GB569404A - Manufacture of new esters and of compositions containing them - Google Patents

Manufacture of new esters and of compositions containing them

Info

Publication number
GB569404A
GB569404A GB242/42A GB24242A GB569404A GB 569404 A GB569404 A GB 569404A GB 242/42 A GB242/42 A GB 242/42A GB 24242 A GB24242 A GB 24242A GB 569404 A GB569404 A GB 569404A
Authority
GB
United Kingdom
Prior art keywords
oic
furyl
acid
cyano
methyl
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
GB242/42A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB569404A publication Critical patent/GB569404A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22Esters 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
    • C07C69/33Esters 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 hydroxy compounds having more than three hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Complex esters of a polyhydric alcohol with an a -g -diolefinic carboxylic acid and another carboxylic acid not containing an additional functional group (such as -OH, NH2 or NH) are made by reacting the polyhydric alcohol with the acids or hydrolyzable derivatives thereof in any order. The polyhydric alcohol may be glycerol, hexamethylene glycol, pentaerythritol, methyl trimethylol methane, erythritol, 1 - 4 - di-(b -hydroxyethyl) benzene, decamethylene glycol, diethylene glycol, sorbitol, cyclohexyl 1-2-dicarbinol or the like. The monofunctional acids include the acids of linseed, soya, coconut, perilla, oiticica, corn and cottonseed oils, lauric, p-toluic, quinolinic, oleic, stearic and phenoxy acetic acids. Suitable a -g -diolefinic acids are hexadien-2-4-oic, 2-methyl hexadien-2-4-oic, 4-ethyloctadien-2-4-oic, 5-9-dimethyldecatrien-2-4-8-oic, octatrien - 2 - 4 - 8 - oic, 7 - phenylhaptatrien - 2-4-6-oic, D -1-3-cyclopentadien carboxylic, 5-cyclohexylpentadien-2-4-oic, 3-(D -1-3-cyclohexadienyl) propenoic, octatrien-2-4-6-carboxylic, 2-phenylhexadien-2-4-oic, 4-methylheptadien-2-4-oic, 5-9-dimethyl decatrien-2-4-8-oic, b -ionylidene acetic, 3-5-dimethyl hexadien-2-4-oic, 2-furyl hexadien-2-4-oic, 5-(2-furyl) pentadien-2-4-oic, cinnamalacetic, a -methyl cinnamalacetic, a -cyano-cinnamal-acetic, 2-5-diphenyl pentadien-2-4-oic, 2-furyl-5-phenyl pentadien-2-4-oic, 7-phenyl heptatrien-2-4-6 carboxylic acid-4, 5-methyl-5-phenyl pentadien-2-4-oic, 5-5-diphenyl pentadien-2-4-oic, p-tolyl pentadien-2-4-oic, 2-cyclohexyl-5-phenyl-pentadien-2-4-oic, 2-cyclopentadienyl-5-phenyl-pentadien-2-4-oic, 2-cyano-hexadien-2-4-oic, 2-cyano-5-9-dimethyl decatriene-2-4-8-oic, 2-cyano-3-6-dimethyl hexadien-2-4-oic, 2-4-dicyano-hexadien-2-4-oic, 2-methyl-4-cyano-hexadien-2-4-oic, 2-cyano-5-phenyl pentadien-2-4-oic, 2-cyano-octadien-2-4-oic, 2-cyano-4-methyl-7-phenyl-heptatriene-2-4-6-oic, 4-cyano-hexadien-2-4-oic, 2-cyano-5-cyclohexyl pentadien-2-4-oic, a -cyano-a -(b -ionylidene) acetic, b -(2-furyl) acrylic, a -methyl-b -(2-furyl) acrylic, a -cyano-b -(2-furyl) acrylic, a -b -di-(2-furyl) acrylic, a -phenyl-b -(2-furyl) acrylic, a -b -dimethyl-b -(2-furyl) acrylic, b -cyclohexyl-b -(2-furyl) acrylic, b -(3-furyl) acrylic, b -[2-(5-methylfuryl)] acrylic, and b -[2-(5-chlorofuryl)] acrylic acids, which are referred to as super-drying acids. In carrying out the esterifications, oxygen or substances yielding it should be excluded and consequently solvents such as aged turpentine or aged petroleum naphtha should not be used. A number of suitable solvents are listed. In the examples: (2) linseed oil is heated with glycerol and the product is then heated with hexadien-2-4-oic acid; (5) penta-erythritol is esterified with coconut oil acids and hexadien-2-4-oic acid; (6) an ester similar to that of example (2) is heated with linseed oil to form a modified ester; (10) linseed oil is heated with glycerol and the product is heated with b -(2-furyl) acrylic acid; (17) the penta-erythritol tri-ester of linseed oil acids is heated with glycerol di-ester of linseed oil acids and b -(2-furyl) acrylic acid; (18) a -methyl-b -(2-furyl) acrylic acid is esterified with glycerol di-ester of linseed oil acids; (19) glycerol dibenzoate is esterified with b -(2-furyl) acrylic acid; (25) linseed oil is heated with glycerol and the product is esterified with 2-cyano-hexadien-2-4-oic acid; (27) glycerol mono-ester of soya bean oil acids is esterified with 2-cyano-hexadien-2-4-oic acid; (28) and (29) di- and mono-glycerol esters of linseed oil acids are esterified with cinnamal acetic acid; (34) hexamethylene glycol, linseed oil acids and a -cyano-cinnamal-acetic acid are esterified together. Paints and varnishes.