GB684155A - Manufacture of metal salts of organic acids - Google Patents

Manufacture of metal salts of organic acids

Info

Publication number
GB684155A
GB684155A GB16356/49A GB1635649A GB684155A GB 684155 A GB684155 A GB 684155A GB 16356/49 A GB16356/49 A GB 16356/49A GB 1635649 A GB1635649 A GB 1635649A GB 684155 A GB684155 A GB 684155A
Authority
GB
United Kingdom
Prior art keywords
acid
acids
calcium
alkyl
phenate
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
GB16356/49A
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.)
California Research LLC
Original Assignee
California Research LLC
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 California Research LLC filed Critical California Research LLC
Publication of GB684155A publication Critical patent/GB684155A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
    • C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
    • 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
    • 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
    • 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
    • C10M2203/104—Aromatic fractions
    • 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
    • C10M2203/106—Naphthenic fractions
    • 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
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • 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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • 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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • 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
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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

Abstract

Polyvalent metal salts of phenols, carboxylic acids and organo-substituted acids of phosphorus are obtained by reacting the phenol or acid with a polyvalent metal basic compound in the presence of a polyhydric alcohol. The latter is used in sufficient amount to cause substantial contact between the reactants, e.g. from 0.2 to 10.0 (preferably 0.75 to 2.0) times the weight of phenol or acid. In the preferred method the basic compound is dispersed in the polyhydric alcohol and then contacted with the phenol or acid; the water of reaction is then removed with or without some polyhydric alcohol. A higher-boiling liquid such as a mineral oil is then added and the remainder of the alcohol removed and, if desired, recycled. Suitable alcohols are ethylene glycol, propylene glycol, butanediol-2 : 3, pentanediols-2 : 3 and 2 : 4, 2-methylbutanediols-1 : 3, 2 : 4 and 3 : 4, and glycerol. Suitable basic compounds are the oxides and hydroxides of magnesium, calcium, barium, strontium, lead and thallium. Examples show the production of calcium "alkyl"-phenate, barium "alkyl"-phenate, calcium p-tert-amyl-phenate, lead "lkyl"-phenate and magnesium "lkyl"-phenate, the products being obtained as solutions in mineral oils and in some cases are further reacted with sulphur to produce lubricating oil additives. The "alkyl"-phenol used was a mixture where the side-chains contained 14-16 carbon atoms. Samples have been furnished under Sect. 2 (5) of (1) calcium stearate, (2) a mixture of calcium mono- and di-cetyl phosphates, (3) calcium O : O-dibutyldithiophosphate, and (4) calcium "white oil" phosphonate, prepared by the method of the invention. The acidic starting materials are of the formula RX, where R is an organic radical and may be aliphatic, alicyclic, aromatic or aralkyl, and X is a phenolic hydroxyl group, a carboxylic acid group or the residue of a phosphorus-containing acid. Thus RX may be ethylphenol, tert-amylphenol, octylphenol, dodecylphenol, cetylphenol, caproic acid, stearic acid, palmitic acid, naphthenic acid, mono- and di-cetylphosphoric acids, cetane phosphonic acid and its monoethyl ester, dicetylphosphinic acid, dicetyl phosphite, dicetylphosphinous acid, cetane phosphonous acid and its monobutyl ester and sulphur and selenium derivatives of these. According to the Specification as open to inspection under Sect. 91, X in the above formula may be any group containing an acidic hydrogen atom. In addition to the above there are specified mercaptans, hydroselenides, sulphuric acid monoesters, sulphonic acids (e.g. dodecane sulphonic acid), sulphinic acids (e.g. dicetylsulphinic acid-sic-), arsonic acids (dodecane arsonic acid), arsinic acids (dilaurylarsinic acid), arsenic acid esters (mono- and di-cetyl), arsonous acids (octane arsonous acid) and their monoesters, arsenous acid esters, boric acid esters, boronic acids (cetane boronic acid), borinic acids (dicetylborinic acid) and esters and sulphur and selenium derivatives of these. A further example is given of the preparation of calcium "alkyl"-benzene sulphonate, the side-chain having 14-16 carbon atoms (mixture). This subject-matter does not appear in the Specification as accepted.ALSO:Lubricating oil additives are made by reacting a polyvalent metal basic compound with a phenol, carboxylic acid or organo-substituted phosphorus acid in the presence of a polyhydric alcohol, adding a mineral oil and removing the polyhydric alcohol and water of reaction. The product may be sulphurized if desired. Examples show the production of mineral oil solutions of calcium "alkyl"-phenate, barium "alkyl"-phenate, calcium p-tert-amylphenate, lead "alkyl"-phenate and magnesium "alkyl"-phenate, with or without sulphurization. The "alkyl"-phenol used was a mixture where the side-chains contained 14-16 carbon atoms. Other specified metals are strontium and thallium. Samples have been furnished under Sect. 2 (5) of calcium stearate, a mixture of calcium mono- and di-cetyl phosphates, calcium O:: O-dibutyldithiophosphate and calcium "white oil" phosphonate. The process is stated to be applicable also to phosphinic acids, phosphite partial esters, phosphinous acids, phosphorous acids and partial esters and p sulphur and selenium derivatives of phosphorus acids. According to the Specification as open to inspection under Sect. 91, the process may be applied to mercaptans, hydroselenides, sulphuric acid monoesters, sulphonic acids, sulphinic acids and organic derivatives of arsenic and boron acids, a list of such being given. A further example is given of the production of a mineral oil solution of calcium "alkyl"-benzene sulphonate, the alkyl group having 14-16 carbon atoms. This subject-matter does not appear in the Specification as accepted.
GB16356/49A 1948-07-03 1949-06-20 Manufacture of metal salts of organic acids Expired GB684155A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US684155XA 1948-07-03 1948-07-03

