-111's 55 tllrirlg' motor fuels, will be. the normally gaseous
off, the process of the present. invention that; is of
paraf?nic hydrocarbons, except methane and
-<.=ons.iolsrable practical importance, that small
ethane, andthe, normally gaseous ole?nic hydro
or promoter amounts of organic halogen oom
carbons, as is well understood in the art. 'Here
poundsjare used as alkylation catalysts- These
again this process has a distinct advantage over
amounts are so small that they may be. discard
many of the prior art processes, in that the ole
ed, feasibly, thereby obviating recovery and re 60 ?n
ethylene may be used for alkylating the par
generation problems and eliminating high initial
af?nic hydrocarbons. It is well known that
and operation costs.
ethylene. cannot be. used in many catalytic proc
"As disclosed in application Serial Number
esses, including the sulfuric acid process, where
‘502,018, ?led September 11, 1943; and m appli
the supply of available ole?nic hydrocarbons
cation .Serial Number 502,813, ?led September 65by
is restricted. Therefore, an important aspect of
17, 1943, a most important feature of homoge
the present invention is the fact that butane,
neous gaseous phase alkylation is’ that high yields
for
may he aikylated with ethylene
A conventional and preferred source of paraf
7o?nic and ole?nic hydrocarbons is the ?xed gases
garlic halogen compounds
obtained, around petroleum re?neries. These
As disclosed in application Serial Number ?xed
gases may furnish substantially all the de
502,018, filed September 11, 1943, the. organic
siredjpara?lnic and ole?nic hydrocarbons, or it
halogen compounds that are used as homogene
.of high-octane motor fuel are obtained by car
ryins out the alkylation in the presence of or
may be necessary or desirable to obtain addi
"phase allrylation
catalysts, may be
oils’ ease-011s, .
,,
‘solids, liquids or cases under normal. conditions. i'lo-tional supplies, as is well understood... Additional
2,410,105!
7
ole?nic hydrocarbons, if required, may be formed
from a portion of the para?inic hydrocarbons.
8
tively low during the alkylation reaction, in order‘
to eliminate as much ole?n polymerization as
On the other hand, additional para?inic hydro
possible. Accordingly, it is advisable to main
carbons may be admixed to increase the concen
tain the ole?n concentration in the charge below
tration of paraf?nic hydrocarbons to a desired 5 about 25% by volume, and preferably between
magnitude.
about 7% and about 12% by volume. In con
In carrying out our process,‘ we use temperatinuous operation, this is effected by introducing
tures varying between about 590° F- and about
the ole?nic reactant at a number of points in the
850° F., and preferably temperatures varying bereaction zone or by adding the ole?nic reactant to
tween about 650° F. and about 825° F. In the 10' a recirculating mass of excess para?inic hydro
alkylation of isobutane with propylene, however,
it was found, as disclosed in copendingappli'cation Serial Number 502,813, ?led September 17,
1943, that the best yields of desired alkylate are
carbon reactant, reaction product and catalyst.
The reaction period during which the react
850° F., and preferably, about 775° F. to about
is satisfactory.
ants are present in the reaction zone depends
upon the temperature, and to a certain extent,
obtained when the alkylation is conducted at 15 upon the pressure. Ordinarily, a reaction period
temperatures falling within about 750° F. to about
varying between 1 to 2 minutes and 1 to 2 hours
.
'
825° F. The alkylate produced under these conIt must be understood, that the reaction vari
ditions contains no more than 5% of ole?nic hyables are more or less interdependent, hence,
drocarbons and n0 aromatics so that the pre- 20 when one isarbitrarily ?xed, the limits within
dominance of alkylation obtained thereby is a
which the others may be varied, are somewhat
‘distinct feature of the process. Under apprecirestricted. In any particular instance, the most
ably higher temperature conditions, secondary redesirable conditions can be readily ascertained
actions occur that substantially reduce the purity
by one skilled in the art, the preferred ranges ofv
of the product obtained, as noted hereinbefore 25 these variables having been indicated hereinbe
in connection with thermal alkylation. In the
fore.
, alkylation of isobutane with propylene in accordance with the process of the present inven-
The alkylate product that we obtain distills
over a fairly large boiling range, but a greater
tion, it must be noted that even within the prepart of the alkylate, usually from about 85% to
ferred temperature range, side reactions occur 30 about 90%, distills in the boiling range of avia
that account for substantial portions of the total
tion gasolines. The iodine number of the avia
alkylate, but a fraction boiling at 79° C. to 82° C.
tion distillate is low, on the order of about 5 to
and consisting of 15 parts of triptane to 85 parts
10. As mentioned ' hereinbefore, the alkylate
of 2,2-dimethylpentane may be obtained.
product consists predominantly of branched par
The pressure to be used in our process may 35 a?inic hydrocarbons.
