WO2022011792A1 - 一种双季铵盐中间体的制备方法 - Google Patents

一种双季铵盐中间体的制备方法 Download PDF

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WO2022011792A1
WO2022011792A1 PCT/CN2020/111482 CN2020111482W WO2022011792A1 WO 2022011792 A1 WO2022011792 A1 WO 2022011792A1 CN 2020111482 W CN2020111482 W CN 2020111482W WO 2022011792 A1 WO2022011792 A1 WO 2022011792A1
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ammonium salt
amine
salt intermediate
reaction
tertiary amine
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PCT/CN2020/111482
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程终发
殷昂
周响
申义驰
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山东泰和水处理科技股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

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  • the patent of the present invention relates to the technical field of fine chemicals, in particular to a method for synthesizing a double quaternary ammonium salt intermediate.
  • diquaternary ammonium salt surfactants have received extensive attention due to their low toxicity, wide biological activity and good water solubility.
  • asymmetric biquaternary ammonium salts due to their asymmetry, high surface activity and unique physicochemical properties, are widely used in the fields of fungicides, synthesis of new molecular sieves, etc., with excellent performance.
  • a C10-C2-C12 type asymmetric diquaternary ammonium salt surfactant was synthesized from tertiary amine in isopropanol (Journal of Zhengzhou University, 2010).
  • the researchers also gave some other synthetic routes.
  • patent CN104211620B uses disulfonic acid ester to react with tertiary amine to generate asymmetric diquaternary ammonium salt
  • patent CN106674017B first uses long-chain halogenated alkane and medium and long chain ditertiary amine to react to generate intermediate, and then react with short-chain halogenated alkane to generate unbalanced Symmetrical biquaternary ammonium salt.
  • the company has formed a 1,3-dichloropropanol production chain of a certain scale, and proposed a production method for synthesizing biquaternary ammonium salt intermediates using 1,3-dichloropropanol as a linker, providing a relatively safe production method.
  • a healthy production environment broadens the downstream products and applications of 1,3-dichloropropanol.
  • the present invention provides a preparation method of the double quaternary ammonium salt intermediate.
  • a preparation technique of a double quaternary ammonium salt intermediate mainly comprises the following steps:
  • the flow mol ratio of pumping 1,3-dichloropropanol and R alkyl dimethylamine described in the step (1) is (1.5 ⁇ 2): 1, and the total flow of the two is that the hourly addition accounts for the reaction (1/10 ⁇ 1/6) of the total volume of the reactor, and the specific flow rate is determined by the total volume of the reactor.
  • 1,3-dichloropropanol is used as the linker of the biquaternary ammonium salt, and other auxiliary agents are not needed in the reaction process, and the acetone solution of amine is injected by dropping, and 1,3-dichloropropanol is As a reaction solvent and as a reaction raw material, dropwise addition of 1,3-dichloropropanol ensures the excess of 1,3-dichloropropanol, thereby ensuring the yield of the quaternary ammonium salt intermediate.
  • the accumulated acetone is added dropwise as a reaction solvent to ensure that Liquid volume to ensure production safety.
  • 1,3-dichloropropanol is used as the linker of the biquaternary ammonium salt, no additional auxiliary is needed in the reaction process, the reaction temperature is low, the reaction speed is fast, and the yield of the biquaternary ammonium salt intermediate is high.
  • the purity of 1,3-dichloropropanol is ⁇ 99% (produced by the company); the R alkyl dimethylamine is dodecyl dimethylamine, the purity is 99%, and the reaction kettle is a 10-cubic enamel reaction kettle with a pointed cone at the bottom .
  • Step 1 Add 2.5 cubic meters of acetone into the reaction kettle, start stirring, heat to 51°C with a shell-and-tube constant temperature heat exchanger, and pump 1,3-dichloropropane at the flow rates of 399kg/h and 330kg/h, respectively. Alcohol and dodecyl dimethylamine were continuously heated up in the reaction kettle during the feeding process, and after 50 min of dropwise addition, the temperature in the reaction kettle rose to 81°C.
