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2,406,776
Patented Sept. 3, 1946
UNITED‘ STATES2,406,776PATENT OFFICE
CATALYTIC ALKYLATION PROCESS
James B. Kirkpatrick, Woodbury, N. J., John J.
Somers, Philadelphia, Pa., and Alexander N.
Sachanen, Woodbury, N. J.,‘ assignors to
Socony-Vacuum Oil Company, Incorporated, a
corporation of New York
No Drawing. Application October 28, 1943,
Serial No. 508,062
19 Claims.
(Cl. 260—683.4)
2.
1
This invention relates to the alkylation of
atures and pressures, on the order of over 900° F.
para?inic hydrocarbons with ole?nic hydrocar
and over 4000 pounds per square inch gauge, re
bons and is more particularly concerned with the
production of high octane motor fuel by the
spectively; or may be conducted in the presence
of alkylation catalysts, at lower temperatures and
catalytic alkylation of para?inic hydrocarbons
pressures, thereby assuring a high yield of de
sired alkylate by avoiding extensive degradation
with ole?nic hydrocarbons.
It is well known in the art to polymerize ole
of the reactants, the occurrence of side and sec
?nic hydrocarbon gases to produce motor fuels
ondary reactions, and appreciable polymerization
of the ole?nic reactant. The two methods are
having constituents of an unsaturated character.
Various commercial processes have been proposed 10 known as thermal alkylation and as catalytic al
kylation, respectively.
I
'
for ultimately effecting the desired polymerization
Several methods are known for the catalytic
of the ole?nic hydrocarbons. These processes have
alkylation of isoparaf?nic hydrocarbons with ole
been predicated upon the dictates of the chemical
?nic hydrocarbons. For instance, it is known to
nature of the stocks available as well as engineer
ing considerations such as initial and operation 15 alkylate isopara?inic hydrocarbons with ole?nic
hydrocarbons in the presence of sulfuric acid, ~
costs; their essential feature being that in the
phosphoric acid, metal phosphates, metal halides,
course of treating the materials, the ole?nic hy
activated clays and the like, as catalysts. In
drocarbons produced in the earlier stages of the
these catalytic alkylation processes, the hydro
process, are eventually polymerized to gasoline.
Accordingly, hydrocarbon gases may be passed 20 carbon reactants form with the alkylation cata
lysts, a heterogeneous system during the alkyla
along with cracking stock or naphtha through
tion operation, Since under alkylation condi
a cracking still to crack and polymerize such
tions, the catalytic activity of the alkylation
gases to gasoline simultaneously with the crack
catalysts appears to be predicated upon contact
ing or reforming, or parai?nic hydrocarbon gases
may be separately cracked to ole?nic hydrocar 25 between the catalysts and the gaseous hydrocar
bon gases and these gases are subsequently passed
bon reactants at the interfaces therebetween, in
these processes, the catalysts are used in amounts
with naphtha through a polymerizing and re
varying between 10% and'200% by weight, on
forming still. In some instances, the processes
the charge, depending on the catalyst used. Due
involve the use of catalysts for facilitatingthe
30 to these comparatively high amounts, where pos
cracking and/or polymerization operations. ~ ~ '
slble, recovery and regeneration of the catalyst
It is also well known in the art, to combine
have been proposed. This, of course, involves
paraf?nic hydrocarbons directly with ole?nic hy
high initial and operation costs. Further, it is
drocarbons by processes broadly called alkylation
also known that certain substances called pro
processes, to produce motor fuels having constit
uents of saturated character. In alkylation proc 35 moters, promote the catalytic action of these al
kylation catalysts. Accordingly, several proc
esses, a charge comprising a mixture oi a par
esses have been proposed wherein small amounts
a?inic hydrocarbon, called the para?inic react
of these promoters, on the order of about 1%
ant, and an ole?m'c hydrocarbon, called the ole
to 3% by weight on the charge, are added to the
?nic reactant, is subjected to high temperature
and pressure to produce a saturated alkylate 40 catalysts to promote their alkylation catalytic
product.
