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US4156690A
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Method for preparing unsaturated nitriles
Assignee: POLAK'S FRUTAL WORKS Inc
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Filing: 1976-12-01
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Granted: 1979-05-29
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Expires: 1996-12-01
Abstract
Abstract Alpha, beta-dialkyl conjugated nitriles are disclosed which have interesting perfumistic qualities. These materials have the general structural formula <IMAGE> where R is an aliphatic hydrocarbon radical of about 1 to 15 carbon atoms having no unsaturation in conjugated relationship with either the nitrile unsaturation or the alpha, beta-olefinic unsaturation, and R' and R'' are the same or different aliphatic hydrocarbon radicals meeting the description of R, or R' and R'', taken together, form a cycloaliphatic radical having about 6 to 15 carbon atoms. They are produced by the reaction of the appropriate aliphatic nitrile and ketone under the influence of a basic catalyst.
Inventors
- 👤 Robert S. DeSimone
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 09:09
CPC Classifications
C; C07; C07C; C07C255/00; C11; C11B; C11B9/00; C11B9/0007; C11B9/0023; C11B9/0026
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
123 words
A method of preparing an aliphatic nitrile having the formula ##STR6## wherein R is an alkyl or alkylene radical of about 1 to 15 carbon atoms free of unsaturation in conjugated relationship with the nitrile or the olefinic unsaturation, and R' and R" are the same or different radicals meeting the description of R; or R' and R" taken together represent a cycloaliphatic radical having 6 to 15 carbon atoms, which method comprises reacting a ketone of the formula ##STR7## with a nitrile of the formula R--CH 2 -C.tbd.N in the presence of about 0.1 to 10 moles per mole of ketone of a basic catalyst selected from the class consisting of alkali metal hydroxides, alkali earth metal hydroxides, and quaternary ammonium hydroxides.
Claim 2
Independent Claim
123 words
A method of preparing an aliphatic nitrile having the formula ##STR6## wherein R is an alkyl or alkylene radical of about 1 to 15 carbon atoms free of unsaturation in conjugated relationship with the nitrile or the olefinic unsaturation, and R' and R" are the same or different radicals meeting the description of R; or R' and R" taken together represent a cycloaliphatic radical having 6 to 15 carbon atoms, which method comprises reacting a ketone of the formula ##STR7## with a nitrile of the formula R--CH 2 -C.tbd.N in the presence of about 0.1 to 10 moles per mole of ketone of a basic catalyst selected from the class consisting of alkali metal hydroxides, alkali earth metal hydroxides, and quaternary ammonium hydroxides.
Claim 3
Dependent Claim
14 words
The method of claim 1 wherein the basic catalyst is an alkali metal hydroxide.
Claim 4
Dependent Claim
12 words
The method of claim 2 wherein the basic catalyst is potassium hydroxide.
Claim 5
Dependent Claim
24 words
The method of claim 3 wherein the potassium hydroxide is present in the amount of about 0.1 to 5 moles per mole of ketone.
Claim 6
Dependent Claim
14 words
The method of claim 2 wherein the basic catalyst is a quaternary ammonium hydroxide.
Claim 7
Dependent Claim
15 words
The method of claim 1 wherein the basic catalyst is an alkaline earth metal hydroxide.
Claim 8
Independent Claim
104 words
A method of preparing an aliphatic nitrile having the formula ##STR8## wherein R is an alkyl or alkylene radical of about 1-15 carbon atoms free of unsaturation in conjugated relationship with the nitrile or the olefinic unsaturation, and R' and R" are the same or different radicals meeting the description of R or R' and R" taken together represent a cycloaliphatic radical having 6-15 carbon atoms, which method comprises reacting a ketone of the formula ##STR9## with a nitrile of the formula R--CH 2 C.tbd.N in the presence of a phase transfer agent and about 0.1-10 moles per mole of ketone of calcium hydroxide.
Claim 9
Independent Claim
104 words
A method of preparing an aliphatic nitrile having the formula ##STR8## wherein R is an alkyl or alkylene radical of about 1-15 carbon atoms free of unsaturation in conjugated relationship with the nitrile or the olefinic unsaturation, and R' and R" are the same or different radicals meeting the description of R or R' and R" taken together represent a cycloaliphatic radical having 6-15 carbon atoms, which method comprises reacting a ketone of the formula ##STR9## with a nitrile of the formula R--CH 2 C.tbd.N in the presence of a phase transfer agent and about 0.1-10 moles per mole of ketone of calcium hydroxide.
Claim 10
Dependent Claim
22 words
The method of claim 7 wherein the reaction is carried out in the presence of calcium hydroxide as a water trapping agent.
Claim 11
Dependent Claim
14 words
The method of claim 8 wherein the phase transfer agent is tetramethyl ammonium hydroxide.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |