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Patented @ec. 31, 1946
2,413,384
UNITED STATES PATENT OFFICE
2,413,384.
PRODUCTION OF BRANCHED CHAIN
PARAFFINIC HYDRO CARB ONS
Louis Schmerling, Riverside, Ill., assignor to Uni
versal Oil Products Company, Chicago, Ill., a
corporation of Delaware
No Drawing. Application January 27', 1944,,
Serial No. 519,910
11 Claims.
This invention relates to reaction of a par
af?nic hydrocarbon of relatively low molecular
weight with an alkyl halide containing at least
6 carbon atoms per molecule and in the presence
of a catalyst of the Friedel-Crafts type.
An object of this invention is the production
( Cl. 260—67 6)
to employ isobutane and isopentane in the present
process for converting alkyl halides containing 6
or more carbon atoms per molecule into para?inic
hydrocarbons.
'
The primary, secondary, and tertiary alkyl
halides utilizable in this process may be obtained
from any ‘source. Furthermore, they are not
necessarily employed under the same conditions
at least 6 carbon atoms per molecule with a
para?inic hydrocarbon containing at least 4 and 10 of operation in the presence of the alternative
isoparai?nic hydrocarbons and different catalysts
not more than 5 carbon atoms per molecule in
of
the Friedel-Crafts type.
the presence of a catalyst of the Friedel-Crafts
Alkyl halides which I prefer to use in my
type.
process contain 1 halogen atom per molecule
Another object of this invention is the produc
ticn of branched chain ,paraf?nic hydrocarbons 15 and said halogen atom has an atomic weight of
between about 35 and 80. Some of these alkyl
by reacting, in the presence of a Friedel-Crafts
halides are produced by reacting a mono-ole?nic
type catalyst, an isopara?inic hydrocarbon con~
hydrocarbon and a hydrogen halide, such as hy
taining not more than 5 carbon atoms per mole
drogen chloride or hydrogen bromide, preferably
cule and an alkyl halide containing at least 6
in the presence of a catalyst, such as a metal
carbon atoms per molecule.
20 halide of the Friedel-Crafts type, a mineral acid,
A further object of this invention is the pro
or another acid catalyst. Addition of a hydrogen
duction of a para?inic hydrocarbon containing at
halide to an ole?n results in the production of
least '6 carbon atoms per molecule by reacting
tertiary alkyl halides from tertiary ole?ns and of
a para?inic hydrocarbon containing at least 4;
of a branched chain paraf?nic hydrocarbon by
causing reaction of an alkyl halide containing
and not more than 5 carbon atoms per molecule
in the presence of acatalyst of the Friedel-Crafts
type with an alkyl halide containing at least 6
carbon atoms per molecule, the alkyl halide being
converted into branched chain para?inic hydro~
secondary alkyl halides from non-tertiary ole?ns
containing 6 or more carbon atoms per molecule.
Tertiary alkyl halides also result from inter»
action of a tertiary alcohol and a hydrogen
halide. Primary alkyl halides, also utilizable in
carbons containing at least 6 carbon atoms per 30 the present process, are obtained by other means
such as by the treatment of a primary alcohol
molecule.
Qne speci?c embodiment of the present in
vention relates to av process for producing
with a hydrogen halide such as hydrogen chloride
or hydrogen bromide in the presence of a suit
able catalyst. Primary alkyl bromides may be
branched chain paraf?nic hydrocarbons con
obtained
also by addition of hydrogen bromide
taining at least 6 carbon atoms per molecule, w LI
' to a l-alkene, also known as an alpha-ole?n.
and comprises reacting analkyl halide contain
This addition of hydrogen bromide is effected
ing at least 6 carbon atoms per molecule with an
preferably in the presence of peroxides or sun
isoparamnic hydrocarbon containing not more
light.
