Method for purifying and recycling phosphorus compounds
By adding Lewis acids to a mixture of phosphorus compounds for distillation, the problem of catalytic poisoning by side reactions during distillation purification was solved, achieving efficient purification and reuse of phosphorus compounds.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- MARUZEN PETROCHEMICAL CO LTD
- Filing Date
- 2022-02-08
- Publication Date
- 2026-06-09
AI Technical Summary
During the distillation and purification process, phosphorus compounds undergo side reactions to generate catalytic poisons, which leads to a decrease in the yield of alkenyl phosphorus compounds and an increase in manufacturing costs.
By adding Lewis acids to a mixture containing specific phosphorus compounds, alkenyl compounds, and transition metal complexes and then distilling, the generation of byproducts is suppressed, and high-purity phosphorus compounds are recovered for reuse.
It effectively inhibits the formation of catalytic poisons, improves the purity and yield of phosphorus compounds, and reduces manufacturing costs.
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Abstract
Description
Technical Field
[0001] This invention relates to a method for purifying phosphorus compounds. More specifically, this invention relates to a method for purifying phosphorus compounds by distillation. Furthermore, this invention also relates to a method for reusing the purified phosphorus compounds as raw materials for the synthesis of alkenyl phosphorus compounds. Background Technology
[0002] Organophosphorus compounds are chemical substances widely used in various products, such as flame retardants, plasticizers, pesticides, and ligands for metal complexes. In recent years, organophosphorus compounds have also received special attention in industry as functional materials in the fields of metal surface treatment agents, flame-retardant resins, and electronic materials.
[0003] Among organophosphorus compounds, phosphonic acid derivatives are useful precursors for the aforementioned chemical substances, and therefore various manufacturing methods have been studied. For example, the following operation has been carried out: using a catalyst, phosphonic acid derivatives are produced through an addition reaction (hereinafter referred to as hydrophosphorylation) of the P(O)-H bond of phosphonic acid to an alkyne. For example, Patent Document 1 proposes using a partially hydrolyzed phosphonic acid diester compound as a raw material to produce phosphonic acid derivatives. Furthermore, Non-Patent Document 1 proposes using various zero-valent nickel catalysts to produce phosphonic acid derivatives.
[0004] Existing technical documents
[0005] Patent documents
[0006] Patent Document 1: International Publication No. 2017 / 043552
[0007] Non-patent literature
[0008] Non-patent literature 1: J.AM.CHEM.SOC.2004,126,5080-5081 Summary of the Invention
[0009] The problem that the invention aims to solve
[0010] However, under the reaction conditions described in Patent Document 1, during distillation purification, a mixture containing the phosphorus compound of the raw material and the product after the hydrophosphorylation reaction is subjected to vacuum distillation to obtain the phosphorus compound of the raw material and the alkenyl phosphorus compound. In this case, by reusing the obtained phosphorus compound of the raw material as a raw material for the synthesis of alkenyl phosphorus compounds, the raw material cost can be reduced. However, a new problem has been discovered: byproducts that become catalytic poisons are generated due to side reactions occurring during the distillation purification process of the raw phosphorus compound. When the phosphorus compound containing these byproducts is reused as a raw material for the synthesis of alkenyl phosphorus compounds, the yield of the alkenyl phosphorus compound is greatly reduced, thus requiring purification to remove them. As a result, the additional purification step increases manufacturing costs.
[0011] Methods for solving problems
[0012] In order to solve the above-mentioned problems, the inventors of this application conducted in-depth research and found that by adding Lewis acid to the mixture containing a specific phosphorus compound, a specific alkynyl compound, and a transition metal complex during distillation, the generation of byproducts that become catalytic poisons can be suppressed, thereby completing the present invention.
[0013] That is, according to the present invention, the following invention can be provided.
[0014] [1] A method for purifying phosphorus compounds, comprising the following steps:
[0015] The process of obtaining a mixture of a phosphorus compound represented by the following general formula (1), an alkenyl phosphorus compound represented by the following general formula (2), and a transition metal complex; and
[0016] The process of adding Lewis acid to the aforementioned mixture and then distilling it to obtain a first distillate component containing a phosphorus compound represented by the above general formula (1).
[0017] [Chemical Formula 1]
[0018]
[0019] (In general formula (1), R) 1 and R 2 Each of these independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryloxy group. Additionally, R... 1 and R 2 They can bond together to form a ring structure.
