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GB437790A - Glycol ester derivatives - Google Patents

Glycol ester derivatives

Info

Publication number
GB437790A
GB437790A GB9935/35A GB993535A GB437790A GB 437790 A GB437790 A GB 437790A GB 9935/35 A GB9935/35 A GB 9935/35A GB 993535 A GB993535 A GB 993535A GB 437790 A GB437790 A GB 437790A
Authority
GB
United Kingdom
Prior art keywords
mols
acid
product
anhydride
esterified
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
GB9935/35A
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.)
Carbide and Carbon Chemicals Corp
Original Assignee
Carbide and Carbon Chemicals Corp
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 Carbide and Carbon Chemicals Corp filed Critical Carbide and Carbon Chemicals Corp
Publication of GB437790A publication Critical patent/GB437790A/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
    • C07C69/66—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
    • 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
    • C07C69/68—Lactic acid esters

Landscapes

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

Abstract

Alkoxy esters of acylated hydroxy acids are obtained by treating a hydroxy carboxylic acid containing one or more carboxylic groups with a glycol ether to esterify all the carboxyl groups, and then esterifying the free hydroxy groups with an aliphatic monocarboxylic acid. Suitable hydroxy acids include lactic, malic, citric, tartaric and saccharic acids, and suitable ethers include the methyl, ethyl, butyl or other alkyl ethers of ethylene glycol or diethylene glycol. The monoethers of propylene or dipropyleneglycol may also be used. For the esterification of the hydroxy groups in the original acid, acetic acid or anhydride or propionic and butyric anhydrides may be used. The products are stable and may be used as plasticizers. The butyryl derivatives are less soluble in water than the acetyl derivatives. According to examples: (1) 4 mols. of tartaric acid and 8,5 mols. of the monobutyl ether of ethylene glycol were heated, using 0-1 per cent of sulphuric acid as catalyst. Water formed was removed with benzene and the reaction completed at 158 DEG C. 8,3 mols. of acetic anhydride were added and the mixture boiled at 130 DEG C. for two hours. Excess acetic acid and anhydride were removed by distillation under reduced pressure. The product was di-(butoxyethyl)diacetyl tartrate. (2) In a similar manner, 2 mols. of citric acid and 8 mols. of monomethyl ether of ethylene glycol were esterified, and the product then esterified with 3 mols. of acetic anhydride. The product was tri-(methoxyethyl) acetyl citrate. (3) 12 Mols. of monomethyl ether of diethylene glycol were esterified with 85 per cent 10 mols. of lactic acid, using 1 per cent of aluminium sulphate as catalyst at a temperature of 95--140 DEG C. Excess ether was distilled off and the product esterified with 12 mols. of butyric anhydride at a temperature of 170--150 DEG C. The product was b -ethoxy ethoxy ethyl butynyl lactate.
GB9935/35A 1934-04-11 1935-03-30 Glycol ester derivatives Expired GB437790A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US437790XA 1934-04-11 1934-04-11

Publications (1)

Publication Number Publication Date
GB437790A true GB437790A (en) 1935-11-05

Family

ID=21928849

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9935/35A Expired GB437790A (en) 1934-04-11 1935-03-30 Glycol ester derivatives

Country Status (1)

Country Link
GB (1) GB437790A (en)

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