CN107739346B - Tripolythiotriallyl cyanurate and preparation method thereof - Google Patents
Tripolythiotriallyl cyanurate and preparation method thereof Download PDFInfo
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Abstract
The invention discloses triallyl cyanurate and a preparation method thereof, wherein the structural formula of the triallyl cyanurate is as follows:
the preparation method comprises the following steps: chloropropene is used as a solvent of a reaction system and is also used as a reaction monomer to react with trisodium trithiocyanate to generate triallyl trithiocyanate, after the reaction is finished, excessive chloropropene is recovered through vacuum distillation for recycling, the generated mixture of triallyl trithiocyanate and sodium chloride is separated out through slow cooling, and then the sodium chloride can be separated out through micro-membrane filtration or centrifugation, so that the triallyl trithiocyanate is obtained. According to the invention, thioether bonds with excellent performance are introduced into the s-triazine derivatives, and the triallyl cyanurate obtained through synthesis not only can improve the crosslinking density and the thermal stability of the resin, but also can improve the performances such as toughness, water resistance, adhesion, oxidation resistance, refractive index and the like of the polymer.
Description
Technical Field
The invention belongs to the field of compound synthesis, and particularly relates to triallyl cyanurate and a preparation method thereof.
Background
Triallyl cyanurate (TAC) is a trifunctional olefin monomer containing a triazine ring, and a stable triazine ring structure and an active allyl structure exist in the monomer at the same time, so that the crosslinking density of a product is obviously improved, and the product has good heat resistance and dielectric property. Thus, TAC is commonly used as a co-crosslinking agent and a radiation crosslinking aid for rubbers and plastics. TAC is a good assistant crosslinking agent when peroxide is used as a crosslinking agent in polyurethane, polyvinyl chloride, ethylene propylene rubber and the like; meanwhile, TAC is also used as a photosensitizer in radiation crosslinking of polyolefin and polyvinyl chloride to modify the heat resistance of resins such as polymethacrylic resin, polyethylene, polyester and the like.
While thioether linkages can impart more prominent features to the polymer than thioether linkages: hydrophobic, high refractive index, low moisture absorption, low solvent swelling property and good cohesiveness, and in free radical photopolymerization, the sulfur-containing monomer has certain antioxidant polymerization inhibition effect, and the cured polymer has hydrophobic and high refractive index. Therefore, through molecular design, a sulfur-containing multifunctional olefin monomer, namely Triallyl cyanurate (TTAC), is synthesized, so that the triazine derivative with more excellent performance is obtained.
Disclosure of Invention
The invention aims to provide a novel triazine derivative, namely triallyl cyanurate, which not only can improve the crosslinking density and the thermal stability of resin, but also can improve the performances of toughness, water resistance, adhesion, oxidation resistance, refractive index and the like of a polymer, and also provides a preparation method of triallyl cyanurate.
In order to achieve the purpose, the invention adopts the following technical scheme:
the structural formula of the triallyl trisulfate is shown as the formula (I):
the Triallyl cyanurate (TTAC) synthesized by the method is named as 2,4,6-tri (2-propenylthio) -1,3,5-triazine (2,4,6-tris (2-propenylthio) -1,3,5-triazine), and the molecular structure of the Triallyl cyanurate (TTAC) contains allyl with high reaction activity, high-flexibility thioether bond and high-stability triazine ring structure, so that the polymer has excellent performances such as toughness, high refractive index, low solvent swelling property, good adhesion and the like. Similar to TAC, TTAC is a trifunctional vinyl monomer, can be used as a vulcanizing agent for highly saturated rubber and a curing agent for unsaturated polyester, and can also be used as a photosensitizer in radiation crosslinking of polyolefin and polyvinyl chloride so as to improve the performances of crosslinking density, thermal stability and the like of resin. On the other hand, the thioether bond in the TTAC structure can further improve the performances of the polymer such as toughness, water resistance, adhesiveness, oxidation resistance, refractive index and the like, and further expand the application range of the s-triazine derivative.
The invention also provides a preparation method of the triallyl cyanurate, which comprises the following steps:
(1) synthesis of trisulfated triallyl cyanurate: adding chloropropene into a reactor, stirring, and adding trisodium trithiocyanate in batches, wherein the molar ratio of the trisodium trithiocyanate to the chloropropene is 1: 3.9-6.0, the feeding time of the trisodium trithiocyanate is 40-90 min, stirring and reacting for 10-40 min after the feeding is finished, and the temperature of a reaction system is controlled to be 3-12 ℃ in the whole process;
(2) heating for reaction: after the step (1) is finished, adding 20-100 ppm of polymerization inhibitor into a reaction system, heating the reaction system to 40-45 ℃, and continuously stirring for reaction for 10-40 min;
(3) vacuum distillation: after the step (2) is finished, carrying out vacuum distillation on the reacted mixed liquid at 40-45 ℃, recovering unreacted chloropropene monomers in the system, and recycling the recovered chloropropene as a reactant;
(4) separation and purification: and after the distillation is completed, slowly cooling the mixture of the remaining triallyl trisulfate and sodium chloride in the reactor to 25-30 ℃ to separate out the sodium chloride, stirring for 05-1.5 h, and after the sodium chloride in the system is completely separated out, removing the sodium chloride through micro-membrane filtration or centrifugation to obtain the triallyl trisulfate.
In the method, chloropropene is used as a solvent of a reaction system and is also used as a reaction monomer to react with trisodium trithiocyanate to generate triallyl trithiocyanate, after the reaction is finished, excessive chloropropene is recovered through vacuum distillation to be recycled, and the generated mixture of triallyl trithiocyanate and sodium chloride is obtained, wherein the triallyl trithiocyanate is liquid, the sodium chloride is solid and insoluble in triallyl trithiocyanate, the sodium chloride is separated out through slow cooling, and the sodium chloride can be separated out through microfilm filtration or centrifugation, so that the triallyl trithiocyanate is obtained, the yield of the triallyl trithiocyanate prepared by the method is over 95%, and the purity is 99.3-99.7%. The formula (II) is a reaction formula for synthesizing the triallyl trisulfate, after the reaction in the step (1) is finished, the conversion rate is about 90-95%, after the step (2) is heated for further reaction, the final conversion rate can reach 95-98.3%,
preferably, the molar ratio of the trisodium trithiocyanate to the chloropropene is 1: 4.5-5.1. The chloropropene is used as a solvent and a reaction monomer, and the amount of the chloropropene in a reaction system is controlled, so that the occurrence of side reactions can be reduced.
Preferably, the trisodium trithiocyanate salt is added in step (1) in batches, each batch is separated by 4-15 min, and the reaction time in step (1) is not more than 2h, wherein the reaction time is the time from the beginning of adding the trisodium trithiocyanate to the end of the reaction in step (1). By adding trisodium trithiocyanate in batches, the reaction rate and the exothermic amount of the reaction system can be controlled, thereby avoiding side reactions and reducing unnecessary side reactions by controlling the total reaction time.
Preferably, the trisodium trithiocyanate is added for 3-5 times, and the sum of the feeding time and the time interval of each batch is 80-100 min.
Preferably, the total reaction time of the step (1) and the step (2) is 1.5-3.0 h, and the total reaction time is the feeding time and the interval time in the step (1), the heating time in the step (2) and the stirring reaction time.
Preferably, after the step (1) is finished, adding 20-100 ppm of polymerization inhibitor into the reaction system, wherein the polymerization inhibitor is hydroquinone or hydroquinone derivatives. Because the sulfur element in the triallyl cyanurate structure has a certain antioxidation and polymerization inhibition function, the triallyl cyanurate can be prevented from being oxidized and polymerized by adding a trace amount of polymerization inhibitor before heating, and the triallyl cyanurate is prevented from being yellow or the viscosity of the triallyl cyanurate is prevented from being increased. The polymerization inhibitor can be selected from hydroquinone derivatives, preferably hydroquinone, wherein the concentration of the polymerization inhibitor is calculated on the basis of the theoretical yield of triallyl cyanurate.
Preferably, the microfilm in step (4) is a tetrafluoroethylene or vinylidene fluoride filter membrane with the diameter of 0.1-0.5 μm.
Compared with the prior art, the invention has the following beneficial effects:
(1) in the invention, thioether bonds with excellent performance are introduced into the s-triazine derivatives to synthesize triallyl cyanurate, so that the triallyl cyanurate has more excellent performances such as toughness, water resistance, adhesion, oxidation resistance, refractive index and the like, can be used as a vulcanizing agent of highly saturated rubber and a curing agent of unsaturated polyester, and can also be used as a photosensitizer in radiation crosslinking of polyolefin and polyvinyl chloride, so that the crosslinking density, thermal stability and other performances of the resin are improved, and the application range of the s-triazine derivatives is further expanded.