'
‘
'
vary from about 500 pounds per square inch to
about 6000 pounds per square inch or more, and
Numerous experimental data could be adduced
to indicate the results obtainable by employing
preferably from about 2500 pounds per square
inch to about 6000 pounds per square inch for
the homogeneous gaseous phase catalysts of the
present invention, but the following examples
the alkylation of isobutane with propylene, the 40 are su?iciently characteristic:
, Run 1
Run 2
Per cent by weight of isobutane in charge _______ __
Per cent by weight of propylene in charge _______ __ l0
Per cent by weight of ethylene in harge__
‘
Run3
Run 4
92.82 ______________ __ 88.9.
.................... __ 9.9.
5.6 ________________ -_
_
p-Dibromobenzene__ Isopropyl?uoride;
Catalyst _________________ V
Per cent of catalyst by wcig
1.58 _______________ __
1.2.
-
1
Contact time in minutes. _ _
Residence time in minutes. _ __
Temperature, ° F ___________ __
____
Pressure, lbs/sq. in. gauge___-_ ___________________ __
Per cent yield of alkylate based on weight of ole?ne.
Per cent yield of alkylate based on weight of charge
Per cent triptane in 76—86° 0. fraction of a1kylate_
Per cent neoliexane fraction (44-54“ C.) in alkylate.
most suitable pressure being more or less de—
. The alkylate produced by our process is con
pendent upon the particular temperature in__ 55 taminated by various halogen compounds‘ which
volved. In general, the higher the pressure, the
are present in small concentration. These com
higher the yield of alkylate. Accordingly, the
pounds cause a negative susceptibility to tetra
criterion for establishing an upper limit to the
ethyl lead, and therefore, should be removed.
~pressure range used is primarily the feasibility
Removal of the halogen compounds is possible in
vof maintaining such pressure.
(3O a variety of ways, as set forth in copending appli
The process may be carried out as a batch,
continuous or semi-continuous type of operation.
Particularly when the process is carriedout on
a commercial scale, economic considerations
make it preferable to operate in a continuous
manner. For efficient operation, whether the
cations Serial Number 477,450, ?led February 27,
1943; Serial Number 502,504, ?led September 15,
1943; and Serial Number 504,436, ?led September
a 30, 1943.
This application is a continuation-in-part of
process is carried outon a batch or continuous
' our copending application Serial Number 502,018,
?led September 11, 1943.
(
basis, it is essential that the hydrocarbon re
actants be intimately contacted with the homo
‘ other speci?c forms without departing from the
geneous gaseous phase catalysts of our inven- '
tion.
This may be effected in several ways, asis
well known in the art.
,
'
1
‘
In our process it is desirable, as in‘ known
isopara?in-ole?n alkylation processes, to'keep the
The present invention, may be embodied in
spirit or essential attributes thereof, and it 'is
therefore desired that the present, embodiments
be considered in all respects as illustrative and
not restrictive, reference being had to the ap
pended claims rather than to the‘ foregoing de
concentration of the ole?nic hydrocarbons rela-" 75 scription to indicate the scope of the invention.
2,410,108
9
We claim:
1. The process of manufacturing triptane,
which comprises contacting isobutane and pro
pylene in gaseous phase in a reaction zone under
alkylating conditions including a temperature
varying between about 775° F. and about 825° F.
and a pressure in excess of 2500 pounds per
square inch, with an alkylation catalyst consist
10
ly gaseous ole?nic hydrocarbon, a single, homo
geneous gaseous phase under said alkylating con
ditions, in amounts of at least about 0.5% by
weight based on the total weight of said normally
gaseous para?inic hydrocarbon and said normal
ly gaseous ole?nic hydrocarbon, and maintaining
said normally gaseous paraflinic hydrocarbon in
excess over said normally gaseous ole?nic hydro
carbon in said reaction zone so that alkylation is
ing essentially of material selected from the
group consisting of acylic organic halogen com 10 the principal reaction.
12. The process of claim 11 wherein the alkyla
pounds, alicyclic organic halogen compounds,
tion catalyst consists essentially of a halogen de
and aromatic organic halogen compounds, that
rivative of a hydrocarbon.
forms with said isobutane and said propylene, a
13. The process of claim 11 wherein the alkyla
single, homogeneous gaseous phase under said
alkylating conditions, in amounts of at least 15 tion catalyst consists essentially of a halogen de
rivative of a low-boiling hydrocarbon.
about 0.5% by weight based on the total weight of
14. The process of claim 11 wherein the alkyl
said isobutane and said propylene, and main
ation catalyst consists essentially of a ?uorine
taining said isobutane in excess over said pro
derivative of a low-boiling acyclic hydrocarbon.
pylene in said reaction zone so that alkylation is
15. The process of claim 11 wherein the alkyl
the principal reaction.
