GB796508A - A process for the reaction of organic compounds containing hydroxyl groups with ethylene oxide - Google Patents
A process for the reaction of organic compounds containing hydroxyl groups with ethylene oxideInfo
- Publication number
- GB796508A GB796508A GB24940/55A GB2494055A GB796508A GB 796508 A GB796508 A GB 796508A GB 24940/55 A GB24940/55 A GB 24940/55A GB 2494055 A GB2494055 A GB 2494055A GB 796508 A GB796508 A GB 796508A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethylene oxide
- ethers
- alcohols
- mols
- hydroxy
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
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
Hydroxy ethyl ethers are prepared by reacting ethylene oxide with an organic compound which contains at least one alcoholic hydroxy group and is free of aliphatic unsaturation, in the presence of at least 0.05 per cent by weight of antimony pentachloride based on the weight of organic hydroxy compound. The reaction is preferably effected at temperatures from about 60 DEG C. upwards under atmospheric or elevated pressure using 0.1 to 1 per cent of catalyst. The organic hydroxy compounds utilizable include mono-and poly-hydric alcohols, amino-alcohols, carboxylic acid alkylol amides, partial esters of carboxylic acids with polyhydric alcohols, and partial ethers of polyhydric alcohols including partial ethers of phenols with polyhydric alcohols. The hydroxy compounds may contain from 1 to 30 or more carbon atoms and may be saturated aliphatic, cycloaliphatic or aromatic in nature; the alcohols are preferably primary or secondary. The amount of ethylene oxide used may vary. Reaction between lower hydroxy compounds and 1-4 mols. of ethylene oxide yields ethers useful as solvents. Lower and higher alcohols reacted with 4-30 mols. of ethylene oxide yield polyethers useful as hydraulic liquids, surfaceactive materials and glycerine substitutes. Larger quantities of ethylene oxide may be used to obtain resins (see Group IV (a)). Examples describe the reaction of the following compounds with various amounts of ethylene oxide at 100-130 DEG C. under atmospheric or raised pressure to yield mixtures of ethers comprising generally mono- and poly-(up to tetra) glycol ethers but also higher polyethers: (1) lauryl alcohol, (4) n-octyl alcohol, (5) sec. C7 alcohols from cracked olefines, (6) stearyl alcohol, (7) alcohols obtained by reduction of coconut fatty acids, (8) n-decanol, (9) ethylene chlorhydrin, (10) glycerol, (11) ethylene glycol, (12) n-butanol, (13) monoethanol amine and (14) 2-phenyl ethanol. In (11) the product obtained with 5 mols. ethylene oxide is reacted in stages with more ethylene oxide to form higher polyethoxy ethers. Examples (5) and (7) include comparative experiments using sodium methylate as catalyst.ALSO:Polyoxyethylene ethers are prepared by reacting ethylene oxide with an organic compound containing at least one alcoholic hydroxy group and which is free from aliphatic unsaturation, in the presence of at least 0.05 per cent by weight of hydroxy compound, as catalyst. By using sufficient ethylene oxide, wax-like to resin-like compounds may be obtained having molar weights of up to 4000-12,000. The hydroxy compounds may be mono- or polyhydric alcohols, amino-alcohols, carboxylic acid alkylol amides, partial esters of carboxylic acids with polyhydric alcohols and partial ethers of polyhydric alcohols, e.g. partial phenol ethers thereof, and may contain from 1-30 or more carbon atoms and be saturated aliphatic, cycloaliphatic or aromatic in structure. Reaction may be effected at 60 DEG C. or higher under ordinary or raised pressure using up to 30 mols. or more of ethylene oxide per mol. of hydroxy compound. In examples, higher polyglycol ethers are obtained from (6) stearyl alcohol and 6.6 mols. ethylene oxide; (7) alcohols obtained by reduction of coconut fatty acids and 7-8 mols. ethylene oxide; (9) ethylene chlorhydrin and 12 mols. ethylene oxide; (10) glycerol and 6.6 mols. ethylene oxide; (11) ethylene glycol and amounts of ethylene oxide added in stages to give products of M.W. from 284 up to 1096; and (13) monoethanolamine and 6.7 mols. ethylene oxide. Lauryl alcohol, n-octyl alcohol, mixed C7 sec.-alcohols, n-decanol, n-butanol and 2-phenyl-ethanol are other specified hydroxylic reagents which are used in further examples to obtain low M.W. mono- and poly-ethoxy ethers (see Group IV(b)). Example 7 includes a comparative experiment using sodium methylate as catalyst.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE796508X | 1954-09-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB796508A true GB796508A (en) | 1958-06-11 |