Since conditions of alkylation ' also
activity.
A copending application, Serial Number
502,018, ?led September 11, 1943, in which one
of the inventors of the present application is
tration of the ole?nic reactant in the charge.
The only limit to the pressure used appears to be 45 coinventor, is directed to the process of alkylat
ing para?'inic and isopara?inic hydrocarbons
the feasibility, of maintaining high pressures; On
with ole?nic hydrocarbons, which comprises con
the other hand, the temperature used is limited
tacting a para?inic or isopara?inic hydrocarbon
by degradation of the hydrocarbon reactants in
and an ole?nic hydrocarbon in a reaction zone
the charge to low molecular weight hydrocar
bons, and the occurrence of side reactions, in 50 under alkylating conditions, with small or pro
motor amounts of what has been termed therein,
cluding polymerization of the ole?nic reactant
a homogeneous gaseous phase alkylation cata
under high temperature conditions, that sub
stantially reduce the purity of the product ob
lyst consisting essentially of a material that
forms with the hydrocarbon reactants, a single,
cause polymerization of the ole?nic reactant, it
is necessary to maintain a relatively low concen
tained.
I
p
‘
‘
Alkylation may be conducted ‘at high temper
55 homogeneous gaseous phase under the alkylation
2,406,776
3
659°
it
which are the predominant constituents of the
alkylate obtained in the alkylation of isobutane
with propylene in the presence of heterogeneous
alkylation catalysts, have octane numbers of 89
and 82, respectively, the importance of the al~
kylation of isobutane with propylene in the pres
ence of homogeneous gaseous phase catalysts
under alkylation conditions that favor as pro
duction of triptane is manifest. It was also
found that in actual practice, it was impossible
conditions of the reaction zone. The alkylation
conditions of the process of this copending ap
plication, comprise a broad temperature range of
about 590° F. to about 850° F., preferably, about
. to about 825° F., and pressures or at least
500 pounds per square inch gauge, preferably, at
least 1500 pounds per square inch gauge.
Another copending application, Serial Number -
502,813, ?led September 17, 19¢i3, is directed to
the process of alkylating isobutane with propyl
ene, which comprises contacting isobutane with
to obtain triptane exclusively,
amounts of 2,2-dimethylpentane
propylene in a reaction zone under closely con
appreciable
2~methyl~
- hexane being always formed.
trolled alkylating conditions, with promoter or
The speci?c classes of homogeneous gas-ecu
small amounts of the homogeneous gaseous phase
catalysts broadly disclosed in the copending ap 15 phase catalysts claimed in the above-noted co—
plication referred to hereinabove, the closely
controlled alkylating conditions including a team--‘
, bromides.
perature range of about 750° F. to about850_° F.,
We have found that organic
compounds
preferably, about 775° F. to about 825° F., and
are suitable homogeneous gaseous phase allzylan
pressures of at least 2500 pounds per square
inch gauge. In the alkylation of isobutane with
propylene in the presence of homogeneous gase
ous phase catalysts, it was found that the alkyl
ate obtained included constituents that are en
tion catalysts and that isoparo
af?'nic hydrocarbons may be effic
'
:15? a
with ole?nic hydrocarbons to produce high yields
of high octane gasoline by using small or pro
tirely different from the constituents of the hy 25 moter
form with
amounts
the hydrocarbon
of organic nitro
reactants,
compounds
a single,
drocarbon alkylate obtained in the alkylation of
homogeneous gaseous phase during the alkyla~
isobutane with propylene in the presence of
tion operation.
known heterogeneous alkylation catalysts, i. e.~,
-We have also found that organic nitro com‘
AlCls, H2304, and the like. Thus, when hetero
pounds are suitable homogeneous gaseous phase
geneous alkylation catalysts are used, 2,3-di
catalysts in the catalytic alkylation of ‘sobntane
methylpentane and 2,4-dimethylpentane are im
with propylene under the controlled condition" of
portant constituents of the hydrocarbon alkylate
obtained. On the other hand, triptane or 2,2,3
alkylation
tion,
Serial described
Number 502,813,
in the copending
?led September
apt," 1'7,
trimethylbutane, 2,2-dimethylpentane, and 2
methylhexane are the predominant constituents
of the hydrocarbon alkylate, when gaseous phase
1943. -
It is an object of the present invention to- pro
vide an efiicient process for cataiytically alhylab
ing isopara?inic o-r parafiinic hydrocarbons with
homogeneous alkylation catalysts are employed.
