CN112645981B - Phosphine compound and its production process - Google Patents
Phosphine compound and its production process Download PDFInfo
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- CN112645981B CN112645981B CN202011391198.2A CN202011391198A CN112645981B CN 112645981 B CN112645981 B CN 112645981B CN 202011391198 A CN202011391198 A CN 202011391198A CN 112645981 B CN112645981 B CN 112645981B
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 33
- -1 Phosphine compound Chemical class 0.000 title claims abstract description 28
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 30
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 28
- 229920000049 Carbon (fiber) Polymers 0.000 claims abstract description 22
- 239000004917 carbon fiber Substances 0.000 claims abstract description 22
- 239000008367 deionised water Substances 0.000 claims abstract description 21
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims abstract description 15
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims abstract description 15
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 14
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 14
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 14
- 239000011592 zinc chloride Substances 0.000 claims abstract description 14
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 20
- 239000012065 filter cake Substances 0.000 claims description 20
- 239000000706 filtrate Substances 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- HLBOAQSKBNNHMW-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyridine Chemical compound COC1=CC=CC(C=2C=NC=CC=2)=C1 HLBOAQSKBNNHMW-UHFFFAOYSA-N 0.000 claims description 2
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 229910052725 zinc Inorganic materials 0.000 abstract description 3
- 239000011701 zinc Substances 0.000 abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 abstract description 2
- 229910052759 nickel Inorganic materials 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000001721 carbon Chemical class 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
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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
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- B01J35/58—Fabrics or filaments
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/34—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation
- B01J37/341—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation
- B01J37/343—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation of ultrasonic wave energy
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- C07F9/02—Phosphorus compounds
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Abstract
The invention discloses a phosphine compound and a production process thereof, and a catalyst is prepared in the preparation process, graphene oxide and carbon fiber are subjected to ultrasonic treatment by the catalyst, so that the carbon fiber is inlaid in a groove on the surface of the graphene oxide, 1-hydroxybenzotriazole is further added, carboxyl on the surface of the graphene oxide and amino on the surface of the amino carbon fiber react, zinc chloride, ferric chloride and nickel chloride are further fixed, zinc, ferric chloride and nickel chloride are dissolved in deionized water, and zinc, ferric and nickel metal ions are fixed on the surface of the body after ultrasonic treatment, so that the catalyst is prepared.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a phosphine compound and a production process thereof.
Background
The powder coating is a solid coating without solvent and volatile matters, has the advantages of no harm, environmental protection, high efficiency, low price and the like, and in recent years, along with the continuous increase of environmental protection force at home and abroad and the continuous increase of environmental protection consciousness of users, the demand for the powder coating in various fields is more and more urgent, and the powder coating is widely applied in the fields of automobiles, pipelines, household appliances, furniture, aluminum profiles and the like, and the phosphine is a common catalyst in the powder coating.
In the existing phosphine production process, a large amount of catalyst is needed in the preparation process, so that the production cost is increased, the catalyst cannot be recycled, and the resource waste is serious.
Disclosure of Invention
The invention aims to provide a phosphine compound and a production process thereof.
The invention aims to solve the technical problems:
In the existing phosphine production process, a large amount of catalyst is needed in the preparation process, so that the production cost is increased, the catalyst cannot be recycled, and the resource waste is serious.
The aim of the invention can be achieved by the following technical scheme:
A phosphonate compound made by the steps of:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, reactants and tetrahydrofuran into a reaction kettle, stirring for 20-30min at the rotation speed of 200-300r/min and the temperature of 0-3 ℃, adding a catalyst, heating to the temperature of 70-80 ℃ and carrying out reflux reaction for 3-8h to obtain the phosphine compound.
Further, the molar ratio of the phosphorus trichloride to the sublimated sulfur to the aluminum trichloride to the reactants is 1:1:3:3, the reactants are aromatic hydrocarbon or one of Grignard reagents, the Grignard reagents are obtained by reacting halogenated hydrocarbon with magnesium metal, the halogenated hydrocarbon is one of halogenated cycloalkane and halogenated alkane, and the catalyst is 50-60% of the mass of the phosphorus trichloride.
