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 Table
  • 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
• • 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
  • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
  • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
• • 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
  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
  • C10M137/10—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
  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/06—Metal compounds
  • C10M2201/065—Sulfides; Selenides; Tellurides
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
• • 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
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
  • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
• • 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
  • 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
  • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy 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
  • C10M2207/10—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
• • 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
  • C10M2207/16—Naphthenic 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
  • 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
  • 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
  • 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
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• the invention relates to improved lubricating oil compositions. More specifically, it relates to lubricating oil compositions which are substantially non-corrosive to silver.
• zinc bis(alkyl)dithiophosphates other than those derived 7 from neo-type alcohols, are not made non-corrosive to silver by reaction thereof with zinc carboxylates.
• the manner in which the zinc dithiophosphate and zinc .carboxylate salts are combined in the reaction -of the invention is not known with certainty, it is theorized, without wishing to limit the invention in any way, that they are joined by coordinate bonds similar to those existing in complexes of the Werner-type.
• the product salts are referred to herein as zinc carboxylate-coordinated zinc dithiophosphate salts.
• the zinc carboxylate-coordinated zinc dithiophosphate salts contemplated by the invention have not been known heretofore and they are, therefore, believed to be new compositions of matter. Accordingly, it is the primary object of the invention to provide a new class of zinc dithiophosphate salts which are non-corrosive to silver, viz., zinc carboxylate-coordinated zinc dithiophosphate salts. A further object is to provide lubricating oil compositions containing these new coordinated salts. Other and further objects of the invention will be apparent from the following detailed description.
• the zinc carboxylate-coordinated zinc dithiophosphate salts are produced by l) forming a reaction mixture of '(A) one mol 3,162,096 Patented Aug. 27, 1963 proportion of Zll'lC dithiophosphate, -(B) at least one mol proportion of zinc carboxylate, (C) water and (D) a hydrocarbon solvent and (2) heating the mixture to a temperature sufficient to distill off the water, whereby a solvent solution of the zinc carboxylate-coordinated zinc dithiophosphate salt, containing approximately one mol proportion of each of the reactant salts, is produced. The product mixture is then filtered to remove any unreacted salt.
• a light hydrocarbon solvent such as xylene, toluene or a petroleum naphtha
• the water distilled off as an azeotropic mixture with the solvent.
• a lubricating oil may be added to the solvent mixture and the remainder of the solvent distilled off (or the solvent can be removed before the oil is added) whereby a lubricating oil concentrate of the product salt, suitable for blending with the base lubricating oil, is obtained.
• normal zinc bis(aryl)dithiophosphates to which the invention is applicable are those containing aryl radicals, such as phenyl, naphthyl or the like, which radicals may have one or more (up to 5) alkyl groups of from one up to about 20 carbon atoms substituted thereon
• aryl radicals such as phenyl, naphthyl or the like
• radicals may have one or more (up to 5) alkyl groups of from one up to about 20 carbon atoms substituted thereon
• normal zinc salts such as the following, are contemplated by the invention:
• the normal zinc salts of bis(alkyl)- dithiophosphoric acids which ane improved by the invention are those derived from aliphatic alcohols having 2 neo or hindered carbon atom adjacent to the carbon atorr bearing the hydroxyl group. These alcohols conform tc the structure where R is alkyl. These alcohols and consequently the alkyl groups derived therefrom may contain from 5 up to about 20 carbon atoms.
• suitable zinc dithiophosphate salts of this type are the following:
• the zinc carboxylates with which the Zinc dithiophos phate salts may be coordinated in accordance with the in vention may be either aliphatic or aromatic in nature
• the aliphatic Zinc carboxylates may be of the straight chained, branch-chained or cyclic type and may contair from 1 to about 20 carbon atoms.
• thes salts are zinc acetate, Zinc formate, zinc butyrate, zir1 decanoate, zinc stearate, zinc oleate, zinc linoleate and th like.
• Zinc naphthenate salts derived from petroleun oil naphthenic acids, are also highly suitable.
• the aro matic carboxylate salts include, for example, zinc ben zoate, zinc salicylate and such salts which also have one or more alkyl groups having from 1 to 20 carbon atom: each substituted on the aromatic ring thereof.
• the mixture was dehydrated by refluxing for one and one-half hours. The temperature was then lowered to 130135 C. and 199.8 grams (0.9 mol) of phosphorus pentasulfide added, portionwise, over a period of one and one-half hours While maintaining the temperature at 130135 C. The mixture was then heated to reflux and refluxed for one hour (144l45 C.). The mixture was then cooled to approximately 90 C. and 150 cc. of distilled water added over a period of about one-half hour. The temperature was held at 8893 C. for two hours to form the normal zinc salt of bis('nonylphenyl)dithiophosphate. The mixture was then heated to reflux to azeotrope the water.
• the product was then cooled to about 100 C. and filtered through Super-Cel (a diatomaceous earth filter aid).
• the xylene was then removed at reduced pressure using a water-bath-as a source of heat.
• the reaction mixture was then diluted with approximately 25%, by weight, of mineral oil (100 S.U.S. 100 F.), warmed on a waterbath and filtered through a bed of cuper-Cel.
• the temperature was raised to reflux and the mixture refluxed for one hour (144147 C.).
• the temperature was reduced to approximately 90 C. and 150 cc. of distilled water was added from the dropping funnel over a period of about 15 minutes.
• the temperature was maintained at 9095 C. for two hours in order to form the normal zinc salt of bis(n0nylphenyl)- dithiophosphoric acid.
• paraffinic mineral oil 100 S.U.S. 100 F.
• xylene-free salt product containing about 25%, by weight, of oil.
• the xylene was removed at reduced pressure using a waterbath as a source of heat.
• the maximum azeotroping temperature was 116 C.
• the product was then filtered through a bed of Super- Cel. The product was then removed at reduced pressure using a boiling water-bath as a source of heat.
• the mixture was then refluxed to azeotrope the water.
• the product was then filtered through Super- Cel.
• the benzene was then removed at reduced pressure using a water-bath as a source of heat.
• the mixture was stirred and refluxed at approximately 144 C. to remove all water from the system.
• the temperature was reduced to approximately 130 C. and 34.3 grams (0.15 mol) of phosphorus pentasulfide was added over a period of 50 minutes at a reaction temperature of 130-135 C.
• the temperature of the mixture was raised to reflux (Ml-142 C.) and refluxed for one hour.
• the temperature was then reduced to approximately 90 C. and 88.0 grams (0.225 mol) of petroleum naphthenic acid was added, followed by 50 milliliters of distilled Water.
• the mixture was stirred and heated for two hours at 9093 C.
• the temperature was then raised to azeotrope the water (144 C.).
• the mixture was then cooled and filtered through Super-Cal.
• the filtrate was washed with 150 milliliters of fresh xylene.
• the xylene was removed from the filtrate at reduced pressure using a water-bath as a source of heat.
• the test method used was that developed by the Electro-Motive Division of General Motors Corporation, designated EMD Method No. LO. 201-47, for determining the corrosivity towards silver of a heavy duty lubricating oil.
• the procedure consists in heating in an oil bath held at 325 F.i2 F., 300 milliliters of lubricating oil contained in a 600-milliliter beaker. The oil is stirred at 300 rpm.
• a weighed section of a silver-plated wrist-pin bushing (approximate size 3" x 1" x A1"lead flashing removed from surface prior to test) is suspended in the oil so that it is immersed to approximately of its surface area.
• the bushing section is removed from the oil, washed with carbon tetrachloride and dried.
• the corrosion layer is then electrolytically removed after which the bushing is washed with water and alcohol and dried by wiping with a cloth and placing it in an oven held at F. for 10 minutes. After cooling in a desiccator, it is reweighed. If the weight loss is no greater than 5 milligrams, the oil is considered to have passed the test.
• the lubricating oil used in the tests was a Mid-Continent solvent-refined, all paraflin distillate having an S.U.V. of 77 seconds at 210 F.
• the percentage of additive used in the oil in each instance was adjusted to give the same percentage of zinc bound to sulfur (excludes the zinc bound to zinc carboxylate coordinating agent) as contained in 0.44% and 0.89%, by weight, respectively, of the normal zinc bis(4-methyl-2-pentyl)dithiophosphate additive (Example '5).
• the test results are shown in Table I.
• the coordinated salts contemplated by the invention contain approximately one mo of zinc carboxylate per mol of zinc dithiophosphate. 11 has been found that if less than approximately one moi of the zinc carboxylate is combined with the zinc dithiophosphate salt, the resulting coordinated salt will no? pass the silver corrosion test.
• the amount of zinc carboxylate salt used in the reaction with the zinc dithiophos- 7 phate salt therefore, must be at least about one mol per mol of zinc dithiophosphate, the use of a moderate excess over this amount, say, from 10% to about 50%, being preferred in order to insure incorporation of the required one mol proportion thereof in the coordinated salt product.
• the presence of water is essential to the coordination reaction, the minimum required amount being about 0.5 mol per mol of zinc dithiophosphate being reacted with the zinc carboxylate.
• the reaction is greatly facilitated, however, by the use of much larger amounts, say, from 10 to about 50 mols of water per mol of zinc dithiophosphate being reacted.
• the upper limit of the amount of water is not critical and the amount used is, therefore, governed largely by practical considerations.
• the coordinated salt products of the invention may conveniently be prepared in the form of concentrated oil solutions thereof which solutions are readily blendable with base oils desired to be improved thereby.
