CN112142789A - Production method of alkyl phosphine - Google Patents
Production method of alkyl phosphine Download PDFInfo
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- CN112142789A CN112142789A CN201910570079.4A CN201910570079A CN112142789A CN 112142789 A CN112142789 A CN 112142789A CN 201910570079 A CN201910570079 A CN 201910570079A CN 112142789 A CN112142789 A CN 112142789A
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- initiator
- solvent
- phosphine
- free radical
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims abstract description 48
- -1 alkyl phosphine Chemical compound 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 239000003999 initiator Substances 0.000 claims abstract description 41
- 239000002994 raw material Substances 0.000 claims abstract description 27
- 239000003960 organic solvent Substances 0.000 claims abstract description 24
- 150000003254 radicals Chemical class 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 16
- 150000001336 alkenes Chemical class 0.000 claims abstract description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- 238000002156 mixing Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012934 organic peroxide initiator Substances 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 abstract description 5
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
- C07F9/50—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 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
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5072—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure P-H
Abstract
The invention discloses a method for producing alkyl phosphine, which comprises the steps of taking phosphine and olefin as raw materials, dissolving the raw materials in a solvent, and reacting in the solvent under the conditions of heating and pressurizing under the action of an initiator to generate trialkyl phosphine; wherein the solvent is an organic solvent and water according to the volume ratio (2-5): 1, wherein the initiator is an oil-soluble free radical initiator and an organic water-soluble free radical initiator according to a molar ratio (2-5): 1, a mixed initiator. The traditional organic solvent is improved into a mixed solvent of the organic solvent and the aqueous solution, so that the dosage and toxicity of the organic solvent are reduced to a certain extent on the basis of ensuring the original reaction efficiency, yield and production cost, and the safe protection and sustainable development of the production environment are facilitated.
Description
Technical Field
The invention belongs to the technical field of chemical production, and particularly relates to a production method of alkyl phosphine.
Background
The alkyl phosphine is also called trialkyl phosphine, is generally colorless liquid or crystal, is easy to dissolve in organic solvents such as diethyl ether, chloroform, benzene, ethanol and the like, is insoluble in water and is extremely toxic. Can be used as reducing agent, olefin polymerization catalyst and hydrogenation catalyst active component, etc.
The usual prior art processes for preparing alkyl phosphines are the grignard reagent process: magnesium reacts with alkyl in ether solution to generate Grignard reagent, phosphorus trichloride ether solution is dripped into the reactant, ice water is used for cooling, reflux reaction is carried out, diluted hydrochloric acid is used for processing, and the finished product is obtained through ether extraction, washing, drying, filtering and reduced pressure distillation. The method has complex procedures and low efficiency, and needs to be improved urgently.
Disclosure of Invention
The purpose of the invention is as follows: in order to overcome the defects in the prior art, the invention provides a method for producing alkyl phosphine, which reduces the dosage and toxicity of organic solvent and is beneficial to the safety protection and sustainable development of production environment.
The technical scheme is as follows: in order to achieve the purpose, the invention adopts the following technical scheme:
a method for producing alkyl phosphine, take phosphine and alkene as raw materials, dissolve in solvent, under the condition of heating, pressurizing, react in solvent under the influence of initiating agent to produce trialkyl phosphine; wherein the solvent is an organic solvent and water according to the volume ratio (2-5): 1, wherein the initiator is an oil-soluble free radical initiator and an organic water-soluble free radical initiator according to a molar ratio (2-5): 1, a mixed initiator.
Further, in the invention, the organic solvent is selected from one or more of diethyl ether, anisole, tetrahydrofuran, n-butyl ether, petroleum ether or C6-C9 n-alkane.
Further, in the present invention, the organic water-soluble radical initiator is a water-soluble azo-based radical initiator such as azobisisobutyronitrile, azobisisoheptonitrile, and dimethyl azobisisobutyrate initiator; the oil-soluble free radical initiator is an organic peroxide initiator, such as benzoyl peroxide, benzoyl tert-butyl peroxide, methyl ethyl ketone peroxide and the like.
