WO2022016635A1 - 三烯丙基异三聚酸酯生产工艺 - Google Patents

三烯丙基异三聚酸酯生产工艺 Download PDF

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WO2022016635A1
WO2022016635A1 PCT/CN2020/108864 CN2020108864W WO2022016635A1 WO 2022016635 A1 WO2022016635 A1 WO 2022016635A1 CN 2020108864 W CN2020108864 W CN 2020108864W WO 2022016635 A1 WO2022016635 A1 WO 2022016635A1
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triallyl
isotripolyester
dimethylformamide
washing
production technique
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PCT/CN2020/108864
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English (en)
French (fr)
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薄纯金
宋朋斌
张延军
王国力
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山东海益化工科技有限公司
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Publication of WO2022016635A1 publication Critical patent/WO2022016635A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • the invention relates to the technical field of chemical production technology, in particular to a production technology of triallyl isotripolyester.
  • Triallyl isotripolyester is a multifunctional olefin monomer containing aromatic heterocycles. It is mainly used as a crosslinking agent and modifier for multiple purposes. It is used to modify rubber materials, composite materials, resin materials and fiber materials. It has a wide range of applications in terms of properties, such as increasing the crosslinking density of the material, increasing the graft introduction rate, shortening the crosslinking time, improving the scorch resistance, enhancing the hardness of the vulcanizate, improving the chemical resistance, tensile strength, impact resistance strength and bending strength.
  • the present invention aims to solve at least one of the technical problems existing in the prior art or related technologies.
  • an object of the present invention is to provide a kind of triallyl isotrimeric ester production technology, take sodium cyanate as raw material and react with allyl chloride, make solvent with dimethylformamide, take potassium bromide and trimethyl bromide as solvent Ethylamine is used as a catalyst to produce triallyl isotripolyester, and it is purified by vacuum distillation in a molecular distiller.
  • the obtained triallyl isotripolyester has a purity of over 99% and a yield of 93.5%.
  • the above, and dimethylformamide can be recycled, and the aqueous solution generated after the alkali washing of the sheet is reused to remove sodium chloride and water-soluble impurities from the mixed solution after washing and vacuum distillation. Ester purity and yield, while saving energy.
  • the technical scheme of the present invention provides a triallyl isotripolyester production process, comprising the following steps:
  • the synthetic mother liquor in the reactor is sent into the cooler to be cooled by circulating water, then sent to the distiller for underpressure distillation, the dimethylformamide is removed, and it is sent into the dimethylformamide overhead tank for recycling. ;
  • the mixed solution after vacuum distillation is washed with water to remove sodium chloride and water-soluble impurities, and then sent to a molecular distiller for vacuum distillation and purification, followed by acid washing with hydrochloric acid and alkali washing with flakes to obtain triallyl isotrimethylbenzene.
  • Polyester The mixed solution after vacuum distillation is washed with water to remove sodium chloride and water-soluble impurities, and then sent to a molecular distiller for vacuum distillation and purification, followed by acid washing with hydrochloric acid and alkali washing with flakes to obtain triallyl isotrimethylbenzene. Polyester.
  • the catalyst is a mixture of potassium bromide and triethylamine, and the mass ratio of the potassium bromide and the triethylamine is: 1:0.8-1.2.
  • the hydrochloric acid pickling adopts a hydrochloric acid solution with a mass concentration of 1%-1.5%.
  • the alkaline washing of the sheet is a sodium hydroxide solution with a mass concentration of 0.5%-1%.
  • the distillation temperature for vacuum distillation and purification in the molecular still is 100°C to 180°C, and the vacuum degree is 0.3 mmHg to 0.5 mmHg.
  • the temperature of the reaction kettle is heated by steam PID automatic temperature control, and the heating medium is saturated steam with a pressure of 0.7 MPa.
  • the aqueous solution generated after the alkali washing of the sheet is reused to remove sodium chloride and water-soluble impurities by using the mixed solution after washing and vacuum distillation.
  • the invention discloses a production process of triallyl isotripolyester, and those skilled in the art can learn from the content of this paper and appropriately improve process parameters to achieve. It should be particularly pointed out that all similar substitutions and modifications are obvious to those skilled in the art, and they are deemed to be included in the present invention.
  • the method and application of the present invention have been described through the preferred embodiments, and it is obvious that relevant persons can make changes or appropriate changes and combinations of the methods and applications described herein without departing from the content, spirit and scope of the present invention to achieve and Apply the technology of the present invention.
  • triallyl isotripolyester is as follows:
  • the synthetic mother liquor in the reactor is sent into the cooler to be cooled by circulating water, then sent into the distiller for underpressure distillation, removed the dimethylformamide solvent, sent into the dimethylformamide overhead tank for recycling , improve the utilization rate of dimethylformamide, reduce production cost and energy consumption;
  • the mixed solution after vacuum distillation was washed with water to remove sodium chloride and water-soluble impurities, and then sent to a molecular distiller for vacuum distillation and purification, the distillation temperature was 150 ° C, and the vacuum degree was 0.4 mmHg;
  • the product obtained by vacuum distillation and refining is pickled with a hydrochloric acid solution with a mass concentration of 1.5% to treat the alkalinity in the product, and then caustic washed with a sodium hydroxide solution with a mass concentration of 1% to prevent excessive pickling and ensure product quality.
  • the aqueous solution generated after alkali washing of the sheet is reused to remove sodium chloride and water-soluble impurities by using the mixed solution after washing and vacuum distillation to obtain triallyl isotripolyester.
  • triallyl isotripolyester is as follows:
  • reaction kettle In the 3000L reaction kettle, add 1000kg of dimethylformamide, 6.5kg of anhydrous calcium chloride, then add 450kg of sodium cyanate and 540kg of propylene chloride into the reaction kettle, and maintain the automatic temperature control heating by the saturated steam of 0.7MPa pressure.
  • the reaction temperature was 120°C, 7kg of potassium bromide and 7.5kg of triethylamine were added, and sodium cyanate and propylene chloride were synthesized in the reaction kettle, and the reaction time was 3h;
  • the synthetic mother liquor in the reactor is sent into the cooler to be cooled by circulating water, then sent into the distiller for underpressure distillation, removed the dimethylformamide solvent, sent into the dimethylformamide overhead tank for recycling , improve the utilization rate of dimethylformamide, reduce production cost and energy consumption;
  • the mixed solution after vacuum distillation is washed with water to remove sodium chloride and water-soluble impurities, and then sent to a molecular distiller for vacuum distillation and purification, the distillation temperature is 180 ° C, and the vacuum degree is 0.5 mmHg;
  • the product obtained by vacuum distillation and refining is pickled with hydrochloric acid solution with a mass concentration of 1%, and the alkalinity in the product is treated, and then alkaline washing with a sodium hydroxide solution with a mass concentration of 0.5% is used to prevent excessive pickling and ensure product quality.
  • the aqueous solution generated after alkali washing of the sheet is reused to remove sodium chloride and water-soluble impurities by using the mixed solution after washing and vacuum distillation to obtain triallyl isotripolyester.
  • triallyl isotripolyester is as follows:
  • reaction kettle In the 3000L reaction kettle, add 1000kg dimethylformamide, 6.5kg anhydrous calcium chloride, then add 450kg sodium cyanate and 585kg propylene chloride into the reaction kettle, maintain by the saturated steam PID automatic temperature control heating of pressure 0.7MPa
  • the reaction temperature was 120°C, 3kg of potassium bromide and 2.5kg of triethylamine were added, and sodium cyanate and propylene chloride were synthesized in the reaction kettle, and the reaction time was 2h;
  • the synthetic mother liquor in the reactor is sent into the cooler to be cooled by circulating water, then sent into the distiller for underpressure distillation, removed the dimethylformamide solvent, sent into the dimethylformamide overhead tank for recycling , improve the utilization rate of dimethylformamide, reduce production cost and energy consumption;
  • the mixed solution after the vacuum distillation was washed with water to remove sodium chloride and water-soluble impurities, and then sent to the molecular distiller for vacuum distillation and purification, and the distillation temperature was 150 ° C, and the vacuum degree was 0.3 mmHg;
  • the product obtained by vacuum distillation and refining is pickled with a hydrochloric acid solution with a mass concentration of 1.5% to treat the alkalinity in the product, and then caustic washed with a sodium hydroxide solution with a mass concentration of 1% to prevent excessive pickling and ensure product quality.
