Patent US3570350A successfully refreshed from Google Patents.
US4550195A
Expired / Lapsed
US
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Manufacture of pent-3-enoic acid and its alkyl esters
Assignee: BASF SE
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Filing: 1981-08-21
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Granted: 1985-10-29
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Expires: 2001-08-21
Abstract
Abstract A process for the manufacture of pent-3-enoic acid and its alkyl esters, of the general formula CH.sub.3 --CH═CH--CH.sub.2 --CO--OR where R is hydrogen or alkyl of 1 to 4 carbon atoms, comprising carbonylating butadiene with carbon monoxide and a compound ROH at from 300 to 1,000 bars CO pressure and from 100° to 160° C. in the presence of cobalt catalysts and nitrogen bases, wherein C 4 cuts are used as starting materials and a tertiary amine having a pK A of from 3 to 11 is used as the nitrogen base. The pent-3-enoic acid or alkyl esters produced may be used for the manufacture of adipic acid or its alkyl esters, which compounds are starting materials for the manufacture of nylons.
Inventors
- 👤 Rolf Platz
- 👤 Rudolf Kummer
- 👤 Heinz-Walter Schneider
- 👤 Kurt Schwirten
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 01:55
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/10; C07C51/14
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
159 words
In a process for the manufacture of pent-3-enoic acid alkyl esters of the formula I CH.sub.3 --CH═CH--CH.sub.2 --CO--OR I where R is alkyl of 1 to 4 carbon atoms in which butadiene is carbonylated with carbon monoxide and a compound ROH where R is defined as above at from 300 to 1,000 bars carbon monoxide pressure and a temperature of from 80° to 160° C. in the presence of cobalt catalysts and nitrogen bases, the improvement which comprises: using as the butadiene to be carbonylated a C 4 hydrocarbon cut containing butadiene, butenes, butynes and butanes and selectively carbonylating butadiene by using as the nitrogen base a tertiary amine having a pK a of from 3 to 11 in an amount of from about 0.5 to 1 mole of tertiary amine per mole of butenes contained in the C 4 cut, whereby the butadiene is selectively reacted whereas the other components of the C 4 cut remain essentially unreacted.
Claim 2
Dependent Claim
159 words
In a process for the manufacture of pent-3-enoic acid alkyl esters of the formula I CH.sub.3 --CH═CH--CH.sub.2 --CO--OR I where R is alkyl of 1 to 4 carbon atoms in which butadiene is carbonylated with carbon monoxide and a compound ROH where R is defined as above at from 300 to 1,000 bars carbon monoxide pressure and a temperature of from 80° to 160° C. in the presence of cobalt catalysts and nitrogen bases, the improvement which comprises: using as the butadiene to be carbonylated a C 4 hydrocarbon cut containing butadiene, butenes, butynes and butanes and selectively carbonylating butadiene by using as the nitrogen base a tertiary amine having a pK a of from 3 to 11 in an amount of from about 0.5 to 1 mole of tertiary amine per mole of butenes contained in the C 4 cut, whereby the butadiene is selectively reacted whereas the other components of the C 4 cut remain essentially unreacted.
Claim 3
Dependent Claim
48 words
A process as set forth in claim 1 wherein the C 4 cut is made up of the following components: ______________________________________
butadiene 10-70%, by weight
isobutene 15-40%, by weight
but-1-ene 10-40%, by weight
but-2-ene 5-20%, by weight
butanes 1-10%, by weight
and butynes 0.1- 3%, by weight.
______________________________________
Claim 4
Dependent Claim
23 words
A process as set forth in claim 1 wherein C 4 cuts containing from 40 to 60% by weight of butadiene are used.
Claim 5
Dependent Claim
48 words
A process as set forth in claim 1 wherein the C 4 cut is made up of the following components: ______________________________________
butadiene 40-60%, by weight
isobutene 20-35%, by weight
but-1-ene 10-25%, by weight
but-2-ene 5-15%, by weight
butanes 1-10%, by weight
and butynes 0.1- 3%, by weight.
______________________________________
Claim 6
Dependent Claim
12 words
A process as set forth in claim 1 wherein R is methyl.
Claim 7
Dependent Claim
20 words
A process as set forth in claim 5 wherein 1 mole of tertiary amine is used per mole of butenes.
Claim 8
Dependent Claim
16 words
A process as set forth in claim 6 wherein isoquinoline is used as the tertiary amine.
Claim 9
Dependent Claim
18 words
A process as set forth in claim 1, wherein pyridine or isoquinoline is used as the nitrogen base.
Claim 10
Dependent Claim
19 words
A process as set forth in claim 1, wherein the temperature is maintained at from 100° to 140° C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-10-28 | 1989-04-29 | 1989-10-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-28 | 1993-04-29 | 1993-10-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-28 | 1997-04-29 | 1997-10-29 | $7700.00 | Window Closed / Lapsed |