GB601604A - Improvements in production of polyoxypropylene compounds - Google Patents
Improvements in production of polyoxypropylene compoundsInfo
- Publication number
- GB601604A GB601604A GB6923/45A GB692345A GB601604A GB 601604 A GB601604 A GB 601604A GB 6923/45 A GB6923/45 A GB 6923/45A GB 692345 A GB692345 A GB 692345A GB 601604 A GB601604 A GB 601604A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- water
- propylene oxide
- butanol
- reacted
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
- C10M107/34—Polyoxyalkylenes
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
- C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
- C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/46—Textile oils
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Lubricant compositions comprise mixtures of liquid, water-immiscible aliphatic monoethers of polyoxypropylene glycols having a viscosity of at least 3.0 centistokes at 210 DEG F. and an average molecular weight of at least 496. They may be combined with suitable non-aqueous diluents and monoethers of different viscosities may be blended. The compositions may be used for the lubrication of the surfaces of metals, rubber, textiles and the like; in this connection, wool, cotton, flax and hemp fibres are mentioned and it is stated that in the lubrication of synthetic films the products give a more desirable "hand" to the fibre. The mixtures of monoethers are obtained by reaction of 1,2-propylene oxide with an aliphatic monohydric alcohol in the presence of an alkaline catalyst, at least 8 mols of oxide being reacted per mol of alcohol and the product stripped if necessary to give an ether having the required properties (see Group IV (b)). Examples describe products having average molecular weights of up to about 1800 obtained from propylene oxide and methanol, butanol and 7-ethyl-2-methylundecanol-4. Other alcohols mentioned are ethanol, isopropanol, 2-ethyl-butanol, hexanol, 2-ethyl-hexanol and n-octanol. The Specification as open to inspection under Sect. 91 also describes products obtained from 1,2-propylene oxide containing up to 10 per cent ethylene oxide. This subject-matter does not appear in the Specification as accepted.ALSO:Liquid, water-immiscible aliphatic monoethers of polyoxypropylene glycols are prepared by introducing 1, 2-propylene oxide substantially free of aldehydes and water into a heated liquid body of an aliphatic monohydric alcohol containing an alkaline catalyst dispersed therein and being substantially free from water, continuing the introduction of the oxide at a rate to maintain an amount of unreacted oxide at a substantially uniform concentration in the reaction mixture until at least 8 mols of the introduced oxide are reacted per mol of alcohol, thereafter if necessary stripping the resulting product of volatile materials to obtain a residue having a viscosity of at least 3 centistokes at 210 DEG F. and an average molecular weight of at least 496. The process may be carried out in a closed system at 80 DEG to 130 DEG C. under a uniform pressure of up to about 65 lbs. and in the absence of oxygen; an inert gas may be present. Generally the reaction product is treated to neutralise the catalyst and then subjected to a washing treatment to extract water-soluble impurities including low molecular weight polyoxypropylene ethers before being stripped of low boiling substances. Water or aqueous salt solution may be used as the extractant, separation of the aqueous phase being facilitated by salting out or by extracting, preferably portionwise, in the presence of a water-insoluble solvent for the desired product, for example, dichlordiethyl ether, dibutyl ether, butanol, hexanol, toluene, benzene and ethylene dichloride. Alkaline catalysts for the process are sodium, potassium and lithium hydroxides or their alcoholates; the acidic catalyst boron trifluoride is stated to promote dimerisation of the propylene oxide to dioxane and its alkyl derivatives. The propylene oxide preferably contains not more than 0.1 per cent water and this is attainable by fractional distillation of the oxide, by distillation from a hygroscopic glycol or by scrubbing with a hygroscopic liquid. The products may be used as lubricants (see Group III) for surfaces of metals, rubber, natural textile fibres and synthetic fibres, in the latter case the products serve also as finishing agents; they may also be used as hydraulic liquids. In examples: (1) n-butanol and 1,2-propylene oxide are reacted in the presence of sodium hydroxide, whereupon water is added and the catalyst neutralised, the aqueous phase separated and the residue stripped under reduced pressure yielding products of average molecular weights varying from about 540 to 1750 according to the proportions used; (2) butanol, 7-ethy-2-methyl-undecanol-4- and methanol are each reacted, in presence of sodium hydroxide, with propylene oxide which is added in stages, samples being withdrawn at each stage and worked up yielding a series of fluids having average molecular weights of up to about 1500-1800. Other alcohols specified comprise ethanol, isopropanol, 2-ethyl butanol, n-hexanol, 2-ethyl hexanol and n-octanol. The Specification as open to inspection under Sect. 91 includes the use of 1,2-propylene oxide containing up to 10 per cent ethylene oxide and is not limited to the above method of introducing the oxide nor to the above-specified minimum amount of oxide to be reacted. This subject-matter does not appear in the Specification as accepted.ALSO:Liquid, water-immiscible aliphatic monoethers of polyoxypropylene glycols are prepared by introducing 1,2-propylene oxide substantially free of aldehydes and water into a heated liquid body of an aliphatic mono-hydric alcohol containing an alkaline catalyst dispersed therein and being substantially free p from water, containing the introduction of the oxide at a rate to maintain an amount of unreacted oxide at a substantially uniform