US2796401A - Complex formal lubricating composition - Google Patents

Complex formal lubricating composition Download PDF

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Publication number
US2796401A
US2796401A US323338A US32333852A US2796401A US 2796401 A US2796401 A US 2796401A US 323338 A US323338 A US 323338A US 32333852 A US32333852 A US 32333852A US 2796401 A US2796401 A US 2796401A
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United States
Prior art keywords
alcohol
glycol
complex
formal
viscosity
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US323338A
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Inventor
Alfred H Matuszak
William E Mcturk
Delmer L Cottle
David W Young
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to NL89229D priority Critical patent/NL89229C/xx
Priority to NLAANVRAGE7807232,A priority patent/NL181914B/xx
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to US323338A priority patent/US2796401A/en
Priority to DEST7387A priority patent/DE961483C/de
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    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/226—Morpholines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28—Amides; Imides
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • 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
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    • C10M2223/042—Metal salts thereof
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • C—CHEMISTRY; METALLURGY
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    • 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—Form in which the lubricant is applied to the material being lubricated semi-solid; 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation
    • 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

Definitions

  • The'pre'sent invention relates to anew type ofsynthetic lubiicating composition which comprises the formalis' of a wide range of organic compounds which contain at least one free' hydroxyl group" and which is alcoholic in nature and which contains at least" three CH"2O"-"1inkages. 7 p v It' has been'gene'rally accepted by the art that most acetals are not of'sufiieie'nt stability to serve as lubri'cat ing compositions; lt h'as'now beeri'foiind, however, and
  • a and B represent the organic compounds less the hydroxyl group.
  • x and n represent numbers having a value of 2 or more and y is 1 or more.
  • the radicals may be alike or different and may contain from 1 to 60 carbon atoms.
  • a and B are selected such that the total number of carbon atoms in the formal is between about 20 and 130,. with compounds containing fromv about 25 to carbon atoms being preferred.
  • the organic hydroxy compounds which serve as a source for the radicals A and B will be definedmore in detail below.
  • a lubricating composition For use in reciprocating engines, particularly as a lubricant for automotive engines, a lubricating composition must meet several requirements; In order to form an effective lubricating film and to maintain that film at low and high temperatures it must have certain viscosity characteristics. At low temperatures thelubricant must be sufiiciently labile to flow through: the circulatory system of the equipment and allowmovement of lubricated surfaces without an undue power requirement.
  • a lubricant having an ASTM pourpoint below about 35 F. has suflicient low temperature l'ahilit'y to make it satisfactory in these respects. for general. use.
  • a lubricant must hay'e sufii'cient body or thickness to furnish and maintain a: satisfactory lubricating film. It has been found that a lubricant that is satisfactory in this respect willl have: a viscosity at 210 F. of between about 2 to 60 centistokes, i. c. 32.8 and 280 Saybolt seconds, Universal; T e prevent undue lubricant loss, due to volatility" and general molecular disintegration and to insure againstiexplosion hazards at higher temperatures sometimesencounteredg a lubricating composition should have a flasli point in eXcess-of about 300 F. These requisites are inherent in the term lubricating compositions, as used in.
  • the reactants may b'e adriibced in the reacting zone and heated to reflux temperature in the presence of an entraining agent such" as' hexane", heptane or the like. After recovery of the water of theory the product is washed free of any acidi'c ca'talysts and stripped free of unreacted components.
  • Polyethylene glycols (a) Diethylene glycol 51;) Triethylene glycol c) Tetraethylene glycol 2.
  • Polypropylene glycols (a) Dipropylene glycol (b) Tripropylene glycol sh) 1,2-cyclohexanedio1 i) Decanedi0l-1.10 2.
  • Other polyhydric alcohols (11) Glycerol (b) 2hydroxymethyl-2-methyl-propanedlol-I,3 (c) Pentaerythritol I v d orbitol e) Dipentaerythritol f) Dulcitol Trimethylol propane 'letramethylol cyclohexanol t) Benzotrimethylol II.
