US4665223A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of 1-alkoxyalkyl esters
Assignee: BP Chemicals Ltd
•
Filing: 1985-01-15
•
Granted: 1987-05-12
•
Expires: 2005-01-15
Abstract
Abstract A process for the production of 1-alkoxyalkyl esters comprises reacting an unsaturated ester with an alcohol in the presence of a Lewis base containing catalyst. The Lewis base containing catalyst is preferably (i) an amidine, or (ii) a Lewis base and an epoxide or (iii) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne. The process can be used to prepare, for example, 1-methoxyethyl acetate from vinyl acetate and methanol under mild conditions.
Inventors
- 👤 Michael J. Green
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:58
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/30; C07C67/31; C07C69/00; C07C69/02; C07C69/12; C07C69/14
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
150 words
A process for production of 1-alkoxyalkyl esters characterised in that the process comprises reacting an unsaturated ester of the formula ##STR11## wherein R is hydrogen, R' and R" are independently hydrogen, an --O 2 CR"' group, alkyl or an aryl hydrocarbyl radical and R"' is alkyl or an aryl hydrocarbyl group with an alcohol in the presence of an effective amount of a Lewis base containing catalyst, said Lewis base containing catalyst comprising one or more of the following: (1) an amidine (2) a Lewis base selected from the group consisting of amines, phosphines, arsines and stibines in the presence of an epoxide, and (3) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne, said activated alkene or alkyne having the formula ##STR12## where X is an electron withdrawing group, and where R 1 , R 2 and R 3 are monovalent hydrocarbyl groups or hydrogen.
Claim 2
Dependent Claim
150 words
A process for production of 1-alkoxyalkyl esters characterised in that the process comprises reacting an unsaturated ester of the formula ##STR11## wherein R is hydrogen, R' and R" are independently hydrogen, an --O 2 CR"' group, alkyl or an aryl hydrocarbyl radical and R"' is alkyl or an aryl hydrocarbyl group with an alcohol in the presence of an effective amount of a Lewis base containing catalyst, said Lewis base containing catalyst comprising one or more of the following: (1) an amidine (2) a Lewis base selected from the group consisting of amines, phosphines, arsines and stibines in the presence of an epoxide, and (3) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne, said activated alkene or alkyne having the formula ##STR12## where X is an electron withdrawing group, and where R 1 , R 2 and R 3 are monovalent hydrocarbyl groups or hydrogen.
Claim 3
Dependent Claim
18 words
A process as claimed in claim 1 characterised in that the Lewis base containing catalyst is an amidine.
Claim 4
Dependent Claim
15 words
A process as claimed in claim 2 characterised in that the amidine is a guanidine.
Claim 5
Dependent Claim
16 words
A process as claimed in claim 2 characterised in that the amidine is a cyclic amidine.
Claim 6
Dependent Claim
17 words
A process as claimed in claim 4 characterised in that the cyclic amidine is a cyclic guanidine.
Claim 7
Dependent Claim
42 words
A process as claimed in claim 4 characterised in that the cyclic amindine has an amidine group which forms part of a fused ring system containing 6 and 5 membered rings, or 6 and 7 membered rings or two six membered rings.
Claim 8
Dependent Claim
24 words
A process as claimed in claim 6 characterised in that the cyclic amidine is selected from the group consisting of 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene and 1,5,7-triazabicyclo[4.4.0]dec-5-ene.
Claim 9
Dependent Claim
22 words
A process as claimed in claim 1 characterised in that the Lewis base containing catalyst comprises a Lewis base and an epoxide.
Claim 10
Dependent Claim
16 words
A process as claimed in claim 8 characterised in that the Lewis base is an amine.
Claim 11
Dependent Claim
15 words
A process as claimed in claim 9 characterised in that the amine is an amidine.
Claim 12
Dependent Claim
15 words
A process as claimed in claim 9 characterised in that the amine is an alkylamine.
Claim 13
Dependent Claim
29 words
A process as claimed in claim 1 characterised in that the Lewis base containing catalyst comprises a trivalent organophosphorus compound in the presence of said activated alkene or alkyne.
Claim 14
Dependent Claim
28 words
A process as claimed in claim 12 characterised in that the trivalent organophosphorus compound is a mono-, di- or trialkyl phosphine or a mono-, di- or triaryl phosphine.
Claim 15
Dependent Claim
31 words
A process as claimed in claim 12 characterised in that the Lewis base catalyst is prepared by dissolving the trivalent organophosphorus compound and the activated alkene or alkyne in a solvent.
Claim 16
Dependent Claim
35 words
A process as claimed in claim 1 characterised in that X is an electron withdrawing group selected from --COOR, --COR, --CONH 2 , CON(R) 2 or --CN where R is an alkyl or aryl group.
Claim 17
Dependent Claim
21 words
A process as claimed in claim 1 characterised in that the Lewis base containing catalyst is supported on an inert solid.
Claim 18
Dependent Claim
115 words
A process for the production of 1-methoxyethyl acetate characterised in that the process comprises reacting vinyl acetate with methanol in the presence of an effective amount of a Lewis base containing catalyst, said Lewis base containing catalyst comprising one or more of the following: (1) an amidine, (2) a Lewis base selected from the group consisting of amines, phosphines, arsines and stibines in the presence of an epoxide, and (3) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne, said activated alkene or alkyne having the formula ##STR13## where X is an electron withdrawing group, and where R 1 , R 2 and R 3 are monovalent hydrocarbyl groups or hydrogen.
Claim 19
Dependent Claim
115 words
A process for the production of 1-methoxyethyl acetate characterised in that the process comprises reacting vinyl acetate with methanol in the presence of an effective amount of a Lewis base containing catalyst, said Lewis base containing catalyst comprising one or more of the following: (1) an amidine, (2) a Lewis base selected from the group consisting of amines, phosphines, arsines and stibines in the presence of an epoxide, and (3) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne, said activated alkene or alkyne having the formula ##STR13## where X is an electron withdrawing group, and where R 1 , R 2 and R 3 are monovalent hydrocarbyl groups or hydrogen.
Claim 20
Dependent Claim
115 words
A process for the production of 1-ethoxyethyl acetate characterised in that the process comprises reacting vinyl acetate with ethanol in the presence of an effective amount of a Lewis base containing catalyst, said Lewis base containing catalyst comprising one or more of the following: (1) an amidine, (2) a Lewis base selected from the group consisting of amines, phosphines, arsines and stibines in the presence of an epoxide, and (3) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne, said activated alkene or alkyne having the formula ##STR14## where X is an electron withdrawing group, and where R 1 , R 2 and R 3 are monovalent hydrocarbyl groups or hydrogen.
Claim 21
Dependent Claim
115 words
A process for the production of 1-ethoxyethyl acetate characterised in that the process comprises reacting vinyl acetate with ethanol in the presence of an effective amount of a Lewis base containing catalyst, said Lewis base containing catalyst comprising one or more of the following: (1) an amidine, (2) a Lewis base selected from the group consisting of amines, phosphines, arsines and stibines in the presence of an epoxide, and (3) a trivalent organophosphorus compound in the presence of an activated alkene or alkyne, said activated alkene or alkyne having the formula ##STR14## where X is an electron withdrawing group, and where R 1 , R 2 and R 3 are monovalent hydrocarbyl groups or hydrogen.
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) | 1990-05-11 | 1990-11-10 | 1991-05-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-11 | 1994-11-10 | 1995-05-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-11 | 1998-11-10 | 1999-05-12 | $7700.00 | Window Closed / Lapsed |