CN105219813A - In a kind of subcritical system, enzyme process prepares the method for OPO - Google Patents
In a kind of subcritical system, enzyme process prepares the method for OPO Download PDFInfo
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Abstract
The present invention relates to enzyme process in a kind of subcritical system and prepare 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, comprise the steps: that (1) raw material prepares: choose cholesterol mass content lower than 0.05% lard as raw material A, or choose sn-2 palmitinic acid mass content and be not less than the restructuring plam oil of 60% as raw material A; Choose at least one in oleic acid, oleic acid ester as raw material B; (2) subcritical enzyme catalysis transesterification reaction: in subcritical system, under the catalysis of lipase, there is selective enzymatic transesterification reaction in raw material A and raw material B, obtain OPO in reaction solvent.It is fast that the method has speed of reaction, and selectivity is high, and enzyme dosage is few, no solvent residue, is easy to the feature of extensive consecutive production.
Description
Technical field
The present invention relates to a kind of foodstuff additive-human milk fat surrogate, particularly relate to the preparation method of OPO, belong to foodstuff additive and structured lipid preparation field.
Background technology
1,3-bis-oleic acid-2-palmitic acid three ester (hereinafter referred to as OPO) is the nutrition-fortifying agent of the Ministry of Health of China in 2008 No. 13 bulletin approval, being mainly used in dispensed food for baby, is that commercialization human milk fat substitute product is as the important component in betapol45TM and InfatTM.OPO and human milk fat structural similitude, because of its distinctive fatty acid structure composition, not easily form calcium soap when participating in digestion and produce constipation, not only helping lend some impetus to the absorption of infant to mineral substance such as calcium, strengthen the skeleton density of infant, the receptivity of infant to nutrient substance can also be improved.Being defined as OPO with edible vegetable oil in GB (suggestion original text) is that raw material and oleic acid (coming from edible vegetable oil) obtain through lipase-catalyzed transesterify.
For the research of enzymatic clarification human milk substitute; existing a lot of both at home and abroad; and market abroad there is the business-like product of comparative maturity; its synthetic method is uncomplicated in principle; enzymatic method is adopted to synthesize; namely adopting Sn-1, there is transesterification reaction sintetics with acry radical donor (free lipid acid and fatty acid ester) in the glyceride stock containing abundant palmitinic acid (C16:0) on the Sn-2 position of 3 specific lipase catalyzing glycerol skeletons.The representational BetapolTM product of most, lipid acid composition and the distribution of imitating breast milk, the vegetables oil being rich in Sn-2 position palmitinic acid is mixed with the sunflower oil being rich in oleic acid, through the katalysis of specific lipase and a kind of Vegetable oil lipoprotein mixture developed, it is nutritive value and palmitic acid content and the position distribution Novel fatty close to human milk fat.It is the method that material, enzyme method produces OPO structured lipid that patent 201110139857.8 discloses a kind of lard that adopts; Patent 201310264723.8 discloses a kind of method adopting solvent to divide to carry OPO structured lipid in enrichment lard; Patent 201110022672.9 discloses a kind of method that chemical method and enzyme process combine and produces OPO structured lipid, but step is more loaded down with trivial details.
Research is in the past many to be carried out under condition of no solvent, and owing to passing the restriction of resistance hysteresis, speed of response is comparatively slow, and the reaction times is longer, and enzyme dosage is large, and easily occurs that acyl group shifts, and target product productive rate is not high; And when adopting the long chain alkane such as normal hexane, octane-iso to make solvent, be difficult to after completion of the reaction remove totally, easily produce dissolvent residual.And; reported 1; 3-selected fat enzyme mainly contains LipozymeRMIM(Novozymes Company), RhizopusDelamar etc.; lipase fancy price and the high-efficiency enzyme promoted reaction system of shortage are the major causes causing the cost preparing OPO to remain high, and have become the bottleneck problem of puzzlement OPO large-scale production.
Summary of the invention
Technical problem to be solved by this invention is the deficiency that exists for above-mentioned prior art and provides enzyme process in a kind of subcritical system to prepare 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, lipase-catalyzed preparation OPO structured lipid is utilized first in subcritical system, effective raising speed of reaction and transformation efficiency, can not produce destruction to lipase; Enzymatic reaction selectivity is high, and not easily produces dissolvent residual.
The technical scheme that the problem that the present invention is the above-mentioned proposition of solution adopts is:
In subcritical system, enzyme process prepares a method for OPO, and it comprises the steps:
1) raw material prepares: choose cholesterol mass content lower than 0.05% lard as raw material A, or choose sn-2 position and be rich in the restructuring plam oil of palmitinic acid as raw material A; Choose at least one in oleic acid, oleic acid ester as raw material B;
2) subcritical enzyme catalysis transesterification reaction: in subcritical system, under the catalysis of lipase, there is selective enzymatic transesterification reaction in raw material A and raw material B, obtain the thick product of OPO in reaction solvent.
By such scheme, described step 2) follow-uply also comprise step 3), this step 3) is thick product separation and purifying, and the raw material B that the lipase in thick product is residual removes, to obtain the OPO product refined.In this refining OPO product, OPO content is more than 41%.
By such scheme, described cholesterol mass content is as follows lower than the preparation method of the lard of 0.05%: lard adopts solvent extraction to remove most of cholesterol, obtains the lard raw material of lower cholesterol content.Method is more specifically: lard is heated to 50 ~ 70 DEG C, add volumetric concentration be 70 ~ 80% aqueous ethanolic solution extract, leave standstill after stirring and remove lower floor's aqueous phase, get oil phase part and repeat this extraction process again, wherein the add-on of aqueous ethanolic solution is preferably 30 ~ 40wt% of lard quality.
By such scheme, the restructuring plam oil that palmitinic acid is rich in described sn ~ 2 refers to that sn-2 position palmitinic acid mass content is not less than the restructuring plam oil of 60%, is obtained by the random transesterification reaction of chemistry by 52 degree of palmitic stearins.Wherein, in the random transesterification reaction of described chemistry, catalyzer is sodium methylate or sodium ethylate, and catalyst loading is 1 ~ 2% of 52 degree of palmitic stearin quality, temperature of reaction 80 ~ 110 DEG C, reaction times 0.5 ~ 1h.
By such scheme, described oleic acid is be rich in oleic vegetable oils to be hydrolyzed the product obtained; Oleic acid ester is be rich in oleic vegetable oils methyl esters/ethyl esterified product be obtained by reacting.Wherein, described in be rich in oleic vegetable oils be the vegetables oil that oleic acid content is greater than 60%, be selected from one or more mixtures in any proportion in Canola Oil, sweet oil, tea-seed oil, high oleic sunflower oil etc.
By such scheme, described step 2) in, the mass ratio of raw material A and raw material B is 1:(1 ~ 3), lipase is 3% ~ 10% of raw material A and raw material B total mass.
By such scheme, described step 2) in, the temperature of subcritical system is 40 ~ 60 DEG C, and pressure is 0.5 ~ 4MPa, and the reaction times is 1 ~ 4h.
By such scheme, described step 2) in, the reaction solvent of subcritical system is selected from one or more solvents mixture in any proportion in propane, butane, R134a, R600a, DME and sulfur hexafluoride etc.Preferably, the add-on of reaction solvent is 2 ~ 5 times of raw material cumulative volume.
By such scheme, described step 2) in, lipase is 1,3 specific lipases, are selected from antarctic candidia lipase, rizolipase, miehei lipase, Candida lipalytica Lipase, thermophilic hyphomycete lipase, Candida antarctica belong to one or more mixtures in any proportion in lipase, aspergillus niger Pseudomonas lipase or rhizomucor miehei lipase etc.
By such scheme, described lipase comprises the lipase of sequestered and immobilization form, the lipase of preferred immobilization form.Wherein, the carrier of immobilized enzyme is selected from one or more mixtures in any proportion in macroporous resin, silica gel, diatomite, attapulgite etc.
By such scheme, the means be separated in described step 3) are suction filtration, to remove catalyzer lipase; The means of purifying are distillation or extraction, to remove raw material B residual in thick product.More specifically, the temperature of described suction filtration is 50 ~ 60 DEG C, number of times preferably 2 ~ 4 times.More specifically, described distillation is short-range molecular distillation, vacuum tightness 1 ~ 40Pa, vaporization temperature 180 ~ 220 DEG C.
Compared with prior art, the invention has the beneficial effects as follows:
1, the present invention utilizes lipase-catalyzed preparation OPO structured lipid first in subcritical system, subcritical fluids is as reaction medium, biography resistance hysteresis can be reduced, perviousness is strong, good to reaction raw materials solubleness, enzyme dosage is few, adds and is conducive to reducing the diffusional limitation that in enzymic catalytic reaction, substrate contacts with enzyme, improves enzyme kinetics and improves speed of reaction and transformation efficiency;
2, the present invention is by adopting in subcritical reaction system, preparation process is carried out at a lower temperature, be conducive to the vigor of protective enzyme, and subcritical fluids mostly is non-polar solvent, can not produce destruction to lipase; Enzymatic reaction selectivity is high, and the acyl group rate of transform is low;
3, preparation method of the present invention carries out in subcritical reaction system, can be facilitated and is comparatively fully separated from product by solvent and recycling, and not easily produce dissolvent residual by pressure change; Further, subcritical equipment pressure is lower, and greatly can reduce disposable apparatus and drop into and working cost, continuous production is good, should be able to be suitable for the extensive consecutive production of modernization.
Embodiment
In order to understand the present invention better, illustrate content of the present invention further below in conjunction with embodiment, but content of the present invention is not only confined to the following examples.
In the present invention, the lipase of described immobilization form, be called for short immobilized lipase, can be commercially available LipozymeRMIM, LipozymeTLIM etc., also can prepare voluntarily, its preparation method comprises following step:
1) activation of carrier: with impurity such as metal ions in 1mol/L hydrochloric acid soln immersion removing carrier, then pure water cleaning is to neutral; 2) adsorption of immobilization: preparation buffered soln, is dissolved in buffered soln by free-fat enzyme, then adds the carriers such as silica gel, resin, diatomite, vacuumize whip attachment 0.5 ~ 4h, collected by suction immobilized lipase crude product; 3) washing is dry: after immobilized lipase crude product buffered soln is cleaned 3 times, lyophilize or cold air drying can being fixed lipase products.
Adopt any device that can realize subcritical system all can realize technical scheme of the present invention, what embodiment 1 ~ 11 adopted is device disclosed in patent 200910034263.3.Specific operation process is as follows: 1) retort is warming up to setting temperature of reaction and keeps temperature-stable by circulator bath; 2) take raw material and immobilized lipase is placed in autoclave, after system is airtight, open solvent tank, solvent gas enters reactor through condenser post liquefaction through pressurization, be forced into the different pressures of setting, after reaching selected pressure, stop plunger pump, close storage tank, then, after airtight stirring reaction to setting-up time, open valve decompression, then open compressor from separating still recycling design, from retort, reclaim lipase, from separating tank, reclaim thick product.
