GB699522A - Improvements relating to the preparation of phosphate esters - Google Patents

Improvements relating to the preparation of phosphate esters

Info

Publication number
GB699522A
GB699522A GB3808/51A GB380851A GB699522A GB 699522 A GB699522 A GB 699522A GB 3808/51 A GB3808/51 A GB 3808/51A GB 380851 A GB380851 A GB 380851A GB 699522 A GB699522 A GB 699522A
Authority
GB
United Kingdom
Prior art keywords
radicals
aliphatic
iso
aromatic hydrocarbon
hydrocarbon radicals
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
GB3808/51A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB699522A publication Critical patent/GB699522A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/167—Phosphorus-containing compounds
    • C23F11/1673—Esters of phosphoric or thiophosphoric acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • 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
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/5398—Phosphorus bound to sulfur
    • 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
    • C10M137/105—Thio derivatives not containing metal
    • 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
    • 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

Abstract

The invention comprises compounds of the formula <FORM:0699522/IV (b)/1> in which R1 and R2 are aliphatic or aromatic hydrocarbon radicals, and R3 and R4 are hydrogen or aliphatic or aromatic hydrocarbon radicals, or halogen derivatives thereof. They are prepared by reacting an acid phosphate of the formula <FORM:0699522/IV (b)/2> with maleic or fumaric acid or the appropriate mono- or di-esters of these acids. Solvents in which the reaction may be performed p are specified, including various alcohols, ketones, aliphatic esters, dimethoxy ethane, dioxane, benzene, toluene, xylene, nitrobenzene, chlorbenzene, chloroform, carbon tetrachloride, and tri-alkyl phosphates. Tertiary amine catalysts, e.g. triethylamine, triisopropylamine, tri-n-butylamine or tri-2-ethylhexylamine, and anti-polymerization agents, e.g. hydroquinone, catechol, resorcinol, pyrogallol or phloroglueinol may be added to the reaction mixture. In examples (1) S-(1,2-dicarbethoxyethyl)O,O-diethyl dithiophosphate is prepared by reacting O,O-diethyl dithiophosphoric acid and diethyl fumarate; (2) S-(1,2-dicarbomethoxyethyl)O,O-dimethyl dithiophosphate is obtained by reacting O,O-dimethyl di-thiophosphoric acid and dimethyl maleate. In a generally similar manner are prepared similar compounds represented by the above general formula containing at R1, R2, R3 and R4 various combinations of radicals selected from methyl, ethyl, n- and iso-propyl, n- and iso-butyl, 2-chlorethyl, allyl, 2-ethylhexyl, 2-butyloctyl, phenyl, n-decyl, and n-octadecyl radicals. Also mentioned are sec-amyl, n-hexyl, n-octyl, n-dodecyl, oleyl, cetyl, ceryl, cyclohexyl and naphthyl radicals. The products may be used as insecticides, fungicides, plasticizers, corrosion inhibitors, flotation agents, and petroleum additives.ALSO:Phosphate esters of the general formula <FORM:0699522/VI/1> where R1 and R2 are aliphatic or aromatic hydrocarbon radicals and R3 and R4 are hydrogen or aliphatic or aromatic hydrocarbon radicals or halogen derivatives thereof (see Group IV (b)) are used as fungicides and insecticides. They show very low warm-blooded animal toxicity. Specified radicals are methyl, ethyl, n- and iso-propyl, n- and iso-butyl, 2-chloroethyl, allyl, 2-ethyl hexyl, 2-butyloctyl, phenyl, n-decyl, n-octadecyl, sec-amyl, n-hexyl, n-octyl, n-dodecyl, oleyl, cetyl, ceryl, cyclohexyl and naphthyl.
GB3808/51A 1950-03-02 1951-02-16 Improvements relating to the preparation of phosphate esters Expired GB699522A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US147325A US2578652A (en) 1950-03-02 1950-03-02 Addition product of diester of dithiophosphoric acid and maleic acid and its esters, and method of preparation

Publications (1)

Publication Number Publication Date
GB699522A true GB699522A (en) 1953-11-11

Family

ID=22521112

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3808/51A Expired GB699522A (en) 1950-03-02 1951-02-16 Improvements relating to the preparation of phosphate esters

