US4016220A
Expired / Lapsed
US
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Process for the preparation of 9-tricosene and 9-heneicosene
Assignee: Huels AG
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Filing: 1976-02-12
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Granted: 1977-04-05
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Expires: 1996-02-12
Abstract
Abstract Higher alkenes with a double bond in the 9-position, e.g. 9-tricosene and/or 9-heneicosene, are economically prepared by a metathesis reaction of suitable alkene starting materials.
Inventors
- 👤 Friedrich-Wilhelm Kupper
- 👤 Roland Streck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:45
CPC Classifications
C; C07; C07C; C07C6/00; C07C6/02; C07C6/04; C07C2521/00; C07C2521/02; C07C2521/04; C07C2523/00; C07C2523/02; C07C2523/04; C07C2523/16; C07C2523/24; C07C2523/28; C07C2523/32; C07C2523/36; C07C2527/00; C07C2527/06; C07C2527/132; C07C2531/00; C07C2531/02; C07C2531/12; C07C2531/14; C07C2531/26; C07C2531/34
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
117 words
A process for preparing a compound selected from the group consisting of 9-tricosene, 9-heneicosene and mixtures thereof, which comprises metathetically reacting: a. an alkene of at least 10 carbon atoms having an n-nonylidene radical; b. at least one member selected from the group consisting of an alkene of at least 13 carbon atoms having an n-dodecylidene radical and an alkene of at least 15 carbon atoms having a n-tetradecylidene radical; and c. a catalytic amount of an olefin metathesis catalyst substantially free of oligomerization and isomerization activity with respect to said reactants, said catalyst comprising a compound of a metal in Group VB to VIIB of the Periodic Table to form said 9-tricosene, 9-heneicosene or mixtures thereof.
Claim 2
Dependent Claim
117 words
A process for preparing a compound selected from the group consisting of 9-tricosene, 9-heneicosene and mixtures thereof, which comprises metathetically reacting: a. an alkene of at least 10 carbon atoms having an n-nonylidene radical; b. at least one member selected from the group consisting of an alkene of at least 13 carbon atoms having an n-dodecylidene radical and an alkene of at least 15 carbon atoms having a n-tetradecylidene radical; and c. a catalytic amount of an olefin metathesis catalyst substantially free of oligomerization and isomerization activity with respect to said reactants, said catalyst comprising a compound of a metal in Group VB to VIIB of the Periodic Table to form said 9-tricosene, 9-heneicosene or mixtures thereof.
Claim 3
Dependent Claim
25 words
A process according to claim 1, wherein said catalyst is a homogeneous metathesis catalyst and the reaction is effected at a temperature of 0°-60° C.
Claim 4
Dependent Claim
22 words
A process according to claim 2, wherein said metathesis catalyst comprises tungsten hexachloride, ethylaluminum dichloride and a catalyst activating amount of ethanol.
Claim 5
Dependent Claim
32 words
A process according to claim 1, wherein said catalyst is a heterogeneous methathesis catalyst deposited on a solid catalyst support material and the reaction is effected at a temperature of 40°-180° C.
Claim 6
Dependent Claim
27 words
A process according to claim 4, wherein said catalyst support is an alkali metal oxide-containing aluminum oxide and said catalyst is an oxide of molybdenum or rhenium.
Claim 7
Dependent Claim
12 words
A process according to claim 5, wherein said catalyst is rhenium heptoxide.
Claim 8
Dependent Claim
22 words
A process according to claim 1, wherein (a) is 1-decene or 9-octadecene and (b) is 2-hexadecene or 1-pentadecene, whereby 9-tricosene is formed.
Claim 9
Dependent Claim
20 words
A process according to claim 1, wherein (a) is 1-decene or 9-octadecene and (b) is 2-tetradecene, whereby 9-heneicosene is formed.
Claim 10
Dependent Claim
32 words
A process according to claim 1, wherein (a) is 1-decene or 9-octadecene and (b) is a mixture of 2-tetradecene with 2-hexadecene or 1-pentadecene, whereby a mixture of 9-tricosene and 9-heneicosene is formed.
Claim 11
Dependent Claim
41 words
A process according to claim 9, wherein said catalyst is a heterogeneous metathesis catalyst comprising an oxide of molybdenum or rhenium deposited on an alkali metal oxide-containing aluminum oxide support and said reaction is effected at a temperature of 50°-120° C.
Claim 12
Dependent Claim
12 words
A process according to claim 10, wherein said oxide is rhenium heptoxide.
Claim 13
Dependent Claim
37 words
A process according to claim 9, wherein said catalyst is a homogeneous metathesis catalyst comprising tungsten hexachloride, ethylaluminum dichloride and a catalyst activating amount of ethanol and said reaction is effected at a temperature of 10°-40° 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) | 1980-04-04 | 1980-10-04 | 1981-04-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-04 | 1984-10-04 | 1985-04-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-04 | 1988-10-04 | 1989-04-05 | $7700.00 | Window Closed / Lapsed |