CN114349785A - Synthetic method of isotridecyl phosphite - Google Patents
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Abstract
The invention relates to a method for synthesizing isotridecyl phosphite. The synthesis method adopts the solid alkaline oxide modified by amine as the catalyst, and the catalyst has good activity and can completely carry out the reaction; and the catalyst is easy to separate, does not have catalyst residue and is easy to activate and reuse. The product of the invention has high purity, good quality and long hydrolysis resistance time. Therefore, the invention provides a method for synthesizing isotridecyl phosphite, which is suitable for industrial application.
Description
Technical Field
The invention relates to the field of antioxidants, and in particular relates to a synthetic method of isotridecyl phosphite.
Background
In the processing and using processes of the polymer material, due to the influence of factors such as light, heat, oxygen, shearing force and the like, oxidative degradation can occur and free radicals and hydroperoxides are generated, so that the color and luster of the polymer material are deepened and the physical properties of the polymer material are reduced. Phosphite antioxidants can decompose hydroperoxides formed by oxidation of polymeric materials, thereby preventing or retarding thermal oxidative degradation of polymeric materials. Phosphite ester antioxidant can play good synergistic effect with hindered phenol antioxidant, can generate quinone class material after hindered phenol antioxidant is consumed, and phosphite ester antioxidant can reduce hindered phenol antioxidant's consumption to a certain extent, reduces the auxiliary agent addition, promotes antioxidant effect.
Phosphite antioxidants are mainly classified into solid phosphite antioxidants and liquid phosphite antioxidants. The liquid phosphite ester antioxidant has the advantages of excellent compatibility, low volatility, convenience for pipeline storage and transportation, accurate metering, no dust generation and the like, and is more uniformly mixed with liquid raw materials or polymers. Thus, liquid phosphite antioxidants are more suitable than solid phosphite antioxidants for liquid, solution, emulsion, suspension, melt and other polymerization and processing systems. Alkyl phosphite antioxidants are an important class of liquid phosphite antioxidants and belong to the third generation products, and typical antioxidants include decyl phosphite, dodecyl phosphite, tridecyl phosphite, and the like. However, phosphite antioxidants, especially alkyl phosphite antioxidants, are susceptible to attack by electrophiles due to their large steric bulk around the phosphorus atom and strong nucleophilic effects, and are susceptible to moisture in the air during storage, which can lead to hydrolysis of the phosphite antioxidants to varying degrees, and the antioxidant effect is affected by the reduction in the concentration of the antioxidant due to hydrolysis of the antioxidant.
CN102875593A discloses an alkyl phosphite antioxidant isotridecyl phosphite (i.e., triisotridecyl phosphite, P [ O (CH))2)10CH(CH3)2]3) And has better environmental protection. The document discloses a method for preparing isotridecyl phosphite as follows: in the presence of an equivalent acid-binding agent, isotridecyl alcohol reacts with phosphorus trichloride to generate isotridecyl phosphite, the generated salt is removed by filtration, and the solvent is recovered and the light components are removed through a light component removal process to obtain isotridecyl phosphite; the acid-binding agent is pyridine, triethylamine, N-dimethylaniline and N, N-diethylaniline. However, the reaction can only be carried out in high yield (96.5%) with pure benzene as solvent and pyridine as acid-binding agent, and the product has high purity (99%). However, the benzene used in this method has high carcinogenicity, and benzene is generally avoided as a solvent in industrial production; pyridine, however, has a high boiling point and is difficult to completely remove from the liquid isotridecylphosphite, and the residual catalyst affects the effectiveness of the antioxidant. Another typical method for synthesizing alkyl phosphite antioxidants is the transesterification process, i.e., trimethyl or triethyl phosphite is transesterified with a higher alkyl alcohol in the presence of an acid or base catalyst, during which the methanol or ethanol formed is removed, as is the case with prior artTechniques include, for example, JP2008024667A, WO2012046114a 1. However, the method has the defects of low yield, more by-products of monoiso-tridecyl phosphite and diisotridecyl phosphite in the product, difficult removal and limited product purity.
Therefore, there is still a need to develop more methods for synthesizing isotridecylphosphite.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a novel method for synthesizing isotridecyl phosphite. The method is simple and easy to implement, high in product yield and purity and outstanding in hydrolysis resistance.
The invention provides a method for synthesizing isotridecyl phosphite, which comprises the following steps:
isotridecanol and phosphorus trichloride are reacted in the presence of an amine-modified solid basic oxide to form isotridecyl phosphite.
The synthesis method of the invention preferably comprises the following steps:
adding isotridecanol and amine modified solid basic oxide into an organic solvent, cooling to 0-10 ℃, slowly dropwise adding phosphorus trichloride, and then heating to 50-70 ℃ and keeping for 0.5-3 h; then the temperature is raised to 100-130 ℃ and kept for 2-10h, thus obtaining the isotridecyl phosphite.
The synthesis method of the invention uses amine modified solid alkaline oxide as catalyst, compared with the traditional method which adopts pyridine and other organic bases, the method has similar or better catalytic efficiency, and the obtained product has better quality and better hydrolysis resistance; in addition, the catalyst of the invention is easy to separate and has no residue, and can be reused after being activated.
In one embodiment, the amine-modified solid basic oxide is a silylating agent (R) with amine groups1R2)N-(L)-Si(OR3)3A solid basic oxide functionalized by reaction, wherein R is1、R2、R3Each independently selected from C1-C6 alkyl groups, preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl; l is selected from C1-C10 alkylene, preferably C1-C6 alkylene, more preferably-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH(CH3)CH2CH2-、-C(CH3)2CH2CH2-、-CH2CH(CH3)CH2-、-CH2C(CH3)2CH2-; the solid basic oxide comprises ZnO/Al2O3。
Preferably, the silylating agent (R) having an amine group1R2)N-(L)-Si(OR3)3In, R1、R2Independently selected from methyl, ethyl, n-propyl, n-butyl; r3Is selected from methyl and ethyl, L is selected from-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-。
Preferably, the silylating agent (R) having an amine group1R2)N-(L)-Si(OR3)3At least one member selected from the group consisting of (N, N-dimethyl-2-aminoethyl) trimethoxysilane, (N, N-diethyl-2-aminoethyl) trimethoxysilane, (N, N-dimethyl-3-aminopropyl) trimethoxysilane, (N, N-diethyl-3-aminopropyl) trimethoxysilane, and (N, N-di-N-butyl-3-aminopropyl) trimethoxysilane. Preferably, the silylating agent (R) having an amine group1R2)N-(L)-Si(OR3)3At least one selected from (N, N-dimethyl-2-aminoethyl) trimethoxysilane and (N, N-diethyl-2-aminoethyl) trimethoxysilane.
Preferably, the molar ratio of Zn to Al in the solid basic oxide is 0.5 to 5: 1, preferably 1 to 4: 1, more preferably 2 to 2.5: 1.
preferably, the amine-modified solid basic oxide has a loading of 5 to 40%, preferably 10 to 35%, more preferably 15 to 30% and 20 to 30%, calculated on the mass of the solid basic oxide.
Preferably, the amine-modified solid basic oxide is used in an amount of 6 to 30g of the amine-modified solid basic oxide per mol of phosphorus trichloride, and preferably 10 to 24g and 14 to 20g of the amine-modified solid basic oxide per mol of phosphorus trichloride.
In one embodiment, the molar ratio of phosphorus trichloride to isotridecanol is 1: 3-3.2, preferably 1: 3-3.1, more preferably 1: 3-3.05. In the present invention, the amount of isotridecyl alcohol is preferably not too low, and preferably not less than the theoretical amount, since otherwise the reaction risks formation of monoisotridecyl phosphite and diisotridecyl phosphite.
In one embodiment, the organic solvent is selected from at least one of toluene, chlorobenzene, xylene (ortho, meta, para). Preferably, the organic solvent is selected from toluene.
In one embodiment, the temperature of the temperature reduction is preferably 0 to 5 ℃.
In one embodiment, the reaction is carried out after dropwise addition of phosphorus trichloride, preferably at a temperature of from 50 to 60 ℃.
In one embodiment, the temperature for continued temperature increase is 105-120 ℃. When the organic solvent is toluene, the reflux temperature of toluene is preferred.
In one embodiment, the catalyst is recovered by filtration while hot after the reaction is completed, then the organic solvent is recovered by distillation under reduced pressure, and then the light component is removed under the conditions of 1-20mmHg at 100-150 ℃ to obtain the isotridecyl phosphite.
In the present invention, the amine-modified solid basic oxide can be prepared by the following method:
a) dissolving zinc nitrate and aluminum nitrate in water to prepare a metal salt solution, dissolving potassium hydroxide or sodium hydroxide and potassium carbonate or sodium carbonate in water to prepare an alkali solution, then simultaneously dropwise adding the metal salt solution and the alkali solution into a reactor, stirring and reacting at the temperature of 50-70 ℃ and the pH value of 9-12, and continuously reacting at the temperature for 1-10 hours after dropwise adding; after the reaction is finished, filtering, washing a filter cake to be neutral by water, drying, and roasting in a muffle furnace to obtain a solid alkaline oxide;
b) adding solid basic oxide into dry organic solvent, and adding(R1R2)N-(L)-Si(OR3)3Heating to 60-100 ℃, stirring for reaction, filtering, washing with the dried organic solvent and the anhydrous low-boiling-point solvent respectively, and drying to obtain the amine modified solid basic oxide.
In one embodiment, the molar ratio of zinc nitrate to aluminum nitrate in step a) is from 0.5 to 5: 1, preferably 1 to 4: 1, more preferably 2 to 3: 1.
in one embodiment, the total concentration of cations in the metal salt solution in step a) is in the range of 0.5 to 2M, preferably 1 to 1.5M.
In one embodiment, the molar amount of potassium hydroxide or sodium hydroxide in step a) is the sum of 2.0 to 2.1 times the molar amount of zinc nitrate and 3.0 to 3.1 times the molar amount of aluminum nitrate, and the molar amount of potassium carbonate or sodium carbonate is 0.5 to 0.55 times the molar amount of aluminum nitrate.
In one embodiment, the reaction temperature in step a) is preferably 60 to 65 ℃ and the pH is preferably 10 to 11.
In one embodiment, the temperature of the calcination in step a) is 500-; the time is 5-24h, preferably 9-15 h.
In one embodiment, the solid basic oxide is reacted with (R) in step b)1R2)N-(L)-Si(OR3)3The mass ratio of (A) to (B) is 100: 6-50, preferably 100: 12-40, more preferably 100: 18-38 and 100: 25-38.
In one embodiment, the organic solvent of step b) is selected from at least one of toluene, chlorobenzene, xylene (ortho, meta, para), DMF, DMSO, NMP. Preferably, the organic solvent is selected from toluene.
In one embodiment, the reaction temperature in step b) is 70-95 ℃ and the reaction time is 5-12 h.
In one embodiment, the anhydrous low boiling point solvent in step b) is selected from at least one of anhydrous methanol, anhydrous ethanol, anhydrous tetrahydrofuran.
In the present invention, the recovered catalyst amine-modified solid basic oxide can be reactivated. The activation steps are as follows: the recovered catalyst is washed and then soaked in ammonia water, washed with water and an anhydrous low boiling point solvent, and then dried.
Has the advantages that:
the invention relates to a method for synthesizing isotridecyl phosphite. The synthesis method adopts the solid alkaline oxide modified by amine as the catalyst, and the catalyst has good activity and can completely carry out the reaction; and the catalyst is a solid catalyst, is easy to separate, and does not have catalyst residue in the solution. Meanwhile, the solid catalyst has the advantage of being reusable, and the recovered catalyst can be reused after being simply activated, so that the catalytic efficiency is reduced less. In addition, the product of the invention has high purity and good quality, and thus has the advantage of long hydrolysis resistance time. Therefore, the invention provides a method for synthesizing isotridecyl phosphite, which is suitable for industrial application.
Detailed Description
Hereinafter, preferred examples of the invention will be described in detail. The examples are given for the purpose of better understanding the inventive content and are not intended to be limiting. Insubstantial modifications and adaptations of the embodiments in accordance with the present disclosure remain within the scope of the invention.
Preparation example 1: preparation of catalyst 1
0.2mol (59.5g) of Zn (NO)3)2·6H2O and 0.1mol (37.5g) of Al (NO)3)3·9H2Adding O into 250ml of water, stirring and dissolving, and adding water to prepare a solution with the cation concentration of about 1 mol/L; dissolving 39.2 g of potassium hydroxide and 6.9 g of potassium carbonate in 270ml of water to prepare a solution; then, the two solutions are simultaneously dripped into the reactor, stirred and reacted at the temperature of 60 ℃ and the pH value of about 10, and stirred and reacted for 3 hours at the temperature after the dripping is finished. Filtering after the reaction is finished, washing a filter cake with water until the filtrate is neutral, and drying at 80 ℃; then placing the mixture into a muffle furnace to be roasted for 10 hours at 550 ℃, and obtaining a mixed solution with a Za/Al molar ratio of 2: 1, a solid basic oxide.
Adding 10g of the solid basic oxide into 120ml of dry toluene, adding 2.5g of (N, N-dimethyl-3-aminopropyl) trimethoxy silane, and heating to 90 ℃ under stirring for 7 hours; the filter cake was then washed with dry toluene and dry methanol, respectively, and dried at 80 ℃ to give the amine-modified solid basic oxide, designated catalyst 1. The modification was 20.1 wt% as determined by thermogravimetry (based on the amount of solid basic oxide, as determined by thermogravimetric analysis). Preparation example 2: preparation of catalyst 2
10g of the solid basic oxide from example 1 are taken and added to 120ml of dry toluene, then 3.8g of (N, N-dimethyl-3-aminopropyl) trimethoxysilane are added, and the mixture is heated to 90 ℃ with stirring and maintained for 8 hours; the filter cake was then washed separately with dry toluene and dry methanol and dried at 80 ℃ to give the amine modified solid basic oxide, designated catalyst 2. The modification was 29.9 wt% as determined by thermogravimetry.
Preparation example 3: preparation of catalyst 3
0.25mol (74.4g) of Zn (NO)3)2·6H2O and 0.1mol (37.5g) of Al (NO)3)3·9H2Adding O into 300ml of water, stirring and dissolving, and adding water to prepare a solution with the cation concentration of about 1 mol/L; dissolving 44.8 g of potassium hydroxide and 6.9 g of potassium carbonate in 300ml of water to prepare a solution; then, the two solutions are simultaneously dripped into the reactor, stirred and reacted at the temperature of 60 ℃ and the pH value of about 10, and stirred and reacted for 3 hours at the temperature after the dripping is finished. Filtering after the reaction is finished, washing a filter cake with water until the filtrate is neutral, and drying at 80 ℃; then placing the mixture into a muffle furnace to be roasted for 10 hours at 550 ℃, and obtaining a mixture with a Zn/Al molar ratio of 2.5: 1, a solid basic oxide.
Adding 10g of the solid basic oxide into 120ml of dry toluene, adding 3.1g of (N, N-dimethyl-3-aminopropyl) trimethoxysilane, and heating to 90 ℃ under stirring and maintaining for 8 hours; the filter cake was then washed separately with dry toluene and dry methanol and dried at 80 ℃ to give the amine modified solid basic oxide, designated catalyst 3. The modification was 24.8 wt% as determined by thermogravimetry.
Example 1:
0.305mol (61.1g) of isotridecanol, 1.8g of catalyst 1 and 150ml of toluene are introduced into a reactor equipped with a stirrer, a condenser and a hydrogen chloride absorber, the temperature is reduced to 5 ℃ and 0.1mol (13.7g) of phosphorus trichloride is slowly added dropwise with stirring over 1.5 h. The temperature was raised to 60 ℃ for 2h and then to reflux for 4 h. After the reaction was complete, the catalyst was recovered by filtration while hot, and the filter cake was washed twice with toluene and combined with the filtrate. The solvent was distilled off under reduced pressure, and then light components were removed at 130 ℃ under 5.0mmHg to obtain isotridecyl phosphite.
Example 2:
0.61mol (122.2g) of isotridecanol, 3g of catalyst 2 and 300ml of toluene are introduced into a reactor equipped with a stirrer, a condenser and a hydrogen chloride absorber, the temperature is reduced to 5 ℃ and 0.2mol (27.4g) of phosphorus trichloride is slowly added dropwise with stirring until the end of the addition of phosphorus trichloride is reached within 1.5 h. The temperature was raised to 55 ℃ and held for 2h, then again to reflux and held for 4.5 h. After the reaction was complete, the catalyst was recovered by filtration while hot, and the filter cake was washed twice with toluene and combined with the filtrate. The solvent was distilled off under reduced pressure, and then light components were removed at 130 ℃ under 5.0mmHg to obtain isotridecyl phosphite.
Example 3:
the same as in example 1, except that the catalyst 1 was replaced with the same amount of the catalyst 3.
Example 4:
the procedure was carried out in the same manner as in example 1 except that the recovered and reactivated catalyst 1 was used in the reaction. The activation step is as follows: the recovered catalyst was washed with toluene and water, respectively, and then soaked in 1.5M ammonia water for 0.5h, washed with water and anhydrous methanol, and then dried.
Comparative example 1:
the procedure was as in example 1 of CN 102875593A.
The products of the above examples and comparative examples were characterized and the results are listed in table 1 below, wherein the hydrolysis resistance test was performed with reference to HG/T3712-2010.
Table 1:
| product(s) | Yield (%) | Purity (%) | Hydrolytic resistance (h) | Acid value (mgKOH/g) |
| Example 1 | 98.5 | 99.4 | 344 | ≤0.1 |
| Example 2 | 97.2 | 99.5 | 351 | ≤0.1 |
| Example 3 | 96.2 | 99.3 | 336 | ≤0.1 |
| Example 4 | 96.0 | 99.1 | 314 | ≤0.1 |
| Comparative example 1 | 96.2 | 98.9 | 152 | ≤0.1 |
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (10)
1. A method of synthesizing isotridecyl phosphite, said method comprising:
isotridecanol and phosphorus trichloride are reacted in the presence of an amine-modified solid basic oxide to form isotridecyl phosphite.
2. The method of synthesis of claim 1, comprising:
adding isotridecanol and amine modified solid basic oxide into an organic solvent, cooling to 0-10 ℃, slowly dropwise adding phosphorus trichloride, and then heating to 50-70 ℃ and keeping for 0.5-3 h; then the temperature is raised to 100-130 ℃ and kept for 2-10h, thus obtaining the isotridecyl phosphite.
3. The synthesis method according to claim 1 or 2, characterized in that the amine-modified solid basic oxide is silanized with a silanization reagent (R) bearing an amine group1R2)N-(L)-Si(OR3)3A solid basic oxide functionalized by reaction, wherein R is1、R2、R3Each independently selected from C1-C6 alkyl; l is selected from C1-C10 alkylene; the solid basic oxide comprises ZnO/Al2O3。
4. The cartridge of claim 3The method is characterized in that the silylation agent (R) with amine groups1R2)N-(L)-Si(OR3)3In, R1、R2Independently selected from methyl, ethyl, n-propyl, n-butyl; r3Is selected from methyl and ethyl, L is selected from-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-; the molar ratio of Zn to Al in the solid alkaline oxide is 0.5-5: 1;
preferably, the silylating agent (R) having an amine group1R2)N-(L)-Si(OR3)3At least one member selected from the group consisting of (N, N-dimethyl-2-aminoethyl) trimethoxysilane, (N, N-diethyl-2-aminoethyl) trimethoxysilane, (N, N-dimethyl-3-aminopropyl) trimethoxysilane, (N, N-diethyl-3-aminopropyl) trimethoxysilane, and (N, N-di-N-butyl-3-aminopropyl) trimethoxysilane.
5. The synthesis process according to claim 1 or 2, wherein 6 to 30g of the amine-modified solid basic oxide is used per mol of phosphorus trichloride, preferably 10 to 24g and 14 to 20g of the amine-modified solid basic oxide are used per mol of phosphorus trichloride.
6. The synthesis process according to claim 1 or 2, characterized in that the molar ratio of phosphorus trichloride to isotridecanol is 1: 3-3.2, preferably 1: 3-3.1, more preferably 1: 3-3.05.
7. The method as claimed in claim 2, wherein the catalyst is recovered by filtration while it is hot after the reaction is completed, the organic solvent is recovered by distillation under reduced pressure, and the light component is removed under the conditions of 1-20mmHg at 100 ℃ and 150 ℃ to obtain isotridecyl phosphite.
8. The synthesis method according to any one of claims 1 to 7, wherein the amine-modified solid basic oxide is prepared by:
a) dissolving zinc nitrate and aluminum nitrate in water to prepare a metal salt solution, dissolving potassium hydroxide or sodium hydroxide and potassium carbonate or sodium carbonate in water to prepare an alkali solution, then simultaneously dropwise adding the metal salt solution and the alkali solution into a reactor, stirring and reacting at the temperature of 50-70 ℃ and the pH value of 9-12, and continuously reacting at the temperature for 1-10 hours after dropwise adding; after the reaction is finished, filtering, washing a filter cake to be neutral by water, drying, and roasting in a muffle furnace to obtain a solid alkaline oxide;
b) adding the solid basic oxide to the dried organic solvent, followed by addition of (R)1R2)N-(L)-Si(OR3)3Heating to 60-100 ℃, stirring for reaction, filtering, washing with the dried organic solvent and the anhydrous low-boiling-point solvent respectively, and drying to obtain the amine modified solid basic oxide.
9. The synthesis process according to claim 8, wherein the molar amount of potassium hydroxide or sodium hydroxide in step a) is the sum of 2.0 to 2.1 times the molar amount of zinc nitrate and 3.0 to 3.1 times the molar amount of aluminum nitrate, and the molar amount of potassium carbonate or sodium carbonate is 0.5 to 0.55 times the molar amount of aluminum nitrate.
10. The synthesis process according to claim 8, wherein the reaction temperature in step a) is 60-65 ℃ and the pH is 10-11.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250199A (en) * | 2008-03-20 | 2008-08-27 | 太仓市茜泾化工有限公司 | Method for preparing diisopropyl phosphite |
| WO2012046114A1 (en) * | 2010-10-07 | 2012-04-12 | United Phosphorus Limited | Preparing higher trialkyl phosphites |
| CN102875593A (en) * | 2012-10-22 | 2013-01-16 | 吉林省九新实业集团化工有限公司 | Triisotridecanol phosphite and preparation technique thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250199A (en) * | 2008-03-20 | 2008-08-27 | 太仓市茜泾化工有限公司 | Method for preparing diisopropyl phosphite |
| WO2012046114A1 (en) * | 2010-10-07 | 2012-04-12 | United Phosphorus Limited | Preparing higher trialkyl phosphites |
| CN102875593A (en) * | 2012-10-22 | 2013-01-16 | 吉林省九新实业集团化工有限公司 | Triisotridecanol phosphite and preparation technique thereof |
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