Country Status (8)

Country Link
US (1) US2578652A (en)
BE (1) BE501609A (en)
CH (1) CH292795A (en)
DE (1) DE847897C (en)
ES (1) ES196779A1 (en)
FR (1) FR1033275A (en)
GB (1) GB699522A (en)
NL (2) NL80825C (en)

Families Citing this family (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1063154B (en) * 1950-05-09 1959-08-13 Bayer Ag Process for the preparation of thiophosphoric acid esters
US2675321A (en) * 1951-06-12 1954-04-13 American Cyanamid Co Coated pigment and mineral oil ink containing same
US2632020A (en) * 1951-07-07 1953-03-17 American Cyanamid Co Dithiophosphate esters
US2644002A (en) * 1951-08-29 1953-06-30 American Cyanamid Co Thiophosphatosuccinimides
US2630451A (en) * 1951-12-08 1953-03-03 American Cyanamid Co Dithiophosphate esters
NL185227B (en) * 1953-02-18 Granly Trykluft Aps DEVICE AND SCRAPER ROLLER FOR REMOVING FAT AND MEAT FROM THE MEAT SIDE OF A PEL.
DE956503C (en) * 1953-07-22 1957-01-17 Geigy Ag J R Process for the production of new phosphoric or thiophosphoric acid esters
US2802856A (en) * 1953-09-08 1957-08-13 Lubrizol Corp Methods of preparing tri-esters of thiophosphoric acids
DE942988C (en) * 1953-12-11 1956-05-09 Bayer Ag Process for the preparation of thiolphosphoric acid triesters
DE951717C (en) * 1953-12-19 1956-10-31 Bayer Ag Process for the production of thionothiol-phosphoric acid triesters
BE541123A (en) * 1954-09-08
US2976308A (en) * 1954-10-13 1961-03-21 Lubrizol Corp Preparation of phosphorodithioate triesters
US2876244A (en) * 1954-12-30 1959-03-03 Union Carbide Corp Production of heterocyclic dithiophosphoric esters
DE1011416B (en) * 1955-02-10 1957-07-04 Bayer Ag Process for the production of 0, 0-dialkyl-thiol and thiol-thiono-phosphoric acid triesters
DE1006854B (en) * 1955-02-10 1957-04-25 Bayer Ag Process for the preparation of thionophosphoric acid esters
FR1125317A (en) * 1955-04-12 1956-10-29 Process for deodorizing diethyl mercaptosuccinate o, o-dimethyl-dithiophosphate
US2879284A (en) * 1955-08-12 1959-03-24 American Cyanamid Co Odor removal and stabilization of phosphate-containing pesticides
US2911335A (en) * 1955-09-27 1959-11-03 Allied Chem Thiophosphate ester fungicides
DE1112338B (en) * 1956-05-03 1961-08-03 Pfizer & Co C Pest repellent with insecticidal and especially miticidal effects
US2876156A (en) * 1956-05-03 1959-03-03 Pfizer & Co C Insecticides-derivatives of itaconic acid
US2861093A (en) * 1956-09-24 1958-11-18 Eastman Kodak Co Reaction products of dialkyl phosphorothiolothionates and mucohalic acids
DE1034612B (en) * 1956-09-28 1958-07-24 Basf Ag Process for the preparation of esters of phosphoric acid and thiophosphoric acid
US2948682A (en) * 1956-12-24 1960-08-09 Pure Oil Co Formyl triesters of dithiophosphoric acid and lubricating oil compositions containing same
US2947775A (en) * 1957-11-25 1960-08-02 Eastman Kodak Co O, o-dialkyl s-(2-acetoxy-2-cyanoethyl) phosphorothiolothionates
US2957019A (en) * 1958-02-14 1960-10-18 Eastman Kodak Co O, o-dialkyl s-(2-cyano-haloalkyl) phosphorothiolothionates
US3136686A (en) * 1958-10-31 1964-06-09 Ciba Ltd Omicron, omicron-dialkyl s-alkenyl phosphorothioates and insecticidal compositions and methods employing same
NL244044A (en) * 1958-11-07
US3074990A (en) * 1958-12-29 1963-01-22 Universal Oil Prod Co Alkylthiophosphoric acid salt of polymeric condensation product and use thereof
BE626519A (en) * 1959-06-16
