CN103361387A - Production method for coproducing unsaturated monoglyceride by using diglyceride enzyme method - Google Patents
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Abstract
The invention discloses a production method for coproducing unsaturated monoglyceride by using a diglyceride enzyme method. The method comprises: (1)adding absolute ethyl alcohol into a natural grease, carrying out an alcoholysis reaction under catalysis of immobilized lipase, making the generation rate of fatty acid ethyl ester to be 5-40%w/w, and removing the residual alcohol to obtain an alcoholysis product; (2) adding 5-15%w/w of glycerin into the alcoholysis product of step (1), then reacting the above mixed substrates in a packed-bed enzyme reactor filled with immobilized lipase under a vacuum condition; and (3) performing molecular distillation on the reaction product of step (2), and separating to obtain a high-temperature fraction which is a diglyceride-containing product and a low-temperature fraction which mainly comprises monoglyceride. The reaction system of the invention needs no water, therefore the problem of product acid value is solved, and then coproduction of monoglyceride is realized; and the glycerin does not need preadsorption processing, and therefore the production operation is simplified.
Description
Technical field
The present invention relates to the unsaturated mono-glycerides of a kind of coproduction and triglyceride Production by Enzymes method.
Background technology
Natural food oils main component is triglyceride level, and triglyceride level is that a glycerine is in conjunction with the compound of three fatty acid molecules.In natural fats and oils, also have a small amount of triglyceride, triglyceride is to be connected with the compound that two molecules of fatty acids form on the glycerol molecule, the common content of the content of triglyceride in edible oil is no more than 5%.1993, Hara K reported first triglyceride have function (the Ann Nutr Metab1993 of blood fat reducing; 37:185), prompting can be used for prevention and treatment hyperlipidaemia and with the closely-related cardiovascular and cerebrovascular diseases of hyperlipidaemia.Japanese Kao company has released triglyceride type edible oil first in later 1990s, and obtains the coml success.Afterwards, studies show that more and more triglyceride has the multiple function that is conducive to HUMAN HEALTH, experimentation on animals and human body prove that all triglyceride has unique metabolic patterns, adopt triglyceride to substitute triglyceride level, can prevention of obesity, blood fat reducing.
Triglyceride as edible oil is generally unsaturated type triglyceride, and it generally is to adopt the enzymatic conversion method explained hereafter.More representative production technique is at first triglyceride level to be decomposed to obtain free fatty acids, and adopting lipase is that the catalysis instrument is so that free fatty acids and glycerine esterification reaction obtain triglyceride again.In this technique, the acquisition of lipid acid can be adopted highly pressured hydrolysis, also can adopt enzymatic hydrolysis.In the enzyme process building-up process of triglyceride, all follow a certain amount of mono-glycerides to generate, mono-glycerides also has very high using value, still, and when adopting lipid acid to be the substrate synthetic triglyceride, still there are a considerable amount of lipid acid residues, when fractionation by distillation, be difficult to lipid acid is thoroughly separated with mono-glycerides, so, be difficult to obtain the mono-glycerides product of low acid value, and the application of the mono-glycerides of high acid value is very limited.
Glycerine solution technique is the another kind of important method of producing triglyceride, the method is take triglyceride level as substrate, do not need to add free fatty acids in the reaction process, therefore, avoid lipid acid and the problem that mono-glycerides is difficult to separate in the above-mentioned technique, when producing triglyceride, obtained the lower mono-glycerides product of acid value.Because glycerine has package action to enzyme, for addressing this problem, patent CN200310112327.X adopts the glycerine of carrier adsorption form as substrate, so that reaction is carried out in these class methods.Practice is found, although the glycerine of adsorption form can overcome the defective that free glycerol is difficult to react, but still exists low the regeneration with carrier of reaction efficiency to use inconvenient shortcoming, and the difficulty of industrialized implementation is very large.
Summary of the invention
The object of the invention is to the shortcoming for the prior art existence, the triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction is provided.It is substrate that the method adopts the triglyceride type grease, at first carries out the ethanolysis reaction, obtains reaction product, adds free glycerol in reaction product, carries out the enzyme process glycerolysis reaction, can obtain the unsaturated mono-glycerides of low acid value when obtaining triglyceride.
The triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction may further comprise the steps:
(1) in natural fats and oils, adds dehydrated alcohol, under fixed lipase catalyzed, carry out the ethanolysis reaction, so that the fatty-acid ethyl ester production rate is 5～40%w/w, remove residue ethanol, obtain alcoholysis product;
(2) add the glycerine of 5～15%w/w in step (1) alcoholysis product, then with above-mentioned mixed substrates in the packed bed enzyme reactor of immobilized lipase is housed, under vacuum condition, react;
(3) step (2) reaction product is through molecular distillation, and separating the high temperature cut that obtains is the product that contains triglyceride, obtains simultaneously take mono-glycerides as main low temperature fraction.
Pressure segmentation control is adopted in the described reaction of step (2), before the reaction, reacts certain hour first under normal pressure under vacuum condition; Wherein the synthesis under normal pressure time length is 1/4～1/3 of the vacuum reaction time.
The condition of the described vacuum reaction of step (2): pounds per square inch absolute (psia) is 10～1000pa.
The described temperature of reaction of step (2) is 50 ℃～60 ℃.
The add-on of the described glycerine of step (2) is 8～12%w/w.
The consumption of the described immobilized lipase of step (2) is 0.2～5% of substrate weight, and the vacuum reaction time length is 3～24 hours.
The described molecular distillation of step (3) adopts three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 80～120 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 150～180 ℃; Third stage separation obtains target product, and distillation temperature is 190～220 ℃.
Immobilized lipase of the present invention is one or more the mixture that derives from root enzyme genus, Aspergillus, hair enzyme genus, bacterium, yeast and the steapsase.Be preferably lipase Novozym435, Lipozyme RM IM or Lipozyme TL IM.
Described natural fats and oils is animal grease or Vegetable oil lipoprotein.
Described Vegetable oil lipoprotein is one or more the mixture in soybean oil, rapeseed oil, Semen Maydis oil, plam oil, peanut oil, sunflower seed oil, Camellia oil, sweet oil and the Rice pollard oil; Animal grease is one or more the mixture in fish oil, lard, butter and the chicken fat.
Step of the present invention (1) is the enzyme process ethanolysis reaction of grease, and reaction product is fatty-acid ethyl ester.The enzyme process ethanolysis of grease is a process that simply is easy to realize.The ethanolysis of grease normally mixes dehydrated alcohol and grease, then add immobilized lipase and stir, perhaps with reaction substrate by the pillar of immobilized lipase is housed, the reaction certain hour can obtain reaction product.The enzyme process ethanolysis temperature of reaction of grease can be set flexibly according to the tolerable temperature of lipase, is generally 20～60 ℃; The addition of reaction times and enzyme is relevant.In the present invention, by add-on and the control extent of reaction of reasonable computation ethanol, the production rate of control ethyl ester is 5～40%(w/w), and namely the amount of ethyl ester accounts for 5～40%(w/w) of reaction product in the reaction product.
Step of the present invention (2) is glycerolysis reaction, is committed step of the present invention.As previously mentioned, the invention is characterized in that the employing free glycerol carries out the glycerine solution.In the present invention, directly in step (1) reaction product, add 5～15%(w/w) glycerine, then with this reaction substrate by the packed bed enzyme reactor of immobilized lipase is housed, catalysis is to react under the vacuum condition of 10～1000pa in absolute pressure.In this step, the addition of glycerine is 5～15%(w/w), and namely the glycerine addition is 5～15%, preferred 8～12% of step (1) reaction product weight.Very few glycerine addition can affect the growing amount of partial glyceride (partial glyceride is the general designation of triglyceride and mono-glycerides), and too much glycerine addition is unnecessary, and superfluous glycerine still tends to be gathered in the zymin top layer, affects speed of response.Among the present invention, the interpolation of glycerine can be once to add, the mode that also can take stream to add, and the mode that adds of preferred streams.Step of the present invention (2) is particularly limited and will adopts the filling bed type enzyme reactor, and with respect to stirring-type enzyme reactor in batches, the filling bed type enzyme reactor has better substrate mass-transfer performance, the efficient catalytic of easier realization enzyme.The feature of step of the present invention (2) reaction is that also catalyzed reaction is to carry out under absolute pressure is the vacuum condition of 10～1000pa, vacuum condition can remove the residual ethanol of reaction substrate and micro-moisture, in addition, vacuum condition impels also that the part ethyl ester is converted into triglyceride in the reaction system.Among the present invention, the pressure-controlling of step (2) reaction also can be carried out in segmentation, at first is synthesis under normal pressure, after synthesis under normal pressure carries out certain hour (be about vacuum reaction time 1/4～1/3), forwarding vacuum reaction to, is to carry out under the vacuum condition of 10～1000pa in absolute pressure again.The consumption of step (2) reaction times and enzyme is relevant, and usually, the consumption of immobilized enzyme is 0.2～5% of substrate weight, and the reaction times is 3～24 hours.Passed through step (2) reaction, the triglyceride level major part in the reactive system is converted into partial glyceride, and the weight ratio of mono-glycerides and triglyceride is about 1:4～8 in the partial glyceride usually.
Step (3) is separation phase, step (2) reaction product mainly comprises triglyceride level, triglyceride, mono-glycerides, fatty-acid ethyl ester, glycerine, usually triglyceride and mono-glycerides are as the purpose product, and the purpose of separation is to obtain relatively pure triglyceride and mono-glycerides.Separation method commonly used is molecular distillation, and the characteristics of these class methods are under vacuum condition, can separate needed temperature by decrease.Molecular distillation and short-path distillation separation method are class separation unit operation commonly used, and the present invention distills flow process can adopt three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 80～120 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 150～180 ℃; Third stage separation obtains the high temperature cut as leading take triglyceride and triglyceride level, obtains simultaneously take mono-glycerides as main low temperature fraction, and distillation temperature is 190～220 ℃.In the present invention, triglyceride and triglyceride level are to mix as the high temperature cut to exist, and contain the product of triglyceride among the present invention, are the mixture of triglyceride and triglyceride level.
Among the present invention, owing to there is not the participation of water, the free fatty acid content in the stages enzyme reaction thing is very low, and main component is mono-glycerides in the mono-glycerides product that separation obtains through step (3), and free fatty acid content is lower than 1.5%; The high temperature cut part of step (3), free fatty acid content is lower than 0.5%.Because step (3) high temperature cut is as target product, for further improving quality standard, still needs further refining treatment.Among the present invention, step (3) high temperature cut needs further to process through decolouring and deodorization, and this two workshop section is edible oil processing common processes.The discoloring agent of the general employing 1.5% of decolouring is processed, and discoloring agent is the mixture of atlapulgite and gac 20:1.Deodorization is to adopt the wet distillation method to remove the bad flavor of fat residue.
This research team carries out the glycerolysis reaction of grease for a long time, research finds that adopting triglyceride level and glycerine is that substrate reacts, when having free glycerol in the reaction system, free glycerol is understood preferential and zymin is wrapped up effect in conjunction with forming, and causes the apparent inactivation of enzyme.For addressing this problem, glycerine must adopt carrier to carry out preadsorption and process.Further research is found, fatty-acid ethyl ester is made an addition in the reaction system of triglyceride level and free glycerol, enzyme reactor adopts fixed-bed reactor, the reaction substrate mixture is forced constantly to cycle through the fixed bed enzyme reactor, at this moment, although do not adopt the glycerine of ADSORPTION STATE, reaction still can be carried out smoothly.Show that the parcel effect of glycerine to zymin alleviated in the interpolation of fatty-acid ethyl ester, so that the glycerolysis reaction take free glycerol as substrate is achieved.Because reaction process of the present invention does not have the participation of water, has avoided the generation of free fatty acids, thereby can produce the reaction product of low acid value, obtain beyond thought effect, and then formed the present invention.
Compare with existing technology, the technology of the present invention has the following advantages:
Reaction system of the present invention does not need to add water, has solved product acid value problem, thereby can the coproduction mono-glycerides; Do not process because glycerine does not need to do preadsorption, simplified production operation.
Description of drawings
Fig. 1 is the device of enzyme process glycerolysis reaction of the present invention, raw material storage tank 1, pump 2, packed bed enzyme reactor 3.
Embodiment
The invention will be further described below in conjunction with embodiment, and all % content are not done special instruction among the embodiment, all are weight percentage.
The triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction may further comprise the steps:
Step (1), 5kg soybean oil and 0.3kg dehydrated alcohol mix, adding immobilized lipase Novozyme 435(Denmark Novozymes company provides) 2g, 35 ℃ of stirring reactions 3 hours, surveying the fatty-acid ethyl ester production rate is 20.6%, and the vacuum removal residual ethanol obtains alcoholysis product.
Step (2), alcoholysis product 3kg packs in as shown in Figure 1 the raw material storage tank 1, add 0.3kg glycerine, material cycles through the packed bed enzyme reactor 3 of immobilized lipase under pump 2 effects, and temperature of reaction is 60 ℃, adopt immobilized lipase Novozyme 435, the amount of fill of enzyme is 10g, and reaction is 1 hour under normal pressure, then will react absolute pressure and be controlled to be 10pa, react again discharging after 3 hours, analyze its composition and see Table 1.
