CN104178531B - Method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil - Google Patents
Method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil Download PDFInfo
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Abstract
The invention relates to a method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil. The method is characterized by comprising the following steps: (1) addition of reaction raw materials: adding phytosterin, high-acid-value grease and molecular sieve into a reaction kettle, adding 100-200ppm of antioxidant, heating to 45-60 DEG C, stirring and carrying out ultrasonic treatment to obtain a premixture, wherein the mole ratio of the phytosterin to free fatty acids in the high-acid-value grease is 1:1-5:1; (2) enzymatic ester exchange reaction: adding 5-40 g/L lipase into the premixture, and stirring to react at 45-60 DEG C under normal pressure for 6-12 hours; and (3) carrying out after-treatment on the product to obtain the functional grease containing rich phytosterin ester. The method can obviously lower the acid value of the high-acid-value vegetable oil and generate the new functional active component phytosterin ester, and the product is simple for separation and purification; and thus, the method can easily implement large-scale amplification.
Description
Technical field
The present invention relates to the use of high valent acid vegetable oil and produce the preparation method being rich in plant sterol ester biodiesel, specifically relate to
And utilize high valent acid vegetable oil to be raw material, by the side rich in plant sterol ester biodiesel for the lipase-catalyzed esterification method one step preparation
Method, belongs to oils and fatss deep processing and higher value application field.
Background technology
Normal vegetable oil its acid value typically ratio producing is relatively low, but in particular cases, such as in oil plant, moisture is high, preserve not
When and processing in play the role of enzyme etc., lead to the acid value of lipids produced higher, wherein have high acid value Semen Tritici aestivi than more typical
Germ oil and high acid value Testa oryzae oil.High acid value oils and fatss are primarily referred to as the oils and fatss that acid value is more than 20mgkoh/g.The generation of high acid value oils and fatss
Not only its Fatty acid compositions is more reasonable for table Testa oryzae oil, and containing abundant oryzanol, Squalene, ve (tocopherol, life
Educate trienol), the various active material such as sterol, therefore there is enhance immunity, reduce cholesterol, adjust blood fat, prevent tremulous pulse
The physiologically active such as atherosis, is described as " nutrition oil " by nutritionist, is a kind of ideal edible oil and fat.Contain in Testa oryzae and live
Property higher lipolytic enzyme, lead to the free fatty acid content in Testa oryzae oil higher, typically more than 10%, some even exist
Between 30%-40%.At present, high acid value oils and fatss be mainly used in deacidification become low acid value oils and fatss, preparation biodiesel and fatty acid etc..
High acid value oils and fatss carry out deacidification according to conventional grease acid stripping method and can have that environmental pollution is serious, energy consumption big, neutral fat yield
Low problem.Testa oryzae oil acid number can be reduced to regulation and require by traditional alkali-refining deacidification method, but alkali refining makes paddy in Testa oryzae oil
The nutritional labelings such as dimension element run off in a large number, simultaneously as soap is carried secretly and inevitable fat saponification to the emulsifying of oils and fatss, serious shadow
Ring oil and fat refining yield.With the development of biotechnology, this reaction condition of zymotechnic is gentle, the novel process of high catalytic efficiency
Technology causes the attention of related scholar.Being used at present relatively broad is to be as acyl acceptor using glycerol or monoglyceride
Esterifying agent, occurs esterification to reach the purpose of deacidification with free fatty.
The physiology such as plant sterol ester not only remains plant sterol reduction cholesterin and regulating blood-fat, antiinflammatory is brought down a fever, anticancer are lived
Property, also have preferably fat-soluble, in oils and fatss or containing the application more broad range in fatty foods.In addition, plant sterol ester
Absorption rate be 5 times of plant sterol, and there is more preferably Lowering cholesterol effect, be a kind of new functional food base
Material.2010, plant sterol ester was listed in new food resource by China's Ministry of Public Health.
The present invention is using plant sterol as dissociating in acry radical donor and the high-acid value grease such as Testa oryzae oil or Semen Tritici aestivi germ oil
There is enzymatic esterification in fatty acid, on the one hand can substantially reduce the acid value of high-acid value grease, on the other hand can generate new
Functional active components plant sterol ester, may finally obtain the biodiesel rich in plant sterol ester.At present, carry out both at home and abroad
The report of plant sterol ester study on the synthesis is more, but is not yet related to high-acid value greases such as peracid value rice bran oil, Semen Tritici aestivi germ oils
For raw material, the research report rich in plant sterol ester biodiesel for the preparation.
Content of the invention
It is an object of the invention to provide a kind of utilization high valent acid vegetable oil produces rich in plant sterol ester biodiesel
Method, the acid value of high-acid value grease (Testa oryzae oil etc.) can substantially drop in the method one side, on the other hand can generate new function
Active component plant sterol ester, product need not assist and isolate and purify, easy and simple to handle.
