CN1331872C - Distearopentaerythritoldiphosphite ester synthesis method - Google Patents
Distearopentaerythritoldiphosphite ester synthesis method Download PDFInfo
- Publication number
- CN1331872C CN1331872C CNB2005100370480A CN200510037048A CN1331872C CN 1331872 C CN1331872 C CN 1331872C CN B2005100370480 A CNB2005100370480 A CN B2005100370480A CN 200510037048 A CN200510037048 A CN 200510037048A CN 1331872 C CN1331872 C CN 1331872C
- Authority
- CN
- China
- Prior art keywords
- temperature
- synthetic method
- pentaerythrityl diphosphite
- distearyl pentaerythrityl
- tetramethylolmethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Images
Abstract
The present invention discloses a new synthetic method of bistearin ester group pentaerythritol diphosphite, which comprises the following two steps: 1, pentaerythritol diphosphite is synthesized; 2, bistearin ester group pentaerythritol diphosphite is synthesized. The present invention uses triethyl phosphite, pentaerythritol and octadecy l alcohol as raw materials to synthesize bistearin ester group pentaerythritol diphosphite. The present invention has no need of the addition of organic solvents of toluene, etc., and products have no phenol; therefore, the present invention is a new nontoxic, high efficiency and environment protecting synthetic method.
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 distearyl pentaerythrityl diphosphite.
Background technology
The structural formula of distearyl pentaerythrityl diphosphite 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.
Distearyl pentaerythrityl diphosphite mainly is 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 distearyl pentaerythrityl diphosphite synthetic method, present bibliographical information mainly contains: (1) is that raw material synthesizes distearyl pentaerythrityl diphosphite with triphenyl phosphite, tetramethylolmethane and stearyl alcohol; (2) be the synthetic distearyl pentaerythrityl diphosphite 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, a kind of synthetic method of distearyl pentaerythrityl diphosphite 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 distearyl pentaerythrityl diphosphite 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, the stearyl 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.
Prior art is compared, and the present invention has following beneficial effect:
The present invention is the synthetic distearyl pentaerythrityl diphosphite 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 distearyl pentaerythrityl diphosphite;
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.
Embodiment 1
The synthetic method of distearyl pentaerythrityl diphosphite 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, the stearyl 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.
The synthetic method of distearyl pentaerythrityl diphosphite 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, the stearyl 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.
The synthetic method of distearyl pentaerythrityl diphosphite 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, the stearyl 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 a distearyl pentaerythrityl diphosphite.
Claims (6)
1, the new synthetic method of distearyl pentaerythrityl diphosphite 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) distearyl pentaerythrityl diphosphite 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 distearyl pentaerythrityl diphosphite according to claim 1 is characterized in that the catalyst consumption in (1) step is 2～4% of a tetramethylolmethane.
3, the new synthetic method of distearyl pentaerythrityl diphosphite according to claim 1, the reaction times that it is characterized in that (1) step is 2～4h.
4, the new synthetic method of distearyl pentaerythrityl diphosphite according to claim 1, the temperature of reaction that it is characterized in that (1) step is 110～150 ℃.
5, the new synthetic method of distearyl pentaerythrityl diphosphite according to claim 1, the temperature of reaction that it is characterized in that (2) step is 150～170 ℃.
6, the new synthetic method of distearyl pentaerythrityl diphosphite according to claim 1, the reaction times that it is characterized in that (2) step is 2～4h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100370480A CN1331872C (en) | 2005-09-07 | 2005-09-07 | Distearopentaerythritoldiphosphite ester synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100370480A CN1331872C (en) | 2005-09-07 | 2005-09-07 | Distearopentaerythritoldiphosphite ester synthesis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1765908A CN1765908A (en) | 2006-05-03 |
| CN1331872C true CN1331872C (en) | 2007-08-15 |
Family
ID=36742045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100370480A Expired - Fee Related CN1331872C (en) | 2005-09-07 | 2005-09-07 | Distearopentaerythritoldiphosphite ester synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1331872C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104767596A (en) * | 2003-11-05 | 2015-07-08 | 美商内数位科技公司 | Wireless communication system and method used therein |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
-
2005
- 2005-09-07 CN CNB2005100370480A patent/CN1331872C/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 二亚磷酸二(十六醇)季戊四醇酯的合成工艺研究 陈赤阳等，北京石油化工学院学报，第12卷第4期 2004 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104767596A (en) * | 2003-11-05 | 2015-07-08 | 美商内数位科技公司 | Wireless communication system and method used therein |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1765908A (en) | 2006-05-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108794400B (en) | Amino acid-containing ionic liquid with amino group on cation, and preparation method and application thereof | |
| CN1331872C (en) | Distearopentaerythritoldiphosphite ester synthesis method | |
| CN109174176B (en) | Basic ionic liquid catalyst and preparation method thereof | |
| CN103664944A (en) | Preparation method of acyclovir | |
| KR20170034077A (en) | Metal catalysts for selective formation of cyclic carbonates, process for preparing cyclic carbonate using the same and use of cyclic carbonate | |
| WO2009044803A1 (en) | Process for producing product of asymmetric-catalyst michael reaction | |
| CN101250200A (en) | Method for synthesizing bis-(2,4-di-tert-butyl phenyl) pentaerythritol diphosphite | |
| Cucinella et al. | The chemistry and the stereochemistry of poly (N-alkyliminoalanes): IX. Hexameric organoaluminum imides by reaction of (HAIN-iso-C3H7) 6 with trialkylaluminums | |
| CN115108912B (en) | Strong alkaline ionic liquid catalytic CO 2 Method for synthesizing dimethyl carbonate | |
| CN105732694A (en) | Method for adsorbing and purifying 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane | |
| CN107021969B (en) | The method that catalysis oxidation prepares biotin precursor ketone acid | |
| CN101781205B (en) | Method for synthesizing substitutional crylic acid phenyl ester | |
| CN113333020A (en) | Supermolecular onium salt catalyst for synthesizing carbonate and preparation method thereof | |
| CN102146016B (en) | New method for simply and conveniently synthesizing chlorocyclohexane | |
| CN101311178A (en) | Synthetic method of compound panipenan | |
| CN1765907A (en) | Dicetylpentaerythritoldiphosphite ester synthesis method | |
| AU2013312767B2 (en) | Preparation of dihydroxyethyl piperazine | |
| Setaka et al. | Trimethylsilyl-substituted dibenzodehydro [12] annulene having high thermal and chemical stability | |
| CN103254233A (en) | Ethyl triazinyl triphenyl hypophosphite compound and preparation method thereof | |
| CN109020798B (en) | Colored flame retardant tetra (bromophenoxy) p-benzoquinone compound and preparation method thereof | |
| CN111875577B (en) | Preparation method of R-propylene carbonate | |
| CN110857284B (en) | Method for synthesizing N-methyl aliphatic amine | |
| CN102617650B (en) | Binuclear ferrous complex bridged by thiolate and nitrogenous base/amino group, and preparation method and application of binuclear ferrous complex | |
| CN113321624A (en) | Synthesis method of 1,4, 7-triazacyclononane | |
| CN102718655A (en) | Preparation process of DL-2-hydroxy-3-butenoic acid ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070815 Termination date: 20140907 |
|
| EXPY | Termination of patent right or utility model |