WO2018086529A1 - 一种酶法制备丁酸甘油酯的方法 - Google Patents

一种酶法制备丁酸甘油酯的方法 Download PDF

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WO2018086529A1
WO2018086529A1 PCT/CN2017/109920 CN2017109920W WO2018086529A1 WO 2018086529 A1 WO2018086529 A1 WO 2018086529A1 CN 2017109920 W CN2017109920 W CN 2017109920W WO 2018086529 A1 WO2018086529 A1 WO 2018086529A1
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butyric acid
reaction
lipase
glycerol
esterification
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王永华
王卫飞
杨博
蓝东明
王方华
李雪辉
朱东奇
李道明
李志刚
陈华勇
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South China University of Technology SCUT
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6454—Glycerides by esterification
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • C12N9/20—Triglyceride splitting, e.g. by means of lipase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C12Y301/01003—Triacylglycerol lipase (3.1.1.3)

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  • butyric acid Compared with other short-chain fatty acids, the bactericidal activity of butyric acid is not decomposed. Well, it is considered a potential substitute for antibiotics. Because of the liquid form and volatility of butyric acid, as well as the special odor, it is not easy to use directly in feed or food. As a precursor of butyric acid, glyceryl butyrate is easy to use, safe, non-toxic and side-effect, and has no odor. It not only solves the problem that butyric acid is difficult to be added in liquid volatile, but also improves the shortcomings of direct use of butyric acid. It also has a good nutritional additive product, which promotes the healthy development of the intestines of livestock and poultry, improves the immunity of the body, promotes the digestion and absorption of nutrients, and improves the performance of animals.
  • Butyric acid glyceride has great potential in the field of animal feed, and many people have also explored the synthesis process of glyceryl butyrate.
  • CN102090517A is a process for preparing butyric acid mono-diglyceride by using butyric acid and glycerin as reactants, carbon tetrachloride as water-carrying agent and phosphoric acid as catalyst; after washing carbon tetrachloride, washing is carried out by using saturated saline solution having a pH of 10; Phosphoric acid.
  • CN 102850215A is a process for preparing butyric acid glyceride by using toluene as a water-carrying agent, and solid acid catalyzing the esterification of n-butyric acid and glycerol; after the reaction is completed, The catalyst is separated by filtration, and the water-carrying agent is recovered by distillation under reduced pressure to obtain glyceryl butyrate. Since the water-carrying agent is generally toluene or carbon tetrachloride, it is difficult to treat waste water; therefore, a production process that does not use a water-carrying agent has been developed.
  • CN 104045556A discloses a method for preparing tributyrin, which comprises reacting glycerin and butyryl chloride with an organic base as an acid binding agent to obtain a mixture containing tributyrin, and then containing tributyrin. The mixture was extracted with water, the organic phase was collected, and the solvent in the organic phase was evaporated under reduced pressure to give succinate.
  • p-toluenesulfonic acid is used as a catalyst, and water produced by the esterification reaction is discharged by nitrogen gas, and then the reaction product is repeatedly washed with a light alkali solution to obtain a crude product of glyceryl butyrate.
  • a sulfonic acid mesoporous molecular sieve and a ZSM-5 acid zeolite are used to catalyze the esterification of butyric acid with glycerin, while butyric anhydride is added dropwise, and the butyric acid glyceride is synthesized without using a water-carrying agent.
  • the existing synthesis process of butyric acid glyceride generally uses a chemical catalyst such as an acid or a base to carry out an esterification reaction at a high temperature, and the production process consumes high energy, and a complex process is required to recover the product to remove the catalyst.
  • Butyl glyceride is generally used as a functional nutritional supplement for animal feed. Therefore, the development of an efficient and environmentally friendly bio-enzymatic synthesis process is more conducive to the promotion of glyceryl butyrate in the field of functional feed additives.
  • the enzymatic synthesis of fatty acid glycerides is a research direction that has long been of great interest.
  • butyric acid is a short-chain fatty acid which has good mutual solubility with water and glycerin, and has low boiling point and strong volatility. It has great physical and chemical properties with medium-long-chain fatty acids with strong hydrophobicity and high boiling point. The difference.
  • the butyric acid glyceride is produced by the conventional medium-long-chain fatty acid glyceride production process, the catalytic efficiency of the lipase is extremely low; and when the esterification reaction reaches equilibrium, the conversion rate of butyric acid is also very low.
  • the present invention provides an enzymatic preparation of glyceryl butyrate.
  • the method comprises the steps of using a lipase as a catalyst, n-butyric acid and glycerol as a substrate, ethyl acetate and/or ethyl formate as a reaction assistant, and the esterification reaction is carried out at normal temperature and normal pressure without using water. Agent.
  • the present invention aims to achieve the above object, and the technical solution is as follows:
  • a method for enzymatically synthesizing glyceryl butyrate comprises the following steps:
  • lipase as a catalyst, ethyl acetate and/or ethyl formate as a reaction aid, and n-butyric acid and glycerol for esterification;
  • the molar ratio of n-butyric acid to glycerol in the step (1) is from 3:1 to 1:3.
  • the reaction assistant in the step (1) may be ethyl acetate, may be methyl acetate, or may be a mixture of the two in any ratio.
  • the ethyl acetate or ethyl formate is added in an amount of 10% to 60% by mass of n-butyric acid.
  • the lipase is added in an amount of 0.5% to 5% by mass of n-butyric acid.
  • the lipase of the step (1) is a mixture derived from one or more of Rhizopus, Aspergillus, Mucor, bacteria, yeast, and pancreatic lipase.
  • the lipase of the present invention may be a commercialized Lipozyme TL 100L lipase or Lipase, but not limited to this.
  • the temperature of the esterification reaction is 20° C. to 50° C., and the stirring condition is 200 rpm or more; the separation in the step (2) is the preferred natural layering, the organic phase is recovered, and ethyl acetate or ethyl formate is recovered by distillation under reduced pressure to obtain D. Acid glyceride.
  • Fatty acid is a natural substrate of lipase.
  • lipase can be used to efficiently catalyze the esterification of long-chain fatty acids with glycerol.
  • the process of preparing diacylglycerol and polyunsaturated fatty acid glycerides by lipase has been applied.
  • the catalytic activity of lipase is found to be very low in the catalytic process for synthesizing fatty acid glycerides by the existing enzymatic method, and the esterification reaction is balanced. When the conversion rate of butyric acid is also very low.
  • the present inventors have found that the addition of ethyl acetate or ethyl formate as a reaction assistant in the lipase-catalyzed esterification reaction system of butyric acid and glycerol can improve the catalytic efficiency of lipase and increase the conversion rate of butyric acid, thereby forming a this invention.
  • the present invention catalyzes the esterification reaction of n-butyric acid and glycerin at normal temperature and normal pressure with lipase, thereby reducing the energy consumption of the reaction and avoiding the use of the water-carrying agent;
  • the butyric acid conversion rate in the test product was 90.1%, the content of butyric acid monoglyceride in the butyric acid glyceride was 91.7%, and the content of butyric acid diester and tributyrin was 8.3%.
  • the ethyl formate in the organic phase is recovered by distillation under reduced pressure to obtain glyceryl butyrate.
  • the butyric acid conversion rate in the test product was 92.3%
  • the content of butyric acid monoglyceride in the butyric acid glyceride was 87.9%
  • the content of butyric acid diester and tributyrin was 12.2%.
  • the butyric acid conversion rate of the test product was 93.2%, the content of butyric acid monoglyceride in butyric acid glyceride was 51.6%, and the content of butyric acid diester and tributyrin was 48.4%.
  • the butyric acid conversion rate in the test product was 11.4%, the content of butyric acid monoglyceride in the butyric acid glyceride was 77.3%, and the content of butyric acid diester and tributyrin was 22.7%.

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Abstract

一种酶法制备丁酸甘油酯的方法，包括如下步骤：(1)以脂肪酶为催化剂，乙酸乙酯和/或甲酸乙酯作为反应助剂，正丁酸与甘油进行酯化反应；(2)分离反应产物，减压蒸馏回收反应助剂，即获得丁酸甘油酯。使用脂肪酶为催化剂，催化正丁酸与甘油在常温、常压下进行酯化反应，降低了反应能耗，反应条件温和，没有副反应发生，避免了带水剂的使用。此外，反应助剂的添加，提高了脂肪酶的催化效率和丁酸的转化率。

Description

一种酶法制备丁酸甘油酯的方法 技术领域
本发明涉及一种酶法制备丁酸甘油酯的方法。
背景技术
丁酸是在人和动物的肠道中存在的一种短链脂肪酸，为肠道上皮细胞提供能量，促进其生长发育。丁酸甘油酯作为丁酸的前体物质,在医疗、饲料等领域得到了广泛的应用。丁酸甘油酯不能被胃液所分解，其在胰脂肪酶的作用下会缓慢释放出丁酸和甘油。丁酸是反刍动物瘤胃和杂食动物结肠中微生物发酵碳水化合物的产物，近年来研究发现丁酸还具有较强的杀菌作用，和其它短链脂肪酸相比，丁酸未被分解时的杀菌活力最好，被认为是抗生素的潜在替代物。因为丁酸的液体形态和易挥发性，以及特殊的臭味，导致其不易直接在饲料或食品中使用。丁酸甘油酯作为丁酸的前体物，使用方便，安全无毒副作用，无臭味，既解决了丁酸为液态易挥发难以添加的特点，又改善了直接使用丁酸气味难闻的缺点，而且具有促进畜禽肠道健康发育，提高机体免疫能力，促进营养物质消化吸收，进而提高动物生产性能，是目前较好的营养性添加剂产品。
丁酸甘油酯在动物饲料等领域具有极大的应用潜力，人们对丁酸甘油酯的合成工艺也进行了大量的探索。CN102090517A中以丁酸和甘油为反应物，四氯化碳为带水剂、磷酸作催化剂制备丁酸单双甘油酯的工艺；在回收四氯化碳后利用pH为10的饱和食盐水洗涤除去磷酸。CN 102850215A中以甲苯为带水剂，固体酸催化正丁酸和甘油酯化制备丁酸甘油酯的工艺；在反应完成后， 通过过滤分出催化剂，减压蒸馏回收带水剂，即可得到丁酸甘油酯。由于带水剂一般为甲苯或四氯化碳，会产生难以处理的废水；因此，人们对不使用带水剂的生产工艺进行了开发。CN 104045556A公布了一种三丁酸甘油酯的制备方法，以有机碱为缚酸剂，使甘油和丁酰氯进行反应，得到含三丁酸甘油酯的混合物，然后将含三丁酸甘油酯的混合物用水萃取，收集有机相，并将有机相中的溶剂减压蒸发去除，得到三丁酸甘油酯。CN 103012137B中以对甲苯磺酸为催化剂，利用氮气将酯化反应产生的水排出，然后利用淡碱液反复洗涤反应产物后得到丁酸甘油酯粗产物。CN104086422B中以磺酸介孔分子筛与ZSM-5酸性沸石催化丁酸与甘油酯化，同时滴加丁酸酐，不使用带水剂合成丁酸甘油酯。
综上可知，现有的丁酸甘油酯合成工艺一般使用酸、碱等化学催化剂，在高温下进行酯化反应，生产工艺能耗高，而且回收产物时需要复杂的工艺处理才能去除催化剂。丁酸甘油酯一般是用作动物饲料的功能性营养添加剂，因而，开发高效、环保的生物酶法合成工艺更有利于丁酸甘油酯在功能性饲料添加剂领域推广使用。酶法合成脂肪酸甘油酯是长期以来人们非常关注的研究方向，许多脂肪酸(如多不饱和脂肪酸)的酶法合成工艺已经实现产业化。但是，丁酸是一种与水和甘油均有良好互溶性的短链脂肪酸，而且其沸点低、挥发性强，与疏水性较强、沸点较高的中长链脂肪酸的理化性质具有很大的差异。以传统的中长链脂肪酸甘油酯的生产工艺制备丁酸甘油酯时，脂肪酶的催化效率极低；而且酯化反应达到平衡时，丁酸的转化率也非常低。
发明内容
针对现有的丁酸甘油酯合成工艺一般使用的均为化学催化剂，并且需要使用甲苯、四氯化碳等有毒试剂为带水剂，本发明提供一种酶法制备丁酸甘油酯 的方法，采用脂肪酶为催化剂，以正丁酸和甘油为底物，乙酸乙酯和/或甲酸乙酯为反应助剂，酯化反应在常温、常压下进行，且不需使用带水剂。
本发明为实现上述目的，技术方案如下：
一种酶法合成丁酸甘油酯的方法，包括如下步骤：
(1)以脂肪酶为催化剂，乙酸乙酯和/或甲酸乙酯为反应助剂，正丁酸与甘油进行酯化反应；
(2)分离反应产物，回收有机相，即获得丁酸甘油酯。
步骤(1)所述过正丁酸与甘油的摩尔比为3:1～1:3。
步骤(1)所述反应助剂可以是乙酸乙酯、可以是乙酸甲酯、也可是二者任意比例的混合。
所述乙酸乙酯或甲酸乙酯的添加量为正丁酸质量的10％～60％。
所述脂肪酶的添加量为正丁酸质量的0.5％～5％。
步骤(1)所述脂肪酶为源于根霉属、曲霉属、毛霉属、细菌、酵母菌和胰脂肪酶中的一种或一种以上的混合物。本发明脂肪酶可以采用商品化的Lipozyme TL 100L脂肪酶或
Figure PCTCN2017109920-appb-000001
脂肪酶，但不限于此。
所述酯化反应的温度为20℃～50℃，搅拌条件200rpm以上；步骤(2)所述分离为首选自然分层，回收有机相，减压蒸馏回收乙酸乙酯或甲酸乙酯，得到丁酸甘油酯。
脂肪酸是脂肪酶的天然底物，目前人们发现的脂肪酶可以高效催化中长链脂肪酸与甘油进行酯化反应，利用脂肪酶催化制备甘油二酯、多不饱和脂肪酸甘油酯的工艺目前已经应用在实际生产中。由于丁酸具有与中长链脂肪酸不同的理化性质，在利用现有的酶法合成脂肪酸甘油酯的催化工艺制备丁酸甘油酯时，发现脂肪酶的催化活力非常低，在酯化反应达到平衡时，丁酸的转化率也 非常低。这可能是由于现有的脂肪酶均具有界面激活的性质，而丁酸和甘油具有良好的互溶性，酯化反应体系中不能提供界面，这就大大降低了脂肪酶的催化活力。至于为何在反应达到平衡时丁酸的转化率较低，尚没有研究可以解释这一现象。
本发明研究发现，在脂肪酶催化丁酸与甘油的酯化反应体系中添加乙酸乙酯或甲酸乙酯为反应助剂时可以提高脂肪酶的催化效率，提高丁酸的转化率，进而形成了本发明。
与现有技术相比，本发明的有益效果在于：
(1)本发明以脂肪酶催化正丁酸与甘油在常温、常压下进行酯化反应，降低了反应能耗，而且避免了带水剂的使用；
(2)添加乙酸乙酯和/或乙酸甲酯为反应助剂，提高了脂肪酶的催化效率和丁酸的转化率。
具体实施方式
以下通过实施例更详细地介绍本发明的实施。在所述实施例中，所有百分比均以质量计。反应产物中丁酸的含量利用气相色谱进行检测，丁酸转化率按下式计算：
Figure PCTCN2017109920-appb-000002
实施例1
在反应容器中加入正丁酸88g，甘油92g，乙酸乙酯10g，混合均匀后添加Lipozyme TL 100L脂肪酶1.0g(购自诺维信(中国)生物技术有限公司)，开始酯化反应。控制反应体系的温度为40℃，搅拌速度为400rpm。持续反应12h后，酯化反应基本达到平衡，停止搅拌终止酯化反应，将反应混合物静置5min进行分层，回收上层有机相。减压蒸馏回收有机相中的乙酸乙酯，即得 到丁酸甘油酯。经检测产物中丁酸转化率为90.1％，丁酸甘油酯中丁酸单甘油酯的含量为91.7％，丁酸二酯和三丁酸甘油酯的含量为8.3％。
实施例2
在反应容器中加入正丁酸176g，甘油184g，甲酸乙酯100g，混合均匀后添加Lipozyme TL 100L脂肪酶3.0g(购自诺维信(中国)生物技术有限公司)，开始酯化反应。控制反应体系的温度为40℃，搅拌速度为400rpm。持续反应12h后，酯化反应基本达到平衡，停止搅拌终止酯化反应，将反应混合物静置5min进行分层，回收上层有机相。减压蒸馏回收有机相中的甲酸乙酯，即得到丁酸甘油酯。经检测产物中丁酸转化率为92.3％，丁酸甘油酯中丁酸单甘油酯的含量为87.9％，丁酸二酯和三丁酸甘油酯的含量为12.2％。
实施例3
在反应容器中加入正丁酸88g，甘油46g，乙酸乙酯10g,混合均匀后添加
Figure PCTCN2017109920-appb-000003
脂肪酶1.0g(购自诺维信(中国)生物技术有限公司)，开始酯化反应。控制反应体系的温度为45℃，搅拌速度为400rpm。持续反应12h后，酯化反应基本达到平衡，停止搅拌终止酯化反应，将反应混合物静置5min进行分层，回收上层有机相。减压蒸馏回收有机相中的乙酸乙酯，即得到丁酸甘油酯。经检测产物中丁酸转化率为93.2％，丁酸甘油酯中丁酸单甘油酯的含量为51.6％，丁酸二酯和三丁酸甘油酯的含量为48.4％。
对比实施例1
在反应容器中加入正丁酸88g，甘油92g，混合均匀后添加Lipozyme TL100L脂肪酶1.0g，开始酯化反应。控制反应体系的温度为40℃，搅拌速度为400rpm。持续反应12h后，停止搅拌终止酯化反应，将反应混合物静置5min进行分层，回收上层有机相即得到丁酸甘油酯。经检测产物中丁酸转化率为 7.4％，丁酸甘油酯中以丁酸单甘油酯为主。
对比实施例2
在反应容器中加入正丁酸88g，甘油46g，混合均匀后添加
Figure PCTCN2017109920-appb-000004
脂肪酶1.0g，开始酯化反应。控制反应体系的温度为45℃，搅拌速度为200rpm。持续反应12h后，酯化反应基本达到平衡，停止搅拌终止酯化反应，将反应混合物静置5min进行分层，回收上层有机相即得到丁酸甘油酯。经检测产物中丁酸转化率为11.4％，丁酸甘油酯中丁酸单甘油酯的含量为77.3％，丁酸二酯和三丁酸甘油酯的含量为22.7％。

Claims (7)

  1. 一种酶法制备丁酸甘油酯的方法，其特征在于，包括如下步骤：
    (1)以脂肪酶为催化剂，乙酸乙酯和/或甲酸乙酯作为反应助剂，正丁酸与甘油进行酯化反应；
    (2)分离反应产物，减压蒸馏回收反应助剂，即获得丁酸甘油酯。
  2. 根据权利要求1所述的方法，其特征在于，所述反应助剂的添加量为正丁酸质量的10％～60％。
  3. 根据权利要求1所述的方法，其特征在于，步骤(1)所述正丁酸与甘油的摩尔比在3:1～1:3。
  4. 根据权利要求1或2或3所述的方法，其特征在于，所述脂肪酶的添加量为正丁酸质量的0.5％～10％。
  5. 根据权利要求4所述的方法，其特征在于，步骤(1)所述脂肪酶为来源于根霉属、曲霉属、毛霉属、细菌、酵母菌的脂肪酶和胰脂肪酶中的一种或两种以上的混合物。
  6. 根据权利要求4所述的方法，其特征在于，所述酯化反应的温度为20℃～50℃，搅拌条件200rpm以上。
  7. 根据权利要求4所述的方法，其特征在于，步骤(2)所述分离过程为自然分层，回收有机相，减压蒸馏回收乙酸乙酯，得到丁酸甘油酯。
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