CN1765908A - Distearopentaerythritoldiphosphite ester synthesis method - Google Patents
Distearopentaerythritoldiphosphite ester synthesis method Download PDFInfo
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- CN1765908A CN1765908A CN 200510037048 CN200510037048A CN1765908A CN 1765908 A CN1765908 A CN 1765908A CN 200510037048 CN200510037048 CN 200510037048 CN 200510037048 A CN200510037048 A CN 200510037048A CN 1765908 A CN1765908 A CN 1765908A
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- pentaerythritol diphosphites
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Abstract
The invention discloses a new synthesis method for bistearin pentaerythritol diphosphite ester, which comprises two steps shown below: 1. synthesis to pentaerythritol diphosphite ester; 2. synethsis to the fianl product. This invention needs no organic solvent and so environmental friendly.
Description
Technical field
The present invention relates to a kind of synthetic method that the present invention relates to a kind of oxidation inhibitor, specifically is the new synthetic method of two hard ester group pentaerythritol diphosphites.
Background technology
The structural formula of two hard ester group pentaerythritol diphosphites as shown in Figure 1, because in this molecule, have radical scavenger tetramethylolmethane group and hydrogen peroxide decomposition agent phosphorous acid ester group, radical scavenger and hydrogen peroxide decomposition agent are compounded in an intramolecularly, therefore, this compound is a kind of minute subclass complex type antioxidant and thermo-stabilizer.It and Hinered phenols or hindered amines stablizer and usefulness all can produce synergy, and commodity Weston618/619 by name or JPP618 are that a kind of novel high-performance phosphorus-containing antioxidant has fabulous prospect.
Two hard ester group pentaerythritol diphosphites mainly are used as the auxiliary antioxidant of various synthetic resins such as polyethylene, polypropylene, polyvinyl chloride, ABS resin, polyester.It is to anti-oxidation, improves color and luster etc. and has outstanding effect; Itself have higher thermostability, weather resisteant and hydrolysis stability, so good processing stability, the goods transparency is good; Do not pollute, with UV light absorber, phenolic antioxidant is also with having good synergistic.Still be a kind of good food antioxidant simultaneously, because toxicity is low, can replace food antioxidant BHT, the FDA by FDA (Food and Drug Adminstration) authenticates.This product has General Electric Company of the U.S. abroad, and company is received in Bo Ge-change, and the north of the city chemical company of Japan produces, and domestic have Jilin chemical company to produce and use.
Relevant two hard ester group pentaerythritol diphosphites synthetic methods, present bibliographical information mainly contains: (1) is that raw material synthesizes two hard ester group pentaerythritol diphosphites with triphenyl phosphite, tetramethylolmethane and stearyl alcohol; (2) be the synthetic two hard ester group pentaerythritol diphosphites of main raw material with phosphorus trichloride, tetramethylolmethane and stearyl alcohol.In preceding a kind of method, have the phenol of trace to remove in the product, product easily turns to be yellow, and limits its application at food, field of medicaments; Do not have phenol in the resulting product of a kind of method in back, technology is comparatively complicated, and aftertreatment technology is loaded down with trivial details, and productive rate is low, and must make solvent by adding aromatic hydrocarbons in reaction, and the recovery of solvent is purified complicated.
Summary of the invention
The objective of the invention is to restrain the shortcoming that multiple prior art exists, the synthetic method of a kind of two hard ester group pentaerythritol diphosphites is provided.In the method for the invention, do not need to add organic solvents such as toluene, do not have phenol to produce in the product, so this technology is a kind of new synthetic process of nontoxic, efficient, environmental protection.
For achieving the above object, the present invention has taked following technical scheme:
Principle of the present invention as shown in Figure 2.
The synthetic method of two hard ester group pentaerythritol diphosphites may further comprise the steps:
1, pentaerythritol diphosphites is synthetic
In the there-necked flask that agitator, condenser, thermometer, receptor are housed, add tetramethylolmethane, triethyl-phosphite, catalyzer, stir, stirring velocity is 300～700 rev/mins, under 100～150 ℃ of temperature, react 1～5h, preferred temperature of reaction is 110～150 ℃, and the reaction times is 2～4h; In temperature is 130 ℃, and pressure prepares purified pentaerythritol diphosphites for underpressure distillation under the condition of-0.02～0.06Mpa goes out ethanol and the unreacted triethyl-phosphite that reaction generates;
Tetramethylolmethane: the mol ratio of triethyl-phosphite is 1: 2～2.40;
By weight, catalyst consumption is 1～4% of a tetramethylolmethane, is preferably 2～4%;
Described catalyzer is: sodium methylate, sodium hydroxide, potassium hydroxide, Anhydrous potassium carbonate or organotin;
2, hard ester group pentaerythritol diphosphites is synthetic
In the product of (1) step reaction, add stearyl alcohol, stir, stirring velocity is 300～700 rev/mins, reacts 1～4h under 140～170 ℃ of temperature; Preferred temperature of reaction is 150～170 ℃, and the reaction times is 2～4h; In temperature is 160 ℃, and pressure goes out ethanol for underpressure distillation under the condition of-0.02～0.06Mpa; Obtain white waxy solid after the cooling and be product;
The mol ratio of stearyl alcohol and intermediate pentaerythritol diphosphites is 2～2.20: 1, and preferred mol ratio is 2～2.10: 1.
Compared with the prior art, the present invention has following beneficial effect:
The present invention is the synthetic two hard ester group pentaerythritol diphosphites of raw material with triethyl-phosphite, tetramethylolmethane, stearyl alcohol, in the present invention, do not need to add organic solvents such as toluene, do not have phenol to produce in the product, so the present invention is a kind of new synthetic method of nontoxic, efficient, environmental protection.
Description of drawings
Fig. 1 is the chemical structural formula of two hard ester group pentaerythritol diphosphites;
Fig. 2 is reaction principle figure of the present invention;
Fig. 3 is the infrared spectrogram of embodiment 3 prepared products.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention's scope required for protection is not limited to the related scope of embodiment.
The synthetic method of two hard ester group pentaerythritol diphosphites may further comprise the steps:
1, pentaerythritol diphosphites is synthetic
In the there-necked flask that agitator, condenser, thermometer, receptor are housed, add tetramethylolmethane, triethyl-phosphite, catalyzer, stir, stirring velocity is 300 rev/mins; Reacting 1h under 100 ℃ of temperature, is 130 ℃ in temperature, and pressure prepares purified pentaerythritol diphosphites for underpressure distillation under the condition of-0.02Mpa goes out ethanol and the unreacted triethyl-phosphite that reaction generates;
Tetramethylolmethane: the mol ratio of triethyl-phosphite is 1: 2;
By weight, catalyst consumption is 1% of a tetramethylolmethane; Described catalyzer is a sodium hydroxide;
2, hard ester group pentaerythritol diphosphites is synthetic
In the product of (1) step reaction, add stearyl alcohol, stir, stirring velocity is 300 rev/mins, reacts 1h under 140 ℃ of temperature; Underpressure distillation goes out ethanol; Obtain white waxy solid after the cooling and be product;
The mol ratio of stearyl alcohol and intermediate pentaerythritol diphosphites is 2: 1.
Embodiment 2
The synthetic method of two hard ester group pentaerythritol diphosphites may further comprise the steps:
1, pentaerythritol diphosphites is synthetic
In the there-necked flask that agitator, condenser, thermometer, receptor are housed, add tetramethylolmethane, triethyl-phosphite, catalyzer, stir, stirring velocity is 500 rev/mins, under 130 ℃ of temperature, react 2.5h, in temperature is 130 ℃, and pressure is that underpressure distillation goes out ethanol and the unreacted triethyl-phosphite that reaction generates under the condition of 0.02Mpa, prepares purified pentaerythritol diphosphites;
Tetramethylolmethane: the mol ratio of triethyl-phosphite is 1: 2.20;
By weight, catalyst consumption is 3% of a tetramethylolmethane; Described catalyzer is a sodium methylate;
2, hard ester group pentaerythritol diphosphites is synthetic
In the product of (1) step reaction, add stearyl alcohol, stir, stirring velocity is 500 rev/mins, reacts 3h under 160 ℃ of temperature; In temperature is 160 ℃, and pressure is that underpressure distillation goes out ethanol under the condition of 0.02Mpa; Obtain white waxy solid after the cooling and be product;
The mol ratio of stearyl alcohol and intermediate pentaerythritol diphosphites is 2.05: 1.
Embodiment 3
The synthetic method of two hard ester group pentaerythritol diphosphites may further comprise the steps:
1, pentaerythritol diphosphites is synthetic
In the there-necked flask that agitator, condenser, thermometer, receptor are housed, add tetramethylolmethane, triethyl-phosphite, catalyzer, stir, stirring velocity is 700 rev/mins, under 150 ℃ of temperature, react 5h, in temperature is 130 ℃, and pressure is that underpressure distillation goes out ethanol and the unreacted triethyl-phosphite that reaction generates under the condition of 0.06Mpa, prepares purified pentaerythritol diphosphites;
Tetramethylolmethane: the mol ratio of triethyl-phosphite is 1: 2.40;
By weight, catalyst consumption is 4% of a tetramethylolmethane; Described catalyzer is an Anhydrous potassium carbonate;
2, hard ester group pentaerythritol diphosphites is synthetic
In the product of (1) step reaction, add stearyl alcohol, stir, stirring velocity is 700 rev/mins; Under 170 ℃ of temperature, react 4h; In temperature is 160 ℃, and pressure is that underpressure distillation goes out ethanol under the condition of 0.06Mpa; Obtain white waxy solid after the cooling and be product;
The mol ratio of stearyl alcohol and intermediate pentaerythritol diphosphites is 2.20: 1.
Product analysis
Carry out product analysis with embodiment 2 prepared products.
1, the purification of product
Containing some impurity in the reaction product, mainly is unreacted product, adopts suitable technology to purify, and obtains purified distearyl pentaerythrityl diphosphite.
2, ultimate analysis
To the distearyl pentaerythrityl diphosphite product, do ultimate analysis, the result is as shown in table 1.
Table 1: product results of elemental analyses
| Observed value | C | H | P |
| Theoretical value product measured value | 67.21 67.43 | 11.20 11.32 | 8.47 8.10 |
3, Infrared spectroscopy
The infrared spectra of product is as shown in Figure 3:
In the infrared signature absorption peak of main group, 722 are-CH
2The absorption vibration peak of key; 1032 is the vibration absorption peak of P-O-C key; 1157,1131 is the quaternary carbon stretching vibration peak; 2918,2850,1379,1468 are-CH
3,-CH
2Flexible and flexural vibration peak; Consistent with the main group infrared signature absorption peak in the purpose product structure.
Conclusion: the product that reaction obtains is two hard ester group pentaerythritol diphosphites.
Claims (7)
1, the new synthetic method of two hard ester group pentaerythritol diphosphites is characterized in that may further comprise the steps:
(1) pentaerythritol diphosphites is synthetic;
In the there-necked flask that agitator, condenser, thermometer, receptor are housed, add tetramethylolmethane, triethyl-phosphite, catalyzer, stir, stirring velocity is 300～700 rev/mins, reacts 1～5h under 100～150 ℃ of temperature; In temperature is 130 ℃, and pressure prepares purified pentaerythritol diphosphites for underpressure distillation under the condition of-0.02～0.06Mpa goes out ethanol and the unreacted triethyl-phosphite that reaction generates;
Tetramethylolmethane: the mol ratio of triethyl-phosphite is 1: 2～2.40;
By weight, catalyst consumption is 1～4% of a tetramethylolmethane;
Described catalyzer is: sodium methylate, sodium hydroxide, potassium hydroxide, Anhydrous potassium carbonate or organotin;
(2) hard ester group pentaerythritol diphosphites is synthetic:
In the product of (1) step reaction, add stearyl alcohol, stir, stirring velocity is 300～700 rev/mins; Under 140～170 ℃ of temperature, react 1～4h; In temperature is 160 ℃, and pressure goes out ethanol for underpressure distillation under the condition of-0.02～0.06Mpa; Obtain white waxy solid after the cooling and be product;
The mol ratio of stearyl alcohol and intermediate pentaerythritol diphosphites is 2～2.20: 1.
2, the new synthetic method of according to claim 1 two hard ester group pentaerythritol diphosphites is characterized in that the catalyst consumption in (1) step is 2～4% of a tetramethylolmethane.
3, the new synthetic method of according to claim 1 two hard ester group pentaerythritol diphosphites, the reaction times that it is characterized in that (1) step is 2～4h.
4, the new synthetic method of according to claim 1 two hard ester group pentaerythritol diphosphites, the temperature of reaction that it is characterized in that (1) step is 110～150 ℃.
5, the new synthetic method of according to claim 1 two hard ester group pentaerythritol diphosphites, the temperature of reaction that it is characterized in that (2) step is 150～170 ℃.
6, the new synthetic method of according to claim 1 two hard ester group pentaerythritol diphosphites, the reaction times that it is characterized in that (2) step is 2～4h.
7, the new synthetic method of according to claim 1 two hard ester group pentaerythritol diphosphites is characterized in that the stearyl alcohol in (2) step and the mol ratio 2～2.10: 1 of intermediate pentaerythritol diphosphites.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107268043A (en) * | 2017-07-04 | 2017-10-20 | 电子科技大学 | A kind of inhibitor and electrolytic copper plating bath that filling perforation is electroplated for copper-connection HDI |
| CN109054082A (en) * | 2018-07-23 | 2018-12-21 | 浙江锦润生物科技有限公司 | One kind containing the organic ester stabilizer of phosphorous acid and its synthetic method |
| CN110041360A (en) * | 2019-05-31 | 2019-07-23 | 江苏极易新材料有限公司 | A kind of synthesis technology of antioxidant 618 |
| CN111620905A (en) * | 2020-06-02 | 2020-09-04 | 营口风光新材料股份有限公司 | Preparation method of high-performance phosphorus-containing antioxidant 618 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7206581B2 (en) * | 2003-11-05 | 2007-04-17 | Interdigital Technology Corporation | Method and apparatus for processing data blocks during soft handover |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107268043A (en) * | 2017-07-04 | 2017-10-20 | 电子科技大学 | A kind of inhibitor and electrolytic copper plating bath that filling perforation is electroplated for copper-connection HDI |
| CN107268043B (en) * | 2017-07-04 | 2019-11-05 | 电子科技大学 | A kind of inhibitor and electrolytic copper plating bath for copper-connection HDI plating filling perforation |
| CN109054082A (en) * | 2018-07-23 | 2018-12-21 | 浙江锦润生物科技有限公司 | One kind containing the organic ester stabilizer of phosphorous acid and its synthetic method |
| CN109054082B (en) * | 2018-07-23 | 2020-04-28 | 浙江锦润生物科技有限公司 | Organic ester stabilizer containing phosphorous acid and synthetic method thereof |
| CN110041360A (en) * | 2019-05-31 | 2019-07-23 | 江苏极易新材料有限公司 | A kind of synthesis technology of antioxidant 618 |
| CN111620905A (en) * | 2020-06-02 | 2020-09-04 | 营口风光新材料股份有限公司 | Preparation method of high-performance phosphorus-containing antioxidant 618 |
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