GB869829A - Preparation of vinyl esters - Google Patents

Preparation of vinyl esters

Info

Publication number
GB869829A
GB869829A GB26453/57A GB2645357A GB869829A GB 869829 A GB869829 A GB 869829A GB 26453/57 A GB26453/57 A GB 26453/57A GB 2645357 A GB2645357 A GB 2645357A GB 869829 A GB869829 A GB 869829A
Authority
GB
United Kingdom
Prior art keywords
vinyl
reaction
vinyl ester
vapour
product
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
GB26453/57A
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.)
Airco Inc
Original Assignee
Air Reduction Co Inc
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 Air Reduction Co Inc filed Critical Air Reduction Co Inc
Publication of GB869829A publication Critical patent/GB869829A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C07C69/01—Vinyl esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C07C69/15—Vinyl acetate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Vinyl esters are prepared by a vinyl interchange reaction which comprises reacting with heat a carboxylic acid together with a vinyl ester reactant in the presence of a vinyl interchange catalyst to form a reaction product containing the corresponding vinyl ester of the carboxylic acid and the by-product acid of the vinyl ester reactant, removing the by-product acid from the reaction medium and continuing the vinyl interchange reaction until substantially complete. The by-product acid can be removed by entrainment in the vapour of the vinyl ester reactant, for example by passing the said vapour through the reaction mixture or by rapidly distilling the said vapour from the reaction mixture while adding fresh vinyl ester to maintain the correct proportions. The reaction medium may be passed downwardly through a heated bubble plate reaction column and the vinyl ester vapour passed upwardly through the column. The by-product acid is then separated from the vinyl ester vapour, e.g. by distillation, and the ester is recycled to the column. The reaction product is neutralized and stripped of vinyl ester reactant, and purified by distillation. The product may be further purified by dissolving in a hydrocarbon solvent such as pentane, hexane or heptane and liming the solution. The vinyl ester may be further purified by contacting with one or more absorbents comprising magnesium oxide, magnesium silicate and activated carbon. Mercury salt-strong acid catalysts are most effective in the process, using, e.g. mercuric oxide, acetate or stearate with sulphuric, phosphoric, p-toluene sulphonic or trifluoroacetic acid. Examples describe the preparation of divinyl sebacate, vinyl benzoate, methyl vinyl phthalate, vinyl cyclohexane carboxylate, divinyl adipate, vinyl toluate, vinyl stearatepalmitate, methyl vinyl succinate, vinyl pelargonate, and vinyl oleate. Specification 869,828 is referred to.
GB26453/57A 1956-08-27 1957-08-21 Preparation of vinyl esters Expired GB869829A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US869829XA 1956-08-27 1956-08-27

Publications (1)

Publication Number Publication Date
GB869829A true GB869829A (en) 1961-06-07

Family

ID=22202121

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26453/57A Expired GB869829A (en) 1956-08-27 1957-08-21 Preparation of vinyl esters

Country Status (1)

Country Link
GB (1) GB869829A (en)

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