US3981907A
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Method of producing highly unsaturated compounds by reacting 1,3-conjugated diene compounds with derivatives of dimers of butadienes and products
Assignee: Mitsubishi Chemical Corp
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Filing: 1975-03-18
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Granted: 1976-09-21
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Expires: 1995-03-18
Abstract
Abstract A 1,3-conjugated diene compound and a derivative of a butadiene dimer are subjected to an addition reaction over a rhodium compound. The 1,3-conjugated diene compound adds to the derivative in a molar ratio of 1:1. The derivative may be an ester, ether or alcohol. Said derivative is obtained either by reacting a carboxylic acid, an alcohol or a phenol with a butadiene over a palladium catalyst or by hydrolyzing the reaction product.
Inventors
- 👤 Saburo Hattori
- 👤 Yoshiharu Morita
- 👤 Yoshio Ihashi
- 👤 Tadao Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 09:36
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/02; C07C69/12; C07C69/14; C07C69/145; C07C67/00; C07C67/30; C07C67/333; C07C67/343
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
148 words
A method for the production of an alkapolyenyl group containing ester in which one molecule of a 1,3-conjugated diene bond containing compound is linked to an alkadienyl group of said ester and which has at least 12 carbon atoms and at least 3 carbon-carbon double bonds, characterized in that an alkadienyl ester represented by the formula ##EQU9## in which R is methyl, ethyl, propyl or phenyl and each R 1 is independently selected from the group consisting of hydrogen and methyl, is reacted in the presence of a rhodium compound catalyst selected from the group consisting of rhodium chloride, rhodium bromide, rhodium nitrate, rhodium acetate, rhodium propionate, rhodium acetylacetonate, π- allyl - rhodium chloride, tetrakis(ethylene)dischlorodirhodium and bis(cycloocta-1,5-diene)dichlorodirhodium, with a 1,3-conjugated diene bond containing compound selected from the group consisting of 1,3-butadiene, isoprene and straight-chain dimers thereof, the reaction being conducted at a temperature in the range of 50°-250°C.
Claim 2
Independent Claim
148 words
A method for the production of an alkapolyenyl group containing ester in which one molecule of a 1,3-conjugated diene bond containing compound is linked to an alkadienyl group of said ester and which has at least 12 carbon atoms and at least 3 carbon-carbon double bonds, characterized in that an alkadienyl ester represented by the formula ##EQU9## in which R is methyl, ethyl, propyl or phenyl and each R 1 is independently selected from the group consisting of hydrogen and methyl, is reacted in the presence of a rhodium compound catalyst selected from the group consisting of rhodium chloride, rhodium bromide, rhodium nitrate, rhodium acetate, rhodium propionate, rhodium acetylacetonate, π- allyl - rhodium chloride, tetrakis(ethylene)dischlorodirhodium and bis(cycloocta-1,5-diene)dichlorodirhodium, with a 1,3-conjugated diene bond containing compound selected from the group consisting of 1,3-butadiene, isoprene and straight-chain dimers thereof, the reaction being conducted at a temperature in the range of 50°-250°C.
Claim 3
Dependent Claim
22 words
The method according to claim 1 in which the alkadienyl ester is 1-acyloxy-2,7-octadiene, and the 1,3-conjugated diene bond containing compound is 1,3-butadiene.
Claim 4
Dependent Claim
22 words
The method according to claim 1 in which the alkadienyl ester is 1-acyloxy-2,7-octadiene, and the 1,3-conjugated diene bond containing compound is isoprene.
Claim 5
Dependent Claim
22 words
The method according to claim 1 in which the alkadienyl ester is 1-acyloxy-2,7-octadiene, and the 1,3-conjugated diene bond containing compound is 1,3,7-octatriene.
Claim 6
Dependent Claim
13 words
The method according to claim 1 in which the alkadienyl ester is 1-acetoxy-2,7-octadiene.
Claim 7
Dependent Claim
18 words
The method according to claim 1 in which the rhodium compound is an organic acid salt of rhodium.
Claim 8
Dependent Claim
15 words
The method according to claim 1 in which the rhodium compound is a rhodium complex.
Claim 9
Dependent Claim
18 words
The method according to claim 1 in which the rhodium compound is an inorganic acid salt of rhodium.
Claim 10
Dependent Claim
20 words
The method according to claim 8 in which the inorganic acid salt of rhodium is rhodium chloride or rhodium bromide.
Claim 11
Independent Claim
23 words
A method for the production of acetoxy-dodecatriene, characterized in reacting 1,3-butadiene with 1-acetoxy-2,7-octadiene in the presence of a rhodium chloride catalyst at 50°-250°C.
Claim 12
Independent Claim
23 words
A method for the production of acetoxy-dodecatriene, characterized in reacting 1,3-butadiene with 1-acetoxy-2,7-octadiene in the presence of a rhodium chloride catalyst at 50°-250°C.
Claim 13
Dependent Claim
1 words
1-acetoxy-2(2-butenyl)-3,7-octadiene.
Claim 14
Dependent Claim
1 words
1-acetoxy-2(2-butenyl)-3,7-octadiene.
Claim 15
Dependent Claim
1 words
1-acetoxy-2-(2-butenyl)-2,7-octadiene.
Claim 16
Dependent Claim
1 words
1-acetoxy-2-(2-butenyl)-2,7-octadiene.
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) | 1979-09-21 | 1980-03-22 | 1980-09-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-21 | 1984-03-22 | 1984-09-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-21 | 1988-03-22 | 1988-09-21 | $7700.00 | Window Closed / Lapsed |