ATE767T1 - PROCESS FOR THE PREPARATION OF N-VINYL-N-ALKYL CARBONIC ACID AMIDES. - Google Patents
PROCESS FOR THE PREPARATION OF N-VINYL-N-ALKYL CARBONIC ACID AMIDES.Info
- Publication number
- ATE767T1 ATE767T1 AT80102538T AT80102538T ATE767T1 AT E767 T1 ATE767 T1 AT E767T1 AT 80102538 T AT80102538 T AT 80102538T AT 80102538 T AT80102538 T AT 80102538T AT E767 T1 ATE767 T1 AT E767T1
- Authority
- AT
- Austria
- Prior art keywords
- acid amides
- carboxylic acid
- vinyl
- stage
- alkyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
N-Vinyl-N-alkyl-carboxylic acid amides are prepared, starting from N-ethyl-carboxylic acid amides, in a 3-stage process consisting of the following stages: (a) anodic alkoxylation of the N-ethyl-carboxylic acid amides to give N- alpha -alkoxyethyl-carboxylic acid amides; (b) alkylation of these N- alpha -alkoxyethyl-carboxylic acid amides with an alkyl halide or dialkyl sulfate in an alkaline medium to give N- alpha -alkoxyethyl-N-alkyl-carboxylic acid amides; and (c) splitting off of alcohol from the products of stage (b) by heating to temperatures between about 60 DEG and about 350 DEG C. Instead of stages (b) and (c), it is also possible to carry out the following stages after stage (a): (b1) splitting off of alcohol from the N- alpha -alkoxyethylcarboxylic acid amides obtained in stage (a) by heating to temperatures of about 60 DEG to about 600 DEG C., to give N-vinyl-carboxylic acid amides; and (c1) alkylation of these N-vinyl-carboxylic acid amides by reaction with an alkylating agent of the same type as in stage (b) in an alkaline medium. The N-vinyl-N-alkyl-carboxylic acid amides obtained by the process are valuable intermediate products, in particular for the manufacture of homopolymers and copolymers with interesting properties.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792919755 DE2919755A1 (en) | 1979-05-16 | 1979-05-16 | METHOD FOR PRODUCING N-VINYL-N-ALKYL-CARBONIC ACID AMIDES |
EP80102538A EP0019225B1 (en) | 1979-05-16 | 1980-05-08 | Process for the preparation of n-vinyl-n-alkyl carboxylic acid amides |
Publications (1)
Publication Number | Publication Date |
---|---|
ATE767T1 true ATE767T1 (en) | 1982-04-15 |
Family
ID=6070872
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT80102538T ATE767T1 (en) | 1979-05-16 | 1980-05-08 | PROCESS FOR THE PREPARATION OF N-VINYL-N-ALKYL CARBONIC ACID AMIDES. |
Country Status (7)
Country | Link |
---|---|
US (1) | US4322271A (en) |
EP (1) | EP0019225B1 (en) |
JP (1) | JPS55153754A (en) |
AT (1) | ATE767T1 (en) |
AU (1) | AU5843780A (en) |
CA (1) | CA1128066A (en) |
DE (2) | DE2919755A1 (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4459411A (en) * | 1982-09-13 | 1984-07-10 | The Dow Chemical Company | Preparation of unsaturated heterocyclic carbonyl-containing compounds |
US4567300A (en) * | 1984-01-14 | 1986-01-28 | Mitsubishi Chemical Industries Limited | Process for producing N-substituted formamides |
US4554377A (en) * | 1984-07-16 | 1985-11-19 | Celanese Corporation | Production of N-vinyl carboxylic acid amides |
US4973751A (en) * | 1985-03-02 | 1990-11-27 | Basf Aktiengesellschaft | Preparation of unsaturated compounds by elimination reaction |
DE3521764A1 (en) * | 1985-06-19 | 1987-01-08 | Basf Ag | METHOD FOR PRODUCING N-ALKENYLCARBONIC ACID AMIDES |
US5144074A (en) * | 1988-02-24 | 1992-09-01 | Air Products And Chemicals, Inc. | Process for the synthesis of carboxamides |
US5136094A (en) * | 1988-03-10 | 1992-08-04 | Air Products And Chemicals, Inc. | Process for the synthesis of secondary formamides |
US5059713A (en) * | 1988-06-27 | 1991-10-22 | Air Products And Chemicals, Inc. | Process for the preparation of n-vinyl amides |
