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Патент USA US2407033

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Patented Sept. 3, 1946
2,407,033
UNITED STATES PATENT OFFICE
Arlie A. O’Kelly, Woodbury, and Julius Plucker,
III, Pitman, N. J ., and Robert'H. Work, Phila
delphia, Pa., assignors to Socony-Vacuum Oil
Company, Incorporated, a corporation of New
York
No Drawing.‘ Application‘ December 10, 1943,
Serial No. 513,720
16 Claims.
(Cl. 260—683.4)
1
2
This invention‘ relates to the alkylation‘ of
para?inic hydrocarbons with ole?nic hydrocar
bons, and is more particularly concerned with the
production of high-octane motor fuel by the
atures and pressures, on the order of over 900° F.
and over 4000 pounds per square inch gauge, re-.
spectively; or may be conducted in the presence
catalytic alkylation of para?inic hydrocarbons
of alkylation catalysts at lower temperatures and
pressures, thereby assuring a high yield of de
with ole?nic hydrocarbons.
sired ‘alkylate by avoiding extensive degradation ’
,
_
of the reactants, the occurrence of side and sec
It is well known in the art to polymerize ole
ondary reactions, and appreciable polymeriza
finic hydrocarbon gases to produce motor fuels
tion of the ole?nic reactant. The two methods
having constituents of an unsaturated character.
Various commercial processes have been proposed 10 are known as thermal alkylation and as catalytic
alkylation, respectively.
for ultimately effecting the desired polymeriza
Several'methods are known for the catalytic
tion of the ole?nic hydrocarbons. These pro
alkylation of isoparailinic hydrocarbons with ole
cesses have been predicated upon the dictates of
?nic hydrocarbons. For instance, it is known to
the chemical nature of the stocks available as
well as engineering considerations such as initial 15 alkylate isoparaf?nic hydrocarbons with ole?nic
and operation costs; their essential feature being
that in the course of treating’the materials, the
olefinic hydrocarbons produced in the’earlier
stages of the process, are eventually polymerized
to gasoline. Accordingly, hydrocarbon gases may 20
be passed along with cracking stock or naphtha
through a cracking still to crack and polymerize
such gases to gasoline simultaneously with the
hydrocarbons in the presence of sulfuric acid,
phosphoric acid, metal phosphates, metal halides,
activated clays and the like, as catalysts. In
these catalytic alkylation processes, the hydro
carbon ‘reactants' form with the alkylation cat
alysts, a heterogeneous vsystem during the alkyla
tion operation. Since under alkylation condi
tions, the catalytic activity of the alkylation cat
alysts appears to be predicated upon contact
cracking or reforming, or parai‘?nic hydrocarbon
gases may be separately cracked to ole?nic hy 25 between the catalysts and the gaseous hydro
carbon reactants at the interfaces therebetween,
drocarbon gases and these gases are subsequently
in these processes, the catalysts are used in
passed with naphtha through a polymerizing and
amounts varying between 10% and 200% by
reforming still. In some instances, the, processes
weight, on the charge, depending on the catalyst
involve the use of catalysts for facilitating the
used. Due to these comparatively high amounts,
cracking and/or polymerization operations.
where possible, recovery and regeneration of the
It is also well known in the art. to combine
catalysts have been proposed. This, of course,
para?inic hydrocarbons directly with ole?nic‘hy
involves highinitial and operation costs. Fur
drocarbons by processes broadly called alkylation
ther, it' is also known that certain substances
processes, to produce motor fuels having con
stituents of saturated character. ‘In alkylation .35 called promoters, promote the catalytic action of
these alkylation catalysts. Accordingly, several
processes, a charge comprising a mixture ‘of a
processes have been proposed ‘wherein small
parai?nic hydrocarbon, called the paraffinic re
amounts of these promoters, on the order of about
actant, and an olefinic hydrocarbon, called the
1% to 3% by weight on the charge, are added
ole?nic reactant, is subjected to high tempera
tures and pressures to produce a saturated alkyl 40 to the catalysts to promote ‘their alkylation cat
alytic activity.
,
_
ate product. Since conditions of alkylation also
A copending application, Serial Number 502.
cause polymerization of the ole?nic reactant, it
018, ?led September 11, 1943, in which one of
is necessary to maintain a relatively low concen
the inventors of the present application is co
tration of the ole?nic reactant in the charge.
