US4609755A
Expired / Lapsed
US
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Synthesis of vinyl esters
Assignee: Ciba Specialty Chemicals Water Treatments Ltd
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Filing: 1985-04-15
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Granted: 1986-09-02
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Expires: 2005-04-15
Abstract
Abstract An ester interchange process, preferably for the formation of vinyl higher esters from methyl acrylate or methacrylate, is conducted in the presence of a novel alcoholate of the formula [M.sup.1 (OR.sup.4).sub.2-a R.sub.a.sup.6 ].sub.x [M.sup.2 (OR 4 ) n-b R b 6 ] y I wherein M 1 is selected from Mg, Ca and Ba M 2 is selected from Ti, Zr and Al n is 3 or 4 and is the valency of M 2 a is a number from 0 to 1.5 b is a number from 0 to 0.75n x+Y=1 and each is a number from 0.005 to 0.995 and is such that the compound is liquid at 30°0 C. R 4 is selected from alkyl having at least 4 carbon atoms, cycloalkyl having at least 4 carbon atoms and aminoalkyl, and each group R 6 is individually selected from C 1-3 alkoxy and blocking groups that are substantially less reactive in the ester interchange reaction than the groups OR 4 .
Inventors
- 👤 David Farrar
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 01:11
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/003
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
229 words
A process in which a compound R 3 COOR 4 is made by ester interchange with a compound R 3 COOR 1 in the presence of an alcoholate derived from an alcohol R 4 OH and optionally in the presence also of the alcohol R 4 OH, wherein R 1 is C 1-3 alkyl, R 3 is CH 2 ═CH-- or CH 2 ═C(CH 3 ) and R 4 is selected from alkyl having at least 4 carbon atoms, cycloalkyl having at least 4 carbon atoms and aminoalkyl, characterised in that the alcoholate is present as a solution in the reaction mixture and has the empirical formula [M.sup.1 (OR.sup.4).sub.2-a R.sub.a.sup.7 ].sub.x [M.sup.2 (OR.sup.4).sub.n-b R.sub.b.sup.7 ].sub.y I wherein M 1 is selected from Mg, Ca and Ba M 2 is selected from Ti, Zr and Al n is 3 or 4 and is the valency of M 2 a is a number from 0 to 1.5 b is a number from 0 to 0.75n x+y=1 and each is a number from 0.005 to 0.995 and is such that the compound is liquid at 30° C. R 4 is as defined above and each group R 7 is individually selected from (a) C 1-3 alkoxy groups and (b) C 8-30 alkyl or alkoxy blocking groups that are substantially less reactive in the ester interchange reaction than the groups OR 4 .
Claim 2
Dependent Claim
229 words
A process in which a compound R 3 COOR 4 is made by ester interchange with a compound R 3 COOR 1 in the presence of an alcoholate derived from an alcohol R 4 OH and optionally in the presence also of the alcohol R 4 OH, wherein R 1 is C 1-3 alkyl, R 3 is CH 2 ═CH-- or CH 2 ═C(CH 3 ) and R 4 is selected from alkyl having at least 4 carbon atoms, cycloalkyl having at least 4 carbon atoms and aminoalkyl, characterised in that the alcoholate is present as a solution in the reaction mixture and has the empirical formula [M.sup.1 (OR.sup.4).sub.2-a R.sub.a.sup.7 ].sub.x [M.sup.2 (OR.sup.4).sub.n-b R.sub.b.sup.7 ].sub.y I wherein M 1 is selected from Mg, Ca and Ba M 2 is selected from Ti, Zr and Al n is 3 or 4 and is the valency of M 2 a is a number from 0 to 1.5 b is a number from 0 to 0.75n x+y=1 and each is a number from 0.005 to 0.995 and is such that the compound is liquid at 30° C. R 4 is as defined above and each group R 7 is individually selected from (a) C 1-3 alkoxy groups and (b) C 8-30 alkyl or alkoxy blocking groups that are substantially less reactive in the ester interchange reaction than the groups OR 4 .
Claim 3
Dependent Claim
24 words
A process according to claim 1 conducted in the presence of the alcohol R 4 OH and wherein the alcoholate serves as a catalyst.
Claim 4
Dependent Claim
56 words
A process according to claim 1 wherein R 3 is CH 2 ═CH-- or CH 2 ═C(CH 3 )--, the process is conducted in the absence of reactive alcohol and the metal alcoholate provides the groups OR 4 that are utilised in forming the desired ester and reacts with the compound R 3 COOR 1 .
Claim 5
Dependent Claim
103 words
A process according to claim 1 wherein R 3 is CH 2 ═CH-- or CH 2 ═C(CH 3 )--, the process is conducted in the absence of reactive alcohol and the metal alcoholate provides the groups OR 4 that are utilised in forming the desired ester and reacts with the compound R 3 COOR 1 and the metal alcoholate formed in the reaction mixture is separated from the reaction mixture and is reacted with excess alcohol R 4 OH in the substantial absence of ester R 3 COOR 1 and the resultant metal alcoholate of formula I is recycled to the reaction mixture.
Claim 6
Dependent Claim
28 words
A process according to claim 4 in which the separation of the metal alcoholate is by evaporation of the esters in the reaction mixture from the metal alcoholate.
Claim 7
Dependent Claim
14 words
A process according to claim 1 conducted in the absence of an inert solvent.
Claim 8
Dependent Claim
24 words
A process according to claim 1 in which at the start of the process, a and b in the metal alcoholate are both zero.
Claim 9
Dependent Claim
21 words
A process according to claim 1 in which M 1 is Mg and M 2 is selected from Ti and Zr.
Claim 10
Dependent Claim
17 words
A process according to claim 1 in which x is 0.01 to 0.5, preferably 0.02 to 0.2.
Claim 11
Dependent Claim
53 words
A process according to claim 1 in which R 4 is selected from C 5-30 alkyl, C 5-8 cycloalkyl and dialkylaminoalkyl of the formula (R 5 ) 2 N--C n H 2n wherein n is 2 or 3 and the groups R 5 are the same or different and are C 1-3 alkyl.
References Cited (Backward Citations)
US4333881A
Cited
US4543422A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-09-01 | 1990-03-03 | 1990-09-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-09-01 | 1994-03-03 | 1994-09-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-09-01 | 1998-03-03 | 1998-09-02 | $7700.00 | Window Closed / Lapsed |