In this copending application, the formation of
ole?nic hydrocarbons.
these three compounds was postulated as follows:
Another object of the
present invention is to provide an e?icient process
for catalytically alkylating either normal par
af?nic hydrocarbons or isopara?inic hydrocar
bons with ole?nic hydrocarbons to produce high
yields of highoctane gasoline. A more spe
u
' object is to provide a process for catalyticaiiy
alkylating isobutane with propylene to produce
Isobutane Propylene
'
>
-
2,2,3-trimethylbutane
or triptane
"50
high-yields of high octane gasoline. A very im
portant 'object of the present invention is to
aiTord a process capable of carrying out the above
objects by using small or promoter amounts of
organic’nitro compounds that form with the
hydrocarbon reactants, a single, homogeneous
gaseous phase during the alkylation operation.
Qther objects and advantages of the present iii
55 vention Will become apparent to those skilled in
the vart from the following description.
Broadly stated, our invention provides a process
forialkylating normal paraf?nic or isopara?inic
hydrocarbons, particularly isobutane, with ole
V60 ?nic hydrocarbons, such as ethylene, propylene,
and butylenes', which comprises contacting the
From a motor fuel standpoint, the 2,2-di~
methylpentane produced by the first reaction,
para?inic and ole?nic hydrocarbons in gaseous
has an octane number of about 80 CF t motor
method; the triptane produced by the second
reaction has an octane number of well over 100,
and the Z-methylhexane obtained in the third
reaction, has an octane number of about 45.. In
View of the foregoing, in the manufacture of high
octane motor fuel by the alkylation of isobutane'
with propylene, alkylation conditions that favor
the production of triptane obviously are prefer
able. Further, since neohexane which may be
produced by the alkylation of isobutane with
ethylene, has an octane number of 93.4, and since
2,3-dime’thylpentane' and‘; v2',ll-dimethylpentane
phase and in a reaction zone under alkylating
conditions, with small or promoter amounts of an
alkylation catalyst consisting essentially of or
ganicv nitro‘ compounds, particularly nitro meth
ane, that forms with the hydrocarbon reactants,
a 'sin’glehomogeneous gaseous phase under the
alkylation conditions of the reaction zone.
'
1~ ‘An important feature of the process of the
present invention is the fact that, contrary to
the known catalytic alkylation processes of the
prior'ar't which are only capable of alkylating iso
para?inic hydrocarbons, our process is capable
a of- alkylating- either normal para?inic
or isopar
2,406,776
.6
a?inic, hYdQI'QQaIbODSQ ‘with Substantially equal '
ease.~,
t.