The only limit to the pressure used appears to 45 inventor, is directed to the process of alkylating
paraflinic and isoparaf?nic hydrocarbons with
be the feasibility of maintaining high pressures.
ole?nic hydrocarbons, which comprises contact
On the other hand, the temperature used is
ing a parai?nic or isopara?inic hydrocarbon and
limited by degradation of the hydrocarbon re
an ole?nic hydrocarbon in a reaction zone under
actants in the charge to low molecular weight
hydro-carbons, and the occurrence of side reac 50 alkylating conditions, with small or promoter
amounts of what has been termed therein, a
tions, including polymerization of the ole?nic re
homogeneous gaseous phase alkylation catalyst
actant, under high temperature conditions, that‘
consisting essentially of material that forms with
substantially reduce the purity of the product
obtained.
.
‘
Alkylation may be conducted at high temper
the hydrocarbon reactants, a single, homogeneous
gaseous phase under the alkylation conditions of
2,407,033
3
4
.
pylene in the presence of heterogeneous alkyla
the reaction zone. The alkylation conditions of
the process of this copending application, com
tion catalysts have octane numbers of 39 and 82,
respectively, the importance of the alkylation of
prise a broad temperature range of about 590° F.
to about 850° F., preferably, about 650° F. to
isobutane with propylene in the presence of ho
about 825°‘F., and pressures of at zleast‘500wpounds 5 :mogeneous gaseous phase catalysts; under alkyla
per square .inchgauge, preferably, at. least‘ 1500
tion, conditions that favor the production of
pounds per square inch gauge.
triptane is manifest.
It was also found that in
actual practice, it was impossible to obtain trip
Another copending application, Serial Number
..tane exclusively, appreciable amounts of 2,2-di
502,813, ?led September 17, 1943,, in which one
of the inventors of the present applicationylikea ‘ll‘lrmethylpentane and Z-methylhexane being always
formed.
wise is coinventor, is directed. to, the‘process of
.The; specificv classes of homogeneous gaseous
alkylating isobutane with propylene; which-com
'phase alkylation catalysts claimed in the above
prises contacting isobutane-and‘propylene in a
reaction zone under closely controlled alkylating
noted copending applications, are organic halides,
conditions, with promoter or small amounts of 15 and, more particularly, organic chlorides and or
the homogeneous gaseous phase catalystsbroadly
ganic bromides.
disclosed in the copending application referred to
"We have found that organic cyclic oxygen com
pounds wherein oxygen is part of the ring, are
hereinbefore, the closely controlled alkylating
suitable homogeneous gaseous phase alkylation
conditions including a, temperature ‘range of
about 750° F. to about:850° F., preferably, about 20 catalysts, and that isoparaf?nic and para?inic
.775? Rite about 825° F., and-pressures of at/least
2500 pounds per squareinch gauge.
" hydrocarbons (may be efficiently alkylated with
.In: the. alkylation of isobutane with: vpropylene
highaoctane,gasoline, in the presence of small
:or promoter-amounts of vorganic cyclix oxygen
vcompounds wherein oxygen is part of the ring,
that form with the hydrocarbon reactants, a
in: the presence ofhomogeneousgaseous: phase
catalysts, it was found that the alkylate obtained
included constituents thatare entirelyidiilerent
fronrthe constituents of the .hydrocarbonsal
"kylate’ obtained in the alkylation of isobutane
with: propylene in the-presence: of. knownheter
.ole?nic-hydrocarbons to produce high yields of
single'homogeneous gaseous phase during the al
- kylation-operation.
'We have also {found that organic‘ cyclic oxygen
l ogeneous alkylation’cat'alysts, i.:e.,:'AlClz, H2SO4,(=so ‘ compounds wherein oxygen is' part of the ring,
. are suitablehomogeneous gaseous phase alkyla
and the like. Thus, when .heterogeneousalkyla
I ticn catalysts are used,‘ 2,3-dimethylpentane and
tion loatalystsfin the catalytic alkylation of iso
‘ 2,4-dimethylpentane are important constituents
of the hydrocarbon’ alkylate‘obtained.
butanewith'propylene under the controlled con
On the
. ditions'of. alkylation described in the copending
- other hand; triptane or 2,2,3‘-trimethylbutane,e35 ' application Serial Number 502,813, ?ledSeptem
'2,2¢dimethylpentane, and ~2-methylhexane .' are
-, ber, 17, 1943.
