GB1458129A - Process for the preparation of beta-hydroxy-carbonyl compounds - Google Patents

Process for the preparation of beta-hydroxy-carbonyl compounds

Info

Publication number
GB1458129A
GB1458129A GB628674A GB628674A GB1458129A GB 1458129 A GB1458129 A GB 1458129A GB 628674 A GB628674 A GB 628674A GB 628674 A GB628674 A GB 628674A GB 1458129 A GB1458129 A GB 1458129A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
butanone
alkali metal
butanol
cyclohexanone
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
GB628674A
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 GB628674A priority Critical patent/GB1458129A/en
Priority to FR7504064A priority patent/FR2260557B1/fr
Priority to DE19752505580 priority patent/DE2505580C2/en
Priority to NL7501539A priority patent/NL7501539A/en
Publication of GB1458129A publication Critical patent/GB1458129A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • B01J23/04—Alkali metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro 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
    • C07C45/61—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
    • C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • 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
    • 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
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
    • 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
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated 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
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups

Landscapes

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

Abstract

1458129 Aldol process SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ BV 12 Feb 1974 06286/74 Heading C2C A process for the preparation of betahydroxycarbonyl compounds of which the carbon atom carrying the hydroxy group also carries a hydrogen atom comprises causing aldol condensation of an aldehyde in the liquid phase with a carbonyl compound of which a carbon atom bound to the carbonyl group carries at least one hydrogen atom, in the presence of a catalyst obtained by impregnation of a gammaalumina with a solution containing an alkali metal carbonate or an alkali metal compound which is converted by heating into an alkali metal carbonate (e.g. a bicarbonate, alcoholate, chelate or carboxylate), followed by heating at a temperature at which the carbonate loses carbon dioxide. Examples prepare 4-hydroxy- 6-methyl-2-heptanone from 3-methylbutanol; 4 - hydroxy - 2 - butanone from paraformaldehyde; 4 - hydroxy - 6,10 - dimethyl - 5,9- undecadien - 2 - one from citral; 4 - hydroxy- 4 - phenyl - 2 - butanone from benzaldehyde; 4 - hydroxy - 4 - (4 - acetoxyphenyl) - 2 - butanone from p - acetoxy benzaldehyde; 4- hydroxy - 4 - (4 - nitrophenyl) - 2 - butanone from p-nitrobenzaldehyde; acetone being the other reactant in each case; 2-hydroxypentyl phenyl ketone from butanol and acetophenone; 2-(1-hydroxybutyl)-cyclohexanone from butanol and cyclohexanone; and 2-ethyl-3-hydroxyhexanol from butanol alone.
GB628674A 1974-02-12 1974-02-12 Process for the preparation of beta-hydroxy-carbonyl compounds Expired GB1458129A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB628674A GB1458129A (en) 1974-02-12 1974-02-12 Process for the preparation of beta-hydroxy-carbonyl compounds
FR7504064A FR2260557B1 (en) 1974-02-12 1975-02-10
DE19752505580 DE2505580C2 (en) 1974-02-12 1975-02-10 Process for the preparation of β-hydroxycarbonyl compounds
NL7501539A NL7501539A (en) 1974-02-12 1975-02-10 PROCESS FOR PREPARING BETA-HYDROXYCARBON COMPOUNDS.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB628674A GB1458129A (en) 1974-02-12 1974-02-12 Process for the preparation of beta-hydroxy-carbonyl compounds

Publications (1)

Publication Number Publication Date
GB1458129A true GB1458129A (en) 1976-12-08

Family

ID=9811721

Family Applications (1)

Application Number Title Priority Date Filing Date
GB628674A Expired GB1458129A (en) 1974-02-12 1974-02-12 Process for the preparation of beta-hydroxy-carbonyl compounds

Country Status (4)

Country Link
DE (1) DE2505580C2 (en)
FR (1) FR2260557B1 (en)
GB (1) GB1458129A (en)
NL (1) NL7501539A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0177099A1 (en) * 1984-10-03 1986-04-09 Shell Internationale Researchmaatschappij B.V. Process for the preparation of synthesis gas from methanol
WO2000031011A1 (en) * 1998-11-25 2000-06-02 Imperial Chemical Industries Plc Aldol condensation

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4316990A (en) * 1980-10-29 1982-02-23 Eastman Kodak Company Preparation of α,β-aldehydes by aldol condensation
EP0106375B1 (en) * 1982-09-14 1987-01-14 Shell Internationale Researchmaatschappij B.V. Process for the preparation of nitrophenylalkanols
DE3523955A1 (en) * 1985-07-04 1987-01-08 Fritz Prof Dr Rostock Vibrator unit

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE223207C (en) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0177099A1 (en) * 1984-10-03 1986-04-09 Shell Internationale Researchmaatschappij B.V. Process for the preparation of synthesis gas from methanol
AU585535B2 (en) * 1984-10-03 1989-06-22 Shell Internationale Research Maatschappij B.V. Process for the preparation of synthesis gas from methanol
WO2000031011A1 (en) * 1998-11-25 2000-06-02 Imperial Chemical Industries Plc Aldol condensation
US6586636B2 (en) 1998-11-25 2003-07-01 Imperial Chemical Industries Plc Aldol condensation

Also Published As

Publication number Publication date
NL7501539A (en) 1975-08-14
DE2505580A1 (en) 1975-08-14
FR2260557A1 (en) 1975-09-05
FR2260557B1 (en) 1978-10-27
DE2505580C2 (en) 1983-12-29

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