  • Step 2 Continue feeding according to the above-mentioned flow rate, keep the temperature in the reaction kettle at 89 ⁇ 1 °C under stirring, start to separate out solids at the bottom of the kettle, and transfer the solid-liquid mixture enriched at the point cone at the bottom of the kettle to a centrifuge to separate the mother liquor and solid biquad. Crude ammonium salt intermediate.
  • Step 3 The crude product of the double quaternary ammonium salt intermediate is transferred to a vacuum drying oven, dried at 105 ⁇ 5°C under -0.1MPa pressure, and the residual organic matter is separated and added to the mother liquor to obtain the remaining solid double quaternary ammonium salt intermediate 3-chloro -2-Hydroxypropyl dodecyl dimethyl ammonium chloride, the separated mother liquor and organic phase are injected into the reaction kettle for recycling to realize continuous production.
  • the product was tested, and the primary conversion rate (calculated as tertiary amine) was 90.46%, the content of 3-chloro-2-hydroxypropyl dodecyldimethyl ammonium chloride was 99.45%, and the content of ammonium salt was 0.17%.
  • Step 1 Add 2.5 cubic meters of acetone into the reaction kettle, start stirring, heat it to 50°C with a shell-and-tube constant temperature heat exchanger, and pump 1,3-dichloropropane at the flow rates of 480kg/h and 530kg/h, respectively. Alcohol and dodecyl dimethylamine were continuously heated up in the reaction kettle during the feeding process, and after 58 minutes of dropwise addition, the temperature in the reaction kettle rose to 80°C.
  • Step 2 Continue feeding according to the above-mentioned flow rate, keep the temperature in the reaction kettle at 81 ⁇ 1 °C under stirring, start to separate out solids at the bottom of the kettle, and transfer the solid-liquid mixture enriched at the point cone at the bottom of the kettle to a centrifuge to separate the mother liquor and the solid biquad. Crude ammonium salt intermediate.
  • Step 3 The crude product of the double quaternary ammonium salt intermediate is transferred to a vacuum drying oven, dried at 105 ⁇ 5°C under -0.1MPa pressure, and the residual organic matter is separated and added to the mother liquor to obtain the remaining solid double quaternary ammonium salt intermediate 3-chloro -2-Hydroxypropyl dodecyl dimethyl ammonium chloride, the separated mother liquor and organic phase are injected into the reaction kettle for recycling to realize continuous production.
  • the product has been tested, and the primary conversion rate (calculated as tertiary amine) is 86.81%, the content of 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride is 99.38%, and the content of ammonium salt is 0.13%.
  • the temperature of the reaction kettle was controlled at 115 ⁇ 1° C., and other conditions remained unchanged, as in Example 1, to obtain 2943.7kg of 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride.
  • the primary conversion rate (calculated as tertiary amine) is 93.22%, the content of 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride is 89.82%; the content of biquaternary ammonium salt is 9.76%; the content of ammonium salt 0.45%.
  • Step 1 Add 148g 1,2-dichloroethane and 200g isopropanol to the reaction kettle, turn on stirring, heat up to 81 ⁇ 1°C, add dodecyl dimethylamine dropwise at a flow rate of 106g/h, add dropwise The process maintained the reactor temperature at 81 ⁇ 1°C.
  • Step 2 After 2.1h, the dropwise addition was completed, and the reaction was carried out for 1h under the reflux state of the reaction kettle. Under the pressure of -0.1MPa, the solvent and excess 1,2-dichloroethane were distilled out to obtain the intermediate 2-chloroethyldecane 288.7 g of dialkyldimethylammonium chloride.
  • the conversion rate (calculated as tertiary amine) is 90.52%, the content of 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride is 97.82%; the content of biquaternary ammonium salt is 1.76%; the content of ammonium salt is 0.45% %.
  • Step 1 Add 300g of pure water to the 1L reaction kettle, turn on stirring, heat up to 95 ⁇ 1°C, and add 1,3-dichloropropanol and dodecane dropwise at the flow rates of 32.25g/h and 53.35g/h respectively. dimethylamine, and the temperature of the reaction kettle was maintained at 95-100°C during the dropwise addition.
  • Step 2 After 4.3h, the dropwise addition was completed, and the reaction was carried out for 1h under the reflux state of the reaction kettle. The reaction solution was completely clarified from turbidity. The reaction solution was distilled under -0.1MPa pressure to remove water and unreacted materials to obtain the intermediate 2-chlorine Ethyldodecyldimethylammonium chloride 345.2g.
  • the product has been tested, and the primary conversion rate (calculated as tertiary amine) is 88.16%; the content of 3-chloro-2-hydroxypropyl dodecyl dimethyl ammonium chloride is 90.85%; the content of biquaternary ammonium salt is 8.66%, and the content of ammonium salt 0.17%.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明提供了一种双季铵盐中间体的制备工艺，用1,3-二氯丙醇与长碳链二甲胺在丙酮中反应生成一种双季铵盐中间体。本发明采用1,3-二氯丙醇做连接基，依托于1,3-二氯丙醇生产线，扩展了1,3-二氯丙醇的产业链及应用；本发明生产的双季铵盐中间体纯度高，易分离；本发明实现连续化生产，有利于工业推广。

Description

一种双季铵盐中间体的制备方法 技术领域
本发明专利涉及精细化学品技术领域，特别涉及一种双季铵盐中间体的合成方法。
背景技术
近年来，双季铵盐表面活性剂由于其具有低毒、广泛的生物活性和良好的水溶性等特点受到广泛关注。其中，不对称双季铵盐，由于其所具备的不对称性、高表面活性及独特的物化性质，广发应用于杀菌剂、新型分子筛的合成等领域，性能优异。
目前，不对称双季铵盐的合成研究已取得一定成就，主要是以环氧氯丙烷或短链的二卤代烷为连接基，与不同型号的二甲基叔胺进行反应合成。如余宗学等用环氧氯丙烷和二甲基叔胺生成中间体，再与长链油酸咪唑啉反应生成不对称双季铵盐；王留成等用1,2-二溴乙烷和二甲基叔胺在异丙醇条件下，合成了一种C10-C2-C12型不对称双季铵盐表面活性剂(郑州大学学报，2010)。除此之外，研究人员也给出其他一些合成途径。如专利CN104211620B使用二磺酸酯与叔胺反应生成不对称双季铵盐；专利CN106674017B先用长链卤代烷烃和中长链的二叔胺反应生成中间体，再与短链卤代烷烃反应生成不对称双季铵盐。
要合成高含量的不对称双季铵盐，必须控制中间体的转化程度，在保证大量中间体产生的同时，避免继续反应生成对称双季铵盐。环氧氯丙烷由于其不同的反应活性基团，能很好的控制中间体的产生，但其对人健康的危害性大，且化学性质活泼，容易引起火灾和爆炸。在生产安全和职业健康角度，应选用更加安全健康的连接基进行反应。本公司已形成一定规模的1,3-二氯丙醇生产链线，提出了一种利用1,3-二氯丙醇为连接基合成双季铵盐中间体的生产方法，提供了相对安全健康的生产环境，扩宽了1,3-二氯丙醇的下游产品及应用。
发明内容
针对现有技术中存在的季铵盐中间体转化率低，反应复杂的问题，本发明提供一种双季铵盐中间体的制备方法。
一种双季铵盐中间体的制备工艺，主要包括以下步骤：
(1)将一定量的丙酮加入反应釜中，开启搅拌，加热到50℃后，按一定流量分别泵入1,3-二氯丙醇和R烷基二甲胺，加料过程反应釜内持续升温，滴加约1h后，反应釜内温度升至80℃。
(2)继续持续加料，搅拌下保持反应釜内温度80～90℃，釜底开始分离富集固体中间体产物，釜底富含中间体的混合液收集经分离得母液和固体双季铵盐中间体粗品。
(3)双季铵盐中间体粗品经-0.1MPa压力下真空干燥，分离有机物和双季铵盐中间体3-氯-2-羟丙基R烷基二甲基氯化铵，母液和有机物打入反应釜中循环使用，实现连续化生产其中，步骤(1)中所述丙酮加入量为反应釜内总体积的(1/4～1/3)，R烷基二甲胺的R为八、十、十二、十四。
其中，步骤(1)中所述泵入1,3-二氯丙醇与R烷基二甲胺的流量摩尔比为(1.5～2):1，两者总流量为每小时加入量占反应釜总体积的(1/10～1/6)，具体流量由反应釜总体积决定。
本发明采用1,3-二氯丙醇作为双季铵盐的连接体，反应过程中不需要采用其他助剂，通过滴加的方式注入胺的丙酮溶液，1,3-二氯丙醇即作为反应溶剂又作为反应原料，滴加保证1,3-二氯丙醇的过量，从而保证了季铵盐中间体的产率，反应末期，滴加积累的丙酮作为反应溶剂，保证反应釜内液量，保证生产安全。
本发明有益效果
本发明以1,3-二氯丙醇作为双季铵盐的连接体，反应过程中不需要额外添加助剂，反应温度低，反应速度快，双季铵盐中间体产率高。
具体实施方式
下面通过实例详细地描述本发明，这些实例仅仅是说明性的，不代表限制本发明的适用范围，根据本文的公开，本领域技术人员能在本发明范围内对试剂、催化剂和反应工艺条件进行改变。凡根据本发明精神实质所做的等效变化或者修改，都应涵盖在本发明的保护范围之内。
实施例所用部分原料和设备规格：
1,3-二氯丙醇纯度≥99％(公司自产)；R烷基二甲胺为十二烷基二甲胺，纯度99％，反应釜为10立方底部尖锥形的搪瓷反应釜。
实施例1
步骤一：将2.5立方的丙酮加入反应釜中，开启搅拌，用管壳式恒温换热器加热到51℃后，分别按399kg/h和330kg/h的流量泵入1,3-二氯丙醇和十二烷基二甲胺，加料过程反应釜内持续升温，滴加50min后，反应釜内温度升至81℃。
步骤二：继续按上述流量加料，搅拌下保持反应釜内温度89±1℃，釜底开始析出固体，釜底尖锥处富集的固液混合液转移至离心机分离得母液和固体双季铵盐中间体粗品。
步骤三：双季铵盐中间体粗品转至真空干燥箱，在105±5℃，-0.1MPa压力下烘干，分离出残余有机物加入母液中，得剩余固体双季铵盐中间体3-氯-2-羟丙基十二烷基二甲基氯化铵，分离所得母液及有机相打入反应釜中循环使用，实现连续化生产。
以一个反应周期计，得3-氯-2-羟丙基十二烷基二甲基氯化铵1910.4kg。
产品经检测，一次转化率(以叔胺计)90.46％，3-氯-2-羟丙基十二烷基二甲基氯化铵含量99.45％；铵盐含量0.17％。
实施例2
步骤一：将2.5立方的丙酮加入反应釜中，开启搅拌，用管壳式恒温换热器加热到50℃后，分别按480kg/h和530kg/h的流量泵入1,3-二氯丙醇和十二烷基二甲胺，加料过程反应釜内持续升温，滴加58min后，反应釜内温度升至80℃。
步骤二：继续按上述流量加料，搅拌下保持反应釜内温度81±1℃，釜底开始析出固体，釜底尖锥处富集的固液混合液转移至离心机分离得母液和固体双季铵盐中间体粗品。
步骤三：双季铵盐中间体粗品转至真空干燥箱，在105±5℃，-0.1MPa压力下烘干，分离出残余有机物加入母液中，得剩余固体双季铵盐中间体3-氯-2-羟丙基十二烷基二甲基氯 化铵，分离所得母液及有机相打入反应釜中循环使用，实现连续化生产。
以一个反应周期计，得3-氯-2-羟丙基十二烷基二甲基氯化铵2943.7kg。
产品经检测，一次转化率(以叔胺计)86.81％，3-氯-2-羟丙基十二烷基二甲基氯化铵含量99.38％；铵盐含量0.13％。
对比例1(高温反应)
反应釜温度控制在115±1℃，其他条件不变，同实施例1，得3-氯-2-羟丙基十二烷基二甲基氯化铵2943.7kg。
得3-氯-2-羟丙基十二烷基二甲基氯化铵2245.5kg。
产品经检测，一次转化率(以叔胺计)93.22％，3-氯-2-羟丙基十二烷基二甲基氯化铵含量89.82％；双季铵盐含量9.76％；铵盐含量0.45％。
对比例2(使用1,2-二氯乙烷与十二烷基二甲胺反应)
步骤一：向反应釜中加入148g1,2-二氯乙烷和200g异丙醇，开启搅拌，升温至81±1℃，按106g/h的流量滴加十二烷基二甲胺，滴加过程保持反应釜温度在81±1℃。
步骤二：2.1h后滴加完毕，反应釜回流状态下反应1h，在-0.1MPa压力下，外蒸出溶剂和过量的1,2-二氯乙烷，得中间体2-氯乙基十二烷基二甲基氯化铵288.7g。
产品经检测，转化率(以叔胺计)90.52％，3-氯-2-羟丙基十二烷基二甲基氯化铵含量97.82％；双季铵盐含量1.76％；铵盐含量0.45％。
对比例3(其他专利报道的连续化生产方法)
步骤一：向1L反应釜中加入300g的纯水，开启搅拌，升温至95±1℃，分别按32.25g/h和53.35g/h的流量滴加1,3-二氯丙醇和十二烷基二甲胺，滴加过程保持反应釜温度在95～100℃。
步骤二：4.3h后滴加完毕，反应釜回流状态下反应1h，反应液由浑浊完全变澄清，将反应液在-0.1MPa压力下，外蒸出水和未反应物料，得中间体2-氯乙基十二烷基二甲基氯化铵345.2g。
产品经检测，一次转化率(以叔胺计)88.16％；3-氯-2-羟丙基十二烷基二甲基氯化铵含量90.85％；双季铵盐含量8.66％，铵盐含量0.17％。

Claims (6)

  1. 一种双季铵盐中间体的制备方法，其特征在于，包括以下步骤:
    (1)将1,3-二氯丙醇加入反应釜中，开启搅拌，滴加胺的丙酮溶液，加料过程反应釜内持续升温至反应温度；
    (2)继续持续加料，搅拌下保持反应温度，釜底开始分离富集固体中间体产物，釜底富含中间体的混合液收集经分离得母液和固体双季铵盐中间体粗品；
    (3)提纯得双季铵盐中间体3-氯-2-羟丙基R烷基二甲基氯化铵。
  2. 根据权利要求1所述的方法，其特征在于，所述的丙酮总量为反应釜总体积的1/4～1/3，所述的胺为含烷基碳链10～20的烷基二甲基叔胺。
  3. 根据权利要求1所述的方法，其特征在于，所述的胺为八烷基二甲基叔胺、十烷基二甲基叔胺、十二烷基二甲基叔胺、十四烷基二甲基叔胺。
  4. 根据权利要求1所述的方法，其特征在于，所述的1,3-二氯丙醇与胺摩尔比为1.5～2:1，两者总体积量为反应釜总体积的1/10-1/6。
  5. 根据权利要求1所述的方法，其特征在于，所述的胺的丙酮溶液的滴加时间为1-3h；所述的反应温度为80-90℃。
  6. 根据权利要求1所述的方法，其特征在于，所述的提纯具体为：双季铵盐中间体粗品经-0.1MPa压力下真空干燥，分离有机物和双季铵盐中间体3-氯-2-羟丙基R烷基二甲基氯化铵，母液和有机物打入反应釜中循环使用，实现连续化生产。
PCT/CN2020/111482 2020-07-13 2020-08-26 一种双季铵盐中间体的制备方法 WO2022011792A1 (zh)

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