[0020] [Chemical Formula 2]
[0021]
[0022] (In general formula (2), R) 1 and R 2 R in general formula (1) 1 and R 2 (Synonyms)
[0023] [2] The purification method as described in [1], wherein in the aforementioned first distillate, the content of the compound represented by the following general formula (3) is less than 0.1% by mass relative to the total mass of the aforementioned first distillate.
[0024] [Chemical Formula 3]
[0025]
[0026] (In general formula (3), R) 3 and R 4 R in general formula (1) 1 and R 2 Synonyms, R 5 (Indicates substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted allyl)
[0027] [3] The purification method as described in [1] or [2], wherein the aforementioned Lewis acid is a metal compound and / or a boron compound.
[0028] [4] The purification method as described in [3], wherein the aforementioned metal compound is selected from at least one of the group consisting of zinc compounds, iron compounds and aluminum compounds.
[0029] [5] The purification method described in [4], wherein the aforementioned zinc compound is zinc chloride.
[0030] [6] The purification method as described in any one of [1] to [5], wherein, in general formulas (1) and (2), R 1 and R 2 Each is independently a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryl group having 1 to 10 carbon atoms.
[0031] [7] The purification method as described in any one of [1] to [6], wherein, in general formula (3), R 3 R 4 and R 5 Each is independently a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted allyl group having 1 to 10 carbon atoms.
[0032] [8] The purification method as described in any one of [1] to [7], wherein the compound represented by general formula (1) is dimethyl phosphite.
[0033] [9] The purification method as described in any one of [1] to [8], wherein the compound represented by general formula (2) is dimethyl vinylphosphonate.
[0034]
[10] The purification method as described in [2], wherein the compound represented by general formula (3) is trimethyl phosphite.
[0035]
[11] A method for reusing the phosphorus compound represented by the above general formula (1) obtained by any one of the purification methods of [1] to
[10] as a raw material for the synthesis of the alkenyl phosphorus compound represented by the above general formula (2).
[0036] Invention Effects
[0037] According to the present invention, by distillation purification of a mixture comprising a specific phosphorus compound, a specific alkenyl phosphorus compound, and a transition metal complex, the generation of byproducts that become catalytic poisons can be suppressed, and the specific phosphorus compound that becomes a synthetic starting material for a specific alkyne compound can be recovered. Furthermore, according to the present invention, the recovered specific phosphorus compound can be reused as a synthetic starting material for a specific alkenyl phosphorus compound. Detailed Implementation
[0038] Purification methods for phosphorus compounds
[0039] In the purification method of the phosphorus compound of the present invention, firstly, a mixture comprising a specific phosphorus compound, a specific alkenyl phosphorus compound, and a transition metal complex is obtained. The preferred step for obtaining the mixture is the following step: in the presence of a transition metal complex as a catalyst, the specific phosphorus compound and acetylene are synthesized into the specific alkenyl phosphorus compound by a hydrophosphorylation reaction, thereby obtaining the above-mentioned mixture.
[0040] Next, Lewis acid is added to the resulting mixture, followed by distillation to obtain a first distillate mainly containing phosphorus compounds. During distillation, a second distillate mainly containing phosphorus compounds and alkenyl phosphorus compounds, and a third distillate mainly containing alkenyl phosphorus compounds, can be further obtained. Adding Lewis acid to the mixture inhibits the dehydration condensation reaction of phosphorus compounds during distillation, thereby suppressing the formation of byproducts that become catalytic poisons. The phosphorus compounds recovered from the first distillate can be reused as raw materials for the synthesis of alkenyl phosphorus compounds.
[0041] The content of phosphorus compounds in the first distillate component is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, and even more preferably 98% by mass or more, relative to the total amount of the first distillate component. The content of by-products in the first distillate component is preferably 0.1% by mass or less, more preferably 0.01% by mass or less, and even more preferably substantially not included. Furthermore, the mass ratio of phosphorus compounds and alkenyl phosphorus compounds in the second distillate component is not particularly limited. For example, relative to the total amount of phosphorus compounds and alkenyl phosphorus compounds in the feedstock, it is preferable that the phosphorus compounds in the feedstock are less than 80% by mass and the alkenyl phosphorus compounds are 20% by mass or more, more preferably less than 50% by mass and the alkenyl phosphorus compounds are 50% by mass or more, and even more preferably less than 20% by mass and the alkenyl phosphorus compounds are 80% by mass or more. Furthermore, relative to the total amount of the third distillate component, the content of alkenyl phosphorus compounds in the third distillate component is preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 98% by mass or more.
[0042] The second distillate obtained above can be redistilled to obtain a fourth distillate mainly containing phosphorus compounds, a fifth distillate mainly containing phosphorus compounds and alkenyl phosphorus compounds, and a sixth distillate mainly containing alkenyl phosphorus compounds. The phosphorus compounds recovered from the fourth distillate can be reused as raw materials for the synthesis of alkenyl phosphorus compounds. The content of phosphorus compounds in the fourth distillate is preferably 80% by mass or more, more preferably 90% by mass or more, further preferably 95% by mass or more, and even more preferably 98% by mass or more, relative to the total amount of the fourth distillate. The content of by-products in the fourth distillate is preferably 0.1% by mass or less, more preferably 0.01% by mass or less, and even more preferably substantially not included. Furthermore, the mass ratio of phosphorus compounds and alkenyl phosphorus compounds in the fifth distillate is not particularly limited. For example, relative to the total amount of phosphorus compounds and alkenyl phosphorus compounds in the feedstock, it is preferable that the phosphorus compounds in the feedstock are less than 80% by mass and the alkenyl phosphorus compounds are 20% by mass or more; more preferably, the phosphorus compounds in the feedstock are less than 50% by mass and the alkenyl phosphorus compounds are 50% by mass or more; even more preferably, the phosphorus compounds in the feedstock are less than 20% by mass and the alkenyl phosphorus compounds are 80% by mass or more. Additionally, relative to the total amount of the sixth distillate, the content of alkenyl phosphorus compounds in the sixth distillate is preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 98% by mass or more. It should be noted that in this invention, the term "mainly comprising" means that the content of the mainly comprised compound is 80% by mass or more.
[0043] The fifth distillate obtained above can be redistilled separately, or mixed with the second distillate obtained above and then redistilled to recover phosphorus compounds, which can then be reused as raw materials for the synthesis of alkenyl phosphorus compounds.
[0044] Regarding the distillation and redistillation conditions described above, there are no particular limitations as long as the target compound can be distilled. For example, the distillation temperature is preferably 40–150°C, more preferably 60–120°C. Furthermore, the distillation time is preferably 1–60 hours, more preferably 8–24 hours. Commercially available distillation equipment of the prior art can be used. Phosphorus compounds, alkenyl phosphorus compounds, and Lewis acids will be described in detail below.
[0045] (Phosphorus compounds)
[0046] The phosphorus compounds contained in the mixture are represented by the following general formula (1).
[0047] [Chemical Formula 4]
[0048]
[0049] (In general formula (1), R) 1 and R 2 Each of these independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryloxy group. Additionally, R... 1 and R 2 They can bond together to form a ring structure.
[0050] In general formula (1), R 1 and R 2 The alkyl, alkoxy, cycloalkyl, aralkyl, aryl, and aryloxy groups preferably have 1 to 10 carbon atoms. It should be noted that the above carbon atom numbers do not include the carbon atoms of the substituents. For example, as R... 1 and R 2 Examples include alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, pentyl, and hexyl; alkoxy groups such as methoxy, ethoxy, and butoxy; cyclohexyl groups such as cycloalkyl; aralkyl groups such as benzyl and phenethyl; phenyl groups such as tolyl, xylyl, and naphthyl; and aryloxy groups such as phenoxy. Among them, R... 1 and R 2 Each is preferably a substituted or unsubstituted alkoxy group.
[0051] In general formula (1), R is used as 1 and R 2Possible substituents include, for example, alkyl, cycloalkyl, alkoxy, cycloalkoxy, heterocyclic, alkylidene, silyl, acyl, acyloxy, carboxyl, cyano, nitro, hydroxyl, mercapto, and oxo groups. Furthermore, the number of carbon atoms in the substituent is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3.
[0052] (Alkenylphosphide compounds)
[0053] The alkenyl phosphorus compounds contained in the mixture are represented by the following general formula (2).
[0054] [Chemical Formula 5]
[0055]
[0056] (In general formula (2), R) 1 and R 2 R in general formula (1) 1 and R 2 (Synonyms)
[0057] Additionally, regarding R 1 and R 2 The preferred method is as described above.
[0058] (Hydrophosphorylation reaction)
[0059] The alkenyl phosphorus compound represented by the above general formula (2) can be obtained, for example, by hydrophosphorylation of the phosphorus compound represented by the above general formula (1). Specifically, the alkenyl phosphorus compound can be synthesized from the phosphorus compound and acetylene as raw materials by hydrophosphorylation in the presence of a transition metal complex as a catalyst.
[0060] Regarding the molar ratio of the phosphorus compound represented by general formula (1) to the alkynyl compound represented by general formula (3) in the starting material of the hydrophosphorylation reaction, the molar ratio of the alkynyl compound when the molar amount of the starting phosphorus compound is 1 is preferably 0.01 to 1000, more preferably 0.1 to 100, and even more preferably 1 to 15.
[0061] (Transition metal complexes (catalysts))
[0062] Transition metal complexes can be used as catalysts in the hydrophosphorylation reaction. Examples of transition metal complexes include nickel complexes, with zero-valent nickel complexes being preferred.
[0063] The aforementioned nickel complex is preferably a nickel complex formed by nickel and a phosphine. As the phosphine, phosphine having aliphatic or aromatic substituents is preferred. Examples of phosphine with aliphatic substituents include trimethylphosphine, tributylphosphine, and trioctylphosphine. Examples of phosphine with aromatic substituents include, for example, triphenylphosphine, 1,2-bis(diphenylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, 1,4-bis(diphenylphosphine)butane, diphenylmethylphosphine, tris(2-methylphenyl)phosphine, tris(3-methylphenyl)phosphine, tris(4-methylphenyl)phosphine, and tris(4-methoxyphenyl)phosphine. Phosphine with aliphatic substituents can significantly increase the reaction rate between the phosphorus compound and the alkenyl compound. Phosphine with aromatic substituents is inexpensive and easy to handle in air, thus reducing manufacturing costs and increasing manufacturing efficiency.
[0064] (Reaction conditions)
[0065] The amount of transition metal complex (catalyst) used in the hydrophosphorylation reaction is not particularly limited as long as the reaction proceeds sufficiently. The amount is preferably 0.01 to 10 mol relative to 1 mol of the phosphorus compound used as a raw material, more preferably 0.1 to 5.0 mol, and even more preferably 0.5 to 2.0 mol.
[0066] The reaction temperature for the hydrophosphorylation reaction is not particularly limited, but considering reaction efficiency, reaction rate, and byproducts, it is preferably -20 to 60°C, more preferably -15 to 40°C, and even more preferably -10 to 10°C. If the reaction temperature is within the above range, the reaction rate of the hydrophosphorylation reaction can be increased, and the conversion rate of the phosphorus compound in the raw material to the alkenyl phosphorus compound can be improved.
[0067] The reaction time for the hydrophosphorylation reaction is not particularly limited, but considering reaction efficiency, reaction rate, and byproducts, it is preferably 30 to 1000 minutes, more preferably 60 to 900 minutes, and even more preferably 120 to 800 minutes. If the reaction time is within the above range, the hydrophosphorylation reaction can be carried out sufficiently, thereby increasing the conversion rate of the phosphorus compound in the raw material to the alkenyl phosphorus compound.
[0068] The hydrophosphorylation reaction can be carried out under either organic solvent or solvent-free conditions, but solvent-free conditions are preferred. The hydrophosphorylation reaction can be carried out by gentle heating using a solvent-free method. Because it is solvent-free, the solvent removal step after the reaction can be omitted, reducing manufacturing costs. It should be noted that the organic solvent is not particularly limited; examples include aromatic hydrocarbons, other hydrocarbons, alcohols, ethers, ketones, and esters.
[0069] Considering reaction efficiency, reaction rate, and byproducts, the hydrophosphorylation reaction is preferably carried out under an inert gas atmosphere. Nitrogen, argon, etc., are preferred as inert gases.
[0070] The conversion rate from phosphorus compound to alkenyl phosphorus compound in the hydrophosphorylation reaction is preferably 60% or more, more preferably 70% or more, even more preferably 75% or more, and even more preferably 80% or more. It should be noted that the "conversion rate (%)" in this invention can be calculated by determining the reduction ratio of the starting phosphorus compound at the end of the reaction based on the amount of the starting phosphorus compound at the start of the reaction. Here, the conversion rate of the reaction can be identified and measured using GC-FID. If the conversion rate from phosphorus compound to alkenyl phosphorus compound is higher than the above-mentioned values, the starting material can be utilized efficiently, manufacturing costs can be reduced, and manufacturing efficiency can be improved.
[0071] (Lewis acid)
[0072] As Lewis acids included in the mixture, metal compounds and / or boron compounds can be used. Examples of metal compounds include zinc compounds, iron compounds, and aluminum compounds, with zinc chloride, zinc bromide, and ferric chloride (II) being preferred, and zinc chloride being more preferred. Examples of boron compounds include borane, borane-tetrahydrofuran complex, borane-dimethyl sulfide complex, borane-diethyl ether complex, trifluoroborane, trifluoroborane-diethyl ether complex, trifluoroborane-tetrahydrofuran complex, and triphenylborane, with borane-tetrahydro complex, borane-diethyl ether complex, and trifluoroborane being preferred. One of these Lewis acids can be used alone, or two or more can be used in combination. By adding a Lewis acid to the mixture and then distilling, the decomposition of the phosphorus compound represented by the above general formula (1) can be suppressed, thereby suppressing the generation of byproducts.
[0073] (Byproduct)
[0074] During the distillation of the mixture, compounds represented by the following general formula (3) may be produced as byproducts.
[0075] [Chemical Formula 6]
[0076]
[0077] (In general formula (3), R) 3 and R 4 R in general formula (1) 1 and R 2 Synonyms, R 5 (Indicates substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted allyl)
[0078] Additionally, regarding R 3 and R 4 The preferred method, and the R mentioned above 1 and R 2 The preferred method is the same.
[0079] In general formula (3), R 5 The alkoxy and aryloxy groups preferably have 1 to 10 carbon atoms. It should be noted that the above carbon atom number does not include the carbon atoms of the substituents. For example, as R... 3 and R 4 Examples include alkoxy groups such as methoxy, ethoxy, and butoxy, and aryloxy groups such as phenoxy. Among them, R... 1 and R 2 Each is preferably a substituted or unsubstituted alkoxy group.
[0080] In general formula (1), R is used as 5 The substituents that may be present include, for example, alkyl, cycloalkyl, alkoxy, cycloalkoxy, heterocyclic, alkylidene, silyl, acyl, acyloxy, carboxyl, cyano, nitro, hydroxyl, mercapto, and oxo groups. Furthermore, the number of carbon atoms in the substituents is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3.
[0081] Regarding the mechanism of byproduct formation during distillation, the following chemical formula will be used to explain the case where dimethyl phosphite ((MeO)₂P(O)H) is used as the phosphorus compound represented by the above general formula (1). During distillation, methanol is generated by the decomposition of dimethyl phosphite. The generated methanol undergoes a dehydration condensation reaction with the tautomer of dimethyl phosphite ((MeO)₂POH), producing trimethyl phosphite as a byproduct. It is believed that in this invention, by adding a Lewis acid before distillation, the dehydration condensation reaction can be prevented. However, the following mechanism is inferred, and this invention is not limited to the following mechanism.
[0082] [Chemical Formula 7]
[0083]
[0084] (Reuse method)
[0085] According to the reuse method of the present invention, the phosphorus compound represented by the above general formula (1) obtained by the above purification method can be used as a synthetic starting material for the hydrophosphorylation reaction of the alkenyl phosphorus compound represented by the above general formula (2). In the phosphorus compound represented by the above general formula (1) obtained by the above purification method, the content of the above-mentioned byproducts that become catalyst poisons is very low. Therefore, the hydrophosphorylation reaction can be carried out efficiently without hindrance, thereby improving the yield of alkenyl phosphorus compounds.
[0086] Example
[0087] The following examples and comparative examples illustrate the present invention in detail, but the present invention is not limited to these examples.
[0088] [Example 1]
[0089] Add 420g of dimethyl phosphite to a 1L autoclave reactor, cool to 0℃, and degas under reduced pressure.
[0090] Next, 7.25 mL of a Ni(PMe3)4 THF solution (concentration 0.25 mol / L) was added, and the mixture was stirred for 15 minutes. Acetylene was supplied to the reaction system at a supply pressure of 0.02 MPa, and the reaction was carried out under the condition of maintaining the internal temperature and stirring until no acetylene absorption was observed. After 9 hours of reaction, a reaction mixture containing dimethyl vinylphosphonate was obtained with a conversion of 71.3% and a selectivity of 91.2%.
[0091] Next, zinc chloride was added as a Lewis acid at 4.0% by mass relative to the total mass of the reaction mixture. Then, vacuum distillation was performed at 1.0 kPa to obtain a first distillate mainly containing dimethyl phosphite, a second distillate mainly containing dimethyl phosphite and dimethyl vinylphosphonate, and a third distillate mainly containing dimethyl vinylphosphonate. The content of dimethyl phosphite in the first distillate was 98.6% by mass, and the content of trimethyl phosphite was below the detection limit (less than 0.1% by mass). Furthermore, the content of dimethyl phosphite in the second distillate was 30% by mass, and the content of dimethyl vinylphosphonate was 70% by mass, relative to the total amount of dimethyl phosphite and dimethyl vinylphosphonate. It should be noted that the content of dimethyl phosphite was determined using GC-FID.
[0092] Next, 4% zinc chloride is added to the mixture of the second distillate, and redistillation is carried out under reduced pressure of 1.0 kPa to obtain a fourth distillate containing dimethyl phosphite, a fifth distillate mainly containing dimethyl phosphite and dimethyl vinylphosphonate, and a sixth distillate containing dimethyl vinylphosphonate. Through the above distillation and redistillation operations, dimethyl phosphite is recovered from the first and fourth distillates. The recovered dimethyl phosphite can be reused as a raw material for the synthesis of dimethyl vinylphosphonate. Further redistillation of the fifth distillate can recover dimethyl phosphite and dimethyl vinylphosphonate. The dimethyl phosphite recovered from the fifth distillate can also be reused as a raw material for the synthesis of dimethyl vinylphosphonate.
[0093] [Comparative Example 1]
[0094] Zinc chloride was not added as a Lewis acid to the reaction mixture described above. Otherwise, distillation and redistillation were performed in the same manner as in Example 1. The content of dimethyl phosphite was 95.3% by mass and the content of trimethyl phosphite was 3.3% by mass relative to the total amount of the first distillate.
[0095] Table 1 presents a summary of the results of Example 1 and Comparative Example 1 described above.
[0096] [Table 1]
[0097]
Claims
1. A method for purifying phosphorus compounds, comprising the following steps: The process of obtaining a mixture of a phosphorus compound represented by the following general formula (1), an alkenyl phosphorus compound represented by the following general formula (2), and a nickel complex; and The process of adding a Lewis acid to the mixture and then distilling it to obtain a first distillate component containing a phosphorus compound represented by the general formula (1) in, The Lewis acid is a metal compound, and the metal compound is at least one selected from the group consisting of zinc compounds, iron compounds, and aluminum compounds. [Chemical Formula 1] In general formula (1), R 1 and R 2 Each of the following independently represents a substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aryloxy group, wherein the number of carbon atoms mentioned above does not include the number of carbon atoms of the substituents; R 1 and R 2 The substituents that may be present are selected from alkyl, cycloalkyl, alkoxy, cycloalkoxy, and oxo groups; the number of carbon atoms contained in the substituents is 1 to 6; [Chemical Formula 2] In general formula (2), R 1 and R 2 R in general formula (1) 1 and R 2 Synonyms.
2. The purification method as described in claim 1, wherein, In the first distillate, the content of the compound represented by the following general formula (3) is less than 0.1% by mass relative to the total mass of the first distillate. [Chemical Formula 3] In general formula (3), R 3 and R 4 R in general formula (1) 1 and R 2 Synonyms, R 5 Represents a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted allyl group having 1 to 10 carbon atoms, wherein the number of carbon atoms mentioned above does not include the number of carbon atoms of the substituent; R 5 The substituents that may be present are selected from alkyl, cycloalkyl, alkoxy, cycloalkoxy, and oxo groups; the number of carbon atoms contained in the substituents is 1 to 6.
3. The purification method as described in claim 1 or 2, wherein, The zinc compound is zinc chloride.
4. The purification method according to claim 1 or 2, wherein, In general formulas (1) and (2), R 1 and R 2 Each is independently a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryl group having 1 to 10 carbon atoms.
5. The purification method as described in claim 2, wherein, In general formula (3), R 3 R 4 and R 5 Each is independently a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted allyl group having 1 to 10 carbon atoms.
6. The purification method according to claim 1 or 2, wherein, The compound represented by general formula (1) is dimethyl phosphite.
7. The purification method according to claim 1 or 2, wherein, The compound represented by general formula (2) is dimethyl vinylphosphonate.
8. The purification method according to claim 2, wherein, The compound represented by general formula (3) is trimethyl phosphite.
9. A method for reusing the phosphorus compound represented by general formula (1) obtained by the purification method according to any one of claims 1 to 8 as a raw material for the synthesis of the alkenyl phosphorus compound represented by general formula (2), comprising the step of obtaining the phosphorus compound represented by general formula (1) by the purification method according to any one of claims 1 to 8.