GB986871A - A process for the preparation of hydroxymethyl alpha-hydroxy alkyl ketones or monoethers thereof - Google Patents

A process for the preparation of hydroxymethyl alpha-hydroxy alkyl ketones or monoethers thereof

Info

Publication number
GB986871A
GB986871A GB994763A GB994763A GB986871A GB 986871 A GB986871 A GB 986871A GB 994763 A GB994763 A GB 994763A GB 994763 A GB994763 A GB 994763A GB 986871 A GB986871 A GB 986871A
Authority
GB
United Kingdom
Prior art keywords
dimer
aldehyde
amine
preparation
carbon atoms
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
GB994763A
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
Publication of GB986871A publication Critical patent/GB986871A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • 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
    • C07C49/175—Saturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups

Landscapes

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

Abstract

A process for the preparation of hydroxymethyl-a -hydroxyalkyl ketones of formula <FORM:0986871/C2/1> where R is H or an alkyl group, and R1 is H or a hydrocarbon group of 1-10 carbon atoms, by contacting the corresponding a ,b -dihydroxyaldehyde of formula <FORM:0986871/C2/2> or a dimer thereof, with a tertiary amine, the quantity of amine being less than equivalent/mol. of aldehyde or 2 equivalents/mol. dimer. In the above formulae the alkyl group R has preferably 1-3 carbon atoms, and R1 may be a branched or unbranched alkyl group, an alkenyl, cycloaliphatic, or aryl group, preferably a saturated hydrocarbon group having 1-6 carbon atoms. Any tertiary amine may be used in the process, including polyamines, and substituted amines if the substituent is unreactive in the process such as a halogen, ether or thioether substituent. The reaction may be carried out in substantially anhydrous conditions in a solvent inert for the amine. The concentration of tertiary amine lies in the range 0.01-0.75 equiv. of amine/mole aldehyde, or 0.02-1.5 equiv./mole dimer, and the temperature is maintained between 50 DEG and 150 DEG C. Pressure may be superatmospheric to maintain the starting aldehyde in the liquid phase. Examples indicate the preparation of dihydroxyacetone from glyceraldehyde and its dimer, and dihydroxyacetone-monomethylether from dimeric b -methoxylacetaldehyde. The dimer of an aldehyde which may be used as starting material in the above process and which is of the formula <FORM:0986871/C2/3> R and R1 having the above significance, is prepared by ageing an aqueous solution of the a -hydroxyaldehyde having a concentration of at least 40%, preferably between 40 and 70%, by weight. The dimer crystallizes out.
GB994763A 1962-03-15 1963-03-13 A process for the preparation of hydroxymethyl alpha-hydroxy alkyl ketones or monoethers thereof Expired GB986871A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18001762A 1962-03-15 1962-03-15

Publications (1)

Publication Number Publication Date
GB986871A true GB986871A (en) 1965-03-24

Family

ID=22658913

Family Applications (1)

Application Number Title Priority Date Filing Date
GB994763A Expired GB986871A (en) 1962-03-15 1963-03-13 A process for the preparation of hydroxymethyl alpha-hydroxy alkyl ketones or monoethers thereof

Country Status (2)

Country Link
BE (1) BE629539A (en)
GB (1) GB986871A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012084121A1 (en) * 2010-12-22 2012-06-28 Merck Patent Gmbh Dihydroxyacetone monoether

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012084121A1 (en) * 2010-12-22 2012-06-28 Merck Patent Gmbh Dihydroxyacetone monoether
US20130272978A1 (en) * 2010-12-22 2013-10-17 Merck Patent Gmbh Dihydroxyacetone monoethers

Also Published As

Publication number Publication date
BE629539A (en) 1963-10-21

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