the‘ predominant ‘constituents of the hydrocar
‘hon alkylate where‘ gaseous phase homogeneous
It isv an object of thepresent invention to pro
-~vide an’ e?icient process-for catalytically alkylat
. alkylation catalysts a-re‘employed. ‘In thisrco
ting isopara?inic or-para?inic hydrocarbons with
< pending application, the formation of these threemio Ole?nic hydrocarbons Another object is to pro
compounds was postulated as follows:
~vide=an e?icient process for catalytically alkylat
.- ing either normalparaflim'c hydrocarbons or iso
, paraffinicvhydrocarbons with. ole?nic hydrocar
bons to produce’ high yieldsof high-octanerno
~45 tor fuel. ..A morespeci?c object is 'to provide a
-, process vfor catalytically alkylating .isobutane
~ withpropylenerto(produce high yields of high
. octanemotor fuel.
A very importantobject is
.--to afforda process capable of carrying out the
.1550 above . objects by using small or promoter
.. amounts. of..organic~cyclic .oxygen. compounds
wherein ‘oxygensis?part .of. the ring, that form
,withL-the hydrocarbon reactants, a single homo
_geneous gaseous phaseduring the alkylation op~
a; “aeration. Other..objeots and. advantages of the
11
present inventionwillrbecome apparent to those
III
skilled ‘in theart from the followingvdescription.
‘Broadly stated, our invention provides a process
fonalkylating.para?inic or isoparaf?nic hydro
From a motor fuel standpoint, the 2,2-dimethyl-_
pentane produced by the ?rst reaction’ has ana.im,carbons,- particularly isobutane, with ole?nichy
octane number of about 80 CFR motor method;
the triptane produced by the second reaction has
' '. drocarbons,= particularly propylene, .which com
prises-contacting the paraflinic. and ole?nic. hy
._drocarbons in’ gaseous phaseandin av reaction
an octane number of well over 100, and the 2
.zoneuunder .alkylating conditions, with small or
methylhexane obtained in the third reaction, has
an octane number of’ about 45. In view of the‘ ‘1,7,.’ promoter amounts of an alkylationcatalyst com
prising organic cyclic-oxygen compounds wherein
foregoing, in the manufacture of high-octane
» oxygen isgpart of the ring, ‘that. form with the
motor fuel by the alkylation of isobutane with’
. hydrocarbon-reactants, a single homogeneous
propylene, alkylation conditions that favor the
jgaseous vphase under the alkylation conditions
production of triptane obviously are ‘preferable.
Further, since neohexane which may be produced 70- of ‘the reaction zone.
Animportant feature of ‘the process of the
by the alkylation of isobutane with ethylene, has
present-invention is the fact that, contrary to
.an octane’number of'93.4, and since 2.3-dimeth
, ylpentane and.2,¢l-dimethylpentane which are the
v‘the'known catalytic alkylation processes: of the
predominant constituents of the 'alkylate ob
prior art which are only capable of .alkylating
tained' in the alkylation of isobutane with Dro- 75" isopara?inic hydrocarbons, our process is capable
231013033
5
of alkylating either normal para?inic or isoparaf
?nic hydrocarbons with substantially equal ease.
Another important feature of the process of
the present invention is the relatively low tem
6
of‘ the present invention are organic cyclic oxy
gen compounds, and more particularly, hetero
cyclic oxygen compounds. We especially prefer
to use as our homogeneous gaseous phase alkyla
perature that may be used. As a result, degrada UT tion catalysts, alkene oxides. Thus, at the pres
tion of the hydrocarbon reactants in the charge
ent time we consider ethylene oxide and propylene
to low molecular weight hydrocarbons, and the
oxide, typical examples of the homogeneous gase
pronounced occurrence of side reactions includ
ous phase alkylation catalysts of our invention.
ing polymerization of the ole?nic hydrocarbons,
The amounts of organic cyclic oxygen com
are substantially completely avoided. Conse 10 pounds used in our process, vary between about
quently, in our process, we obtain high yields of
0.5% and about 3%, and preferably, between
a high grade product that is almost entirely
about 1% and about 1.25%, with respect to the
paraf?nic in nature and is substantially free from
total charge of hydrocarbon reactants. It must
'
be noted, however, that larger amounts maybe
A very important feature of the present inven 15 employed if desired, ‘although no additional ad
tion is the fact that, contrary to known catalytic
vantages result therefrom.
