GB1046608A - Cyclic acetals and ketals and their preparation - Google Patents

Cyclic acetals and ketals and their preparation

Info

Publication number
GB1046608A
GB1046608A GB39151/65A GB3915165A GB1046608A GB 1046608 A GB1046608 A GB 1046608A GB 39151/65 A GB39151/65 A GB 39151/65A GB 3915165 A GB3915165 A GB 3915165A GB 1046608 A GB1046608 A GB 1046608A
Authority
GB
United Kingdom
Prior art keywords
dioxan
dialkyl
dimethyl
heating
ketals
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
GB39151/65A
Inventor
Dhafir Yusuf Waddan
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB39151/65A priority Critical patent/GB1046608A/en
Publication of GB1046608A publication Critical patent/GB1046608A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 5,5-dimethyl-2-propyl-1, 3-dioxan and a general process for making cyclic acetals and ketals by heating a glycol with an aldehyde or ketone in the presence of a catalyst comprising one or more of the metals rhodium, iridium, palladium or platinum on a carbon support. Specified glycols include 1,2-, 1,3- and 1,4-aliphatic and alicyclic glycols, which may bear substituent groups, e.g. alkoxy and aryl radicals. Specified aldehydes and ketones include the aliphatic and aromatic carbonyl compounds and those bearing halogens and hydroxy substituents. 2-(51,51-Dialkyl - 11,31 - dioxan - 21 - yl) - 2,2 - dialkylethanols can be made by heating 2,2-dialkylpropane-1 3-diol with a 2,2-dialkyl-3-hydroxypropan-1-al in the presence of the above catalysts, the 2,2-dialkyl-3-hydroxypropan-1-al being prepared in situ by heating the 2,2-dialkylpropane-1,3-diol in the presence of said catalysts. The process can be effected at normal or superatmospheric pressure, preferably at temperatures of 50-250 DEG C. and optionally in the presence of a solvent. Examples relate to the preparation of 5,5 - dimethyl - 2 - propyl - 1,3 - dioxan, 2 - tribromomethyl - 1,3 - dioxolan, cyclohexane - spiro - 21 - (11, 31 - dioxolan), and 2 - (51, 51 - dimethyl - 11, 31 - dioxan - 21 - yl) - 2 - methylpropan-1-ol.
GB39151/65A 1965-09-14 1965-09-14 Cyclic acetals and ketals and their preparation Expired GB1046608A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB39151/65A GB1046608A (en) 1965-09-14 1965-09-14 Cyclic acetals and ketals and their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39151/65A GB1046608A (en) 1965-09-14 1965-09-14 Cyclic acetals and ketals and their preparation

Publications (1)

Publication Number Publication Date
GB1046608A true GB1046608A (en) 1966-10-26

Family

ID=10407940

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39151/65A Expired GB1046608A (en) 1965-09-14 1965-09-14 Cyclic acetals and ketals and their preparation

Country Status (1)

Country Link
GB (1) GB1046608A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0405271A1 (en) * 1989-06-29 1991-01-02 Hoechst Aktiengesellschaft Process for the production 1,3-dioxolane and 1,3-dioxane derivatives
US20120330069A1 (en) * 2011-06-24 2012-12-27 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US9315485B2 (en) 2011-06-24 2016-04-19 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US9382179B2 (en) 2011-06-24 2016-07-05 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9394271B2 (en) 2011-06-24 2016-07-19 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9440944B2 (en) 2011-06-24 2016-09-13 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0405271A1 (en) * 1989-06-29 1991-01-02 Hoechst Aktiengesellschaft Process for the production 1,3-dioxolane and 1,3-dioxane derivatives
AU623023B2 (en) * 1989-06-29 1992-04-30 Hoechst Aktiengesellschaft Process for the preparation of derivatives of 1,3-dioxolane and of 1,3-dioxane
US20120330069A1 (en) * 2011-06-24 2012-12-27 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US9315485B2 (en) 2011-06-24 2016-04-19 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US9382179B2 (en) 2011-06-24 2016-07-05 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9388105B2 (en) * 2011-06-24 2016-07-12 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US9394271B2 (en) 2011-06-24 2016-07-19 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9440944B2 (en) 2011-06-24 2016-09-13 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts

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