'
,
a
homogeneous gaseous. phase, alkylation . catalysts
ofthe- present invention are nitro derivatives of
hydrocarbons, and. particularly, nitro derivatives
,
Another important vfeature of, the process of
the present invention is .the relatively‘rlow tem
of hydrocarbons wherein the nitro group is sub- ,
perature that may bemused. _ .As a result, degrada
5 stituted onto anon-ring portion, if any, of the
tion of the hydrocarbon reactants in the charge to
low molecular weight hydrocarbons and'the proj
nounced occurrence ofbside reactions including
polymerization of the oleiinic hydrocarbons, are
substantially completely‘ avoided. Consequently,
10
in our process, we obtain highfyields of a high
hydrocarbons. 7, It is to be understood, herein,
that by nitro “derivatives” of hydrocarbons, we
mean compounds wherein all the. hydrogen has
been substituted ‘by the nitro group, or com
pounds wherein only partof the hydrogen has
been substituted, as well as compounds wherein
grade'product'that is almost entirely paraliinic
innature and issubstantially free ‘from im
part, of theuhydrogen'hasr been substituted by
thenitro group and part of :the hydrogen has
been. substituted by halogens, particularly chlo
\r ‘A very important ‘feature ofthe present in 15 rine and bromine. We especially prefer touse
vention is the fact that, contrary to known cata
as .our ,homogeneous gaseous. phase . alkylation
lytic processes of the prior art 1n-Whlch the hy-~
catalysts,‘ nitrov..d'erivatives of light paraf?nie hy-,
drocarbon reactants beingprocessed form with
drocarbons, in view of their volatility at moderate
the alkylation catalysts, aheterogeneous system
temperatures. Thus,at the present time, we con
during the alkylation operation, the alkylation 20 sider ._rnitromethane, nitropropane, . 1.-nitro-'-1
process of‘ our inventionvemploys alkylation cata
chloropropane, and nitrobenzyl typical examples
lysts consisting essentially of materials that form a
of .the ‘homogeneous gaseous phase alkylation
purities.‘
-
'i
a
1
I
with the hydrocarbon reactants being processed, a
single, homogeneous gaseous phase under alKylat
ing conditions.
catalysts ofour invention. It is to be understood, .
of course, that the homogeneous gaseous phase
The alkylation catalysts 0f the 25 alkylation catalystsof 'our invention, may be
present invention may be called, therefore, homo
geneous gaseous phase catalysts in contradis
tinction to the alkylation catalysts of the prior
formed in: situ. This may be, done by injecting
thelproper amount of nitric acid into the mixture
to be treated. Under the ‘temperatures used in
art winch may be referred to as heterogeneous ~
our process, aliphatic hydrocarbons ofv low mo
catalysts. fAcco'r‘dingly, as a result of thecata
lecular weight will be nitrated to produce the
'
'
'
~30
lyst’s being‘in the same phase or state as the
catalysts of our invention.
hydrocarbon reactants being processed, fouling of
The amount oforganic nitro compounds used
in our process, varies between about 0.5% and
the catalyst'is substantially elimmated and agita
tion and/or‘ mixing problems are non-extant.
'
about 3%, and preferably, between‘ about 1%
li‘urther, since the catalytic activity of allrylation
35, and about 1.25%, with respect to the total charge
catalysts appears to be predicated somewhat upon
‘contact between the catalysts and the gaseous
hydrocarbon reactants at the interfaces therebe
of hydrocarbon reactants. It must be noted, how
ever, that larger amounts of organic nitro com
pounds may-‘be employed ‘if desired, although no
tween, it follows that the catalytic eniciency of a
given catalyst increases with the increase in area 40
of interfacial contact, other variables remaining
constant. Hence, since the homogeneous cata
additional advantages result therefrom. '
The paraflinic and. ole?nic hydrocarbons to‘ be
used in our process may be derived from any suit
able'source, as is well known in the art, and may
be used either in the pure state or in'admixture
possible “interracial contact” between the cata
with other. constituents not undesirable. The
lyst and the hydrocarbon reactants under the 45 paraf?nic and ole?nic hydrocarbons usually em
conditions of-alkylation, e?icient catalytic activ
ployed in the preferred operation of manufactur
ity with a concomitant high yield of high grade
ing motor fuels will be the normally gaseous par
alkylate is achieved using relatively small
a?inic hydrocarbons, except methane and ethane,
lysts or our process inherently furnish the‘ greatest
amounts of homogeneous gaseous phase catalyst.
and the normally gaseous ole?nic hydrocarbons,
In View of the foregoing, an‘ operation feature 50 as, is well understood in the art. Here again our
of the process of the present invention that is
process has a distinct advantage over many of the
of considerable practical importance is that small
prior art processes in that the ole?n ethylene may
or promoter amounts of organic nitro compounds 7
be used for alkylating the para?inic hydrocar
are used as alkylation catalysts. These amounts
bons. It is well known that ethylene cannot be
are so small that they may be discarded feasibly, '55 used in many catalytic processes, including the
thereby obviating recovery and ‘regeneration
problems and eliminating high initial and opera
tion costs.