processes of the prior art, in which the hydro
The para?inic and ole?nic hydrocarbons to be
carbon reactants being processed, form with the
used in our process may be derived from any
alkylation catalysts, a heterogeneous system dur
suitable source, as is well known in the art, and
ing the alkylation operation, the alkylation proc 20 may be used either in the pure state or in ad
ess of our invention employs alkylation catalysts
mixture with other constituents not undesirable.
consisting essentially of materials that form with
The paraf?nic and ole?nic hydrocarbons usually
the hydrocarbon reactants being processed, a
employed in the preferred operation of manu
single homogeneous‘ gaseous phase. The alkyla
facturing motor fuels, will be the normally gas
tion catalysts of the present invention may be 25 eous para?inic hydrocarbons, except methane
called, therefore, homogeneous gaseous phase al
and ethane, and the normally gaseous ole?nic
kylation catalysts in contradistinction to the al
hydrocarbons, as is well understood in the art.
impurities.
kylation catalysts of the prior art which may be
Here again our process has a distinct advantage
referred to as heterogeneous catalysts. Accord
over many of the prior art processes in that the
ingly, as a result of the catalyst’s being in the 30 ole?n ethylene, may be used for alkylating the
same phase or state as the hydrocarbon reactants
para?inic hydrocarbons. It is well known that
being processed, fouling of the catalyst is sub
ethylene cannot be used in many catalytic proc
stantially eliminated and agitation and/or mix
esses, including the sulfuric acid process, whereby
the supply of available ole?nic hydrocarbons is
ing problems are non-extant. Further, since the
catalytic activity of alkylation catalysts appears
restricted. Therefore, an important aspect of
to be predicated somewhat upon contact between
the catalysts and the gaseous hydrocarbon re
the present invention is the fact that butane, for
instance, may be alkylated with ethylene.
actants, at the interfaces therebetween, it follows
that the catalytic efficiency of a given catalyst
A conventional and preferred source of paraf
‘ ?nic and ole?nic hydrocarbons is the ?xed gases
increases with the increase in area of interfacial 40 obtained around petroleum re?neries. These
?xed gases may furnish substantially all the de
contact, other variables remaining ‘constant.
Hence, since the homogeneous catalysts of our
sired paraf?nic and ole?nic hydrocarbons, or it
process inherently furnish the greatest possible " may be necessary or desirable to‘ obtain addi
“interfacial contact” between the catalyst and
tional supplies, as is Well understood. Additional
ole?nic hydrocarbons, if required, may be formed
the hydrocarbon reactants under the conditions
from a portion of the para?lnic hydrocarbons.
concomitant
of
achieved
alkylation,
using
high
e?icient
relatively
yield of
catalytic
small
highamounts
grade
activity
alkylate,
of with
homois‘
a ‘ “ 0n" the other hand, additional paraflinic hydro~
carbons may be admixed to increase the concen
geneous gaseous phase alkylation catalyst.
tration of para?inic hydrocarbons to a desired
In view of the foregoing, an operationfeature of ; magnitude.
In carrying out our process, we use tempera
the process of the present invention that is of
considerable practical importance, is that small ‘ ' tures varying between about 590° F. and about
or promoter amounts of organic cyclic ‘oxygen " 850° F., and preferably temperatures varying be
tween about 650° F. and about 825° F. In the
compounds wherein oxygen is part of the ring,
are used as alkylation catalysts. These amounts ,j > alkylation of isobutane with propylene, however,
Ywe have found, as disclosed in the copending ap
‘are so small that they may be discarded feasibly,
plication Serial Number 502,813, filed September
thereby obviating recovery and regeneration
17, 1943, that the best yields of desired'alkylate
problems and eliminating high initial and op
are obtained when the alkylation is conducted
eration costs.
.' at temperatures falling within about 750° F. to
A most important feature of the present inven
about 850° F., and preferably, about 775° F. to
tion is that high yields of high-octane motor fuel ‘
about 825° F. The alkylate produced under these
are obtained by alkylating isobutane with propyl
conditions contains no more than 5% of ole?nic
ene in the presence of organic cyclic oxygen com
hydrocarbons and no aromatics so that the pre
pounds wherein oxygen is part of the ring.
