GB923847A - Citric acid esters and method for their preparation - Google Patents

Citric acid esters and method for their preparation

Info

Publication number
GB923847A
GB923847A GB3749261A GB3749261A GB923847A GB 923847 A GB923847 A GB 923847A GB 3749261 A GB3749261 A GB 3749261A GB 3749261 A GB3749261 A GB 3749261A GB 923847 A GB923847 A GB 923847A
Authority
GB
United Kingdom
Prior art keywords
citric acid
acids
carbon atoms
varnishes
esters
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
GB3749261A
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.)
Joh A Benckiser GmbH
Original Assignee
Joh A Benckiser GmbH
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
Priority claimed from DEB60417A external-priority patent/DE1143502B/en
Application filed by Joh A Benckiser GmbH filed Critical Joh A Benckiser GmbH
Publication of GB923847A publication Critical patent/GB923847A/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
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • C07C69/704—Citric acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Citric acid esters of formula <FORM:0923847/IV(a)/1> in which R1 to R6 are alkyl groups with 1 to 18 carbon atoms and Y is the residue of an aliphatic saturated or unsaturated, or aromatic dicarboxylic acid, are used as plasticisers and prevent blocking in emulsion and/or suspension polymers, e.g. polyvinyl chloride, vinyl chloridevinyl acetate copolymer, polyvinylidene chloride, vinyl chloridevinylidene chloride copolymer, polyvinyl acetate, and butadiene-acrylonitrile, polyamides of, e.g. caprolactam or hexamethylene diamine and adipic acid, varnishes based on polymethane, chlororubber and chlororubber varnishes, rubber hydrochloride and rubber hydrochloride foils, regenerated cellulose products, and foils formed from polyvinyl chloride emulsion, used for the packing of foods, or edible oils and fats.ALSO:The invention comprises citric acid esters of formula <FORM:0923847/IV(a)/1> in which R1 to R6 are alkyl groups with 1 to 18 carbon atoms and Y is the residue of an aliphatic saturated or unsaturated, or aromatic dicarboxylic acid, which are prepared by reacting the t-hydroxyl group of citric acid acid esterified to the triester with alcohols having 1 to 18 carbon atoms, with dicarboxylic acid halides. Oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic and sebacic acids, fumaric, citraconic and itaconic acids, phthalic, isophthalic, and terephthalic acids are examples of the above dicarboxylic acids. Examples describe the preparation of bis-citric acid trimethyl, triethyl, tripropyl, tributyl, triisooctyl, trinonyl, tricyclohexyl esters with the above acids, by the reaction of di-carboxylic acid halide with citric acid triesters, esterified with alcohols of 1-18 groups, using the tert. alcohol group. The esters may be used as plasticisers in plastisols or organosols or nitro-cellulose varnishes, as dyeing auxiliaries in the textile industry or as anti-blocking agents in varnishes or vinyl polymers.ALSO:Citric acid esters of formula <FORM:0923847/IV(a)/1> in which R1 to R6 are alkyl groups with 1 to 18 carbon atoms and Y is the residue of an aliphatic saturated or unsaturated or aromatic dicarboxylic acid, are used as softeners p in the finishing of regenerated cellulose which has been impregnated with resins such as methylol urea, dimethylol urea, and methylolamine condensates with formaldehyde, and formaldehyde condensation products with 2,6 diamino-4-methyl1,3,5 triazine or pentamethylol and triamino-triazine or 2,4,6-triamino-1,3,5-triazine.
GB3749261A 1960-12-09 1961-10-19 Citric acid esters and method for their preparation Expired GB923847A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEB60417A DE1143502B (en) 1960-12-09 1960-12-09 Process for the production of bis-citric acid esters
DEB0060418 1960-12-09

Publications (1)

Publication Number Publication Date
GB923847A true GB923847A (en) 1963-04-18

Family

ID=25965807

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3749261A Expired GB923847A (en) 1960-12-09 1961-10-19 Citric acid esters and method for their preparation

Country Status (2)

Country Link
BE (1) BE611397A (en)
GB (1) GB923847A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4710532A (en) * 1985-03-13 1987-12-01 Morflex Chemical Company, Inc. Medical article and method
US4711922A (en) * 1985-05-17 1987-12-08 Morflex Chemical Company, Inc. Citrate esters and methods
US4789700A (en) * 1984-06-11 1988-12-06 Morflex Chemical Company, Inc. Citrate esters and method
US4824893A (en) * 1984-06-11 1989-04-25 Morflex Chemical Company, Inc. Citrate esters and methods
US4870204A (en) * 1984-06-11 1989-09-26 Morflex Chemical Company, Inc. Method for preparing citrate esters
US4883905A (en) * 1984-06-11 1989-11-28 Morflex Chemical Company, Inc. Process for preparing citrates using organic titanates
US4892967A (en) * 1984-06-11 1990-01-09 Morflex Chemical Company, Inc. Citrate esters
US4954649A (en) * 1984-06-11 1990-09-04 Morflex Chemical Company, Inc. Method for producing citrates
US5055609A (en) * 1984-06-11 1991-10-08 Morflex, Inc. Method for producing citrates by esterification in the presence of organic titanates

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4789700A (en) * 1984-06-11 1988-12-06 Morflex Chemical Company, Inc. Citrate esters and method
US4824893A (en) * 1984-06-11 1989-04-25 Morflex Chemical Company, Inc. Citrate esters and methods
US4870204A (en) * 1984-06-11 1989-09-26 Morflex Chemical Company, Inc. Method for preparing citrate esters
US4883905A (en) * 1984-06-11 1989-11-28 Morflex Chemical Company, Inc. Process for preparing citrates using organic titanates
US4892967A (en) * 1984-06-11 1990-01-09 Morflex Chemical Company, Inc. Citrate esters
US4954649A (en) * 1984-06-11 1990-09-04 Morflex Chemical Company, Inc. Method for producing citrates
US5055609A (en) * 1984-06-11 1991-10-08 Morflex, Inc. Method for producing citrates by esterification in the presence of organic titanates
US4710532A (en) * 1985-03-13 1987-12-01 Morflex Chemical Company, Inc. Medical article and method
US4711922A (en) * 1985-05-17 1987-12-08 Morflex Chemical Company, Inc. Citrate esters and methods

Also Published As

Publication number Publication date
BE611397A (en) 1962-03-30

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