  • Substituted alcohols Monohydric 1. Aliphatic (a) Halogenated alcohols 1. Ethylene chlorohydrin 2. Trlfluoro ethanol 3. Propylene chlorohydrln 4. The various chloro-substltuted monoethers of polyalkylene glycols Ethanolamine 2-amino propanol 2-m'troethanol 2-nitropropanol 2-nitrobutanol The various glycol monoesters, e. g. 1. Ethylene glycol monoacetate 2. Propylene glycol monobutyrate Butylene glycol monolaurate Polyethylene glycol monoesters Polypropylene glycol monoesters Polybutylene glycol monoesters he various glycol monoethers, e. g.
  • a-Hydroxy adipaldehvde 2.
  • B-Hydroxy propionaldehyde Particularly desirable organic hydroxy compounds for use in this invention are those highly branched chain aliphatic alcohols prepared by the OX0 synthesis.
  • This Oxo synthesis may be described as being the catalytic reaction of an olefin with carbon monoxide and hydrogen. The reaction occurs at temperatures in the order of 300400 F., at pressures in the range of about 1000 to 3000 p. s. i., in the presence of a suitable catalyst, ordinarily a heavy metal carbonyl such as cobalt carbonyl.
  • the resulting aldehyde is subsequently hydrogenated to a primary alcohol. This process is described in U. S. Patent No. 2,327,066 issued to Roelen in 1943.
  • phosphoric acid catalysts such as phosphoric acid or copper phosphate impregnated on silica gel, sulfuric acid, Friedel- Crafts catalysts, activated clays, silica-alumina, copper pyrophosphate, etc.
  • Suitable conditions when employing phosphoric acid catalysts of the U. 0. P. type are temperatures of 300 F. to 500 F., pressures from 250 to 5,000 p. s. i. and feed stocks comprising refinery streams containing propylene and mixed butylenes.
  • Suitable feed stocks for example, may contain from to 60 mol percent propylenes, from 0.5 to 15 mol percent butylenes, and from 0.1 to 10 mol percent isobutylene, the remaining being saturated hydrocarbons.
  • Other suitable feed stocks are the dimer and trimer of isobutylene.
  • the prefenred Ox'o alcohols employed in forming the formals of this invention are those having from 8 to carbon atoms derived from olefin copolymers having from 7 to 19 carbon atoms.
  • the desired olefin fraction is segregated from the crude olefin polymer product by fractionation.
  • the following table shows the structure and percent composition of Ca OX0 alcohols prepared from a. C7 olefin stream which had been fractionated from the products obtained by the phosphoric acid polymerization of refinery gas streams containing propylene and mixed nand isobutylenes.
  • complex form'als may be considered to have the following general formula:
  • a and B represent radicals derived from organic compounds by removal of one reacting h'y'droxyl group.
  • x and n are 2 or more and y is one or more.
  • the radicals represented by A and -B may be alike or different and may contain fromxl to 60' carbon atoms. The sum of the carbon atoms in -the molecule should be between 20 and 130 and .pre'ferablyzbetween about and 100. 1.
  • the grou of organic compounds that satisfy th'eeonditions of the above generic formula and that are used to build the preferred compounds according to the concept of this invention are monohydric alcohols, glycols, and organic acids. These compounds may be advantageously combined with formaldehyde to form molecules having the following type formulas, words instead of structures being given to show the components of the complex formals.
  • glycol monoester-(formaldehyde-glycol) a Glycol monoeth'e'r-(formaldehyde-glycol)m
  • x represents a Whole number greater than 11.
  • the acids which may be used to prepare the glycol monoesters may be selected from the following partial list:
  • n-ctin ocrncHz 2ocuzocsneocansocgneonn
  • the hemiformal of n-butyl Carbitol was made by heating 81.1 g. /z mole) of the Carbitol with 15.1 g. /2 mole CH2O) of paraformaldehyde, 200 g. of heptane and 2 g. of NaHSO4 at 65 C. for half an hour.
  • a and B may be the same or diiferent and are selected from the group consisting of organic radicals containing from 1 to 60 carbon atoms which corresponds to organic compounds containing a hydroxyl group that is alcoholic in nature and wherein x and n are whole numbers greater than 1 and y is 1 or more.
  • the reaction product was decanted from the catalyst and then washed with 150 cc. of NazCOa solution and finally with two 100 cc. portions of water. The material was then stripped free of the solvent and light ends.
  • the material boiling above 152 C. at 0.3 mm. pressure and consisting of the 14100% fraction had the following proper-ties:
  • the material obtained boiling above 161 C. at 0.3 mm. had the following properties:
  • This product was purified in the manner similar to that of Example VI above and stripped to 210 C. vapor temperature at 9.0 mm. pressure.
  • This product had the following properties:
  • the complex formals as describedherein may serve as the lubricant base for grease compositions.
  • These syntheticlubricants may be thickened to stable grease structures with conventional grease forming soaps such as lithium soaps of high molecular weightsubstantially saturated fatty acid, the n-acyl p am'ino phenols, silica gels, treated bentinites and the like. Oxidation inhibitors, rust inhibitors, tackiness agents and other grease addition agents may be added to the complex formal greases.