.
V
sulfuric acid process, whereby the supply of avail
able ole?nic hydrocarbons is restricted. . There
fore, an important aspect of the present inven
'
A' most important feature of the present in
vention is that high yields of high octane motor
fuel are obtained by alkylating' isobutane with
propylene in the‘ presence of organic nitro com
tion is the fact that butane, for instance, may be‘
"60 alkylated with ethylene.
-
_
r
.
.
A'conventional and preferred source of paraf
?nic and ole?nic hydrocarbons is the ?xed gases
pounds, particularly, nitro methane and nitro
obtained around petroleum re?neries. These
?xed gases may furnish substantially all the de
'As disclosed in application Serial ililumber '65 sired paraf?nic‘ and ole?nic hydrocarbons, or it
r propane.
1
'
502,018, ?led September 11,1943, the homogeneous
gaseous phase alkylation catalysts of" the present
_ invention'may be solids,_liquids or gases under "
maybe necessary or desirable to obtain additional
supplies, as is well understood. Additional ole
?nic hydrocarbons, if required, may be formed
frorn'a portion’of the para?inic hydrocarbons:
normal conditions. However, it is likewise essen-.
,tial for the purposes of ouroprocess, that the 70 On the other hand, additional para?inic hydro
carbons may be admixed to increase theconcen-V
organic vnitro compounds form with the . hydro
tration' of‘ para?inic hydrocarbons to'a desired f
carbon reactants being processed, a, single, homo- I
geneous gaseous phase under, the alkylatiorla'co‘n
magnitude.
NV
v
’
> \ _In-' carrying} out our’ I process, we a use '_ tempera-"i
ditionsgpf the. process. gGenerallyj'speaking, the; 75 turesiva'rying between about 590?
andabout“
2,406,776
7
.
8
uct. obtained when’ the» alkylation is carried out in
850‘? R, and preferably temperatures varying be
the presence of nitromethane, is highly para?inic,
tween about 650° F. and about 825°- F. In the» al
i. e., his the result of alkylation, whereas the
kylation of isobutane with propylene, howeverywe
cation Serial Number 502,813, ?led September 17,
product-of the non-catalytic process is highly ole
?nic, i. e.,,it is the result of polymerization.
1943, that the best yields of desired alkylate are
obtained when the alkylation is conducted at tem
, rs'obutane. tas‘aizyjl'asayaa propylene in a
have found, as disclosed in the copending appli
"
peratures falling within about I750" F..:to about
'
'
‘
'
Ewampzez
'
continuous operation, in a pipe still at 775°. F. to
850° F., and preferably, about 775° F. to about 825°
F. .The allzylate produced under these conditions 10 890° .F. andunder _a..pressure of 6000 pounds per
square inch...$i,x and a half inches of isobutane
contains nomore than 5% of ole?nic hydrocar
per one moleoitmnrlepe were employed. ,' The
bons. and no aromatics so that the predominance
process ‘was. carriedout nonecatalytically, and
of alkylation obtainedthereby is a distinct fea
catalytically in the presence of 1.2% by weight on
ture of. the process. .Under appreciably higher
the
chargelof nitromethane. Theresults were as
temperature conditions,- side reactions occur that
substantially. reduce thepurity of theproduct ob
follows;
,
_
.
.
.
tained. . In the alkylation. of .isobutane with pro;
Hymn or
pylene in accordance with the process of the pres
ent. invention, itmust be noted that even. within
'1
i _. alkylate
_> ' t,’
the.~,.preferred temperature range, side ‘reactions
occurthat account for substantial portions. of- the
20
.
l a‘:
' "
‘ ‘with respect
~95 H”- >
I
.
