US3879483A
Expired / Lapsed
US
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Process for the manufacture of vinylcycloalkanes
Assignee: Solvay SA
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Filing: 1974-03-26
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Granted: 1975-04-22
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Expires: 1994-03-26
Abstract
Abstract Vinylcycloalkanes of the formula R-CH CH2 wherein R is a cycloaliphatic radical with 5 or 6 carbon atoms which can be substituted by substituents selected from the group consisting of alkyl groups containing 1 to 6 carbon atoms and saturated chains containing 1 to 6 carbon atoms and a hetero-atom selected from the group consisting of sulfur, oxygen and nitrogen are prepared by reacting vinyl chloride and an organometallic compound of the formula (R)n-M. The radical R of the organometallic compound is defined as above, M is a lithium atom, a cadmium atom or a magnesium-halogen group and n is equal to 1 when M is lithium or the magnesium-halogen group and is equal to 2 when M is cadmium. A catalyst is used which consists of a metal from Group VIII of the Periodic Table or a compound of a metal from Group VIII of the Periodic Table and at least one compound of an element from Groups VA and VIA of the Periodic Table of elements which is complexed with the metal from Group VIII or the compound of a metal from Group VIII.
Inventors
- 👤 Noel Vanlautem
- 👤 Alain Donzel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 12:09
CPC Classifications
C; C07; C07C; C07C1/00; C07C1/32; C07C1/325; C07C1/326; C07C2527/00; C07C2527/06; C07C2527/128; C07C2531/00; C07C2531/16; C07C2531/24; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
187 words
A PROCESS FOR THE MANUFACTURE OF VINYLCYCLOALKANES OF THE FORMULA R-CH=CH2, WHEREIN R REPRESENTS A CYCLOALIPHATIC RADICAL WITH 5 OR 6 CARBON ATOMS WHICH CAN BE SUBSTITUTED BY SUBSTITUENTS SELECTED FROM THE GROUP CONSISTING OF ALKYL GROUPS CONTAINING 1 TO 6 CARBON ATOMS AND SATURATED CHAINS CONTAINING 1 TO 6 CARBON ATOMS AND A HETERO-ATOM SELECTED FROM THE GROUP CONSISTING OF SULFUR, OXYGEN AND NITROGEN, THE PROCESS COMPRISING REACTING VINYL CHLORIDE WITH AN ORGANOMETALLIC COMPOUND (R)N-M, WHEREIN R IS DEFINED AS ABOVE, M REPRESENTS A LITHIUM ATOM, A CADMIUM ATOM OR A MAGNESIUMHALOGEN GROUP, AND N IS EQUAL TO 1 WHEN M REPRESENTS LITHIUM OR THE MAGNESIUM-HALOGEN GROUP AND EQUAL TO 2 WHEN M REPRESENTS CADMIUM, IN THE PRESENCE OF A CATALYST CONSISTING OF A METAL FROM GROUP VIII OF THE PERIODIC TABLE OR A COMPOUND OF A METAL FROM GROUP VIII OF THE PERIODIC TABLE AND AT LEAST ONE COMPOUND OF AN ELEMENT SELECTED FROM THE GROUP CONSISTING OF GROUP VA AND GROUP VIA OF THE PERIODIC TABLE OF THE ELEMENTS WHICH IS COMPLEXED WITH THE METAL OR THE COMPOUND OF A METAL FROM GROUP VIII.
Claim 2
Dependent Claim
187 words
A PROCESS FOR THE MANUFACTURE OF VINYLCYCLOALKANES OF THE FORMULA R-CH=CH2, WHEREIN R REPRESENTS A CYCLOALIPHATIC RADICAL WITH 5 OR 6 CARBON ATOMS WHICH CAN BE SUBSTITUTED BY SUBSTITUENTS SELECTED FROM THE GROUP CONSISTING OF ALKYL GROUPS CONTAINING 1 TO 6 CARBON ATOMS AND SATURATED CHAINS CONTAINING 1 TO 6 CARBON ATOMS AND A HETERO-ATOM SELECTED FROM THE GROUP CONSISTING OF SULFUR, OXYGEN AND NITROGEN, THE PROCESS COMPRISING REACTING VINYL CHLORIDE WITH AN ORGANOMETALLIC COMPOUND (R)N-M, WHEREIN R IS DEFINED AS ABOVE, M REPRESENTS A LITHIUM ATOM, A CADMIUM ATOM OR A MAGNESIUMHALOGEN GROUP, AND N IS EQUAL TO 1 WHEN M REPRESENTS LITHIUM OR THE MAGNESIUM-HALOGEN GROUP AND EQUAL TO 2 WHEN M REPRESENTS CADMIUM, IN THE PRESENCE OF A CATALYST CONSISTING OF A METAL FROM GROUP VIII OF THE PERIODIC TABLE OR A COMPOUND OF A METAL FROM GROUP VIII OF THE PERIODIC TABLE AND AT LEAST ONE COMPOUND OF AN ELEMENT SELECTED FROM THE GROUP CONSISTING OF GROUP VA AND GROUP VIA OF THE PERIODIC TABLE OF THE ELEMENTS WHICH IS COMPLEXED WITH THE METAL OR THE COMPOUND OF A METAL FROM GROUP VIII.