Publications (1)

Publication Number Publication Date
GB684155A true GB684155A (en) 1952-12-10

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Family Applications (1)

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GB16356/49A Expired GB684155A (en) 1948-07-03 1949-06-20 Manufacture of metal salts of organic acids

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2935485A (en) * 1956-06-28 1960-05-03 Shell Oil Co Oil extended rubber compositions stabilized with magnesium salts
GB2126602A (en) * 1982-08-16 1984-03-28 Maruzen Oil Co Ltd Process for the production of basic alkaline earth metal phenates
EP0184129A1 (en) * 1984-12-05 1986-06-11 NEYNABER CHEMIE GmbH Process for the preparation of dibasic lead (II) salts of fatty acids by the fusion process
EP0184128A1 (en) * 1984-12-05 1986-06-11 NEYNABER CHEMIE GmbH Process for the preparation of mixtures of neutral and dibasic lead (II) salts of fatty acids by the fusion process
WO1987000520A1 (en) * 1985-07-26 1987-01-29 General Electric Company Method for neutralization of organophilic acidic compounds
US4700000A (en) * 1982-04-28 1987-10-13 Basf Aktiengesellschaft Preparation of calcium propionate
CN103739536A (en) * 2013-12-04 2014-04-23 温州大学 Diaryl diselenide compound synthesis method

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2935485A (en) * 1956-06-28 1960-05-03 Shell Oil Co Oil extended rubber compositions stabilized with magnesium salts
US4700000A (en) * 1982-04-28 1987-10-13 Basf Aktiengesellschaft Preparation of calcium propionate
GB2126602A (en) * 1982-08-16 1984-03-28 Maruzen Oil Co Ltd Process for the production of basic alkaline earth metal phenates
EP0184129A1 (en) * 1984-12-05 1986-06-11 NEYNABER CHEMIE GmbH Process for the preparation of dibasic lead (II) salts of fatty acids by the fusion process
EP0184128A1 (en) * 1984-12-05 1986-06-11 NEYNABER CHEMIE GmbH Process for the preparation of mixtures of neutral and dibasic lead (II) salts of fatty acids by the fusion process
US4744927A (en) * 1984-12-05 1988-05-17 Henkel Kommanditgesellschaft Auf Aktien Synthesis of dibasic organo-lead compounds in melt phase
US4767575A (en) * 1984-12-05 1988-08-30 Neynaber Chemie Gmbh Melt-phase synthesis of dibasic organo-lead compounds
WO1987000520A1 (en) * 1985-07-26 1987-01-29 General Electric Company Method for neutralization of organophilic acidic compounds
CN103739536A (en) * 2013-12-04 2014-04-23 温州大学 Diaryl diselenide compound synthesis method
CN103739536B (en) * 2013-12-04 2015-07-01 温州大学 Diaryl diselenide compound synthesis method

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