WO2003097654A1 - Procede de production d'un compose d'alcenylphosphore - Google Patents

Procede de production d'un compose d'alcenylphosphore Download PDF

Info

Publication number
WO2003097654A1
WO2003097654A1 PCT/JP2003/005807 JP0305807W WO03097654A1 WO 2003097654 A1 WO2003097654 A1 WO 2003097654A1 JP 0305807 W JP0305807 W JP 0305807W WO 03097654 A1 WO03097654 A1 WO 03097654A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
general formula
represented
groups
alkenyl
Prior art date
Application number
PCT/JP2003/005807
Other languages
English (en)
Japanese (ja)
Inventor
Li-Biao Han
Chen Zhang
Masato Tanaka
Original Assignee
Japan Science And Technology Corporation
National Institute Of Advanced Industrial Science And Technology
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 Japan Science And Technology Corporation, National Institute Of Advanced Industrial Science And Technology filed Critical Japan Science And Technology Corporation
Publication of WO2003097654A1 publication Critical patent/WO2003097654A1/fr

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 Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5316—Unsaturated acyclic phosphine oxides or thioxides
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4015—Esters of acyclic unsaturated acids

Definitions

  • the present invention relates to a method for producing an alkenyl phosphorus compound such as an alkenyl phosphonate, an alkenyl phosphinate and an alkenyl phosphoxide.
  • an alkenyl phosphorus compound such as an alkenyl phosphonate, an alkenyl phosphinate and an alkenyl phosphoxide.
  • This compound is also a very useful compound that can be easily converted to tertiary phosphine or the like widely used as an auxiliary ligand for various catalytic reactions.
  • the compound is a group of compounds having high utility in the synthesis of fine chemicals, for example, easily reacting with a nucleophile or a radical species, and can be used for the Horner-Wit iig reaction. Background art
  • a corresponding alkenyl halide compound is obtained by hydrogenating a phosphonic acid ester, a hydrogenated phosphinic acid ester, or the like.
  • a method of substituting with a di-substituted phosphoxide (hereinafter, these phosphorus compounds are collectively referred to as PH compounds) is considered.
  • this method requires the addition of a base to capture the hydrogen halide produced simultaneously with the reaction, thereby producing a large amount of a hydrogen halide salt.
  • the alkenyl halide compound which is the starting material, is not always easily available industrially and generally has toxicity.
  • An object of the present invention is to provide a method for producing an alkenyl lin compound using a PH compound as a starting material and using an inexpensive catalyst.
  • the present inventors have conducted intensive studies on the reaction between an easily available PH compound and an acetylene compound, and as a result, this addition reaction proceeds in the presence of an inexpensive nickel catalyst.
  • the inventors have found that a rurin compound is provided, and have completed the present invention.
  • the present invention relates to a compound represented by the general formula [1] in the presence of a catalyst containing nickel:
  • R 2 in the case of R 1 and R 2 when n is 1, and n is 2 are each independently a hydrogen atom, substituted Alkyl groups, cycloalkyl groups, alkenyl groups, cycloalkenyl groups, aryl groups, aralkyl groups, heteroaryl groups, alkoxy groups, cycloalkoxy groups, aralkyloxy groups, aryloxy groups, aryl groups And represents a silyl group or a phenyl phenyl group, and when n is 2, R 1 represents an optionally substituted alkylene group, a cycloalkylene group, an alkenylene group, or a cycloalkenelen; Group, arylene group, aralkylene group, heteroarylene group, alkylenedioxy group, cycloalkylenedioxy group, aralkylenedioxy group, arylenedioxy group And an acetylene compound represented by the general formula [
  • X 1 represents O R 3 or R 3
  • X 2 represents OR 4 or R 4 (provided that R 3 and R 4 may each independently have a substituent An alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, and a bond or a bond formed by removing one hydrogen atom or a group itself from each of R 3 and R 4 ; A cyclic structure may be formed.) [3] characterized by reacting with a phosphorus compound represented by the general formula [3]:
