GB690709A - New esters of acrylic and methacrylic acids - Google Patents
New esters of acrylic and methacrylic acidsInfo
- Publication number
- GB690709A GB690709A GB1000950A GB1000950A GB690709A GB 690709 A GB690709 A GB 690709A GB 1000950 A GB1000950 A GB 1000950A GB 1000950 A GB1000950 A GB 1000950A GB 690709 A GB690709 A GB 690709A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycerol
- acetals
- isomeric
- sodium
- reacted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises esters of acrylic or methacrylic acid and a 4-methylol-dioxolane or derivative thereof of the general formula <FORM:0690709/IV (b)/1> in which R is hydrogen or a methyl group and R1 and R11 represent hydrogen or an alkyl or aryl group. The 4-methylol-dioxolanes may be obtained by the interaction of glycerol and an aldehyde or ketone, e.g. formaldehyde, acetaldehyde, acetone, benzaldehyde or benzophenone whereby a mixture of the isomeric 4 - methylol - dioxolane and 1,3 - methylidene glycerol is obtained. This mixture may be esterified with acrylic or methacrylic acid or a functional derivative thereof, and the ester purified by distillation in the presence of a polymerization inhibitor such as finely-divided copper, hydroquinone or quinone. The unreacted acetal may be removed at any stage by washing the mixture with brine. Examples are given in which the isomeric acetals from glycerol and formaldehyde are esterified by reaction with (1) methacrylic acid in the presence of sulphuric acid, copper powder and benzene; (2) methacrylic acid chloride in the presence of pyridine; (3) methyl methacrylate in the presence of sodium; (4) the isomeric acetals from glycerol and acetaldehyde are reacted with methyl methacrylate in the presence of sodium; (5) 1,2-isopropylidene glycerol is reacted with methyl methacrylate in the presence of sodium; (6) the acetals from glycerol and benzaldehyde are reacted with methyl methacrylate in the presence of sodium; and (7) the ketal from glycerol and acetone is reacted with ethyl acrylate in the presence of sodium. The Specification describes also the preparation of the isomeric acetals from glycerol and formaldehyde; the isomeric acetals from glycerol and acetaldehyde; 1,2-isopropylidene glycerol; and the isomeric acetals from glycerol and benzaldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1000950A GB690709A (en) | 1950-04-24 | 1950-04-24 | New esters of acrylic and methacrylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1000950A GB690709A (en) | 1950-04-24 | 1950-04-24 | New esters of acrylic and methacrylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB690709A true GB690709A (en) | 1953-04-29 |
Family
ID=9959715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1000950A Expired GB690709A (en) | 1950-04-24 | 1950-04-24 | New esters of acrylic and methacrylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB690709A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102016201660A1 (en) | 2016-02-03 | 2017-08-03 | Evonik Röhm Gmbh | Process for the preparation of monomers from isomer mixtures |
-
1950
- 1950-04-24 GB GB1000950A patent/GB690709A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102016201660A1 (en) | 2016-02-03 | 2017-08-03 | Evonik Röhm Gmbh | Process for the preparation of monomers from isomer mixtures |
| WO2017134002A1 (en) | 2016-02-03 | 2017-08-10 | Evonik Röhm Gmbh | Method for producing monomers from isomeric mixtures |
| CN108602793A (en) * | 2016-02-03 | 2018-09-28 | 赢创罗姆有限公司 | The method that monomer is prepared by isomer mixture |
| US20190031638A1 (en) * | 2016-02-03 | 2019-01-31 | Evonik Röhm Gmbh | Method for producing monomers from isomeric mixtures |
| US10676454B2 (en) | 2016-02-03 | 2020-06-09 | Evonik Operations Gmbh | Method for producing monomers from isomeric mixtures |
| TWI731927B (en) * | 2016-02-03 | 2021-07-01 | 德商贏創運營有限公司 | Process for producing monomers from isomer mixtures |
| CN108602793B (en) * | 2016-02-03 | 2021-08-06 | 赢创运营有限公司 | Method for producing monomers from isomer mixtures |
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