Claim 3
Dependent Claim
188 words
A process for the manufacture of vinylcycloalkanes of the formula R-CH CH2, wherein R represents a cycloaliphatic radical with 5 or 6 carbon atoms which can be substituted by substituents selected from the group consisting of alkyl groups containing 1 to 6 carbon atoms and saturated chains containing 1 to 6 carbon atoms and a hetero-atom selected from the group consisting of sulfur, oxygen and nitrogen, the process comprising reacting vinyl chloride with an organometallic compound (R)n-M, wherein R is defined as above, M represents a lithium atom, a cadmium atom or a magnesium-halogen group, and n is equal to 1 when M represents lithium or the magnesium-halogen group and equal to 2 when M represents cadmium, in the presence of a catalyst consisting of a metal from Group VIII of the Periodic Table or a compound of a metal from Group VIII of the Periodic Table and at least one compound of an element selected from the group consisting of Group VA and Group VIA of the Periodic Table of the Elements which is complexed with the metal or the compoUnd of a metal from Group VIII.
Claim 4
Dependent Claim
188 words
A process for the manufacture of vinylcycloalkanes of the formula R-CH CH2, wherein R represents a cycloaliphatic radical with 5 or 6 carbon atoms which can be substituted by substituents selected from the group consisting of alkyl groups containing 1 to 6 carbon atoms and saturated chains containing 1 to 6 carbon atoms and a hetero-atom selected from the group consisting of sulfur, oxygen and nitrogen, the process comprising reacting vinyl chloride with an organometallic compound (R)n-M, wherein R is defined as above, M represents a lithium atom, a cadmium atom or a magnesium-halogen group, and n is equal to 1 when M represents lithium or the magnesium-halogen group and equal to 2 when M represents cadmium, in the presence of a catalyst consisting of a metal from Group VIII of the Periodic Table or a compound of a metal from Group VIII of the Periodic Table and at least one compound of an element selected from the group consisting of Group VA and Group VIA of the Periodic Table of the Elements which is complexed with the metal or the compoUnd of a metal from Group VIII.
Claim 5
Dependent Claim
12 words
The process according to claim 1 wherein R is a cyclohexyl radical.
Claim 6
Dependent Claim
33 words
The process according to claim 1 wherein a compound of a metal from Group VIII is used in the catalyst and said compound of a metal from Group VIII is a metal salt.
Claim 7
Dependent Claim
14 words
The process according to claim 3 wherein the metal salt is a metal chloride.
Claim 8
Dependent Claim
13 words
The process according to claim 4 wherein the metal chloride is nickel chloride.
Claim 9
Dependent Claim
13 words
The process according to claim 4 wherein the metal chloride is ferric chloride.
Claim 10
Dependent Claim
20 words
The process according to claim 1 wherein an organic compound of an element from Groups VA and VIA is used.
Claim 11
Dependent Claim
24 words
The process according to claim 7 wherein the organic compound of an element from Groups VA and VIA is an organic compound of phosphorus.
Claim 12
Dependent Claim
16 words
The process according to claim 8 wherein the organic compound of phosphorus is 1,2 -bis-(diphenylphosphino) -ethane.
Claim 13
Dependent Claim
24 words
The process according to claim 7 wherein the organic compound of an element from Groups VA and VIA is an organic compound of oxygen.
Claim 14
Dependent Claim
14 words
The process according to claim 10 wherein the organic compound of oxygen is tetrahydrofuran.
Claim 15
Dependent Claim
17 words
The process according to claim 1 wherein the organometallic compound (R)n-M is a halogenated compound of magnesium.
Claim 16
Dependent Claim
15 words
The process according to claim 12 wherein the organometallic compound (R)n-M is a cyclohexylmagnesium halide.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-04-21 | 1978-10-21 | 1979-04-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-04-21 | 1982-10-21 | 1983-04-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-04-21 | 1986-10-21 | 1987-04-22 | $7700.00 | Window Closed / Lapsed |