.
r
.
glsgfirg‘éf
Iodine num
élkylatei
berqfg-lkyhte
>-
--/F0Dml3%1?n°v
boiling
up v "gmilé?
‘1,?’
percen'oy
l
o »‘
,
..
weight-H.
to 400s r. .
.
.
total alkylate, but a fraction boilingat'IQ‘F C. to '
82° C. andconsistingof. l5'parts of triptane to 85
partsof 2,2-di1nethylpentane may be obtained.
None’ _- _______
'
pro
Nitromethana“
.
0; 760
97.0
.
.
..
0.70
‘
.
'
.
'
.
n
g
The pressure to be used in our process may vary 25
from about 500 pounds per square inch to about
' The results ‘show as in Example‘ 1, that" the
6000 pounds per square inch or more, and pref
catalytic process forms a much "greater yield of
reaction product which isv substantially paraffinic,
erably, from about 2500 pounds-per square inch,
to about 6000 pounds per. square ,inch for the al
whereas'the non-catalytic process forms a prod
lrylation of isobutane with propylene, the most 30 net-with high‘ olennic content; "In addition, the
narrow fraction of‘ the alkylate boiling'between
suitable pressure being. more or less dependent
upon the particular temperature involved. In
‘79° C. and 82° 0;, showed the presence‘ of'15%
triptane in’ the catalytic allrylate, whereas this
general, the higher the pressure, the higher the
hydrocarbon was substantially absent'in the same
yield of ,alkylate. Accordingly, the criterion for
establishing an upper limit to the pressure range 35 fractionmin the non-catalytic product.
used is primarily the, feasibility of maintaining
Although‘the present invention has been 'de
scribed. in'conjunction vwith preferred embodi
ments-ii; is to~be understood that modi?cations
and-variations may be resorted to without depart
such pressure.
In our process it is desirable, as in known iso-.
paraffin-ole?n alkylation processes, to keep the
concentration of the ole?nic hydrocarbons rela
tively low during the alkylation reaction in order
to eliminate as much ole?n polymerization as pos
sible. Accordingly, it is advisable to maintain the
ole?n concentration in the charge below about
'
25% by volume, and preferably between about 45
ed claims.
>
We. claim:
'
.
a
>
-
a 1. In a process of manufacturing triptane by
7% and about 12% by volume.
,
The alkylate product that We obtain distills over
a fairly large boiling range, but a greater part
alkylating isobutane with propylene'in a reaction
zone under alkylating conditions and in the pres
of the alkylate, usually from about 85% to about
90%, distills in the boiling range of aviation gaso~
lines. The iodine number of the aviation distillate
is low, on the order of about 5 to 10.
ing from the spirit’ and scope of the invention; as
those-skilled in the art- will readily understand.
Such variations and modi?cations are considered
to be within the purview and scope of the append;
ence _ oiv catalytic material;
the improvement
which comprises contacting said isobutane and
said propylene in said reaction zone under alkyl
ating conditions including a temperature varying
As men- '
tioned hereinabove, the alkylate product consists
predominantly of branched para?inic hydrocar
between about 775° F. and about 825° F. and a
pressure of at least 25.00.pounds per square inch,
.55 with an alkylation catalyst consisting» essentially
.
Example 1
of nitromethane, in amountsv varying between
about 1% and about 1.25% of the charge, and
Commercial butane was alkylated with ethylene
controlling the concentration of the propylene so
bons.
.
in a bomb at 700° F., under a pressure of 3200
that alkylation is the principal reaction. 1
pounds per square inch, for 30 minutes, non-cata
lytically and catalytically in the presence of 1.2% "
by weighton the charge, of nitromethane. The
results were, as follows:
Yield of
Cataly St
V
i
alllrylate
respec t
wit
to ethylene,
(got‘illlilgl?sg
pczvcgg?tby
to 400° F_
None__..;_; __________ __
34
0. 740
Nitromcthane ____ -_,_..._
124
0. 690
blodiiiennulm
er'o a y ate
boiling up
V 2’. The process of _manufacturing high-octane
gasoline which comprises contacting a light par
af?nic ‘hydrocarbon and a light ole?nic hydrocar
bon in a reaction zone under alkylating condi
tions including. a temperature varying between
65 about 650° F.- and about 825° F. and a pressure of
at least 1500 pounds per square inch, with an
alkylation catalyst consisting essentially of nitro-.
to 400 F.
methane, and controlling the concentration of
the light ole?nic reactant so that alkylation is
65.