Further, the invention specifically comprises the following steps:
step one, preparing a solvent: mixing an organic solvent and water according to a volume ratio, and placing the mixture in a high-pressure reaction kettle;
step two, dissolving raw materials: adding phosphine and olefin raw materials into a high-pressure reaction kettle, and uniformly mixing; adding an initiator, and uniformly mixing;
step three, raw material reaction: starting a temperature rise and pressure rise program, and carrying out temperature rise and pressure rise on reactants in the high-pressure reaction kettle to enable the raw materials to react for 1.5-2 hours to obtain alkyl phosphine;
step four, post-treatment: and cooling and refluxing the alkyl phosphine product obtained in the step three through ice water, extracting, washing, drying, filtering and distilling under reduced pressure to obtain the final product alkyl phosphine.
Further, in the present invention, in the third step, the temperature raising program of the reaction is set as: heating from 60 ℃ to 120 ℃ according to the heating rate of 0.5-2 ℃/min, keeping the constant temperature of 120 ℃ for 20-30min, and then cooling to 80-100 ℃ until the reaction is finished.
Further, in the present invention, in step three, the pressurization procedure of the reaction is set as follows: pressurizing from 1 MPa to 10MPa according to the pressure increasing rate of 0.2-0.5 MPa/min, and then keeping the pressure constant at 10MPa until the reaction is finished.
Further, in the invention, in the third step, diethyl ether is used for extraction.
Has the advantages that: compared with the prior art, the production method of alkyl phosphine has the following advantages: the traditional organic solvent is improved into a mixed solvent of the organic solvent and the aqueous solution, so that the dosage and toxicity of the organic solvent are reduced to a certain extent on the basis of ensuring the original reaction efficiency, yield and production cost, and the safe protection and sustainable development of the production environment are facilitated.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
A method for producing alkyl phosphine takes phosphine and olefin as raw materials, and the phosphine and the olefin are dissolved in an organic solvent and water according to the volume ratio of 2:1 under the conditions of heating and pressurizing, adding an oil-soluble free radical initiator and an organic water-soluble free radical initiator according to a molar ratio of 2:1 in a mixed solvent to generate trialkyl phosphine.
Wherein the organic solvent is a mixture of diethyl ether and C6-C9 n-alkane according to the volume ratio of 1: 1.
Preferably, the organic water-soluble free radical initiator is dimethyl azodiisobutyrate initiator; the oil-soluble free radical initiator is benzoyl peroxide.
The method specifically comprises the following steps:
step one, preparing a solvent: mixing an organic solvent and water in a volume ratio of 2:1, mixing and placing in a high-pressure reaction kettle;
step two, dissolving raw materials: adding phosphine and olefin raw materials into a high-pressure reaction kettle, and uniformly mixing; adding an initiator, and uniformly mixing;
step three, raw material reaction: starting a temperature rise and pressure rise program, and carrying out temperature rise and pressure rise on reactants in the high-pressure reaction kettle to enable the raw materials to react for 1.5-2 hours to obtain alkyl phosphine;
the temperature program of the reaction was set as: heating from 60 ℃ to 120 ℃ according to the heating rate of 1 ℃/min, keeping the constant temperature of 120 ℃ for 26min, and then cooling to 90 ℃ until the reaction is finished.
The pressurization program of the reaction was set to: pressurizing from 1 MPa to 10MPa according to the boosting rate of 0.4 MPa/min, and then keeping the constant pressure of 10MPa until the reaction is finished;
step four, post-treatment: and cooling the alkyl phosphine product obtained in the third step by using ice water, refluxing, extracting by using diethyl ether, washing, drying, filtering, and distilling under reduced pressure to obtain the final product alkyl phosphine.
Example 2
A method for producing alkyl phosphine takes phosphine and olefin as raw materials, and the phosphine and the olefin are dissolved in an organic solvent and water according to the volume ratio of 5: 1 under the conditions of heating and pressurizing, adding an oil-soluble free radical initiator and an organic water-soluble free radical initiator in a molar ratio of 5: 1 in a mixed solvent to generate trialkyl phosphine.
Wherein the organic solvent is a mixture of tetrahydrofuran and n-butyl ether according to the volume ratio of 2: 1.