Family
ID=6710964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24940/55A Expired GB796508A (en) | 1954-09-01 | 1955-08-31 | A process for the reaction of organic compounds containing hydroxyl groups with ethylene oxide |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB796508A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3081354A (en) * | 1960-02-17 | 1963-03-12 | Monsanto Chemicals | Method of preparing adducts of ethenoxy-substituted glycidyl ethers and alcohols or mercaptans |
US3174943A (en) * | 1960-08-08 | 1965-03-23 | I C I Organics Inc | Plasticized urea-formaldehyde resins |
US3406208A (en) * | 1962-05-17 | 1968-10-15 | Henkel & Compagnie G M B H | Polyglycol ethers suitable for detergent preparations, and process for preparing the same |
US3969417A (en) * | 1967-05-16 | 1976-07-13 | Henkel & Cie G.M.B.H. | Process for the alkoxylation of compounds containing alcoholic hydroxyl groups |
EP0453967A1 (en) * | 1990-04-21 | 1991-10-30 | Hoechst Aktiengesellschaft | Process for the preparation of alkoxylates with a narrow distribution of homologues |
US5210323A (en) * | 1991-05-31 | 1993-05-11 | Hoechst Aktiengese Ilschaft | Process for the preparation of alkoxylates having a narrow distribution of homologs using antimony pentahalide complexes as the catalyst |
US5600020A (en) * | 1993-12-07 | 1997-02-04 | Hoechst Aktiengesellschaft | Process for the preparation of alkoxylates using ester compounds as catalyst |
US6365541B1 (en) * | 1998-02-26 | 2002-04-02 | Clariant Gmbh | Alkoxylation catalyst |
US6455459B1 (en) | 1999-11-18 | 2002-09-24 | Union Carbide Chemicals & Plastics Technology Corporation | Antimony catalyst compositions |
EP4015497A1 (en) | 2020-12-18 | 2022-06-22 | Clariant International Ltd | Alkoxylates prepared by calcium catalyst |
WO2022129374A1 (en) | 2020-12-18 | 2022-06-23 | Unilever Ip Holdings B.V. | Detergent composition |
-
1955
- 1955-08-31 GB GB24940/55A patent/GB796508A/en not_active Expired
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3081354A (en) * | 1960-02-17 | 1963-03-12 | Monsanto Chemicals | Method of preparing adducts of ethenoxy-substituted glycidyl ethers and alcohols or mercaptans |
US3174943A (en) * | 1960-08-08 | 1965-03-23 | I C I Organics Inc | Plasticized urea-formaldehyde resins |
US3406208A (en) * | 1962-05-17 | 1968-10-15 | Henkel & Compagnie G M B H | Polyglycol ethers suitable for detergent preparations, and process for preparing the same |
US3969417A (en) * | 1967-05-16 | 1976-07-13 | Henkel & Cie G.M.B.H. | Process for the alkoxylation of compounds containing alcoholic hydroxyl groups |
EP0453967A1 (en) * | 1990-04-21 | 1991-10-30 | Hoechst Aktiengesellschaft | Process for the preparation of alkoxylates with a narrow distribution of homologues |
US5210323A (en) * | 1991-05-31 | 1993-05-11 | Hoechst Aktiengese Ilschaft | Process for the preparation of alkoxylates having a narrow distribution of homologs using antimony pentahalide complexes as the catalyst |
US5600020A (en) * | 1993-12-07 | 1997-02-04 | Hoechst Aktiengesellschaft | Process for the preparation of alkoxylates using ester compounds as catalyst |
US6365541B1 (en) * | 1998-02-26 | 2002-04-02 | Clariant Gmbh | Alkoxylation catalyst |
US6455459B1 (en) | 1999-11-18 | 2002-09-24 | Union Carbide Chemicals & Plastics Technology Corporation | Antimony catalyst compositions |
US6734327B2 (en) | 1999-11-18 | 2004-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation process using antimony catalyst |
EP4015497A1 (en) | 2020-12-18 | 2022-06-22 | Clariant International Ltd | Alkoxylates prepared by calcium catalyst |
WO2022129374A1 (en) | 2020-12-18 | 2022-06-23 | Unilever Ip Holdings B.V. | Detergent composition |
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