US3855255A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of higher, polyunsaturated carboxylic acid ester and free acids
Assignee: Henkel AG and Co KGaA
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Filing: 1971-05-25
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Granted: 1974-12-17
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Expires: 1991-05-25
Abstract
Abstract A process for the preparation of higher, polyunsaturated carboxylic acid esters consisting essentially of the steps of reacting a conjugated diolefin with an alkyl ester of methacrylic acid in a ratio of at least 4 mols of diolefin per mol of methacrylic acid ester, in the presence of an organo-metal complex of zero-valent nickel and of an electron donor selected from the group consisting of phosphorous acid triamides, heterocyclic N-bases, aliphatic and aromatic amines, nitriles, sulfides, sulfoxides and triaryl compounds of arsenic and antimony, and recovering said higher, polyunsaturated carboxylic acid ester having more than 19 carbon atoms in the acid moiety. The reaction products are co-oligomerizates of four molecules of conjugated dienes and one molecule of methacrylic acid ester. The ester may be saponified to obtain the free carboxylic acid having more than 19 carbon atoms.
Inventors
- 👤 M Dohr
- 👤 H Singer
- 👤 W Umbach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:48
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/09
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
102 words
IN THE PROCESS FOR THE PREPARATION OF HIGHER, POLYUNSATURATED CARBOXYLIC ACID ESTERS COMPRISING THE STEPS OF REACTING A CONJUGATED DIOLEFIN WITH A LOWE ALKYL METHACRYLATE, IN THE OF AT LEAST 4 MOLS OF DIOLEFIN PER MOL OF METHACRYLATE, IN THE PRESENCE OF AN ORGANO-METAL COMPLEX OF ZERO-VALENT NICKEL AND OF AN ELECTRON DONOR, AND FECIVEING A HIGHER, POLYUNSATURATED CARBOXYLIC ACID ASTER HAVING MORE THAN 19 CARBON ATOMS IN THE ACID MOIETY, THE IMPROVEMMENT COMPRISES OF EMPOLYING AN ELECTRON DONOR SELECTED FROM THE GROUP CONSISTING OF PHOSPHOROUS ACID TRIMIDES, MORPHOLINE, N-METHYLMORPHOLINE PIPERADINE, PYRIDINE, THE PICOLINS, COLLIDINE, QUINOLINE, PYRROLE, ALIPHATIC SULFIDES, TRIAYL-ARSINES AND TRIARYL-STIBINES.
Claim 2
Dependent Claim
102 words
IN THE PROCESS FOR THE PREPARATION OF HIGHER, POLYUNSATURATED CARBOXYLIC ACID ESTERS COMPRISING THE STEPS OF REACTING A CONJUGATED DIOLEFIN WITH A LOWE ALKYL METHACRYLATE, IN THE OF AT LEAST 4 MOLS OF DIOLEFIN PER MOL OF METHACRYLATE, IN THE PRESENCE OF AN ORGANO-METAL COMPLEX OF ZERO-VALENT NICKEL AND OF AN ELECTRON DONOR, AND FECIVEING A HIGHER, POLYUNSATURATED CARBOXYLIC ACID ASTER HAVING MORE THAN 19 CARBON ATOMS IN THE ACID MOIETY, THE IMPROVEMMENT COMPRISES OF EMPOLYING AN ELECTRON DONOR SELECTED FROM THE GROUP CONSISTING OF PHOSPHOROUS ACID TRIMIDES, MORPHOLINE, N-METHYLMORPHOLINE PIPERADINE, PYRIDINE, THE PICOLINS, COLLIDINE, QUINOLINE, PYRROLE, ALIPHATIC SULFIDES, TRIAYL-ARSINES AND TRIARYL-STIBINES.
Claim 3
Dependent Claim
30 words
The process of claim 1 including the further steps of saponifying said higher, polyunsaturated carboxylic acid ester and recovering a higher, polyunsaturated carboxylic acid having more than 19 carbon atoms.
Claim 4
Dependent Claim
20 words
The process of claim 1 wherein said conjugated diolefin is selected from the group consisting of butadiene-1,3, isoprene and pentadiene-1,3.
Claim 5
Dependent Claim
11 words
The process of claim 3 wherein said conjugated diolefin is butadiene-1,3.
Claim 6
Dependent Claim
13 words
The process of claim 1 wherein said lower alkyl methacrylate is methyl methacrylate.
Claim 7
Dependent Claim
18 words
The process of claim 1 wherein said reaction is effected at a temperature between about 20*C to 150*C.
Claim 8
Dependent Claim
15 words
The process of claim 1 wherein said reaction is conducted under a protective gas atmosphere.
Claim 9
Dependent Claim
12 words
The process of claim 1 wherein an inert organic solvent is present.
Claim 10
Dependent Claim
69 words
The process of claim 1 wherein said organo-metal complex of zero-valent nickel is formed in situ in the presence of part of said conjugated diene and said electron donor by the reduction of an anhydrous organo-nickel compound by a compound selected from the group consisting of a hydride and an organo-metal compound of metals selected from the group consisting of lithium, sodium, potassium, magnesium, calcium, zinc, boron and aluminum.
Claim 11
Dependent Claim
14 words
The process of claim 1, wherein said electron donor is a phosphorous acid triamide.
Claim 12
Dependent Claim
13 words
The process of claim 1 wherein said electron donor is a triaryl arsine.
Claim 13
Dependent Claim
11 words
The process of claim 1 wherein said electron donor is triaryl-stibine.
References Cited (Backward Citations)
US3660440A
Cited
US3780074A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-16 | 1978-06-17 | 1978-12-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-16 | 1982-06-17 | 1982-12-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-16 | 1986-06-17 | 1986-12-17 | $7700.00 | Window Closed / Lapsed |