.20
ation catalyst consists essentially of an iodine
2. The process of claim 1 wherein the alkyla
derivative of a low-boiling acyclic hydrocarbon.
tion catalyst consists essentially of a halogen
16. In a process of alkylating a paraffinic hy
derivative of a hydrocarbon.
drocarbon with an- ole?nic hydrocarbon, which
3. The process of claim 1 wherein the alkyla
tion catalyst consists essentially of a halogen 25 includes reacting a para?‘lnic hydrocarbon with
an ole?nic hydrocarbon in a reaction zone under
derivative of a low-boiling hydrocarbon.
alkylating conditions, in the presence of an
4. The process of claim 1 wherein the alkyla
alkylation catalyst; the improvement which com
tion catalyst consists essentially of a ?uorine
prises contacting said para?inic hydrocarbon and
derivative of a low-boiling acylic hydrocarbon.
5. The process of claim 1 wherein the alkyla 30 said ole?nic hydrocarbon in gaseous phase in a
reaction zone under alkylating conditions in
tion catalyst consists essentially of an iodine de
cluding a temperature varying between about
rivative of a low-boiling acylic hydrocarbon.
590° F. and about 850° F. and a pressure in ex
6. The process of manufacturing high-octane
gasoline, which comprises contacting isobutane
cess of 500 pounds per square inch, with an alkyl
and propylene in gaseous phase in a reaction zone 35 ation catalyst consisting essentially of material
selected from the group consisting of acyclic or—
under alkylating conditions including a tempera
ganic halogen compounds, alicyclic organic halo
ture varying between about 750° F. and about
gen compounds, and aromatic organic halogen
850° F. and a pressure in excess of 2500 pounds
compounds, that forms with said paraf?nic hy
per square inch, with an alkylation catalyst con
sisting essentially of material selected from the 40 drocarbon and said ole?nic hydrocarbon, a single,
homogeneous gaseous phase under said alkylat
group consisting of acyclic organic halogen com
pounds, alicyclic organic halogen compounds,
ing conditions, and maintaining said parai?nic
and aromatic organic halogen compounds, that
hydrocarbon in excess over said ole?nic hydro
carbon in said reaction zone so that alkylation
forms with said isobutane and said propylene, a
single, homogeneous gaseous phase under said 45 is the principal reaction.
17. The process of claim 16 wherein the alkyl
alkylating conditions, and maintaining said iso
ation catalyst consists essentially of a halogen
butane in excess over said propylene in said reac
derivative of a hydrocarbon.
tion zone so that alkylation is the principal re
18. The process of claim 16 wherein the alkyla
action.
’7. The process of claim 6 wherein the alkyla 50 tion catalyst consists essentially of a halo-gen
derivative of a low-boiling hydrocarbon.
tion catalyst consists essentially of a halogen de
rivative of a hydrocarbon.
8. The process of claim 6 wherein the alkyla
19. In the process of alkylating a para?inic
hydrocarbon with an ole?nic hydrocarbon, which
includes reacting a para?inic hydrocarbon with
tion catalyst consists essentially of a halogen de
rivative of a low-boiling hydrocarbon.
55 an ole?nic hydrocarbon in a reaction zone under
alkylating conditions, in the presence of an alkyl
9. The process of claim 6 wherein the alkyla
ation catalyst; the improvement which comprises
tion catalyst consists essentially of a ?uorine de
contacting said paraf?nic hydrocarbon and said
rivative of a low-boiling acyclic hydrocarbon.
ole?nic hydrocarbon in gaseous phase in a re
10. The process of claim 6 wherein the alkyla
tion catalyst consists essentially of an iodine de 60 action zone under alkylating conditions, with
an alkylation catalyst consisting essentially of a
rivative of a low-boiling acyclic hydrocarbon.
?uorine derivative of a low-boiling acyclic hydro
11. The process of manufacturing high-octane
carbon, that forms with said para?inic hydro
gasoline, which comprises contacting a normally
carbonand said ole?nic hydrocarbon, a single,
gaseous parai?nic hydrocarbon and a normally
gaseous ole?nic hydrocarbon in gaseous phase in 65 homogeneous gaseous phase under said alkylat
a reaction zone under alkylating conditions in- '
ing conditions, and maintaining said parai?nic
cluding a temperature varying between about
hydrocarbon in excess over said ole?nic hydro
650° F. and about 825° F. and a pressure in excess
of 1500 pounds per square inch, with an alkyla
carbon in said reaction zone so that alkylation
is the principal reaction.
20. The process of claim 19 wherein the alkyl
tion catalyst consisting essentially of material 70
ation catalyst consists essentially of an iodine
selected from the group consisting of acyclic
derivative of a low-boiling acyclic hydrocarbon.
organic halogen compounds, alicyclic organic
ALEXANDER N. SACHANEN.
halogen compounds, and aromatic organic halo
ARLIE A. O’KELLY.
gen compounds, that forms with said normally
CLAUDE G. MYERS.
gaseous para?inic hydrocarbon and said normal 75
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