CN113372386A - Process for preparing organic phosphine-hydrogen compound - Google Patents

Process for preparing organic phosphine-hydrogen compound Download PDF

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CN113372386A
CN113372386A CN202010141500.2A CN202010141500A CN113372386A CN 113372386 A CN113372386 A CN 113372386A CN 202010141500 A CN202010141500 A CN 202010141500A CN 113372386 A CN113372386 A CN 113372386A
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trichlorosilane
phosphine
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王智刚
王健
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Shenzhen Youwei Technology Holding Co ltd
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    • 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
    • C07F9/505—Preparation; Separation; Purification; Stabilisation
    • 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
    • C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives 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 Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5004—Acyclic saturated phosphines
    • 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
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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    • 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
    • C07F9/5031—Arylalkane phosphines
    • 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
    • C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
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    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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Abstract

The invention relates to the field of organic functional new material chemicals, and discloses a novel method for generating a corresponding organic phosphine hydrogen (containing a P-H bond) product from an organic phosphine halide (containing a P-X bond) compound through reduction of trichlorosilane for the first time. The organophosphine hydrogen products are known to be high value-added fine chemicals for an extremely wide range of uses.

Description

Process for preparing organic phosphine-hydrogen compound
[ technical field ] A method for producing a semiconductor device
The invention relates to the field of organic functional new material chemicals, and discloses a novel method for generating a corresponding organic phosphine hydrogen (containing a P-H bond) product from an organic phosphine halide (containing a P-X bond) compound through reduction of trichlorosilane for the first time. The organophosphine hydrogen products are known to be high value-added fine chemicals for an extremely wide range of uses.
[ background of the invention ]
The organic phosphine-hydrogen compound containing active phosphine-hydrogen (P-H) bond is a novel material fine chemical with high added value and can be widely used for preparing phosphonyl type photoinitiator, low-smoke halogen-free flame retardant, electronic chemicals, pesticide, medical chemicals and the like. It is generally prepared industrially by chemical reduction of cheap and readily available precursors of organophosphinic halides (P-X), known reducing agents such as lithium aluminium hydride or metallic sodium in solid form, belonging to expensive and extremely moisture and air sensitive materials, safety risks in production operations and high operating costs. However, in view of the particularity of the reduction of the halogen bond of phosphine, no reducing agent system with higher safety and efficiency and lower cost has been found, which is one of the major technical bottlenecks in the industry.
[ summary of the invention ]
The present application has now for the first time surprisingly found that the following reaction scheme(I) In the form of R1R2Organic phosphine halide compound of PX in trichlorosilane (HSiCl)3) And the reduction under the conditions of proper reaction conditions can prepare the corresponding organic phosphine product R with high efficiency, cleanness and low cost1R2And (4) pH. It is worth noting that trichlorosilane itself is an extremely cheap bulk industrial raw material, and the raw materials and reagents involved in the process are generally liquid, can be conveniently transported by pipelines and operated in an unmanned automatic mode, and is a revolution of the preparation technology of organic phosphine compounds.
Figure BSA0000203261770000011
Wherein X is halogen chlorine, bromine, iodine, fluorine; r1And R2Each independently is halogen, or a straight or branched chain alkyl group having 1 to 24 carbon atoms, or a substituted or unsubstituted (hetero) aryl group having 4 to 24 carbon atoms; the amount of trichlorosilane used is 1 to 100 molar equivalents, preferably 1 to 50 molar equivalents, and more preferably 1 to 20 molar equivalents. Trichlorosilane may serve as both a reducing agent and a solvent in the present reaction.
The conditions are any one or a combination of any two or more of solvents, temperatures, pressures, and/or additives.
