GB381686A - Improvements in the manufacture and production of hydroxy ketones - Google Patents

Improvements in the manufacture and production of hydroxy ketones

Info

Publication number
GB381686A
GB381686A GB2498831A GB2498831A GB381686A GB 381686 A GB381686 A GB 381686A GB 2498831 A GB2498831 A GB 2498831A GB 2498831 A GB2498831 A GB 2498831A GB 381686 A GB381686 A GB 381686A
Authority
GB
United Kingdom
Prior art keywords
heated
formaldehyde
autoclave
acetone
aqueous
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
GB2498831A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB2498831A priority Critical patent/GB381686A/en
Publication of GB381686A publication Critical patent/GB381686A/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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
    • C07C49/497—Saturated compounds containing a keto group being part of a ring containing hydroxy groups a keto group being part of a six-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Methylol-ketones are manufactured from open chain aliphatic or cycloaliphatic ketones and formaldehyde or agents supplying formaldehyde, such as paraformaldehyde and trioxymethylene, by warming the said initial materials in a neutral aqueous or aqueous-alcoholic medium in the absence of condensing agents. The reaction may be carried out at 50-200 DEG C., preferably at about 100-150 DEG C., and preferably in closed, pressure-tight vessels. In order to ensure the complete consumption of the aldehyde, excess of ketone, e.g. two molecular proportions or more, may be employed. In examples: (1) acetone and aqueous formaldehyde are heated to 100 DEG C. in a low pressure vessel to produce unsymmetrical dimethylolacetone; (2) methylethyl ketone and aqueous formaldehyde are heated in an autoclave to 120 DEG C. yielding dimethylol-methylethyl ketone; (3) acetone is heated with trioxymethylene and aqueous formaldehyde in an autoclave to 120 DEG C., producing dimethylol-acetone; (4) cyclohexanone and aqueous formaldehyde are heated in an autoclave to 120 DEG C. to produce a compound of the probable formula <FORM:0381686/IV/1> (5) acetone is heated with trioxymethylene, aqueous formaldehyde and ethyl alcohol in an autoclave to 120 DEG C. yielding dimethylolacetone.
GB2498831A 1931-09-05 1931-09-05 Improvements in the manufacture and production of hydroxy ketones Expired GB381686A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2498831A GB381686A (en) 1931-09-05 1931-09-05 Improvements in the manufacture and production of hydroxy ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2498831A GB381686A (en) 1931-09-05 1931-09-05 Improvements in the manufacture and production of hydroxy ketones

Publications (1)

Publication Number Publication Date
GB381686A true GB381686A (en) 1932-10-13

Family

ID=10220397

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2498831A Expired GB381686A (en) 1931-09-05 1931-09-05 Improvements in the manufacture and production of hydroxy ketones

Country Status (1)

Country Link
GB (1) GB381686A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2462031A (en) * 1945-06-16 1949-02-15 Gen Mills Inc Condensation of ketones with formaldehyde
US2480347A (en) * 1945-06-16 1949-08-30 Gen Mills Inc Esters
US3544634A (en) * 1966-09-15 1970-12-01 Basf Ag Production of 3-ketobutanol-(1)
DE1618098B1 (en) * 1967-02-25 1971-10-14 Basf Ag Process for the preparation of alkenols and alkenones

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2462031A (en) * 1945-06-16 1949-02-15 Gen Mills Inc Condensation of ketones with formaldehyde
US2480347A (en) * 1945-06-16 1949-08-30 Gen Mills Inc Esters
US3544634A (en) * 1966-09-15 1970-12-01 Basf Ag Production of 3-ketobutanol-(1)
DE1618098B1 (en) * 1967-02-25 1971-10-14 Basf Ag Process for the preparation of alkenols and alkenones

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