4
the principal
reaction.
’
'
v
‘ 3. The process of claim 2 wherein the alkyl
ation-catalyst consists essentially of 1-nitro-1
The results show that the catalytic process '
forms a much greater yield of reaction product,
chloropropane.
'
a
-
,4. .The. process > of~a1kylating isobutane with
Further, theiodine numbers show that theprod-; ‘>75 propylenewhich comprises contacting said iso
2,406,776
'10
9
rial; the improvement which comprises contact
butane and said propylene in ‘a reaction ‘zone
under alkylating conditions, including a temper
ing said isobutane and said‘ propylene in gaseous
phase and in said reaction zone under. alkylating
‘conditions including a temperature varying be
ature varying between about 750° Rand about
850° F. and a pressure of at least 2500 pounds per
square inch, with an alkylation catalyst consist
tween about 750° F. and about 850° F. and a
ing essentially of nitromethane, and controlling
the concentration of the propylene so that alkyl
ation is the principal reaction.
5. The process of claim 4 wherein the alkyl
ation catalyst consists essentially of l-nitro-l 10
chloropropane.
‘
6. In a process of manufacturing high-octane
gasoline by alkylating isobutane with propylene
pressure of at least 2500 pounds per square inch,_
with an alkylation‘catalyst consisting essentially
of an organic nitro compound which forms with
said isobutane and said propylene, a single, homo
geneous gaseous phase under said alkylating con
ditions, and controlling the concentration of the
propylene so that alkylation is the principal re
action.
12. The process of claim 11, wherein the al
in a reaction zone, under alkylating conditions
and in the presence of catalytic material; the 15 kylation catalyst consists essentially of a nitro
improvement ‘which comprises contacting said
derivative of a light paraf?nic hydrocarbon.
13. In a process of manufacturing high-octane
isobutane and said propylene in said reaction
gasoline by alkylating a light parai?nic hydro
zone under alkylating conditions including a tem
perature varying between about 775° F. and about ‘ carbon with a light ole?nic hydrocarbon in a
825° F. and a pressure of at least 2500 pounds per 20 reaction zone under alkylating conditions and
in the presence of catalytic material; the im
square inch, with an alkylation catalyst con
provement which comprises contacting said light
sisting essentially of nitromethane, and ‘con
para?inic hydrocarbon and said light ole?nic hy
trolling the concentration of the propylene so
that alkylation is the principalreaction.
drocarbon in gaseous phase and in said reaction
7. The process of alkylating a para?inic hydro
25 zone under alkylating conditions including a
carbon with an ole?nic hydrocarbon, which com
temperature varying between about 650° F. and
prises contacting said para?inic hydrocarbon and
about 825° F. and a pressure of at least 1500
pounds per square inch, with an alkylation cat
alyst consisting essentially of an organic nitro
said ole?nic hydrocarbon in a reaction zone under
alkylating conditions including a temperature
varying between about 590° F. and about 850° F. 30 compound which forms with said light para?inic
hydrocarbon and said light ole?nic hydrocarbon,
and a pressure of at least 500 pounds per square
a single, homogeneous gaseous phase under said
inch, with an alkylation catalyst consisting essen
alkylating conditions, and controlling the concen
tially of nitromethane, and controlling the con
tration of the light ole?nic reactant so that al
centration of the ole?nic reactant so that alkyl
.
'
ation is the principal reaction.
'
35 kylation is the principal reaction.
