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Патент USA US2409700

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Patented 0a. 22, 1946
“
‘
'
2,409,699
UNITED STATES PATENT OFFICE
' 2,409,699
PREPARATION OF CYANOMETHYL DIALKYL
ORTHOFORM'ATES
Donald J. Loder and William F. Gresham, Wil
mington, Del., assignors to E. I. du Pont de
Nemours
& Company, Wilmington, Del., a cor
poration of Delaware ‘
No Drawing. Application September '7, 1944,
Serial No. 553,108
5 Claims. (Cl. 2‘60—464)
This invention relates to the preparation of
V
charged with 28.5 parts 2(0.5 M) of formaldehyde
orthoformates and more particularly cyanoalkyl
a pressure of approximately 105 mm. During the
dialkyl orthoformates by reacting alkyl orthofordistillation 31.6 parts of ethanol is recovered. The
mates with aldehyde cyanhydrins. Yet another 10 product is then fractionated under a reduced
are realized by‘su'bjecting an alkyl orthoiormate 15
.
.
.
the process at a temperature ranging between 75 20
This exairiple illustrates the advantages de~
d
Example II.—-The process of Example I is sub
rated and purl?ed by fractlonatlon25 I and the cyanomethyl diethyl orthoformate ob
he reaction is illustrated by the generic
tained in a yield of approximately 56.2%.
equation:
The process illustrated in the examples may be
HCXOR) 3+HORICN_>HC(OR) 2OR1CN+ROHV
used for the preparation of a number of related
in which R designates an alkyl and B1 an alkylene 30 produced by reacting the aldehyde cyanhydrins
presence of an eizcess of the alkyl orthoformate 4r) athyl, methylpropyl, methylethylpropyl, and simi
examples in which parts are by weight unless
.
_
otherwise indicated.
general equatwn'
Ervample I.—A round bottom glass ?ask is 55
HC(OR)zOR1CN+H2eHC(0R)onnmv-“?‘
2,409,699
wherein R is an alkyl group and R1 an alkylene
pressure, is obtained upon fractionation of the
group.
More speci?cally,
valuable amines
as aminoethyl
diethyl orthoformate
may besuch
obtained in accord
m . with the equation:
product.
Example IV.——The process of Example III is
duplicated. employing
40 parts
5 substalrsltially
(0.25
) of cyanomethyl
diethyl orthoformate,
HC(OC2H5)2OCH2CN+2H2'>
HC(OC2H5) zOCHzCHzNHz
85
parts
M) catalyst
of anhydrous
ammonia
and,
parts
of a (5
nickel
supported
on kieselguhr.
The hydrogenation of the aminoethyl orthoThis reaction is conducted at a temperature be
formates is preferably conducted under superattween 103 and 125° C. for approximately 4 hours
mospheric pressures between 50 and 1500 utmost‘ 10“ under a hydrogen pressure of about ‘700 at
Pheres and at temperatures ranging between 40
and. 150° C. Any s ‘table hydrogenation catalysts
may
be employed
such, for
example,
nickel
supported
on kieselguhr,
Raney
nickel as
catalysts,
mospheres. Approximately an 87.5% conversion ‘
of the nitrile to the amine is realized.
We
1, Aclaim;
process for the preparation of a. cyano
cobalt
dial‘
1 orthoformate
which tocomprises
like. catalysts, nickel chromite catalysts and the i5 methyl
subjecting
formaldehyde
cyanhydrin
a reac
The examples which follow illustrate pi‘éfél‘i‘éd
tion with an alkyl orthoformate in the presence of
methods of converting the cyanoalkyl orthoiora condensation catalyst,
mates to aminoalkyl orthoformates. In these
2. A process for the preparation of a cyano
examples parts are by weight unless otherwise 20 methyl diethyl orthoformate which comprises
indicated.
subjecting formaldehyde cyanhydrin to a reac
Exdmple III .-*—‘A silver-lined pressure-resisting
tion with ethyl orthoiormate in the presence of
autoclave is charged with 31.8 parts (0.2 M) of
a condensation catalyst.
cyanomethyl diethyl orthoformate, 85 parts (5 M)
3. A process for the preparation of a cyano
of anhydrous ammonia and 20 parts of a nickel 25 methyl dialkyl orthoformate which comprises
catalyst supported on kieselguhr. The reaction is
subjecting an aldehyde cyanhydrin to a reaction
conducted at a temperature between 108 and
112° C. under a hydrogen pressure of about ‘700
with a molar excess of an alkyl orthoformate at
a temperature between 30 and 150° C. and in the
atmospheres and for approximately 11/2 hours.
presence of zinc chloride as the catalyst.
Pressure is then released from the autoclave after 30 4. A cyanomethyl dialkyl orthoiormate.
lowering the temperature and a ‘75.6% yield of
5. Cyanomethyl diethyl orthoformate.
beta-amihoethyl diethyl orthoformate, a colorless
liquid having a boiling point of 88° C. at 10 mm.
DONALD J. LODER.
WILLIAM F. GRESHAM.
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