  • the aqueous solution generated after alkali washing of the sheet is reused to remove sodium chloride and water-soluble impurities by using the mixed solution after washing and vacuum distillation to obtain triallyl isotripolyester.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

一种三烯丙基异三聚酸酯生产工艺，包括以下步骤：将二甲基甲酰胺、无水氯化钙加入反应釜中，之后将氰酸钠与氯丙烯加入反应釜中，维持反应温度在110℃～130℃，加入催化剂，氰酸钠与氯丙烯在反应釜内进行合成反应，反应时间在2h～3h，氰酸钠与氯丙烯的质量比为1：1.1-1.3，催化剂的质量为反应物质量的0.5％-1.5％；将反应釜内的合成母液送入冷却器中冷却，之后减压蒸馏，将二甲基甲酰胺脱除，送入二甲基甲酰胺高位槽中循环使用；减压蒸馏后的混合溶液加水洗涤，之后真空蒸馏精制，之后进行盐酸酸洗和片碱碱洗，即可得到三烯丙基异三聚酸酯。三烯丙基异三聚酸酯纯度可达99％以上，收率可达93.5％以上，且生产工艺简单，可控性强。

Description

三烯丙基异三聚酸酯生产工艺 技术领域
本发明涉及化学品生产工艺技术领域，具体而言，涉及一种三烯丙基异三聚酸酯生产工艺。
背景技术
三烯丙基异三聚酸酯是一种含芳杂环的多功能烯烃单体，主要用于多重用途的交联剂和改性剂，对橡胶材料、复合材料、树脂材料以及纤维材料改性方面有着广泛的应用，如提高材料的交联密度、增大接枝导入率、缩短交联时间、提高抗焦烧能力、增强硫化胶硬度、提高耐化学腐蚀性能、拉伸强度、抗冲击强度以及弯曲强度等。
然而，在相关技术中的三烯丙基异三聚酸酯的生产规模较小，纯度和产量较低，能耗较高，难以满足市场对于生产的需求。
发明内容
本发明旨在至少解决现有技术或相关技术中存在的技术问题之一。
为此，本发明的一个目的在于提供一种三烯丙基异三聚酸酯生产工艺，以氰酸钠为原料与氯丙烯反应，用二甲基甲酰胺作溶剂，以溴化钾和三乙胺作为催化剂进行三烯丙基异三聚酸酯生产，且在分子蒸馏器中真空蒸馏精制，得到的三烯丙基异三聚酸酯纯度可达99％以上，收率可达93.5％以上，而且二甲基甲酰胺可循环使用，片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质，在提升三烯丙基异三聚酸酯纯度和收率的同时，节约了能耗。
为了实现上述目的，本发明的技术方案提供了一种三烯丙基异三聚酸酯生产工艺，包括以下步骤：
将二甲基甲酰胺、无水氯化钙加入反应釜中，之后将氰酸钠与氯丙烯 加入反应釜中，通过蒸汽加热维持反应温度在110℃～130℃，加入催化剂，氰酸钠与氯丙烯在反应釜内进行合成反应，反应时间在2h～3h，所述氰酸钠与氯丙烯的质量比为1：1.1-1.3，所述催化剂的质量为反应物质量的0.5％-1.5％；
将反应釜内的合成母液送入冷却器中通过循环水进行冷却，之后送入蒸馏器中进行减压蒸馏，将二甲基甲酰胺脱除，送入二甲基甲酰胺高位槽中循环使用；
减压蒸馏后的混合溶液加水洗涤脱除氯化钠和水溶性杂质，之后送入分子蒸馏器中真空蒸馏精制，之后进行盐酸酸洗和片碱碱洗，即可得到三烯丙基异三聚酸酯。
优选地，所述催化剂为溴化钾和三乙胺的混合物，所述溴化钾和所述三乙胺的质量比为：1:0.8-1.2。
优选地，所述盐酸酸洗为采用质量浓度为1％-1.5％的盐酸溶液。
优选地，所述片碱碱洗为采用质量浓度为0.5％-1％的氢氧化钠溶液。
优选地，在所述分子蒸馏器中真空蒸馏精制的蒸馏温度为100℃～180℃，真空度为0.3mmHg～0.5mmHg。
优选地，所述反应釜的温度通过蒸汽PID自动控温加热，加热介质为压力0.7MPa的饱和蒸汽。
优选地，所述片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质。
本发明提出的三烯丙基异三聚酸酯生产工艺具有以下有益技术效果：
(1)以氰酸钠为原料与氯丙烯反应，用二甲基甲酰胺作溶剂，以溴化钾和三乙胺作为催化剂进行三烯丙基异三聚酸酯生产，且在分子蒸馏器中真空蒸馏精制，生产工艺简单，可控性强，三烯丙基异三聚酸酯纯度可达99％以上，收率可达93.5％以上。
(2)通过减压蒸馏脱除产物中的二甲基甲酰胺溶剂，二甲基甲酰胺溶剂可循环使用，节约了资源和能耗。
(3)片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质，节约了资源和能耗。
本发明的附加方面和优点将在下面的描述部分中给出，部分将从下面 的描述中变得明显，或通过本发明的实践了解到。
具体实施方式
本发明公开了一种三烯丙基异三聚酸酯生产工艺，本领域技术人员可以借鉴本文内容，适当改进工艺参数实现。特别需要指出的是，所有类似的替换和改动对本领域技术人员来说是显而易见的，它们都被视为包括在本发明。本发明的方法及应用已经通过较佳实施例进行了描述，相关人员明显能在不脱离本发明内容、精神和范围内对本文所述的方法和应用进行改动或适当变更与组合，来实现和应用本发明技术。
下面结合实施例，进一步阐述本发明：
实施例1
三烯丙基异三聚酸酯生产工艺如下：
在3000L反应釜中，加入1000kg二甲基甲酰胺，6.5kg无水氯化钙，之后将450kg氰酸钠与495kg氯丙烯加入反应釜中，通过压力0.7MPa的饱和蒸汽PID自动控温加热维持反应温度在120℃，加入4.5kg溴化钾和4.5kg三乙胺，氰酸钠与氯丙烯在反应釜内进行合成反应，反应时间为2.5h；
将反应釜内的合成母液送入冷却器中通过循环水进行冷却，之后送入蒸馏器中进行减压蒸馏，脱除二甲基甲酰胺溶剂，送入二甲基甲酰胺高位槽中循环使用，提高了二甲基甲酰胺的利用率，降低了生产成本和能耗；
减压蒸馏后的混合溶液加水洗涤脱除氯化钠和水溶性杂质，之后送入分子蒸馏器中真空蒸馏精制，蒸馏温度为150℃，真空度为0.4mmHg；
真空蒸馏精制得到的产品采用质量浓度为1.5％的盐酸溶液进行酸洗，处理产品中的碱度，之后采用质量浓度为1％的氢氧化钠溶液碱洗，防止酸洗过量，保证产品质量，片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质，即可得到三烯丙基异三聚酸酯。
以此生产工艺制备的三烯丙基异三聚酸酯的纯度为99.2％，收率为93.6％。
实施例2
三烯丙基异三聚酸酯生产工艺如下：
在3000L反应釜中，加入1000kg二甲基甲酰胺，6.5kg无水氯化钙，之后将450kg氰酸钠与540kg氯丙烯加入反应釜中，通过压力0.7MPa的饱和蒸汽PID自动控温加热维持反应温度在120℃，加入7kg溴化钾和7.5kg三乙胺，氰酸钠与氯丙烯在反应釜内进行合成反应，反应时间为3h；
将反应釜内的合成母液送入冷却器中通过循环水进行冷却，之后送入蒸馏器中进行减压蒸馏，脱除二甲基甲酰胺溶剂，送入二甲基甲酰胺高位槽中循环使用，提高了二甲基甲酰胺的利用率，降低了生产成本和能耗；
减压蒸馏后的混合溶液加水洗涤脱除氯化钠和水溶性杂质，之后送入分子蒸馏器中真空蒸馏精制，蒸馏温度为180℃，真空度为0.5mmHg；
真空蒸馏精制得到的产品采用质量浓度为1％的盐酸溶液进行酸洗，处理产品中的碱度，之后采用质量浓度为0.5％的氢氧化钠溶液碱洗，防止酸洗过量，保证产品质量，片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质，即可得到三烯丙基异三聚酸酯。
以此生产工艺制备的三烯丙基异三聚酸酯的纯度为99.1％，收率为93.5％。
实施例3
三烯丙基异三聚酸酯生产工艺如下：
在3000L反应釜中，加入1000kg二甲基甲酰胺，6.5kg无水氯化钙，之后将450kg氰酸钠与585kg氯丙烯加入反应釜中，通过压力0.7MPa的饱和蒸汽PID自动控温加热维持反应温度在120℃，加入3kg溴化钾和2.5kg三乙胺，氰酸钠与氯丙烯在反应釜内进行合成反应，反应时间为2h；
将反应釜内的合成母液送入冷却器中通过循环水进行冷却，之后送入蒸馏器中进行减压蒸馏，脱除二甲基甲酰胺溶剂，送入二甲基甲酰胺高位槽中循环使用，提高了二甲基甲酰胺的利用率，降低了生产成本和能耗；
减压蒸馏后的混合溶液加水洗涤脱除氯化钠和水溶性杂质，之后送入 分子蒸馏器中真空蒸馏精制，蒸馏温度为150℃，真空度为0.3mmHg；
真空蒸馏精制得到的产品采用质量浓度为1.5％的盐酸溶液进行酸洗，处理产品中的碱度，之后采用质量浓度为1％的氢氧化钠溶液碱洗，防止酸洗过量，保证产品质量，片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质，即可得到三烯丙基异三聚酸酯。
以此生产工艺制备的三烯丙基异三聚酸酯的纯度为99.0％，收率为93.5％。
以上所述仅是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。

Claims (7)

  1. 一种三烯丙基异三聚酸酯生产工艺，其特征在于，包括以下步骤：
    将二甲基甲酰胺、无水氯化钙加入反应釜中，之后将氰酸钠与氯丙烯加入反应釜中，通过蒸汽加热维持反应温度在110℃～130℃，加入催化剂，氰酸钠与氯丙烯在反应釜内进行合成反应，反应时间在2h～3h，所述氰酸钠与氯丙烯的质量比为1：1.1-1.3，所述催化剂的质量为反应物质量的0.5％-1.5％；
    将反应釜内的合成母液送入冷却器中通过循环水进行冷却，之后送入蒸馏器中进行减压蒸馏，将二甲基甲酰胺脱除，送入二甲基甲酰胺高位槽中循环使用；
    减压蒸馏后的混合溶液加水洗涤脱除氯化钠和水溶性杂质，之后送入分子蒸馏器中真空蒸馏精制，之后进行盐酸酸洗和片碱碱洗，即可得到三烯丙基异三聚酸酯。
  2. 根据权利要求1所述的三烯丙基异三聚酸酯生产工艺，其特征在于，
    所述催化剂为溴化钾和三乙胺的混合物，所述溴化钾和所述三乙胺的质量比为：1:0.8-1.2。
  3. 根据权利要求1所述的三烯丙基异三聚酸酯生产工艺，其特征在于，
    所述盐酸酸洗为采用质量浓度为1％-1.5％的盐酸溶液。
  4. 根据权利要求1所述的三烯丙基异三聚酸酯生产工艺，其特征在于，
    所述片碱碱洗为采用质量浓度为0.5％-1％的氢氧化钠溶液。
  5. 根据权利要求1所述的三烯丙基异三聚酸酯生产工艺，其特征在于，
    在所述分子蒸馏器中真空蒸馏精制的蒸馏温度为100℃～180℃，真空度为0.3mmHg～0.5mmHg。
  6. 根据权利要求1所述的三烯丙基异三聚酸酯生产工艺，其特征在于，
    所述反应釜的温度通过蒸汽PID自动控温加热，加热介质为压力0.7MPa的饱和蒸汽。
  7. 根据权利要求1所述的三烯丙基异三聚酸酯生产工艺，其特征在于，
    所述片碱碱洗后生成的水溶液重复利用洗涤减压蒸馏后的混合溶液脱除氯化钠和水溶性杂质。
PCT/CN2020/108864 2020-07-23 2020-08-13 三烯丙基异三聚酸酯生产工艺 WO2022016635A1 (zh)

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