The reaction solvent involved in the process is selected from substituted or unsubstituted aromatic hydrocarbon containing 1-24 carbon atoms, straight-chain or branched-chain aliphatic hydrocarbon, amide, ether, ester, ketone, nitrile, carboxylic acid, water, amine, ionic liquid, supercritical carbon dioxide, or a mixed solvent consisting of any two or more of the above solvents; preferred solvents are trichlorosilane, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, trimethylbenzene, tetramethylbenzene, acetonitrile, ethylbenzene, diethylbenzene, chlorobenzene, dichlorobenzene, anisole, nitrobenzene, heptane, hexane, petroleum ether, dioxane, tetrahydrofuran, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, propylene glycol methyl ether acetate, triethylamine, tributylamine, dimethylisopropylamine, pyridine, N, N-tetramethylethylenediamine, N-alkylmorpholine, N-alkylpyrrole, N, N-dimethylformamide, formylmorpholine, N, N-diethylformamide, N-methylpyrrolidone, or a mixed solvent of any two or more of the above solvents.
The reaction temperature involved in the process is selected from-70 ℃ to 200 ℃, preferably from-30 ℃ to 180 ℃, and more preferably from-20 ℃ to 150 ℃.
The "pressure" of the reaction involved in the process is selected from between 0.001 and 200 atm, preferably from between 0.1 and 100 atm, more preferably from between 0.1 and 20 atm.
The reaction "additives" referred to in the present process encompass reaction promoters, synergists, catalysts, and/or functional auxiliaries which are Lewis acid or Lewis base type (Lewis acids/bases) simple substances or compounds, preferably fluorides, chlorides, bromides, iodides, oxides, hydroxides, sulfides, alkoxides, alkyl or aryl metal compounds of organic (tertiary) amines, alkali metals, alkaline earth metals, main group metals, or transition metals; or an alkali metal, alkaline earth metal, main group metal, or transition metal carbonate, bicarbonate, sulfite, bisulfate, sulfonate, or carboxylate; or a mono-or polyvalent organic phosphorus of an alkali metal, alkaline earth metal, or transition metal, organic amine, hydroxyl, ketocarbonyl, ester carbonyl, or carboxylic acid ligand; or tetraalkylammonium halides, tetraalkylammonium hydroxides, or Ionic Liquids (Ionic Liquids); or inorganic protonic acids, organic carboxylic acids, organic sulfonic acids, heteropolyacids, molecular sieves, zeolites, diatomaceous earth, montmorillonite, kaolin; or fluorides, chlorides, bromides, iodides, oxides, hydroxides, sulfides, alkoxides of boron, silicon, phosphorus elements; or a mixture of any two or more of the above "additives" or a combination thereof which satisfies the above definition. The "additive" may be used in a catalytic amount, an equivalent amount, or an excess amount, based on the molar equivalents of the reaction starting materials.
In view of the organic phosphine hydrogen compound and acylThe condensation of chlorine under the acceleration of alkali to produce acylphosphine intermediate (patent CN1198831) and further oxidation to acylphosphine Oxide (Acylphosphine Oxide) product is a known technique in the literature, and the disclosed process can be directly used for preparing bisacylphosphine Oxide photoinitiator A (reaction formula II), monoacylphosphine Oxide photoinitiator B (reaction formula III) and simultaneously co-producing the above compounds A and B (reaction formula IV) by a one-pot method. Where Ar is aryl or tert-butyl, preferred Ar is 2, 4, 6-trimethylbenzoyl; base is an inorganic base or an organic tertiary amine; [ O ] is an oxidizing agent, preferably H2O2Or O2。
Figure BSA0000203261770000031
In the examples we will further illustrate.
[ detailed description ] embodiments
The first embodiment is as follows: synthesis of phenylphosphines
Figure BSA0000203261770000041
Under the protection of nitrogen, 17.9 g of monophenyl phosphorus dichloride and 300ml of acetonitrile are added into a 1L three-neck flask, 32.3 g of diisopropyl ethylamine is added at room temperature, 33.9 g of trichlorosilane is dropwise added into 100ml of acetonitrile solution under ice bath, and the mixture is slowly raised from 0 ℃ to 80 ℃ after the addition is finished, and is stirred and reacted overnight. Then cooling the reaction system to 0 ℃, slowly adding 300mL of saturated potassium hydroxide solution which is carefully deoxidized in advance, extracting with deoxidized ethyl acetate, washing the organic phase with deoxidized saturated saline solution, and MgSO 24Drying, concentrating to obtain light yellow crude product, and vacuum distilling to obtain target product-phenylphosphine 9.13 g with yield of 83% (nuclear magnetic resonance)31P-NMR characteristic absorption peak at-122.7 ppm). The tertiary amine auxiliary agent, namely the diisopropylethylamine can be recycled and reused in the process of reduced pressure distillation.
Example two: synthesis of phenylphosphines
Figure BSA0000203261770000042