embodiment 1
Under subcritical state, enzyme process prepares a method for OPO, comprises the steps:
(1) preparation of raw material A: adopt 52 degree of palmitic stearins to be raw material, sodium methylate is catalyzer, sodium methylate addition is 1% of 52 degree of palmitic stearin quality, in temperature of reaction 80 DEG C reaction 1h, then aqueous citric acid solution removing sodium methylate is adopted, rotary evaporation removing moisture, can obtain the restructuring plam oil that sn-2 position palmitinic acid mass content is not less than 60%, i.e. raw material A;
Raw material B selects oleic acid, derives from the hydrolysis of high gas oil ratio rapeseed oil;
(2) subcritical enzyme catalysis transesterification reaction: 500g raw material A, 500g raw material B, 30g diatomite immobilization Candida lipalytica Lipase are added in autoclave, add the propane solvent of 5L liquefaction, in Propane system, 40 DEG C, under the condition of pressure 0.5MPa, stirring reaction 4h, open valve after completion of the reaction and product is proceeded to separating still, be separated with Valve controlling by compressor, reaction solvent propane is reclaimed from separating still, lipase is reclaimed from retort, the thick product of OPO is reclaimed from separating tank;
(3) product separation purifying: the thick product that step (2) obtains while hot suction filtration reclaims lipase and obtains lipase filter cake and liquid crude product, then by liquid crude product at 50 DEG C again through lipase filter cake suction filtration 2 times repeatedly, obtain the product after suction filtration; Suction filtration after product carries out employing molecular distillation under the condition of temperature 180 DEG C, vacuum tightness 1Pa, removes oleic acid excessive in thick product, and obtain the OPO product refined, productive rate is 88%, and purity is greater than 41%.
embodiment 2
Under subcritical state, enzyme process prepares a method for OPO, comprises the steps:
(1) preparation of raw material A: adopt 52 degree of palmitic stearins to be raw material, sodium ethylate is catalyzer, sodium ethylate addition is 2% of 52 degree of palmitic stearin quality, in temperature of reaction 100 DEG C reaction 0.5h, then aqueous citric acid solution removing sodium ethylate is adopted, rotary evaporation removing moisture, can obtain the restructuring plam oil that sn-2 position palmitinic acid mass content is not less than 60%, i.e. raw material A;
Raw material B selects oleic acid, derives from olive oil hydrolysis;
(2) subcritical enzyme catalysis transesterification reaction: by 500g raw material A, 1000g raw material B, 75g silica gel immobilized candida antarctica lipase (5% of raw material total mass) adds in autoclave, add the butane solvent of 4.5L liquefaction, in subcritical butane system, at 50 DEG C, under the condition of pressure 1.4MPa, stirring reaction 3h, open valve after completion of the reaction and product is proceeded to separating still, be separated with Valve controlling by compressor, reaction solvent propane is reclaimed from separating still, lipase is reclaimed from retort, 1 is reclaimed from separating tank, the thick product of 3-bis-oleic acid-2-palmitic acid three ester,
(3) product separation purifying: the thick product that step (2) obtains while hot suction filtration reclaims lipase and obtains lipase filter cake and liquid crude product, then by liquid crude product at 50 DEG C again through lipase filter cake suction filtration 2 times repeatedly, obtain the product after suction filtration; Suction filtration after product carries out employing molecular distillation under the condition of temperature 190 DEG C, vacuum tightness 10pa, removes oleic acid excessive in thick product, and obtain the OPO product refined, productive rate is 89%, and purity is greater than 42%.
embodiment 3
Under subcritical state, enzyme process prepares a method for OPO, comprises the steps:
(1) preparation of raw material A: adopt 52 degree of palmitic stearins to be raw material, sodium ethylate is catalyzer, sodium ethylate addition is 2% of 52 degree of palmitic stearin quality, in temperature of reaction 110 DEG C reaction 0.5h, then aqueous citric acid solution removing sodium ethylate is adopted, rotary evaporation removing moisture, can obtain the restructuring plam oil that palmitinic acid is rich in sn-2 position, i.e. raw material A;
Raw material B selects oleic acid, derives from tea-seed oil hydrolysis;
(2) subcritical enzyme catalysis transesterification reaction: by 500g raw material A, 1500g raw material B, the immobilization of 160g macroporous resin is thermophilic, and hyphomycete lipase (8% of raw material total mass) adds in autoclave, add the R134a solvent of 4L liquefaction, in subcritical R134a system, at 60 DEG C, under the condition of pressure 4MPa, stirring reaction 1h, open valve after completion of the reaction and product is proceeded to separating still, be separated with Valve controlling by compressor, reaction solvent propane is reclaimed from separating still, lipase is reclaimed from retort, 1 is reclaimed from separating tank, the thick product of 3-bis-oleic acid-2-palmitic acid three ester,
(3) product separation purifying: the thick product that step (2) obtains while hot suction filtration reclaims lipase and obtains lipase filter cake and liquid crude product, then by liquid crude product at 60 DEG C again through lipase filter cake suction filtration 3 times repeatedly, obtain the product after suction filtration; Suction filtration after product carries out employing molecular distillation under the condition of temperature 200 DEG C, vacuum tightness 20pa, removes oleic acid excessive in thick product, and obtain the OPO product refined, productive rate is 86%, and purity is greater than 45%.
embodiment 4
Under subcritical state, enzyme process prepares a method for OPO, comprises the steps:
(1) preparation of raw material A: lard is raw material, lard is heated to 50 DEG C, add volumetric concentration be 80% aqueous ethanolic solution extract, leave standstill after stirring and remove lower floor's aqueous phase, get oil phase part to repeat said process again and extract 1 time, revolve and steam removing etoh solvent, the lard of low-cholesterol can be obtained, i.e. raw material A; Wherein the add-on of aqueous ethanolic solution is the 40wt% of lard quality;
Raw material B selects oleic acid, derives from high oleic sunflower oil hydrolysis;
(2) subcritical enzyme catalysis transesterification reaction: by 500g raw material A, 500g raw material B, the immobilization of 100g attapulgite is thermophilic, and hyphomycete lipase (10% of raw material total mass) adds in autoclave, add the butane solvent of 5L liquefaction, in subcritical butane system, at 60 DEG C, under the condition of pressure 1.5MPa, stirring reaction 1h, open valve after completion of the reaction and product is proceeded to separating still, be separated with Valve controlling by compressor, reaction solvent propane is reclaimed from separating still, lipase is reclaimed from retort, 1 is reclaimed from separating tank, the thick product of 3-bis-oleic acid-2-palmitic acid three ester,
(3) product separation purifying: the thick product that step (2) obtains while hot suction filtration reclaims lipase and obtains lipase filter cake and liquid crude product, then by liquid crude product at 50 DEG C again through lipase filter cake suction filtration 2 times repeatedly, obtain the product after suction filtration; Suction filtration after product carries out employing molecular distillation under the condition of temperature 220 DEG C, vacuum tightness 40pa, removes oleic acid excessive in thick product, and obtain the OPO product refined, productive rate is 95%, and purity is greater than 45%.
embodiment 5
Substantially the same manner as Example 1, difference is in step (1): the oleic acid that raw material oleic acid origin comes from peanut oil hydrolysis substitutes.Can obtain refining OPO product, productive rate is 90%, and purity is greater than 41%.
embodiment 6
Substantially the same manner as Example 1, difference is in step (1): raw material oleic acid is substituted by Witconol 2301.Can obtain refining OPO product, productive rate is 92%, and purity is greater than 41%.
embodiment 7
Substantially the same manner as Example 1, difference is in step (1): raw material oleic acid is substituted by ethyl oleate.Can obtain refining OPO product, productive rate is 88%, and purity is greater than 41%.
embodiment 8
Substantially the same manner as Example 1, difference is in step (2): diatomite immobilization Candida lipalytica Lipase is substituted by diatomite immobilization rizolipase, propane is substituted by dme, refining 1 can be obtained, 3-bis-oleic acid-2-palmitic acid three ester product, productive rate is 89%, and purity is greater than 41%.
embodiment 9
Substantially the same manner as Example 1, difference is in step (2): diatomite immobilization Candida lipalytica Lipase is substituted by diatomite immobilization miehei lipase, propane is substituted by liquefied petroleum gas (LPG), refining 1 can be obtained, 3-bis-oleic acid-2-palmitic acid three ester product, productive rate is 93%, and purity is greater than 41%.
embodiment 10
Substantially the same manner as Example 1, difference is in step (2): diatomite immobilization Candida lipalytica Lipase is substituted by diatomite Immobilized Aspergillus niger Pseudomonas lipase, propane is substituted by sulfur hexafluoride, refining 1 can be obtained, 3-bis-oleic acid-2-palmitic acid three ester product, productive rate is 92%, and purity is greater than 41%.
embodiment 11
Substantially the same manner as Example 1, difference is in step (2): diatomite immobilization Candida lipalytica Lipase is substituted by sequestered rhizomucor miehei lipase, propane is substituted by sulfur hexafluoride, refining 1 can be obtained, 3-bis-oleic acid-2-palmitic acid three ester product, productive rate is 91%, and purity is greater than 41%.
In sum, under subcritical state of the present invention, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, reaction times, relative to prior art, speed of reaction had large increase within the scope of 1 ~ 4h, and the consumption of catalyzer lipase is only 3% ~ 10% of raw material total mass, the productive rate of gained target product OPO can reach more than 85%, and purity can reach more than 41%.
The above is only the preferred embodiment of the present invention, it should be pointed out that for the person of ordinary skill of the art, and without departing from the concept of the premise of the invention, can also make some improvement and conversion, these all belong to protection scope of the present invention.
Claims (10)
1. in subcritical system, enzyme process prepares a method for OPO, it is characterized in that it comprises the steps:
1) raw material prepares: choose cholesterol mass content lower than 0.05% lard as raw material A, or choose sn-2 palmitinic acid mass content and be not less than the restructuring plam oil of 60% as raw material A; Choose at least one in oleic acid, oleic acid ester as raw material B;
2) subcritical enzyme catalysis transesterification reaction: in subcritical system, under the catalysis of lipase, there is selective enzymatic transesterification reaction in raw material A and raw material B, obtain the thick product of OPO in reaction solvent.
2. in the subcritical system of one according to claim 1, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that described step 2) follow-uply also comprise step 3), this step 3) is thick product separation and purifying, the raw material B that lipase in thick product is residual removes, to obtain the OPO product of mass content more than 41%.
3. in a kind of subcritical system according to claim 2, enzyme process prepares the method for OPO, it is characterized in that the means be separated in described step 3) are suction filtration, to remove catalyzer lipase; The means of purifying are distillation or extraction, to remove raw material B residual in thick product.
4. in a kind of subcritical system according to claim 3, enzyme process prepares the method for OPO, and it is characterized in that the temperature of described suction filtration is 50 ~ 60 DEG C, number of times is 2 ~ 4 times; Described distillation is short-range molecular distillation, vacuum tightness 1 ~ 40Pa, vaporization temperature 180 ~ 200 DEG C.
5. in the subcritical system of one according to claim 1, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that described step 2) in, the mass ratio of raw material A and raw material B is 1:(1 ~ 3), lipase is 3% ~ 10% of raw material A and raw material B total mass.
6. in the subcritical system of one according to claim 1, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, is characterized in that described step 2) in, the temperature of subcritical system is 40 ~ 60 DEG C, pressure is 0.5 ~ 4MPa, and the reaction times is 1 ~ 4h.
7. in the subcritical system of one according to claim 1, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that described step 2) in, the reaction solvent of subcritical system is selected from one or more solvents mixture in any proportion in propane, butane, R134a, R600a, DME and sulfur hexafluoride.
8. in the subcritical system of one according to claim 1, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, it is characterized in that described step 2) in, lipase is 1,3-specific lipase, is selected from antarctic candidia lipase, rizolipase, miehei lipase, Candida lipalytica Lipase, thermophilic hyphomycete lipase, Candida antarctica belongs to one or more mixtures in any proportion in lipase, aspergillus niger Pseudomonas lipase or rhizomucor miehei lipase.
9. in a kind of subcritical system according to claim 1, enzyme process prepares the method for OPO, it is characterized in that described lipase comprises the lipase of sequestered and immobilization form.
10. in the subcritical system of one according to claim 9, enzyme process prepares 1, the method of 3-bis-oleic acid-2-palmitic acid three ester, is characterized in that the carrier of the lipase of described immobilization form is selected from one or more mixtures in any proportion in macroporous resin, silica gel, diatomite, attapulgite.
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| PCT/CN2016/079818 WO2017084241A1 (en) | 2015-11-20 | 2016-04-21 | Method for preparing 1,3-dioleoyl-2-palmitoylglycerol in a subcritical system |
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| KR101126305B1 (en) * | 2005-09-08 | 2012-03-19 | 로더스 크로클란 비.브이. | Process for producing dioleoyl palmitoyl glyceride |
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| CN101157945B (en) * | 2007-09-13 | 2010-06-02 | 中国海洋大学 | Technique for preparing glycerin ester rich in polyunsaturated fatty acid |
| CN101642632B (en) * | 2009-09-03 | 2012-05-30 | 江苏大学 | Subcritical liquid extraction device and subcritical liquid extraction method of active ingredients of natural products |
| CN102229866B (en) * | 2011-05-27 | 2013-05-01 | 北京化工大学 | Method for producing 1,3-dioleoyl-2-palmitoyl triglyceride |
| CN102757988B (en) * | 2012-07-25 | 2015-01-21 | 浙江大学 | Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride |
| CN105219813B (en) * | 2015-11-20 | 2019-03-08 | 中国农业科学院油料作物研究所 | A kind of method that enzyme process prepares bis- oleic acid -2- palmitic acid of 1,3-, three ester in subcritical system |
-
2015
- 2015-11-20 CN CN201510803841.0A patent/CN105219813B/en active Active
-
2016
- 2016-04-21 WO PCT/CN2016/079818 patent/WO2017084241A1/en active Application Filing
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017084241A1 (en) * | 2015-11-20 | 2017-05-26 | 中国农业科学院油料作物研究所 | Method for preparing 1,3-dioleoyl-2-palmitoylglycerol in a subcritical system |
| CN107338279A (en) * | 2017-09-01 | 2017-11-10 | 广州立达尔生物科技股份有限公司 | Lipase-catalyzed esterification produces lutein carboxylate |
| CN110724716A (en) * | 2018-07-16 | 2020-01-24 | 浙江贝家生物科技有限公司 | A method for preparing composition containing 1, 3-dioleoyl-2-palmitic acid triglyceride |
| CN108841880A (en) * | 2018-08-01 | 2018-11-20 | 浙江汇能生物股份有限公司 | A kind of preparation method of 1,3-Dioleic acid-2-palmitoyl triglyceride |
| CN108841880B (en) * | 2018-08-01 | 2022-05-31 | 浙江汇能生物股份有限公司 | Preparation method of 1, 3-dioleoyl-2-palmitic acid triglyceride |
| CN109251943A (en) * | 2018-08-28 | 2019-01-22 | 江苏大学 | A kind of supercritical CO2Under the conditions of the enzymatic method for preparing OPO structured lipid |
| CN109251943B (en) * | 2018-08-28 | 2021-02-12 | 江苏大学 | Supercritical CO2Method for preparing OPO structure lipid under condition of enzyme catalysis |
| CN109777844A (en) * | 2019-02-14 | 2019-05-21 | 华南协同创新研究院 | A kind of method that subcritical one-step method prepares monolaurin |
| CN109777844B (en) * | 2019-02-14 | 2020-10-09 | 华南协同创新研究院 | Method for preparing mono-decyl lauric glyceride by subcritical one-step method |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017084241A1 (en) | 2017-05-26 |
| CN105219813B (en) | 2019-03-08 |
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