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US4320239A
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Reaction products of an olefin, a norbornene and a cyclopentadiene
Assignee: Goodrich Corp
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Filing: 1981-02-13
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Granted: 1982-03-16
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Expires: 2001-02-13
Abstract
Abstract A product mixture of a norbornene and a tetracyclododecene is prepared in any desired mole ratio in the range of 95/5 to 5/95 which comprises heating an olefin, cyclopentadiene, and a norbornene in the respective mole ratio of 1-20/1-5/1-5, at a temperature of 100° to 400° C., 100 to 5000 psi, and 0.1 to 5 hours of residence time.
Inventors
- 👤 Wolfgang Schneider
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 21:48
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/02; C07C2/50; C07C2602/00; C07C2602/36; C07C2602/42; C07C2603/00; C07C2603/56; C07C2603/86
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
83 words
A process for preparing a product mixture containing a norbornene and a tetracyclododecene in a desired molar ratio which is in the range of about 95/5 to 5/95 comprising heating in a reactor an olefin of 2 to 22 carbon atoms, a cyclopentadiene or a dicyclopentadiene, and a norbornene; maintaining ratio of reactants, temperature, pressure, and residence time in the reactor such that formation of the norbornene and the tetracyclododecene is favored; and recovering the norbornene and the tetracyclododecene from the product mixture.
Claim 2
Dependent Claim
83 words
A process for preparing a product mixture containing a norbornene and a tetracyclododecene in a desired molar ratio which is in the range of about 95/5 to 5/95 comprising heating in a reactor an olefin of 2 to 22 carbon atoms, a cyclopentadiene or a dicyclopentadiene, and a norbornene; maintaining ratio of reactants, temperature, pressure, and residence time in the reactor such that formation of the norbornene and the tetracyclododecene is favored; and recovering the norbornene and the tetracyclododecene from the product mixture.
Claim 3
Dependent Claim
101 words
Process of claim 1 wherein the olefin is selected from monoolefins and diolefins of 2 to 12 carbon atoms, and the norbornene and the tetracyclododecene are defined respectively as follows: ##STR2## where R 1 and R 2 are independently selected from hydrogen, alkyl and alkylene groups of 1 to 20 carbon atoms, provided that total number of carbon atoms for R 1 and R 2 does not exceed 20; and where R 1 and R 2 , together with the ring carbons to which they are bonded, form one or two saturated or unsaturated rings of 6 to 16 carbon atoms.
Claim 4
Dependent Claim
25 words
Process of claim 3 wherein R 1 and R 2 are independently selected from hydrogen, alkyl and alkylene groups of 1 to 10 carbon atoms.
Claim 5
Dependent Claim
44 words
Process of claim 3 wherein the olefin contains 2 to 4 carbon atoms; and R 1 and R 2 are individually selected from hydrogen and alkyl groups of 1 to 2 carbon atoms, provided that one of R 1 and R 2 is hydrogen.
Claim 6
Dependent Claim
32 words
Process of claim 3 wherein temperature of the reaction is in the range of 100° to 400° C., pressure is 100 to 5000 psi, and residence time of 0.1 to 5 hours.
Claim 7
Dependent Claim
32 words
Process of claim 4 wherein the reaction is carried out at a temperature of 200° to 300° C., pressure of 500 to 4000 psi, and residence time of 0.5 to 2 hours.
Claim 8
Dependent Claim
42 words
Process of claim 3 wherein the relative ratio of the reactants is as follows: 1 to 20 moles of the olefin, 1 to 5 moles of cyclopentadiene or one-half of this amount of dicyclopentadiene, and 1 to 5 moles of the norbornene.
Claim 9
Dependent Claim
42 words
Process of claim 4 wherein the relative ratio of the reactants is as follows: 2 to 10 moles of the olefin, 1 to 5 moles of cyclopentadiene or one-half of this amount of dicyclopentadiene, and 1 to 5 moles of the norbornene.
Claim 10
Dependent Claim
42 words
Process of claim 8 wherein the reaction is conducted at a relatively high temperature of the range of 100° to 400° C., relatively low olefin level, relatively high cyclopentadiene or dicyclopentadiene level, and relatively high norbornene level to produce mostly the tetracyclododecene.
Claim 11
Dependent Claim
18 words
Process of claim 9 which includes the step of recycling a portion of the norbornene to the reactor.
Claim 12
Dependent Claim
32 words
Process of claim 6 which includes step of recycling a portion of the norbornene to the reactor, the quantity of recycled norbornene being sufficient to maintain the process on a continuous basis.
Claim 13
Dependent Claim
19 words
Process of claim 11 wherein the reaction is carried out at 240° to 280° C. and about 2000 psi.
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) | 1985-03-15 | 1985-09-14 | 1986-03-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-15 | 1989-09-14 | 1990-03-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-15 | 1993-09-14 | 1994-03-16 | $7700.00 | Window Closed / Lapsed |