CN109054082B - Organic ester stabilizer containing phosphorous acid and synthetic method thereof - Google Patents

Organic ester stabilizer containing phosphorous acid and synthetic method thereof Download PDF

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CN109054082B
CN109054082B CN201810810157.9A CN201810810157A CN109054082B CN 109054082 B CN109054082 B CN 109054082B CN 201810810157 A CN201810810157 A CN 201810810157A CN 109054082 B CN109054082 B CN 109054082B
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acid
pentaerythritol
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phosphite
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CN109054082A (en
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李熊伟
李建成
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Zhejiang Jinrun Biotechnology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract

The present invention aims at overcoming the demerits of available technology, and provides one kind of stabilizer with high heat stability, high oxygen resistance, high weather resistance and high hydrolysis resistance for plastic processing, such as polyvinyl chloride. The organic ester phosphite antioxidant is directly prepared into metal salts which are used as the stabilizer, and the organic ester phosphite antioxidant is an organic ester stabilizer of phosphite esters which is phenol-free, benzene-free, environment-friendly and nontoxic. The characteristics are as follows: high molecular weight dendritic products having pentaerythritol structure; a stabilizer having a reaction type characteristic of multiple functions of oxidation resistance, good lubricating property and good plasticizing property; so as to meet the requirements of people on no toxicity and environmental protection of products.