  • n is R 1 and R 2 in the case of 1, and n is represented by R 2 in the case of two may have a substituent
  • the alkyl group of the alkyl group include a linear or branched alkyl group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a pentyl group, a hexyl group and the like.
  • Examples of the cycloalkyl group of the cycloalkyl group which may have a substituent include, for example, a monocyclic ring having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.
  • Examples thereof include a cyclic or condensed cycloalkyl group, and more specific examples thereof include a propyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and a dodecyl group.
  • alkenyl group of the alkenyl group which may have a substituent examples include, for example, those having one or more double bonds in the alkyl group having 2 or more carbon atoms described above, and more specifically, Examples thereof include an aryl group, a 1-propenyl group, an isopropyl group, a 2-butenyl group, a 1,3-butenyl group, a 2-pentenyl group, and a 2-hexenyl group.
  • Examples of the cycloalkenyl group of the cycloalkenyl group which may have a substituent include those having one or more double bonds in the cycloalkyl group described above. More specifically, a cyclopropenyl group, Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cyclooctenyl group.
  • aryl group of the aryl group which may have a substituent examples include, for example, a monocyclic, polycyclic or condensed ring having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 14 carbon atoms.
  • Specific examples include a cyclic aromatic hydrocarbon group, and more specific examples include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, a methylnaphthyl group, an anthryl group, a phenanthryl group, and a biphenyl group.
  • a monocyclic, polycyclic or condensed ring having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 14 carbon atoms.
  • Specific examples include a cyclic aromatic hydrocarbon group, and more specific examples include a phenyl group, a tolyl group, a xylyl group, a nap
  • alkoxy group of the alkoxy group which may have a substituent examples include an alkoxy group having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms. Specific examples thereof include a methoxy group, an ethoxy group, and a butoxy group. And the like.
  • Examples of the cycloalkoxy group of the cycloalkoxy group which may have a substituent include, for example, a monocyclic, polycyclic or 3- to 30-carbon, preferably 3- to 20-, more preferably 3- to 12-carbon group.
  • Examples include a condensed cyclic cycloalkoxy group, and more specific examples include a cyclopropyl pyroxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclooctyloxy group, a cyclododecyloxy group, and the like.
  • Examples of the optionally substituted aralkyloxy group include a monocyclic, polycyclic or fused cyclic aralkyloxy group having 7 to 30 carbon atoms, preferably 7 to 20 carbon atoms, and more preferably 7 to 15 carbon atoms. And more specifically, for example, a benzyloxy group, a phenethyloxy group, a naphthylmethyloxy group, a naphthylethyloxy group and the like.
  • an aryloxy group having a condensed cyclic aromatic hydrocarbon group more specifically, for example, a phenoxy group, a tolyloxy group, a xylyloxy group, a naphthoxy group, a methylnaphthyloxy group, an anthroxy group, Huenantrilou And a xy group and a piphenyloxy group.
  • Examples of the substituent of the alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, aryl group, aralkyl group, heteroaryl group, alkoxy group, cycloalkoxy group, aralkyloxy group and aryloxy group include, for example, methyl group, ethyl group, propyl group.
  • Alkyl groups such as groups, hydroxyl groups, such as methoxy groups, ethoxy groups, propoxy groups, butoxy groups, etc., alkoxy groups, such as chlorine, bromine, fluorine, etc., halogen atoms, cyano groups, such as dimethylamino group, dimethylamino group, etc.
  • Substituted amino groups such as alkoxycarbonyl groups such as methoxycarbonyl and ethoxycarbonyl groups; silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group and triphenylsilyl group; Ryl groups include, for example, siloxy groups such as t-butyldimethylcyclooxy group and the like.