Preferably, the organic water-soluble free radical initiator is formed by mixing azodiisobutyronitrile and azodiisoheptonitrile; the oil-soluble free radical initiator is a mixture of benzoyl tert-butyl peroxide and methyl ethyl ketone peroxide.
The method specifically comprises the following steps:
step one, preparing a solvent: mixing an organic solvent and water in a volume ratio of 5: 1, mixing and placing in a high-pressure reaction kettle;
step two, dissolving raw materials: adding phosphine and olefin raw materials into a high-pressure reaction kettle, and uniformly mixing; adding an initiator, and uniformly mixing;
step three, raw material reaction: starting a temperature rise and pressure rise program, and carrying out temperature rise and pressure rise on reactants in the high-pressure reaction kettle to enable the raw materials to react for 2 hours to obtain alkyl phosphine;
the temperature program of the reaction was set as: heating from 60 ℃ to 120 ℃ according to the heating rate of 0.5/min, keeping the constant temperature of 120 ℃ for 20min, and then cooling to 100 ℃ until the reaction is finished.
The pressurization program of the reaction was set to: pressurizing from 1 MPa to 10MPa according to the boosting rate of 0.5 MPa/min, and then keeping the constant pressure of 10MPa until the reaction is finished;
step four, post-treatment: and cooling the alkyl phosphine product obtained in the third step by using ice water, refluxing, extracting by using diethyl ether, washing, drying, filtering, and distilling under reduced pressure to obtain the final product alkyl phosphine.
Example 3
A method for producing alkyl phosphine takes phosphine and olefin as raw materials, and the phosphine and the olefin are dissolved in an organic solvent and water according to the volume ratio of 4: 1 under the conditions of heating and pressurizing, adding an oil-soluble free radical initiator and an organic water-soluble free radical initiator in a molar ratio of 4: 1 in a mixed solvent to generate trialkyl phosphine.
Wherein the organic solvent is a mixture of n-butyl ether and petroleum ether according to the volume ratio of 1: 1.
Preferably, the organic water-soluble free radical initiator is an azobisisoheptonitrile initiator; the oil-soluble free radical initiator is formed by mixing benzoyl peroxide tert-butyl ester and methyl ethyl ketone peroxide.
The method specifically comprises the following steps:
step one, preparing a solvent: mixing an organic solvent and water in a volume ratio of 4: 1, mixing and placing in a high-pressure reaction kettle;
step two, dissolving raw materials: adding phosphine and olefin raw materials into a high-pressure reaction kettle, and uniformly mixing; adding an initiator, and uniformly mixing;
step three, raw material reaction: starting a temperature rise and pressurization program, and carrying out temperature rise and pressurization on reactants in the high-pressure reaction kettle to enable the raw materials to react for 1.5 to obtain alkyl phosphine;
the temperature program of the reaction was set as: heating from 60 ℃ to 120 ℃ according to the heating rate of 2 ℃/min, keeping the temperature of 120 ℃ for 30min, and then cooling to 80 ℃ until the reaction is finished.
The pressurization program of the reaction was set to: pressurizing from 1 MPa to 10MPa according to the boosting rate of 0.2 MPa/min, and then keeping the constant pressure of 10MPa until the reaction is finished;
step four, post-treatment: and cooling the alkyl phosphine product obtained in the third step by using ice water, refluxing, extracting by using diethyl ether, washing, drying, filtering, and distilling under reduced pressure to obtain the final product alkyl phosphine.
The above description is only of the preferred embodiments of the present invention, and it should be noted that: it will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the principles of the invention and these are intended to be within the scope of the invention.
Claims (8)
1. A method for producing alkyl phosphine, which is characterized in that: phosphine and olefin are taken as raw materials, dissolved in a solvent, and reacted in the solvent under the conditions of heating and pressurizing under the action of an initiator to generate trialkyl phosphine; wherein the solvent is an organic solvent and water according to the volume ratio (2-5): 1, wherein the initiator is an oil-soluble free radical initiator and an organic water-soluble free radical initiator according to a molar ratio (2-5): 1, a mixed initiator.
