GB729376A - Improvements in or relating to the preparation of basic metallic compounds of phenols - Google Patents

Improvements in or relating to the preparation of basic metallic compounds of phenols

Info

Publication number
GB729376A
GB729376A GB11619/53A GB1161953A GB729376A GB 729376 A GB729376 A GB 729376A GB 11619/53 A GB11619/53 A GB 11619/53A GB 1161953 A GB1161953 A GB 1161953A GB 729376 A GB729376 A GB 729376A
Authority
GB
United Kingdom
Prior art keywords
alkyl
salicylates
mixture
phenolates
metal
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
GB11619/53A
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.)
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 GB729376A publication Critical patent/GB729376A/en
Expired legal-status Critical Current

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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/028—Overbased 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • 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

Landscapes

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

Abstract

A mixture of metal alkyl phenolates and metal alkyl salicylates, containing a polyvalent metal, suitable for use as a lubricating oil additive and having a basicity (defined as being the excess of polyvalent metal content over that theoretically required to convert the alkali metal salicylates used as a starting material to the corresponding neutral salt, expressed as a percentage), of more than 50 per cent, is made by reacting a mixture of alkali metal salts of alkyl salicylic acids and alkali metal compounds of alkyl phenols with an inorganic polyvalent metal salt in an amount which is at least equivalent to the alkali metal content of the original mixture and an oxide or hydroxide of the polyvalent metal in an amount which is greater than the theoretical quantity required for the formation of a product having a basicity of 50 per cent. The polyvalent metal is preferably an alkaline earth metal or magnesium and the polyvalent metal salt is preferably a halide or nitrate, e.g. calcium chloride. Suitably the mixture of alkali metal alkyl phenolates and alkyl salicylates is treated with calcium chloride in solution in an alcohol of 1-3 carbon atoms, e.g. ethyl or methyl alcohol which may contain up to 10 per cent of water and with a suspension of calcium oxide or hydroxide in alcohol which may conveniently be obtained by adding an alcoholic solution of sodium or potassium hydroxide to an excess of the alcoholic solution of calcium chloride. The reaction may be carried out for 1-4 hours at a temperature of 70-110 DEG C. and the alcohol may be allowed to distil off during the reaction. The reaction product is separated from inorganic compounds by filtering and washing with water or aqueous alcohol. Preferred products are obtained by using alkali metal, alkyl phenolates and salicylates in which the alkyl groups have from 8-20 carbon atoms. In examples a mixture of 75 mol. per cent of sodium mono- and di-alkyl salicylates and 25 mol. per cent of sodium mono- and di-alkyl phenolates in which the alkyl groups contain 14-18 carbon atoms is diluted with xylene, a solution of calcium chloride in 96 per cent ethyl alcohol is added followed by calcium oxide, and the reaction mixture is heated while allowing the alcohol to distil off, the product is diluted with petroleum filtered, and the diluent is distilled off to give the desired product. A mixture of alkyl salicylates and alkyl phenolates suitable for use as a starting material is obtained by treating alkali metal alkyl phenolates with sufficient carbon dioxide to partially convert the phenolate to a salicylate.ALSO:Lubricating oil compositions comprise a major proportion of a lubricating oil and a minor proportion, e.g. 0.1 per cent. to 15 per cent. by weight, of a mixture of metal alkyl phenolates and metal alkyl salicylates, made by reacting alkali metal salts of alkyl phenols and alkyl salicylates with an inorganic polyvalent metal salt and an inorganic metal oxide or hydroxide (see Group IV (b)) characterized in that the basicity of the mixture of phenolates and salicylates (defined as being the excess of polyvalent metal content over that theoretically required to give the neutral salt of the alkyl salicylic acid, expressed as a percentage) is more than 50 per cent. In examples lubricating oil compositions are described comprising lubricating oils admixed with a mixture of metal alkyl salicylates and phenolates obtained by reacting mixed sodium alkyl salicylates and alkyl phenolates wherein the alkyl groups contain 14-18 carbon atoms with calcium chloride and calcium hydroxide.
GB11619/53A 1952-04-29 1953-04-27 Improvements in or relating to the preparation of basic metallic compounds of phenols Expired GB729376A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL729376X 1952-04-29

Publications (1)

