CN106458806A - 短链的多元醇的合成 - Google Patents
短链的多元醇的合成 Download PDFInfo
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Abstract
在此披露了合成短链的多元醇的方法。进一步披露了水解多糖的方法。本发明还针对选择性合成山梨糖醇的方法。
Description
技术领域
本发明总体上涉及在均相酸或沸石不存在下由可溶性纤维素催化合成短链的多元醇,包括山梨糖醇和1,2,5,6-己四醇(HTO)。
发明背景
由纤维素合成山梨糖醇的方法是众所周知的。Fukuoka等人报道了糖醇可以使用负载的铂或钌催化剂由纤维素制备,这显示出对于将纤维素转化为糖醇的高活性,其中支持材料的选择是重要的。Fukuoka等人,纤维素催化转化为糖醇(Catalytic Conversion of Cellulose into Sugar Alcohols),118德国应用化学(Agnew.Chem.)5285-87(2006年)。所述机制包括将纤维素水解为葡萄糖,然后将葡萄糖还原为山梨糖醇和甘露糖醇。
最近,Verendel等人综述了在各种条件下将多糖转化为小的有机分子的一锅法转化率。Verendel等人,由多糖一锅法催化生产小的有机物(Catalytic One-Pot Production of Small Organics from Polysaccharides),11合成(Synthesis),1649-77(2011)。披露了如产生最高达90%的山梨糖醇的纤维素在酸性条件和高压下的水解氢化,但是这些工艺被划分为“绝不简单的”。还披露了通过负载的金属在氢气下没有加入可溶性酸将淀粉、菊粉、和多糖水解产物直接水解氢化为糖醇。将沉积在氧化铝上的钌或铂、负载于活性碳上的各种金属、以及沸石报道为用于纤维素降解的适合的催化剂。还披露了在产生山梨糖醇的酸性条件下过渡金属纳米团簇对于纤维二糖的降解的作用。一项不同研究考虑在负载的钌催化剂上将具有不同结晶度的纤维素转化为多元醇,其中负载在碳纳米管上的钌给出73%的己糖醇的最好产率。
对于由具有高选择性的纤维素并且通过替代途径生产包括糖醇的短链的多元醇的成本有效的方法仍然存在需要。
发明概述
本发明在第一方面涉及一种合成短链的多元醇的方法,所述方法包括将包含至少一种具有高聚合度的组分的进料溶液与氢气在至少一种催化剂存在下反应;其中不加入均相无机酸;由此制成至少一种短链的多元醇。
本发明在另一个方面涉及一种水解多糖的方法,所述方法包括使包含约3%的糖浓度的原料与催化剂在氢气的存在下接触;其中所述原料进一步包含至少一种具有大于3的聚合度(DP)数的组分;其中不加入均相无机酸;结果是至少一种短链的多元醇的形成以及所述至少一种具有大于3的DP数的组分的减少。
本发明在还另一方面涉及一种选择性生产山梨糖醇的方法,所述方法包括使进料溶液与催化剂在氢气的存在下接触;其中使进料溶液包含选自下组的化合物,所述组由可溶性纤维素、淀粉、麦芽糊精、麦芽糖醇以及其任何组合组成;其中不加入均相无机酸;由此产生如与所形成的其他化合物相比具有更高比例的山梨糖醇的产物。
附图简要说明
图1示出了使用负载在碳上的钌-硫(Ru-S/C)催化剂和铜(Cu)催化剂由淀粉或麦芽糊精进料(高聚合度[DP]进料)合成山梨糖醇的方案。
图2示出了DP水解(高聚合度化合物如麦芽糖醇的水解)和糖氢化(山梨糖醇和1,2,5,6-己四醇[HTO]的形成)的方案。
本发明的说明性实施方式的详细说明
在说明性实施例中,本发明的方法包括合成短链的多元醇,所述方法包括将包含至少一种具有高聚合度的组分的进料溶液与氢气在至少一种催化剂存在下反应;其中不加入均相无机酸;由此制成至少一种短链的多元醇。
在另一个说明性实施例中,本发明的方法包括水解多糖,所述方法包括将包含约3%的糖浓度的原料与催化剂在氢气的存在下接触;其中所述原料进一步包含至少一种具有大于3的聚合度(DP)数的组分;其中不加入均相无机酸;结果是至少一种短链的多元醇的形成以及所述至少一种具有大于3的DP数的组分的减少。
在还另一个说明性实施例中,本发明的方法包括选择性生产山梨糖醇,所述方法包括将进料溶液与催化剂在氢气的存在下接触;其中所述进料溶液包含选自下组的化合物,所述组由可溶性纤维素、淀粉、麦芽糊精、麦芽糖醇以及其任何组合组成;其中不加入均相无机酸;由此产生如与所形成的其他化合物相比具有更高比例的山梨糖醇的产物。
在另一个实施例中,所述至少一种具有高聚合度组分选自下组,所述组由以下项组成:纤维素、多糖、淀粉、麦芽糊精、麦芽糖醇、以及其任何组合。在又另一个实施例中,所述至少一种具有高聚合度的组分以大于约0.5%的量存在于所述进料溶液中。在还另一个的实施例中,所述至少一种具有高聚合度的组分具有大于3的聚合度(DP)数。
本发明考虑各种进料溶液和原料。在另一个的实施例中,所述进料溶液进一步包含约3%的糖浓度。在另一个的实施例中,所述原料进一步包含选自下组的化合物,所述组由麦芽糊精、可溶性纤维素、麦芽糖醇以及其任何组合组成。在又另外的实施例中,所述进料溶液或原料进一步包含溶剂。在还另一个实施例中,所述溶剂包含水。
在另一个实施例中,包含所述至少一种具有高聚合度的组分的进料溶液与氢气在所述至少一种催化剂存在下的所述反应在约1200磅/平方英寸的压力下进行。在另一个实施例中,所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触在约1200磅/平方英寸的压力下进行。在另一个实施例中,所述进料溶液与所述催化剂在氢气存在下的所述接触在约1200磅/平方英寸的压力下进行。
本发明考虑不同的催化剂,包括海绵铜、Ru-S/C(负载在碳上的硫化物-钌)、以及其任何组合。
在另一个实施例中,包含所述至少一种具有高聚合度的组分的进料溶液与氢气在所述至少一种催化剂存在下的所述反应进一步包括:使包含所述至少一种具有高聚合度的组分的进料溶液与氢气在第一温度下在第一催化剂存在下反应,由此形成第一产物;并且使所述第一产物在第二温度下在第二催化剂存在下反应,由此制成所述至少一种短链的多元醇。在又另一个实施例中,所述第一催化剂由Ru-S/C组成。在还另一个实施例中,所述第一温度是120℃。在又另一个实施例中,所述第二催化剂由铜组成。在还另一个实施例中,所述第二温度是200℃。
在另一个实施例中,包含所述至少一种具有高聚合度的组分的进料溶液与氢气在所述至少一种催化剂存在下的所述反应在低于约225℃的温度下进行。在又另一个实施例中,包含所述至少一种具有高聚合度的组分的进料溶液与氢气在所述至少一种催化剂存在下的反应在约100℃与约223℃之间的温度下进行。在另一个实施例中,所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触在低于约225℃的温度下进行。在又另一个实施例中,所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触在约100℃与约223℃之间的温度下进行。在另一个实施例中,所述进料溶液与所述催化剂在氢气存在下的所述接触在低于约225℃的温度下进行。在又另一个实施例中,所述进料溶液与所述催化剂在氢气存在下的所述接触在约100℃与约223℃之间的温度下进行。
在另一个实施例中,包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触通过选自由分批法和连续法组成的组的方法进行。
在另一个实施例中,所述至少一种短链的多元醇包含选自下组的化合物,所述组由以下项组成:山梨糖醇、甘露醇、葡萄糖醇、半乳糖醇、1,2,5,6-己四醇、以及其任何组合。
在另一个实施例中,所述产物包含至少25%的山梨糖醇。
在另一个实施例中,所述产物包含小于约1%的C5多元醇。
现在参考附图,提供用于合成根据本发明的短链的多元醇的方法、根据另一方面用于水解多糖、以及根据又另一方面用于选择性合成山梨糖醇的各种方案。因此,在图1中示出了用于使用Ru-S/C催化剂和铜(Cu)催化剂由淀粉或至少一种具有高聚合度[DP]的组分进料合成山梨糖醇的方案。将淀粉或至少一种具有高DP的组分进料在氢气和Ru-S/C催化剂存在下在120℃反应,形成第一产物。然后使所述第一产物在铜催化剂存在下在200℃反应,由此产生山梨糖醇。
在图2中示出了用于DP水解(具有高聚合度的至少一种组分如麦芽糖醇的水解)和糖氢化(1,2,5,6-己四醇[HTO]的合成)的方案。将麦芽糖醇与氢气在铜催化剂存在下反应。因为催化剂是双官能的,所述催化剂可以用于水解和氢化两者,从而产生山梨糖醇和HTO。
通过以下非限制性实例更具体地说明本发明:
实例1:将含有3%的糖和1%的具有高DP数(大于3)的化合物在溶剂(优选水)中的原料溶液的等份部分、处于1200磅/平方英寸的H2、以及海绵铜催化剂结合以便在1升(L)的分批反应器中在许多反应温度下反应。测试了温度对于水解/氢化的作用。
表1:温度对于水解/氢化的影响
表2:温度对于水解/氢化的影响
由此,确定了海绵铜催化剂可以催化具有高DP数的化合物的水解并且在一定范围的温度下可以将糖还原为糖醇,同时以良好的选择性生产山梨糖醇。
实例2:将淀粉(290g,J.T.Baker)、Ru-S/C催化剂(10.0g)、和水(325.0g)加入到1升(L)的不锈钢高压釜式反应器内,并且用氢气(800磅/平方英寸)吹扫所述反应器三次。将所述反应器在1200rpm搅拌下加热至225℃。反应后,将产物过滤。过滤的水溶性产物通过高效液相色谱(HPLC)分析。以高选择性生产HTO。
已经参考某些实例说明了本发明。然而应该认识到对于本领域技术人员来说可以对任何这些实例做出多种替换、改变或组合而不背离本发明的精神和范围。因此,本发明不是由实例的说明、而是由所附的原始提交的权利要求书所限制。
Claims (33)
1.一种合成短链的多元醇的方法,所述方法包括:
将包含至少一种具有高聚合度的组分的进料溶液与氢气在至少一种催化剂存在下反应;
其中不加入均相无机酸;
由此制成至少一种短链的多元醇。
2.如权利要求1所述的方法,其中所述至少一种具有高聚合度的组分选自由以下项组成的组:纤维素、多糖、淀粉、麦芽糊精、麦芽糖醇、以及其任何组合。
3.如权利要求1-2中任一项所述的方法,其中所述进料溶液进一步包含约3%的糖浓度。
4.如权利要求1-3中任一项所述的方法,其中所述进料溶液进一步包含溶剂。
5.如权利要求4所述的方法,其中所述溶剂包含水。
6.如权利要求1-5中任一项所述的方法,其中所述至少一种具有高聚合度的组分以大于约0.5%的量存在于所述进料溶液中。
7.如权利要求1-6中任一项所述的方法,其中包含所述至少一种具有高聚合度的组分的所述进料溶液与氢气在所述至少一种催化剂存在下的所述反应在约1200磅/平方英寸的压力下进行。
8.如权利要求1-7中任一项所述的方法,其中所述至少一种催化剂选自由以下项组成的组:海绵铜、负载在碳上的钌-硫、以及其任何组合。
9.如权利要求1-8中任一项所述的方法,其中包含所述至少一种具有高聚合度的组分的所述进料溶液与氢气在所述至少一种催化剂存在下的所述反应进一步包括:
将包含所述至少一种具有高聚合度的组分的所述进料溶液与氢气在第一温度下在第一催化剂存在下反应,由此形成第一产物;并且
将所述第一产物在第二温度在第二催化剂存在下反应,由此制成所述至少一种短链的多元醇。
10.如权利要求9所述的方法,其中所述第一催化剂由Ru-S/C组成。
11.如权利要求9-10中任一项所述的方法,其中所述第一温度是120℃。
12.如权利要求9-11中任一项所述的方法,其中所述第二催化剂由铜组成。
13.如权利要求9-12中任一项所述的方法,其中所述第二温度是200℃。
14.如权利要求1-8中任一项所述的方法,其中包含所述至少一种具有高聚合度的组分的所述进料溶液与氢气在所述至少一种催化剂存在下的所述反应在低于约225℃的温度下进行。
15.如权利要求1-8中任一项所述的方法,其中包含所述至少一种具有高聚合度的组分的所述进料溶液与氢气在所述至少一种催化剂存在下的所述反应在约100℃与约223℃之间的温度下进行。
16.如权利要求1-15中任一项所述的方法,其中所述至少一种短链的多元醇包含选自下组的化合物,所述组由以下项组成:山梨糖醇、甘露醇、葡萄糖醇、半乳糖醇、1,2,5,6-己四醇、以及其任何组合。
17.如权利要求1-16中任一项所述的方法,其中所述至少一种具有高聚合度的组分具有大于3的聚合度(DP)数。
18.一种水解多糖的方法,所述方法包括:
使包含约3%的糖浓度的原料与催化剂在氢气存在下接触;
其中所述原料进一步包含至少一种具有大于3的聚合度(DP)数的组分;
其中不加入均相无机酸;
结果是至少一种短链的多元醇的形成以及所述至少一种具有大于3的DP数的组分的减少。
19.如权利要求18所述的方法,其中所述原料进一步包含选自下组的化合物,所述组由麦芽糊精、可溶性纤维素、麦芽糖醇以及其任何组合组成。
20.如权利要求18-19中任一项所述的方法,其中所述原料进一步包含溶剂。
21.如权利要求20所述的方法,其中所述溶剂包含水。
22.如权利要求18-21中任一项所述的方法,其中所述催化剂选自由以下项组成的组:海绵铜、负载在碳上的钌-硫、以及其任何组合。
23.如权利要求18-22中任一项所述的方法,其中所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触在约1200磅/平方英寸的压力下进行。
24.如权利要求18-23中任一项所述的方法,其中所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触在低于约225℃的温度下进行。
25.如权利要求18-24中任一项所述的方法,其中所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触在约100℃与约223℃之间的温度下进行。
26.如权利要求18-25中任一项所述的方法,其中所述包含约3%的糖浓度的原料与所述催化剂在氢气存在下的所述接触通过选自由分批法和连续法组成的组的方法进行。
27.如权利要求18-26中任一项所述的方法,其中所述至少一种短链的多元醇选自由以下项组成的组:山梨糖醇、半乳糖醇、甘露糖醇、葡萄糖醇、1,2,5,6-己四醇、以及其任何组合。
28.一种选择性合成山梨糖醇的方法,所述方法包括:
使进料溶液与催化剂在氢气存在下接触;
其中所述进料溶液包含选自下组的化合物,所述组由可溶性纤维素、淀粉、麦芽糊精、麦芽糖醇以及其任何组合组成;
其中不加入均相无机酸;
由此产生如与所形成的其他化合物相比具有更高比例的山梨糖醇的产物。
29.如权利要求28所述的方法,其中所述进料溶液与所述催化剂在氢气存在下的所述接触在约1200磅/平方英寸的压力下进行。
30.如权利要求28-29中任一项所述的方法,其中所述进料溶液与所述催化剂在氢气存在下的所述接触在低于约225℃的温度下进行。
31.如权利要求28-30中任一项所述的方法,其中所述进料溶液与所述催化剂在氢气存在下的所述接触在约100℃与约223℃之间的温度下进行。
32.如权利要求28-31中任一项所述的方法,其中所述产物包含至少25%的山梨糖醇。
33.如权利要求28-32中任一项所述的方法,其中所述产物包含少于约1%的C5多元醇。
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