CN105671094A - Enzymatic preparation method of propylene glycol fatty acid monoester - Google Patents
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Abstract
The invention discloses an enzymatic preparation method of propylene glycol fatty acid monoester. The method comprises the following steps: (1) fetching fatty acid and heating to melt the fatty acid into a liquid state, adding propylene glycol and performing homogenization treatment to obtain an esterification reaction substrate; (2) enabling partial glyceride lipase to contact with the esterification reaction substrate, adding a buffer solution with pH of 4-8, and stirring for an esterification reaction to synthesize propylene glycol monoester; and (3) separating the reaction product, recycling the oil phase and separating and purifying the oil phase to obtain high-purity propylene glycol monoester. In the invention, the partial glyceride lipase catalyzes the esterification of fatty acid and propylene glycol to synthesize propylene glycol monoester, no side reaction occurs in the reaction process, the esterification rate of fatty acid is high, and the substrate is utilized more effectively; the yield and purity of propylene glycol monoester are higher, and the yield is more than or equal to 90%; and after molecular distillation separation and purification, the purity of propylene glycol fatty acid monoester is more than or equal to 98%.
Description
Technical field
The present invention relates to the enzymatic-process preparation method of a kind of propylene glycol fatty acid monoester.
Background technology
Propylene glycol fatty acid monoester, is the monoesters formed by a fatty acid acyl and propylene glycol, has good lipophile and defoaming. From eighties of last century the fifties, namely propylene glycol fatty acid monoester has become as widely used food additive, is the nonionic surfactant of a kind of function admirable. Namely patent CN103533845A discloses a kind of compositions being main component with propylene glycol fatty acid monoester, for controlling foaming degree during food system heating. In food, propylene glycol fatty acid monoester is general with other emulsifying agent compound uses, in the food such as cake, bread, margarine, chocolate, has emulsifying, shortening, fresh-keeping, froth breaking etc. and acts on. In medicine, propylene glycol fatty acid monoester can as stabilizer, emulsifying agent in the medicament such as Emulsion and ointment.
Propylene glycol fatty acid monoester preparation method has the alcoholysis method of fatty acid, propylene glycol direct esterification, fatty acid and propylene oxide reaction method and propylene glycol and animal and plant fat. The propylene glycol fatty acid monoester of food stage, is generally adopted fatty acid and produces with propylene glycol direct esterification. At present, the propylene glycol monoester in commercial production, it is mostly to utilize the chemical catalysts such as acid, alkali, is esterified at 120～180 DEG C of catalysis propylene glycol and satisfied fatty acid, obtains the mixture of propylene glycol monoester and diester. In chemical catalysis process, owing to there is pyroprocess, fatty acid can only select the better satisfied fatty acid of stability, and the yield of propylene glycol monoester generally can only achieve 70%, need, then through molecular distillation separation purification, just to obtain the propylene glycol monoester product (paper: the chemical analysis of total monoester content in food additive methyl glycol fatty acid ester) that quality is better, purity is higher. Along with people's raising to food safety and food material processing technique attention degree, increasing research starts to explore the enzymatic production process of the propylene glycol monoester of more safe and environment-friendly, low energy consumption.Lipase is also referred to as fatty acid acyl GEH, and the application in grease processing technique is more and more extensive. Lipase from Aspergillus Niger catalysis fatty acid (stearic acid, palmitic acid, oleic acid, myristic acid, lauric acid) reacts with propylene glycol, the content (in esterification reaction product the yield of propylene glycol monoester) of the propylene glycol fatty acid monoester in esterification products can reach 21.3～63.5%, repeatedly can reach 97% (enzymatic clarification of different fatty acid propylene glycol monoesters and Nature comparison) after extraction separation purification. Lipase Novozym435 is catalysis lauric acid and propylene glycol reaction in normal hexane system, and esterification yield can reach 90.16%, and the purity of propylene glycol monoester can reach 81.37%, and in esterification products, the yield of propylene glycol monoester is 73.36%; In solvent-free system catalysis lauric acid with esterified prepare propylene glycol monoester time, esterification yield can reach 90.29%, the purity of propylene glycol monoester can reach 78.22%, and in esterification reaction product, the yield of propylene glycol monoester is 70.62% (enzymatic clarification lauric acid propylene glycol ester and character research thereof). Lipase Novozym435 catalysis oleic acid in solvent-free system reacts with propylene glycol, and the esterification yield of oleic acid can reach 89.64%, and the purity of propylene glycol monoester reaches 48.21%, and in esterification reaction product, the yield of propylene glycol monoester is 43.21%; In the reaction system that the tert-butyl alcohol is solvent, the esterification yield of oleic acid can reach 91.15%, the purity of propylene glycol monoester reaches 88.34%, in esterification reaction product, the yield of propylene glycol monoester is 80.52% (enzymatic clarification of single oleic acid 1,3 propylene glycol ester, separation purification and character research). Lipase Novozym435 catalysis propylene glycol and Oleum Cocois carry out alcoholysis reaction, and in product, the yield of propylene glycol monoester is 53.17% (enzymatic clarification Cortex cocois radicis oil base propylene glycol monoester and character research thereof). In summary, in the enzymatic-process preparation method of the propylene glycol monoester developed at present, owing to there is the by-product such as propylene glycol ester, glyceride, the yield of propylene glycol monoester and the purity of product are all extremely limited.