US3030264A (en) * 1960-03-11 1962-04-17 Monsanto Chemicals 1, 2-bis (oxycarbonyl) ethyl phosphinothioates
US3048517A (en) * 1960-05-12 1962-08-07 Monsanto Chemicals 2-nitroalkyl phosphorothioates
FR1310158A (en) * 1960-12-10 1963-03-06
DE1188859B (en) * 1960-12-10 1965-03-11 Basf Ag Preparations for the control of insects
US3109770A (en) * 1961-04-10 1963-11-05 Stauffer Chemical Co Dialkoxyphosphinyl carbalkoxyalkyl disulfide pesticides
US3092543A (en) * 1961-05-09 1963-06-04 Velsicol Chemical Corp Allyl phthalate pesticidal compositions
DE1198360B (en) * 1961-08-03 1965-08-12 Imperial Chemical Industries Limited, London Process for the preparation of o-alkyl-S- (l-phenyl-2-alkoxycarbonyl-ethyl) -alkylthiophosphonates
BE621471A (en) * 1961-08-18
US3515782A (en) * 1964-11-27 1970-06-02 American Cyanamid Co Method for controlling insects
US3359203A (en) * 1965-09-01 1967-12-19 Exxon Research Engineering Co Ashless dithiophosphoric acid derivatives
US3440305A (en) * 1965-09-30 1969-04-22 American Cyanamid Co Process for upgrading malathion
US3470272A (en) * 1966-10-24 1969-09-30 Mobil Oil Corp Process for making phosphorothioates
US3463841A (en) * 1966-11-01 1969-08-26 American Cyanamid Co Malathion manufacture
CH569416A5 (en) * 1972-04-27 1975-11-28 Ciba Geigy Ag
US4058605A (en) * 1975-06-11 1977-11-15 Sun Ventures, Inc. Insecticides from dimethylmuconic acid
DE2715924A1 (en) * 1977-04-09 1978-10-12 Basf Ag NEW PHOSPHORSAE DERIVATIVES
DE2746057A1 (en) * 1977-10-13 1979-04-26 Basf Ag NEW PHOSPHORUS (PHOSPHONE) ACID ESTER
US5614203A (en) * 1995-01-30 1997-03-25 Environmentally Safe Systems, Inc. Environmentally safe pesticide and plant growth accelerator
US5646133A (en) * 1996-03-14 1997-07-08 Donlar Corporation Polyaspartic acid and its analogues in combination with insecticides
US6046144A (en) * 1997-06-02 2000-04-04 R.T. Vanderbilt Co., Inc. Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions
DE19953775A1 (en) 1999-11-09 2001-05-10 Bayer Ag Active ingredient combinations with insecticidal and acaricidal properties
DE10015310A1 (en) * 2000-03-28 2001-10-04 Bayer Ag Active ingredient combinations with insecticidal and acaricidal properties
US8012498B2 (en) 2004-07-12 2011-09-06 Sandhya Goyal Topical gel formulation comprising organophosphate insecticide and preparation thereof
US8158139B2 (en) * 2004-07-12 2012-04-17 Taro Pharmaceuticals North America, Inc. Topical gel formulation comprising organophosphate insecticide and preparation thereof
US7560445B2 (en) 2005-07-06 2009-07-14 Taro Pharmaceuticals North America, Inc. Process for preparing malathion for pharmaceutical use
US8138366B2 (en) 2007-07-09 2012-03-20 Suven Life Sciences Limited Process for the preparation of malathion and its intermediate
ES2477888T3 (en) 2010-01-20 2014-07-18 W.R. Grace & Co.-Conn. Setting retardant applied to a surface that induces high healing

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US2528732A (en) * 1947-01-31 1950-11-07 Socony Vacuum Oil Co Inc Reaction products of diesters of dithiophosphoric acid and mineral oil compositions containing the same

Also Published As

Publication number Publication date
DE847897C (en) 1952-08-28
US2578652A (en) 1951-12-18
CH292795A (en) 1953-08-31
BE501609A (en)
NL159376B (en)
ES196779A1 (en) 1953-04-01
NL80825C (en)
FR1033275A (en) 1953-07-09

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