Under the protection of nitrogen, 35.8 g of monophenyl phosphorus dichloride and 500 ml of tetrahydrofuran are added into a 2L three-necked bottle, 64.6 g of diisopropyl ethylamine is added at room temperature, 67.8 g of trichlorosilane in 200 ml of tetrahydrofuran solution is dropwise added in an ice bath, and the temperature is slowly increased from 0 ℃ to reflux and stirred for reaction overnight after the addition is finished. Subsequently, 500 ml of a saturated potassium hydroxide solution which had been previously subjected to deoxidation treatment was added to the reaction system, extraction was carried out with deoxyethyl acetate, and the organic phase was washed with a deoxygenated saturated brine and MgSO4Drying and concentrating to obtain a crude product. The crude product was then distilled under reduced pressure to give the desired product, 19.1 g, 87% yield.
Example three: synthesis of diphenylphosphine
Figure BSA0000203261770000051
Under the protection of nitrogen, 22 g of diphenyl phosphorus chloride and 300ml of tetrahydrofuran are added into a 1L three-neck flask, 19.4 g of diisopropylethylamine is added at room temperature, 20.3 g of trichlorosilane in 100ml of tetrahydrofuran solution is added dropwise in an ice bath, and after the addition, the temperature is slowly increased from 0 ℃ to reflux and the reaction is stirred overnight. Then, 300mL of a saturated KOH solution which had been carefully deoxygenated beforehand was added to the reaction system, extraction was carried out with deoxygenated ethyl acetate, and the organic phase was washed with deoxygenated saturated brine and MgSO4Drying and concentrating to obtain a crude product. Then the crude product is distilled under reduced pressure to obtain 16.9 g of target product diphenylphosphine with the yield of 91% (nuclear magnetic resonance)31P-NMR characteristic absorption peak at-40.4 ppm).
Example four: diphosphonoxy photoinitiator 819 (Ar ═ 2, 4, 6-trimethylbenzoyl)
Figure BSA0000203261770000052
Referring to the procedure of example one, 2.5 g of freshly prepared and distillatively purified phenylphosphine was directly received in 120mL of a xylene cold trap solution, 4.5 g of sodium tert-butoxide and 9.1 g of 2, 4, 6-trimethylbenzoyl chloride were added thereto in portions in this order at room temperature under nitrogen, the reaction was stirred for 2 hours, concentrated sulfuric acid was added dropwise to adjust the system to acidity, and 7mL of 30% hydrogen peroxide was further slowly added dropwise. The system was diluted with 20mL of water, the organic phase was separated and washed twice with 10% sodium bicarbonate solution and water, respectively, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to give a bright yellow solid which was slurried with hexane to give 8.8 g of the target product as a powder.
Example five: synthesis of monophosphoryl oxygen photoinitiator TPO (Ar ═ 2, 4, 6-trimethylbenzoyl)
Figure BSA0000203261770000053
Referring to the procedure of example three, 3.6 g of freshly prepared and distillatively purified diphenylphosphine was directly received in 100mL of a xylene cold trap solution, to which was sequentially added 2.0 g of sodium tert-butoxide and 3.7 g of 2, 4, 6-trimethylbenzoyl chloride in portions at room temperature under nitrogen, stirred to react for 2 hours, concentrated sulfuric acid was added dropwise to adjust the system to acidity, and further 4.5mL of 30% hydrogen peroxide was slowly added dropwise. The system is diluted by 30mL of water, the organic phase is separated and washed twice by 10 percent sodium bicarbonate solution and water respectively, the organic phase is dried by anhydrous sodium sulfate, filtered and concentrated under reduced pressure, and light yellow solid is obtained and crystallized by ethanol to obtain 6.2 g of a target product.
Example six: "one pot" co-production of TPO and 819 (Ar ═ 2, 4, 6-trimethylbenzoyl)
Figure BSA0000203261770000061
Referring to the procedure conditions of the above example, a mixture of 20.2 g of phenylphosphonic dichloride and 25.0 g of diphenylphosphine chloride and a mixture of phenylphosphine and diphenylphosphine obtained by "one-pot" reduction of 73 g of trichlorosilane were directly distilled under reduced pressure into 800mL of a xylene cold trap solution, 35 g of sodium tert-butoxide and 65 g of 2, 4, 6-trimethylbenzoyl chloride were sequentially added in portions under room temperature and nitrogen, stirred for reaction for 4 hours, concentrated sulfuric acid was added dropwise to adjust the system to be acidic, and 140mL of 30% hydrogen peroxide was further slowly added dropwise. The system was diluted with approximately half of the water, the organic phase was separated and washed twice with 10% sodium bicarbonate solution and water, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, the resulting viscous yellow liquid was slurried with hexane to give a yellow solid powder, which was dried to give 71.2 g of a mixture of the target product 819 and TPO in 46/54% by weight.
It should be emphasized that the above-described embodiments are merely illustrative and not restrictive, and that any adjustments or variations, such as reaction conditions or parameters, which may be commonly employed by a person skilled in the art based on the disclosure of this application do not depart from the gist of the present invention, and the scope of protection of this patent shall be governed by the terms of the relevant claims.