.
than 5 carbon atoms per molecule and in the
Alkyl halides, including straight chain alkyl
presence of a catalyst of the Friedel-Crafts type. 40
halides
utilizable in my process, may also be
A further embodiment of the present invention
relates to a process for converting a para?in con
tainingat least 4 and not more than 5 carbon
atoms per molecule into branched chain para?lnic
obtained by halogenating para?ins with chlorine
or bromine. Thus n-hexane may be treated with
chlorine to form n-hexyl chloride as indicated vby
Equation 1 as follows:
hydrocarbons containing at least 6 carbon atoms 45
per molecule and comprises reacting said para?in
(1)
in the presence of a catalyst of the Friedel-Crafts
The
resultant
straight
chain
hexyl
chloride
may
type with an alkyl halide containing at least 6
then be treated with isobutane in‘ the presence of
carbon atoms permolecule, the alkyl halide being
simultaneously converted into branched chain 50 a Friedel-Crafts type catalyst according to the
process of this invention to form branched chain
hydrocarbons containingat least 6 carbon atoms
per molecule.
hexanes and octanes represented in Equation 2
as: (br) ~C6H14 and (br) —C8H1s, respectively.
Para?inic hydrocarbons utilized in the present
process contain at ‘least 4 and notmore than. 5
carbon atoms per ‘molecule. ,I prefer, however, 55
2,413,384
3
may be isolated as such. The tertiary butyl
chloride may then be reacted with propylene to
form a branched chain heptyl chloride suitable
for charging to the process illustrated by Equa
Another method which may be employed in
manufacturing branched chain alkyl halides con
taining at least 6 carbon atoms per molecule
involves the condensation of a relatively low
boiling alkyl halide with an ole?n containing 2
or more carbon atoms per molecule. Thus, con
tion 3.
I believe my. process for producing branched
chain para?ins by the reaction of a low molecular
weight isoparaf?n with an alkyl halide contain
densation of tertiary butyl chloride and ethylene
yields chloroneohexane. Similarly, condensa
tion of a mono-ole?n and a relatively low boil
ing alkyl halide to produce a higher-boiling alkyl
halide is effected in the presence of a catalyst
of the Friedel-Crafts type, but the particular
catalyst so employed is not necessarily the same
1 i)
ing at least 6 carbon atoms per molecule in the
presence of a Friedel-Crafts type catalyst will
give a higher yield of branched chain paraf?nic
hydrocarbons than is obtained in the usual
alkylation process. I believe also that my proc
ess will yield more desirable branched chain
as that preferably utilized in the further reac
para?inic gasoline of high octane number.
tion of the higher-boiling alkyl halide with iso
The alkylation of an isoparaf?n with an ole?n
in the presence of a Friedel-Crafts type catalyst
butane or isopentane to form a product con
taining a substantial amount of a branched chain
and a hydrogen halide as hydrogen chloride or
paraf?nic hydrocarbon having the same number
hydrogen bromide seems to involve the forma
tion of an alkyl halide corresponding in carbon
The alkyl
halide then appears to react with the ole?n to
form a higher molecular weight alkyl halide
which may be reacted further with a relatively
low molecular weight isopara?in under the con
ditions herein described to form a branched
chain para?in of gasoline boiling range and an
alkyl halide containing the same number of car
bon atoms per molecule as present in the rela
of carbon atoms per molecule as were present in
20 structure to that of the isopara?‘in.
said higher-boiling alkyl halide.
The process of the present invention for re
acting an alkyl halide containing at least 6 car
bon atoms per molecule with a para?inic hy
drocarbon containing at least 4 and not more
than 5 carbon atoms per molecule is carried out
in the presence of a catalyst of the Friedel~
Crafts type. Effective catalysts of the Friedel
Crafts type include aluminum chloride, alumi
num bromide, zirconium chloride, zinc chloride,
ferric chloride, boron ?uoride, etc. The conditions of operation utilizable with these catalysts
tively low-boiling para?in. For example, the
alkylation of isobutane with propylene in the
presence of aluminum chloride and hydrogen
chloride may involve the following steps:
‘
may be diiferent depending upon catalytic activ
ities and other factors. These different cal-Ta
lytic materials may be utilized as such, or they
may be composited with one another, or some 35
ofjthem may be deposited upon solid carriers or
supporting materials to produce catalyst com
posites of desired activities. Catalyst carriers
or supports include both adsorptive and sub
stantially non-adsorptive materials, including 40
alumina, silica, activated charcoal, crushed por
celain, raw and acid-treated clays, diatomaceous
earth, pumice, ?re brick, etc. The carriers
should be substantially inert in the sense that
Equation 6 illustrates the reaction of isobutane
and propylene in the presence of aluminum chlo
ride and hydrogen chloride whereby tertiary butyl
chloride and propane are formed. The tertiary
butyl chloride undergoes condensation with
propylene, as illustrated by Equation 7, forming
between catalyst and carrier, substantially no
interaction occurs which is detrimental to the
activity or selectivity of the catalyst composite.
