GB1166636A - Process for the production of Cycloacetal Esters and Cycloketal Esters - Google Patents

Process for the production of Cycloacetal Esters and Cycloketal Esters

Info

Publication number
GB1166636A
GB1166636A GB5382266A GB5382266A GB1166636A GB 1166636 A GB1166636 A GB 1166636A GB 5382266 A GB5382266 A GB 5382266A GB 5382266 A GB5382266 A GB 5382266A GB 1166636 A GB1166636 A GB 1166636A
Authority
GB
United Kingdom
Prior art keywords
acid
esters
cycloketal
cycloacetal
mono
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
GB5382266A
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.)
Huels AG
Original Assignee
Chemische Werke Huels AG
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 Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of GB1166636A publication Critical patent/GB1166636A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan

Landscapes

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

Abstract

1,166,636. Cycloacetal and cycloketal esters. CHEMISCHE WERKE HULS A.G. 1 Dec., 1966 [2 Dec., 1965], No. 53822/66. Heading C2C. Cycloacetal esters and cycloketal esters are prepared by reacting a Cycloacetal alcohol or cycloketal alcohol, obtainable by heating in the presence of an acid catalyst and with removal of water of reaction an aldehyde, a C 3-7 aliphatic or cycloaliphatic ketone or an aromatic ketone and a triol of the formula l is 0 or 1-8, m is 0 or 1-14, + m being at least one, and each R represents hydrogen or an organic substituent, with a mono- or di-carboxylic acid, or an anhydride thereof, in the presence of a separate, strongly acidic catalyst having a pka of not more than 4 whilst removing the water of reaction to produce the mono-ester of the mono-acid or the di-ester of the di-acid. Many suitable aliphatic, cycloaliphatic and aromatic aldehydes and ketones and triols from which the starting cycloacetal and cycloketal alcohols can be prepared are specified. Suitable mono- and di-carboxylic acids include aliphatic, halogenated aliphatic, cycloaliphatic and aromatic acids. Esterification may be effected at 70‹-180‹ C. using stoichiometric proportions of alcohol and acid and in the presence of a water entrainer, e.g. benzene. Specified acidic catalysts having the required pka are H2SO 4 ,H 3 PO 4 , HC1O 4 , p-toluenesulphonic acid, trichloroacetic acid, cationic ionexchangers, and acid-treated bleaching earths, e.g. montmorillonite. Examples describe the preparation of esters from a variety of cycloacetal and cycloketal alcohols containing 1,3- dioxane and 1,3-dioxolane rings and formic, lauric, acetic, oxalic, butyric, chloroacetic, succinic, propionic, trichloroacetic, phenylacetic, adipic, benzoic, palmitic and α-ethylbutyric acids.
GB5382266A 1965-12-02 1966-12-01 Process for the production of Cycloacetal Esters and Cycloketal Esters Expired GB1166636A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC0037556 1965-12-02

Publications (1)

Publication Number Publication Date
GB1166636A true GB1166636A (en) 1969-10-08

Family

ID=7022874

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5382266A Expired GB1166636A (en) 1965-12-02 1966-12-01 Process for the production of Cycloacetal Esters and Cycloketal Esters

Country Status (3)

Country Link
DE (1) DE1493572A1 (en)
FR (1) FR1502385A (en)
GB (1) GB1166636A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819645A (en) * 2022-09-09 2023-03-21 浙江国能科技有限公司 Preparation method of polyreactive ultraviolet curing conductive adhesive resin matrix

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4243592A (en) * 1979-03-12 1981-01-06 The Upjohn Company 9,11-Dideoxy-10-oxa-TXB compounds
RU2503670C1 (en) * 2012-05-10 2014-01-10 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" Method of producing monochloroacetic acid ester containing 1,3-dioxane substitute

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819645A (en) * 2022-09-09 2023-03-21 浙江国能科技有限公司 Preparation method of polyreactive ultraviolet curing conductive adhesive resin matrix

Also Published As

Publication number Publication date
FR1502385A (en) 1967-11-18
DE1493572A1 (en) 1969-11-13

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees