WO2020007334A1 - 一种三饱和脂肪酸甘油酯以及usu型甘油三酯 - Google Patents

一种三饱和脂肪酸甘油酯以及usu型甘油三酯 Download PDF

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WO2020007334A1
WO2020007334A1 PCT/CN2019/094643 CN2019094643W WO2020007334A1 WO 2020007334 A1 WO2020007334 A1 WO 2020007334A1 CN 2019094643 W CN2019094643 W CN 2019094643W WO 2020007334 A1 WO2020007334 A1 WO 2020007334A1
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fatty acid
saturated fatty
glyceride
trisaturated
reaction
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PCT/CN2019/094643
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English (en)
French (fr)
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李翔宇
陆姝欢
张力文
马凡提
汪志明
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嘉必优生物技术（武汉）股份有限公司
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Publication of WO2020007334A1 publication Critical patent/WO2020007334A1/zh

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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
    • 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

Definitions

  • the present application relates to the technical field of glyceride synthesis and processing, in particular to a trisaturated fatty acid glyceride and a USU-type triglyceride.
  • the synthesis methods of trisaturated fatty acid glycerides mainly include: random transesterification of triglycerides under the action of chemical catalysts and the reaction of glycerol and saturated fatty acids at high temperature (180 ° C to 200 ° C).
  • the purity of trisaturated fatty acid glycerides is not high by random transesterification of triglycerides under the action of chemical catalysts.
  • the disadvantages of the reaction of glycerol and saturated fatty acids at high temperature 180 ° C to 200 ° C) are that the reaction requires high temperature, the process reaction conditions are harsh, and there are many side reactions.
  • the purpose of the present application is to provide a method for preparing trisaturated fatty acid glyceride, which can make the purity of trisaturated fatty acid glyceride high, and the reaction conditions are simple and the side reactions are few.
  • the present invention provides a method for preparing a trisaturated fatty acid glyceride, which comprises: catalyzing a glyceride containing a saturated fatty acid residue and a saturated fatty acid salt under the action of a non-directional lipase to obtain the trisaturated fatty acid Glyceride.
  • the saturated fatty acid residue is the same as the corresponding saturated fatty acid in the saturated fatty acid salt
  • the glyceride containing the saturated fatty acid residue has at least one ester bond or hydroxyl group not bonded to the saturated fatty acid residue.
  • the present application also relates to a USU-type triglyceride, which is synthesized by using the trisaturated fatty acid glyceride as a raw material.
  • a trisaturated fatty acid glyceride provided by some embodiments of the present application is obtained by the following preparation method: a glyceride containing a saturated fatty acid residue and a saturated fatty acid salt are subjected to a catalytic reaction under the action of a non-directional lipase to obtain Trisaturated fatty acid glyceride.
  • the saturated fatty acid residues are the same as the corresponding saturated fatty acids in the saturated fatty acid salt.
  • glycerides contain saturated fatty acid residues that are palmitic acid residues (does not exclude other kinds of saturated fatty acid residues that contain non-palmitic acid residues. Base), then the corresponding saturated fatty acid salt is palmitate.
  • the glyceride containing a saturated fatty acid residue has at least one ester bond or a hydroxyl group which is not bonded to the saturated fatty acid residue.
  • the glyceride as a raw material is at least one of a monoglyceride, a diglyceride, and a triglyceride, and a part of the ester bond is an ester bond obtained by combining with (specified above) a saturated fatty acid.
  • the glyceride may be a monoglyceride or a diglyceride, or a triglyceride, or a mixture of a diglyceride and a triglyceride.
  • the catalytic reaction includes a transesterification reaction and an esterification reaction.
  • the transesterification reaction is mainly performed.
  • the glyceride includes a part of a diglyceride or a monoglyceride, an ester is also present. ⁇ ⁇ Reaction.
  • the ratio of glyceride to saturated fatty acid salt is based on the amount of saturated fatty acid salt added, so that the proportion of saturated fatty acid residues in the reaction system to the total fatty acid residues is greater than or equal to 90%, and preferably greater than 92%, more preferably greater than 95%.
  • the saturated fatty acid salt can be added such that the proportion of saturated fatty acid residues in the reaction system to the total fatty acid residues is 91%, 92%, 93%, 94%, 95%, 96%, 97%, or 98% Wait.
  • the ratio of the reactants By setting the ratio of the reactants, the progress of the transesterification reaction or the esterification reaction can be fully satisfied, and further, the reactants can be sufficiently contacted to obtain a reaction product with higher purity.
  • the amount of lipase is 0.05 to 10% of glyceride, preferably 0.1 to 8%.
  • the amount of Novozym 435 is 4 to 8% or Lipase DF "Amano" 15
  • the addition amount is 0.1 to 1%
  • the addition amount of LipozymeTLIM is 4 to 8%
  • the addition amount of LipaseAY30G is 0.1 to 1%.
  • the amount of lipase added may be 0.05%, 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, or 9%.
  • the amount of lipase added has an important effect on the reaction process.
  • the catalytic effect cannot be achieved. If the amount of lipase is too low, the catalytic effect cannot be achieved. If the amount of lipase is too high, the cost will increase, and it will affect the reaction between the reactants to a certain extent. Contact results in poor response. Therefore, by adding the non-directional lipase in the above range, the catalytic effect on the reaction can be sufficiently achieved, so that the reaction proceeds more thoroughly within the predetermined reaction time.
  • the lipase includes at least one of non-directional lipase and directional lipase.
  • the lipase is non-directional lipase, and the non-directional lipase is Novozym 435, Lipase DF "Amano" 15, LipozymeTLIM and LipaseAY30G At least one of.
  • the non-targeted lipase may be Novozym 435 or Lipase DF "Amano" 15 or a mixture of Novozym 435 and Lipase DF "Amano" 15.
  • the non-directional lipase is Lipase DF "Amano" 15.
  • the temperature of the catalytic reaction is 30-90 ° C, preferably 35-85 ° C, further preferably, the reaction temperature of LipozymeTLIM is 65-70 ° C, the reaction temperature of Novozym 435 is 75-85 ° C, and Lipase DF "Amano" 15
  • the reaction temperature is 35 to 40 ° C
  • the LipaseAY30G reaction temperature is 35 to 40 ° C.
  • the time for the catalytic reaction is 0.5 to 9 hours, and the preferred reaction time is 1 to 4 hours.
  • the reaction temperature is relatively low compared to the reaction temperature of traditional chemical catalysts, and the reaction is easier.
  • the reaction temperature can be kept constant by heating in a water bath. The water bath is heated more uniformly, and the heat transfer effect is good. Makes the reaction easier. Of course, other heating methods such as furnace heating can also be used to maintain the reaction temperature.
  • the corresponding saturated fatty acid in the saturated fatty acid residue and the saturated fatty acid salt is selected from palmitic acid, stearic acid, caprylic acid, capric acid, lauric acid, myristic acid, or arachidic acid.
  • the reactant may be
  • the glycerides and palmitates of palmitic acid residues may also be the glycerides and stearate salts containing stearic acid residues, or the glycerides and laurate salts of lauric acid residues. Palmitic acid or stearic acid is preferred, and palmitic acid is more preferred.
  • fatty acid salts as a strong base and weak acid salt, have strong ionization ability, strong fatty acid residue activity, and the ability to provide fatty acid residues is far greater than free fatty acids or fatty acid esters. Therefore, the rate of transesterification reaction can be accelerated, the reaction time can be shortened, the amount of lipase can be reduced, and the cost can be reduced.
  • the glyceride containing saturated fatty acid residues may be cocoa butter, coconut oil, palm kernel oil, palm oil hard ester, or 58 degree palm oil.
  • the glyceride containing saturated fatty acid residues is palm oil hard ester.
  • Palm oil hard ester is a kind of palm oil with a high melting point (melting point 44-56 ° C.) produced during the production of edible palm oil.
  • the saturated fatty acid salt is a saturated fatty acid alkali metal salt, preferably, the saturated fatty acid salt is a saturated fatty acid sodium or a saturated fatty acid potassium.
  • the inert gas may be selected from nitrogen, neon, and argon.
  • the inert gas is nitrogen.
  • the reaction system further includes a solvent.
  • a solvent By adding a solvent to the reaction system, the reactants and reaction products can be dissolved in the solvent, which facilitates the phase flow between the reactants and has a good effect during the reaction. The mass transfer effect makes the reaction better.
  • the solvent can extract the product.
  • the solvent may be added to the reaction system together with the reactants, or may be gradually added to the reaction system during the reaction.
  • the solvent is n-hexane.
  • the amount of the solvent added is 1 to 2 times the mass of the raw material glyceride.
  • the soap in the organic phase is removed by silica gel adsorption and then concentrated.
  • the soap can be removed from the organic phase by filtration and then by adsorption on silica gel.
  • a glyceryl tripalmitate provided by some embodiments of the present application is prepared by the following preparation method: a glyceride containing a palmitic acid residue and palmitate are subjected to a catalytic reaction under the action of a non-directional lipase to obtain Glyceryl Tripalmitate.
  • the glyceride as a raw material is a triglyceride.
  • Some embodiments of the present application also provide a USU-type triglyceride, which synthesizes a USU-type triglyceride from the trisaturated fatty acid glyceride, such as OPO.
  • the method for preparing USU-type triglycerides may be to synthesize a trisaturated fatty acid glyceride with an unsaturated fatty acid or an unsaturated fatty acid glyceride under the catalysis of a sn-1,3 specific lipase to perform an enzyme at the 1st, 3rd position. Promote the directed reaction to obtain USU-type triglycerides.
  • the glyceryl tripalmitate in this example is prepared by the following method: potassium palmitate is weighed according to the palmitic acid residues of palm oil stearin, so that the palmitic acid residue in the reaction system accounts for the total fatty acid residues The ratio was 90%. 1000 g of palm oil stearin and 1000 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with potassium palmitate. After passing in nitrogen, 1 g of non-directional lipase Lipase DF "Amano" 15 was added under the conditions of a water bath temperature of 35 ° C and a rotation speed of 400 r / min, and the reaction was kept under stirring for 4 hours.
  • the supernatant of the organic phase was obtained by centrifugation, and then the soap in the organic phase was removed by adsorption with silica gel, and concentrated to obtain a pale yellow solid with a glyceryl tripalmitate content of 81.5% and a palmitic acid content at the sn-2 position of 89.5%.
  • the glyceryl tripalmitate in this example is prepared by the following method: potassium palmitate is weighed according to the palmitic acid residues of palm oil stearin, so that the palmitic acid residue in the reaction system accounts for the total fatty acid residues The ratio was 92%. 1000 g of palm oil stearin and 1200 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with potassium palmitate. After passing in nitrogen, 10 g of non-directional lipase LipaseAY30G was added to the mixture under the conditions of a water bath temperature of 50 ° C.
  • the glyceryl tripalmitate in this example is prepared by the following method: sodium palmitate is weighed according to the palmitic acid residues of palm oil stearin, so that the palmitic acid residues in the reaction system account for the total fatty acid residues. The ratio was 94%. 1000 g of palm oil stearin and 1500 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with sodium palmitate. After introducing nitrogen gas, under the conditions of a water bath temperature of 85 ° C.
  • the glyceryl tripalmitate in this example is prepared by the following method: sodium palmitate is weighed according to the palmitic acid residues of palm oil stearin, so that the palmitic acid residues in the reaction system account for the total fatty acid residues. The ratio was 94%. 1000 g of palm oil stearin and 1500 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with sodium palmitate. After introducing nitrogen gas, under the conditions of a water bath temperature of 65 ° C.
  • the glyceryl tripalmitate in this example is prepared by the following method: potassium palmitate is weighed according to the palmitic acid residues of palm oil stearin, so that the palmitic acid residue in the reaction system accounts for the total fatty acid residues The ratio was 96%. 1000 g of palm oil stearin and 2000 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with potassium palmitate.
  • the trilauric acid glyceride in this example is prepared by the following method: potassium laurate is weighed according to the amount of lauric residues in palm kernel oil, so that the ratio of lauric acid residues in the reaction system to the total fatty acid residues To 90%, put 1000 g of palm kernel oil and 1000 ml of n-hexane into a four-necked flask, heat in a water bath until dissolved, and mix with potassium laurate. After introducing nitrogen, under the conditions of a water bath temperature of 85 ° C. and a rotation speed of 400 r / min, stir to uniformity, add 80 g of non-directional lipase Novozym 435, and keep the reaction stirred for 0.5 hours.
  • the supernatant of the organic phase was obtained by centrifugation, and then the soap in the organic phase was removed by adsorption on silica gel, and concentrated to obtain a solid.
  • the content of glyceryl trilaurate was 80.5%, and the content of lauric acid at the sn-2 position was 89.4%.
  • the trilauric acid glyceride in this example is prepared by the following method: potassium laurate is weighed according to the amount of lauric residues in palm kernel oil, so that the ratio of lauric acid residues in the reaction system to the total fatty acid residues To 92%, put 1000 g of palm kernel oil and 1200 ml of n-hexane into a four-necked flask, heat in a water bath until dissolved, and mix with potassium laurate. After passing in nitrogen, 5 g of non-directional lipase Lipase DF "Amano" 15 was added under the conditions of a water bath temperature of 38 ° C and a rotation speed of 300 r / min, and the reaction was kept under stirring for 2 hours.
  • the supernatant of the organic phase was obtained by centrifugation, and then the soap in the organic phase was removed by adsorption on silica gel, and concentrated to obtain a solid.
  • the content of glyceryl trilaurate was 82.4%, and the content of lauric acid at the sn-2 position was 91.3%.
  • the trilauric acid glyceride in this example is prepared by the following method: sodium laurate is weighed according to the lauric acid residue amount of palm kernel oil, so that the ratio of lauric acid residues in the reaction system to the total fatty acid residues At 97%, put 1000 g of palm kernel oil and 2000 ml of n-hexane into a four-necked flask, heat in a water bath until dissolved, and mix with sodium laurate. After passing in nitrogen, 10 g of non-directional lipase Lipase DF "Amano" 15 was added under the conditions of a water bath temperature of 40 ° C and a rotation speed of 350 r / min, and the reaction was kept under stirring for 5 hours.
  • the supernatant of the organic phase was obtained by centrifugation, and the soap in the organic phase was removed by adsorption on silica gel.
  • the solid was obtained by concentration.
  • the glyceryl trilaurate content was 86.1%, and the lauric acid content at the sn-2 position was 95.4%.
  • Glyceryl tristearate in this example is prepared by the following method: potassium stearate is weighed according to the amount of stearic acid residues of cocoa butter, so that the stearic acid residues in the reaction system account for the total fatty acid residues The ratio of the base was 93%. 1000 g of cocoa butter and 1500 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with potassium stearate.
  • Non-directional lipase Lipase DF "Amano" 15 was added under the conditions of a water bath temperature of 40 ° C and a rotation speed of 400 r / min, and the reaction was kept under stirring for 2 hours.
  • the supernatant of the organic phase was obtained by centrifugation, and then the soap in the organic phase was removed by adsorption on silica gel, and concentrated to obtain a solid.
  • the glyceryl tristearate content was 82.3%, and the stearic acid content at the sn-2 position was 91.6%.
  • Glyceryl tristearate in this example is prepared by the following method: potassium stearate is weighed according to the amount of stearic acid residues of cocoa butter, so that the stearic acid residues in the reaction system account for the total fatty acid residues The ratio of the base was 93%. 1000 g of cocoa butter and 1500 ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and mixed with potassium stearate. After introducing nitrogen gas, under the conditions of a water bath temperature of 75 ° C.
  • the glyceryl tripalmitate in this example is prepared by the following method: potassium palmitate is weighed according to the palmitic acid residues of palm oil stearin, so that the palmitic acid residue in the reaction system accounts for the total fatty acid residues The ratio was 94%. 1,000 g of palm oil stearin was placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with potassium palmitate. After introducing nitrogen gas, under the conditions of a water bath temperature of 85 ° C. and a rotation speed of 500 r / min, stir to uniformity, add 50 g of non-directional lipase Novozym 435, and keep the reaction stirred for 1 hour.
  • This example differs from Example 5 only in that the non-directional lipase LipaseDF "Amano" 15 added is 0.5 g.
  • the content of glyceryl tripalmitate in the product obtained by the reaction was 75.4%, and the content of palmitic acid at the sn-2 position was 85.3%.
  • This example differs from Example 5 only in that the non-directional lipase LipaseDF "Amano" 15 added is 100 g.
  • the content of glyceryl tripalmitate in the reaction product was 85.2%, and the content of palmitic acid at the sn-2 position was 94.8%.
  • Example 5 The difference between this embodiment and Example 5 is that the temperature of the water bath for the catalytic reaction is 90 ° C.
  • the content of glyceryl tripalmitate in the product obtained by the reaction was 42.8%, and the content of palmitic acid at the sn-2 position was 60.8%.
  • Palmitic acid was weighed according to the amount of palmitic acid residues in palm oil, so that the ratio of palmitic acid residues in the reaction system to the total fatty acid residues was 96%, and 1000 g of palm oil stearin and 1500 ml of n-hexane were placed in four mouths.
  • a flask heat in a water bath until dissolved and mix with palmitic acid.
  • 10 g of non-directional lipase Lipase DF "Amano" 15 was added under the conditions of a water bath temperature of 40 ° C and a rotation speed of 380 r / min, and the reaction was kept under stirring for 2 hours.
  • Example 5 According to the comparison between Example 5 and Example 13, it can be seen that the non-specific lipase and the specific lipase play a good catalytic effect in the preparation method of the embodiment of the present application.
  • Example 5 By comparing Example 5 with Examples 14 and 15, it can be seen that the more the lipase is added, the smaller its iodine value is.
  • Example 5 By comparing Example 5 with Examples 16 and 17, it can be seen that if the temperature is too high and the temperature is too low, the catalytic reaction effect will be significantly deteriorated.
  • Example 1-10 By comparing Example 1-10 with Comparative Example 1-3, it can be seen that it is relative to the production of trisaturated fatty acid glycerides only by the chemical catalysis of fatty acid salts or the action of lipase.
  • the method in the embodiment of the present application The reaction conditions are mild, the side reactions are reduced, and the purity is greatly improved.

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Abstract

一种三饱和脂肪酸甘油酯(SSS型)以及1,3-二不饱和脂肪酸-2饱和脂肪酸甘油三酯(USU型)，其由以下方法制备得到：将含有饱和脂肪酸残基的甘油酯与饱和脂肪酸盐在脂肪酶的作用下进行催化反应，得到所述三饱和脂肪酸甘油酯。其中饱和脂肪酸残基和饱和脂肪酸盐中的对应的饱和脂肪酸相同，且含有饱和脂肪酸残基的甘油酯至少具有一个未与饱和脂肪酸残基结合的酯键或羟基。在甘油酯部分具有饱和脂肪酸残基的基础上，通过对应的饱和脂肪酸盐提供足够数量的饱和脂肪酸残基，并且利用脂肪酶的催化作用，使得其反应条件温和，副反应少，生成的三饱和脂肪酸甘油酯的纯度高。

Description

一种三饱和脂肪酸甘油酯以及USU型甘油三酯 技术领域
本申请涉及甘油酯合成加工技术领域，具体而言，涉及一种三饱和脂肪酸甘油酯以及USU型甘油三酯。
背景技术
三饱和脂肪酸甘油酯合成方法主要有：在化学催化剂作用下对甘油三酯进行随机酯交换以及甘油与饱和脂肪酸在高温(180℃～200℃)反应。在化学催化剂作用下对甘油三酯进行随机酯交换制备三饱和脂肪酸甘油酯的纯度不高。甘油与饱和脂肪酸在高温(180℃～200℃)反应的缺点在于反应需要高温，工艺反应条件苛刻，副反应多。
发明内容
本申请的目的在于提供一种三饱和脂肪酸甘油酯的制备方法，其能够使得到三饱和脂肪酸甘油酯的纯度高，且反应条件简单，副反应少。
本申请解决其技术问题是采用以下技术方案来实现的。
本申请提供的一种三饱和脂肪酸甘油酯的制备方法，其包括：将含有饱和脂肪酸残基的甘油酯与饱和脂肪酸盐在非定向脂肪酶的作用下进行催化反应，得到所述三饱和脂肪酸甘油酯。其中饱和脂肪酸残基和饱和脂肪酸盐中的对应的饱和脂肪酸相同，且含有饱和脂肪酸残基的甘油酯至少具有一个未与饱和脂 肪酸残基结合的酯键或羟基。
本申请还涉及一种USU型甘油三酯，其通过上述三饱和脂肪酸甘油酯为原料合成。
在甘油酯部分具有饱和脂肪酸残基的基础上，通过对应的饱和脂肪酸盐提供足够数量的饱和脂肪酸残基，并且利用非定向脂肪酶的催化作用，使得其反应条件温和，副反应少，生成的三饱和脂肪酸甘油酯的纯度高。
具体实施方式
为使本申请实施方式的目的、技术方案和优点更加清楚，下面将对本申请实施方式中的技术方案进行清楚、完整地描述。实施方式或实施例中未注明具体条件者，按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者，均为可以通过市售购买获得的常规产品。
下面对本申请实施方式的三饱和脂肪酸甘油酯以及USU型甘油三酯进行具体说明。
本申请的一些实施方式提供的一种三饱和脂肪酸甘油酯，其由以下制备方法得到：将含有饱和脂肪酸残基的甘油酯与饱和脂肪酸盐在非定向脂肪酶的作用下进行催化反应，得到三饱和脂肪酸甘油酯。
其中饱和脂肪酸残基和饱和脂肪酸盐中的对应的饱和脂肪酸相同，例如，甘油酯含有的是饱和脂肪酸残基是棕榈酸残基(不排除含有非棕榈酸残基的其他种类的饱和脂肪酸残基)，那么对应的饱和脂肪酸盐即为棕榈酸盐。并且含有饱和脂肪酸残基的甘油酯至少具有一个未与饱和脂肪酸残基结合的酯键或羟基。即作为原料的该甘油酯是甘油一酯、甘油二酯和甘油三酯中的至少一种， 且其部分酯键是和(上述所指定的)饱和脂肪酸结合得到的酯键。例如，该甘油酯可以是甘油一酯，也可以是甘油二酯，或者甘油三酯，或者甘油二酯和甘油三酯的混合物。
需要说明的是，催化反应包括酯交换反应和酯化反应，当甘油酯主要为甘油三酯时，进行的主要是酯交换反应，当甘油酯包括部分甘油二酯或甘油一酯时还存在酯化反应。
在甘油酯具有特定饱和脂肪酸残基的部分酯键的基础上，通过引入能够提供大量特定脂肪酸残基的特定脂肪酸盐，进而使得其能够在酶的催化下，发生酯交换和酯化反应，进而降低了反应条件，使得副反应少，生成的三饱和脂肪酸甘油酯的纯度高，sn-2位上饱和脂肪酸含量高。
根据一些实施方式，甘油酯与饱和脂肪酸盐的比例为以饱和脂肪酸盐为添加量，以使得反应体系中的饱和脂肪酸残基占总的脂肪酸残基的比例大于或等于90％，优选大于92％，更优选大于95％。例如，可以使得添加饱和脂肪酸盐使得反应体系中的饱和脂肪酸残基占总的脂肪酸残基的比例为91％、92％、93％、94％、95％、96％、97％或98％等。
通过该反应物比例的设置，可以使得能够充分地满足酯交换反应或酯化反应的进行，进而能够使得反应物之间能够进行充分地接触，得到纯度更高的反应产物。
根据一些实施方式，脂肪酶的添加量为甘油酯的0.05～10％，优选为0.1～8％，进一步优选的方案中，Novozym 435的添加量为4～8％或者Lipase DF“Amano”15的添加量为0.1～1％或者LipozymeTLIM的添加量为4～8％或者LipaseAY30G的添加量为0.1～1％。例如，脂肪酶的添加量可以为0.05％、0.1％、1％、2％、 3％、4％、5％、6％、7％、8％或9％。脂肪酶的添加量对反应过程有着重要的影响，其添加量过低不能够达到催化效果，其添加量过高则使得成本升高，且在一定程度上会影响反应过程中反应物之间的接触，导致反应效果不佳。因此，通过上述范围的非定向脂肪酶的添加量可以充分地达到对反应的催化作用，使得在即定的反应时间内反应进行地更加彻底。
一些实施方式中，脂肪酶包括非定向脂肪酶、定向脂肪酶中至少一种，优选地，脂肪酶为非定向脂肪酶，非定向脂肪酶是Novozym 435、Lipase DF“Amano”15、LipozymeTLIM和LipaseAY30G中的至少一种。例如，非定向脂肪酶可以为Novozym 435或Lipase DF“Amano”15，也可以Novozym 435和Lipase DF“Amano”15的混合物。优选地，非定向脂肪酶为Lipase DF“Amano”15。
根据一些实施方式，催化反应的温度为30～90℃，优选35～85℃，进一步优选地，LipozymeTLIM反应温度为65～70℃，Novozym 435反应温度为75～85℃，Lipase DF“Amano”15反应温度为35～40℃，LipaseAY30G反应温度为35～40℃；催化反应的时间为0.5～9小时，优选的反应时间为1～4小时。在该反应温度下，反应温度相对于传统的化学催化剂的反应温度比较低，其反应更加容易进行，可以通过水浴加热的方式保持反应温度恒定，水浴加热其受热比较均匀，热量传递效果好，进而使得反应更加容易进行。当然，也可以选用炉体加热等其他加热方式来维持反应温度。
根据一些实施方式，饱和脂肪酸残基和饱和脂肪酸盐中的对应的饱和脂肪酸选自棕榈酸、硬酯酸、辛酸、癸酸、月桂酸、豆蔻酸或花生酸，例如，反应物可以是含有棕榈酸残基的甘油酯和棕榈酸盐，也可以是含有硬酯酸残基的甘 油酯和硬酯酸盐，或是含有月桂酸残基的甘油酯和月桂酸盐。优选棕榈酸或硬酯酸，更优选棕榈酸。
本申请的实施方式中选择脂肪酸盐的目的在于，脂肪酸盐作为一种强碱弱酸盐，电离能力强，其脂肪酸残基活性强，提供脂肪酸残基能力远大于游离脂肪酸或脂肪酸酯，从而加快酯交换反应的速率，缩短反应时间，可以减少脂肪酶用量，降低成本。
根据一些实施方式，含有饱和脂肪酸残基的甘油酯可以是可可酯、椰子油、棕榈仁油、棕榈油硬酯或58度棕榈油。优选地，含有饱和脂肪酸残基的甘油酯为棕榈油硬酯，棕榈油硬酯是生产食用棕榈油的过程中会产生的一种高熔点(熔点44～56℃)的棕榈油。
根据一些实施方式，饱和脂肪酸盐为饱和脂肪酸碱金属盐，优选地，饱和脂肪酸盐为饱和脂肪酸钠或饱和脂肪酸钾。
根据一些实施方式，进行催化反应具体包括将含有饱和脂肪酸残基的甘油酯与饱和脂肪酸盐混合后加入脂肪酶，在通入惰性气体的条件下，进行搅拌反应。通过惰性气体的保护可以避免外界空气对其反应造成影响，并且搅拌可以使得反应物之间能够充分接触，使得反应更加充分快速。
一些实施方式中，进行反应时搅拌的转速是300～600r/min，优选400～500r/min。
一些实施方式中，惰性气体可以选择氮气、氖气、氩气等，优选地，惰性气体为氮气。
根据一些实施方式，反应体系中还包括溶剂，通过在反应体系中加入溶剂可以使得反应物和反应产物能够溶解在溶剂中，有利于反应物之间的物相流动， 起到反应过程中具有良好的传质效果，进而使得反应效果更好。同时在反应完成后，溶剂还能够对产物进行萃取。溶剂可以和反应物一起加入到反应体系中，也可以在反应过程中逐渐加入到反应体系中。一些实施方式中，溶剂为正己烷。一些实施方式中，溶剂的添加量为原料甘油酯的质量的1～2倍。
根据一些实施方式，催化反应后通过硅胶吸附去除有机相中皂，再进行浓缩。例如，在催化反应后可以进行过滤后，再通过硅胶吸附来除去有机相中的皂。
本申请的一些实施方式提供的一种三棕榈酸甘油酯，其由以下制备方法制备得到：将含有棕榈酸残基的甘油酯与棕榈酸盐在非定向脂肪酶的作用下进行催化反应，得到三棕榈酸甘油酯。其中作为原料的甘油酯为甘油三酯。
本申请的一些实施方式还提供了一种USU型甘油三酯，其由上述三饱和脂肪酸甘油酯来合成USU型甘油三酯，例如OPO。
制备USU型甘油三酯的方法可以是将制得的三饱和脂肪酸甘油酯与不饱和脂肪酸或者不饱和脂肪酸甘油酯在sn-1,3特异性脂肪酶的催化下进行Sn-1,3位酶促定向反应，制得USU型甘油三酯。
以下结合实施例对本申请的特征和性能作进一步的详细描述。
实施例1
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钾，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为90％，将棕榈油硬脂1000g及1000ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钾混合。通入氮气后，在水浴温度为35℃及转速为400r/min条件下，搅拌至均匀后加入1g非定向脂肪酶Lipase DF“Amano”15， 保温搅拌反应4小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为81.5％，sn-2位上棕榈酸含量为89.5％。
实施例2
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钾，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为92％，将棕榈油硬脂1000g及1200ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钾混合。通入氮气后，在水浴温度为50℃及转速为350r/min条件下，搅拌至均匀后加入10g非定向脂肪酶LipaseAY30G，保温搅拌反应1小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为81.8％，sn-2位上棕榈酸含量为90.6％。
实施例3
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钠，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为94％，将棕榈油硬脂1000g及1500ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钠混合。通入氮气后，在水浴温度为85℃及转速为500r/min条件下，搅拌至均匀后加入50g非定向脂肪酶Novozym 435，保温搅拌反应1.5小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为82.1％，sn-2位上棕榈酸含量为92.3％。
实施例4
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钠，以使得反应体系中的棕榈酸残基占总的脂肪酸残基 的比例为94％，将棕榈油硬脂1000g及1500ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钠混合。通入氮气后，在水浴温度为65℃及转速为400r/min条件下，搅拌至均匀后加入40g非定向脂肪酶LipozymeTLIM，保温搅拌反应2小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为84.6％，sn-2位上棕榈酸含量为93.5％。
实施例5
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钾，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为96％，将棕榈油硬脂1000g及2000ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钾混合。通入氮气后，在水浴温度为40℃及转速为380r/min条件下，搅拌至均匀后加入10g非定向脂肪酶Lipase DF“Amano”15，保温搅拌反应1.5小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为85.7％，sn-2位上棕榈酸含量为94.8％。
实施例6
本实施例中的三月桂酸甘油酯由以下方法制备得到：根据棕榈仁油的月桂酸残基量称量月桂酸钾，以使得反应体系中的月桂酸残基占总的脂肪酸残基的比例为90％，将棕榈仁油1000g及1000ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与月桂酸钾混合。通入氮气后，在水浴温度为85℃及转速为400r/min条件下，搅拌至均匀后加入80g非定向脂肪酶Novozym 435，保温搅拌反应0.5小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到固体，其三月桂酸甘油酯含量为80.5％，sn-2位上月桂酸含量为89.4％。
实施例7
本实施例中的三月桂酸甘油酯由以下方法制备得到：根据棕榈仁油的月桂酸残基量称量月桂酸钾，以使得反应体系中的月桂酸残基占总的脂肪酸残基的比例为92％，将棕榈仁油1000g及1200ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与月桂酸钾混合。通入氮气后，在水浴温度为38℃及转速为300r/min条件下，搅拌至均匀后加入5g非定向脂肪酶Lipase DF“Amano”15，保温搅拌反应2小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到固体，其三月桂酸甘油酯含量为82.4％，sn-2位上月桂酸含量为91.3％。
实施例8
本实施例中的三月桂酸甘油酯由以下方法制备得到：根据棕榈仁油的月桂酸残基量称量月桂酸钠，以使得反应体系中的月桂酸残基占总的脂肪酸残基的比例为97％，将棕榈仁油1000g及2000ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与月桂酸钠混合。通入氮气后，在水浴温度为40℃及转速为350r/min条件下，搅拌至均匀后加入10g非定向脂肪酶Lipase DF“Amano”15，保温搅拌反应5小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到固体，其三月桂酸甘油酯含量为86.1％，sn-2位上月桂酸含量为95.4％。
实施例9
本实施例中的三硬脂酸甘油酯由以下方法制备得到：根据可可脂的硬脂酸残基量称量硬脂酸钾，以使得反应体系中的硬脂酸残基占总的脂肪酸残基的比例为93％，将可可脂1000g及1500ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与硬脂酸钾混合。通入氮气后，在水浴温度为40℃及转速为400r/min条件下，搅拌至均匀后加入5g非定向脂肪酶Lipase DF“Amano”15，保温搅拌反 应2小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到固体，其三硬脂酸甘油酯含量为82.3％，sn-2位上硬酯酸含量为91.6％。
实施例10
本实施例中的三硬脂酸甘油酯由以下方法制备得到：根据可可脂的硬脂酸残基量称量硬脂酸钾，以使得反应体系中的硬脂酸残基占总的脂肪酸残基的比例为93％，将可可脂1000g及1500ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与硬脂酸钾混合。通入氮气后，在水浴温度为75℃及转速为440r/min条件下，搅拌至均匀后加入60g非定向脂肪酶Novozym 435，保温搅拌反应1小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到固体，其三硬脂酸甘油酯含量为87.3％，sn-2位上硬酯酸含量为91.3％。
实施例11
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钾，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为85％，将棕榈油硬脂1000g及2000ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钾混合。通入氮气后，在水浴温度为40℃及转速为380r/min条件下，搅拌至均匀后加入10g非定向脂肪酶Lipase DF“Amano”15，保温搅拌反应1.5小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为65.5％，sn-2位上棕榈酸含量为81.4％。
实施例12
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钾，以使得反应体系中的棕榈酸残基占总的脂肪酸残基 的比例为94％，将棕榈油硬脂1000g放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钾混合。通入氮气后，在水浴温度为85℃及转速为500r/min条件下，搅拌至均匀后加入50g非定向脂肪酶Novozym 435，保温搅拌反应1小时。用1500ml正己烷萃取后，离心得到有机相上清，用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为73.3％，sn-2位上棕榈酸含量为88.2％。
实施例13
本实施例中的三棕榈酸甘油酯由以下方法制备得到：根据棕榈油硬脂的棕榈酸残基量称量棕榈酸钾，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为96％，将棕榈油硬脂1000g及2000ml正己烷放至四口烧瓶中，水浴加热直至溶解后，与棕榈酸钾混合。通入氮气后，在水浴温度为65℃及转速为380r/min条件下，搅拌至均匀后加入60g固定化1，3位专一性脂肪酶Lipozyme RMIM，保温搅拌反应2小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为67.8％，sn-2位上棕榈酸含量为74.6％。
实施例14
本实施例与实施例5的区别仅在于，加入的非定向脂肪酶Lipase DF“Amano”15为0.5g。反应得到的产物中三棕榈酸甘油酯含量为75.4％，sn-2位上棕榈酸含量为85.3％。
实施例15
本实施例与实施例5的区别仅在于，加入的非定向脂肪酶Lipase DF“Amano”15为100g。反应得到的产物中三棕榈酸甘油酯含量为85.2％，sn-2位 上棕榈酸含量为94.8％。
实施例16
本实施例与实施例5的区别仅在于，催化反应的水浴温度为30℃。反应得到的产物中三棕榈酸甘油酯含量为65.3％，sn-2位上棕榈酸含量为80.2％。
实施例17
本实施例与实施例5的区别仅在于，催化反应的水浴温度为90℃。反应得到的产物中三棕榈酸甘油酯含量为42.8％，sn-2位上棕榈酸含量为60.8％。
对比例1
称量棕榈油硬脂30kg在100L中试反应器中，加入棕榈酸钠5kg，通氮气，加热搅拌。然后，反应温度稳定在180℃，转速为300r/min，反应12h。降至50℃，加入正己烷溶解固体，离心得到有机相上清，硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为40.7％，sn-2位上棕榈酸含量为63.6％。
对比例2
称量棕榈油硬脂30kg在100L中试反应器中，加入棕榈酸钠5kg，通氮气，加热搅拌。然后，反应温度稳定在185℃，转速为400r/min，反应20h。降至50℃，加入正己烷溶解固体，加入水吸附皂。过滤，硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为41.2％，sn-2位上棕榈酸含量为64.2％。
对比例3
根据棕榈油的棕榈酸残基量称量棕榈酸，以使得反应体系中的棕榈酸残基占总的脂肪酸残基的比例为96％，将棕榈油硬脂1000g及1500ml正己烷放至四 口烧瓶中，水浴加热直至溶解后，与棕榈酸混合。通入氮气后，在水浴温度为40℃及转速为380r/min条件下，搅拌至均匀后加入10g非定向脂肪酶Lipase DF“Amano”15，保温搅拌反应2小时。离心得到有机相上清，再用硅胶吸附除去有机相中皂，浓缩得到淡黄色固体，其三棕榈酸甘油酯含量为51.2％，sn-2位上的棕榈酸含量为78％。
通过实施例1到实施例10，可以看出通过本申请实施方式制备得到的三饱和脂肪酸甘油酯的纯度均达到80％以上，其反应条件温和，副反应少。通过对比实施例5和实施例11对比可知，饱和脂肪酸盐的添加量对得到的三饱和脂肪酸甘油酯的纯度有较大影响，当其添加量使得反应体系中的饱和脂肪酸残基占总的脂肪酸残基的比例在90％时，能够获得纯度较高的产品。通过对比实例3和实施例12可知，在反应体系中加入溶剂有利于催化反应的效果，提高产品的纯度。根据实施例5和实施例13进行比较，可以看出非定向性脂肪酶相对定向脂肪酶在本申请的实施方式的制备方法中起到很好的催化效果。通过将实施例5与实施例14和15进行对比可以看出，脂肪酶的添加量不是越多，其碘值越小。通过将实施例5与实施例16和实施例17进行比较，可以看出温度过高和温度过低，其催化反应效果均会显著变差。通过将实施例1-10与对比例1-3进行对比，可以看出其相对与仅在脂肪酸盐的化学催化或脂肪酶作用下生产得到三饱和脂肪酸甘油酯，本申请实施方式中的方法其反应条件温和、副反应减少，纯度大大提高。
综上所述，在甘油酯部分具有饱和脂肪酸残基的基础上，通过对应的饱和脂肪酸盐提供足够数量的饱和脂肪酸残基，并且利用非定向脂肪酶的催化作用，使得其反应条件温和，副反应少，进而使得生成的三饱和脂肪酸甘油酯的纯度 高。
以上所描述的实施例是本申请一部分实施例，而不是全部的实施例。本申请的实施例的详细描述并非旨在限制要求保护的本申请的范围，而是仅仅表示本申请的选定实施例。基于本申请中的实施例，本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例，都属于本申请保护的范围。

Claims (14)

  1. 一种三饱和脂肪酸甘油酯，其通过以下制备方法制备得到：
    将含有饱和脂肪酸残基的甘油酯与饱和脂肪酸盐在脂肪酶的作用下进行催化反应，得到所述三饱和脂肪酸甘油酯；
    其中所述饱和脂肪酸残基和所述饱和脂肪酸盐中的对应的饱和脂肪酸相同，且含有饱和脂肪酸残基的所述甘油酯至少具有一个未与饱和脂肪酸残基结合的酯键或羟基。
  2. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述甘油酯与所述饱和脂肪酸盐的反应体系中饱和脂肪酸残基占总的脂肪酸残基的比例大于或等于90％，优选大于92％，更优选大于95％。
  3. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述脂肪酶的添加量为所述甘油酯的0.05～10％，优选0.1～8％。
  4. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述脂肪酶为非定向脂肪酶。
  5. 根据权利要求4所述的三饱和脂肪酸甘油酯，其中，所述非定向脂肪酶是Novozym 435、Lipase DF“Amano”15、LipozymeTLIM和LipaseAY30G中的至少一种。
  6. 根据权利要求1所述的三饱和脂肪酸甘油酯的制备方法，其中，催化反应的温度为30～90℃，优选35～85℃，催化反应的时间为0.5～9小时，优选的为1～4小时。
  7. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述甘油酯是甘油一酯、甘油二酯和甘油三酯中的至少一种。
  8. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述饱和脂肪酸残基和所述饱和脂肪酸盐中的对应的饱和脂肪酸选自棕榈酸、硬酯酸、辛酸、癸 酸、月桂酸、豆蔻酸或花生酸，优选棕榈酸或硬酯酸，更优选棕榈酸。
  9. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述饱和脂肪酸盐为饱和脂肪酸碱金属盐。
  10. 根据权利要求9所述的三饱和脂肪酸甘油酯，其中，，所述饱和脂肪酸盐为饱和脂肪酸钠或饱和脂肪酸钾。
  11. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，进行催化反应具体包括将含有饱和脂肪酸残基的所述甘油酯与所述饱和脂肪酸盐混合后加入所述脂肪酶，在通入惰性气体的条件下，进行搅拌反应。
  12. 根据权利要求1所述的三饱和脂肪酸甘油酯，其中，所述反应体系中还包括溶剂。
  13. 根据权利要求12所述的三饱和脂肪酸甘油酯，其中，所述溶剂为正己烷。
  14. 一种USU型甘油三酯，其通过以如权利要求1至13中任一项所述的三饱和脂肪酸甘油酯为原料合成。
PCT/CN2019/094643 2018-07-04 2019-07-04 一种三饱和脂肪酸甘油酯以及usu型甘油三酯 WO2020007334A1 (zh)

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