CN110684060A - 一种用磺化石墨烯催化剂的烷基糖苷的制备方法 - Google Patents
一种用磺化石墨烯催化剂的烷基糖苷的制备方法 Download PDFInfo
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Abstract
本发明公开了一种用磺化石墨烯催化剂的烷基糖苷的制备方法,主要解决现有合成方法存在的转化不完全以及生产成本高的技术问题。本发明采用将对氨基苯磺酸经重氮化修饰后与氧化石墨烯表面的活性羟基和环氧基反应,得到氧化石墨烯负载的苯磺酸催化剂;将葡萄糖与脂肪醇混溶,以该磺化石墨烯为催化剂,经一步糖苷化反应制备烷基糖苷。
Description
技术领域
本发明涉及一种用磺化石墨烯催化剂的烷基糖苷的制备方法,属于烷基糖苷的制备技术领域。
背景技术
烷基糖苷(APG),是一类有葡萄糖和脂肪醇在酸性条件下失去一分子水缩合而成的表面活性剂,兼具有非离子与阴离子表面活性剂的特性。不同于一般非离子表面活性剂,烷基糖苷无浊点,表面活性高,去污能力和配伍性好,易生物降解,对环境友好,广泛应用于洗涤剂、乳化剂、化妆品、食品及药品行业等。
目前合成烷基糖苷的方法主要有Koenings-Khorr反应制备法、酶催化合成法、乙酰化醇解法、糖的缩酮物醇解法和Fisher合成法等。其中基于Fisher合成法已经被成功应用于烷基糖苷的生产。应用Fisher合成法生产烷基糖苷的主要生产工艺可归纳为两种:直接法和间接法或称转糖苷法。与间接法相比,直接法的操作简便,经济高效,但其反应温度高,反应时间长,易产生大量的焦糖,糖苷化反应难以转化完全。然而,间接法具有反应过程容易控制,反应条件温和,反应时间较短,产品色泽浅等优点,但其生产工艺复杂,生产成本较高。因此,如何合理利用该两种方法,降低烷基糖苷的生产成本以及优化生产工艺条件是当前所需克服的难点之一。
发明内容
本发明的目的是提供一种用磺化石墨烯催化剂的烷基糖苷的制备方法。主要解决现有合成方法存在的转化不完全以及生产成本高的技术问题。
实现本发明的技术解决方案是:一种用磺化石墨烯催化剂的烷基糖苷的制备方法,采用以磺化石墨烯为催化剂,与脂肪醇经一步糖苷化反应,制备烷基糖苷,步骤为:
(1)对氨基苯磺酸重氮盐的制备:将对氨基苯磺酸和亚硝酸钠溶解于盐酸溶液中,在冰浴冷却的条件下,制得对氨基苯磺酸重氮盐。
(2)氧化石墨烯的磺化:将对氨基苯磺酸重氮盐溶于二次蒸馏水,将该溶液缓慢滴加到氧化石墨烯悬浊液中,冰浴,剧烈搅拌;过滤水洗至中性,真空干燥后即为磺化石墨烯催化剂。反应中,氧化石墨烯上的环氧键可以与对氨基苯磺酸重氮盐直接偶联,最终得到带有磺酸基正电位的磺化石墨烯。
(3)将原料以葡萄糖:脂肪醇质量比1:(4~6),加入至反应器中,加热至80℃,预反应20min,向体系中加入催化剂用量为葡萄糖质量的10%的磺化石墨烯,减压反应并升温至140-170℃,30min后停止反应。
(4)热过滤,收集滤液,过滤除去磺化石墨烯,减压蒸馏除去滤液中的脂肪醇得到淡黄色糖浆状液体产物。
反应简式如下:
本发明与现有技术相比,其显著优点是:石墨烯具有分散性好,比表面积大,毒性低等特点,本发明创造性利用氧化石墨烯表面的多羟基和环氧基设计并制备多性能的催化剂。磺化石墨烯,由于磺酸基团的高亲水性,无需对氧化石墨烯进行预还原,对氧化石墨烯进行磺化处理后,不仅可以提高该催化剂的分散性,还可以保留石墨烯的独特性质。本发明获得的催化剂活性大、催化时间短、催化产率高、且可以重复使用,后处理方法简单,通过热过滤除去磺化石墨烯,减压蒸馏即可得到烷基糖苷产品,产品性质稳定,纯度较高,体系中无焦糖副产物生成。
附图说明
图1磺化石墨烯的红外光谱图。
图2氧化石墨烯的红外光谱图。
图3乙基葡萄糖苷的红外光谱图。
图4十二烷基葡萄糖苷的红外光谱图。
图5十二烷基葡萄糖苷的核磁氢谱图。
具体实施方式
以下提供本发明一种用磺化石墨烯催化剂的烷基糖苷的制备方法。
实施例1
(1)对氨基苯磺酸重氮盐的制备:将对氨基苯磺酸和亚硝酸钠溶解于盐酸溶液中,在冰浴冷却的条件下,制得对氨基苯磺酸重氮盐。
(2)氧化石墨烯的磺化:将对氨基苯磺酸重氮盐1.35g溶于10mL二次蒸馏水,将该溶液缓慢滴加到13mL,1mg/mL的氧化石墨烯(红外谱图参见图2)悬浊液中,冰浴,剧烈搅拌6h;过滤水洗至中性,真空干燥后即为磺化石墨烯催化剂。红外谱图参见图1。
(3)在一个带搅拌器的三口烧瓶中加入3g无水葡萄糖(红外谱图参见图3),18g乙醇,预加热80℃回流20min,加入磺化石墨烯0.3g,继续回流155℃加热搅拌30min。
(4)热过滤,收集滤液,过滤除去磺化石墨烯,减压蒸馏除去滤液中的脂肪醇得到淡黄色糖浆状液体产物。产品收率为98%。产物的红外光谱及核磁氢谱参见图4和图5。
实施例2
在一个带搅拌器的三口烧瓶中加入3g无水葡萄糖,15g月桂醇,预加热80℃回流20min,加入磺化石墨烯0.3g,继续回流140℃加热搅拌30min。反应结束后,过滤除去磺化石墨烯,滤液减压蒸馏,得到淡黄色糖浆状产物,产品收率为97%。其余同实施例1。
实施例3
在一个带搅拌器的三口烧瓶中加入3g无水葡萄糖,12g月桂醇,预加热80℃回流20min,加入磺化石墨烯0.3g,继续回流170℃加热搅拌30min。反应结束后,过滤除去磺化石墨烯,滤液减压蒸馏,得到淡黄色糖浆状产物,产品收率为97%。其余同实施例1。
Claims (1)
1.一种用磺化石墨烯催化剂的烷基糖苷的制备方法,其特征是:采用以磺化石墨烯为催化剂,与脂肪醇经一步糖苷化反应,制备烷基糖苷,步骤为:
(1)对氨基苯磺酸重氮盐的制备:将对氨基苯磺酸和亚硝酸钠溶解于盐酸溶液中,在冰浴冷却的条件下,制得对氨基苯磺酸重氮盐;
(2)氧化石墨烯的磺化:将对氨基苯磺酸重氮盐溶于二次蒸馏水,将该溶液缓慢滴加到氧化石墨烯悬浊液中,冰浴,剧烈搅拌;过滤水洗至中性,真空干燥后即为磺化石墨烯催化剂;
(3)将原料以葡萄糖:脂肪醇质量比1:(4~6),加入至反应器中,加热至80℃,预反应20min,向体系中加入催化剂用量为葡萄糖质量的10%的磺化石墨烯,减压反应并升温至140-170℃,30min后停止反应;
(4)热过滤,收集滤液,过滤除去磺化石墨烯,减压蒸馏除去滤液中的脂肪醇得到淡黄色糖浆状液体产物。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08269076A (ja) * | 1995-02-01 | 1996-10-15 | Kao Corp | アルキルグリコシドの製造方法 |
CN103896772A (zh) * | 2014-03-06 | 2014-07-02 | 大连大学 | 一种催化酯化甘油制备甘油酯的方法 |
CN104140453A (zh) * | 2013-10-29 | 2014-11-12 | 中国石油化工股份有限公司 | 一种钻井液用甘油基葡萄糖苷的制备方法 |
WO2015170124A1 (en) * | 2014-05-09 | 2015-11-12 | The University Of Manchester | Functionalised graphene |
CN107673343A (zh) * | 2016-08-02 | 2018-02-09 | 福建新峰二维材料科技有限公司 | 一种石墨烯纳米材料的制备方法 |
-
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08269076A (ja) * | 1995-02-01 | 1996-10-15 | Kao Corp | アルキルグリコシドの製造方法 |
CN104140453A (zh) * | 2013-10-29 | 2014-11-12 | 中国石油化工股份有限公司 | 一种钻井液用甘油基葡萄糖苷的制备方法 |
CN103896772A (zh) * | 2014-03-06 | 2014-07-02 | 大连大学 | 一种催化酯化甘油制备甘油酯的方法 |
WO2015170124A1 (en) * | 2014-05-09 | 2015-11-12 | The University Of Manchester | Functionalised graphene |
CN107673343A (zh) * | 2016-08-02 | 2018-02-09 | 福建新峰二维材料科技有限公司 | 一种石墨烯纳米材料的制备方法 |
Non-Patent Citations (1)
Title |
---|
DILANTHA THUSHARA,等: "磺化石墨烯固体酸催化剂的制备及活性评价", 《工业催化》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112500366A (zh) * | 2020-11-18 | 2021-03-16 | 合肥工业大学 | 一种石墨烯共价嫁接噻唑盐催化剂及其应用 |
CN112500366B (zh) * | 2020-11-18 | 2023-09-12 | 合肥工业大学 | 一种石墨烯共价嫁接噻唑盐催化剂及其应用 |
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