US4942259A (en) * | 1988-06-27 | 1990-07-17 | Air Products And Chemicals, Inc. | Process for preparing n-vinyl amides |
US4906777A (en) * | 1988-10-19 | 1990-03-06 | Air Products And Chemicals, Inc. | Synthesis of ethylidene bis-formamide using formic acid |
US4968841A (en) * | 1989-11-14 | 1990-11-06 | Air Products And Chemicals, Inc. | Synthesis of ethylidene bisformamide from vinyl acetate |
US5023375A (en) * | 1990-01-17 | 1991-06-11 | Air Products And Chemicals, Inc. | Process for the synthesis of amides from vinyl acetate |
US5118846A (en) * | 1990-04-27 | 1992-06-02 | The Standard Oil Company | Synthesis of N-disubstituted amides by reaction of amides with certain organic hydroxyl compounds |
TW325471B (en) * | 1994-08-31 | 1998-01-21 | Shinetsu Sakusan Vinyl Kk | Method for the preparation of an n-vinyl compound |
JP3571795B2 (en) * | 1995-04-18 | 2004-09-29 | 株式会社日本触媒 | Catalyst for gas-phase intramolecular dealcoholation reaction of N- (1-alkyloxyalkyl) carbamates and method for producing N-vinyl carbamates |
US20220112155A1 (en) * | 2018-12-27 | 2022-04-14 | Showa Denko K.K. | Composition for producing n-vinyl carboxylic acid amide |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1445737A1 (en) * | 1963-07-20 | 1969-03-13 | Hoechst Ag | Process for the production of N-vinyl compounds |
US3193483A (en) * | 1964-01-14 | 1965-07-06 | Monsanto Co | Electrolysis of acrylamides |
DE1235893B (en) * | 1964-12-28 | 1967-03-09 | Hoechst Ag | Process for the preparation of N-vinyl-N-alkyl-formamides |
DE1545798C3 (en) * | 1965-03-20 | 1975-11-20 | Hoechst Ag, 6000 Frankfurt | Process for the production of N-vinyl compounds |
US3534099A (en) * | 1967-05-25 | 1970-10-13 | Gulf Research Development Co | Process for making n - substituted and n,n-substituted carboxylic acid amides |
FR2081393B1 (en) | 1969-12-23 | 1974-08-23 | Pharmacia Ab | |
DE2113338C3 (en) * | 1971-03-19 | 1978-08-24 | Hoechst Ag, 6000 Frankfurt | Process for the alkoxylation of carboxamides alkylated on the nitrogen |
DE2336976A1 (en) * | 1973-07-20 | 1975-02-13 | Hoechst Ag | PROCESS FOR THE PRODUCTION OF N- (ALPHAALCOXYAETHYL) CARBONIC ACID AMIDES |
NL7600544A (en) * | 1975-01-25 | 1976-07-27 | Hoechst Ag | PROCESS FOR THE PREPARATION OF N- (GAMMA-ALKOXY-ETHYL) -CARBONIC ACID AMIDES. |
DE2539767C2 (en) | 1975-09-06 | 1982-06-16 | Hoechst Ag, 6000 Frankfurt | Process for the preparation of N - (α-alkoxyethyl) carboxamides |
US4149941A (en) * | 1975-09-06 | 1979-04-17 | Hoechst Aktiengesellschaft | Process for preparing fungicidal monoalkoxy and dialkoxy N-substituted cyclic amines |
US4138408A (en) * | 1975-12-20 | 1979-02-06 | Hoechst Aktiengesellschaft | ω-Alkoxy derivatives of lactams and process for their manufacture |
-
1979
- 1979-05-16 DE DE19792919755 patent/DE2919755A1/en not_active Withdrawn
-
1980
- 1980-05-08 DE DE8080102538T patent/DE3060247D1/en not_active Expired
- 1980-05-08 EP EP80102538A patent/EP0019225B1/en not_active Expired
- 1980-05-08 AT AT80102538T patent/ATE767T1/en not_active IP Right Cessation
- 1980-05-14 US US06/149,742 patent/US4322271A/en not_active Expired - Lifetime
- 1980-05-15 JP JP6347080A patent/JPS55153754A/en active Pending
- 1980-05-15 AU AU58437/80A patent/AU5843780A/en not_active Abandoned
- 1980-05-15 CA CA351,989A patent/CA1128066A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
EP0019225A1 (en) | 1980-11-26 |
JPS55153754A (en) | 1980-11-29 |
CA1128066A (en) | 1982-07-20 |
DE2919755A1 (en) | 1980-11-27 |
US4322271A (en) | 1982-03-30 |
DE3060247D1 (en) | 1982-04-29 |
AU5843780A (en) | 1980-11-20 |
EP0019225B1 (en) | 1982-03-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
REN | Ceased due to non-payment of the annual fee |