CN106565645B - 薄荷甲酸葫芦巴酯的制备方法及其应用 - Google Patents
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Abstract
本发明提供一种薄荷甲酸葫芦巴酯的制备方法，反应器中加入薄荷甲酸、二甲苯及葫芦巴内酯，在催化剂浓硫酸作用下反应生成薄荷甲酸葫芦巴酯。本发明所制备的薄荷甲酸葫芦巴酯应用在烟草加香中，将薄荷甲酸葫芦巴酯以1000倍的乙醇溶解形成薄荷甲酸葫芦巴酯溶液，薄荷甲酸葫芦巴酯溶液与烟丝按照0.01～1：100的质量比添加到烟丝中。本发明所提供的薄荷甲酸葫芦巴酯具有反应条件温和、安全，步骤简单，易于工业化生产等优点；应用于烟草中，在卷烟抽吸时能够明显的赋予烟气葫芦巴内酯甘蔗糖蜜样的、略带焦香果味的特征香气、还能起到柔和烟气并增加烟气浓度的作用，同时不会增加卷烟生产的成本，因此在烟草行业有着广泛的应用前景。
Description
技术领域
本发明涉及烟草增香技术领域，具体涉及一种薄荷甲酸葫芦巴酯的制备方法及其应用。
背景技术
中式低焦卷烟的发展，必须加强对中式卷烟特色香料物质基础的研究，通过烟草特有香味成分及潜香物质的合成、纯化技术，加大新香料的开发力度，丰富烟用香精原料品种，在中式卷烟焦油等降低的同时，进行香味补偿，满足消费者新的对卷烟吸味更高的要求。
葫芦巴内酯(又名3-羟基-4,5-二甲基-2(5H)呋喃酮)应用于卷烟加香中，能够增加烟草的甜香，改善抽吸口感的作用，是一种较常用的优良烟草添加剂，但应用过程中由于葫芦巴内酯本身参与燃烧裂解，其本身的甘蔗糖蜜样的、略带焦香果味的优雅香气被破坏而无法体现，加大用量又会带来烟气粗糙、口腔刺激增加等副作用。
发明内容
针对现有技术的不足，本发明提供一种薄荷甲酸葫芦巴酯的制备方法及其应用，在卷烟抽吸是能赋予卷烟葫芦巴内酯甘蔗糖蜜样的、略带焦香果味的特征香气、同时能起到柔和烟气并增加烟气浓度的作用。
本发明解决上述技术问题所采用的技术方案是：提供一种薄荷甲酸葫芦巴酯的制备方法，所述制备方法如下：
在反应器中加入薄荷甲酸、二甲苯及葫芦巴内酯，在催化剂浓硫酸作用下反应，其化学反应式如下：
进一步的，其制备方法为：
(1)在装有搅拌器、分水器、回流冷凝管、温度计的混合容器中加入薄荷甲酸、葫芦巴内酯和二甲苯；薄荷甲酸与葫芦巴内酯和二甲苯的摩尔比分别为1︰0.7～3，1:5～20；
(2)缓慢搅拌，慢慢滴加浓硫酸，薄荷甲酸与浓硫酸的摩尔比为1:0.04～0.2，缓慢加热至回流，反应2～7h；
(3)待反应液冷却后，常压蒸馏，回收过剩的二甲苯和葫芦巴内酯；
(4)冷却后将反应物移到分液漏斗中，先用二甲苯体积分数5～15倍的水洗涤，用碳酸氢钠中和成碱性，再用二甲苯体积分数5～15倍的水洗涤，得到的粗产物用薄荷甲酸摩尔质量0.2～0.8倍的无水碳酸镁干燥；
(5)用硅胶柱层析进一步纯化，洗脱剂为为二氯甲烷：甲醇按照2～10:1体积比配比而成，即得到薄荷甲酸葫芦巴酯。
本发明所制备的薄荷甲酸葫芦巴酯应用在烟草加香中，其特征在于：将薄荷甲酸葫芦巴酯以1000倍的乙醇溶解形成薄荷甲酸葫芦巴酯溶液，薄荷甲酸葫芦巴酯溶液与烟丝按照0.01～1：100的质量比添加到烟丝中。
本发明所提供的薄荷甲酸葫芦巴酯具有反应条件温和、安全，步骤简单，易于工业化生产等优点；应用于烟草中，在卷烟抽吸时能够明显的赋予烟气葫芦巴内酯甘蔗糖蜜样的、略带焦香果味的特征香气、还能起到柔和烟气并增加烟气浓度的作用，同时不会增加卷烟生产的成本，因此在烟草行业有着广泛的应用前景。
具体实施方式
下面将结合具体实施例，对本发明中的技术方案进行清楚、完整地描述。
实施例1：在装有搅拌器、分水器、回流冷凝管、温度计的三口烧瓶中，加入薄荷甲酸1.86g(0.010mol)，葫芦巴内酯1.92g(0.015mol)，加入10ml二甲苯，缓慢搅拌，慢慢滴加0.098g(0.001mol)浓硫酸，缓慢加热至回流，反应6h。待反应液冷却后，常压蒸馏，回收过剩的二甲苯和葫芦巴内酯。冷却后将反应物移到分液漏斗中，先用50ml水洗涤，用碳酸氢钠中和成碱性，再用50ml水洗涤，分离出的粗产物用0.5g无水碳酸镁干燥。进行减压蒸馏，用柱层析进一步实现纯化，洗脱剂为v(二氯甲烷：甲醇)＝5:1，得2.06g目标产物。将薄荷甲酸葫芦巴酯以1000倍的95％乙醇溶解，再将薄荷甲酸葫芦巴酯溶液与烟丝按照0.01：100的质量比均匀喷洒在烟丝中。
实施例2：在装有搅拌器、分水器、回流冷凝管、温度计的三口烧瓶中，加入薄荷甲酸3.72g(0.020mol)，葫芦巴内酯2.56g(0.020mol)，加入15ml二甲苯，缓慢搅拌，慢慢滴加0.28g(0.003mol)浓硫酸，缓慢加热至回流，反应5h。待反应液冷却后，常压蒸馏，回收过剩的二甲苯和葫芦巴内酯。冷却后将反应物移到分液漏斗中，先用150ml水洗涤，用碳酸氢钠中和成碱性，再用150ml水洗涤，分离出的粗产物用0.8g无水碳酸镁干燥。进行减压蒸馏，用柱层析进一步实现纯化，洗脱剂为v(二氯甲烷：甲醇)＝10:1，得4.38g目标产物。将薄荷甲酸葫芦巴酯以1000倍的95％乙醇溶解，再将薄荷甲酸葫芦巴酯溶液与烟丝按照0.1：100的质量比均匀喷洒在烟丝中。
实施例3：在装有搅拌器、分水器、回流冷凝管、温度计的三口烧瓶中，加入薄荷甲酸3.72g(0.020mol)，葫芦巴内酯5.12g(0.040mol)，加入30ml二甲苯，缓慢搅拌，慢慢滴加0.37g(0.004mol)浓硫酸，缓慢加热至回流，反应4h。待反应液冷却后，常压蒸馏，回收过剩的二甲苯和葫芦巴内酯。冷却后将反应物移到分液漏斗中，先用400ml水洗涤，用碳酸氢钠中和成碱性，再用400ml水洗涤，分离出的粗产物用1g无水碳酸镁干燥。进行减压蒸馏，用柱层析进一步实现纯化，洗脱剂为v(二氯甲烷：甲醇)＝8:1，得4.54g目标产物。将薄荷甲酸葫芦巴酯以1000倍的95％乙醇溶解，再将薄荷甲酸葫芦巴酯溶液与烟丝按照0.5：100的质量比均匀喷洒在烟丝中。
实施例4：在装有搅拌器、分水器、回流冷凝管、温度计的三口烧瓶中，加入薄荷甲酸3.72g(0.020mol)，葫芦巴内酯2.05g(0.016mol)，加入45ml二甲苯，缓慢搅拌，慢慢滴加0.1g(0.001mol)浓硫酸，缓慢加热至回流，反应3h。待反应液冷却后，常压蒸馏，回收过剩的二甲苯和葫芦巴内酯。冷却后将反应物移到分液漏斗中，先用360ml水洗涤，用碳酸氢钠中和成碱性，再用360ml水洗涤，分离出的粗产物用1.2g无水碳酸镁干燥。进行减压蒸馏，用柱层析进一步实现纯化，洗脱剂为v(二氯甲烷：甲醇)＝3:1，得3.75g目标产物。将薄荷甲酸葫芦巴酯以1000倍的95％乙醇溶解，再将薄荷甲酸葫芦巴酯溶液与烟丝按照1：100的质量比均匀喷洒在烟丝中。
薄荷甲酸葫芦巴酯不同的添加比例对卷烟感官评吸效果有着不同的影响，本发明申请人对薄荷甲酸葫芦巴酯在卷烟中不同添加比例进行实验研究，通过评吸，确定薄荷甲酸葫芦巴酯在卷烟中的合适用量范围和最佳用量。本次实验是将薄荷甲酸葫芦巴酯以1000倍的乙醇溶解，以加香的方式将薄荷甲酸葫芦巴酯溶液均匀喷洒在烟丝中，薄荷甲酸葫芦巴酯溶液与烟丝的质量比为0.01～1：100。
评价结果见表1：
表1薄荷甲酸葫芦巴酯施加比例及卷烟感官评价效果
参加评吸的共十八名评委：其中四名是国家级评委，七名省级评委，七名厂级评委。
根据评吸结果，薄荷甲酸葫芦巴酯能够在卷烟抽吸时能够明显的赋予烟气葫芦巴内酯甘蔗糖蜜样的、略带焦香果味的特征香气，柔和烟气并增加烟气浓度的作用，用量到1％后，烟草本香被压抑，刺激加大。因此可以认为适合用量0.1～0.5％。由于本实验是先将薄荷甲酸葫芦巴酯以1000倍的乙醇溶解，再添加于烟丝中的质量比为0.01～1：100，所以只要加入极少量薄荷甲酸葫芦巴酯达到较明显的改善卷烟烟气的效果，说明使用本发明提供的薄荷甲酸葫芦巴酯不会增加卷烟生产的成本。
以上所述，仅为本发明的具体实施方式，但本发明的保护范围并不局限于此，任何属于本技术领域的技术人员在本发明揭露的技术范围内，可轻易想到的变化或替换，都应涵盖在本发明的保护范围之内。因此，本发明的保护范围应该以权利要求的保护范围为准。
Claims (3)
1.一种薄荷甲酸葫芦巴酯的制备方法，其特征在于所述制备方法如下：
在反应器中加入薄荷甲酸、二甲苯及葫芦巴内酯，在催化剂浓硫酸作用下反应，其化学反应式如下：
所述制备方法具体为：
(1)在装有搅拌器、分水器、回流冷凝管、温度计的混合容器中加入薄荷甲酸、葫芦巴内酯和二甲苯；薄荷甲酸与葫芦巴内酯和二甲苯的摩尔比分别为1︰0.7～3，1:5～20；
(2)缓慢搅拌，慢慢滴加浓硫酸，薄荷甲酸与浓硫酸的摩尔比为1:0.04～0.2，缓慢加热至回流，反应2～7h；
(3)待反应液冷却后，常压蒸馏，回收过剩的二甲苯和葫芦巴内酯；
(4)冷却后将反应物移到分液漏斗中，先用二甲苯体积分数5～15倍的水洗涤，用碳酸氢钠中和成碱性，再用二甲苯体积分数5～15倍的水洗涤，得到的粗产物用薄荷甲酸摩尔质量0.2～0.8倍的无水碳酸镁干燥；
(5)用硅胶柱层析进一步纯化，洗脱剂为二氯甲烷：甲醇按照2～10:1体积比配比而成，即得到薄荷甲酸葫芦巴酯。
2.一种如权利要求1所述方法制备的薄荷甲酸葫芦巴酯。
3.一种如权利要求1所述方法制备的薄荷甲酸葫芦巴酯的应用，其特征在于：将薄荷甲酸葫芦巴酯以1000倍的乙醇溶解形成薄荷甲酸葫芦巴酯溶液，薄荷甲酸葫芦巴酯溶液与烟丝按照0.01～1：100的质量比添加到烟丝中。
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| CN102942484A (zh) * | 2012-12-10 | 2013-02-27 | 郑州轻工业学院 | 一种薄荷基甲酸酯类化合物及其制备方法与应用 |
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