Claims (9)

1. The form shown in the reaction formula (I) is R1R2Organic phosphine halide compound of PX in trichlorosilane (HSiCl)3) And reducing under appropriate reaction conditions to prepare the corresponding organic phosphine product R1R2A PH process technology; wherein X is halogen chlorine, bromine, iodine, fluorine; r1And R2Each independently is halogen, or a straight or branched chain alkyl group having 1 to 24 carbon atoms, or a substituted or unsubstituted (hetero) aryl group having 4 to 24 carbon atoms; conditions are any one or a combination of any two or more of solvents, temperatures, pressures, and/or additives:
Figure FSA0000203261760000011
2. the process according to claim 1, wherein the trichlorosilane is used in an amount of 1 to 100 molar equivalents, preferably 1 to 50 molar equivalents, more preferably 1 to 20 molar equivalents; alternatively, the amount of trichlorosilane used is not limited by molar equivalents, and may serve as both a reducing agent and a solvent in the present reaction.
3. The process according to claim 1, wherein the "solvent" is selected from the group consisting of substituted or unsubstituted aromatic hydrocarbons having 1 to 24 carbons, linear or branched aliphatic hydrocarbons, amides, ethers, esters, ketones, nitriles, carboxylic acids, water, amines, ionic liquids, supercritical carbon dioxide, and mixtures of any two or more thereof; preferred solvents are trichlorosilane, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, trimethylbenzene, tetramethylbenzene, acetonitrile, ethylbenzene, diethylbenzene, chlorobenzene, dichlorobenzene, anisole, nitrobenzene, heptane, hexane, petroleum ether, dioxane, tetrahydrofuran, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, propylene glycol methyl ether acetate, triethylamine, tributylamine, dimethylisopropylamine, pyridine, N, N-tetramethylethylenediamine, N-alkylmorpholine, N-alkylpyrrole, N, N-dimethylformamide, formylmorpholine, N, N-diethylformamide, N-methylpyrrolidone, or a mixed solvent of any two or more of the above solvents.
4. The process according to claim 1, wherein the reaction "temperature" is chosen from the range of-70 ℃ to 200 ℃, preferably from the range of-30 ℃ to 180 ℃, and more preferably from the range of-20 ℃ to 150 ℃.
5. The process according to claim 1, wherein the reaction "pressure" is selected from the range of 0.001 to 200 atm, preferably from 0.1 to 100 atm, more preferably from 0.1 to 20 atm.
6. The preparation process as described in claim 1, the reaction "additive" encompasses reaction promoters, synergists, catalysts, and/or functional auxiliaries which are Lewis acid or Lewis base type (Lewis acids/bases) elements or compounds, preferably fluorides, chlorides, bromides, iodides, oxides, hydroxides, sulfides, alkoxides, alkyl or aryl metal compounds of organic (tertiary) amines, alkali metals, alkaline earth metals, main group metals, or transition metals; or an alkali metal, alkaline earth metal, main group metal, or transition metal carbonate, bicarbonate, sulfite, bisulfate, sulfonate, or carboxylate; or a mono-or polyvalent organic phosphorus of an alkali metal, alkaline earth metal, or transition metal, organic amine, hydroxyl, ketocarbonyl, ester carbonyl, or carboxylic acid ligand; or tetraalkylammonium halides, tetraalkylammonium hydroxides, or Ionic Liquids (Ionic Liquids); or inorganic protonic acids, organic carboxylic acids, organic sulfonic acids, heteropolyacids, molecular sieves, zeolites, diatomaceous earth, montmorillonite, kaolin; or fluorides, chlorides, bromides, iodides, oxides, hydroxides, sulfides, alkoxides of boron, silicon, phosphorus elements; or a mixture of any two or more of the above "additives" or a combination thereof which satisfies the above definition. The "additive" may be used in a catalytic amount, an equivalent amount, or an excess amount, based on the molar equivalents of the reaction starting materials.
