GB944062A - Process for the preparation of organic phosphines - Google Patents

Process for the preparation of organic phosphines

Info

Publication number
GB944062A
GB944062A GB3749561A GB3749561A GB944062A GB 944062 A GB944062 A GB 944062A GB 3749561 A GB3749561 A GB 3749561A GB 3749561 A GB3749561 A GB 3749561A GB 944062 A GB944062 A GB 944062A
Authority
GB
United Kingdom
Prior art keywords
phosphine
butylbis
trifluoromethylphenyl
dibutyl
naphthyl
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
GB3749561A
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
Priority claimed from US67883A external-priority patent/US3060241A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB944062A publication Critical patent/GB944062A/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
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
    • 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
    • C07F9/50—Organo-phosphines
    • C07F9/505—Preparation; Separation; Purification; Stabilisation

Landscapes

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

Abstract

Phosphines are prepared by reacting in an inert organic solvent (a) elemental phosphorus, (b) an organometallic compound RLi or RMgX where X is halogen and R is unsubstituted or substituted C1-12 alkyl, cycloalkyl or unsubstituted or substituted aryl, said substituents being halogen or C1-6 alkoxy and, if desired, (c) an alkyl halide, and, essentially when an alkyl halide is not present and optionally otherwise, hydrolysing the reaction mixture with water or dilute mineral acid when the reaction is completed. Temperatures of 0-150 DEG C. may be used. Primary, secondary and tertiary phosphines may be prepared and if molar ratios of reactants of the order 2(RMgX):1(P4):2(alkylhalide) are used, the product is stated to be a cyclotetraphosphine. The reaction mixture in Example V is treated with LiAlH4 before hydrolysis. Products prepared in examples are: phenylphosphine, diphenylphosphine, triphenylphosphine, butylphosphine, dibutylphosphine, tributylphosphine, naphthylphosphine, dinaphthylphosphine, trinaphthylphosphine, 4-methoxyphenylphosphine, 4-fluorophenulphosphine, octylphosphine, dioctylphosphine, trioctylphosphine, cyclohexylphosphine, dodecylphosphine, butylphenylphosphine, dibutylphenylphosphine, butyldiphenylphosphine, butyl (1-naphthyl) phosphine, butylbis (1-naphthyl) phosphine, dibutyl (3-trifluoromethylphenyl) phosphine, butylbis (3-trifluoromethylphenyl) phosphine, dibutyl (4-methoxyphenyl) phosphine, butylbis (4 - methoxyphenyl) phosphine, dibutyloctylphosphine, butyldioctylphosphosphine, hexyldimethylphosphine, dihexylmethylphosphine, butyl 4-fluoro-phenylphosphine, butylbis (4-fluorophenyl) phosphine, dibutyl 4-fluorophenylphosphine, cyclohexyldihexylphosphine, dicyclohexylhexylphosphine, tridodecylphosphine, dipentylpropylphosphine, dipropylpentylphosphine, trihexylphosphine, dimethyl 6-methoxy - 2 - naphthylphosphine, bis (6-methoxy - 2 - naphthyl) methylphosphine, and butylbis (3-trifluoromethylphenyl) phosphine.ALSO:Naphthalene and 1-butylnaphthalene are among the products when white phosphorus is added to an ethereal solution of 1-naphthyllithium and butylbromide obtained from butyllithium and 1-bromo-naphthalene (Example XXIII).
GB3749561A 1960-11-08 1961-10-19 Process for the preparation of organic phosphines Expired GB944062A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6788460A 1960-11-08 1960-11-08
US67883A US3060241A (en) 1960-11-08 1960-11-08 Preparation of alkyl cycloalkyl and aromatic phosphines

Publications (1)

Publication Number Publication Date
GB944062A true GB944062A (en) 1963-12-11

Family

ID=26748370

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3749561A Expired GB944062A (en) 1960-11-08 1961-10-19 Process for the preparation of organic phosphines

Country Status (3)

Country Link
DE (2) DE1197449B (en)
FR (1) FR1304533A (en)
GB (1) GB944062A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019025001A1 (en) 2017-08-04 2019-02-07 Wacker Chemie Ag Silicone compositions that can be cross-linked by irradiation with uv light

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2900416A (en) * 1956-02-21 1959-08-18 American Potash & Chem Corp Method of preparation of alkyl-substituted phosphines
SU130512A1 (en) * 1960-02-15 1960-11-30 В.И. Емельянов Method for producing alkyl and (aryl) dihalo phosphines and dialkyl and (diaryl) halo phosphines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019025001A1 (en) 2017-08-04 2019-02-07 Wacker Chemie Ag Silicone compositions that can be cross-linked by irradiation with uv light
US11098197B2 (en) 2017-08-04 2021-08-24 Wacker Chemie Ag Silicone compositions crosslinkable by irradiation with UV light

Also Published As

Publication number Publication date
FR1304533A (en) 1962-09-21
DE1197449B (en) 1965-07-29
DE1201836B (en) 1965-09-30

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