As disclosed in application Serial Number 502, 15 dominance of alkylation obtained thereby is a
018, ?led September 11, 1943, the homogeneous
‘gaseous phase alkylation catalysts of the present
invention may be solids, liquids or gases under
normal conditions. However, it is likewise essen
tial for the purposes of our process, that the or
ganic cyclic oxygen compounds wherein oxygen is
part of the ring form with the hydrocarbon re
actants being processed, a single homogeneous
gaseous phase under the alkylation conditions of
the process. Generally speaking, the catalysts
distinct feature of the process.
Under appre
ciably higher temperature conditions, side reac
tions occur that substantially reduce the purity
In the alkylation of
isobutane with propylene in accordance with the
process of the present invention, it must be noted
‘ of the product obtained.
that , even within the
preferred temperature
range, side reactions occur that account for sub
stantial portions of the total alkylate, but a frac
tion boiling at 79° C. to 82° C. and consisting of
2.;4015033
‘7
~ aboutii?spartsz- or triptane to: 85 parts; of» 2;,2-tdi
comprises. contacting isobutane with-propylene; in
,.rnethylpentane;.-may beobtained.
gaseous phaseand ina-reaction zoneunder, alkyl
>
> .
,ating: conditions including temperatures varying
';-_',l3he-.-pressure to‘. be, used::in:.Qur-;pro,cess ;rna
vary‘ ,iromnboutr Edd-poundsper square. inch to
between about 775° F. and about 825° Rand pres
v.about-6090 pounds per-'squarenireh-or more, and 5 suresupwardaof 2500 lbs-per square inch,.in the
presence of ethylene oxide, and maintaining: said
preferably from-v about1-25o0 :pounds_;~per square
inch to about 6000 pounds per square inch? for
thealkylation. oi isobutane-with-propylene, the
» most ; suitable. pressure:~being: more or: lessjde
:pendent :upon :the,_~particu1ari temperature; in-.
isobutane in excess over; said propylene ‘ill-‘Said
reactionzone' so that ,alkylationz: is the principal
. reaction.
2. The process ofalkylating a para?inic hydro
.carbon'withan ole?nic hydrocarbon, which com
10 .
volved. In general, the. his;‘ er, :the pressure, ‘the
:liigher the'yield of ‘ alkylate. ,Accordingly, the
criterion. {or establishing: an upper limit: to the
zprises contacting said parafiinic hydrocarbon and
:pressurarange used :is'primarily the feasibility
in a reaction Zone under alkylatingv conditions
of maintaining such: pressure.
said ole?nic, hydrocarbon,‘in-gaseous phase and
15 including temperatures varying -,_ between about
Y
,-paraf?n—ole?n alkylation processes, to‘ keep the
concentration of the ole?nic hydrocarbons rela
1590? F: and: about 8501B‘.- andpressuresupwards
ofs500. lbspper square; inch, with an alkylation
catalyst-comprising ethylene oxide, and main
‘ tively low during the alkylation reaction in order
. taining said para?lnic hydrocarbon in excess over
In our process it is, desirable; as in- known iso
.to eliminate as ‘much ole?n polymerization'as. 20 said ole?nic hydrocarbon in saic reaction zone
possible. Accordingly, itis advisable to main
sothat allrylation is the principal reaction.
tain the ole?n concentration in the charge below
3.-The process of alkylating a light para?inic
about 25%~by volume,‘ and preferably, between
aboutz'7% and aboutj12% by volume.
hydrocarbonwvith alight ole?nic hydrocarbon,
which comprises: contacting said. light para?inic
hydrocarbon with said'light o-lefinic hydrocarbon,
~The alkylate product" that we obtain, distills 25
»over.;a fairly largeboiling range, buta greater
in ,gaseous' phase: and ma reactioirzone under
part of the alkylate,<usually from about 85% to
alkylating 1 conditions including temperatures
about.»90%,,distills in the boiling range of- avia
varying between about 650? F, and about 825° F.
tion-,gasolines. qThe iodine number of the avia
and pressures upwards of 1500 lbs. per square
tionldistillate is l0w,~on the order of about 10 to
inch, in the presence of an organic‘ cyclic oxygen
25. As mentioned. hereinbefore, the alkylate
coinpoundwherein oxygen is'part of the ring,
product ' consists predominantly of branched
which forms with said light para?inic hydrocar
parai?nic hydrocarbons.
bon and said light ole?nichydrocarbon, a single
,To illustrate our invention,-we set forth below
homogeneous gaseous phase under said alkylating
in Table I, typical ‘data obtained in testing and
conditions,
maintaining said light para?lnic
in carrying out our process:
hydrocarbon in excess over said light ole?nic
. Table I
- Run No.
l
2
3
4
5
Charge
"Isobutane, wt. in grams __________________ __'_
Propylene, wt. in grams.
___ 26
" Catalyst ________________ _.
;__
Wt. per cent on charge,“
_.'.
Temperature, ° 1*‘_________
___
" Pressure in, lbs./sq. m ____________________ ._
_
Product
Wt. in grams _____________________________ __
799 O.—82° 0. fraction, wt. per cent of product
,Triptanc, Wt. per cent of traction _________ .. 5
It will be observed that when no catalyst is
..used as in run No. 1, the yield of alkylate product
is relatively very low, and signi?cantly, the yield
of the 79° C.—82° C; or triptane-containing frac
tion, and the triptane content of the fraction,
areproportionately, low. A comparison-of the
results obtained in run No. 3 and No. 4, using
di?erent- amounts-of propylene oxide, illustrates
the- fact that little, advantage if any, is gained
by using amounts of the homogeneous gaseous
phase alkylation catalysts of our invention, larger
than the upper limit of our preferred range.
Although the present invention has been de
scribed in. conjunction with'preferred embodi
.nients, it is to be understood that modi?cations
and variationsmay be resorted to without depart
ingfrom 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 ap
pended claims.
*W e claim:
hydrocarbon in said reaction zone so that alkyla
tion is the. principal reaction.
4. The process of manufacturing high-octane
motor. fuel, which comprises contacting a light
para?inic hydrocarbon and a light ole?nic hydro
carbon, in gaseous phase and in a. reaction zone
under alkylating conditions, including tempera
60 tures varying between about 650° 'F. and about
825° Rand pressures upwards of 1500 lbs. per
square inch, with an alkylation catalyst compris
ing ethylene oxide, and maintaining said light
paraflinic hydrocarbon in excess over said‘ light
olefinic hydrocarbon in said reaction zone so that
alkylation is the principal reaction.
5.‘ The process of manufacturing triptane,
which comprises contacting isobutane with pro
pylene', in gaseous phase and in a reaction zone
under. alkylating conditions, including. tempera
tures varying between aboutv 775° F. and . about
., 825°
and pressures upwardsof. 2500, lbs. per
squareinch, in thepresence of furfural andmain
1. The process of manufacturing triptane which 75 taining said isobutane in excess over said pro
2,407,033
pylene in said reaction zone so that alkylation
is the principal reaction.
10
and said ole?nic hydrocarbon, in gaseous phase
and in a reaction zone under alkylating condi
6. The process of manufacturing triptane by
alkylating isobutane with propylene, which com
prises contacting said isobutane with said pro
tions including temperatures varying between
pylene, in gaseous phase and in a reaction zone
alkylation catalyst comprising propylene oxide,
and maintaining said paraf?nic hydrocarbon in
under alkylating conditions including tempera
about 590° F. and about 850° F. and pressures
upwards of 500 lbs. per square inch, with an
tures varying between about 750° F. and about
excess over said ole?nic hydrocarbon in said re
850° F. and pressures upwards of 2500 lbs. per
action zone so that alkylation is the principal
square inch, in the presence of an organic cyclic 10 reaction.
oxygen compound wherein oxygen is part of the
12. The process of alkylating a para?inic hy
ring, which forms with said isobutane and said
drocarbon with an ole?nic hydrocarbon, which
propylene, a single homogeneous gaseous phase
comprises contacting said para?im'c hydrocarbon
under said alkylating conditions, and maintain
and said ole?nic hydrocarbon, in gaseous phase
ing said isobutane in excess over said propylene 15 and in a reaction zone under alkylating condi
in said reaction zone so that alkylation is the
tions including temperatures varying between
principal reaction.
about 590° F. and about 850° F. and pressures
7. The process of manufacturing triptane by
upwards of 500 lbs. per square inch, with an
alkylating isobutane with propylene, which com
alkylation catalyst comprising ‘furfural, and
prises contacting said isobutane and said pro 20 maintaining said p-araf?nic hydrocarbon in excess
pylene, in gaseous phase and in a reaction zone
over said ole?nic hydrocarbon in said reaction
under alkylation conditions including tempera
zone so that alkylation is the principal reaction.