Step (3), reaction product is separated through molecular distillation, and the present invention distills flow process can adopt three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 110 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 175 ℃; Third stage separation obtains the high temperature cut as leading take triglyceride and triglyceride level, obtains simultaneously take mono-glycerides as main low temperature fraction, and distillation temperature is 210 ℃.High temperature cut and low temperature fraction analytical results table 1.
The triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction may further comprise the steps:
Step (1), 5kg soybean oil and 0.3kg dehydrated alcohol mix, adding immobilized lipase Novozyme 435(Denmark Novozymes company provides) 2g, 35 ℃ of stirring reactions 0.5 hour, surveying the ethyl ester production rate is 9.8%, and the vacuum removal residual ethanol obtains alcoholysis product.
Step (2), alcoholysis product 3kg packs in as shown in Figure 1 the raw material storage tank, add 0.15kg glycerine, material cycles through the packed bed enzyme reactor of immobilized lipase under pumping action, and temperature of reaction is 60 ℃, adopt immobilized lipase Novozyme 435, the amount of fill of enzyme is 10g, at first reacts 6 hours under normal pressure, then reacts absolute pressure and is controlled to be 100pa, react discharging after 24 hours, analyze its composition and see Table 1.
Step (3), reaction product is separated through molecular distillation, and the present invention distills flow process can adopt three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 110 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 175 ℃; Third stage separation obtains the high temperature cut as leading take triglyceride and triglyceride level, obtains simultaneously take mono-glycerides as main low temperature fraction, and distillation temperature is 210 ℃.High temperature cut and low temperature fraction analytical results table 1.
The triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction may further comprise the steps:
Step (1), 5kg soybean oil and 0.3kg dehydrated alcohol mix, adding immobilized lipase Novozyme 435(Denmark Novozymes company provides) 2g, 35 ℃ of stirring reactions 5 hours, surveying the ethyl ester production rate is 31.2%, and the vacuum removal residual ethanol obtains alcoholysis product.
Step (2), alcoholysis product 3kg packs in as shown in Figure 1 the raw material storage tank, add 0.45kg glycerine, material cycles through the packed bed enzyme reactor of immobilized lipase under pumping action, and temperature of reaction is 60 ℃, adopt immobilized lipase Novozyme 435, the amount of fill of enzyme is 10g, at first reacts 3 hours under normal pressure, then reacts absolute pressure and is controlled to be 200pa, react discharging after 12 hours, analyze its composition and see Table 1.
Step (3), reaction product is separated through molecular distillation, and the present invention distills flow process can adopt three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 110 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 175 ℃; Third stage separation obtains the high temperature cut as leading take triglyceride and triglyceride level, obtains simultaneously take mono-glycerides as main low temperature fraction, and distillation temperature is 210 ℃.High temperature cut and low temperature fraction analytical results table 1.
Embodiment 4
The triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction may further comprise the steps:
Step (1), 5kg soybean oil and 0.3kg dehydrated alcohol mix, adding immobilized lipase Novozyme 435(Denmark Novozymes company provides) 2g, 30 ℃ of stirring reactions 3 hours, surveying the ethyl ester production rate is 18.3%, and the vacuum removal residual ethanol obtains alcoholysis product.
Step (2), alcoholysis product 3kg packs in as shown in Figure 1 the raw material storage tank, add 0.2kg glycerine, material cycles through the packed bed enzyme reactor of immobilized lipase under pumping action, and temperature of reaction is 60 ℃, adopt immobilized lipase Novozyme 435, the amount of fill of enzyme is 10g, at first reacts 2 hours under normal pressure, then reacts absolute pressure and is controlled to be 1000pa, react discharging after 8 hours, analyze its composition and see Table 1.
Step (3), reaction product is separated through molecular distillation, and the present invention distills flow process can adopt three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 110 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 175 ℃; Third stage separation obtains the high temperature cut as leading take triglyceride and triglyceride level, obtains simultaneously take mono-glycerides as main low temperature fraction, and distillation temperature is 210 ℃.High temperature cut and low temperature fraction analytical results table 1.
Embodiment 5
The triglyceride Production by Enzymes method of the unsaturated mono-glycerides of a kind of coproduction may further comprise the steps:
Step (1), 5kg soybean oil and 0.3kg dehydrated alcohol mix, adding immobilized lipase Novozyme 435(Denmark Novozymes company provides) 2g, 35 ℃ of stirring reactions 3 hours, surveying the ethyl ester production rate is 22.3%, and the vacuum removal residual ethanol obtains alcoholysis product.
Step (2), alcoholysis product 3kg packs in as shown in Figure 1 the raw material storage tank, add 0.3kg glycerine, material cycles through the packed bed enzyme reactor of immobilized lipase under pumping action, and temperature of reaction is 60 ℃, adopt immobilized lipase Novozyme 435, the amount of fill of enzyme is 10g, at first reacts 3 hours under normal pressure, then reacts absolute pressure and is controlled to be 100pa, react discharging after 12 hours, analyze its composition and see Table 1.
Step (3), reaction product is separated through molecular distillation, and the present invention distills flow process can adopt three-stage distillation, and the first step is degassed and take off glycerine, and distillation temperature is 110 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 175 ℃; Third stage separation obtains the high temperature cut as leading take triglyceride and triglyceride level, obtains simultaneously take mono-glycerides as main low temperature fraction, and distillation temperature is 210 ℃.High temperature cut and low temperature fraction analytical results table 1.
The comparative example
3kg soybean oil raw material is packed in as shown in Figure 1 the raw material storage tank, add 0.15kg glycerine, material cycles through the packed bed enzyme reactor of immobilized lipase under pumping action, temperature of reaction is 60 ℃, adopts immobilized lipase Novozyme 435, and the amount of fill of enzyme is 10g, at first under normal pressure, reacted 3 hours, then react absolute pressure and be controlled to be 100pa, react discharging after 12 hours, glycerine hydrolysis products analytical results sees Table 1.
Table 1
By table 1 result as seen, the comparative example directly adopts soybean oil to carry out enzyme process glycerine solution, and glycerolysis reaction does not almost occur.Embodiment 1 to embodiment 5 is again glycerine solution of first ethanolysis, and reaction then can be carried out smoothly, can obtain to comprise the grease of triglyceride, obtains simultaneously the mono-glycerides product of low acid value.
Claims (10)
1. the triglyceride Production by Enzymes method of the unsaturated mono-glycerides of coproduction is characterized in that, may further comprise the steps:
(1) in natural fats and oils, adds dehydrated alcohol, under fixed lipase catalyzed, carry out the ethanolysis reaction, so that the fatty-acid ethyl ester production rate is 5～40%w/w, remove residue ethanol, obtain alcoholysis product;
(2) add the glycerine of 5～15%w/w in step (1) alcoholysis product, then with above-mentioned mixed substrates in the packed bed enzyme reactor of immobilized lipase is housed, under vacuum condition, react;
(3) step (2) reaction product is through molecular distillation, and separating the high temperature cut that obtains is the product that contains triglyceride, obtains simultaneously take mono-glycerides as main low temperature fraction.
2. method according to claim 1 is characterized in that, pressure segmentation control is adopted in the described reaction of step (2), before the reaction, reacts certain hour first under normal pressure under vacuum condition; Wherein the synthesis under normal pressure time length is 1/4～1/3 of the vacuum reaction time.
3. method according to claim 2 is characterized in that, the condition of described vacuum reaction: pounds per square inch absolute (psia) is 10～1000pa.
4. method according to claim 3 is characterized in that, the described temperature of reaction of step (2) is 50 ℃～60 ℃.
5. according to claim 1 and 2 or 3 or 4 described methods, it is characterized in that the add-on of described glycerine is 8～12%w/w.
6. according to claim 1 and 2 or 3 or 4 described methods, it is characterized in that the consumption of the described immobilized lipase of step (2) is 0.2～5% of substrate weight, the vacuum reaction time length is 3～24 hours.
7. according to claim 1 and 2 or 3 or 4 described methods, it is characterized in that described molecular distillation adopts three-stage distillation, the first step is degassed and take off glycerine, and distillation temperature is 80～120 ℃; The second stage removes fatty-acid ethyl ester, and distillation temperature is 150～180 ℃; Third stage separation obtains target product, and distillation temperature is 190～220 ℃.
8. according to claim 1 and 2 or 3 or 4 described methods, it is characterized in that described immobilized lipase is lipase Novozym435, Lipozyme RM IM or Lipozyme TL IM.
9. according to claim 1 and 2 or 3 or 4 described methods, it is characterized in that described natural fats and oils is animal grease or Vegetable oil lipoprotein.
10. method according to claim 9 is characterized in that, described Vegetable oil lipoprotein is one or more the mixture in soybean oil, rapeseed oil, Semen Maydis oil, plam oil, peanut oil, sunflower seed oil, Camellia oil, sweet oil and the Rice pollard oil; Animal grease is one or more the mixture in fish oil, lard, butter and the chicken fat.
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