CN104557708B - 一种一浴合成阳离子漂白活化剂的方法及应用 - Google Patents

一种一浴合成阳离子漂白活化剂的方法及应用 Download PDF

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CN104557708B
CN104557708B CN201510051139.3A CN201510051139A CN104557708B CN 104557708 B CN104557708 B CN 104557708B CN 201510051139 A CN201510051139 A CN 201510051139A CN 104557708 B CN104557708 B CN 104557708B
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caprolactam
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benzoic acid
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崔双双
马维
丁婕
林兴焕
郭筱璐
许长海
杜金梅
孙昌
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QINGDAO FRONTIERCHEM Co.,Ltd.
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Abstract

本发明公开了一种一浴合成阳离子漂白活化剂TBLC的方法及应用，属于精细化工技术领域。本发明所提供的方法是将4‑氯甲基苯甲酰氯和己内酰胺溶于溶剂中，再缚酸剂加入到己内酰胺溶液中溶解，再将4‑氯甲基苯甲酰氯溶液逐滴加入到己内酰胺‑缚酸剂溶液中搅拌混合，最后加入叔胺进行反应，反应结束后旋干溶剂，洗涤所得固体后获得目标产物。本发明所提供的方法大幅度简化了阳离子漂白活化剂TBLC的合成工艺，降低了合成阳离子漂白活化剂TBLC所需条件，同时保证了较高的产率，适于产业化推广。

Description

一种一浴合成阳离子漂白活化剂的方法及应用
技术领域
本发明涉及一种一浴合成阳离子漂白活化剂的方法及应用，属于精细化工技术领域。
背景技术
过氧化氢因其绿色，无污染是一种工业上广泛应用的漂白剂。低温活化漂白是近些年来新出现的一种漂白方法，该漂白方式较传统过氧化氢漂白有着明显的优势。低温活化漂白体系中，过氧化氢的作用环境为近中性(传统漂白方式，pH 11-12，加入氢氧化钠或者碳酸钠)，常温(漂洗)或中等温度(传统漂白方式，近100℃)，减少了能量的消耗，减轻了工厂废水处理的负担；另外，减少了对待漂基质(如：棉织物)的损伤。
漂白活化剂在低温活化漂白体系中起着至关重要的作用，其作为有机过氧酸前驱体，可与过氧化氢在水溶液中发生反应，生成比过氧化氢更活泼的过氧酸，可以在更低的温度下，有效的去除有色杂质。常用的漂白活化剂为壬酰氧基苯磺酸钠(NOBS)，四乙酰乙二胺(TAED)，N-4(三乙基铵甲撑苯酰基)内酰胺(TBLC)。NOBS和TAED分别因其在pH较低(接近中性)的情况下易发生副反应，水溶性较低的原因，应用受到很大的限制。TBLC最佳作用pH为7.2，具有优良的水溶性，没有两者的缺点，并且其结构中带有季铵盐阳离子基团，使其在水溶液中能够对表面带负电的材料表面有一定的亲和力，进而更好的进行漂白过程。目前限制TBLC大规模工业化应用的主要原因是合成步骤繁琐，价格昂贵。目前有很多研究者对TBLC的研究多偏重于对其结构的改变以获得不同的应用特性，或者研究与其相关的漂白工艺体系，例如：改变TBLC离去基团内酰胺环中碳的个数，提高其水解稳定性；改变TBLC季铵盐阳离子基团的结构，合成具有不同结构或具有双阳离子结构的活化剂，探究其应用性能；研究N-4(三乙基铵甲撑苯酰基)内酰胺(TBCC)/H2O2/NaHCO3漂白体系，发现其在60℃下的漂白效果同H2O2/NaHCO3漂白体系在90℃下的漂白效果相近，且能够很好的改变棉织物的吸湿性。目前，很少有研究者探究如何简化TBLC类阳离子漂白活化剂的合成步骤，降低其成本使其应用更加广泛。
发明内容
为解决简化TBLC类阳离子漂白活化剂合成过程过于复杂的问题，本发明提供了一种一浴合成TBLC类阳离子漂白活化剂的方法，所采取的技术方案如下：
本发明的目的在于提供一种一浴合成TBLC类阳离子漂白活化剂的方法，该方法的步骤如下：
1)利用溶剂分别溶解4-氯甲基苯甲酰氯和己内酰胺，再缚酸剂溶解到己内酰胺溶液中，获得4-氯甲基苯甲酰氯溶液和己内酰胺-缚酸剂溶液；
2)将步骤1)所得的4-氯甲基苯甲酰氯溶液逐滴加入到己内酰胺-缚酸剂溶液中，常温下搅拌混合，获得己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液；
3)将叔胺加入到步骤2)所得的己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液中回流搅拌处理，获得反应溶液；
4)过滤并蒸干步骤3)所得反应溶液，洗涤所得固体后获得目标产物。
优选地，所述叔胺、4-氯甲基苯甲酰氯和己内酰胺，摩尔比为叔胺：4-氯甲基苯甲酰氯：己内酰胺＝1:1:1。
优选地，步骤1)所述溶剂，是甲苯、四氢呋喃、乙酸乙酯、乙腈、乙醇或甲醇；所述缚酸剂，是碳酸钠、碳酸钾、氢氧化钠、氢氧化钾、三乙胺或N-甲基吗啡啉中的一种或几种混合；缚酸剂与4-氯甲基苯甲酰氯的摩尔比为2～1:1。
优选地，步骤2)所述常温下搅拌混合，搅拌时间为3h。
优选地，步骤3)所述回流搅拌，搅拌时间为4h。
优选地，步骤4)所述洗涤，所用溶剂是丙酮；所述目标产物，其结构是如下：
式中，n为1，2，3，4或5；烷基R1，R2，R3的碳原子数为1，2，4，6，8，10，12，14或16。
优选地，所述方法的具体步骤如下：
1)以乙腈为溶剂，按照摩尔比为4-氯甲基苯甲酰氯：己内酰胺＝1:1:1的比例分别溶解4-氯甲基苯甲酰氯和己内酰胺，再将缚酸剂三乙胺溶解到己内酰胺溶液中，获得4-氯甲基苯甲酰氯溶液和己内酰胺-缚酸剂溶液；
所述缚酸剂按照摩尔比缚酸剂：4-氯甲基苯甲酰氯＝2～1:1的量添加；
2)将步骤1)所得的4-氯甲基苯甲酰氯溶液逐滴加入到己内酰胺-缚酸剂溶液中，在于常温下搅拌混合3h，获得己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液；
3)再按摩尔比为叔胺：4-氯甲基苯甲酰氯：己内酰胺＝1:1:1的比例将叔胺加入到步骤2)所得的己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液中回流搅拌处理4h，获得反应溶液；
4)过滤并蒸干步骤3)所得反应溶液，利用丙酮洗涤所得固体后获得目的产物；
所述目标产物，其结构是如下：
式中，n为1，2，3，4或5；烷基R1，R2，R3的碳原子数为1，2，4，6，8，10，12，14或16，可调整阳离子型漂白活化剂的亲水亲油平衡值。。
所述方法用于制备阳离子漂白活化剂，优选制备TBLC类阳离子漂白活化剂。
本发明获得的有益效果如下：
现有技术在合成阳离子漂白活化剂TBLC时，往往会经过多浴反应才能获得最终产物，合成工艺十分复杂，合成条件苛刻。本发明通过一浴法合成阳离子漂白活化剂TBLC，大幅度简化了阳离子漂白活化剂TBLC的合成工艺，降低了合成阳离子漂白活化剂TBLC所需条件，同时保证了较高的产率，并且有效的降低了该产品的生产成本。以TBCC为例，一浴法的产率可以由传统两步法的58％提高到94.7％，生产成本却可以由传统两步法的1066.01元降低至598.20元。
具体实施方式
下面结合具体实施例对本发明做进一步说明，但本发明不受实施例的限制。
以下实施例所用材料、试剂、仪器和方法，未经特殊说明，均为本领域常规材料、试剂、仪器和方法，均可通过商业渠道获得。
实施例1
将己内酰胺(2.26g,0.02mol)溶于20ml乙腈中之后加入碳酸钠(4.20g,0.04mol)。4-氯甲基苯甲酰氯(0.02mol,3.86g)溶于20ml溶剂中，将其逐滴加入己内酰胺溶液中，常温搅拌3h。之后加入三乙胺(2.02g,0.02mol)，回流搅拌4h。
过滤之后蒸干滤液。所得固体中加入20ml丙酮，加热搅拌，过滤得到白色固体。干燥后称重为6.45克，产率为88％。核磁共振和和质谱测试数据如下：
1H-NMR(400MHz,CDCl3)δ7.72-7.54(m,4H),4.97(s,2H),4.02–3.95(m,2H),3.52–3.41(m,6H),3.21–3.07(m,6H),2.71–2.68(m,2H),1.99–1.93(m,6H),1.47–1.39(m,18H).计算得C20H31N2O2[M-Cl]+331.2，测的相对分子质量为331.2。
实施例2
将己内酰胺(2.26g,0.02mol)溶于20ml乙腈中之后加入三乙胺(2.02g,0.02mol)。4-氯甲基苯甲酰氯(0.02mol,3.86g)溶于20ml溶剂中，将其逐滴加入到己内酰胺溶液中，常温搅拌3h。之后加入三乙胺(2.02g,0.02mol)，回流搅拌4h。
过滤之后蒸干滤液。所得固体中加入20ml丙酮，加热搅拌，过滤得到白色固体。干燥后称重为6.81克，产率为93％。
实施例3
将己内酰胺(2.26g,0.02mol)溶于20ml乙腈中之后加入碳酸钠(2.02g,0.02mol)。4-氯甲基苯甲酰氯(0.02mol,3.86g)溶于20ml溶剂中，将其逐滴加入到己内酰胺溶液中，常温搅拌3h。之后加入二甲基乙胺(1.46g,0.02mol)，回流搅拌4h。
过滤之后蒸干滤液。所得固体中加入20ml丙酮，加热搅拌，过滤得到白色固体。干燥后称重为5.56克，产率为91.7％。核磁共振和和质谱测试数据如下：
1H NMR(400MHz,CDCl3):δ7.74(d,J＝8.1Hz,2H),7.52(d,J＝8.1Hz,2H),5.08(s,2H),3.96(s,2H),3.62(q,J＝7.2Hz,2H),3.18(s,6H),2.66(d,J＝6.4Hz,2H),1.82(s,6H),1.39(t,J＝7.2Hz,3H)；13C NMR(100MHz,CDCl3):δ177.6,172.8,138.5,133.0,130.2,127.7,65.9,59.2,48.8,44.8,38.6,29.2,28.9,23.5,8.4；MS-ESI(m/z):[M]+calculatedfor C18H27N2O2303.2,found:303.1.
实施例4
将己内酰胺(2.26g,0.02mol)溶于20ml乙腈中之后加入碳酸钠(2.02g,0.02mol)。4-氯甲基苯甲酰氯(0.02mol,3.86g)溶于20ml溶剂中，将其逐滴加入到己内酰胺溶液中，常温搅拌3h。之后加入N,N-二甲基丁胺(2.02g,0.02mol)，回流搅拌4h。
过滤之后蒸干滤液。所得固体中加入20ml丙酮，加热搅拌，过滤得到白色固体。干燥后称重为5.43克，产率为82.0％。核磁共振和和质谱测试数据如下：
1H NMR(400MHz,CDCl3):δ7.72(d,J＝8.1Hz,2H),7.52(d,J＝8.1Hz,2H),5.07(s,2H),3.96(s,2H),3.54-3.38(m,2H),3.21(s,6H),2.66(d,J＝6.3Hz,2H),1.82(s,6H),1.75(s,2H),1.36(dd,J＝14.8,7.4Hz,2H),0.94(t,J＝7.3Hz,3H)；13C NMR(100MHz,CDCl3):δ177.8,173.0,138.7,133.2,130.3,127.9,66.6,63.5,49.6,45.0,38.7,29.4,29.0,24.5,23.6,19.6,13.7；MS-ESI(m/z):[M]+calculated for C20H31N2O2:331.2,found:331.1.
实施例5
将己内酰胺(2.26g,0.02mol)溶于20ml乙腈中之后加入碳酸钠(2.02g,0.02mol)。4-氯甲基苯甲酰氯(0.02mol,3.86g)溶于20ml溶剂中，将其逐滴加入到己内酰胺溶液中，常温搅拌3h。之后加入N,N-二甲基己胺(2.02g,0.02mol)，回流搅拌4h。
过滤之后蒸干滤液。所得固体中加入20ml丙酮，加热搅拌，过滤得到白色固体。干燥后称重为6.39克，产率为89.0％。核磁共振和和质谱测试数据如下：
1H NMR(400MHz,CDCl3):δ7.73(d,J＝8.1Hz,2H),7.52(d,J＝8.1Hz,2H),5.12(s,2H),3.95(s,2H),3.5-3.33(m,2H),3.23(s,6H),2.66(d,J＝6.4Hz,2H),1.82(s,6H),1.75(s,2H),1.27(d,J＝10.0Hz,6H),0.84(t,J＝6.8Hz,3H)；13C NMR(100MHz,CDCl3):δ177.7,172.9,138.9,133.2,130.2,127.9,66.5,63.8,49.6,45.0,38.8,31.3,29.4,29.1,25.9,23.7,22.8,22.3,13.9；MS-ESI(m/z):[M]+calculated for C22H35N2O2:359.3,found:359.1.
虽然本发明已以较佳的实施例公开如上，但其并非用以限定本发明，任何熟悉此技术的人，在不脱离本发明的精神和范围内，都可以做各种改动和修饰，因此本发明的保护范围应该以权利要求书所界定的为准。

Claims (8)

1.一种一浴合成阳离子漂白活化剂的方法，其特征在于，步骤如下：
1)利用溶剂分别溶解4-氯甲基苯甲酰氯和己内酰胺，再将缚酸剂溶解到己内酰胺溶液中，获得4-氯甲基苯甲酰氯溶液和己内酰胺-缚酸剂溶液；
2)将步骤1)所得的4-氯甲基苯甲酰氯溶液逐滴加入到己内酰胺-缚酸剂溶液中，常温下搅拌混合，获得己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液；
3)将叔胺加入到步骤2)所得的己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液中回流搅拌处理，获得反应溶液；
4)过滤并蒸干步骤3)所得反应溶液，洗涤所得固体后获得目标产物；
所述目标产物，其结构是如下：
式中，n为2；烷基R1，R2，R3的碳原子数为1，2，4，6，8，10，12，14或16。
2.权利要求1所述方法，其特征在于，所述叔胺、4-氯甲基苯甲酰氯和己内酰胺，摩尔比为叔胺：4-氯甲基苯甲酰氯：己内酰胺＝1:1:1。
3.权利要求1所述方法，其特征在于，步骤1)所述溶剂，是甲苯、四氢呋喃、乙酸乙酯、乙腈、乙醇或甲醇。
4.权利要求1所述方法，其特征在于，步骤1)所述缚酸剂，是碳酸钠、碳酸钾、氢氧化钠、氢氧化钾、三乙胺或N-甲基吗啡啉中的一种或几种混合；缚酸剂与4-氯甲基苯甲酰氯的摩尔比为2～1:1。
5.权利要求1所述方法，其特征在于，步骤2)所述常温下搅拌混合，搅拌时间为3h。
6.权利要求1所述方法，其特征在于，步骤3)所述回流搅拌，搅拌时间为4h。
7.权利要求1所述方法，其特征在于，步骤4)所述洗涤，所用溶剂是丙酮；所述目标产物，其结构是如下：
式中，n为2；烷基R1，R2，R3的碳原子数为1，2，4，6，8，10，12，14或16。
8.权利要求1所述方法，其特征在于，具体步骤如下：
1)以乙腈为溶剂，按照摩尔比为4-氯甲基苯甲酰氯：己内酰胺＝1:1的比例分别溶解4-氯甲基苯甲酰氯和己内酰胺，再将缚酸剂三乙胺溶解到己内酰胺溶液中，获得4-氯甲基苯甲酰氯溶液和己内酰胺-缚酸剂溶液；
所述缚酸剂按照摩尔比缚酸剂：4-氯甲基苯甲酰氯＝2～1:1来添加；
2)将步骤1)所得的4-氯甲基苯甲酰氯溶液逐滴加入到己内酰胺-缚酸剂溶液中，在于常温下搅拌混合3h，获得己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液；
3)再按摩尔比为叔胺：4-氯甲基苯甲酰氯：己内酰胺＝1:1:1的比例将叔胺加入到步骤2)所得的己内酰胺-缚酸剂-4-氯甲基苯甲酰氯溶液中回流搅拌处理4h，获得反应溶液；
4)过滤并蒸干步骤3)所得反应溶液，利用丙酮洗涤所得固体后获得目的产物；
所述目标产物，其结构是如下：
式中，n为2；烷基R1，R2，R3的碳原子数为1，2，4，6，8，10，12，14或16。
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