Publication Number Publication Date
GB729376A true GB729376A (en) 1955-05-04

Family

ID=19817915

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11619/53A Expired GB729376A (en) 1952-04-29 1953-04-27 Improvements in or relating to the preparation of basic metallic compounds of phenols

Country Status (5)

Country Link
BE (2) BE519501A (en)
DE (2) DE1016272B (en)
FR (2) FR1079237A (en)
GB (1) GB729376A (en)
NL (2) NL77097C (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6153565A (en) * 1996-05-31 2000-11-28 Exxon Chemical Patents Inc Overbased metal-containing detergents
US6417148B1 (en) 1996-05-31 2002-07-09 Infineum Usa L.P. Overbased metal-containing detergents
US6429178B1 (en) 1996-05-31 2002-08-06 Infineum Usa L.P. Calcium overbased metal-containing detergents
US6429179B1 (en) 1996-05-31 2002-08-06 Infineum U.S.A. L.P. Calcium overbased metal-containing detergents
EP1229101A1 (en) * 2001-02-06 2002-08-07 Infineum International Limited Marine diesel engine lubricant
EP1229102A1 (en) * 2001-02-06 2002-08-07 Infineum International LTD Lubricating oil composition
WO2005108339A2 (en) 2004-05-06 2005-11-17 Osteologix A/S High yield and rapid syntheses methods for producing metallo-organic salts
US8541471B2 (en) 2003-05-07 2013-09-24 Osteologix A/S Water-soluble strontium salts for use in treatment of cartilage and/or bone conditions
US8623422B2 (en) 2003-05-07 2014-01-07 Osteologix A/S Combination treatment with strontium for the prophylaxis and/or treatment of cartilage and/or bone conditions

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1304289A (en) * 1970-09-14 1973-01-24
US3755170A (en) * 1971-05-17 1973-08-28 Continental Oil Co Preparation of highly basic alkylphenates and sulfurized alkyphenates
US5259966A (en) * 1992-11-10 1993-11-09 The Lubrizol Corporation Low chlorine overbased calcium salts
JPH07268374A (en) * 1994-03-30 1995-10-17 Cosmo Sogo Kenkyusho:Kk Petroleum additive and production of alkaline earth metallic salt of aromatic hydroxycarboxylic acid

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6153565A (en) * 1996-05-31 2000-11-28 Exxon Chemical Patents Inc Overbased metal-containing detergents
US6417148B1 (en) 1996-05-31 2002-07-09 Infineum Usa L.P. Overbased metal-containing detergents
US6429178B1 (en) 1996-05-31 2002-08-06 Infineum Usa L.P. Calcium overbased metal-containing detergents
US6429179B1 (en) 1996-05-31 2002-08-06 Infineum U.S.A. L.P. Calcium overbased metal-containing detergents
US6645922B2 (en) 2001-02-06 2003-11-11 Infineum International Ltd. Lubrication
EP1229102A1 (en) * 2001-02-06 2002-08-07 Infineum International LTD Lubricating oil composition
EP1229101A1 (en) * 2001-02-06 2002-08-07 Infineum International Limited Marine diesel engine lubricant
SG105535A1 (en) * 2001-02-06 2004-08-27 Infineum Int Ltd Lubrication
US8541471B2 (en) 2003-05-07 2013-09-24 Osteologix A/S Water-soluble strontium salts for use in treatment of cartilage and/or bone conditions
US8623422B2 (en) 2003-05-07 2014-01-07 Osteologix A/S Combination treatment with strontium for the prophylaxis and/or treatment of cartilage and/or bone conditions
WO2005108339A2 (en) 2004-05-06 2005-11-17 Osteologix A/S High yield and rapid syntheses methods for producing metallo-organic salts
WO2005108339A3 (en) * 2004-05-06 2005-12-29 Osteologix As High yield and rapid syntheses methods for producing metallo-organic salts
US7589235B2 (en) 2004-05-06 2009-09-15 Osteologix, A/S High yield and rapid synthesis methods for producing metallo-organic salts
US8183409B2 (en) 2004-05-06 2012-05-22 Osteologix A/S High yield and rapid synthesis methods for producing metallo-organic salts

Also Published As

Publication number Publication date
DE1039069B (en) 1958-09-18
FR68753E (en) 1958-06-10
NL81942C (en)
BE532864A (en)
NL77097C (en)
DE1016272B (en) 1957-09-26
BE519501A (en)
FR1079237A (en) 1954-11-26

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