-The product of example (2), bodied by heating under nitrogen, is heated with a phenolic-modified ester gum; hydrated lime, litharge, the unbodied oil, and manganese resinate are added, and the mixture is again heated, and finally thinned with a hydrocarbon; a white and a black enamel are prepared from the same oil. The product of example (5) is mixed with a butyl acetate solution of nitrocellulose to form a lacquer. The product of example (10) is made into a black and a white enamel. The product of example (18) is made into a varnish by a method similar to that employed with the product of example (2). In examples (22) and (23) describe, the production of a varnish and an enamel from the product of example (10) in a similar manner. The product of example (25) is made into a varnish and an enamel similarly. The product of example (28) is made into an enamel base and a varnish, and the product of example (29) into an enamel. a -g -Diolefinic acids.-4-Ethyl-octadien-2-4-oic, octatrien-2-4-6-oic, 7-phenyl-heptatrien-2-4-6-oic, 5-cyclohexyl-pentadien-2-4-oic, 4-methyl-heptadien-2-4-oic, 5-9-dimethyl-decatrien-2-4-8-oic, 5-(2-furyl)-pentadien-2-4-oic, 5-5-diphenyl-pentadien-2-4-oic, 5-(p-tolyl)-pentadien-2-4-oic, and 4-cyano-hexadien 2-4-oic acids are made by condensing malonic ester with 2 - ethyl - hexanol, CH3.CH=CH-CH= CH.CHO, PhCH=CH-CH=CH-CHO, C6H11CH=CH-CHO, C2H5-CH=CMe.CHO, citral b - (2 - furyl) acrolein, Ph2C=CH.CHO, p-methyl cinnamic aldehyde, and a -cyano-crotonaldehyde respectively. 5-9-Dimethyl decatrien-2-4-8-oic acid is made by condensing citral with methyl acetate. D -1-3-Cyclopentadien carboxylic acid is made from cyclopentadiene, carbon dioxide and potassium. 3-(D -1-3-cyclohexadienyl) propenoic acid is made by condensing D -1-3-cyclohexadienal with malonic acid. Octatrien-2-4-6-carboxylic acid-4 is made by condensing crotonaldehyde with CH3-CH=CH-CHBr-COOEt in presence of zinc. 2-Phenyl-hexadien-2-4-oic acid is made by condensing crotonaldehyde with a -bromophenylacetic ester in presence of zinc. b -Ionylidene acetic acid is made by condensing b -ionone with bromacetic ester. 3-5-Dimethyl-hexadien-2-4-oic acid is made by condensing mesityloxide with bromoacetic ester in presence of zinc. 2-Furyl-hexadien-2-4-oic acid is made by condensing crotonaldehyde with a -bromo-(2-furylacetic) ester in presence of zinc. 2-5-Diphenylpentadien-2-4-oic acid is made by condensing cinnamic aldehyde with phenylacetic ester. 2-Furyl-5-phenyl-pentadien-2-4-oic acid is made by condensing cinnamic aldehyde with 2-furyl acetic ester. 7-Phenyl-heptatrien-2-4-6 carboxylic acid-4 is made by condensing cinnamic aldehyde with CH3-CH=CH-CH=CH-COOEt. 3-Methyl-5-phenyl-pentadien-2-4-oic acid is made by condensing benzalacetone with bromacetic ester. 2-Cyclohexyl-5-phenyl-pentadien-2-4-oic acid is made by condensing cinnamic aldehyde with cyclohexyl acetic ester. 2-Cyclopentadienyl-5-phenyl-pentadien-2-4-oic acid is made by the action of potassium on cinnamic aldehyde chloracetic acid, and cyclopentadiene. 2-Cyano-5-9-dimethyl-decatrien-2-4-8-oic and p 2-cyano-3-6-dimethyl-hexadien-2-4-oic acids are made by condensing citral and mesityl oxide respectively with cyanoacetic ester. 2-4-Dicyano-hexadien-2-4-oic and 2-methyl-4-cyano-hexadien-2-4-oic acids are made by reacting sodium cyanide with 2-cyano-4-chlorhexadien-2-4-oic and 2-methyl-4-chlorohexadien-2-4-oic acid respectively. 2-Cyano-5-phenyl-pentadien-2-4-oic, 2-cyano-octadien-2-4-oic and 2-cyano-4-methyl 7-phenyl-heptatrien-2-4-6-oic acids are made by condensing cyanoacetic ester with a -methyl cinnamic aldehyde, hexen-2-al-1, and Ph-CH=CH-CH=CMe-CHO respectively. 2-Cyano-5-cyclohexyl-pentadien-2-4-oic acid is made by condensing b -cyclohexyl acrolein with cyanoacetic ester. a -Cyano-a -(b -ionylidene) acetic acid is made by condensing b -ionone with bromoacetic ester. a -Methyl-b -(2-furyl) acrylic acid is made by reacting furfural with methyl propionate and sodium. a -b -di-(2-furyl) acrylic and a -phenyl-b -(2-furyl) acrylic acids are made by reacting furfural with 2-furylacetic ester and sodium and with phenylacetic acid re respectively. a -b -Dimethyl-b -(2-furyl) acrylic acid is made by reacting methyl furyl ketone with methyl-a -bromo-propionate and dehydration. b -Cyclohexyl-b -(2-furyl) acrylic acid is made by reacting cyclohexyl furyl ketone with methyl bromoacetate and dehydration. b -(3-furyl) acrylic, b -[2-(5-methylfuryl)] acrylic, and b -[2-(5-chlorfuryl)] acrylic acids are made by reacting 3-aldehydofuran, 5-methylfurfural, and 5-chlorfurfural respectively with acetic anhydride and sodium acetate.
GB242/42A 1940-12-30 1942-01-07 Manufacture of new esters and of compositions containing them Expired GB569404A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US569404XA 1940-12-30 1940-12-30

