GB623669A - Manufacture of glycol esters of terephthalic acid - Google Patents

Manufacture of glycol esters of terephthalic acid

Info

Publication number
GB623669A
GB623669A GB12585/47A GB1258547A GB623669A GB 623669 A GB623669 A GB 623669A GB 12585/47 A GB12585/47 A GB 12585/47A GB 1258547 A GB1258547 A GB 1258547A GB 623669 A GB623669 A GB 623669A
Authority
GB
United Kingdom
Prior art keywords
terephthalic acid
water
terephthalate
ethylene oxide
mixture
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
GB12585/47A
Inventor
Alan Charles Farthing
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 GB12585/47A priority Critical patent/GB623669A/en
Priority to NL139838A priority patent/NL67041C/en
Priority to FR965049D priority patent/FR965049A/en
Priority to CH270535D priority patent/CH270535A/en
Priority to DEP2368A priority patent/DE905736C/en
Publication of GB623669A publication Critical patent/GB623669A/en
Priority to GB23983/53A priority patent/GB744511A/en
Priority claimed from GB23983/53A external-priority patent/GB744511A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
    • C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • 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

Abstract

Ethylene glycol esters of terephthalic acid are prepared by reacting ethylene oxide with terephthalic acid at elevated temperature in an aqueous medium and in the presence of a small proportion of a terephthalate, e.g. an alkali metal or amine terephthalate. The amount of terephthalate used is sufficient to provide a ratio of cations to molecules of terephthalic acid of between 1 : 5 and 1 : 2. In examples: (1) ethylene oxide is passed into a mixture of terephthalic acid, potassium hydroxide and water and the bis-(b -hydroxyethyl)-terephthalate crystallized from the solution by cooling; (2) ethylene oxide is passed into a mixture of terephthalic acid, pyridine and water; and (3) ethylene oxide is forced by means of compressed nitrogen into a mixture of terephthalic acid, sodium hydroxide and water contained in an autoclave. The product of the last example is purified from contaminating b -hydroxyethyl hydrogen phthalate by suspending in water, adding sodium carbonate, filtering and crystallizing the solid from boiling water. b -Hydroxyethyl hydrogen phthalate is obtained by acidifying the sodium carbonate washings.
GB12585/47A 1947-05-09 1947-05-09 Manufacture of glycol esters of terephthalic acid Expired GB623669A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB12585/47A GB623669A (en) 1947-05-09 1947-05-09 Manufacture of glycol esters of terephthalic acid
NL139838A NL67041C (en) 1947-05-09 1948-04-09 Preparation of terephthalic acid glycol esters
FR965049D FR965049A (en) 1947-05-09 1948-04-22 Manufacture of glycolic esters of terephthalic acid
CH270535D CH270535A (en) 1947-05-09 1948-05-08 Process for the preparation of bis (B-oxy-ethyl) -terephthalate.
DEP2368A DE905736C (en) 1947-05-09 1949-03-27 Process for the preparation of ethylene glycol esters of terephthalic acid
GB23983/53A GB744511A (en) 1947-05-09 1953-08-31 Manufacture of polyesters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB12585/47A GB623669A (en) 1947-05-09 1947-05-09 Manufacture of glycol esters of terephthalic acid
GB23983/53A GB744511A (en) 1947-05-09 1953-08-31 Manufacture of polyesters

Publications (1)

Publication Number Publication Date
GB623669A true GB623669A (en) 1949-05-20

Family

ID=42831321

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12585/47A Expired GB623669A (en) 1947-05-09 1947-05-09 Manufacture of glycol esters of terephthalic acid

Country Status (1)

Country Link
GB (1) GB623669A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2662093A (en) * 1951-09-28 1953-12-08 Du Pont Process of preparing monomeric glycol terephthalates
US2681360A (en) * 1951-09-28 1954-06-15 Du Pont Mixed lithium hydride-metal organic carboxylate salt catalysts for ester interchange reaction and process
US2932662A (en) * 1958-08-01 1960-04-12 Chemstrand Corp Manufacture of bis (beta-hydroxyethyl) terephthalate with ethylene oxide
DE1085867B (en) * 1953-08-03 1960-07-28 Glanzstoff Ag Process for the production of mixed esters of terephthalic acid
DE1100613B (en) * 1958-05-22 1961-03-02 Bataafsche Petroleum Process for the preparation of bis (‰ -hydroxyalkyl) terephthalates and / or isophthalates
US3052711A (en) * 1960-04-20 1962-09-04 Du Pont Production of di(beta-hydroxyethyl) terephthalate
US3062862A (en) * 1961-02-02 1962-11-06 Du Pont Production of di-hydroxyethyl terephthalate
DE1139641B (en) * 1954-08-16 1962-11-15 Ici Ltd Process for the preparation of polyesters of terephthalic acid which are essentially free of Aether bonds
US3101366A (en) * 1961-03-22 1963-08-20 Socony Mobil Oil Co Inc Improved process for esterifying terephthalic acid with ethylene oxide
DE1155114B (en) * 1960-01-28 1963-10-03 Olin Mathieson Process for the preparation of bis (hydroxyalkyl) benzene dicarboxylic acid esters
US3140309A (en) * 1958-11-03 1964-07-07 Socony Mobil Oil Co Inc Preparation of isophthalic acid monoester
US4757097A (en) * 1986-06-24 1988-07-12 Bayer Aktiengesellschaft Process for the production of oligoesters containing hydroxy groups and their use
US20190382331A1 (en) * 2018-06-13 2019-12-19 Far Eastern New Century Corporation Process for preparing bis(2-hydroxyethyl) terephthalate

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681360A (en) * 1951-09-28 1954-06-15 Du Pont Mixed lithium hydride-metal organic carboxylate salt catalysts for ester interchange reaction and process
US2662093A (en) * 1951-09-28 1953-12-08 Du Pont Process of preparing monomeric glycol terephthalates
DE1085867B (en) * 1953-08-03 1960-07-28 Glanzstoff Ag Process for the production of mixed esters of terephthalic acid
DE1139641B (en) * 1954-08-16 1962-11-15 Ici Ltd Process for the preparation of polyesters of terephthalic acid which are essentially free of Aether bonds
DE1100613B (en) * 1958-05-22 1961-03-02 Bataafsche Petroleum Process for the preparation of bis (‰ -hydroxyalkyl) terephthalates and / or isophthalates
US2932662A (en) * 1958-08-01 1960-04-12 Chemstrand Corp Manufacture of bis (beta-hydroxyethyl) terephthalate with ethylene oxide
US3140309A (en) * 1958-11-03 1964-07-07 Socony Mobil Oil Co Inc Preparation of isophthalic acid monoester
DE1155114B (en) * 1960-01-28 1963-10-03 Olin Mathieson Process for the preparation of bis (hydroxyalkyl) benzene dicarboxylic acid esters
US3052711A (en) * 1960-04-20 1962-09-04 Du Pont Production of di(beta-hydroxyethyl) terephthalate
US3062862A (en) * 1961-02-02 1962-11-06 Du Pont Production of di-hydroxyethyl terephthalate
US3101366A (en) * 1961-03-22 1963-08-20 Socony Mobil Oil Co Inc Improved process for esterifying terephthalic acid with ethylene oxide
US4757097A (en) * 1986-06-24 1988-07-12 Bayer Aktiengesellschaft Process for the production of oligoesters containing hydroxy groups and their use
US20190382331A1 (en) * 2018-06-13 2019-12-19 Far Eastern New Century Corporation Process for preparing bis(2-hydroxyethyl) terephthalate

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