US4143068A
Expired / Lapsed
US
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Process for the preparation of acyl cyanide compounds
Assignee: Bayer AG
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Filing: 1977-03-11
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Granted: 1979-03-06
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Expires: 1997-03-11
Abstract
Abstract Acyl cyanides of the formula ##STR1## wherein R is alkyl or substituted alkyl with 1 to 8 carbon atoms, or cyano-carbonyl substituted alkyl, i.e., containing another ##STR2## group, cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms or aryl or substituted aryl or represents an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, Are made by reacting the corresponding acid halide with an alkali metal cyanide or anhydrous hydrocyanic acid in the presence of a heavy metal cyanide and optionally in the presence of a diluent, at a temperature of between 100° C. and 300° C.
Inventors
- 👤 Kurt Findeisen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 05:09
CPC Classifications
C; C07; C07C; C07C253/00; C07C253/14
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
315 words
Process for the preparation of acyl cyanide ##STR12## wherein R is alkyl or substituted alkyl with 1 to 8 carbon atoms, wherein the substituents are selected from alkoxy or carbalkoxy of up to 4 carbon atoms in the alkoxy moiety, nitro, nitrile and halo; cyano-carbonyl substituted alkyl; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms wherein the substituent is selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in each alkyl moiety, nitro, nitrile and halo; aryl or substituted aryl wherein the substitutents are selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in the alkyl moiety, nitro and halo; or represents an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, wherein said substituents are selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in each alkyl moiety, nitro, nitrile and halo; which process comprises reacting an acid halide of the formula ##STR13## wherein R' is alkyl or substituted alkyl with 1 to 8 carbon atoms, wherein the substituents are selected from alkoxy or carbalkoxy of up to 4 carbon atoms in the alkoxy moiety, nitro, nitrile and halo; or ##STR14## substituted alkyl; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms wherein the substituent is selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in each alkyl moiety, nitro, nitrile and halo; aryl or substituted aryl wherein the substituents are selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in the alkyl moiety, nitro and halo; or represents an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, and X is halogen, with an alkali metal cyanide or anhydrous hydrocyanic acid in the presence of a heavy metal cyanide, at a temperature of between 100° C. and 300° C.
Claim 2
Dependent Claim
315 words
Process for the preparation of acyl cyanide ##STR12## wherein R is alkyl or substituted alkyl with 1 to 8 carbon atoms, wherein the substituents are selected from alkoxy or carbalkoxy of up to 4 carbon atoms in the alkoxy moiety, nitro, nitrile and halo; cyano-carbonyl substituted alkyl; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms wherein the substituent is selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in each alkyl moiety, nitro, nitrile and halo; aryl or substituted aryl wherein the substitutents are selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in the alkyl moiety, nitro and halo; or represents an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, wherein said substituents are selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in each alkyl moiety, nitro, nitrile and halo; which process comprises reacting an acid halide of the formula ##STR13## wherein R' is alkyl or substituted alkyl with 1 to 8 carbon atoms, wherein the substituents are selected from alkoxy or carbalkoxy of up to 4 carbon atoms in the alkoxy moiety, nitro, nitrile and halo; or ##STR14## substituted alkyl; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms wherein the substituent is selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in each alkyl moiety, nitro, nitrile and halo; aryl or substituted aryl wherein the substituents are selected from alkyl, alkoxy and carbalkoxy of up to 4 carbon atoms in the alkyl moiety, nitro and halo; or represents an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, and X is halogen, with an alkali metal cyanide or anhydrous hydrocyanic acid in the presence of a heavy metal cyanide, at a temperature of between 100° C. and 300° C.
Claim 3
Dependent Claim
18 words
Process as claimed in claim 1 wherein the reaction is carried out in the presence of a diluent.
Claim 4
Dependent Claim
10 words
Process as claimed in claim 1 wherein R is alkyl.
Claim 5
Dependent Claim
11 words
Process as claimed in claim 1 wherein R is substituted alkyl.
Claim 6
Dependent Claim
15 words
Process as claimed in claim 1 wherein R is alkyl substituted with a ##STR15## group.
Claim 7
Dependent Claim
21 words
Process as claimed in claim 1 wherein R is cycloalkyl or substituted cycloalkyl of from 5 to 6 ring carbon atoms.