  • the silyl group which may have a substituent includes, for example, those substituted with an alkyl group, an aryl group, an aralkyl group, an alkoxy group and the like. Specific examples thereof include a trimethylsilyl group, a triethylsilyl group, a triphenylsilyl group, a phenyldimethylsilyl group, a trimethoxysilyl group, a t-butyldimethylsilyl group, and the like.
  • an optionally substituted alkylene group represented by R 1 an optionally substituted cycloalkylene group, an optionally substituted alkenylene group,
  • a cycloalkenedylene group which may have a group, an arylene group which may have a substituent, an aralkylene group which may have a substituent, and a group which may have a substituent T-arylenylene group, alkylenedioxy group optionally having substituent (s), cycloalkylenedioxy group optionally having substituent (s), arylenedioxy group optionally having substituent (s)
  • An xyl group, a silylene group which may have a substituent, or a ferrosenylene group is a divalent residue obtained by removing one hydrogen atom from R ′ when n is 1 or one oxygen atom Selected from divalent residues replaced by one atom, specific examples Examples include methylene, ethylene, trimethylene, methylethylene, tetramethylene, 1,
  • Examples of the acetylene compound represented by the general formula [1] preferably used in the production method of the present invention include: unsubstituted acetylene, methylacetylene, butyne,
  • Examples include, but are not limited to, 1,8-nonadiyne and gechelbenzene.
  • R 3 and R 4 each independently represent an optionally substituted alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. Also, R 3 and R 4 (4) Each group may be bonded to each other by a residue or a bond obtained by removing one hydrogen atom or the group itself from each group to form a cyclic structure.
  • the alkenyl lin compound represented by the general formula [3] or / and the general formula [4] produced by the following general formula [3a] or / and the general formula [4a]
  • n, RR 2 , R 3 and R 4 are the same as described above.
  • R 3 and R 4 are each independently an optionally substituted alkyl group, the cycloalkyl group, the same Ararukiru group or the Ariru group. Further, R 3 ⁇ And R 4 may be bonded to each other by a residue or a bond obtained by removing one hydrogen atom or the group itself from each group to form a cyclic structure.
  • n, RR 2 , R 3 and R 4 are the same as described above.
  • the phosphorus compound (P—H compound) represented by [2] has the following general formula [2c]
  • R 3 and R 4 each independently represent an optionally substituted alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. Also, R 3 and R 4 4 It may be bonded to each other by a residue or bond other than one hydrogen atom or the group itself from each group to form a cyclic structure.
  • a disubstituted phosphine oxide represented by The resulting alkenyl lin compound represented by the general formula [3] or / and / or the general formula [4] is represented by the following general formula [3c] or / and the general formula [4c]
  • n, RR 2 , R 3 and R 4 are the same as described above.
  • one hydrogen atom or group from each group of R 3 and R 4 Specific examples of the case in which a cyclic structure is formed by bonding to each other by a residue or a bond other than those described above include, for example, an ethylene group, a tetramethylethylene group, a trimethylene group, a tetramethylene group, and an orthophenylene. And an orthoxylylene group, but are not limited thereto.
  • P—H compounds used in the production method of the present invention include dimethyl phosphonate, getyl phosphonate, dibutyl phosphonate, diphenyl phosphonate, 4,4,5,5-tetramethyl-1,3 , 2-Dioxaphospholane-2-oxide, phenylphosphinic acid ethyl, cyclohexyl phenylphosphinate, diphenylphosphinoxide, and the like, but are not limited thereto.
  • the molar ratio of the acetylene compound to the PH compound is preferably 1: 1. However, if it is larger or smaller than this, it does not inhibit the occurrence of the reaction.
  • the reaction according to the invention proceeds at a favorable rate in the presence of a catalyst comprising nickel, in particular a nickel complex catalyst.
  • nickel complex catalyst Although various structures can be used as the nickel complex catalyst, a preferable one is a so-called low-valent nickel complex catalyst.