Summary of the invention
For the shortcoming that in the propylene glycol monoester product that existing enzymatic clarification propylene glycol fatty acid monoester method obtains, monoesters purity is not high, yield is relatively low, it is an object of the invention to provide the Production by Enzymes preparation method of a kind of high-purity propylene glycol fatty acid monoester. In the present invention, restrictively only being linked a fatty acid acyl on the hydroxyl of propylene glycol by partial glyceride lipase, in esterification products, the yield of propylene glycol monoester is higher; And, the purity of the propylene glycol fatty acid monoester product obtained after the separated recovery of product is the highest can reach more than 98%.
The present invention for achieving the above object, is achieved through the following technical solutions:
The enzymatic-process preparation method of a kind of propylene glycol fatty acid monoester, comprises the steps:
(1) take fatty acid and intensification makes it melt to be in liquid, then add propylene glycol and homogenizing processes, as esterification substrate (being cooled to 35 DEG C～65 DEG C);
(2) partial glyceride lipase and esterification substrate contact, adding pH is the buffer of 4～8, and stirring carries out esterification synthesizing propanediol fatty-acid monoester;
(3) reaction product isolated, reclaims oil phase, oil phase is easily separated purification and namely obtains highly purified propylene glycol fatty acid monoester.
The carbon number of step (1) described fatty acid is between 2～22.
The mol ratio of step (1) described propylene glycol and fatty acid is 2:1～6:1.
The mol ratio of step (1) described propylene glycol and fatty acid is at 3:1～4:1.
The addition of described partial glyceride lipase is the 0.5%～10% of fatty acid quality.
The addition of step (2) described buffer is not higher than the 1% of propylene glycol quality.
Step (2) described buffer is phosphate buffer, and pH is 5～7.
The temperature of step (2) described esterification is 20 DEG C～65 DEG C, more than stirring condition 200rpm, response time 12～24h.
The temperature of step (2) described esterification is 40 DEG C～65 DEG C.
Step is separated into centrifugation described in (2), and temperature of charge is below 40 DEG C.
It is catalysis monoglyceride and diglyceride to react with hydroxyl donor that described restrictively catalysis fatty acid and esterified reaction generate the partial glyceride lipase that uses of propylene glycol fatty acid monoester, it is impossible to the reaction of catalyzing glycerol three ester.
Described partial glyceride lipase includes deriving from monoglyceride lipase or the diglyceride lipase of the fatty tissue of animal organ (small intestinal or pig such as rat), deriving from Bacillussp.H-257 (J.Biochem., 127,419-425,2000) monoglyceride lipase, PenicilliumcamembertiiU-150 (Journaloffermentationandbioengineering is derived from, 72 (3), diglyceride lipase 162-167,1991) and the diglyceride lipase LipaseSMG1 deriving from Malasseziaglobosa.
The separation of product of the present invention is to utilize centrifugal method to separate and recover unreacted propylene glycol and catalyst, separating purification propylene glycol monoester process from oil phase can be molecular distillation, solvent extraction, alkali neutralization, it is also possible to be the associating of more than one above-mentioned separation methods.
This seminar has carried out big quantity research in the enzyme process preparation field of propylene glycol monoester, the present invention studies discovery partial glyceride lipase and catalysis fatty acid and propylene glycol can carry out esterification and prepare propylene glycol monoester, is absent from propylene glycol diesters in the esterification products obtained. Being additionally, since propylene glycol viscosity relatively big, fatty acid is poor with the intersolubility of propylene glycol, significantly limit the mass-transfer efficiency in esterification reaction process so that the esterification yield of fatty acid is low. The present invention, after fatty acid heating to fusing, and mixed with propylene glycol more than twice molal quantity, it is then passed through homogenizing and contacts with partial glyceride lipase again and carry out esterification, improve the yield of esterification yield and propylene glycol monoester.
Compared with prior art, the beneficial effects of the present invention is:
(1) present invention adopts inclined glycerin fatty enzyme catalysis fatty acid and esterified synthesizing propanediol monoesters, does not have side reaction to occur in course of reaction, and fatty acid ester rate is high, and substrate obtains more effective utilization.
(2) this method utilizes partial glyceride lipase for catalyst, by the control to esterification system moisture, improve purity and the yield of propylene glycol fatty acid monoester, in esterification products, the yield of propylene glycol fatty acid monoester is more than 90%, after molecular distillation separation purification, the purity of propylene glycol fatty acid monoester is more than 98%, it is possible to selecting different fatty acids according to specific needs is substrate.
(3) this method is due to before lipase-catalyzed esterification reacts, substrate mixture is carried out homogenizing process, esterification more rapid can be carried out, shorten esterification and reach the time that balance is required, there is better economy and the feature of environmental protection in actual applications.
Detailed description of the invention
Introduce the enforcement of the present invention by the following examples in more detail.In the described embodiment, all percentage ratios are all in mass.
Embodiment 1
280g soya fatty acid and 230g propylene glycol (mol ratio of propylene glycol and fatty acid is 3:1) heating, to 40 DEG C, are utilized high speed dispersion homogenizer homogenizing 1min; Add pH be 6.0, the phosphate buffer 2g of ion concentration 0.1N, with 10g partial glyceride lipase LipaseSMG1 (WangW-f, LiT, QinX-l, NingZ-x, YangB, WangY-h.ProductionoflipaseSMG1anditsapplicationinsynthes izingdiacylglyecrol [J] .JournalofMolecularCatalysisB:Enzymatic2012; 77:87-91), mixing is placed in the constant temperature blender with magnetic force of 400rpm and carries out esterification, reaction temperature 40 DEG C. Sampling every 1h, the acidity of titration esterification products, after esterification carries out 18h, the acid value of reaction system is reduced to 17.1mgKOH/g, continues reaction acid value and reduces not notable, it was shown that esterification has reached balance. Terminate reaction and be centrifuged esterification products separating, reclaiming oil phase and unreacted propylene glycol and catalyst. Utilizing liquid-phase chromatographic analysis oil phase to form, calculate the yield of propylene glycol fatty acid monoester, result is in Table 1. After visible esterification 18h, the yield of propylene glycol fatty acid monoester can reach more than 91.5%.
Oil phase is reclaimed in esterification products centrifugation and utilizes the propylene glycol fatty acid monoester in secondary molecules separated purification esterification products oil phase. The charging flow velocity of molecular distillation is 1.0mL/min, and one-level evaporating temperature is 100 DEG C, and dual evaporation temperature is 150 DEG C, and injector temperature is 90 DEG C, and condensation temperature is 60 DEG C, it is possible to obtain the propylene glycol fatty acid monoester that purity is 99.35%.
Embodiment 2
280g soya fatty acid and 306g propylene glycol (mol ratio of propylene glycol/fatty acid is 4:1) are heated to 40 DEG C, utilizes high speed dispersion homogenizer homogenizing 1min; Add pH be 6.0, the phosphate buffer 3g of ion concentration 0.1N, and 15g partial glyceride lipase LipaseSMG1, mixing is placed in the constant temperature blender with magnetic force of 400rpm and carries out esterification, reaction temperature 35 DEG C. Sampling every 1h, the acidity of titration esterification products, after esterification carries out 12h, the acid value of reaction system is reduced to 13.2mgKOH/g, continues reaction acid value and reduces not notable, it was shown that esterification has reached balance. Terminate reaction and be centrifuged esterification products separating, reclaiming oil phase and unreacted propylene glycol and catalyst. Utilizing liquid-phase chromatographic analysis oil phase to form, calculate the yield of propylene glycol fatty acid monoester, result is in Table 1. Basically reaching balance after visible esterification 12h, the yield of propylene glycol fatty acid monoester can reach more than 93.4%.