Description

Organic ester stabilizer containing phosphorous acid and synthetic method thereof
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a calcium (zinc) di- (distearic pentaerythritol phosphite lactic acid) product containing a phosphite organic ester stabilizer and a synthesis method thereof.
Background
Phosphite antioxidants are products which develop faster in antioxidant varieties, the annual growth rate of global antioxidants is 5%, the annual growth rate of phosphite antioxidants reaches more than 7%, and the development speed of phosphite antioxidants has a leading position in the whole antioxidant. Due to the rapid increase of the plastic capacity and output, the increase of the production and consumption of the antioxidant is stimulated and pulled, and the increase of the antioxidant in China keeps at a 10% increase rate. Phosphite antioxidants in China are receiving more and more attention.
The stabilizers added in plastic processing are mainly of two types, namely organic tin type stabilizers which have good stability and are mostly used for processing transparent plastic products, but the defects are mainly shown in three aspects, namely, most organic tin stabilizers are toxic, secondly, the stabilizers have no other functions except stability, and thirdly, other components (such as lubricating agents, auxiliary antioxidants, plasticizers and the like) are added into most organic tin stabilizers, so that the price is high. And secondly, fatty acid salt product stabilizers (such as fatty acid calcium/magnesium/zinc and the like) which are nontoxic and environment-friendly and have the function of a lubricant, but have the defects that the stability is inferior to that of an organic tin stabilizer, most of the fatty acid salts cannot be used for transparent products, and other additives are required to be added to play a synergistic effect (such as an antioxidant, an auxiliary stabilizer and the like) when the stabilizer is used.
Disclosure of Invention
The present invention aims at overcoming the demerits of available technology, and provides one kind of stabilizer with high heat stability, high oxygen resistance, high weather resistance and high hydrolysis resistance for plastic processing, such as polyvinyl chloride. The stabilizer is an organic ester stabilizer containing phosphorous acid and is characterized by being named as: di- (pentaerythrityl distearate phosphite lactic acid) -calcium (zinc) having the molecular formula:
pentaerythritol distearate = phosphorous acid-lactic acid
Calcium (Zinc)
Pentaerythritol distearate = phosphorous acid-lactic acid/lactic acid
Figure 499312DEST_PATH_IMAGE001
The molecular weight is: 1610 to 1635;
the phosphorus content is: 3.80-3.85%;
the calcium content is: 1.2-1.25%;
the zinc content is: 1.95-2.05%.
The synthetic method of the antioxidant containing organic phosphite ester is divided into four steps:
the first step is esterification synthesis of pentaerythritol and stearic acid to prepare pentaerythritol distearate, and the chemical reaction equation is as follows:
2 stearic acid + pentaerythritol → pentaerythrityl distearate +2 water
Figure 911576DEST_PATH_IMAGE002
The reaction process of the first step is as follows: in a reaction bottle provided with an electric stirring device, an electric heating device, a reflux condenser and a temperature measuring system, pentaerythritol and stearic acid are mixed according to a molar ratio of 1: 2, adding the mixture into a reaction bottle for esterification reaction according to the proportion, wherein the catalyst is stannous chloride, the using amount of the stannous chloride is 0.3-0.2%, the reaction temperature is 150-;
the second step is the synthesis of pentaerythritol distearate and triethyl phosphite to prepare pentaerythritol tris-distearate diphosphite, the chemical reaction equation of which is as follows:
pentaerythrityl distearate + triethyl phosphite
→ pentaerythritol distearate +2 ethanol
Figure 858804DEST_PATH_IMAGE003
The reaction process of the second step is as follows: in a reaction bottle provided with an electric stirring device, an electric heating device, a reflux condenser and a temperature measuring system, the product pentaerythritol distearate obtained in the first step of the reaction and triethyl phosphite are mixed according to the molar ratio of 1: 1, the catalyst is phosphoric acid, the dosage is 0.4-0.8%, the reaction temperature is 140-;
the third step is the synthesis of the pentaerythritol distearate phosphite ester and sodium lactate to prepare sodium lactate distearate pentaerythritol phosphite, and the chemical reaction equation is as follows:
bis-stearic acid pentaerythritol phosphite and sodium lactate
→ sodium lactate of pentaerythritol distearate and ethanol
Figure 33433DEST_PATH_IMAGE004
The reaction process of the third step is as follows: in a reaction bottle provided with an electric stirring device, an electric heating device, a reflux condenser and a temperature measuring system, the product of the second step of reaction, namely pentaerythritol distearate phosphite and sodium lactate, is prepared according to the molar ratio of 1: 1, the catalyst is phosphoric acid, the dosage is 0.4-0.8%, the reaction temperature is 140-;
the fourth step is that the sodium lactate of the pentaerythritol diphosphite and the calcium hydroxide (zinc) are subjected to double decomposition displacement reaction to prepare the product calcium (zinc) bis- (pentaerythritol diphosphite and lactic acid), and the chemical reaction equation is as follows:
2 bis stearic acid pentaerythritol phosphorous acid sodium lactate + calcium hydroxide (zinc)
→ di- (pentaerythritolphosphite lactic acid bis stearate) calcium (zinc) +2 sodium hydroxide
Figure 775124DEST_PATH_IMAGE005
The reaction process of the fourth step is as follows: in a jar with electric stirring, electric heating and temperature measuring system, the product sodium lactate bis-stearic acid pentaerythritol ester phosphite and calcium hydroxide (zinc) obtained in the third step are mixed according to the mol ratio of 2: 1, carrying out double decomposition displacement reaction in water, wherein the proportion of water to materials is as follows: 1 (%) at the reaction temperature of 60-90 ℃ for 100-120 minutes, centrifugally dewatering after the reaction is finished, removing water, and drying in a constant-temperature oven at the temperature of 120 ℃ to obtain the organic phosphite stabilizer product, namely calcium (zinc) bis- (pentaerythritolphosphite-lactic acid) bis- (distearate).
Preferably, the catalyst further comprises: sodium hydroxide, phosphoric acid, phosphorous acid, sodium bisulfate, tetrabutyl phthalate, isopropyl phthalate, stannous chloride and stannous oxide.
Preferably, said stearic acid also comprises products synthesized from different fatty acids having the same structural properties as the stearic acid, these fatty acids being: n-octanoic acid, iso-octanoic acid, caprylic-capric acid, n-decanoic acid, dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecanoic acid (stearic acid), isostearic acid, erucic acid, and the like.
Preferably, the method for synthesizing the organic phosphite stabilizer is characterized in that the raw material ratio is calculated according to a molar ratio, and the 1 mol amount is the molecular weight of the compound.
The organic phosphite ester stabilizer can be used as a stabilizer for rubber and plastic product processing. The multifunctional plastic additive has the structural composition, shows antioxidant performance and lubricating performance, and is an additive for processing multifunctional plastics.
The organic ester phosphite antioxidant is directly prepared into metal salts which are used as the stabilizer, and the organic ester phosphite antioxidant is an organic ester stabilizer of phosphite esters which is phenol-free, benzene-free, environment-friendly and nontoxic. The characteristics are as follows: high molecular weight dendritic products having pentaerythritol structure; a stabilizer having a reaction type characteristic of multiple functions of oxidation resistance, good lubricating property and good plasticizing property; so as to meet the requirements of people on no toxicity and environmental protection of products.
Compared with the prior art, the invention has the following advantages and effects: the present invention relates to a new compound which is synthesized by multi-step reaction, and structurally, phosphite ester is connected to make it have antioxidant property, and then metal is connected to make organic salt so as to make it have stable function. The complex formulation process in the prior stabilizer preparation is directly connected into a compound, and the structure of the compound has multiple functions. In plastic processing, it has good effects of preventing oxidation, improving color and luster, and the like, and has the advantages of thermal stability, weather resistance and hydrolysis resistance stability.
Detailed Description
The invention is further described below by way of examples.
Example one.
In a reaction bottle provided with an electric stirring system, an electric heating system, a reflux condenser and a temperature measuring system, 68 g of pentaerythritol (molecular weight 136, the same below), 284(284) g of stearic acid and 0.7 g of stannous chloride catalyst are respectively added into the reaction bottle, esterification reaction is carried out under the protection of vacuum, the reaction temperature is controlled to be 150-, the product sodium bis (stearic acid) pentaerythritol phosphite (808) is obtained. And (2) mixing the product of sodium bis (pentaerythritol) distearate phosphite and calcium hydroxide (zinc) according to a molar ratio of 2: 1, carrying out fourth-step double decomposition and replacement reaction in water, wherein the proportion of water to materials is 8: 1 (%) at the reaction temperature of 60-80 ℃ for 100-120 minutes, centrifugally dewatering after the reaction is finished, removing water, and drying in a constant-temperature oven at the temperature of 120 ℃ to obtain the organic phosphite stabilizer product, namely calcium (zinc) bis- (pentaerythritolphosphite-lactic acid) bis- (distearate).
Example two.
In a reaction bottle provided with an electric stirring system, an electric heating system, a reflux condenser and a temperature measuring system, 68 g of pentaerythritol (molecular weight 136, the same below), 144 (144) g of isooctanoic acid and 0.5 g of stannous oxide serving as a catalyst are respectively added into the reaction bottle, esterification reaction is carried out under the protection of vacuum, the reaction temperature is controlled to be 150-, the product of sodium lactate diisooctanoate pentaerythritol phosphite is obtained. And (2) mixing the product sodium lactate bis (isooctanoate) and calcium hydroxide (zinc) according to a molar ratio of 2: 1, carrying out fourth-step double decomposition and replacement reaction in water, wherein the proportion of water to materials is 8: 1 (%) at a reaction temperature of 60-80 ℃ for 100-120 minutes, centrifugally dewatering after the reaction is finished, removing water, and drying in a constant-temperature oven at 110 ℃ to obtain the organic phosphite stabilizer product, namely calcium (zinc) bis- (diisooctanoic acid pentaerythritol phosphite lactic acid).
Example three.
In a reaction bottle provided with an electric stirring system, an electric heating system, a reflux condenser and a temperature measuring system, 68 g of pentaerythritol (molecular weight 136, the same below), 256 (256) g of palmitic acid and 1.7 g of tetrabutyl phthalate serving as a catalyst are respectively added into the reaction bottle, esterification reaction is carried out under the protection of vacuum, the reaction temperature is controlled to be 160-, the product sodium dipalmitoyl pentaerythritol phosphite is obtained. And (2) mixing the product of sodium bis (pentaerythritol) distearate phosphite and calcium hydroxide (zinc) according to a molar ratio of 2: 1, carrying out fourth-step double decomposition and replacement reaction in water, wherein the proportion of water to materials is 8: 1 (%) at the reaction temperature of 60-90 ℃ for 100-120 minutes, centrifugally dewatering after the reaction is finished, removing water, and drying in a constant-temperature oven at the temperature of 120 ℃ to obtain the organic phosphite stabilizer product, namely calcium (zinc) bis- (pentaerythritol dipalmitoylphosphite lactate).

Claims (5)

1. An organic phosphite stabilizer characterized by the name: di- (pentaerythrityl distearate phosphite lactic acid) -calcium (zinc) having the molecular formula:
pentaerythritol distearate = phosphorous acid-lactic acid
Calcium (Zinc)
Pentaerythritol distearate = phosphorous acid-lactic acid/lactic acid
Figure DEST_PATH_IMAGE001
The molecular weight is: 1610 to 1635;
the phosphorus content is: 3.80-3.85%;
the calcium content is: 1.2-1.25%;
the zinc content is: 1.95-2.05%.
2. The organic phosphite containing stabilizer according to claim 1: the synthesis method of di- (pentaerythrityl distearate phosphite lactic acid) -calcium (zinc) is characterized by comprising four steps of synthesis:
the first step is esterification synthesis of pentaerythritol and stearic acid to prepare pentaerythritol distearate, and the chemical reaction equation is as follows:
2 stearic acid + pentaerythritol → pentaerythrityl distearate +2 water
Figure DEST_PATH_IMAGE002
The reaction process of the first step is as follows: in a reaction bottle provided with an electric stirring device, an electric heating device, a reflux condenser and a temperature measuring system, pentaerythritol and stearic acid are mixed according to a molar ratio of 1: 2, adding the mixture into a reaction bottle for esterification reaction, wherein the catalyst is stannous chloride, the using amount is 0.3-0.2% by mass ratio, the reaction temperature is 150-;
the second step is the synthesis of pentaerythritol distearate and triethyl phosphite to prepare pentaerythritol tris-distearate diphosphite, the chemical reaction equation of which is as follows:
pentaerythrityl distearate + triethyl phosphite
→ pentaerythritol distearate +2 ethanol
Figure DEST_PATH_IMAGE003
The reaction process of the second step is as follows: in a reaction bottle provided with an electric stirring device, an electric heating device, a reflux condenser and a temperature measuring system, the product pentaerythritol distearate obtained in the first step of the reaction and triethyl phosphite are mixed according to the molar ratio of 1: 1, the catalyst is phosphoric acid, the mass ratio of the catalyst is 0.4-0.8%, the reaction temperature is 140-;
the third step is the synthesis of the pentaerythritol distearate phosphite ester and sodium lactate to prepare sodium lactate distearate pentaerythritol phosphite, and the chemical reaction equation is as follows:
bis-stearic acid pentaerythritol phosphite and sodium lactate
→ sodium lactate of pentaerythritol distearate and ethanol
Figure DEST_PATH_IMAGE004
The reaction process of the third step is as follows: in a reaction bottle provided with an electric stirring device, an electric heating device, a reflux condenser and a temperature measuring system, the product of the second step of reaction, namely pentaerythritol distearate phosphite and sodium lactate, is prepared according to the molar ratio of 1: 1, the catalyst is phosphoric acid, the mass ratio of the catalyst is 0.4-0.8%, the reaction temperature is 140-;
the fourth step is that the sodium lactate of the pentaerythritol diphosphite and the calcium hydroxide (zinc) are subjected to double decomposition displacement reaction to prepare the product calcium (zinc) bis- (pentaerythritol diphosphite and lactic acid), and the chemical reaction equation is as follows:
2 bis stearic acid pentaerythritol phosphorous acid sodium lactate + calcium hydroxide (zinc)
→ di- (pentaerythritolphosphite lactic acid bis stearate) calcium (zinc) +2 sodium hydroxide
Figure DEST_PATH_IMAGE005
The reaction process of the fourth step is as follows: in a jar with electric stirring, electric heating and temperature measuring system, the product sodium lactate bis-stearic acid pentaerythritol ester phosphite and calcium hydroxide (zinc) obtained in the third step are mixed according to the mol ratio of 2: 1, carrying out double decomposition displacement reaction in water, wherein the mass ratio of water to materials is 8: 1, the reaction temperature is 60-80 ℃, the reaction time is 100-120 minutes, centrifugal dehydration is carried out after the reaction is finished, water is removed, and the product, namely calcium (zinc) bis- (pentaerythrityl distearate phosphite lactic acid) as a phosphite organic ester stabilizer is obtained after the centrifugal dehydration is carried out and the drying is carried out in a constant-temperature oven at 120 ℃.
3. The organic phosphite stabilizer as set forth in claim 1, which is used as a stabilizer for rubber and plastic products.
4. The method of claim 2, wherein said stearic acid further comprises a product synthesized from different fatty acids having the same structural properties as said stearic acid, said fatty acids comprising: n-octanoic acid, iso-octanoic acid, caprylic-capric acid, n-decanoic acid, dodecanoic acid (lauric acid), tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecanoic acid (stearic acid), iso-octadecanoic acid, and erucic acid.
5. The method of claim 2, wherein the ratio of the raw materials is calculated by mole ratio, and the 1 mole amount is the molecular weight of the desired compound.
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CN110483579A (en) * 2019-07-24 2019-11-22 胡宝建 A kind of match gram phosphorous acid alcohol ester and preparation method thereof and application
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WO2004087722A1 (en) * 2003-04-04 2004-10-14 Akzo Nobel N.V. Phosphite reactions in the presence of metal soaps for liquid stabilisers
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CN102250434A (en) * 2011-05-23 2011-11-23 桐乡市中诚化工有限公司 Polyvinyl chloride stabilizer and synthesis process thereof
CN103319811A (en) * 2013-06-27 2013-09-25 浙江传化华洋化工有限公司 Method for synthesizing organic salt heat stabilizer
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EP0038876A1 (en) * 1980-04-28 1981-11-04 ADEKA ARGUS CHEMICAL CO., Ltd. 2,6-Di-tertiary butyl phenyl pentaerythritol spiro bis-phosphites enhancing the stability to heat and light of synthetic resins, stabilizer compositions comprising phenolic antioxidants and such phosphites, and synthetic resin compositions containing the same
WO2004087722A1 (en) * 2003-04-04 2004-10-14 Akzo Nobel N.V. Phosphite reactions in the presence of metal soaps for liquid stabilisers
CN1765908A (en) * 2005-09-07 2006-05-03 华南理工大学 Distearopentaerythritoldiphosphite ester synthesis method
CN102250434A (en) * 2011-05-23 2011-11-23 桐乡市中诚化工有限公司 Polyvinyl chloride stabilizer and synthesis process thereof
CN103319811A (en) * 2013-06-27 2013-09-25 浙江传化华洋化工有限公司 Method for synthesizing organic salt heat stabilizer
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