Claim 8
Dependent Claim
48 words
Process as claimed in claim 1 wherein R is aryl or substituted aryl selected from phenyl and naphthyl and wherein the substituents are selected from alkyl of up to 4 carbon atoms, alkoxy or carbalkoxy of up to 4 carbon atoms in the alkyl moiety, nitrogen and halogen.
Claim 9
Dependent Claim
30 words
Process as claimed in claim 1 wherein R is a 5- or 6membered heterocyclic radical wherein the hetero atoms are selected from 1 to 3 oxygen, sulfur and nitrogen atoms.
Claim 10
Dependent Claim
15 words
Process as claimed in claim 1 wherein R' is alkyl substituted with an ##STR16## group.
Claim 11
Dependent Claim
211 words
Process as claimed in claim 1 wherein R' is straight-chain or branched alkyl or substituted alkyl of from 1 to 4 carbon atoms, and the substitutents are selected from alkoxy of from 1 to 4 carbon atoms, carbalkoxy with from 1 to 4 carbon atoms, in the alkoxy group, nitro, nitrile and halogen; cycloalkyl or substituted cycloalkyl of from 5 or 6 carbon atoms in the ring system, and the substituents are selected from alkyl with 1 to 4 carbon atoms, alkoxy or carbalkoxy with, in either case, up to 4 carbon atoms in the alkyl part, nitro, nitrile and halogen; phenyl or naphthyl, substituted phenyl or naphthyl, where the substituents are selected from alkyl with 1 to 4 carbon atoms, alkoxy or carbalkoxy with, in each case, up to 4 carbon atoms in the alkyl part, nitro and halogen; or a 5-membered or 6-membered heterocyclic radical which can contain 1 to 3 hetero atoms selected from oxygen, sulfur and nitrogen in the ring and which may be substituted with substituents selected from alkyl, with 1 to 4 carbon atoms, alkoxy or carbalkoxy with, in either case, up to 4 carbon atoms in the alkyl part, nitro, nitrile and halogen, and which heterocyclic radical may be fused with a benzene ring.
Claim 12
Dependent Claim
13 words
Process as claimed in claim 1 wherein X is fluorine, chlorine or bromine.
Claim 13
Dependent Claim
16 words
Process as claimed in claim 1 wherein the reaction temperature is between 150° and 250° C.
Claim 14
Dependent Claim
28 words
Process as claimed in claim 1 wherein the acid halide of the formula II is employed in at least a stoichiometric amount, relative to the alkali metal cyanide.
Claim 15
Dependent Claim
21 words
Process as claimed in claim 1 wherein the cyanide reactant is an alkali metal cyanide selected from sodium or potassium cyanide.
Claim 16
Dependent Claim
33 words
Process as claimed in claim 1 wherein the said heavy metal cyanide is copper (I) cyanide, copper (II) cyanide or zinc (II) cyanide or a complex compound thereof with an alkali metal cyanide.
Claim 17
Dependent Claim
12 words
Process as claimed in claim 2 wherein said diluent is a dichlorobenzene.
Claim 18
Dependent Claim
24 words
Process as claimed in claim 1 wherein the acid halide of the formula II is an aromatic acid halide or an aromatic diacid dihalide.
Claim 19
Dependent Claim
15 words
Process as claimed in claim 17 wherein said acid halide (II) is a benzoyl halide.
Claim 20
Dependent Claim
13 words
Process as claimed in claim 18 wherein said benzoyl halide is benzoyl chloride.
Claim 21
Dependent Claim
21 words
Process as claimed in claim 1 wherein said acyl cyanide is benzoyl cyanide and the said acid halide is benzoyl halide.
Claim 22
Dependent Claim
21 words
Process as claimed in claim 1 wherein said acyl cyanide is 3-benzoyl cyanide and the said acid halide is 3-benzoyl halide.
Claim 23
Dependent Claim
22 words
Process as claimed in claim 1 wherein said acyl cyanide is terephthalic acid dicyanide and said halide is a terephthalic acid dihalide.
Claim 24
Dependent Claim
19 words
Process as claimed in claim 1 wherein said acyl cyanide is p-methoxybenzoyl cyanide and said halide is p-methoxybenzoyl halide.
Claim 25
Dependent Claim
19 words
Process as claimed in claim 1 wherein said acyl cyanide is p-ethoxybenzoyl cyanide and said halide is p-ethoxybenzoyl halide.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-05 | 1982-09-04 | 1983-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-05 | 1986-09-04 | 1987-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-05 | 1990-09-04 | 1991-03-06 | $7700.00 | Window Closed / Lapsed |