  • the soap complexes known to the artmade by using low molecular weight acid salts may also be used in preparing these grease compositions.
  • the complex formals of this invention may be blended with mineral oil or other synthetic lubricants such as simple bis-formals, complex esters, di-esters, phosphates, siloxanes, silicates, phosphonates and the like and a grease composition which incorporates the desirable characteristics of the blends may be prepared by conventional techniques.
  • mineral oil or other synthetic lubricants such as simple bis-formals, complex esters, di-esters, phosphates, siloxanes, silicates, phosphonates and the like and a grease composition which incorporates the desirable characteristics of the blends may be prepared by conventional techniques.
  • this invention relates to new compositions of matter which have outstanding utility as synthetic lubricating compositions.
  • the materials contemplated may be broadly described as being complex formals of organic materials containing at least one hydroxyl group that is alcoholic in nature.
  • complex formal is meant materials containing more than 2 formal linkages.
  • the structure of the formals of invention may be described as one corresponding to the formula:
  • a and B are organic radicals containing from 1 to 60 carbon atoms which are derived from organic materials containing at least one hydroxyl group that is alcoholic in nature.
  • a and B may be alike or different and the total number of carbon atoms in the molecule should be between about 20 and 130, preferably between about 25 and 100.
  • the compounds that are especially preferred and that are considered to be the preferred embodiment of this invention are those materials that have a kinematic viscosity at 210 F. within the range of from 2 to 60 centistokes, an ASTM pour point of at least as low as 35 F., and a flash point of at least 300 F.
  • solubilizers grease bases, insecticides, weed killers, rust preventives, solvents, .dewaxing aids, detergents, and as raw materials for many other industrial applications, such as household -detergents, fumigants, etc.
  • These new synthetic lubricating oils may be admixed with other lubricating oils, naturally occurring or synthetic, either as concentratesor as finished blends. They are compatible and may bev blended with the well known lubricant addition agents such as viscosity index improvers, pour point depressors, detergents, rust inhibitors, antioxidants, and the like.
  • a complex formal having an ASTM pour point below about 35 F., a flash point above about 300 F., and a kinematic viscosity at 210 F. within the range of from 2 to 60 centistokes, said formal corresponding to the formula wherein A and B are selected from the group consisting of hydrocarbon and substituted hydrocarbon radicals containing from 1 to 60 carbon atoms wherein at and n are integers having a value of at least 2 and y is an integer having a value of at least 1, the total number of carbon atoms in the molecule being between and 130.
  • a synthetic lubricant according to claim 1 wherein A is derived from monohydric alcohol and wherein B is derived from a glycol.
  • a complex formal having the formula wherein A and B are organic radicals derived from C8 to C20 alcohols and wherein x and n are numbers having the value of 2 or more and y is an integer having a value of at least 1, said formal being formed by reacting together x.y moles of a glycol with x-I-l moles of formaldehyde and 2 moles of an alcohol containing from 8 to 20 carbon atoms, said formal having an ASTM pour point below about +35 F., a flash point above about 300 F., and a viscosity at 210 F. within the range of from 2 to 60 centistokes, the total number of carbon atoms in the molecule being between about to 100.
  • a synthetic lubricant according to claim 4 wherein said glycol is tripropylene glycol.
  • a synthetic lubricant according to claim 4 wherein said alcohol is a highly branchedchain aliphatic alcohol of 13 carbon atoms alcohol and wherein x, n, and y are 3.
  • a synthetic lubricant according to claim 4 wherein said alcohol is an ether alcohol, wherein said glycol is a polypropylene glycol of a molecular weight of about 150 and wherein x is 2.
  • a synthetic lubricant according to claim 4 having an ASTM pour point of below l5 F., a flash point in excess of 350 F. and viscosity at 210 F. of from 2.6 to 13.0 centistokes.
  • a complex formal of the formula wherein A and B are selected from the group consisting of hydrocarbon and substituted hydrocarbon radicals containing from 1 to carbon atoms and wherein x and n are numbers having the value of at least 2 and wherein y is a number of at least 1 thickened to a grease consistency with a lithium soap of a high molecular weight fatty acid, said complex formal having an ASTM pour point below about +35 F., a flash point above about 300 F., and a viscosity at 210 F. within the range of from 260 centistokes, the total number of carbon atoms in said formal being between about 20 to 130.