Further, the catalyst is prepared by the following steps:
Step A1: adding graphene and hydrogen peroxide into a reaction kettle, stirring for 5-10min at the rotating speed of 200-300r/min, heating to 70-80 ℃, refluxing and stirring for 4-6h, filtering to remove filtrate, and drying a filter cake to obtain graphene oxide;
Step A2: dispersing carbon fibers in deionized water, adding ethanol, stirring until the mixture is uniform, adding gamma-aminopropyl triethoxysilane, introducing nitrogen for protection, stirring for 10-15 hours at the rotation speed of 300-500r/min and the temperature of 70-80 ℃, filtering to remove filtrate, and drying a filter cake to obtain the amino carbon fibers;
step A3: dispersing graphene oxide prepared in the step A1 in deionized water, adding the aminated carbon fiber prepared in the step A2, performing ultrasonic treatment for 5-10min under the condition of the frequency of 3-5MHz, adding 1-hydroxybenzotriazole, continuing ultrasonic treatment for 1-1.5h, filtering to remove filtrate, and drying a filter cake to prepare a carrier;
Step A4: adding zinc chloride, ferric chloride, nickel chloride and deionized water into a reaction kettle, stirring until the zinc chloride, the ferric chloride and the nickel chloride are completely dissolved, adding the carrier prepared in the step A3, stirring for 30-40min under the condition of the rotating speed of 300-500r/min, performing ultrasonic treatment for 5-10min under the condition of the frequency of 8-10MHz, filtering to remove filtrate, and drying a filter cake under the condition of nitrogen at the temperature of 120-150 ℃ to prepare the catalyst.
Further, the dosage ratio of the graphene to the hydrogen peroxide in the step A1 is 5g:30-50mL, and the mass fraction of the hydrogen peroxide is 30-35%.
Further, the ethanol dosage in the step A2 is 8-10% of the mass of deionized water, and the dosage of gamma-aminopropyl triethoxysilane is 10-15% of the mass of carbon fiber.
Further, the dosage mass ratio of the graphene oxide to the aminated carbon fiber in the step A3 is 2:1-1.2,1, and the dosage of the hydroxybenzotriazole is 30-50% of the mass of the graphene oxide.
Further, the dosage ratio of zinc chloride, ferric chloride, nickel chloride, deionized water and carrier in the step A4 is 1g to 10mL to 3g.
The production process of the phosphine compound specifically comprises the following steps:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, reactants and tetrahydrofuran into a reaction kettle, stirring for 20-30min at the rotation speed of 200-300r/min and the temperature of 0-3 ℃, adding a catalyst, heating to the temperature of 70-80 ℃ and carrying out reflux reaction for 3-8h to obtain the phosphine compound.
The invention has the beneficial effects that: according to the invention, phosphorus trichloride and sublimed sulfur are adopted as raw materials in the process of preparing the phosphine, compared with the prior art, the production cost is reduced, and a catalyst is prepared in the process of preparing the phosphine, the catalyst firstly takes graphene as the raw material, hydrogen peroxide is used for oxidation to enable the surface of the graphene to contain a large amount of active carboxyl groups, then carbon fiber is treated by gamma-aminopropyl triethoxysilane, gamma-aminopropyl triethoxysilane is firstly hydrolyzed to enable siloxane of the carbon fiber to be hydrolyzed to form silanol, then the silanol reacts with active hydroxyl on the surface of the carbon fiber, so that amino groups are grafted on the surface of the carbon fiber, and further graphene oxide and the carbon fiber are subjected to ultrasonic treatment to enable the carbon fiber to be inlaid in grooves on the surface of the graphene oxide, and then 1-hydroxybenzotriazole is added, so that the carboxyl groups on the surface of the graphene oxide and the amino groups on the surface of the carbon fiber react, and further the graphene oxide are fixed, zinc chloride, iron chloride and nickel chloride are dissolved in deionized water, and zinc, iron and nickel metal ions are fixed on the surface of the catalyst after ultrasonic treatment, the catalyst has the advantages of high reduction performance, the catalyst has the advantages of reducing the catalyst and the catalyst has high catalytic reduction performance, and the recycling cost is reduced, and can be fully recovered, and the cost is reduced.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
A phosphonate compound made by the steps of:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, benzene and tetrahydrofuran into a reaction kettle, stirring for 20min at the rotation speed of 200r/min and the temperature of 0 ℃, adding a catalyst, heating to the temperature of 70 ℃, and carrying out reflux reaction for 3h to obtain triphenylphosphine.
