WO2016026196A1 - 一种新型双长链酯基季铵盐及其合成工艺 - Google Patents

一种新型双长链酯基季铵盐及其合成工艺 Download PDF

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WO2016026196A1
WO2016026196A1 PCT/CN2014/087624 CN2014087624W WO2016026196A1 WO 2016026196 A1 WO2016026196 A1 WO 2016026196A1 CN 2014087624 W CN2014087624 W CN 2014087624W WO 2016026196 A1 WO2016026196 A1 WO 2016026196A1
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reaction
carboxylic acid
ammonium salt
quaternary ammonium
acid
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French (fr)
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荆丰伟
金瑞
刘建文
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江苏万淇生物科技有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids

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  • the invention relates to the technical field of surfactants, in particular to a novel double long-chain ester-based "Gemini" quaternary ammonium salt and a synthetic process thereof.
  • Soft, antistatic agent mainly used in textile printing and dyeing industry, such softener has excellent softness, antistatic, sterilization and anti-yellowing properties.
  • the dosage is small, the effect is good, the preparation is convenient, the compatibility is good, and the cost is high.
  • Flocculant, demulsifier widely used in the water treatment industry as a quaternary ammonium salt for inorganic flocculant synergists.
  • Drilling fluid, VES fracturing fluid, drag reducing agent, thickener Gemini viscoelastic surfactant is mainly used in the petrochemical industry and is a new research and development trend.
  • the present invention adopts the following technical scheme: a novel double long-chain ester-based "Gemini" quaternary ammonium salt and a synthetic process thereof, which are compounds having the structure shown below:
  • the long carbon chain alcohol in the step 1 may be stearyl alcohol, palmitol, lauryl alcohol, myristyl alcohol or oleyl alcohol.
  • halocarboxylic acid or haloacetyl halide in the step 1 may be chloroacetic acid, bromoacetic acid or chloroformyl chloride.
  • the solvent in the step 2 is one or more of a ketone such as acetone, methyl ethyl ketone or an alcohol such as methanol or ethanol.
  • a ketone such as acetone, methyl ethyl ketone or an alcohol such as methanol or ethanol.
  • the invention has the following beneficial effects: the diester group introduced in the double long chain ester group "Gemini" quaternary ammonium salt structure, the biodegradability of the molecule is greatly enhanced, and meets the requirements of future surfactant chemical friendly performance;
  • the raw materials used halogenated carboxylic acid, tetramethyldiamine, long-chain alcohol, are available in sufficient quantities to meet the requirements of industrial raw materials;
  • the alkylating agent of the present invention is an alpha halocarboxylate, and its high reactivity makes the high yield of the second quaternization reaction and the simple post-treatment process a reality, and avoids the use of dimethyl sulfate.
  • Example 1 9.4 g (0.1 mol) of chloroacetic acid and 27 g (0.1 mol) of stearyl alcohol were weighed, added to a 100 mL three-necked flask, and heated to 60 ° C in an oil bath to completely melt the solid reactant, and then weighed 172 mg ( 1 mmol) of p-toluenesulfonic acid was added to the above reaction system, and the reaction temperature was raised to 120 ° C, and the reaction was continued for 3 hours, and the heating was stopped.
  • Example 2 13.8 g (0.1 mol) of bromoacetic acid and 27 g (0.1 mol) of stearyl alcohol were weighed, added to a 100 mL three-necked flask, and heated to 60 ° C in an oil bath to completely melt the solid reactant, and then weighed 172 mg ( 1 mmol) of p-toluenesulfonic acid was added to the above reaction system, and the reaction temperature was raised to 120 ° C, and the reaction was continued for 3 hours, and the heating was stopped.
  • Example 3 11.2 g (0.1 mol) of chloroacetyl chloride and 24.2 g (0.1 mol) of palmitol were weighed into 100 mL of ethyl acetate, and added to a 250 mL three-necked flask, and NaHCO 3 (16.8 g, 0.2 mol) was added.
  • the reaction liquid was washed twice with water (100 mL), dried over anhydrous sodium sulfate, and evaporated to ethyl ether ethyl acetate to give 31.1 g of chlorocarboxylic acid cetyl ester, light yellow sticky. Heavy oil with 98% yield.
  • the viscous material was dissolved in 60 mL of ethanol, and 5.7 g (0.05 mol) of tetramethylethylenediamine was added to the above solution, and the temperature was raised to 80 ° C. The reaction was refluxed for 8 hours, and the heating was stopped to obtain the product octadecyl ester group. The Gemini quaternary ammonium salt precipitates as a white solid. Filtration and washing with iced ethanol gave a white solid powder 37.2 g, yield 94%, and the reaction mother liquid was recovered and reused.
  • Example 4 9.4 g (0.1 mol) of chloroacetic acid and 27 g (0.1 mol) of stearyl alcohol were weighed, added to a 100 mL three-necked flask, and heated to 60 ° C in an oil bath to completely melt the solid reactant, and then weighed 172 mg ( 1 mmol) of p-toluenesulfonic acid was added to the above reaction system, and the reaction temperature was raised to 120 ° C, and the reaction was continued for 3 hours, and the heating was stopped.
  • Example 5 9.4 g (0.1 mol) of chloroacetic acid and 20.1 g (0.1 mol) of lauryl alcohol were weighed, added to a 100 mL three-necked flask, and heated to 60 ° C in an oil bath to completely melt the solid reactant, and then weighed 172 mg ( 1 mmol) p-toluenesulfonic acid added to the above reaction body In the system, the reaction temperature was raised to 120 ° C, and the reaction was continued for 3 hours, and the heating was stopped.
  • Example 6 13.8 g (0.1 mol) of bromoacetic acid and 22.9 g (0.1 mol) of myristyl alcohol were weighed, added to a 100 mL three-necked flask, heated to 60 ° C in an oil bath, and the solid reactant was completely melted, and then 172 mg was weighed. (1 mmol) p-toluenesulfonic acid was added to the above reaction system, the reaction temperature was raised to 120 ° C, and the reaction was carried out for 3 hours, and the heating was stopped.
  • Example 8 Weigh 9.4 g (0.1 mol) of chloroacetic acid and 26.9 g (0.1 mol) Oleic alcohol was added to a 100 mL three-necked flask, and the oil bath was heated to 60 ° C to completely melt the solid reactant. Then, 172 mg (1 mmol) of p-toluenesulfonic acid was added to the above reaction system, and the reaction temperature was raised to 120 ° C. The reaction was stopped for 3 hours.

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

Abstract

本发明公开了一种新型双长链酯基季铵盐及其合成工艺。其合成步骤如下：卤代羧酸的酯化反应：将卤代羧酸或卤代乙酰卤和长碳链醇按一定比例混合，在无溶剂条件下，反应得到α卤代羧酸酯；卤代羧酸酯与四甲基二胺的季胺化反应：将上述得到的所述卤代羧酸酯反应中间体与四甲基二胺以一定比例混合，加入适量溶剂，在一定条件下反应得到谈黄色透明液体，冷却析出白色固体物质，经过滤真空干燥得到新型双长链酯基"双子座"季铵盐成品。本发明具有以下有益效果：本发明制得的季铵盐生物降解性强、亲水性强；本发明的烷基化试剂α卤代羧酸酯能使季铵化反应高产、后处理工艺简洁，绿色环保；本发明第一步酯化反应可在无溶剂条件下进行，减少了三废排放。

Description

一种新型双长链酯基季铵盐及其合成工艺 技术领域
本发明涉及表面活性剂技术领域，具体涉及一种新型双长链酯基“双子座”季铵盐及其合成工艺。
背景技术
四级铵盐又称季铵盐，英文名quaternary-N。为铵离子中的四个氢原子都被烃基取代而生成的化合物，通式R4NX，其中四个烃基R可以相同，也可不同。X多是卤素负离子(F、Cl、Br、I)，也可是酸根(如HSO4、RCOO等)。得益于季铵盐独特的结构特征其在多个方面有广泛的用途。
杀菌、消毒剂：包括：农业杀菌剂、公共场所杀菌消毒、循环水杀菌灭藻剂、水产养殖杀菌消毒剂、医疗杀菌消毒剂、畜禽舍消毒剂、赤潮杀灭剂、蓝藻杀灭剂等杀菌消毒领域。特别是Gemini季铵盐杀菌效果突出，综合成本低。
柔软、抗静电剂：主要用于纺织印染行业，此类柔软剂且有优异的柔软、抗静电、杀菌、抗黄变性能。用量少，效果好，配制方便，配伍性好，具有极高的性价比。
絮凝剂、破乳剂：广泛用于水处理行业，作为一种无机絮凝剂增效剂用的季铵盐。
钻井液、VES压裂液、减阻剂、增稠剂：Gemini粘弹性表面活性剂主要用于石油化工行业，是一种新型的研究开发趋势。
阴离子增效剂：超支化Gemini季铵盐打破了传统阴离子不能与阳离子兼容的理论学说。这类产品不但能与阴离子兼溶，并且还具有协同增效的作用，广泛用于阴离子增效剂。
双长链酯基“双子座”季铵盐是酯基季铵盐中性能较为优异的一种，目前正处于开发阶段，得益于“双子座”季铵盐的突出效果，其应用前景广阔。但是传统的双长链酯基“双子座”季铵盐的合成工艺过程中季铵化反应过程条件苛刻，产物分离提纯困难，产率较低，不适用工业化大生产。特别是其工艺过程中还涉及使用到硫酸二甲酯，卤甲烷等大毒性烷基化试剂会给产品和环境带来较大的风险。
发明内容
本发明的目的是提供一种不含APEO、甲醛；易生物降解；绿色环保；用量少；效果好；配制方便；综合成本低；具有极高的性价比的新型双长链酯基“双子座”季铵盐及其合成工艺。
为了解决背景技术所存在的问题，本发明是采用以下技术方案：一种新型双长链酯基“双子座”季铵盐及其合成工艺，其为具有如下所示结构的化合物：
Figure PCTCN2014087624-appb-000001
式中n＝0、1、2或4；m＝12、14、16或18；X-为Cl-、Br-或I-。
其合成步骤如下：
1、卤代羧酸的酯化反应：将卤代羧酸或卤代乙酰卤和相应的长碳链的醇以摩尔比为1∶1～1∶1.2的比例混合，在无溶剂或所述长 链醇本身即作反应物又作为溶剂，反应温度为100～180℃条件下，加催化剂进行反应，反应时间为2h～8h，得到无色透明液体α卤代羧酸酯，反应方程式如下：
Figure PCTCN2014087624-appb-000002
2、卤代羧酸酯与四甲基二胺的季胺化反应：将上述得到的所述卤代羧酸酯反应中间体与四甲基二胺以摩尔比为2∶1～2.5∶1的比例混合，向反应体系中加入适量溶剂，在反应温度为20～100℃反应条件下反应5h～24h，得到谈黄色透明液体，冷却析出白色固体物质，经过滤真空干燥得到白色固体产物，即新型双长链酯基“双子座”季铵盐成品，其反应方程式如下：
Figure PCTCN2014087624-appb-000003
进一步地，所述步骤1中反应催化剂为对甲苯磺酸、甲磺酸，三氟甲磺酸，氨基磺酸、三氟甲磺酸稀土盐(RE(OTf)3)中的一种或几种。
进一步地，所述步骤1中的长碳链的醇可以为硬脂醇、棕榈醇、月桂醇、肉豆蔻醇、油醇。
进一步地，所述步骤1中的卤代羧酸或卤代乙酰卤可以为氯乙酸、溴乙酸、氯代酰氯。
进一步地，所述步骤2中的溶剂为酮类，例如丙酮、甲乙酮或醇类例如甲醇、乙醇，中的一种或几种。
本发明具有以下有益效果：双长链酯基“双子座”季铵盐结构中引入的双酯基，使得该分子的生物降解性大大增强，符合未来表面活性剂化学友好性能要求；同时，本发明所用的原料卤代羧酸、四甲基二胺、长链醇都有充足的供应，符合工业化原材料需求；另 外，本发明的烷基化试剂为α卤代羧酸酯，其较高的反应活性使得第二步季铵化反应的高产率和简洁的后处理工艺成为现实，也避免了使用硫酸二甲酯，卤甲烷等大毒性烷基化试剂；再者，本发明第一步酯化反应可在无溶剂条件下进行，减少了三废排放；最后，本发明所述的结构具有较强亲水性，有助于其在水中的溶解及分散，有助于提高其应用效果。
具体实施方式
下面对本发明做进一步详细的说明。
实施例1：称取9.4g(0.1mol)氯乙酸和27g(0.1mol)硬脂醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取5.8g(0.05mol)四甲基乙二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体粉末36.7g，产率91％，反应母液可回收重复使用。
实施例2：称取13.8g(0.1mol)溴乙酸和27g(0.1mol)硬脂醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取5.8g(0.05mol)四甲基乙二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体 粉末41.6g，产率92％，反应母液可回收重复使用。
实施例3：称取11.2g(0.1mol)氯乙酰氯和24.2g(0.1mol)棕榈醇融入到100mL乙酸乙酯中，加入到250mL三口烧瓶中，NaHCO3(16.8g，0.2mol)加入到上述反应体系中，常温反应3h后，反应液用水(100mL)洗两次，无水硫酸钠干燥，减压蒸去溶剂乙酸乙酯即得氯代羧酸十六醇酯31.1g，淡黄色粘稠油状物，产率98％。将该粘稠物溶于60mL乙醇中，称取5.7g(0.05mol)四甲基乙二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体粉末37.2g，产率94％，反应母液可回收重复使用。
实施例4：称取9.4g(0.1mol)氯乙酸和27g(0.1mol)硬脂醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取6.5g(0.05mol)四甲基丙二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体粉末38.2g，产率93％，反应母液可回收重复使用。
实施例5：称取9.4g(0.1mol)氯乙酸和20.1g(0.1mol)月桂醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体 系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取6.5g(0.05mol)四甲基丙二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体粉末29.6g，产率91％，反应母液可回收重复使用。
实施例6：称取13.8g(0.1mol)溴乙酸和22.9g(0.1mol)肉豆蔻醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取7.2g(0.05mol)四甲基丁二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体粉末37.3g，产率92％，反应母液可回收重复使用。
实施例7：称取13.8g(0.1mol)溴乙酸和24.2g(0.1mol)棕榈醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取8.6g(0.05mol)四甲基己二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得白色固体粉末4.1.8g，产率94％，反应母液可回收重复使用。
实施例8：称取9.4g(0.1mol)氯乙酸和26.9g(0.1mol) 油醇，加入到100mL三口烧瓶中，油浴加热到60℃，使固体反应物完全熔化后，称取172mg(1mmol)对甲苯磺酸加入到上述反应体系中，升高反应温度为120℃，反应3h，停止加热。30mL乙醇加入到上述反应液中，称取7.2g(0.05mol)四甲基丁二胺加入上述溶液中，升温至80℃，回流反应8小时，停止加热，产物双十八碳酯基双子座季铵盐以白色固体形式析出。过滤，冰乙醇洗涤得奶白色粘稠固体37.0g，产率89％，反应母液可回收重复使用。
最后说明的是，以上实施例仅用以说明本发明的技术方案而非限制，本领域普通技术人员对本发明的技术方案所做的其他修改或者等同替换，只要不脱离本发明技术方案的精神和范围，均应涵盖在本发明的权利要求范围当中。

Claims (6)

  1. 一种新型双长链酯基季铵盐，其特征在于，其为具有如下所示结构的化合物：
    Figure PCTCN2014087624-appb-100001
    式中n＝0、1、2或4；m＝12、14、16或18；X-为Cl-、Br-或I-。
  2. 根据权利要求1所述的一种新型双长链酯基季铵盐的合成工艺，其特征在于，其合成步骤如下：
    (1)卤代羧酸的酯化反应：将卤代羧酸或卤代乙酰卤和相应的长碳链的醇以摩尔比为1∶1～1∶1.2的比例混合，在无溶剂或所述长链醇本身即作反应物又作为溶剂，反应温度为100～180℃条件下，加催化剂进行反应，反应时间为2h～8h，得到无色透明液体α卤代羧酸酯；
    (2)卤代羧酸酯与四甲基二胺的季胺化反应：将上述得到的所述卤代羧酸酯反应中间体与四甲基二胺以摩尔比为2～2.5∶1的比例混合，向反应体系中加入适量溶剂，在反应温度为20～100℃反应条件下反应5h～24h，得到淡黄色透明液体，冷却析出白色固体物质，经过滤真空干燥得到白色固体产物，即新型双长链酯基“双子座”季铵盐成品。
  3. 根据权利要求2所述的一种新型双长链酯基季铵盐的合成工艺，其特征在于，所述步骤(1)中反应催化剂至少为对甲苯磺酸、甲磺酸，三氟甲磺酸，氨基磺酸、三氟甲磺酸稀土盐(RE(OTf)3)中的一种。
  4. 根据权利要求2所述的一种新型双长链酯基季铵盐的合成工艺，，其特征在于，所述步骤(1)中的长碳链的醇为硬脂醇、棕榈醇、月桂醇、肉豆蔻醇或油醇。
  5. 根据权利要求2所述的一种新型双长链酯基季铵盐的合成工艺，其特征在于，所述步骤(1)中的卤代羧酸或卤代乙酰卤可以为氯乙酸、溴乙酸或氯代酰氯。
  6. 根据权利要求2所述的一种新型双长链酯基季铵盐的合成工艺，其特征在于，所述步骤(2)中的溶剂至少为丙酮、甲乙酮、甲醇、乙醇中的一种。
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