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  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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US323338A 1952-11-29 1952-11-29 Complex formal lubricating composition Expired - Lifetime US2796401A (en)

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US323338A US2796401A (en) 1952-11-29 1952-11-29 Complex formal lubricating composition
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3005774A (en) * 1957-07-29 1961-10-24 Exxon Research Engineering Co Lubricants containing cross-linked polymers as thickening agents
US3205269A (en) * 1960-05-10 1965-09-07 Union Carbide Corp Stabilization of ethers with phosphorous compounds
US3231604A (en) * 1962-01-23 1966-01-25 Du Pont Polyethylene oxide and polypropylene oxide perfluoroalkyl substituted oxyalkanoates
US3249543A (en) * 1963-04-30 1966-05-03 Monsanto Res Corp Lubricant composition containing a rhodanine compound
US3392118A (en) * 1966-06-09 1968-07-09 Sinclair Research Inc Formal of diene polymer containing terminal hydroxyl groups and mineral oil containing same
US3435077A (en) * 1965-01-16 1969-03-25 Huels Chemische Werke Ag Process for the production of asymmetrical formals
US3875197A (en) * 1968-07-15 1975-04-01 Hoechst Ag Amido-methyl-polyglycol formals
US3900411A (en) * 1973-11-19 1975-08-19 Mobil Oil Corp Lubricant compositions containing acetal or ketal detergents
US4093666A (en) * 1974-02-06 1978-06-06 Hoechst Aktiengesellschaft Process for the manufacture of glycol ether formals
US4189609A (en) * 1974-08-19 1980-02-19 Basf Wyandotte Corporation Multi-block coupled polyoxyalkylene copolymer surfactants
US4408084A (en) * 1981-01-09 1983-10-04 Basf Wyandotte Corporation Non-ionic surfactants containing acetal groups
US5744065A (en) * 1995-05-12 1998-04-28 Union Carbide Chemicals & Plastics Technology Corporation Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water
US5744064A (en) * 1995-05-12 1998-04-28 Union Carbide Chemicals & Plastics Technology Corporation Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1059599B (de) * 1953-05-28 1959-06-18 Exxon Research Engineering Co Synthetische Schmiermittel
DE1121759B (de) * 1954-03-17 1962-01-11 Exxon Research Engineering Co Synthetisches Schmiermittel

Citations (6)

* Cited by examiner, † Cited by third party
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US2350350A (en) * 1941-05-06 1944-06-06 Du Pont Glycol formals
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US3005774A (en) * 1957-07-29 1961-10-24 Exxon Research Engineering Co Lubricants containing cross-linked polymers as thickening agents
US3205269A (en) * 1960-05-10 1965-09-07 Union Carbide Corp Stabilization of ethers with phosphorous compounds
US3231604A (en) * 1962-01-23 1966-01-25 Du Pont Polyethylene oxide and polypropylene oxide perfluoroalkyl substituted oxyalkanoates
US3249543A (en) * 1963-04-30 1966-05-03 Monsanto Res Corp Lubricant composition containing a rhodanine compound
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US3392118A (en) * 1966-06-09 1968-07-09 Sinclair Research Inc Formal of diene polymer containing terminal hydroxyl groups and mineral oil containing same
US3875197A (en) * 1968-07-15 1975-04-01 Hoechst Ag Amido-methyl-polyglycol formals
US3900411A (en) * 1973-11-19 1975-08-19 Mobil Oil Corp Lubricant compositions containing acetal or ketal detergents
US4093666A (en) * 1974-02-06 1978-06-06 Hoechst Aktiengesellschaft Process for the manufacture of glycol ether formals
US4189609A (en) * 1974-08-19 1980-02-19 Basf Wyandotte Corporation Multi-block coupled polyoxyalkylene copolymer surfactants
US4408084A (en) * 1981-01-09 1983-10-04 Basf Wyandotte Corporation Non-ionic surfactants containing acetal groups
US5744065A (en) * 1995-05-12 1998-04-28 Union Carbide Chemicals & Plastics Technology Corporation Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water
US5744064A (en) * 1995-05-12 1998-04-28 Union Carbide Chemicals & Plastics Technology Corporation Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water
US5851434A (en) * 1995-05-12 1998-12-22 Union Carbide Chemicals & Plastics Technology Corporation Ketone-based surfactant and method for treating industrial, commercial, and institutional waste-water
US5919372A (en) * 1995-05-12 1999-07-06 Union Carbide Chemicals & Plastics Technology Corporation Aldehyde-based surfactant and method for treating industrial commercial and institutional waste-water
US6051035A (en) * 1995-05-12 2000-04-18 Union Carbide Chemicals & Plastics Technology Corporation Methods of cleaning fabrics with splittable aldehyde-based surfactants
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DE961483C (de) 1957-04-04
NL89229C (OSRAM)

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