• concentration of the product salt in these solutions will depend, of course, on the amount of diluent oil used in the process. For commercial purposes this amount can be standardized to provide a specified level of concentration. Expressed on an oil-free basis, however, the amount of the coordinated salt to be utilized in lubricating oil will range from about 0.01% to about 10%, by Weight, the usual amount being from about 0.5% to about 5%.
• the lubricating oil to which the salts of the invention are added may also contain other addition agents designed to improve the characteristics of the oil in various respects, such as detergents, pour point depressants, viscosity index improvers, extreme pressure agents, additional antioxidants, etc.
• a zinc carboxylatecoordinated zinc dithiophosphate salt composed of approximately one mol proportion of zinc carboxylate per mol proportion of zinc dithiophosphate, said coordinated salt being prepared by the method which comprises (1) forming a reaction mixture of one mol proportion of (A) a zinc dithiophosphate salt of the formula where R is a hydrocarbon radical selected from the group consisting of (a) aryl radicals, (b) alkyl-substituted aryl radicals having from one to 5 alkyl radicals substituted on the aryl nucleus thereof, each of said alkyl radicals having from one up to about 20 carbon atoms and (c) alkyl radicals containing from 5 to about 20 carbon atoms in which the carbon atom adjacent to the carbon atom attached to the oxygen atom in said formula is completely substituted with alkyl groups, (B) at least one mol proportion of a Zinc salt of a carboxylic acid selected from the group consisting of (a) alipha
• a zinc acetatecoordinated zinc bis(nonylphenyl)dithiophosphate salt composed of approximately one mol proportion of zinc acetate per mol proportion of zinc bis(nonylphenyl)dithiophosphate, said coordinated salt being prepared by the method which comprises (1) forming a reaction mixture of (A) one mol proportion of normal bis(nonylphenyl)- dithiophosphate, (B) at least one mol proportion of zinc acetate, (C) water and (D) a hydrocarbon solvent; (2) heating the reaction mixture to distill oi the water and a portion of the hydrocarbon solvent as an azeotropic mixture; (3) filtering the reaction mixture to obtain a solvent solution of the zinc acetate-coordinated zinc bis- (nonylphenyl)dithiophosphate; and (4) distilling off the remainder of the solvent.
• a Zinc acetate-coordinated zinc bis(2,2,4-trimethyl-l-pentyl)dithiophosphate salt composed of approximately one mol proportion of zinc acetate per mol proportion of zinc bis(2,2,4- trimethyl-l-pentyl)dithiophosphate, said coordinated salt being prepared by the method which comprises (1) forming a reaction mixture of (A) one mol proportion of normal bis(2,2,4-trimethyl-1-pentyl)dithiophosphate, (B) at least one mol proportion of zinc acetate, (C) water and (D) a hydrocarbon solvent; (2) heating the reaction mixture to distill off the water and a portion of the hydrocarbon solvent as an azeotropic mixture; (3) filtering the reaction mixture to obtain a solvent solution of the zinc acetate-coordinated zinc bis(2,2,4-trimethyl-1-pentyl)- dithiophosphate; and (4) distilling off the remainder of the solvent.
• a zinc naphthenatecoordinated zinc bis(mixed phen0ls) dithiophosphate salt composed of approximately one mol proportion of zinc naphthenate per mol proportion of zinc bis(mixed phenols) dithiophosphate, said coordinated salt being prepared by the method which comprises (1) forming a reaction mixture of (A) one mol proportion of normal bis(mixed phenols)dithiophosphate, (B) at least one mol proportion of zinc naphthenate, (C) water and (D) a hydrocarbon solvent; (2) heating the reaction mixture to distill off the water and a portion of the hydrocarbon solvent as an azeotropic mixture; (3) filtering the reaction mixture to obtain a solvent solution of the zinc naphthenatecoordinated zinc bis(mixed phenols)dithiophosphate; and (4) distilling off the remainder of the solvent.
• a lubricating oil containing a minor amount, from about 0.01% to about by weight, of a zinc acetatecoordimated zinc bis(nonylphenyl) dithiophosphate salt composed of approximately one mol proportion of zinc acetate per mol proportion of zinc bis(nonylphenyl)dithophosphate, said ooordinated salt being prepared by the method which comprises (1) forming a reaction mixture of (A) one mol proportion of normal bis(nonyl phenyDdithiophosph-ate, ('B) at least one mol proportion of zinc acetate, (C) water and (D) a hydrocarbon solvent; (2) heating the reaction mixture to distill ofi the Water and a portion of the hydrocarbon solvent as an azeotropic mixture; (3) filtering [the reaction mixture to obtain a solvent solution of the zinc acetate-coordinated bis(nonylphenyl)tdithiophosphate; and (4) distilling olf the remainder of the solvent

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  • FR FR1310171D patent/FR1310171A/fr not_active Expired
• 1960
  • 1960-12-20 US US76998A patent/US3102096A/en not_active Expired - Lifetime
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