The present processfcr producing a branched
chain paraf?nic hydrocarbon containing at least
6 carbon atoms per molecule may be illustrated
by Equation 3 given below, which relates to a
reaction between a branched chain heptyl chlo
ride, (b1‘)-C7H15C1, and isobutane and results in
the production of a branched chain heptane
a heptyl chloride which may be designated as
2,2-dimethyl-4-chloropentane. The
resultant
chloroheptane then reacts with isobutane, as il
lustrated in Equation 8, to yield tertiary butyl
chloride and a branched chain heptane, which
(br)-C'zH1e, isobutylene. and hydrogen chloride.
is normally referred to as an “alkylate.”
omn n
A substantial proportion of the isobutylene
which is formedreacts with isobutane to yield 60
branched chain octanes and other paraf?nic hy
drocarbons. Such production of branched chain
octanes from isobutane and isobutylene is rep
resented by Equation 4.
65
The net result of the reactions represented by
the two preceding equations may be represented
by Equation 5 as follows:
(5)
Tertiary butyl chloride formed by the reaction
above indicated may then add to more propylene
in accordance with the reaction of Equation '7,
and the total reaction cycle is thus repeated. Ac
cording to this mechanism of alkylation, only a
70 very small amount of propane need be formed,
since the reaction illustrated by Equation 6 may
occur to only a very small extent in order to
Under some conditions, part of the isobutylene
initiate the chain of reactions.
formed as indicated above reacts with hydrogen
In the present process, advantage is taken of
75
chloride to form tertiary butyl chloride which
2,413,384
the reactions illustrated by Equations 7 and 8
to obtain good yields of products of high quality.
with a reddish brown color. A total of 4.5 parts
Thus, for example, tertiary butyl chloride is re
by weight of hydrogen chloride was also obtained.
acted with propylene in the presence of any one
of a number of metal chlorides of the Friedel-v
tane, 2,3-dimethylbutane, and higher boiling
The liquor product consisted chiefly of isopen
Crafts type to yield a chloroheptane. The re
sultant chloroheptane is then reacted with an
excess of isobutane in the presence of aluminum
paral?ns. The presence of the 2,3-dimethyl
lbutanewas proven by preparing the crystalline
chloride, zirconium chloride, ferric chloride, etc,
Fifteen parts by weight is the theoretical yield
dibromide by photobromination.
to.v obtain heptane as a major product of the 10 of hexane to be expected from the 21 parts by
process; Isobutane is converted into tertiary
butyl chloride which may be isolated as such
when relatively mild reaction. conditions are em
ployed. but under more severe operating condi
tions, a substantial proportion. of the tertiary
butyl chloride reacts to form iso-octane and
weight of 4-chloro-2,2-dimethylbutane charged
to the process. Since 25 parts by weight of
liquid product was obtained, it appears that
drocarbons.
isobutane was converted into liquid paraf?nic hy
Example II
other paraf?nic hydrocarbons.