The catalyst is prepared by the following steps:
Step A1: adding graphene and hydrogen peroxide into a reaction kettle, stirring for 5min at the rotating speed of 200r/min, heating to 70 ℃, refluxing and stirring for 4h, filtering to remove filtrate, and drying a filter cake to obtain graphene oxide;
Step A2: dispersing carbon fibers in deionized water, adding ethanol, stirring until the mixture is uniform, adding gamma-aminopropyl triethoxysilane, introducing nitrogen for protection, stirring for 10 hours at the rotation speed of 300r/min and the temperature of 70 ℃, filtering to remove filtrate, and drying a filter cake to obtain the aminated carbon fibers;
step A3: dispersing graphene oxide prepared in the step A1 in deionized water, adding the aminated carbon fiber prepared in the step A2, performing ultrasonic treatment for 5min under the condition of the frequency of 3MHz, adding 1-hydroxybenzotriazole, continuing ultrasonic treatment for 1h, filtering to remove filtrate, and drying a filter cake to prepare a carrier;
Step A4: adding zinc chloride, ferric chloride, nickel chloride and deionized water into a reaction kettle, stirring until the zinc chloride, the ferric chloride and the nickel chloride are completely dissolved, adding the carrier prepared in the step A3, stirring for 30min under the condition of the rotating speed of 300r/min, performing ultrasonic treatment for 5min under the condition of the frequency of 8MHz, filtering to remove filtrate, and drying a filter cake under the condition of nitrogen at the temperature of 120 ℃ to prepare the catalyst.
Example 2
A phosphonate compound made by the steps of:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, n-butylmagnesium bromide and tetrahydrofuran into a reaction kettle, stirring for 20min at the rotation speed of 200r/min and the temperature of 3 ℃, adding a catalyst, and carrying out reflux reaction for 3h at the temperature of 80 ℃ to obtain tributylphosphine.
The catalyst is prepared by the following steps:
Step A1: adding graphene and hydrogen peroxide into a reaction kettle, stirring for 10min at the rotating speed of 200r/min, heating to 70 ℃, refluxing and stirring for 6h, filtering to remove filtrate, and drying a filter cake to obtain graphene oxide;
Step A2: dispersing carbon fibers in deionized water, adding ethanol, stirring until the mixture is uniform, adding gamma-aminopropyl triethoxysilane, introducing nitrogen for protection, stirring for 10 hours at the rotation speed of 300r/min and the temperature of 80 ℃, filtering to remove filtrate, and drying a filter cake to obtain the aminated carbon fibers;
Step A3: dispersing graphene oxide prepared in the step A1 in deionized water, adding the aminated carbon fiber prepared in the step A2, performing ultrasonic treatment for 10min under the condition of the frequency of 3MHz, adding 1-hydroxybenzotriazole, continuing ultrasonic treatment for 1h, filtering to remove filtrate, and drying a filter cake to prepare a carrier;
Step A4: adding zinc chloride, ferric chloride, nickel chloride and deionized water into a reaction kettle, stirring until the zinc chloride, the ferric chloride and the nickel chloride are completely dissolved, adding the carrier prepared in the step A3, stirring for 30min under the condition of the rotating speed of 500r/min, performing ultrasonic treatment for 5min under the condition of the frequency of 10MHz, filtering to remove filtrate, and drying a filter cake under the condition of nitrogen at the temperature of 150 ℃ to prepare the catalyst.
Example 3
A phosphonate compound made by the steps of:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, cyclopentyl magnesium bromide and tetrahydrofuran into a reaction kettle, stirring for 30min at the rotation speed of 300r/min and the temperature of 0 ℃, adding a catalyst, heating to the temperature of 70 ℃, and carrying out reflux reaction for 8h to obtain tricyclopentyl phosphine.
The catalyst is prepared by the following steps:
Step A1: adding graphene and hydrogen peroxide into a reaction kettle, stirring for 5min at the rotating speed of 300r/min, heating to 80 ℃, refluxing and stirring for 4h, filtering to remove filtrate, and drying a filter cake to obtain graphene oxide;
Step A2: dispersing carbon fibers in deionized water, adding ethanol, stirring until the mixture is uniform, adding gamma-aminopropyl triethoxysilane, introducing nitrogen for protection, stirring for 15 hours at the temperature of 70 ℃ at the rotation speed of 500r/min, filtering to remove filtrate, and drying a filter cake to obtain the aminated carbon fibers;
Step A3: dispersing graphene oxide prepared in the step A1 in deionized water, adding the aminated carbon fiber prepared in the step A2, performing ultrasonic treatment for 10min under the condition of the frequency of 3MHz, adding 1-hydroxybenzotriazole, continuing ultrasonic treatment for 1h, filtering to remove filtrate, and drying a filter cake to prepare a carrier;
Step A4: adding zinc chloride, ferric chloride, nickel chloride and deionized water into a reaction kettle, stirring until the zinc chloride, the ferric chloride and the nickel chloride are completely dissolved, adding the carrier prepared in the step A3, stirring for 30min under the condition of the rotating speed of 500r/min, performing ultrasonic treatment for 5min under the condition of the frequency of 10MHz, filtering to remove filtrate, and drying a filter cake under the condition of nitrogen at the temperature of 120 ℃ to prepare the catalyst.
Comparative example 1
This comparative example uses iron powder instead of catalyst as compared to example 1, and comprises the following steps:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, benzene and tetrahydrofuran into a reaction kettle, stirring for 20min at the rotation speed of 200r/min and the temperature of 0 ℃, adding iron powder, heating to the temperature of 70 ℃, and carrying out reflux reaction for 10h to obtain the triphenylphosphine.
Comparative example 2
This comparative example uses zinc powder instead of catalyst as compared to example 1, and the specific procedure is as follows:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, benzene and tetrahydrofuran into a reaction kettle, stirring for 20min at the rotation speed of 200r/min and the temperature of 0 ℃, adding zinc powder, heating to the temperature of 70 ℃, and carrying out reflux reaction for 10h to obtain the triphenylphosphine.
Comparative example 3
The comparative example is a common phosphonate preparation process on the market.
Comparing the preparation time of the above preparation processes of examples 1 to 4 and comparative examples 1 to 3, and comparing the yields of the phosphine compounds prepared, the results are shown in table 1 below;
TABLE 1
| Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Preparation time | 3.5h | 3.5h | 8.5h | 10.5h | 10.5h | ＞12h |
| Yield rate | 96.53％ | 97.28％ | 96.42％ | 88.26％ | 89.15％ | 89.34％ |
As is clear from Table 1 above, the preparation time of the process for preparing a phosphine compound of examples 1 to 3 is 3.5 to 8.5 hours, the phosphine compound yield is 96.42 to 97.28%, the preparation time of the process for preparing a phosphine compound of comparative example 1 is 10.5 hours, the phosphine compound yield is 88.26%, the preparation time of the process for preparing a phosphine compound of comparative example 2 is 10.5 hours, the phosphine compound yield is 89.15%, the preparation time of the process for preparing a phosphine compound of comparative example 3 is more than 12 hours, and the phosphine compound yield is 89.34%, and the present invention has the advantages of high yield and high efficiency.
The foregoing is merely illustrative and explanatory of the principles of the invention, as various modifications and additions may be made to the specific embodiments described, or similar thereto, by those skilled in the art, without departing from the principles of the invention or beyond the scope of the appended claims.
Claims (6)
1. A production process of phosphine compound is characterized in that: the method specifically comprises the following steps:
Adding phosphorus trichloride, sublimed sulfur, aluminum trichloride, reactants and tetrahydrofuran into a reaction kettle, stirring for 20-30min at the rotation speed of 200-300r/min and the temperature of 0-3 ℃, adding a catalyst, heating to the temperature of 70-80 ℃ and carrying out reflux reaction for 3-8h to obtain a phosphine compound;
wherein the catalyst is prepared by the following steps:
Step A1: adding graphene and hydrogen peroxide into a reaction kettle, stirring for 5-10min at the rotating speed of 200-300r/min, heating to 70-80 ℃, refluxing and stirring for 4-6h, filtering to remove filtrate, and drying a filter cake to obtain graphene oxide;
Step A2: dispersing carbon fibers in deionized water, adding ethanol, stirring until the mixture is uniform, adding gamma-aminopropyl triethoxysilane, introducing nitrogen for protection, stirring for 10-15 hours at the rotation speed of 300-500r/min and the temperature of 70-80 ℃, filtering to remove filtrate, and drying a filter cake to obtain the amino carbon fibers;
step A3: dispersing graphene oxide prepared in the step A1 in deionized water, adding the aminated carbon fiber prepared in the step A2, performing ultrasonic treatment for 5-10min under the condition of the frequency of 3-5MHz, adding 1-hydroxybenzotriazole, continuing ultrasonic treatment for 1-1.5h, filtering to remove filtrate, and drying a filter cake to prepare a carrier;
Step A4: adding zinc chloride, ferric chloride, nickel chloride and deionized water into a reaction kettle, stirring until the zinc chloride, the ferric chloride and the nickel chloride are completely dissolved, adding the carrier prepared in the step A3, stirring for 30-40min under the condition of the rotating speed of 300-500r/min, performing ultrasonic treatment for 5-10min under the condition of the frequency of 8-10MHz, filtering to remove filtrate, and drying a filter cake under the condition of nitrogen at the temperature of 120-150 ℃ to prepare the catalyst;
Wherein the reactant is one of benzene, n-butyl magnesium bromide and cyclopentyl magnesium bromide.
2. The process for producing a phosphine compound according to claim 1, wherein: the molar ratio of the phosphorus trichloride to the sublimed sulfur to the aluminum trichloride to the reactants is 1:1:3:3, the dosage of the catalyst is 50-60% of the mass of the phosphorus trichloride.
3. The process for producing a phosphine compound according to claim 1, wherein: the dosage ratio of the graphene to the hydrogen peroxide in the step A1 is 5g:30-50mL, and the mass fraction of hydrogen peroxide is 30-35%.
4. The process for producing a phosphine compound according to claim 1, wherein: the ethanol dosage in the step A2 is 8-10% of the mass of deionized water, and the dosage of gamma-aminopropyl triethoxysilane is 10-15% of the mass of carbon fiber.
5. The process for producing a phosphine compound according to claim 1, wherein: the dosage mass ratio of the graphene oxide to the aminated carbon fiber in the step A3 is 2: the dosage of the 1-1.2,1-hydroxybenzotriazole is 30-50% of the mass of the graphene oxide.
6. The process for producing a phosphine compound according to claim 1, wherein: the dosage ratio of the zinc chloride, the ferric chloride, the nickel chloride, the deionized water and the carrier in the step A4 is 1g:1g:1g:10mL:3g.
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| CN103073584A (en) * | 2013-01-16 | 2013-05-01 | 湖北兴发化工集团股份有限公司 | Method for preparing triphenylphosphine |
| CN104841465A (en) * | 2015-05-08 | 2015-08-19 | 中国石油大学(华东) | Load type nickel phosphide catalyst and pre-phosphating preparation method thereof |
| CN111825715A (en) * | 2020-07-16 | 2020-10-27 | 江苏富比亚化学品有限公司 | Synthesis method of triphenylphosphine derivative tri- (R-phenyl) phosphine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103073584A (en) * | 2013-01-16 | 2013-05-01 | 湖北兴发化工集团股份有限公司 | Method for preparing triphenylphosphine |
| CN104841465A (en) * | 2015-05-08 | 2015-08-19 | 中国石油大学(华东) | Load type nickel phosphide catalyst and pre-phosphating preparation method thereof |
| CN111825715A (en) * | 2020-07-16 | 2020-10-27 | 江苏富比亚化学品有限公司 | Synthesis method of triphenylphosphine derivative tri- (R-phenyl) phosphine |
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