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US3965193A
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Production of high molecular weight α,β-unsaturated aldehydes
Assignee: BASF SE
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Filing: 1972-11-01
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Granted: 1976-06-22
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Expires: 1992-11-01
Abstract
Abstract A process for the production of high molecular weight α, β-unsaturated aldehydes by alkylation of the γ-carbon atom of a lower molecular weight α, β-unsaturated aldehyde with a substituted allyl alcohol which has a chain branching in the 3-position carbon atom or a phenyl radical in the 3-position or of a corresponding allyl alcohol carboxylic ester at elevated temperature in the liquid phase. The products are valuable intermediates for the production of natural substances and odorants.
Inventors
- 👤 Norbert Goetz
- 👤 Roman Fischer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:43
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/04; C07D319/06; C07C; C07C403/00; C07C403/14; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
286 words
A process for the production of high molecular weight α,β-unsaturated aldehydes of the general formula (I): ##EQU7## where R 1 is hydrogen, alkyl of one to four carbon atoms, phenyl or phenyl bearing alkyl of one to four carbon atoms as a substituent; R 2 is hydrogen, alkyl of one to four carbon atoms, phenyl or phenyl bearing alkyl of one to four carbon atoms as a substituent; R 3 is hydrogen or alkyl of one to four carbon atoms; R 5 is hydrogen or alkyl of one to four carbon atoms; R 6 is hydrogen or alkyl of one to four carbon atoms; R 7 is hydrogen or alkyl of one to four carbon atoms; R 4 is hydrogen or a saturated or unsaturated, branched or linear aliphatic or cycloaliphatic hydrocarbon radical of one to twelve carbon atoms; R 8 is alkyl of one to four carbon atoms or (when R 9 is phenyl) hydrogen; and R 9 is a saturated or unsaturated branched or linear aliphatic or cycloaliphatic hydrocarbon radical of one to twelve carbon atoms, or phenyl wherein an allyl compound of the formula (II): ##EQU8## in which R 5 to R 9 have the meanings given above and R 10 is hydrogen or acyl of a carboxylic acid of one to five carbon atoms is reacted in the liquid phase with an α,β-unsaturated aldehyde of the formula (III): ##EQU9## in which R 1 to R 4 have the meanings given above, at elevated temperature of about 60°-300°C and in the presence of an acid catalyst wit a pK value of -9 to 6 in such an amount of such acid catalyst that the reaction mixture has a pH of 1 to 7.
Claim 2
Dependent Claim
286 words
A process for the production of high molecular weight α,β-unsaturated aldehydes of the general formula (I): ##EQU7## where R 1 is hydrogen, alkyl of one to four carbon atoms, phenyl or phenyl bearing alkyl of one to four carbon atoms as a substituent; R 2 is hydrogen, alkyl of one to four carbon atoms, phenyl or phenyl bearing alkyl of one to four carbon atoms as a substituent; R 3 is hydrogen or alkyl of one to four carbon atoms; R 5 is hydrogen or alkyl of one to four carbon atoms; R 6 is hydrogen or alkyl of one to four carbon atoms; R 7 is hydrogen or alkyl of one to four carbon atoms; R 4 is hydrogen or a saturated or unsaturated, branched or linear aliphatic or cycloaliphatic hydrocarbon radical of one to twelve carbon atoms; R 8 is alkyl of one to four carbon atoms or (when R 9 is phenyl) hydrogen; and R 9 is a saturated or unsaturated branched or linear aliphatic or cycloaliphatic hydrocarbon radical of one to twelve carbon atoms, or phenyl wherein an allyl compound of the formula (II): ##EQU8## in which R 5 to R 9 have the meanings given above and R 10 is hydrogen or acyl of a carboxylic acid of one to five carbon atoms is reacted in the liquid phase with an α,β-unsaturated aldehyde of the formula (III): ##EQU9## in which R 1 to R 4 have the meanings given above, at elevated temperature of about 60°-300°C and in the presence of an acid catalyst wit a pK value of -9 to 6 in such an amount of such acid catalyst that the reaction mixture has a pH of 1 to 7.
Claim 3
Dependent Claim
44 words
A process as claimed in claim 1 carried out in the presence of 0.01 to 10% by weight based on the sum of the reactants of an acid of the pK from about 3 to 6 at a temperature of from 60° to 300°C.
Claim 4
Dependent Claim
19 words
A process as claimed in claim 2 wherein the amount of said acid is 0.1 to 3% by weight.
Claim 5
Dependent Claim
45 words
A process as claimed in claim 1 carried out in the presence of 0.01 to 1% by weight based on the sum of the reactants of an acid of a pK of from -9 to about 3 at a temperature of from 60° to 300°C.
Claim 6
Dependent Claim
21 words
A process as claimed in claim 4 wherein the amount of said acid used is from 0.01 to 0.5% by weight.
Claim 7
Dependent Claim
20 words
A process as claimed in claim 1 wherein water formed in the reaction is removed continuously from the reaction mixture.
Claim 8
Dependent Claim
28 words
A process as claimed in claim 1 carried out under the vapor pressure of the reactants which is set up in a pressuretight vessel under the reaction conditions.
Claim 9
Dependent Claim
31 words
A process as claimed in claim 1 wherein said allyl compound has the formula (IIa): ##EQU10## in which n is 1, 2 or 3 and R 7 is hydrogen or methyl.
Claim 10
Dependent Claim
18 words
A process as claimed in claim 1 wherein an allyl compound of formula (II) is reacted with 3,3-dimethylacrolein.
Claim 11
Dependent Claim
13 words
A process as claimed in claim 1 wherein 3-methyl-2-buten-1-ol is reacted with 3,3-dimethylacrolein.
Claim 12
Dependent Claim
13 words
A process as claimed in claim 1 wherein geraniol is reacted with 3,3-dimethylacrolein.
Claim 13
Dependent Claim
13 words
A process as claimed in claim 1 wherein ionylidenethanol is reacted with 3,3-dimethylacrolein.
References Cited (Backward Citations)
GB1020728A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |