US4408079A
Expired / Lapsed
US
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Preparation of alpha-alkylacroleins
Assignee: BASF SE
•
Filing: 1982-01-15
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Granted: 1983-10-04
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Expires: 2002-01-15
Abstract
Abstract α-Alkylacroleins are prepared by reacting an alkanal with formaldehyde and a secondary amine in the presence of a carboxylic, dicarboxylic or polycarboxylic acid in certain molar ratios within a pH range of from 2.5 to 7 and at from 0° to 150° C. The α-alkylacroleins which can be prepared by the process described are valuable starting materials for dyes, drugs and pest control agents.
Inventors
- 👤 Franz Merger
- 👤 Hans-Juergen Foerster
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 12:25
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/75
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
153 words
A process for the preparation of an α-alkylacrolein of the formula ##STR6## where R 1 is an aliphatic radical, by reacting an alkanal of the formula R.sup.1 -CH.sub.2 -CHO II where R 1 has the above meaning, with formaldehyde and a secondary amine in the presence of an acid, wherein the reaction is carried out with a molar ratio of starting material II to formaldehyde of 0.9-1.5:1, at a pH of 2.5-7 and at form 0° to 150° C. in the presence of (a) between 0.05 and 1.5 equivalents of an aliphatic monocarboxylic acid of 2 to 10 carbon atoms per mole of starting material II or (b) between 0.3 and 1.25 equivalents of a dicarboxylic or polycarboxylic acid of 2 to 10 carbon atoms per mole of starting substance II, as the acid, and in the presence of a secondary amine, using an equivalent ratio of carboxylic acid to amine of 1-2:1.
Claim 2
Dependent Claim
153 words
A process for the preparation of an α-alkylacrolein of the formula ##STR6## where R 1 is an aliphatic radical, by reacting an alkanal of the formula R.sup.1 -CH.sub.2 -CHO II where R 1 has the above meaning, with formaldehyde and a secondary amine in the presence of an acid, wherein the reaction is carried out with a molar ratio of starting material II to formaldehyde of 0.9-1.5:1, at a pH of 2.5-7 and at form 0° to 150° C. in the presence of (a) between 0.05 and 1.5 equivalents of an aliphatic monocarboxylic acid of 2 to 10 carbon atoms per mole of starting material II or (b) between 0.3 and 1.25 equivalents of a dicarboxylic or polycarboxylic acid of 2 to 10 carbon atoms per mole of starting substance II, as the acid, and in the presence of a secondary amine, using an equivalent ratio of carboxylic acid to amine of 1-2:1.
Claim 3
Dependent Claim
26 words
The process as claimed in claim 1, wherein the reaction is carried out with 0.95 to 1.2 moles of starting material II per mole of formaldehyde.
Claim 4
Dependent Claim
35 words
The process as claimed in claim 1, wherein the reaction is carried out with from 0.06 to 1.4 equivalents of monocarboxylic acid and 0.05 to 1.5 equivalents of amine per mole of starting material II.
Claim 5
Dependent Claim
38 words
The process as claimed in claim 1, wherein the reaction is carried out with from 0.05 to 1.5 equivalents of dicarboxylic or polycarboxylic acid and from 0.01 to 1.5 equivalents of amine per mole of starting material II.
Claim 6
Dependent Claim
24 words
The process as claimed in claim 1, wherein the reaction is carried out with an equivalent ratio of carboxylic acid to amine of 1.05-1.8:1.
Claim 7
Dependent Claim
16 words
The process as claimed in claim 1, wherein the reaction is carried out at pH 3-6.5.
Claim 8
Dependent Claim
19 words
The process as claimed in claim 1, wherein the reaction is carried out at from 20° to 130° C.
Claim 9
Dependent Claim
38 words
The process of claim 1, wherein R 1 is an unsubstituted alkyl of 1 to 4 carbon atoms or an alkyl of 1 to 4 carbon atoms substituted by alkoxy or alkyl of 1 to 4 carbon atoms.
Claim 10
Dependent Claim
20 words
The process of claim 1, wherein R 1 is propanal, n-butanal, 3-methylbutanal, n-pentanal, 3-methylhexanal, 3-ethylpentanal, 4-methylhexanal, n-heptanal, n-nonanal or n-decanal.
Claim 11
Dependent Claim
10 words
The process of claim 1, wherein R 1 is propanal.
References Cited (Backward Citations)
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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) | 1986-10-03 | 1987-04-04 | 1987-10-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-03 | 1991-04-04 | 1991-10-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-03 | 1995-04-04 | 1995-10-04 | $7700.00 | Window Closed / Lapsed |