GB632990A - A process for the preparation of a product suitable for use as a lubricant, an addition to a lubricant, or capable of being used in the preparation of a lubricant or an addition to a lubricant - Google Patents

A process for the preparation of a product suitable for use as a lubricant, an addition to a lubricant, or capable of being used in the preparation of a lubricant or an addition to a lubricant

Info

Publication number
GB632990A
GB632990A GB11339/46A GB1133946A GB632990A GB 632990 A GB632990 A GB 632990A GB 11339/46 A GB11339/46 A GB 11339/46A GB 1133946 A GB1133946 A GB 1133946A GB 632990 A GB632990 A GB 632990A
Authority
GB
United Kingdom
Prior art keywords
polymerization
alkylation
mixture
alkylated
catalyst
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
GB11339/46A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB632990A publication Critical patent/GB632990A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/02—Alkylation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
    • 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
    • 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
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • 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
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    • 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
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    • 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
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2209/082—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 monocarboxylic
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/043—Mannich bases
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    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2223/04—Phosphate esters
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2010/14—Group 7
    • 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
    • C10N2010/16—Groups 8, 9, or 10

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The process of the parent Specification (in which a product suitable for use as a lubricant or lubricant additive is prepared by subjecting a mixture of a polar aromatic compound and an excess of compounds with one or more double bonds and containing more than four carbon atoms to simultaneous alkylation and polymerization) is modified in that the alkylation and polymerization treatments are carried out successively (in either order) instead of simultaneously. Examples are given in which phenol, an octylphenol and salicylic acid are treated with a mixture of olefines obtained by cracking a paraffin wax distillate.ALSO:The process of the parent Specification (in which aromatic compounds containing one or more polar groups together with an excess of compounds with one or more aliphatic double bonds and containing more than four carbon atoms in the molecule are subjected to a simultaneous alkylation and polymerization treatment) is modified in that the alkylation and polymerization treatments are carried out successively (in either order) instead of simultaneously. The aromatic compound may first be alkylated and the alkylation may then be continued while simultaneously polymerizing, or the olefinic compound may first be polymerized and then the aromatic compound may be alkylated, while at the same time continuing the polymerization. In an example, one mol. of phenol is alkylated with 1.5 mol. of di-isobutylene at a temperature of 100 DEG C. using 3 per cent by weight of concentrated sulphuric acid as a catalyst. The reaction product is mixed with two mols. of a fraction of a cracked paraffin wax distillate with a boiling range of from 30-150 DEG C., and composed of a mixture of C5-C10 hydrocarbons in which the olefines present are mono-olefines, and a polymerization and alkylation reaction is effected by maintaining the reaction mixture for 2 hours at a temperature of 60 DEG C., using 3 per cent by weight of aluminium chloride as a catalyst. Only the 2, 4 and 6 positions of phenol are said to be alkylatable when aluminium chloride or boron fluoride is used as catalyst and the alkyl groups contain more than four carbon atoms. An example is given also of the treatment of salicylic acid with a similar olefine mixture.ALSO:The process of the parent Specification (in which aromatic compounds containing one or more polar groups, together with an excess of compounds with one or more aliphatic double bonds and containing more than four carbon atoms in the molecule, are subjected to a simultaneous alkylation and polymerization treatment) is modified in that the alkylation and polymerization are carried out successively (in either order) instead of simultaneously. The aromatic compound may first be alkylated and the alkylation may then be continued while simultaneously polymerizing, or the olefine may first be polymerized and then the aromatic compound may be alkylated, while at the same time continuing the polymerization. In an example, one mol. of phenol is alkylated with 1.5 mol. of diisobutylene, at a temperature of 100 DEG C., using 3 per cent by weight of concentrated sulphuric acid as a catalyst. The reaction product is mixed with two mols. of a mixture of C5-C10 hydrocarbons containing monolefines and a polymerization and alkylation reaction is effected by maintaining the reaction mixture for 2 hours at a temperature of 60 DEG C., using 3 per cent by weight of aluminium chloride as catalyst. Only the 2-, 4-and 6-positions of phenol are said to be alkylatable when aluminium chloride or boron fluoride is used as a catalyst and the alkyl groups contain more than four carbon atoms. An example is given also of the treatment of salicylic acid with a similar olefine mixture.
GB11339/46A 1945-07-31 1946-04-12 A process for the preparation of a product suitable for use as a lubricant, an addition to a lubricant, or capable of being used in the preparation of a lubricant or an addition to a lubricant Expired GB632990A (en)

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Application Number Priority Date Filing Date Title
NL120645A NL65636C (en) 1945-07-31 1945-07-31

Publications (1)

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GB632990A true GB632990A (en) 1949-12-05

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GB4251/46A Expired GB625104A (en) 1945-07-31 1946-02-11 A process for the preparation of a product suitable for use as a lubricant, an addition to a lubricant, or capable of being used in the preparation of a lubricant or an addition to a lubricant
GB11339/46A Expired GB632990A (en) 1945-07-31 1946-04-12 A process for the preparation of a product suitable for use as a lubricant, an addition to a lubricant, or capable of being used in the preparation of a lubricant or an addition to a lubricant

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GB4251/46A Expired GB625104A (en) 1945-07-31 1946-02-11 A process for the preparation of a product suitable for use as a lubricant, an addition to a lubricant, or capable of being used in the preparation of a lubricant or an addition to a lubricant

Country Status (5)

Country Link
US (1) US2483859A (en)
DE (2) DE832313C (en)
FR (1) FR929275A (en)
GB (2) GB625104A (en)
NL (1) NL65636C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4320021A (en) 1975-10-14 1982-03-16 The Lubrizol Corporation Amino phenols useful as additives for fuels and lubricants
US5207940A (en) * 1990-09-12 1993-05-04 Ethyl Corporation α-olefin oligomer-phenol lubricant oil adducts
US5225588A (en) * 1992-02-03 1993-07-06 Ethyl Corporation Process for alkylating salicylates with polyalphaolefin

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108264892A (en) * 2017-12-21 2018-07-10 东北农业大学 A kind of composition for the surfactant for being used to discharge underground oily material

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2197837A (en) * 1936-08-29 1940-04-23 Socony Vacuum Oil Co Inc Mineral oil composition
US2228671A (en) * 1938-10-04 1941-01-14 Standard Oil Co Compounded mineral oil
US2228661A (en) * 1938-10-08 1941-01-14 Standard Oil Co Compounded oil
NL50248C (en) * 1938-12-05 1941-04-15
US2347546A (en) * 1940-12-07 1944-04-25 Sinclair Refining Co Lubricating oil composition
US2324784A (en) * 1941-01-02 1943-07-20 Standard Oil Dev Co Condensation product and method of preparing and using same
US2347547A (en) * 1941-08-15 1944-04-25 Sinclair Refining Co Lubricating oil composition
US2356685A (en) * 1943-06-14 1944-08-22 Standard Oil Co California Compounded oils

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4320021A (en) 1975-10-14 1982-03-16 The Lubrizol Corporation Amino phenols useful as additives for fuels and lubricants
US5207940A (en) * 1990-09-12 1993-05-04 Ethyl Corporation α-olefin oligomer-phenol lubricant oil adducts
US5225588A (en) * 1992-02-03 1993-07-06 Ethyl Corporation Process for alkylating salicylates with polyalphaolefin

Also Published As

Publication number Publication date
GB625104A (en) 1949-06-22
FR929275A (en) 1947-12-22
DE865927C (en) 1953-02-05
DE832313C (en) 1952-02-21
US2483859A (en) 1949-10-04
NL65636C (en) 1950-05-15

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