  • a low-valent nickel complex having a ligand of a trivalent phosphorus compound such as tertiary phosphine or tertiary phosphite can also be preferably used.
  • a precursor complex which can be easily converted to a low-valent complex in the reaction system and form a low-valent nickel complex in the reaction system for the reaction.
  • trivalent phosphines and tertiary phosphites and other trivalent lin compounds such as the same metal complexes that do not contain ligands, and tertiary phosphines and tertiary phosphites and other trivalent lin compounds and the like.
  • Tertiary phosphine, tertiary phosphite, and other trivalent phosphine compounds such as tertiary phosphine The method and the like are also preferable embodiments.
  • tertiary ligands exhibit advantageous performance in any of these methods.
  • examples thereof include trivalent phosphorus compounds such as phosphine and tertiary phosphite.
  • suitable ligands include, for example, triphenylphosphine, diphenylmethylphosphine, phenyldimethylphosphine, triethylphosphine, tricyclohexylphosphine, 1,4-bis (diphenylphosphine).
  • Tertiary phosphines complexes that do not contain tertiary phosphites as ligands that are used in combination or alone with these ligands include, for example, bis (acrylonitrile) nickel, bis (1,5 —Cyclooctagene) Nickel [N i (cod)], bis ( ⁇ -aryl) nickel, nickelocene, nickel-potassium, ( ⁇ -cyclopentenyl) ( ⁇ -aryl) nickel, nickel acetate, nickel bromide And the like.
  • Complexes containing a tertiary phosphine / phosphite as a ligand include, for example, bis (tricyclohexylphosphine) nickel, dichlorobis (triphenylphosphine) nickel, and dimethylbis (diphenylmethylphosphine).
  • a treating agent for lowering the valence depending on the structure of the precursor nickel complex.
  • the treating agent used at that time include a reducing agent and a Grignard reagent, and more specifically, for example, hydrides such as sodium borohydride, aluminum lithium hydride, sodium hydride, and the like. , Triethylaluminum, phenyllithium, butyllithium, metallic lithium, metallic sodium, sodium amalgam, metallic zinc, methylmagnesium bromide, phenylmagnesium iodide, isopropylmagnesium bromide and the like.
  • precursor nickel complex examples include, for example, dichlorobis (triphenylphosphine) nickel, dichlorobis (diphenylmethylphosphine) nickel, dichlorobis (dimethylphenylphosphine) nickel, and chlorobisphenol
  • one or more suitable catalysts are appropriately selected and used according to the reaction.
  • the amount of the nickel catalyst used in the reaction of the present invention may be a so-called catalytic amount, which is less than 20 mol% with respect to the acetylene compound, but usually less than 10 mol% is sufficient.
  • the amount of these trivalent phosphorus compounds when used as a ligand is not particularly strictly limited, but if the atomic ratio of phosphorus to nickel is too large, the catalytic activity tends to decrease. Therefore, it is generally preferable to set the atomic ratio to 50 or less, preferably to 10 or less.
  • Nickel-containing catalysts exhibit activity alone, but can also be used with phosphinic acid additives.
  • phosphinic acid additives In particular, in a reaction in which a regioisomer is generated, regioselectivity is increased by using a phosphinic acid additive in combination.
  • R 5 represents an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group.
  • examples of the alkyl group when R 5 is an alkyl group include an alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Specific examples thereof include a methyl group and Ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl.
  • R 5 is a cycloalkyl group
  • examples of the cycloalkyl group include a cycloalkyl group having 3 to 12 carbon atoms, preferably 5 to 12 carbon atoms. Specific examples thereof include, for example, a cyclopentyl group and a cycloalkyl group. Examples include a hexyl group, a cyclooctyl group, and a cyclododecyl group.
  • R 5 is an aryl group
  • examples of the aryl group include an aryl group having 6 to 14 carbon atoms, preferably 6 to 10 carbon atoms. Specific examples thereof include, for example, a phenyl group and a naphthyl group. And their substituents (tolyl, xylyl, benzylphenyl, etc.) are also included.
  • the aralkyl group may be, for example, a carbon number? To 15, preferably 7 to 11 aralkyl groups, and specific examples thereof include, for example, a benzyl group, a phenethyl group and a naphthylmethyl group.
