GB690709A - New esters of acrylic and methacrylic acids - Google Patents

New esters of acrylic and methacrylic acids

Info

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
Application number
GB1000950A
Inventor
Eric Ellery
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1000950A priority Critical patent/GB690709A/en
Publication of GB690709A publication Critical patent/GB690709A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10Heterocyclic 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
    • C07D317/14Heterocyclic 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
    • C07D317/18Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24Radicals 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.
GB1000950A 1950-04-24 1950-04-24 New esters of acrylic and methacrylic acids Expired GB690709A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (7)

* Cited by examiner, † Cited by third party
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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