GB1458129A - Process for the preparation of beta-hydroxy-carbonyl compounds - Google Patents
Process for the preparation of beta-hydroxy-carbonyl compoundsInfo
- 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
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.
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 |
NL7501539A NL7501539A (en) | 1974-02-12 | 1975-02-10 | PROCESS FOR PREPARING BETA-HYDROXYCARBON COMPOUNDS. |
DE19752505580 DE2505580C2 (en) | 1974-02-12 | 1975-02-10 | Process for the preparation of β-hydroxycarbonyl compounds |
FR7504064A FR2260557B1 (en) | 1974-02-12 | 1975-02-10 |
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)
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)
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 |
ATE24889T1 (en) * | 1982-09-14 | 1987-01-15 | Shell Int Research | PROCESS FOR THE PREPARATION OF NITROPHENYL CANOLS. |
DE3523955A1 (en) * | 1985-07-04 | 1987-01-08 | Fritz Prof Dr Rostock | Vibrator unit |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE223207C (en) * |
-
1974
- 1974-02-12 GB GB628674A patent/GB1458129A/en not_active Expired
-
1975
- 1975-02-10 DE DE19752505580 patent/DE2505580C2/en not_active Expired
- 1975-02-10 NL NL7501539A patent/NL7501539A/en not_active Application Discontinuation
- 1975-02-10 FR FR7504064A patent/FR2260557B1/fr not_active Expired
Cited By (4)
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 |
FR2260557B1 (en) | 1978-10-27 |
DE2505580A1 (en) | 1975-08-14 |
FR2260557A1 (en) | 1975-09-05 |
DE2505580C2 (en) | 1983-12-29 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |