CN108558943B - Method for dissociating methyl phosphine dichloride and aluminum trichloride complex - Google Patents
Method for dissociating methyl phosphine dichloride and aluminum trichloride complex Download PDFInfo
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- CN108558943B CN108558943B CN201810443908.8A CN201810443908A CN108558943B CN 108558943 B CN108558943 B CN 108558943B CN 201810443908 A CN201810443908 A CN 201810443908A CN 108558943 B CN108558943 B CN 108558943B
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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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F7/00—Compounds of aluminium
- C01F7/48—Halides, with or without other cations besides aluminium
- C01F7/56—Chlorides
Abstract
The invention discloses a method for dissociating a phosphine dichloride and aluminum trichloride complex, belonging to the technical field of chemical separation. The invention provides a method for dissociating methyl phosphine dichloride and aluminum trichloride complex, aiming at the problems of low yield, high energy consumption, large amount of generated waste residues, high production cost and the like in dissociating and dissociating methyl phosphine dichloride and aluminum trichloride complex in the prior art, wherein the reaction yield of the method is up to 90-95%, the energy consumption is low, the generated waste residues are easy to process subsequently, a dissociating agent is easy to recover, and the operation is simple.
Description
Technical Field
The invention relates to a method for dissociating a phosphine methyldichloride complex and an aluminum trichloride complex, in particular to a method for dissociating the phosphine methyldichloride complex and the aluminum trichloride complex by using a dissociating agent, and belongs to the technical field of chemical separation.
Background
The national intellectual property office in 2016, 06, 15 discloses an application number CN201610095303.5, which is an invention patent named as a synthetic method of methyl phosphorus dichloride, and discloses a synthetic method of the methyl phosphorus dichloride, wherein the synthetic method takes chloromethane, aluminum trichloride and phosphorus trichloride as raw materials, takes petroleum ether as a solvent, and generates a ligand CH through a reaction3PCl4·AlCl3After petroleum ether is recovered by distillation, aluminum powder and sodium chloride are added, and the product, namely the methyl phosphorus dichloride, is obtained by reduction under the action of a catalyst. The synthesis method of methyl phosphorus dichloride provided by the invention can replace the prior art, solves the problem of emission of organic waste gas in the preparation process, and is a set of complete synthesis process flow which is more in line with the principle of clean production, and in addition, the synthesis method is called as the prior art and has a better production effect, namely, the yield of the product, namely the methyl phosphorus dichloride, can reach 90-95%.
When the methyl phosphine dichloride is prepared by taking aluminum and chloromethane as raw materials, a methyl phosphine dichloride and aluminum trichloride complex is generated, and the methyl phosphine dichloride needs to be obtained by dissociating the complex, and at present, two methods are adopted for dissociating the complex: firstly, alkali metal halide is mixed, distilled and dissociated; secondly, dimethyl phthalate, diethyl phthalate, benzyl cyanide, phosphorus oxychloride and other substances are mixed, distilled and dissociated, and the method is different from the method. The alkali metal halide mixed distillation dissociation is a method which is widely used at present, the method needs reduced pressure distillation, the required vacuum reaches 12KPa, the final distillation temperature needs to be raised to about 160 ℃, the energy consumption is extremely high, part of methyl phosphine dichloride is decomposed and taken away by vacuum, the yield of the methyl phosphine dichloride is reduced, meanwhile, the generated waste residue needs to have better fluidity when the temperature is higher than 120 ℃, the waste residue is solidified into solid after being cooled to below 80 ℃, the subsequent treatment is inconvenient, and the yield of the methyl phosphine dichloride is about 85 percent; the yield of the methyl phosphine dichloride in the second method is 80-86 percent, the used dissociating agent is either high in price or belongs to a highly toxic substance, or has a high boiling point, the solvent needs to be evaporated out when the dissociating agent is recycled, the recovery is difficult, and meanwhile, the energy consumption is high, the cost is high, and the method is not suitable for industrial production.
Disclosure of Invention
The invention aims to solve the problems of low yield, high energy consumption, large amount of generated waste residues, high production cost and the like of dissociating aluminum trichloride from a methyl phosphine dichloride and aluminum trichloride complex system in the prior art, and provides a method for dissociating a methyl phosphine dichloride and aluminum trichloride complex, wherein the reaction yield of the method is up to 90-95%, the energy consumption is low, the generated waste residues are easy to subsequently treat, a dissociating agent is easy to recover, and the operation is simple.
In order to achieve the above object, the technical solution of the present invention is as follows:
a method of dissociating a phosphine methyldichloride and aluminum trichloride complex comprising the steps of:
A. adding petroleum ether into a methyl phosphine dichloride and aluminum trichloride complex system; heating to 30-50 ℃ under stirring;
the temperature of a system comprising the methyl phosphine dichloride and the aluminum trichloride complex is increased to 30-50 ℃, so that the system is more dispersed, the viscosity of the complex is higher when the temperature of the complex is lower than 30 ℃, the complex and petroleum ether can be more uniformly mixed when the temperature is increased to 30-50 ℃, and then the reaction is more sufficient when a dissociation agent is dripped for dissociation.
B. Adding a dissociation agent capable of dissociating the aluminum trichloride complex into the system obtained in the step A; the dropping temperature of the dissociation agent is 40-55 ℃, and stirring is carried out for 10-15 min at 40-55 ℃ after the dropping is finished;
C. and D, directly carrying out phase separation on the reaction liquid obtained in the step B, wherein the methyl phosphine dichloride is in the upper petroleum ether phase, and the lower layer is a complex of the dissociating agent and the aluminum trichloride. Furthermore, the upper layer and the lower layer of the material are separated through the phase splitting equipment and are collected by different equipment; the phase splitting condition is as follows: 40-50 ℃.
Further, in step B of the present invention, the dissociating agent is dimethyl phthalate, diethyl phthalate, dipropyl phthalate, straight-chain or branched C1~C4Carboxylic acid methyl ester, straight or branched C1~C4Carboxylic acid ethyl ester or straight or branched C1~C4A propyl carboxylate.
Further, in step B of the present invention, the dissociation agent is ethyl acetate, isoamyl acetate, butyl acetate or diethyl phthalate.
Further, the petroleum ether solution of methyl phosphine dichloride in the present invention can be used for recovering the solvent and purifying the methyl phosphine dichloride through rectification.
The boiling range of the used petroleum ether is 30-60 ℃, the solvent is rectified and recovered at the position by using laboratory rectifying equipment to carry out normal pressure rectification, and the petroleum ether with the boiling point of 30-60 ℃ is collected by adjusting the reflux ratio, so that the purpose of recovering the solvent is achieved; after the solvent is recovered, normal pressure rectification is also used, the fraction with the boiling range of 80-82 ℃ is collected by further adjusting the reflux ratio, the fraction is the methyl phosphine dichloride, and after the fraction is collected, the purposes of recovering the solvent and purifying the methyl phosphine dichloride are achieved.
Further, the complex of the dissociating agent and the aluminum trichloride is directly added into deionized water for reaction, an organic phase is separated after the reaction is finished, the dissociating agent is recovered, and a water phase is subjected to waste residue conversion.
The complex of the dissociating agent and the aluminum trichloride can be directly separated in deionized water. The complex of the dissociating agent and the aluminum trichloride reacts with the deionized water with heat release, wherein the reaction is actually the reaction of the aluminum trichloride and the deionized water, and is not as violent as the reaction of pure aluminum trichloride and the deionized water; the dissociating agent does not participate in the reaction, when the reaction is finished, the aluminum trichloride reacts with the deionized water to form a soluble substance which is dissolved in the deionized water, and the solubility of the dissociating agent in the deionized water is low, so that the dissociating agent is recovered.
Further, the petroleum ether can be replaced by one or more of n-hexane, cyclohexane and toluene.
Furthermore, the invention also provides the application of ethyl acetate, n-butyl acetate or isoamyl acetate in dissociating the phosphine methyldichloride and aluminum trichloride complex system.
The invention has the beneficial effects that:
the key point of the invention is that the methyl phosphine dichloride in the methyl phosphine dichloride and aluminum trichloride complex system is replaced by the dissociating agent during the dissociation reaction, and the dissociating agent is adopted to carry out the dissociation reaction under mild conditions at the temperature of 40-55 ℃. The conventional sodium chloride is used for dissociating the complex of the methyl phosphine dichloride and the aluminum trichloride, because the complexing effect of the sodium chloride and the aluminum trichloride is weaker than that of the dissociating agent of the invention, and the sodium chloride is solid, the dissociation condition of the sodium chloride is more rigorous, high temperature is required, and the formed new complex is difficult to process under the same condition, so that the cost is increased.
The dissociation of sodium chloride needs to be gradually increased from 30 ℃ to 160 ℃; the new complex is a complex of sodium chloride and aluminum trichloride: NaAlCl4(ii) a The melting point of the new complex formed in the reaction system reaches about 150 ℃, and the new complex is coagulated into a whole solid when the temperature is lower than 80 ℃; and the new complex emits a large amount of white smoke when meeting with air, and the complex needs to be broken again if being treated, or the complex is treated at the temperature higher than 130 ℃; the treatment difficulty is high and the danger is large.
The ratio of the dissociation agent to the aluminum trichloride complex is 1.1-1.5: 1, which is an optimum ratio, and if the dissociation agent is less than 1.1, the dissociation is incomplete and the yield is greatly reduced, while if the dissociation agent is higher than 1.5, the dissociation agent is excessive, and although the yield is also high, the dissociation agent is partially dissolved in the petroleum ether phase, which is not easy to recover and causes waste.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
Example 1
Adding 1mol of 250.5g of methyl phosphine dichloride and aluminum trichloride complex into a 1000ml four-mouth bottle, and then adding 250.5g of petroleum ether as a solvent, wherein the mass ratio of the petroleum ether to the complex is 1: 1; heating to 40 ℃ under stirring, beginning to dropwise add 114.54g of 1.3mol ethyl acetate, controlling the dropwise adding temperature at 50 ℃, and stirring and reacting for 15min at 50 ℃ after the dropwise adding is finished; transferring the reaction solution into a pear-shaped separating funnel at 50 ℃, and carrying out phase separation while the reaction solution is hot at 40-50 ℃ to obtain 341.5g of petroleum ether phase at the upper layer and 274.04g of light yellow viscous liquid at the lower layer; transferring 274.04g of lower layer liquid into a 500ml four-mouth bottle, adding 125.25g of petroleum ether into the bottle, heating to 40 ℃ under stirring, stirring for 10min, immediately transferring the material into a pear-shaped separating funnel, standing, and layering while hot to obtain 136.55g of upper colorless transparent liquid and 262.74g of lower light yellow viscous liquid, wherein 478.05g of the upper layer petroleum ether phase obtained in the step and the upper layer obtained in the first layering are combined, and the methyl phosphine dichloride, namely the upper layer petroleum ether phase, and 262.74g of the lower layer are combined, namely the complex of ethyl acetate and aluminum trichloride and a small amount of petroleum ether.
478.05g of upper-layer materials obtained by phase separation are added into a rectifying device for normal-pressure rectification, under the condition of a reflux ratio of 1:2, fractions with the top temperature of 30-60 ℃ are collected, 370.55g of fractions are collected together, under the condition of a reflux ratio of 1:1, 107g of fractions with the top temperature of 80-82 ℃ are collected together, the GC purity is 99.3%, and the yield of the methyl phosphine dichloride is 90.81%. 0.5g of the residue was left at the bottom of the reaction vessel.
Dripping 262.74g of the lower-layer material obtained by phase separation into 300g of deionized water, wherein the reaction heat release is obvious, the inner temperature is kept to be less than 70 ℃ during the dripping reaction, the system is a clear liquid after the reaction is finished, and is layered, the temperature of the system is reduced to 20-30 ℃, and the upper-layer colorless transparent liquid 96.5g (containing 91.63g of ethyl acetate) and the lower-layer faint yellow liquid 466.24g are obtained, and the recovered ethyl acetate can be obtained after the upper layer is dried, and the recovery rate is about 80%; the lower layer is used for converting waste residues.
If the reaction dissociating agent adopts n-butyl acetate, the recovery rate of the n-butyl acetate can reach 95 percent; if the reaction dissociating agent adopts isoamyl acetate, the recovery rate of the isoamyl acetate can reach 98 percent.
The principle of the invention is as follows: the dissociation agent has atom with lone pair electron, and the outer layer of aluminum atom of aluminum trichloride compound has electron empty orbit, and the dissociation agent and aluminum trichloride can form complex compound. The dissociation effect is better when the dropping temperature is controlled at 40-55 ℃. The dissociation agent has a certain exothermic phenomenon in the dissociation process, and the temperature of the system is increased, so the dropwise addition is selected for the consideration of process safety. Stirring for 10-15 min after the dropwise addition is finished so as to enable the dissociation reaction to be more complete.
Example 2
Adding 1mol of methyl phosphine dichloride and aluminum trichloride complex into a four-mouth bottle, and adding a certain amount of petroleum ether as a solvent, wherein the mass ratio of the petroleum ether to the complex is 1: 1; heating to 30 ℃ under stirring, beginning to dropwise add n-butyl acetate with the molar ratio of 1.25-1.35: 1 to the complex, controlling the dropwise adding temperature to be 40 ℃, and stirring and reacting for 12min at 40 ℃ after the dropwise adding is finished; the reaction solution is directly subjected to phase separation, wherein the methyl phosphine dichloride is in an upper petroleum ether phase, and a lower layer is a complex of n-butyl acetate and aluminum trichloride.
The petroleum ether solution of methyl phosphine dichloride is subjected to rectification to recover the solvent and purify the methyl phosphine dichloride, so that 108.4g of the methyl phosphine dichloride is obtained, the GC purity is 99.2 percent, and the yield of the methyl phosphine dichloride is 91.91 percent.
Example 3
Adding 1mol of methyl phosphine dichloride and aluminum trichloride complex into a four-mouth bottle, and adding a certain amount of petroleum ether as a solvent, wherein the mass ratio of the petroleum ether to the complex is 1: 1; heating to 40 ℃ under stirring, beginning to dropwise add ethyl acetate with the molar ratio of the ethyl acetate to the complex being 1.25-1.35: 1, controlling the dropwise adding temperature to be 50 ℃, and stirring and reacting for 15min at 50 ℃ after the dropwise adding is finished; and (3) directly carrying out phase separation on the reaction solution, wherein the methyl phosphine dichloride is in an upper petroleum ether phase, and the lower layer is a complex of ethyl acetate and aluminum trichloride.
The petroleum ether solution of methyl phosphine dichloride is subjected to rectification to recover the solvent and purify the methyl phosphine dichloride to obtain 107.8g of the methyl phosphine dichloride, the GC purity is 99.4 percent, and the yield of the methyl phosphine dichloride is 91.51 percent.
Example 4
The application of ethyl acetate in dissociating the complex system of methyl phosphine dichloride and aluminum trichloride.
A method of dissociating a phosphine methyldichloride and aluminum trichloride complex comprising the steps of:
A. adding petroleum ether into a methyl phosphine dichloride and aluminum trichloride complex system; heating to 30-50 ℃ under stirring;
the temperature of a system comprising the methyl phosphine dichloride and the aluminum trichloride complex is increased to 30-50 ℃, so that the system is more dispersed, the viscosity of the complex is higher when the temperature of the complex is lower than 30 ℃, the complex and petroleum ether can be more uniformly mixed when the temperature is increased to 30-50 ℃, and then the reaction is more sufficient when ethyl acetate is dropwise added for dissociation.
B. Adding ethyl acetate capable of dissociating the aluminum trichloride complex into the system obtained in the step A; the dropping temperature of the ethyl acetate is 40-55 ℃, and stirring is carried out for 10-15 min at the temperature of 40-55 ℃ after the dropping is finished;
C. and D, directly carrying out phase separation on the reaction liquid obtained in the step B, wherein the methyl phosphine dichloride is in the upper petroleum ether phase, and the lower layer is the mixture of ethyl acetate and aluminum trichloride.
Example 5
The application of n-butyl acetate in dissociating phosphine dichloride and aluminum trichloride complex system.
A method of dissociating a phosphine methyldichloride and aluminum trichloride complex comprising the steps of:
A. adding petroleum ether into a methyl phosphine dichloride and aluminum trichloride complex system; heating to 30-50 ℃ under stirring;
the temperature of a system comprising the methyl phosphine dichloride and the aluminum trichloride complex is increased to 30-50 ℃, so that the system is more dispersed, the viscosity of the complex is higher when the temperature of the complex is lower than 30 ℃, the complex and petroleum ether can be more uniformly mixed when the temperature is increased to 30-50 ℃, and then the reaction is more sufficient when n-butyl acetate is dropwise added for dissociation.
B. Adding n-butyl acetate capable of dissociating the aluminum trichloride complex into the system obtained in the step A; the dropping temperature of the n-butyl acetate is 40-55 ℃, and the n-butyl acetate is stirred for 10-15 min at the temperature of 40-55 ℃ after the dropping is finished;
C. and D, directly carrying out phase separation on the reaction liquid obtained in the step B, wherein the methyl phosphine dichloride is in the upper layer of petroleum ether phase, and the lower layer of the reaction liquid is a mixture of n-butyl acetate and aluminum trichloride.
Example 6
The application of isoamyl acetate in dissociating the complex system of methyl phosphine dichloride and aluminum trichloride.
A method of dissociating a phosphine methyldichloride and aluminum trichloride complex comprising the steps of:
A. adding petroleum ether into a methyl phosphine dichloride and aluminum trichloride complex system; heating to 30-50 ℃ under stirring;
the temperature of a system comprising the methyl phosphine dichloride and the aluminum trichloride complex is increased to 30-50 ℃, so that the system is more dispersed, the viscosity of the complex is higher when the temperature of the complex is lower than 30 ℃, the complex and petroleum ether can be more uniformly mixed when the temperature is increased to 30-50 ℃, and then the reaction is more sufficient when isoamyl acetate is dropwise added for dissociation.
B. Adding isoamyl acetate capable of dissociating the aluminum trichloride complex into the system obtained in the step A; the dripping temperature of the isoamyl acetate is 40-55 ℃, and stirring is carried out for 10-15 min at the temperature of 40-55 ℃ after dripping is finished;
C. and D, directly carrying out phase separation on the reaction liquid obtained in the step B, wherein the methyl phosphine dichloride is in the upper layer of petroleum ether phase, and the lower layer of the reaction liquid is a mixture of isoamyl acetate and aluminum trichloride.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, and all simple modifications and equivalent variations of the above embodiments according to the technical spirit of the present invention are included in the scope of the present invention.
Claims (8)
1. A method for dissociating a phosphine methyldichloride and aluminum trichloride complex, which is characterized by comprising the following steps: the method comprises the following steps:
A. adding petroleum ether into a methyl phosphine dichloride and aluminum trichloride complex system; stirring at the speed of 300 r/min and heating to 30-50 ℃;
B. adding a dissociation agent capable of dissociating the aluminum trichloride complex into the system obtained in the step A; the dropping temperature of the dissociation agent is 40-55 ℃, and stirring is carried out for 10-15 min at 40-55 ℃ after the dropping is finished;
C. carrying out phase separation on the reaction liquid obtained in the step B at 40-50 ℃, wherein the methyl phosphine dichloride is in the upper petroleum ether phase, and the lower layer is a complex of the dissociating agent and aluminum trichloride;
in the step B, the dissociating agent is ethyl acetate, isoamyl acetate, butyl acetate or diethyl phthalate.
2. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 1 wherein: the mass ratio of the petroleum ether to the aluminum trichloride complex in the step A is 1-2: 1-3.
3. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 1 wherein: in the step C, separating the upper layer and the lower layer of the material by phase separation equipment; the phase splitting condition is as follows: 40-50 ℃.
4. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 1 wherein: the dissociation agent is reagent grade, and the content is more than 99%.
5. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 1 wherein: and C, separating petroleum ether and methyl phosphine dichloride in the upper petroleum ether phase by rectification.
6. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 5 wherein: the rectification operation comprises the following steps: adding the upper layer petroleum ether phase into a rectifying device for rectifying; the rectification equipment is a rectification column which is provided with 15-20 glass springs with theoretical plate number per meter and 1-2 meters of filler length; the rectification pressure is 100.6 KPa-101 KPa.
7. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 6 wherein: adjusting the reflux ratio to be 1-5: 1-10, and collecting fractions with the boiling range of 30-60 ℃, namely petroleum ether; adjusting the reflux ratio to be 1-5: 1-10, and collecting fractions with the boiling range of 80-82 ℃ to obtain the methyl phosphine dichloride.
8. The method of dissociating phosphine methyldichloride and aluminum trichloride complex of claim 1 wherein: and C, adding deionized water into the complex of the dissociating agent and the aluminum trichloride in the lower layer to react, separating out an organic phase after the reaction is finished, recovering the dissociating agent, and converting waste residues in a water phase.
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| CN112979702B (en) * | 2019-12-16 | 2024-02-20 | 常州诺法新材料科技有限公司 | Preparation method of organic phosphine compound |
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