14. The process of claim.13 wherein the al
8. In a process of manufacturing triptane by
kylation catalyst consists essentially of a nitro
alkylating isobutane with propylene in a reaction
derivative of a light para?inic hydrocarbon.
zone under alkylating conditions and in the pres
15. The process of manufacturing high-octane
ence of catalytic material; the improvement
which comprises contacting said isobutane and 4.0 gasoline, which comprises contacting isobutane
and propylene in gaseous phase and in a reaction
said propylene in gaseous phase and in said re
zone under alkylating conditions including a tem
action zone under alkylating conditions including
perature varying between about 775° F, and
a temperature varying between about 775° F. and
about 825° F. and a pressure of at least 2500
825° F. and a pressure of at least 2500 pounds per
square inch. with an alkylation catalyst consist 45 pounds per square inch, with an alkylation cat
alyst ‘consisting essentially of an organic nitro
ing essentially of a nitro derivative of a light
compound which forms with said isobutane and
para?‘inic hydrocarbon which forms with said iso
said propylene, a single, homogeneous gaseous
butane and said propylene. a single, homogeneous
phase under said alkylation conditions, and con
gaseous phase under said alkylating conditions, in
amounts varying between about 1% and about 50 trolling the concentration of the propylene so
that alkylation is the principal reaction.
1.25% of the charge, and controlling the concen
16. The process of claim 15 wherein the al
tration of the propylene so that alkylation is the
principal reaction.
kylation catalyst consists essentially of a nitro
derivative of a light paraf?nic hydrocarbon.
~
9. The process of alkylating a light paraf?nic
hydrocarbon with a light ole?nic hydrocarbon, ' 5
whichcomnrises contacting said light para?inic
hydrocarbon and said light ole?nic hydrocarbon
in gaseous phase and in a reaction zone under
alkylating conditions including a temperature
varying between about 590° F. and about 850° F.
and a pressure of at least 500 pounds per souare
inch. with an alkylation" catalyst consisting es
sentiallv of an organic nitro compound which
forms with said light parai?nic hydrocarbon and
said light ole?nic hydrocarbon. a single, homo
geneous gaseous phase under said alkylation con
ditions. and controlling the concentration of the
light ole?nic reactant so thatalkylation is the
principal reaction.
10. The process of claim 9 wherein the alkyla
tion catalyst consists essentially of a nitro de
rivative of a light paraf?nic hydrocarbon.
17. The
process
of _ manufacturing triptane
which comprises contacting isobutane and pro
pylene in gaseous phase and in a reaction zone
under alkylating conditions including a tempera
turevvarying between about 775° F. and about
825° F. and a pressure of at least 2500 pounds per
square inch, with an alkylation catalyst con
sisting essentially of an organic nitro compound
which forms with said isobutane and said pro
’ pylene, a single, homogeneous gaseous phase un
der said alkylation conditions, in amounts vary
ing between about 0.5% and about 8% of the
charge, and controlling the concentration of the
propylene so that alkylation is the principal re—
action.
_
18. In a process of alkylating a paraf?nic hy
drocarbon with an ole?nic hydrocarbon in a re
.
action zone under alkylating conditions and in
11. In a process of alkylating isobutane with
the presence of catalytic material; the improve
propylene in a reaction zone under ‘alkylating _ ment which comprises contacting said para?inic
conditions and in the presence of catalytic mate 7° hydrocarbon and said ole?nic hydrocarbon in
'11
2,406,?76
gaseous phase and in said reaction zone-under
alkylating conditions, with an alkylation catalyst
consisting essentially of an organic nitrocom
pound which forms with said paraf?nic hydro
carbon and Said ole?nic hydrocarbon, a single, H
homogeneous gaseous phase under said alkylat
ing ‘conditions, and controlling the concentration
of the ole?nic reactant so that alkylation is the
principal reaction.
‘12
19. The process of claim 18 wherein the al
kylation catalyst consists essentially of a nitro
derivative of a light para?inic hydrocarbon.
JAMES B. KIRKPATRICK.
JOHN J. SOMERS.
ALEXANDER N. SACI-IANEN.
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