GB732086A - Complex formal lubricating composition - Google Patents

Complex formal lubricating composition

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Publication number
GB732086A
GB732086A GB20352/53A GB2035253A GB732086A GB 732086 A GB732086 A GB 732086A GB 20352/53 A GB20352/53 A GB 20352/53A GB 2035253 A GB2035253 A GB 2035253A GB 732086 A GB732086 A GB 732086A
Authority
GB
United Kingdom
Prior art keywords
alcohol
glycol
alcohols
complex
formals
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
GB20352/53A
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.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
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 Standard Oil Development Co filed Critical Standard Oil Development Co
Publication of GB732086A publication Critical patent/GB732086A/en
Expired legal-status Critical Current

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    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/105—Silica
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

Synthetic lubricating compositions comprise complex formals of general formula <FORM:0732086/IV (b)/1> wherein A and B are C1 to C60 organic groups, x and n are integers not less than 2 and y is an integer, the total number of carbon atoms in the molecule being from 20 to 130. The lubricants have good viscosity properties at high and low temperatures, and low rates of formation of combustion chamber deposits. The complex formals are prepared by conventional methods using three lines of approach: (I) All the reactants (i.e. the required alcohol, the required glycol and formaldehyde) may be mixed in the reaction zone, in the proportions in which they appear in the product molecules of the invention, and heated to reflux temperature in a water-entraining agent such as hexane or heptane. After recovery of the theoretical amount of water, the product is washed free of any acid catalyst and stripped free of unreacted components; (II) x moles of a glycol are reacted with x-1 moles of formaldehyde to obtain the central portion of the complex formal, i.e. <FORM:0732086/IV (b)/2> The hemiformal of the alcohol, i.e. R-O-CH2-OH is formed separately, the materials are mixed, heated to reflux temperature and treated as in (I); (III) the hemiformal of the chosen alcohol is first made by heating equal moles of the alcohol and formaldehyde. The desired molar proportions of a glycol and formaldehyde are added and the mixture reacted to form the "hydroxy complex" represented by R-O-[CH2-O-(CnH2nO)y]xH and two moles of this reacted with one mole of formaldehyde. Extensive lists of compounds containing alcoholic hydroxyl groups, which are used to prepare the formals, are given. The main types with examples are (1) Unsubstituted alcohols: monohydric aliphatic, e.g. propyl alcohol, decyl alcohol, crotyl alcohol, C3 to C20 "Oxo" alcohols; monohydric aromatic, e.g. benzyl alcohol, cinnamyl alcohol; polyhydric, e.g. 1 : 3-butanediol, triethylene glycol, 1 : 2-cyclohexanediol, pentaerythritol, benzotrimethylol. (2) Substituted alcohols: monohydric aliphatic, e.g. ethylene chlorhydrin, ethanolamine, 2-nitrobutanol, glycol monoesters, glycol monoethers, glycol monoformals; monohydric aromatic, e.g. p-methoxy benzyl alcohol, chlorobenzyl alcohols, nitrobenzyl alcohols, 2-anilino-ethanol; polyhydric, e.g. 2-chloro-1 : 3-propanediol, 2-nitro-1 : 3-propanediol, diethanolamine. Other compounds are esters of hydroxy acids and carbonyl substituted alcohols. A list of the acids which may be used to prepare the glycol monoesters is given. The preferred monohydroxy compounds are the highly branched chain aliphatic alcohols containing from 8 to 20 carbon atoms, prepared by the "Oxo" synthesis. A detailed description of the preparation of these alcohols is given. In examples the complex formals of the general formula are prepared. Compounds are prepared: (1) from C13 "Oxo" alcohols (A and B) and tripropylene glycol, x=3; (2) as in (1) but x=2; (3) from n-butyl carbitol and polypropylene glycol 150, x=2; (4) as in (1) and (2) but having the average molecular formula where x=2.3; (5) from C13 "Oxo" alcohol and triethylene glycol, x=2; (6) from C13 "Oxo" alcohol and pentanediol-1 : 5, x=3. The complex formals may be used as the lubricant base for grease compositions or blended with mineral oils or other synthetic lubricants (see Group III). They are also useful as plasticizers, solubilizers, insecticides, weed killers, rust preventives, solvents, dewaxing aids, detergents and as raw materials for household detergents or fumigants.ALSO:Synthetic lubricating compositions comprise complex formals of general formula <FORM:0732086/III/1> wherein A and B are C2 to C60 organic groups, x and n are integers not less than 2 and y is an integer, the total number of carbon atoms in the molecule being from 20 to 130 (see Group IV (b)). They may be blended with mineral oil or other synthetic lubricants, and are compatible and may be blended with lubrication addition agents such as viscosity index improvers, pour point depressers, detergents, rust inhibitors and antioxidants. They may serve as the lubricant base for grease compositions and may be thickened to stable grease structures with grease-forming soaps such as the lithium soaps of high molecular weight substantially saturated fatty acids, the N-acyl p-aminophenols, silica gels and treated bentonites. The formulation and preparation of a grease containing 79 per cent complex formal, 20 per cent lithium fatty acid soap (Litholite A) and 1 per cent phenyl alphanaphthylamine is described.
GB20352/53A 1952-11-29 1953-07-22 Complex formal lubricating composition Expired GB732086A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US732086XA 1952-11-29 1952-11-29

Publications (1)

Publication Number Publication Date
GB732086A true GB732086A (en) 1955-06-15

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GB20352/53A Expired GB732086A (en) 1952-11-29 1953-07-22 Complex formal lubricating composition

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FR (1) FR1087975A (en)
GB (1) GB732086A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2057196A1 (en) * 1969-12-04 1971-06-09 Mobil Oil Corp Improved lubricant masses

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2057196A1 (en) * 1969-12-04 1971-06-09 Mobil Oil Corp Improved lubricant masses

Also Published As

Publication number Publication date
FR1087975A (en) 1955-03-02

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