tures varying between about 750° F. and about
‘13. The process of manufacturing high-octane
850° F. and pressures upwards of 2500 lbs. per
motor fuel, which comprises contacting a light
square inch, with an alkylation catalyst compris 25 para?inic hydrocarbon and a light ole?nic hydro
ing ethylene oxide, and maintaining said isobu
carbon, in gaseous phase and in a reaction zone
tane in excess over said propylene in said reaction
zone so that alkylation is the principal reaction.
under alkylating conditions including tempera
pylene, in gaseous phase and in a reaction zone
ing propylene oxide, and maintaining said light
tures varying between about 650° F. and about
8. The process of manufacturing triptane,
825° F. and pressures upwards of 1500 lbs. per
which comprises contacting isobutane with pro 30 square inch, with an alkylation catalyst compris
- under alkylating conditions including tempera
tures varying between about 775° F. and about
325° F. and pressures upwards of 2500 lbs. per
_ square inch, in the presence of an organic cyclic
oxygen compound wherein oxygen is part of the
ring, which forms with said isobutane and said
propylene, a single homogeneous gaseous phase
under said alkylating conditions, and maintain
para?inic hydrocarbon in excess over said light
ole?nic hydrocarbon in said reaction zone so that
alkylation is the principal reaction.
14. The process of manufacturing high-octane
motor fuel, which comprises contacting a light
para?inic hydrocarbon and a light ole?nic hy
drocarbon, in gaseous phase and in a reaction
zone under alkylating conditions including tem
ing said isobutane in excess over said propylene 40 peratures varying between about 650° F. and
in said reaction zone so that alkylation is the
about 825° F. and pressures upwards of 1500 lbs.
principal reaction.
per square inch, with an alkylation catalyst com~
9. The process of alkylating a para?inic hydro
prising furfural, and maintaining said light par
af?nic hydrocarbon in excess over said light ole
carbon with an ole?nic hydrocarbon, which com
prises contacting said para?inic hydrocarbon with
said ole?nic hydrocarbon, in gaseous phase and
in a reaction zone under alkylating conditions
including temperatures varying between about
?nic hydrocarbon in said reaction zone so that
alkylation is the principal reaction.
15. The process of manufacturing triptane by
alkylating isobutane with propylene, which com
prises contacting said isobutane and said pro
590° F. and about 850° F., and pressures upwards
of 500 pounds per square inch, in the presence 50 pylene, in gaseous phase and in a reaction zone
under alkylation conditions including tempera
of an organic cyclic oxygen compound wherein
tures varying between about 750° F. and about
oxygen is part of the ring, which forms with said
850° F. and pressures upwards of 2500 lbs. per
paraffinic hydrocarbon and said oleflnic hydro
square inch, with an alkylation catalyst compris
carbon, a single homogeneous gaseous phase
under said alkylating conditions, and maintain 55 ing propylene oxide, and maintaining said isobu
tane in excess over said propylene in said reaction
ing said para?inic hydrocarbon in excess over
zone so that alkylation is the principal reaction.
said ole?nic hydrocarbon in said reaction zone
16. The process of manufacturing triptane by
so that alkylation is the principal reaction.
alkylating isobutane with propylene, which com
10. The process of manufacturing triptane
which comprises contacting isobutane with pro 60 prises contacting said isobutane and said pro
pylene, in gaseous phase and in a reaction zone
pylene, in gaseous phase and in a reaction zone
under alkylating conditions including tempera
under alkylation conditions including tempera
tures varying between about 750° F. and about
850° 1",‘. and pressures upwards of 2500 lbs. per
square inch, in the presence of propylene oxide, 7 65 square inch, with an alkylation catalyst compris
ing furfural, and maintaining said isobutane in
and maintaining said isobutane in excess over
excess over said propylene in said reaction zone
said propylene in‘ said reaction zone so that
so that alkylation is the principal reaction.
alkylation is the principal reaction.
ARLIE A. O’KELLY.
11. The process of alkylating a para?inic hy
JULIUS PLUCKER, III.
drocarbon with an ole?nic hydrocarbon, which 70
ROBERT H. WORK.
comprises contacting said para?inic hydrocarbon
tures varying between about 775° F. and about
825° F. and pressures upwards of 2500 lbs. per
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