(2) The chloropropene with a lower boiling point is selected as a reaction monomer and a solvent, and is recovered by vacuum low-temperature distillation, so that on one hand, the defects of product color change, viscosity increase and the like caused by oxidation or polymerization at high temperature are avoided; on the other hand, chloropropene is adopted as a reaction solvent, other solvents are not used, and the cyclic use is favorable for reducing the product cost, reducing the production steps, saving energy and resources, reducing the discharge of three wastes and realizing the green and environment-friendly synthesis process.
(3) According to the method, the trisodium trithiocyanate is added in batches, so that the reaction rate and the temperature of a reaction system are effectively controlled, the occurrence of side reactions is reduced, and the yield and the purity of the product are improved, wherein the yield of the triallyl trithiocyanate prepared by the method is over 95%, and the purity is 99.3-99.7%.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of the triallyl cyanurate product prepared in example 3.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
The purity of the chloropropene used in the embodiment of the invention is 99-100%.
Example 1
The preparation method of triallyl trisulfate of this example comprises the following steps:
(1) 619.8Kg of chloropropene (8100mol, excess 80%) is pumped into a 1000L enamel reactor with a cooling loop and a circulating water bath loop, a stirring and cooling loop is started, and the temperature of chloropropene monomers in the reactor is reduced to 0-2 ℃. Then, 364.8Kg (1500mol) of trisodium trithiocyanate was added slowly in portions (3 total portions, about 121Kg each, with intervals of about 10-12 min). The trisodium trithiocyanate is quickly dissolved and reacts with chloropropene to release heat, the temperature in the reactor is controlled to be 3-10 ℃ through a cooling loop and the control of the feeding speed, the total feeding time is controlled to be 60min, and the reaction is continued for 20min after the feeding is finished.
(2) In order to realize the complete reaction of the raw materials, the cooling loop is closed, 80ppm of hydroquinone stable triallyl cyanurate is added to stabilize triallyl cyanurate and chloropropene, then circulating water is started and heated to 40 ℃, and the stirring reaction is continued for 15 min. Subsequently, the unreacted chloropropene monomer was initially vacuum distilled at 40 ℃ and collected for recycle.
(3) After the distillation is completed, slowly cooling the mixture of triallyl trisulfate and sodium chloride left in the reactor to about 30 ℃, and slowly stirring for 1.5 hours until sodium chloride in the system is separated out and coarsened. Then, a tetrafluoroethylene filter membrane with the diameter of 0.22 μm is adopted for vacuum filtration to remove sodium chloride in the mixture, and clear and transparent filtrate is obtained, namely the product triallyl cyanurate monomer (427.4Kg), the yield is 95.8%, and the purity is 99.5%.
Example 2
The preparation method of triallyl trisulfate of this example comprises the following steps:
(1) pumping 516.5Kg (6750mol, excessive 50%) of chloropropene into a 1000L enamel reactor with a cooling loop and a circulating water bath loop, starting a stirring and cooling loop, and cooling the chloropropene monomer in the reactor to 0-2 ℃. Then, 364.8Kg (1500mol) of trisodium trithiocyanate was added slowly in portions (4 total portions, about 91Kg in each portion, with intervals of about 10-12 min in each portion). The trisodium trithiocyanate is quickly dissolved and reacts with chloropropene to release heat, the temperature in the reactor is controlled to be 3-10 ℃ through a cooling loop and the control of the feeding speed, the total feeding time is controlled to be 65min, and the reaction is continued for 20min after the feeding is finished.
(2) In order to realize the complete reaction of the raw materials, a cooling loop is closed, 60ppm of hydroquinone is added to stabilize triallyl cyanurate and chloropropene, circulating water is started again and heated to 40 ℃, and the stirring reaction is continued for 20 min. Subsequently, the unreacted chloropropene monomer was initially vacuum distilled at 40 ℃ and collected for recycle.
(3) After the distillation is completed, slowly cooling the mixture of triallyl trisulfate and sodium chloride left in the reactor to about 30 ℃, and slowly stirring for 2 hours until the sodium chloride in the system is separated out and coarsened. Then, a tetrafluoroethylene filter membrane with the diameter of 0.22 μm is adopted for vacuum filtration to remove sodium chloride in the mixture, and clear and transparent filtrate is obtained, namely the product triallyl cyanurate monomer (433.7Kg), the yield is 98.3%, and the purity is 99.6%.
Example 3
The preparation method of triallyl trisulfate of this example comprises the following steps:
(1) in a 1000L enamel reactor with a cooling loop and a circulating water bath loop, 516.5Kg (6750mol, 50% excess) of chloropropene is pumped in, a stirring and cooling loop is started, and the temperature of chloropropene in the reactor is reduced to 0-2 ℃. Then, 364.8Kg (1500mol) of trisodium trithiocyanate was added slowly in portions (5 total portions, about 73Kg each, with intervals of about 4-6 min). The trisodium trithiocyanate is quickly dissolved and reacts with chloropropene to release heat, the temperature in the reactor is controlled to be 3-10 ℃ through a cooling loop and the control of the feeding speed, the total feeding time is controlled to be 80min, and the reaction is continued for 20min after the feeding is finished.
(3) In order to realize the complete reaction of the raw materials, the cooling loop is closed, 50ppm of hydroquinone is added to stabilize triallyl cyanurate and chloropropene, then circulating water is started and heated to 43 ℃, and the stirring reaction is continued for 25 min. Subsequently, the unreacted chloropropene monomer was initially vacuum distilled at 43 ℃ and collected for recycle.
(3) After the distillation is completed, slowly cooling the mixture of triallyl trisulfate and sodium chloride left in the reactor to about 30 ℃, and slowly stirring for 2 hours until the sodium chloride in the system is separated out and coarsened. Then, a tetrafluoroethylene filter membrane with the diameter of 0.22 μm is adopted for vacuum filtration to remove sodium chloride in the mixture, and clear and transparent filtrate is obtained, namely the product triallyl cyanurate monomer (435.0Kg), the yield is 97.5%, and the purity is 99.9%.
FIG. 1 is a diagram of the product prepared in this example1H-NMR spectrum, 5.94ppm, 5.34,5.17ppm and 3.70ppm correspond to allyl a and allyl b and methylene (S-CH), respectively2-) chemical shift of the proton hydrogen. Wherein, the purity of the product is obtained by integral calculation from a nuclear magnetic spectrum.
Example 4
(1) In a 1000L enamel reactor with a cooling loop and a circulating water bath loop, 447.7Kg of chloropropene (5850mol, 30% excess) is pumped in, a stirring and cooling loop is started, and the temperature of chloropropene monomer in the reactor is reduced to 0-2 ℃. Then, 364.8Kg (1500mol) of trisodium trithiocyanate was added slowly in portions (5 total portions, about 73Kg each, with intervals of about 4-6 min). The trisodium trithiocyanate is quickly dissolved and reacts with chloropropene to release heat, the temperature in the reactor is controlled to be 3-10 ℃ through a cooling loop and the control of the feeding speed, the total feeding time is controlled to be 80min, and the reaction is continued for 20min after the feeding is finished.
(2) In order to realize the complete reaction of the raw materials, the cooling loop is closed, 50ppm of hydroquinone is added to stabilize triallyl cyanurate and chloropropene, then circulating water is started and heated to 43 ℃, and the stirring reaction is continued for 25 min. Subsequently, the unreacted chloropropene monomer was initially vacuum distilled at 43 ℃ and collected for recycle.
(3) After the distillation is completed, slowly cooling the mixture of triallyl trisulfate and sodium chloride left in the reactor to about 30 ℃, and slowly stirring for 1.5 hours until sodium chloride in the system is separated out and coarsened. Then, sodium chloride in the mixture is removed by vacuum filtration through a tetrafluoroethylene filter membrane with the diameter of 0.22 μm to obtain clear and transparent filtrate, namely the product triallyl cyanurate monomer (423.4Kg), wherein the yield is 94.9%, and the purity is 99.8%.
Example 5
The difference between this example and example 3 is: in the step (1), the addition amount of chloropropene is 550.9kg (7200mol, excess 60%), and after the temperature is raised to 43 ℃ in the step (2), the reaction is continued to be stirred for 40 min.
After completion of the distillation, the product was recovered by centrifugation to obtain 410.9Kg (92.1% yield) of triallyl cyanurate monomer product with a purity of 98.7%.
The above examples of the present invention are merely illustrative of the present invention and are not intended to limit the embodiments of the present invention. Variations and modifications in other variations will occur to those skilled in the art upon reading the foregoing description. Not all embodiments are exhaustive. All obvious changes and modifications of the present invention are within the scope of the present invention.
Claims (5)
1. The preparation method of triallyl cyanurate is characterized in that the structural formula of triallyl cyanurate is shown as the formula (I):
（Ⅰ）；
the triallyl trisulfate is obtained by the following preparation method, which comprises the following steps:
(1) synthesis of trisulfated triallyl cyanurate: adding chloropropene into a reactor, stirring, and adding trisodium trithiocyanate in batches, wherein the molar ratio of the trisodium trithiocyanate to the chloropropene is 1: 3.9-6.0, the feeding time of the trisodium trithiocyanate is 40-90 min, stirring and reacting for 10-40 min after the feeding is finished, and the temperature of a reaction system is controlled to be 3-12 ℃ in the whole process;
(2) heating for reaction: after the step (1) is finished, adding 20-100 ppm of polymerization inhibitor into a reaction system, heating the reaction system to 40-45 ℃, and continuously stirring for reaction for 10-40 min;
(3) vacuum distillation: after the step (2) is finished, carrying out vacuum distillation on the reacted mixed liquid at 40-45 ℃, recovering unreacted chloropropene monomers in the system, and recycling the recovered chloropropene as a reactant;
(4) separation and purification: after the distillation is completed, slowly cooling the mixture of the remaining triallyl trisulfate and sodium chloride in the reactor to 25-30 ℃ to separate out the sodium chloride, stirring for 0.5-1.5 h, and after the sodium chloride in the system is completely separated out, removing the sodium chloride through micro-membrane filtration or centrifugation to obtain the triallyl trisulfate;
adding the trisodium trithiocyanate in the step (1) in batches, wherein the interval between each batch is 4-15 min, and the reaction time in the step (1) is not more than 2h, wherein the reaction time is the time from the beginning of adding the trisodium trithiocyanate to the end of the reaction in the step (1); the trisodium trithiocyanate is added for 3-5 times, and the sum of the feeding time and the interval time of each batch is 80-100 min.
2. The method for preparing triallyl cyanurate according to claim 1, wherein the molar ratio of trisodium tripolyphosphate to chloropropene is 1: 4.5-5.1.
3. The method for preparing triallyl cyanurate according to claim 1, wherein the total reaction time of step (1) and step (2) is 1.5-3.0 h, and the total reaction time is the charging time and the interval time in step (1) and the heating time and the stirring reaction time in step (2).
4. The method for preparing triallyl cyanurate according to claim 1, wherein the microfilm in step (4) is a tetrafluoroethylene filter or a vinylidene fluoride filter of 0.22 μm.
5. The method according to claim 1, wherein the polymerization inhibitor is hydroquinone or a hydroquinone derivative.
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Citations (4)
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| US2676151A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
| JP2004090228A (en) * | 2002-08-29 | 2004-03-25 | Fuji Photo Film Co Ltd | Inkjet recording sheet |
| CN102491951A (en) * | 2011-12-02 | 2012-06-13 | 自贡天龙化工有限公司 | Production process of triallyl cyanurate |
| CN105669579A (en) * | 2016-03-18 | 2016-06-15 | 江苏科利新材料有限公司 | Method for preparing triallyl cyanurate |
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2017
- 2017-10-20 CN CN201710984821.7A patent/CN107739346B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676151A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
| JP2004090228A (en) * | 2002-08-29 | 2004-03-25 | Fuji Photo Film Co Ltd | Inkjet recording sheet |
| CN102491951A (en) * | 2011-12-02 | 2012-06-13 | 自贡天龙化工有限公司 | Production process of triallyl cyanurate |
| CN105669579A (en) * | 2016-03-18 | 2016-06-15 | 江苏科利新材料有限公司 | Method for preparing triallyl cyanurate |
Non-Patent Citations (2)
| Title |
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| "Inhibitory Effects of s-Triazines on the nitrification in Soil (Part 4) : Effects of Hydroxy-s-triazines and Their Derivatives, Miscellaneous s-Triazines and Hydro-s-tirazines";Ko WAKABAYASHI et al.;《Japanese Journal of Soil Science and Plant Nutrition》;19700625;第41卷(第6期);第237-245页 * |
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