. My process for reacting an alkyl halide con
In another run similar to that described in
in- the presence of a, catalyst of the Friedel-Crafts
type, is carried out generally at a temperature of
from about —40° to about +100° C. and prefer
ably at a temperature of. from about —10° to
about +100° C. The conditions of operation
aluminum chloride. The glass-lined autoclave
containing the aforementioned materials was
charged with nitrogen to 50' atmospherespres
Example I, a solution of 28 parts by weight of
taining at least 6 carbon atoms per molecule with
a para?inic‘ hydrocarbon containing at least. 4. 20 4~chloro-°,2-dimethylbutane and 50 parts by
weight of isopentane were reacted in the presence
and-not more than 5 carbonatoms per molecule,
of 4 parts by weight of substantially anhydrous
andv particularly with isobutane and isopentane
are so controlled as to form a branched chain
paraliinic hydrocarbon fraction as the principal
product of the process. It is desirable to have an
excess of isobutane or isopentane admixed-with
the. alkyl’ halide being reacted. in the presence of
the catalyst in order to obtain a. relatively high
yield‘ of, branched chain paraf?nic hydrocarbons
and. to‘ form lower boiling alkyl halides suitable
for condensation with ole?nic hydrocarbons to
produce the higher boiling alkyl halides as here
inabove set forth.
‘
'
sure and the autoclave was 'then rotated and
heated at 50° C. for four hours. After this time
of reaction, the autoclave was cooled and the re
action products were removed therefrom, The
reaction product consisted of 45 parts by weight
‘ or" liquid product, 20 parts by Weight of a con
densible gas fraction, 9 parts by weight of cata
lyst layer, and 4 parts by weight of hydrogen
chloride. The ‘condensible gas fraction was found
to contain about 35 mole per cent of butanes, 60
per cent of pentanes, and 5 per cent of heXa'neS.
At least‘ 95 per cent of the" butanes and pentanés
were isobutane and isop'entane.
Distillation of the liquid product showed
‘ that
it
contained
35
parts
by
weight
of
liquid
product
in- my process will depend upon several factors, 40 boiling higher than isopentane. This liquid prod
including the halogen present in the alkyl halide,
uct included 12 parts by weight of hexanes con
the type of alkyl halide utilized,‘ and the nature
taining 2,3-dimethylbutane and 11 parts by
of the para?inic hydrocarbon which is being re
weight of an octane fraction. which contained
acted with-the alkyl halide. Thus,- alkyl bromides
The preferred operating temperature employed
can generally be utilized at a lower'reaction tem
perature than the corresponding alkyl chlorides.
The various alkyl halides may also be employed
under different conditions of operation, par
ticularly because the tertiary alkyl halides are
more reactive than secondary alkyl halides,v and
the latter, in turn, are more reactive than
primary alkyl halides. Some para?inic hydro
carbons are more reactive than others. Thus,
isopentane appears to be more reactive than
isobutane, and the latter reacts more readily
than normal pentane or normal butane under the
from'about 15 to 45 per cent of chlorohexane.
Example III
21‘ parts by weight of 4-chloro-2,2~dimethyl
pentane (prepared by the condensation of ter
tiary butyl chloride with propylene) was added
to 75 parts by weight of isobutane and 10 parts
by weight of alumimun chloride at —10° C. In
this treatment, the 4~ch1oro-2,2-dimethylpen
tane was added dropwise during 45 minutes to
the well-stirred mixture of isobutane and alu
conditions of operation herein set forth.
pressure. rlfrhe catalyst was converted into a yel
The following examples are given to illustrate
the process, although the data presented are not
low semi-solid, but substantially no hydrogen
introduced with the intention of restricting un 60 chloride was evolved. At this point 30 parts by
duly the broad scope of the invention.
weight of isopentane was added gradually, and
Example I
pleted in 30 minutes, and the stirring of the re
A solution of 21 parts by weight of 4-chloro-2,
action mixture was then continued for one hour.
Zedimethylbutane and 77 parts by weight of 65 The upper layer of reaction product was then de
isobutane was contacted with 5 parts by weight
canted from the‘ catalyst, washed with Water,
of aluminum chloride for one hour at 20° C. in
dried, and'distlilled. All of the chloroheptane was
a glass-lined rotating autoclave. This treatment
consumed during the reaction. The recovered
was followed by continuing the reaction at 40° C.
liquid‘ product, which-was completely parai?nic,
for three hours. The resultant reaction product, 70 consisted of 24 parts by weight of paraf?ns con
after cooling to 20° 0., consisted of 25 parts by
taining 6 or more carbon atoms per molecule.
weight of liquid, 59 parts by weight of con~
The liquid product comprised heptanes as the
densible gas comprising essentially isobutane,
and 9 parts by weight of a sludge-likematerial
largest fraction, but hexanes, octanes, nonanes,
and decanes were present in somewhat smaller
amounts.