2. The process for producing an alkylphosphine according to claim 1, wherein: the organic solvent is one or more selected from diethyl ether, anisole, tetrahydrofuran, n-butyl ether, petroleum ether or C6-C9 n-alkane.
3. The process for producing an alkylphosphine according to claim 1, wherein: the organic water-soluble free radical initiator is a water-soluble azo free radical initiator and is selected from at least one of azodiisobutyronitrile, azodiisoheptonitrile and dimethyl azodiisobutyrate initiator.
4. The process for producing an alkylphosphine according to claim 1, wherein: the oil-soluble free radical initiator is an organic peroxide initiator and is selected from at least one of benzoyl peroxide, benzoyl tert-butyl peroxide and methyl ethyl ketone peroxide.
5. The process for producing an alkylphosphine according to claim 1, wherein: the method specifically comprises the following steps:
step one, preparing a solvent: mixing an organic solvent and water according to a volume ratio, and placing the mixture in a high-pressure reaction kettle;
step two, dissolving raw materials: adding phosphine and olefin raw materials into a high-pressure reaction kettle, and uniformly mixing; adding an initiator, and uniformly mixing;
step three, raw material reaction: starting a temperature rise and pressure rise program, and carrying out temperature rise and pressure rise on reactants in the high-pressure reaction kettle to enable the raw materials to react for 1.5-2 hours to obtain alkyl phosphine;
step four, post-treatment: and cooling and refluxing the alkyl phosphine product obtained in the step three through ice water, extracting, washing, drying, filtering and distilling under reduced pressure to obtain the final product alkyl phosphine.
6. The process for producing an alkylphosphine according to claim 5, wherein: in the third step, the temperature rise program of the reaction is set as follows: heating from 60 ℃ to 120 ℃ according to the heating rate of 0.5-2 ℃/min, keeping the constant temperature of 120 ℃ for 20-30min, and then cooling to 80-100 ℃ until the reaction is finished.
7. The process for producing an alkylphosphine according to claim 5, wherein: in the third step, the pressurization program of the reaction is set as follows: pressurizing from 1 MPa to 10MPa according to the pressure increasing rate of 0.2-0.5 MPa/min, and then keeping the pressure constant at 10MPa until the reaction is finished.
8. The process for producing an alkylphosphine according to claim 5, wherein: in the third step, ether is adopted for extraction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910570079.4A CN112142789A (en) | 2019-06-27 | 2019-06-27 | Production method of alkyl phosphine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910570079.4A CN112142789A (en) | 2019-06-27 | 2019-06-27 | Production method of alkyl phosphine |
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| CN112142789A true CN112142789A (en) | 2020-12-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910570079.4A Pending CN112142789A (en) | 2019-06-27 | 2019-06-27 | Production method of alkyl phosphine |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4757156A (en) * | 1986-08-28 | 1988-07-12 | Hoechst Aktiengesellschaft | Process for making tertiary alkylphosphines |
| US5284555A (en) * | 1991-08-15 | 1994-02-08 | Albright & Wilson Limited | Process for preparing organophosphines |
| CN101638224A (en) * | 2008-07-31 | 2010-02-03 | 中国石油化工股份有限公司 | Method for purifying phosphine by-product and application method of phosphine by-product |
| CN105315305A (en) * | 2014-07-28 | 2016-02-10 | 中国石油化工股份有限公司 | Synthetic method for alkyl phosphine |
-
2019
- 2019-06-27 CN CN201910570079.4A patent/CN112142789A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4757156A (en) * | 1986-08-28 | 1988-07-12 | Hoechst Aktiengesellschaft | Process for making tertiary alkylphosphines |
| US5284555A (en) * | 1991-08-15 | 1994-02-08 | Albright & Wilson Limited | Process for preparing organophosphines |
| CN101638224A (en) * | 2008-07-31 | 2010-02-03 | 中国石油化工股份有限公司 | Method for purifying phosphine by-product and application method of phosphine by-product |
| CN105315305A (en) * | 2014-07-28 | 2016-02-10 | 中国石油化工股份有限公司 | Synthetic method for alkyl phosphine |
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