Publications (1)

Publication Number Publication Date
GB569404A true GB569404A (en) 1945-05-23

Family

ID=22007497

Family Applications (1)

Application Number Title Priority Date Filing Date
GB242/42A Expired GB569404A (en) 1940-12-30 1942-01-07 Manufacture of new esters and of compositions containing them

Country Status (1)

Country Link
GB (1) GB569404A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2912447A (en) * 1957-11-29 1959-11-10 Eastman Kodak Co Cyclic diol diester lubricants
US3239539A (en) * 1960-12-02 1966-03-08 Exxon Research Engineering Co Gem dimethylol alicyclic esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2912447A (en) * 1957-11-29 1959-11-10 Eastman Kodak Co Cyclic diol diester lubricants
US3239539A (en) * 1960-12-02 1966-03-08 Exxon Research Engineering Co Gem dimethylol alicyclic esters

Similar Documents

Publication Publication Date Title
US2350583A (en) Drying oils
US2188885A (en) Condensation product and method
GB569404A (en) Manufacture of new esters and of compositions containing them
Igbo et al. Utilisation of beniseed oil for the production of alkyd resin
US2464202A (en) Drying oil acid esters and process
US2188886A (en) Condensation product and method
US2188889A (en) Condensation product and method
GB1471611A (en) Liquid autoxidisable fatty acid esters
US1969709A (en) Siccative composition
US1942778A (en) Process of producing the same
US2552872A (en) Acylation with conjugated diene
GB1449010A (en) Autoxidisable film forming materials
GB859467A (en) Improvements in or relating to drying oils
US2381881A (en) Mixed esters
GB405826A (en) Improvements in or relating to the manufacture of paints, enamels and lacquers
GB916090A (en) Improvements in and relating to a process for the preparation of thixotropic gelled resins, products resulting therefrom, and compositions containing such products
GB405827A (en) Improvements in or relating to the manufacture of mixed esters of polyhydric alcohols and resins and coating compositions manufactured therefrom
GB306924A (en) Improvements in and relating to synthetic resins
US2286466A (en) Oil acid-modified polyhydric alcohol-polybasic acid resin
US2381887A (en) Mixed esters
GB1026878A (en) Aqueous surface coating compositions
GB425181A (en) Improvements in the manufacture and production of paints, lacquers and varnishes
GB547321A (en) Improvements in coating compositions and methods of making the same
US1979495A (en) Process foe the manufacture of
US1900734A (en) Benindttstrie aktiengesellschaft