.
,
2,418,884
isopara?inlc hydrocarbon containing not more
Example IV
When 44 parts by weight of propylene was
added during 30 minutes to a stirred solution of
92 parts by weight of tertiary-butyl chloride in
120 parts by weight of isopentane at -25° C. in
the presence of 20 parts by weight of aluminum
than 5 carbon atoms per molecule in the presence
of a catalytic amount ofsubstantially anhydrous
aluminum chloride, said catalytic amount being
less than the stoichiometric amount required to
form a double compound with said alkyl halide
but su?icient to effect replacement of the halogen
content of said alkyl halide with hydrogen, and
recovering
paraf?nic reaction products com
tane was formed together with small amounts of
higher boiling materials but hydrogen chloride 10 prising a branched chain paraffin hydrocarbon
containing the same number of carbon atoms per
chloride, the expected 4-ch1oro-2,2-dimethylpen
was not evolved and the aluminum chloride was
converted into an orange colored, semi-solid ma
molecule as said alkyl halide.
terial. The presence of 4-ch1oro-2,2-dimethyl
pentane in this reaction product was shown by
analysis of a small portion of the total reaction
product.
The temperature of the reaction mixture con
taining 4-chloro-2,Z-dimethylpentane was then
3. A process for preparing branched para?inic
hydrocarbons containing at least 6 carbon atoms
per molecule which comprises reducing an alkyl
halide containing at least 6 carbon atoms per
molecule by reacting said alkyl halide'at a tem
perature of from about -—40° to about 100° C.
with an isopara?inic hydrocarbon containing not
permitted to increase slowly. Evolution of hy
drogen chloride began when the temperature 20 more than 5 carbon atoms per molecule in the
presence of a catalytic amount of a metal halide
reached about -—13° C. and became copious at a
of the Friedel-Crafts type, said catalytic amount
temperature of from —10 to —4° C., the latter
being less than the stoichiometric amount re
temperature being reached after one hour, The
quired to form a double compound with said alkyl
stirring of the reaction mixture was continued
for 1.5 hours at -—4 to +2“ 0., when the evolu 25 halide but su?icient to effect replacement of the
halogen content of said alkyl halide with hydro
tion of hydrogen chloride had ceased. The re
action products included 28 parts by weight of hy
drogen chloride, 136 parts by weight of liquid
paraf?ns of higher molecular weight than pen
tane, and 57 parts by weight of a brown, viscous
catalyst layer. The liquid consisted essentially
of para?inic hydrocarbons, but traces of chlo
gen, and recovering para?inic reaction products
comprising a branched chain parai?n hydrocar
bon containing the same number of carbon atoms
per molecule as said alkyl halide.
4. A process for preparing branched para?inic
hydrocarbons containing at least 6 carbon atoms
per molecule which comprises reducing an alkyl
halide containing at least 6 carbon atoms per
molecule by reacting said alkyl halide at a tem
rine-containing compounds were present as evi
denced by the evolution of a small amount of hy
drogen chloride during the early part of the dis
perature of from about -—10° to about 100° C. with
tillation of the washed product. Hexanes, hep
an isopara?inic hydrocarbon containing not more
tanes, and ootanes were the main products of the
than 5 carbon atoms per molecule in the presence
reaction, but substantial amounts of nonanes,
of a catalytic amount of substantially anhydrous
decanes, and higher boiling hydrocarbons were
obtained also. Similar results were obtained 40 aluminum chloride, said catalytic amount being
less than the stoichiometric amount required to
in another run, which was carried out by placing
form a double compound with said alkyl halide
a similar mixture of propylene, tertiary butyl
but sufficient to e?ect replacement of the halogen
chloride, isopentane, and aluminum chloride in
content of said alkyl halide with hydrogen, and
an autoclave which was then rotated at 20° C. for
four hours and then permitted to stand over
recovering para?inic reaction products compris
night before removing the products therefrom
and separating them from the catalyst.
ing a branched chain paraf?n hydrocarbon con
taining the same number of carbon atoms per
The character of the invention and the type
of results obtained by its use are evident from
molecule as said alkyl halide.
5. A process for preparing branched para?inic
hydrocarbons containing at least 6 carbon atoms
though they are not to be construed as imposing 50 per molecule which comprises reducing é-chloro
the preceding speci?cation and examples, al
2,2-dimethylbutane by reacting said compound
undue limitations upon its broad scope.
I claim as my invention:
with isobutane at a temperature of from about
-l0° to about 100° C. in the presence of a cata
1. A process for preparing branched para?inic
hydrocarbons containing at least 6 carbon atoms
lytic amount of aluminum chloride, said catalytic
amount being less than the stoichiometric amount
per molecule which comprises reducing an alkyl
halide containing at least 6 carbon atoms per
molecule by reacting said alkyl halide with an
required to form a double compound with said
isoparaifmic hydrocarbon containing not more
than 5 carbon atoms per molecule in the presence 60
of a catalytic amount of a metal halide of the
4-chloro-2,Z-dimethylbutane but su?icient to ef
fect replacement of the chlorine content of said
4-chloro-2,2-dimethylbutane with hydrogen, and
li’riedel-Crafts type, said catalytic amount being
less than the stoichiometric amount required to
form a double compound with said alkyl halide
but su?icient to effect replacement of the halo
gen content of said alkyl halide with hydrogen,
recovering para?inic reaction products compris
ing a branched chain para?in hydrocarbon con
taining the same number of carbon atoms per
65
and recovering para?inic reaction products com
prising a branched chain para?in hydrocarbon
molecule as said 4-chloro—2,2-dimethylbutane.
G. A process for preparing branched parat?nic
hydrocarbons containing at least 6 carbon atoms
per molecule which comprises reducing ‘ii-chloro
2,2-dimethylbutane by reacting said compound
with isopentane at a temperature of from about
containing the same number of carbon atoms per
-10° to about 100° C. in the presence of a cata
70 lytic amount of aluminum chloride, said catalytic
molecule as said alkyl halide.
2. A process for preparing branched paraf?nic
hydrocarbons containing at least 6 carbon atoms
amount being less than the stoichiometric amount
required to form a double compound with said
per molecule which comprises reducing an alkyl
halide containing at least 6 carbon atoms per
4-chloro-2,2-dimethylbutane but sui?cient to ef
molecule by reacting said alkyl halide with‘ an 76
fect replacement or the chlorine content of said
2,413,384
9
4-chloro-2,2-dimethylbutane with hydrogen, and
recovering para?inic reaction products compris
10
haloalkane by warming ‘said reaction product in
ing a branched chain paraffin hydrocarbon con
taining the same number of carbon atoms per
the presence of said aluminum chloride catalyst
and an isoparaffinic hydrocarbon containing at
molecule as said 4-chloro-2,Z-dimethylbutane.
'7. A process for preparing branched paraf?nic
hydrocarbons containing at least 6 carbon atoms
per molecule, which comprises condensing an
least 4 and not more than 5 carbon atoms per
molecule to a temperature of from about —l0° to
alkyl halide and an ole?n in the presence of a
about 100° C., said aluminum chloride catalyst be
ing present in an amount less than the stoichio
metric amount required to form a double com
catalyst of the Friedel-Crafts type to form a 10 pound with said mono-haloalkane but sufficient
to e?ect replacement of the halogen content of
mono-haloalkane containing at least 6 carbon
said monohaloalkane with hydrogen, and recov
atoms per molecule, reducing said mono-haloal
ering paraf?nic reaction products comprising a
kane by reaction with an isopara?inic hydrocar
branched chain para?in hydrocarbon containing
bon containing not more than 5 carbon atoms
per molecule at a temperature of from about —10° 15' the same number of carbon atoms per molecule
as said mono-haloalkane.
to about 100° C. in the presence of a catalytic
amount of a metal halide of the Friedel-Crafts
type, said catalytic amount being less than the
stoichiometric amount required to form a double
compound with said mono-haloalkane but sul?
cient to e?ect replacement of the halogen con
tent of said mono-haloalkane with hydrogen, and
recovering paraf?nic reaction products compris
ing a branched chain paraffin hydrocarbon con
taining the same number of carbon atoms per molecule as said mono-haloalkane.