7. The process according to claim 1, wherein the acylphosphine intermediate is prepared by condensation of the aryl acid chloride with the aid of a base, from the mono (bis) phosphine halide intermediate obtained by reacting the corresponding mono (bis) phosphine halide with trichlorosilane under conditions, and reoxidation of the acylphosphine intermediate to give the mono (bis) acylphosphine oxide photoinitiator compounds B and A. The disclosed process can be directly used for respectively preparing a bisacylphosphine oxide photoinitiator A (reaction formula II) and a monoacylphosphine oxide photoinitiator B (reaction formula III); the above-mentioned compounds A and B (reaction formula IV) can also be co-produced simultaneously in a "one-pot" process.
Where Ar is aryl or tert-butyl, preferred Ar is 2, 4, 6-trimethylbenzoyl; base is an inorganic base or an organic tertiary amine; [ O ] is an oxidizing agent, preferably H2O2Or O2。
Figure FSA0000203261760000031
8. An organic phosphine compound R containing an active phosphine-hydrogen (P-H) bond prepared by the preparation method as described in claim 11R2The PH can be used for manufacturing phosphonyl type photoinitiators, low-smoke halogen-free flame retardants, electronic chemicals, pesticides and medicinal chemical products.
9. According to the preparation methods described in claims 1 and 8, the following target compounds were prepared:
Figure FSA0000203261760000032
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4536350A (en) * 1982-09-28 1985-08-20 Hoechst Aktiengesellschaft Process for making chlorophosphanes, phosphinic acid chlorides or thiophosphinic acid chloride, and novel isomeric mixture consisting of chloro-phosphabicyclononanes
CN105884824A (en) * 2014-10-16 2016-08-24 郑成 Preparation method of acyl phosphine (oxygen) or sulfonyl phosphine (oxygen) compounds
CN106478716A (en) * 2016-09-18 2017-03-08 江苏欣诺科催化剂有限公司 A kind of synthetic method of organic phosphorus compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4536350A (en) * 1982-09-28 1985-08-20 Hoechst Aktiengesellschaft Process for making chlorophosphanes, phosphinic acid chlorides or thiophosphinic acid chloride, and novel isomeric mixture consisting of chloro-phosphabicyclononanes
CN105884824A (en) * 2014-10-16 2016-08-24 郑成 Preparation method of acyl phosphine (oxygen) or sulfonyl phosphine (oxygen) compounds
CN106478716A (en) * 2016-09-18 2017-03-08 江苏欣诺科催化剂有限公司 A kind of synthetic method of organic phosphorus compound

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HANS FRITZSCHE等: ""Darstellung primarer und sekundarer Phosphine mit Silanen"", 《FRITZSCHE, HA SSEROD UND KORTE》, pages 1681 - 1687 *
VOLKER PLACK等: ""Organophosphorverbindungen mit tertiaren Alkylsubstituenten. V [I]Synthese und Reaktionen triphenylmethyl-substituierter Dihalogenphosphine TrtPX, (Trt = Triphenylmethyl-, X = F, C1, Br); Kristallstrukturen von Triphenylmethyldichlorphosphin TrtPC1, und Triphenylmethylthiophosphonsauredifluorid Trt", 《Z. ANORG. ALLG. CHEM.》, vol. 621, pages 1080 - 1092 *
WOLF-WALTHER DU MONT等: ""Extension of the Benkeser reaction to the reducfive trichlorosilylafion of main group element chlorides"", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》, vol. 521, pages 417 - 419 *

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