concentration in the reaction mixture until at least 8 mols. of the introduced oxide are reacted per mol. of alcohol, thereafter if necessary stripping the resulting product of volatile materials to obtain a residue having a viscosity of at least 3 centistrokes at 210 DEG F. and an average molecular weight of at least 496. The process may be carried out in a closed system at 80 DEG to 130 DEG C. under a uniform pressure of up to about 65 lbs. and in the absence of oxygen; an inert gas may be present. Generally, the reaction product is treated to neutralize the catalyst and then subjected to a washing treatment to extract water-soluble impurities including low molecular weight polyoxypropylene ethers before being stripped of low boiling substances. Water or aqueous salt solution may be used as the extractant, separation of the aqueous phase being facilitated by salting out or by extracting, preferably portionwise, in the presence of a water-insoluble solvent for the desired product, for example, dichlordiethyl ether, dibutyl ether, butanol, hexanol, toluene, benzene and ethylene dichloride. Alkaline catalysts for the process are sodium, potassium and lithium hydroxides or their alcoholates; the acidic catalyst boron trifluoride is stated to promote dimerization of the propylene oxide to dioxane and its alkyl derivatives. The propylene oxide preferably contains not more than 0.1 per cent water and this is attainable by fractional distillation of the oxide, by distillation from a hygroscopic glycol or by scrubbing with a hygroscopic liquid. The products may be used as lubricants (see Group III) for surfaces of metals, rubber, natural textile fibres and synthetic fibres, in the latter case the products serve also as finishing agents; they may also be used as hydraulic liquids. In examples: (1) n-butanol and 1,2-propylene oxide are reacted in the presence of sodium hydroxide, whereupon water is added and the catalyst neutralized, the aqueous phase separated and the residue stripped under reduced pressure yielding products of average molecular weights varying from about 540 to 1750 according to the proportions used; (2) butanol, 7 - ethyl - 2 - methyl - undecanol - 4 and methanol are each reacted, in presence of sodium hydroxide, with propylene oxide which is added in stages, samples being withdrawn at each stage and worked up yielding a series of fluids having average molecular weights of up to about 1500-1800. Other alcohols specified comprise ethanol, isopropanol, 2-ethyl butanol, n-hexanol, 2-ethyl hexanol and n-octanol. The Specification as open to inspection under Sect. 91 includes the use of 1,2-propylene oxide containing up to 10 per cent ethylene oxide and is not limited to the above method of introducing the oxide nor to the above-specified minimum amount of oxide to be reacted. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US601604XA | 1944-05-30 | 1944-05-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB601604A true GB601604A (en) | 1948-05-10 |
Family
ID=22027756
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6923/45A Expired GB601604A (en) | 1944-05-30 | 1945-03-19 | Improvements in production of polyoxypropylene compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB601604A (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2706189A (en) * | 1952-06-05 | 1955-04-12 | Dow Chemical Co | Solid polymers of propylene oxide |
US2766292A (en) * | 1953-06-04 | 1956-10-09 | Petrolite Corp | Process for preparing oxyalkylated derivatives |
DE1059401B (en) * | 1951-12-22 | 1959-06-18 | Gen Aniline & Film Corp | Surface active agents |
DE974483C (en) * | 1952-05-03 | 1961-01-12 | Rhein Chemie G M B H | Process for improving the solubility and miscibility of naphthenic acid salts which contain monovalent or polyvalent cations in or with hydrocarbons |
US3356738A (en) * | 1963-12-11 | 1967-12-05 | Witco Chemical Corp | Purification of water-insoluble hydroxyl-containing polyethers |
GB2259711A (en) * | 1991-09-20 | 1993-03-24 | Nsk Ltd | Rolling bearing lubricant |
US5282689A (en) * | 1991-09-20 | 1994-02-01 | Nsk Ltd. | Rolling bearing |
US5385412A (en) * | 1991-09-20 | 1995-01-31 | Nsk Ltd. | Rolling bearing |
WO2002094951A1 (en) * | 2001-05-18 | 2002-11-28 | Basf Aktiengesellschaft | Glycol ether mixtures |
WO2020207881A1 (en) * | 2019-04-12 | 2020-10-15 | Basf Se | Metalworking fluid containing a branched alcohol propoxylate |
-
1945
- 1945-03-19 GB GB6923/45A patent/GB601604A/en not_active Expired
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1059401B (en) * | 1951-12-22 | 1959-06-18 | Gen Aniline & Film Corp | Surface active agents |
DE974483C (en) * | 1952-05-03 | 1961-01-12 | Rhein Chemie G M B H | Process for improving the solubility and miscibility of naphthenic acid salts which contain monovalent or polyvalent cations in or with hydrocarbons |
US2706189A (en) * | 1952-06-05 | 1955-04-12 | Dow Chemical Co | Solid polymers of propylene oxide |
US2766292A (en) * | 1953-06-04 | 1956-10-09 | Petrolite Corp | Process for preparing oxyalkylated derivatives |
US3356738A (en) * | 1963-12-11 | 1967-12-05 | Witco Chemical Corp | Purification of water-insoluble hydroxyl-containing polyethers |
FR2681655A1 (en) * | 1991-09-20 | 1993-03-26 | Nsk Ltd | ROLLING BEARING. |
GB2259711A (en) * | 1991-09-20 | 1993-03-24 | Nsk Ltd | Rolling bearing lubricant |
US5282689A (en) * | 1991-09-20 | 1994-02-01 | Nsk Ltd. | Rolling bearing |
US5385412A (en) * | 1991-09-20 | 1995-01-31 | Nsk Ltd. | Rolling bearing |
GB2259711B (en) * | 1991-09-20 | 1995-07-05 | Nsk Ltd | Rolling bearing |
WO2002094951A1 (en) * | 2001-05-18 | 2002-11-28 | Basf Aktiengesellschaft | Glycol ether mixtures |
WO2020207881A1 (en) * | 2019-04-12 | 2020-10-15 | Basf Se | Metalworking fluid containing a branched alcohol propoxylate |
US11795414B2 (en) | 2019-04-12 | 2023-10-24 | Basf Se | Metalworking fluid containing a branched alcohol propoxylate |
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