CN101293902B - 一种蔗糖-6-乙酯的合成方法 - Google Patents
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- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
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Abstract
本发明公开了一种三氯蔗糖-6-乙酯的合成方法,包含步骤:将蔗糖加入极性非质子溶剂中,搅拌溶解,得到蔗糖悬浮液;向上述悬浮液中加入乙酰化试剂乙酰腈,搅拌;向前述反应液中加水,搅拌,然后将反应液浓缩,得到浓缩物;向上述浓缩物中依次加入结晶溶剂,搅拌溶解,静置结晶,过滤,干燥即得。本发明提供的蔗糖-6-乙酯合成方法是将蔗糖与乙酰腈反应,具有操作简便、反应条件温和,选择性高、收率高、适合工业化生产等优点。
Description
技术领域
本发明涉及一种有机合成方法,特别涉及在制备三氯蔗糖中的关键中间体--蔗糖-6-乙酯的合成方法。
背景技术
三氯蔗糖是以蔗糖为原料,将氯元素有选择性地置换在蔗糖分子中的三个羟基后的产物,大约有600倍于砂糖的甜味度,味质与砂糖相近,特征是对热和PH有很好的稳定性。自从1976年由英国的台伊特与拉伊尔(Tate&Lyl)公司同伦敦科英埃里扎办思大学的合作研究中被发现以来,逐渐被很多国家接受并使用。
三氯蔗糖的合成方法主要包括全保护法和单酯法两大类。其中单酯法合成三氯蔗糖被更广泛地使用。因此作为单酯法合成三氯蔗糖的关键中间体——蔗糖-6-乙酯的合成一直备受关注。美国专利US6939962公开了一种以醋酸酐为乙酰化试剂,在有机锡试剂的催化下,以环己环为共沸脱水剂合成蔗糖-6-乙酯得到了理想的结果。但该法成本高、操作复杂、原料难以采购。此外,美国专利US5449772、欧洲专利EP0515145也披露了另一种合成蔗糖-6-乙酯的方法,该法以蔗糖与原乙酸三甲酯反应得到环化中间体,水解后得到蔗糖-6-乙酯和蔗糖-4-乙酯的混合物,再以叔丁胺为转位剂将部分蔗糖-4-乙酯转化为蔗糖-6-乙酯。该法操作简便、反应温和,但酰化的选择性不高。此外尚有其他专利披露了蔗糖-6-乙酯的合成方法,如美国专利US5440026以乙烯酮缩二乙醇为酰化剂、日本专利JP2211888用酶催化法、中国专利CN1827628的电解法和CN1453285的固体硫酸盐催化法。这些方法都存在选择性或转化率不理想的缺陷。
发明内容
本发明为解决现有技术中的上述缺陷,提供一种蔗糖-6-乙酯的合成方法,包含以下步骤:
S1.将蔗糖加入极性非质子溶剂中,搅拌溶解,得到蔗糖悬浮液;
S2.向上述悬浮液中加入乙酰化试剂乙酰腈,搅拌;
S3.向S2中的反应液中加水,搅拌,然后将反应液浓缩,得到浓缩物;
S4.向上述浓缩物中依次加入结晶溶剂,搅拌溶解,静置结晶,过滤,干燥即得蔗糖-6-乙酯成品。
优选地,所述乙酰化试剂乙酰腈是将腈基膦酸二乙酯溶于乙酸中反应而得到。
优选地,所述腈基膦酸二乙酯与乙酸反应的温度是25℃~35℃。
优选地,所述腈基膦酸二乙酯与乙酸反应得到的乙酰腈,在反应结束后进行蒸馏提纯。
优选地,所述步骤S2中,加入的乙酰腈与蔗糖的摩尔比为0.8:1~3:1。
优选地,所述极性非质子溶剂是选自N,N-二甲基甲酰胺(DMF)、六甲基膦酰胺、乙腈或丙腈。
优选地,在步骤S2中,乙酰腈与蔗糖的反应温度是20℃~60℃。
优选地,在步骤S4中,所述溶剂是水和丙酮的混合溶剂。
优选地,所述水和丙酮的混合溶剂中,水与丙酮的比例为1:3~1:8。
本发明的蔗糖-6-乙酯合成路线为:
1.乙酰腈的合成:
2.合成蔗糖-6-乙酯
本发明的有益效果是,该蔗糖-6-乙酯的合成方法相比较于现有技术,具有操作简便、反应条件温和,选择性高(蔗糖-6-乙酯/蔗糖-4-乙酯>25)、收率高(>87%),适合工业化生产等优点。
具体实施方式
以下通过具体实施例对本发明作进一步的阐述,但不限制本发明。
实施例1:乙酰腈的合成
在30℃下,向500ml醋酸溶液中加入腈基膦酸二乙酯50g,搅拌反应5小时,通入氨气,然后减压蒸馏、收集馏出液,即得到乙酰腈。
实施例2:合成蔗糖-6-乙酯
干燥粉碎的蔗糖100g,悬浮于500ml DMF中,加入乙酰腈25g,升温至40℃,搅拌反应4小时;待溶液澄清后,加热至50℃继续反应2小时,降至室温,再缓慢滴加30ml水,减压浓缩至近干。随后向浓缩物中加入30ml水,并加热至65℃,待浓缩物全部溶解后,降至室温,在搅拌下缓慢滴加丙酮150ml;室温静置3小时,结晶,过滤、真空干燥结晶物,即得到蔗糖-6-乙酯成品97g(含量98%)。
实施例3:合成蔗糖-6-乙酯
干燥粉碎的蔗糖100g,悬浮于500ml六甲基膦酰胺中,加入乙酰腈50g,升温至20℃,搅拌反应4小时,降至室温,再缓慢滴加60ml水,减压浓缩至近干。随后向浓缩物中加入30ml水,并加热至65℃,待浓缩物全部溶解后,降至室温,在搅拌下缓慢滴加丙酮100ml;室温静置3小时,结晶,过滤、真空干燥结晶物,即得到蔗糖-6-乙酯成品101g(含量97%)。
实施例4:合成蔗糖-6-乙酯
干燥粉碎的蔗糖100g,悬浮于500ml乙腈或丙腈中,加入乙酰腈60g,升温至60℃,搅拌反应2小时,降至室温,再缓慢滴加100ml水,减压浓缩至近干。随后向浓缩物中加入30ml水,并加热至65℃,待浓缩物全部溶解后,降至室温,在搅拌下缓慢滴加丙酮200ml;室温静置3小时,结晶,过滤、真空干燥结晶物,即得到蔗糖-6-乙酯成品100g(含量95%)。
Claims (10)
1.一种蔗糖-6-乙酯的合成方法,其特征在于,包含以下步骤:
S1. 将蔗糖加入极性非质子溶剂中,搅拌溶解,得到蔗糖悬浮液;
S2. 向上述悬浮液中加入乙酰化试剂乙酰腈,搅拌;
S3. 向S2中的反应液中加水,搅拌,然后将反应液浓缩,得到浓缩物;
S4. 向上述浓缩物中依次加入结晶溶剂,搅拌溶解,静置结晶,过滤,干燥即得蔗糖-6-乙酯成品。
2.根据权利要求1所述的蔗糖-6-乙酯的合成方法,其特征在于,所述乙酰化试剂乙酰腈是将腈基膦酸二乙酯溶于乙酸中反应而得到。
3.根据权利要求2所述的蔗糖-6-乙酯的合成方法,其特征在于,所述腈基膦酸二乙酯与乙酸反应的温度是25℃~35℃。
4.根据权利要求2或3所述的蔗糖-6-乙酯的合成方法,其特征在于,所述腈基膦酸二乙酯与乙酸反应得到的乙酰腈,在反应结束后进行蒸馏提纯。
5.根据权利要求1所述的蔗糖-6-乙酯的合成方法,其特征在于,所述乙酰腈与蔗糖的摩尔比为0.8:1~3:1。
6.根据权利要求1所述的蔗糖-6-乙酯的合成方法,其特征在于,所述极性非质子溶剂是选自N,N-二甲基甲酰胺、六甲基膦酰胺、乙腈或丙腈。
7.根据权利要求1所述的蔗糖-6-乙酯的合成方法,其特征在于,在步骤S2中,乙酰腈与蔗糖的反应温度是20℃~60℃。
8.根据权利要求1所述的蔗糖-6-乙酯的合成方法,其特征在于,在步骤S4中,所述溶剂是水和丙酮的混合溶剂。
9.根据权利要求8所述的蔗糖-6-乙酯的合成方法,其特征在于,所述水和丙酮的混合溶剂中,水与丙酮的比例为1:3~1:8。
10.根据权利要求1或8所述的蔗糖-6-乙酯的合成方法,其特征在于,所述结晶的温度条件为10℃~30℃。
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US11/936,960 US8609834B2 (en) | 2007-04-25 | 2007-11-08 | Method for synthesizing sucrose-6-acetic ester |
DE102007053947A DE102007053947B4 (de) | 2007-04-25 | 2007-11-09 | Verfahren zur Synthese von Saccharose-6-Essigsäureester |
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CN102618601B (zh) * | 2012-04-17 | 2013-10-16 | 广西大学 | 利用生物发酵和固定化酶法制备蔗糖-6-乙酯的方法 |
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EP0515145A1 (en) * | 1991-05-21 | 1992-11-25 | TATE & LYLE PUBLIC LIMITED COMPANY | Continuous process for the preparation of sucrose 6-esters |
CN1453285A (zh) * | 2003-05-23 | 2003-11-05 | 广东省食品工业研究所 | 一种蔗糖-6-乙酸酯的合成方法 |
US6939962B2 (en) * | 2000-07-31 | 2005-09-06 | Tate & Lyle Public Limited Company | Method for the synthesis of sucrose-6-esters |
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US2396201A (en) * | 1944-07-01 | 1946-03-05 | Phillips Petroleum Co | Production of acetyl cyanide |
GB2079749B (en) * | 1980-07-08 | 1984-05-31 | Tate & Lyle Ltd | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose |
GB8822674D0 (en) | 1988-09-27 | 1988-11-02 | Tate & Lyle Plc | Preparation of acylated sucrose derivatives |
US5449772A (en) | 1991-05-21 | 1995-09-12 | Tate & Lyle Public Ltd. Co. | Continuous process for the preparation of sucrose 6-esters |
GB9110931D0 (en) | 1991-05-21 | 1991-07-10 | Tate & Lyle Plc | Process for the preparation of sucrose 6-esters |
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- 2007-11-08 US US11/936,960 patent/US8609834B2/en active Active
- 2007-11-09 DE DE102007053947A patent/DE102007053947B4/de active Active
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DE102007053947B4 (de) | 2010-07-29 |
CN101293902A (zh) | 2008-10-29 |
US8609834B2 (en) | 2013-12-17 |
US20080269478A1 (en) | 2008-10-30 |
DE102007053947A1 (de) | 2008-10-30 |
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