  • the alkyl group, cycloalkyl group, aryl group or aralkyl group represented by R 5 is a substituent inert to the reaction, for example, a methoxy group, a methoxycarbonyl group, a cyano group, a dimethylamino group, a fluoro group, and a chloro group. And may be substituted with a hydroxy group or the like.
  • phosphinic acid used in the present invention include, for example, diphenylphosphinic acid / dimethylphosphinic acid.
  • the amount of use is not more than equimolar, preferably 0.1 to 10 mol% with respect to the P—H compound used.
  • the reaction does not need to use a solvent, but can be carried out in a solvent if necessary.
  • the solvent include hydrocarbon solvents such as toluene and xylene, ether solvents such as dioxane, tetrahydrofuran (THF), diisopropyl ether, and dimethoxetane; ester solvents such as ethyl acetate and butyl acetate;
  • a variety of solvents can be used, such as ketones such as acetyl ethyl ketone, nitrile solvents such as acetonitril and propiononitrile, and amide solvents such as N, N-dimethylformamide (DMF). These can be used alone or as a mixture of two or more.
  • the reaction temperature is generally selected from the range of —20 ° C. to 300, because the reaction does not proceed at an advantageous rate at a too low temperature, and the catalyst decomposes at a too high temperature. It is performed in the range from 0 to 150.
  • the reaction time varies depending on the kind of the acetylene compound and the PH compound to be used, the reaction temperature and other reaction conditions, but is usually about several hours to several tens of hours.
  • Example 1 The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples.
  • Example 1
  • Example 2 Reaction conditions as in Example 1, using N i (cod) 2 (1 0 mol% and P 11 2? ( ⁇ ? 1 2) 3??
  • Example 2 3
  • Example 2 7 When the reaction of Example 25 was carried out in the coexistence of diphenylphosphinic acid (10 mol%), ethyl (1-phenylphenyl) phenylphosphinate was selectively produced in a yield of 98%. .
  • Example 2 7 When the reaction of Example 25 was carried out in the coexistence of diphenylphosphinic acid (10 mol%), ethyl (1-phenylphenyl) phenylphosphinate was selectively produced in a yield of 98%. .
  • Example 28 The reaction was carried out under the same reaction conditions as in Example 26 but using 1-year-old cutin instead of phenylacetylene.
  • CH 2 C (n—C 6 H 13 ) [P ( ⁇ ) P h ( ⁇ E t)] was selectively produced in a yield of 88%.
  • (E) —CH (S i Me 3 ) CH [P (O) Ph (OEt)] was selectively produced in a yield of 92%.
  • Example 3 1
  • the present invention relates to alkenyl lin compounds (alkenyl phosphonates, alkenyl phosphinates and alkenyl phosphoxides) useful as synthetic intermediates for physiologically active substances such as pharmaceuticals and agricultural chemicals and ligands for preparing catalysts. It is intended to provide a production method with high yield and high practicability.
  • a relatively inexpensive nickel complex catalyst is used as the catalyst, and the acetylene is converted to a PH compound (hydrogenated phosphonate, hydrogenated phosphinate and disubstituted). (Phosphinoxide) can be simply, safely, and efficiently synthesized, and the product can be easily separated and purified. Therefore, the present invention has a great industrial effect.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de production d'un composé d'alcénylphosphore tel qu'un ester alcénylphosphonique, un ester alcénylphosphinique ou un oxyde d'alcénylphosphine, qui se caractérise en ce qu'il consiste à faire réagir un composé d'acétylène avec un ester phosphonique hydrogéné, un ester phosphinique hydrogéné ou un oxyde de phosphine disubstitué, en présence d'un catalyseur contenant du nickel. Ce procédé permet de produire un composé d'alcénylphosphore à partir d'un ester phosphonique hydrogéné, d'un ester phosphinique hydrogéné ou d'un oxyde de phosphine disubstitué utilisés en tant que matériaux de départ, cela avec un catalyseur bon marché.
PCT/JP2003/005807 2002-05-17 2003-05-09 Procede de production d'un compose d'alcenylphosphore WO2003097654A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002142955A JP3836395B2 (ja) 2002-05-17 2002-05-17 アルケニルリン化合物の製造方法
JP2002-142955 2002-05-17

Publications (1)

Publication Number Publication Date
WO2003097654A1 true WO2003097654A1 (fr) 2003-11-27

Family

ID=29545003

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/005807 WO2003097654A1 (fr) 2002-05-17 2003-05-09 Procede de production d'un compose d'alcenylphosphore

Country Status (2)

Country Link
JP (1) JP3836395B2 (fr)
WO (1) WO2003097654A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1528065A1 (fr) * 2003-10-30 2005-05-04 Basf Aktiengesellschaft Procédé de préparation d'un dérivé d'acide alcényl phosphonique
EP1528064A1 (fr) * 2003-10-30 2005-05-04 Basf Aktiengesellschaft Procédé de préparation d'un dérivé d'acide alcényl phosphonique

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3836460B2 (ja) * 2003-09-03 2006-10-25 独立行政法人科学技術振興機構 アルケニルリン化合物を製造する方法
JP4102879B2 (ja) * 2004-02-18 2008-06-18 独立行政法人産業技術総合研究所 有機リン化合物の製造方法
JP2005232065A (ja) * 2004-02-18 2005-09-02 National Institute Of Advanced Industrial & Technology 含リンブタジエン化合物の製造方法
JP3987937B2 (ja) * 2004-03-10 2007-10-10 独立行政法人産業技術総合研究所 含リン有機ポリマーとその製造法
JP5388856B2 (ja) * 2007-10-18 2014-01-15 片山化学工業株式会社 含リン化合物と含イオウ化合物の触媒
KR20140064917A (ko) * 2011-08-31 2014-05-28 말린크로트 엘엘씨 H-포스포네이트-엔/-인 히드로포스포닐화 반응을 이용한 표적화된 나노입자의 원격 어셈블리
JP6209324B2 (ja) * 2012-10-30 2017-10-04 東レエンジニアリング株式会社 マイクロリアクタシステムとそれを用いた化合物製造方法
JP5786269B2 (ja) * 2014-03-07 2015-09-30 国立研究開発法人産業技術総合研究所 アルケニルリン化合物の製造方法、アルケニルリン化合物重合体の製造方法、及びアルケニルリン化合物共重合体の製造方法
JP5880907B2 (ja) * 2015-01-20 2016-03-09 国立研究開発法人産業技術総合研究所 アルケニルリン化合物、アルケニルリン化合物重合体、及びアルケニルリン化合物共重合体
US10479809B2 (en) 2015-09-11 2019-11-19 Maruzen Petrochemical Co., Ltd. Method for producing alkenyl phosphorus compound
US20220212177A1 (en) * 2019-11-27 2022-07-07 Maruzen Petrochemical Co., Ltd. Complex compound and method for manufacturing the same
EP3971193A4 (fr) 2019-11-27 2023-03-15 Maruzen Petrochemical Co., Ltd. Procédé de production d'un composé d'alcénylphosphore
JP7282017B2 (ja) * 2019-11-27 2023-05-26 丸善石油化学株式会社 アルケニルリン化合物の製造方法
CN114031638B (zh) * 2021-12-09 2024-02-20 浙江万盛股份有限公司 一种烷基膦酸二芳基酯的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3673285A (en) * 1969-11-12 1972-06-27 Hooker Chemical Corp Preparation of vinyl organo-phosphorous compounds
EP0794190A1 (fr) * 1996-03-07 1997-09-10 Director-General Of The Agency Of Industrial Science And Technology Procédé de préparation d'oxydes d'alcénylphosphines ou d'oxydes de bis(alcénylphosphines)
EP1203773A1 (fr) * 2000-11-02 2002-05-08 Basf Aktiengesellschaft Procédé pour la préparation de dérivés d'acides alcényl phosphoniques

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2794089B2 (ja) * 1996-03-07 1998-09-03 工業技術院長 アルケニルホスフィンオキシド化合物の製造法
JP3836460B2 (ja) * 2003-09-03 2006-10-25 独立行政法人科学技術振興機構 アルケニルリン化合物を製造する方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3673285A (en) * 1969-11-12 1972-06-27 Hooker Chemical Corp Preparation of vinyl organo-phosphorous compounds
EP0794190A1 (fr) * 1996-03-07 1997-09-10 Director-General Of The Agency Of Industrial Science And Technology Procédé de préparation d'oxydes d'alcénylphosphines ou d'oxydes de bis(alcénylphosphines)
EP1203773A1 (fr) * 2000-11-02 2002-05-08 Basf Aktiengesellschaft Procédé pour la préparation de dérivés d'acides alcényl phosphoniques

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1528065A1 (fr) * 2003-10-30 2005-05-04 Basf Aktiengesellschaft Procédé de préparation d'un dérivé d'acide alcényl phosphonique
EP1528064A1 (fr) * 2003-10-30 2005-05-04 Basf Aktiengesellschaft Procédé de préparation d'un dérivé d'acide alcényl phosphonique
US7399876B2 (en) 2003-10-30 2008-07-15 Basf Aktiengesellschaft Preparation of an alkenylphosphonic acid derivative

Also Published As

Publication number Publication date
JP2004026655A (ja) 2004-01-29
JP3836395B2 (ja) 2006-10-25

Similar Documents

Publication Publication Date Title
EP1369422B1 (fr) Procede de preparation d'oxydes d'alcenylphosphine ou d'esters alcenylphosphiniques
WO2003097654A1 (fr) Procede de production d'un compose d'alcenylphosphore
JP3836460B2 (ja) アルケニルリン化合物を製造する方法
JP3836459B2 (ja) アルケニルホスホン酸エステルの製造方法
JP3662501B2 (ja) アルケニルホスフィンオキシド類の製造方法
JP4314366B2 (ja) 含リンブタジエン化合物の製造方法
JP4280307B2 (ja) ビニルホスホン酸化合物の製造方法
JP3564503B2 (ja) アルケニルホスホン酸エステル類およびその製造方法
JP3877151B2 (ja) アルケニルホスフィン酸エステル類の製造方法
JP4863258B2 (ja) リン化合物およびその製造方法
JP3390399B2 (ja) ホスホン酸エステル類の製造方法
JP3007984B1 (ja) 不飽和ホスホン酸エステルの製造方法
JP4102879B2 (ja) 有機リン化合物の製造方法
JPH09241276A (ja) アルケニルホスフィンオキシド化合物の製造法
JP2002518507A (ja) ビニルホスホン酸化合物の製造方法
JP4572391B2 (ja) ビスホスフィノイルアミノメタン類の製造方法
JP3987937B2 (ja) 含リン有機ポリマーとその製造法
JP3572352B2 (ja) アリルホスホン酸エステル化合物及びその製造方法
JP2775426B2 (ja) 不飽和ホスホン酸エステルの製造方法
JP3610371B2 (ja) （α−及び／又はβ−ホルミルエチル）ホスフィンオキシド化合物、（α−及び／又はβ−ホルミルエチル）ホスホン酸エステル化合物とその製造方法
WO2002072592A1 (fr) Ester d'acide alcenylphosphinique et son procede d'obtention
JP3413386B2 (ja) アリルホスホン酸エステル化合物の製造方法
US6765107B2 (en) Method for manufacturing phosphonate esters
JP2005232065A (ja) 含リンブタジエン化合物の製造方法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase