GB761296A - Improvements in or relating to methylene ether esters as synthetic lubricants - Google Patents
Improvements in or relating to methylene ether esters as synthetic lubricantsInfo
- Publication number
- GB761296A GB761296A GB23892/54A GB2389254A GB761296A GB 761296 A GB761296 A GB 761296A GB 23892/54 A GB23892/54 A GB 23892/54A GB 2389254 A GB2389254 A GB 2389254A GB 761296 A GB761296 A GB 761296A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylene
- alcohol
- esters
- oxo
- derived
- 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
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds 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
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
Abstract
The invention comprises methylene ether esters of the general formula R(OCH2OOCR1)x, wherein R is an organic group derived from an aliphatic monohydric alcohol or a glycol, R1 is derived from an aliphatic monocarboxylic acid, and x is 1 or 2, and wherein the total number of carbon atoms in the methylene ester is between 20 and 130, and wherein the methylene ester has an A.S.T.M. pour point below 35 DEG F., a flash point above 300 DEG F. and a kinematic viscosity at 210 DEG F. within the range of 2 to 60 centistokes. The alcohols from which the group R is derived may be oxo alcohols (particularly those having from 8 to 20 carbon atoms) and alcohols derived from the Guerbet and Aldol reactions-particularly with oxo alcohols (the Guerbet and Aldol reactions are referred to below). Suitable glycols and polyglycols from which R is derived are polyalkylene glycols particularly polymethylene glycols such as butanediol-1,4, pentanediol-1,5, 2,3-butylene glycol, 1,3-butylene glycol, 2-alkoxymethyl-2,4-dimethyl-pentanediol-1,5, hexylene glycol, 2,4-pentanediol and decanediol-1,10, and mixtures thereof. Suitable monocarboxylic acids from which R1 may be derived are acetic, propionic, butyric, 2-ethylbutyric, caprylic, 2-ethylhexanoic, caproic, pelargonic, lauric, myristic, oleic, stearic, glycollic, lactic, a hydroxystearic, a methoxypropionic, an ethoxyethoxyacetic, mono-C8-oxo-sebacate, and mono-2-ethylhexyl adipate acids, C3-C30-oxo acids including bottom acids, acids derived from petroleum fractions by oxidation, and acids derived from alcohols by alkali fusion. When x represents 1 in the above general formula, the desired compound may be prepared by (1) forming the chloromethyl ether of the required monohydric alcohol by reacting the alcohol with formaldehyde in the presence of hydrogen chloride, or by chlorinating the required methyl ether of the required monohydric alcohol, and the chloromethyl ether thus formed is reacted with the required carboxylic acid; or (2) reacting the required monohydric alcohol with one molar proportion of formaldehyde to form a hemi-formal which is then reacted with the required carboxylic acid chloride. In the examples (1) a tridecyloxymethyl stearate is prepared by reacting a C13-oxo alcohol, trioxymethylene and hydrogen chloride to form C13-oxo chloromethyl ether which is then reacted with stearic acid; (2) tridecyloxymethyl pelargonate is obtained as in (1) by first preparing tridecyl chloromethyl ether and then reacting it with pelargonic acid; and (3) a compound of the formula <FORM:0761296/IV(b)/1> is obtained by condensing ethylene glycol with trioxymethylene in the presence of hydrogen chloride to form a bis chloromethyl compound of the formula ClCH2OCH2CH2OCH2Cl and then reacting it with two equivalents of C13-oxo acids. Starting materials. Alcohols containing branched chains are prepared by either of the following methods: (1) The Guerbet reaction which is an alkaline condensation of primary or secondary alcohols and requires the presence of a methylene group adjacent to the carbinol group. The sodium alcoholate of the reacting alcohol is generally used as catalyst, metallic sodium being preferably added to the reaction mixture to form an alcoholate at the beginning of the reaction. Other alkaline agents such as sodium soaps, sodium borate or sodium allyl borate may also be used. The presence of a hydrogenating catalyst such as copper, zinc or nickel improves the yield of desired alcohol. An oxo alcohol is a suitable reactant for the Guerbet reaction. The Specification describes in detail the condensation of a C8-oxo alcohol in the presence of sodium hydroxide and copper powder. (2) The Aldol condensation which is the condensation of an aldehyde, e.g. a C8-oxo aldehyde, containing a methylene group adjacent to the carbonyl group in the presence of an alcohol and acid to form a b -hydroxy-aldehyde which is then dehydrated and hydrogenated. The aldehyde reactant must contain a methylene group adjacent to the carbonyl group.ALSO:Lubricating compositions comprise methylene esters having the general formula R(OCH2OOCR1)x wherein R is an organic group derived from an aliphatic monohydric alcohol or glycol, or a mixture of such alcohols or glycols, R1 is derived from an aliphatic monocarboxylic acid, x is 1 or 2 and the total number of carbon atoms in the methylene ester is between 20 and 130, the said methylene ester having an A.S.T.M. pour point below 35 DEG F., a flash point above 300 DEG F., and a kinematic viscosity at 210 DEG F. within the range of 2 to 60 centistokes. The above methylene esters may be added to natural or synthetic lubricating oils e.g., they may be blended with monoesters, with dibasic acid esters such as esters of adipic, sebacic, glutaric and succinic acids, with complex esters such as the alcohol-dibasic acid - glycol - dibasic acid -alcohol complex esters, and with mineral oils or polymerized hydrocarbons. The above methylene esters may be thickened by the addition of grease forming soaps such as lithium stearate or sodium hydroxy stearate, or by the addition of viscosity index improvers of the fumarate ester-vinyl ester polymer of methacrylate polymer type e.g., from 0.5 to 10 per cent by weight of a copolymer of acrylate or methacrylate esters having an ester chain length of 8 to 18 carbon atoms may be blended with the methylene esters. The methylene esters are compatible with pour point improvers such as polybutene, detergents, oxidation inhibitors and rust inhibitors. They may also be added to fuel oils.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US761296XA | 1953-11-06 | 1953-11-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB761296A true GB761296A (en) | 1956-11-14 |
Family
ID=22130091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23892/54A Expired GB761296A (en) | 1953-11-06 | 1954-08-17 | Improvements in or relating to methylene ether esters as synthetic lubricants |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB761296A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1107869B (en) * | 1958-04-12 | 1961-05-31 | Roehm & Haas Gmbh | Additives to hydraulic fluids based on mineral oil-free glycol ethers or triaryl phosphates |
CN103695053A (en) * | 2013-12-25 | 2014-04-02 | 济南开发区星火科学技术研究院 | Synthetic method of diesel oil cetane number improver |
WO2024086005A1 (en) | 2022-10-17 | 2024-04-25 | Oq Chemmicals Bishop Llc | Improved 1,3-butylene glycol process |
-
1954
- 1954-08-17 GB GB23892/54A patent/GB761296A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1107869B (en) * | 1958-04-12 | 1961-05-31 | Roehm & Haas Gmbh | Additives to hydraulic fluids based on mineral oil-free glycol ethers or triaryl phosphates |
CN103695053A (en) * | 2013-12-25 | 2014-04-02 | 济南开发区星火科学技术研究院 | Synthetic method of diesel oil cetane number improver |
CN103695053B (en) * | 2013-12-25 | 2015-11-18 | 济南开发区星火科学技术研究院 | A kind of synthetic method of diesel cetane-number improver |
WO2024086005A1 (en) | 2022-10-17 | 2024-04-25 | Oq Chemmicals Bishop Llc | Improved 1,3-butylene glycol process |
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