Esterification products centrifugation is reclaimed oil phase and unreacted propylene glycol and catalyst, utilizes the propylene glycol fatty acid monoester in secondary molecules separated purification esterification products oil phase. The charging flow velocity of molecular distillation is 1.0mL/min, and one-level evaporating temperature is 100 DEG C, and dual evaporation temperature is 150 DEG C, and injector temperature is 90 DEG C, and condensation temperature is 60 DEG C, it is possible to obtain the propylene glycol fatty acid monoester that purity is 99.6%.
Embodiment 3
280g soya fatty acid and 306g propylene glycol (mol ratio of propylene glycol/fatty acid is 4:1) are heated to 40 DEG C, utilizes high speed dispersion homogenizer homogenizing 1min; Add pH be 6.0, the phosphate buffer 3g of ion concentration 0.1N, and 15g partial glyceride lipase LipaseG50, mixing is placed in the constant temperature blender with magnetic force of 400rpm and carries out esterification, reaction temperature 40 DEG C.Sampling every 1h, the acidity of titration esterification products, after esterification carries out 18h, the acid value of reaction system is reduced to 16.5mgKOH/g, continues reaction acid value and reduces not notable, it was shown that esterification has reached balance. Terminate reaction and be centrifuged esterification products separating, reclaiming oil phase and unreacted propylene glycol and catalyst. Utilizing liquid-phase chromatographic analysis oil phase to form, calculate the yield of propylene glycol fatty acid monoester, result is in Table 1. Basically reaching balance after visible esterification 18h, the yield of propylene glycol fatty acid monoester can reach more than 91.8%.
Esterification products centrifugation is reclaimed oil phase and unreacted propylene glycol and catalyst, utilizes the propylene glycol fatty acid monoester in secondary molecules separated purification esterification products oil phase. The charging flow velocity of molecular distillation is 1.0mL/min, and one-level evaporating temperature is 100 DEG C, and dual evaporation temperature is 150 DEG C, and injector temperature is 90 DEG C, and condensation temperature is 60 DEG C, it is possible to obtain the propylene glycol fatty acid monoester that purity is 98.35%.
Comparative example 1
280g soya fatty acid and 306g propylene glycol (mol ratio of propylene glycol/fatty acid is 4:1) are heated to 40 DEG C, utilizes high speed dispersion homogenizer homogenizing 1min; Add pH be 6.0, the phosphate buffer 3g of ion concentration 0.1N, and 15g lipase LipaseCALB, mixing is placed in 400rpm, the constant temperature blender with magnetic force of 40 DEG C and carries out esterification. Sampling every 1h, the acidity of titration esterification products, after esterification carries out 18h, the acid value of reaction system is reduced to 20.5mgKOH/g, continues reaction acid value and reduces not notable, it was shown that esterification has reached balance. Terminate reaction and be centrifuged esterification products separating, reclaiming oil phase and unreacted propylene glycol and catalyst. Utilizing liquid-phase chromatographic analysis oil phase to form, calculate the yield of propylene glycol fatty acid monoester, result is in Table 1. Basically reaching balance after visible esterification 18h, the yield of propylene glycol fatty acid monoester is 52.8%, and the content of propylene glycol diesters is 36.9%.
Esterification products centrifugation is reclaimed oil phase and unreacted propylene glycol and catalyst, utilizes the propylene glycol fatty acid monoester in secondary molecules separated purification esterification products oil phase. The charging flow velocity of molecular distillation is 1.0mL/min, and one-level evaporating temperature is 100 DEG C, and dual evaporation temperature is 150 DEG C, and injector temperature is 90 DEG C, and condensation temperature is 60 DEG C, and the purity of the propylene glycol fatty acid monoester obtained is 57.8%.
Comparative example 2
280g soya fatty acid and 306g propylene glycol (mol ratio of propylene glycol/fatty acid is 4:1) are mixed, add pH be 6.0, the phosphate buffer 3g of ion concentration 0.1N, with 15g partial glyceride lipase LipaseSMG1, be placed in 400rpm, the constant temperature blender with magnetic force of 35 DEG C and carry out esterification. Sampling every 1h, the acidity of titration esterification products, after esterification carries out 26h, the acid value of reaction system is reduced to 21.9mgKOH/g, continues reaction acid value and reduces not notable, it was shown that esterification has reached balance. Terminate reaction and be centrifuged esterification products separating, reclaiming oil phase and unreacted propylene glycol and catalyst. Utilizing liquid-phase chromatographic analysis oil phase to form, calculate the yield of propylene glycol fatty acid monoester, result is in Table 1. Just can basically reaching balance after visible esterification 26h, the yield of propylene glycol fatty acid monoester is 88.72%.
Esterification products centrifugation is reclaimed oil phase and unreacted propylene glycol and catalyst, utilizes the propylene glycol fatty acid monoester in secondary molecules separated purification esterification products oil phase. The charging flow velocity of molecular distillation is 1.0mL/min, and one-level evaporating temperature is 100 DEG C, and dual evaporation temperature is 150 DEG C, and injector temperature is 90 DEG C, and condensation temperature is 60 DEG C, it is possible to obtain the propylene glycol fatty acid monoester that purity is 97.5%.
During table 1 esterification balance, oil phase forms and product composition after molecular distillation
Claims (10)
1. the enzymatic-process preparation method of a propylene glycol fatty acid monoester, it is characterised in that comprise the steps:
(1) take fatty acid and intensification makes it melt to be in liquid, then add propylene glycol and homogenizing processes, as esterification substrate;
(2) partial glyceride lipase and esterification substrate contact, adding pH is the buffer of 4～8, and stirring carries out esterification synthesizing propanediol fatty-acid monoester;
(3) reaction product isolated, reclaims oil phase, oil phase is easily separated purification and namely obtains highly purified propylene glycol fatty acid monoester.
2. preparation method according to claim 1, it is characterised in that the mol ratio of step (1) described propylene glycol and fatty acid is 2:1～6:1.
3. preparation method according to claim 2, it is characterised in that the mol ratio of step (1) described propylene glycol and fatty acid is at 3:1～4:1.
4. preparation method according to claim 1, it is characterised in that the addition of described partial glyceride lipase is the 0.5%～10% of fatty acid quality.
5. preparation method according to claim 1, it is characterised in that the addition of step (2) described buffer is not higher than the 1% of propylene glycol quality.
6. preparation method according to claim 5, it is characterised in that step (2) described buffer is phosphate buffer, pH is 5～7.
7. the preparation method according to any one of claim 1～6, it is characterised in that the temperature of step (2) described esterification is 20 DEG C～65 DEG C, more than stirring condition 200rpm, response time 12～24h.
8. preparation method according to claim 7, it is characterised in that the temperature of step (2) described esterification is 40 DEG C～65 DEG C.
9. preparation method according to claim 8, it is characterised in that step is separated into centrifugation described in (2), and temperature of charge is below 40 DEG C.
10. the preparation method according to any one of claim 1～6, it is characterized in that, monoglyceride lipase or diglyceride lipase that described partial glyceride lipase includes deriving from the fatty tissue of animal organ, derive from the monoglyceride lipase of Bacillussp.H-257, derive from the diglyceride lipase of PenicilliumcamembertiiU-150 and derive from the diglyceride lipase LipaseSMG1 of Malasseziaglobosa.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114525313A (en) * | 2022-02-25 | 2022-05-24 | 陕西科技大学 | Method for synthesizing propylene glycol fatty acid monoester by enzyme method |
| CN116218922A (en) * | 2023-02-24 | 2023-06-06 | 江南大学 | Enzymatic preparation method of diglyceride oil |
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| CN102676592A (en) * | 2012-02-29 | 2012-09-19 | 华南理工大学 | Application of lipase SMG1 in preparation of fatty acid monoglyceride |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102676592A (en) * | 2012-02-29 | 2012-09-19 | 华南理工大学 | Application of lipase SMG1 in preparation of fatty acid monoglyceride |
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| 李文哲等: "《生物质能源工程》", 31 January 2013, 中国农业出版社 * |
| 袁勤生等: "《酶与酶工程》", 31 August 2012, 华东理工大学出版社 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114525313A (en) * | 2022-02-25 | 2022-05-24 | 陕西科技大学 | Method for synthesizing propylene glycol fatty acid monoester by enzyme method |
| CN114525313B (en) * | 2022-02-25 | 2024-04-19 | 广州市宝桃食品有限公司 | Method for synthesizing propylene glycol fatty acid monoester by enzymatic method |
| CN116218922A (en) * | 2023-02-24 | 2023-06-06 | 江南大学 | Enzymatic preparation method of diglyceride oil |
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