8. A process for preparing branched paraf?nic
hydrocarbons containing at least ‘6 carbon atoms
per molecule which comprises condensing an alkyl
halide and an ole?n at a temperature of from
about —40° to about 0° C. in the presence of a
catalyst of the Friedel-Crafts type to form a
mono-haloalkane containing at least 6 carbon
atoms per molecule, reducing said mono-haloal
kane by reaction with an isopara?‘imc hydrocar
bon containing not more than 5 carbon atoms per
molecule at a temperature of from about —10° to
about 100° C. in the presence of a catalytic
amount of a metal halide of the Friedel-Crafts
type, said catalytic amount being less than the
stoichiometric amount required to form a double
compound with said mono-haloalkane but being
su?icient to effect replacement of the halogen
content of said mono-haloalkane with hydrogen,
separating
from
the
resultant
products
10. A process for preparing branched para?inic
hydrocarbons containing at least 6 carbon atoms
per molecule which comprises condensing ter
tiary butyl chloride and propylene at a tempera
ture of from about ~—40° to about —10° C. in the
presence of an aluminum chloride catalyst for a
time su?lcient to produce 4-chloro-2,2-dimethyl
pentane as the principal reaction product, reduc
ing said 4-chloro-2,2-dimethylpentane by warm
ing said reaction product in the presence of said
aluminum chloride catalyst and isopentane to a
temperature of from about —10° to about 100° C.,
said aluminum chloride catalyst being present in
an amount less than the stoichiometric amount
required to form a double compound with said 4
chloro~2,2-dimethylpentane but su?icient to ef
fect replacement of the halogen content of said
4-chloro-2,2-dimethylpentane with hydrogen,
and recovering parai?nic reaction products com
prising a branched chain para?in hydrocarbon
containing the same number of carbon atoms per
molecule as said 4-chloro-2,2-dimethylpentane.
11. A process for preparing branched para?inic
hydrocarbons containing at least 6 carbon atoms
per molecule which comprises condensing tertiary
butyl chloride and propylene at a temperature
of from about —40° to about —10° C. in the pres
ence of an aluminum chloride catalyst for a time
a 45 suf?cient to produce 4-chloro-2,2-dimethylpen
branched chain paraffin having the same number
of carbon atoms per molecule as said mono
haloalkane and an alkyl halide having the same
number of carbon atoms per molecule as said iso
tane as the principal reaction product, reducing
said 4-chloro-2,2-dimethylpentane by warming
said reaction product in the presence of said
aluminum chloride catalyst and isobutane to a
paraf?nic hydrocarbon, recovering said branched 50 temperature of from about —10° to about 100° 0.,
said aluminum chloride catalyst being present in
chain paral?n, and recycling said last-named
an amount less than the stoichiometric amount
alkyl halide to condensation with said ole?n.
9. A process for preparing branched para?inic
' hydrocarbons containing at least 6 carbon atoms
required to form a double compound with said 4
ohloro-2,2-dimethylpentane but sufficient to ef
per molecule which comprises condensing a ter 55 fect replacement of the halogen content ofv said
4-chloro-2,2-dimethylpentane with hydrogen,
tiary alkyl halide and an ole?n at a temperature
and recovering para?inic reaction products com
of from about —40° to about —10° C. in the pres
prising a branched chain paraf?n hydrocarbon
ence of an aluminum chloride catalyst for a time
containing the same number of carbon atoms per
su?icient to produce a mono-haloalkane contain
ing at least 6 carbon atoms per molecule as the 60 molecule as said 4-chloro-2,2-dimethylpentane.
principal reaction product, reducing said mono
LOUIS SCI-HEERLING.
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