GB756099A - A process for the manufacture of esters containing phosphorus, oxygen and sulphur - Google Patents

A process for the manufacture of esters containing phosphorus, oxygen and sulphur

Info

Publication number
GB756099A
GB756099A GB16892/54A GB1689254A GB756099A GB 756099 A GB756099 A GB 756099A GB 16892/54 A GB16892/54 A GB 16892/54A GB 1689254 A GB1689254 A GB 1689254A GB 756099 A GB756099 A GB 756099A
Authority
GB
United Kingdom
Prior art keywords
esters
acid
sultone
ester
formula
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
GB16892/54A
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.)
Boehme Fettchemie GmbH
Original Assignee
Boehme Fettchemie GmbH
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 Boehme Fettchemie GmbH filed Critical Boehme Fettchemie GmbH
Publication of GB756099A publication Critical patent/GB756099A/en
Expired legal-status Critical Current

Links

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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids R2P(=O)(OH); Thiophosphinic acids, i.e. R2P(=X)(XH) (X = S, Se)
    • C07F9/32—Esters thereof
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Abstract

Esters containing phosphorus, oxygen, and sulphur are obtained by reacting a neutral ester of an acid of trivalent phosphorus with a sultone at an elevated temperature. The neutral ester may be of the type (RO)3P in which R is an acyclic or cycloaliphatic residue, the products in this case being neutral esters of phosphonic-sulphonic acids. The neutral ester starting materials may also be esters of alkyl- or aryl phosphonous acids of the formula R1.P(OR)2 or esters of the dialkyl- or diaryl-phosphinous acids of the formula (R1)2P.OR, R1 being an alkyl or aryl residue and R being as defined above. Specified ester starting materials are triethyl-, and trioctyl-phosphite, ethyl-dibutyl phosphite, tricycloalkyl esters such as tricyclohexyl phosphite and tri-(methylcyclohexyl) phosphite, the diethyl ester of phenylphosphonous acid, and the ethyl ester of dibutylphosphinous acid. Specified sultones are propane sultone, butane sultone, tolyl sultone and 1,8-naphthyl sultone. The reaction is preferably carried out at 50-180 DEG C. and inert solvents or diluents may be present. In examples: (1) propane sultone is boiled under reflux with triethyl phosphite in xylene to yield propane-1-phosphonic acid-3-sulphonic acid triethyl ester; (2) as in (1) except that tributyl phosphite is used, the product being propane-1-phosphonic acid-3-sulphonic acid tributyl ester. The products obtained from the esters of alkyl or aryl phosphonous acids of the formula R1P(OR)2 are phosphinic-sulphonic acid diesters of the formula (RO)(R1)P(O)R11SO2.OR, whilst the products obtained from the dialkyl or diaryl phosphinous acid esters of the formula (R1)2P.OR are sulphonic esters of a phosphinic oxide of the formula (R1)2P(O).R11.SO2.OR; R11 in each case being the alkylene or arylene radical present in the sultone.
GB16892/54A 1953-06-10 1954-06-09 A process for the manufacture of esters containing phosphorus, oxygen and sulphur Expired GB756099A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE756099X 1953-06-10

Publications (1)

Publication Number Publication Date
GB756099A true GB756099A (en) 1956-08-29

Family

ID=6659748

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16892/54A Expired GB756099A (en) 1953-06-10 1954-06-09 A process for the manufacture of esters containing phosphorus, oxygen and sulphur

Country Status (1)

Country Link
GB (1) GB756099A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3937721A (en) * 1973-05-07 1976-02-10 The Lubrizol Corporation Method for the preparation of sulfonic acid esters from free sulfonic acids
US4059432A (en) * 1974-05-27 1977-11-22 Mitsubishi Petrochemical Co., Ltd. Plant growth regulator
US5712396A (en) * 1992-10-28 1998-01-27 Magnin; David R. α-phosphonosulfonate squalene synthetase inhibitors
US5731299A (en) * 1992-05-29 1998-03-24 The Procter & Gamble Company Phosphonosulfonate compounds, pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3937721A (en) * 1973-05-07 1976-02-10 The Lubrizol Corporation Method for the preparation of sulfonic acid esters from free sulfonic acids
US4059432A (en) * 1974-05-27 1977-11-22 Mitsubishi Petrochemical Co., Ltd. Plant growth regulator
US4059431A (en) * 1974-05-27 1977-11-22 Mitsubishi Petrochemical Co., Ltd. Plant growth regulator
US5731299A (en) * 1992-05-29 1998-03-24 The Procter & Gamble Company Phosphonosulfonate compounds, pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism
US5712396A (en) * 1992-10-28 1998-01-27 Magnin; David R. α-phosphonosulfonate squalene synthetase inhibitors

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