For achieving the above object, the technical solution used in the present invention is as follows: a kind of rich using high valent acid vegetable oil production
Method containing plant sterol ester biodiesel is it is characterised in that it comprises the steps:
(1) pretreatment of raw material: reaction dissolvent adopts anhydrous sodium sulfate eliminating water, 80 DEG C -120 DEG C vacuum drying of plant sterol
8-12h, the moisture of reaction dissolvent controls in below 0.1wt%, and the moisture of plant sterol controls in below 1wt%,
The moisture of high acid value oils and fatss controls in below 0.2wt%；
(2) input of reaction raw materials: by the free fatty in plant sterol, high acid value oils and fatss mol ratio be 1:1-5:
The mean molecule quantity of the acid value/2 × free fatty of amount (molal quantity)=high-acid value grease of the material of 1[free fatty],
Plant sterol is 100-400mmol:1l with the proportioning of reaction dissolvent, and the addition of molecular sieve is 100g/l (i.e. in every liter of solvent
Add 100g molecular sieve, it would however also be possible to employ solventless method, that is, using raw material high-acid value grease as solvent), by plant sterol (100-
400mm), high acid value oils and fatss (high-acid value grease) (20-400mm), reaction dissolvent (or solvent-free), molecular sieve (100g/l) add
In reactor, add 100-200ppm antioxidant [i.e. antioxidant in solvent (referring to reaction dissolvent or/and high acid value oils and fatss)
Concentration be 100-200ppm], be heated to 45-60 DEG C stirring and supersound process, process time be 30-60 minute, premixed
Thing；
(3) enzymatic interesterification procedure: add 5-40g/l Digestive Enzyme (to add 5-40g fat in every liter of pre-composition in pre-composition
Enzyme), in the range of 45-60 DEG C, stirring reaction 6-12h under condition of normal pressure, stop heating, naturally cool to room temperature；
(4) post processing of product: after completion of the reaction, be centrifuged off Digestive Enzyme, molecular sieve, be filtered to remove after being cooled to 4 DEG C
Unreacted plant sterol, vacuum rotary steam removes reaction dissolvent (during reactionless solvent, then without vacuum rotary steam), that is, be rich in
Sterol ester biodiesel (low acid value and be rich in plant sterol ester).
By such scheme, described plant sterol is stigmasterol, sitosterol, brassicasterol, any one in campesterol
Plant or more than the two kinds mixture by any proportioning.
By such scheme, described high valent acid vegetable oil includes acid value between the Testa oryzae oil of 20-100mgkoh/g, wheat germ
The vegetable oil such as bud oil any one or more than two kinds press the mixture of any proportioning, do not include waste grease.
By such scheme, described reaction dissolvent (i.e. reaction dissolvent of enzymatic esterification) is normal hexane, isobutyltrimethylmethane., hexamethylene
Alkane, normal heptane etc. one or two or more kinds press any proportioning mixture.Solventless method can also be adopted, that is, with high acid value oils and fatss
Itself, as solvent, does not additionally add other solvents.
By such scheme, described Digestive Enzyme (free or immobilized), including the gauffer vacation silk from fermentable
Yeast-lipase, Candida lipalytica Lipase, antarctic candidia lipase or Pseudomonas cepacia Digestive Enzyme.Preferably originate
Digestive Enzyme in candida rugosa lipase, antarctic candidia lipase or Candida lipolytica.
By such scheme, described antioxidant is natural complex e, fat-soluble tea polyphenol or l- vitamin-c palmitate
The fat-soluble antioxidants such as ester, preferably fat-soluble tea polyphenol.
By such scheme, the power of described supersound process is 100-300w, and supersonic frequency is 25-40hz.
The present invention is with the high acid value vegetable oil such as plant sterol and Testa oryzae oil, Semen Tritici aestivi germ oil as raw material, oily using high acid value
In fat, substantial amounts of free fatty, as acry radical donor, adopts from candida mycoderma, the microorganism such as Bulbus Allii Cepae vacation silk Zymomonas mobiliss
Digestive Enzyme is catalyst, by the method for enzymatic esterification, the biodiesel rich in plant sterol ester for the preparation, can effectively drop simultaneously
The acid value of low raw oil.By optimizing the conditions such as sterol concentration, reaction temperature, time, Digestive Enzyme species and addition, obtain
Optimal processing parameter.This method can achieve deep processing and the higher value application of the high acid value vegetable oil such as Testa oryzae oil, Semen Tritici aestivi germ oil,
Utilization rate and the added value of high acid value vegetable oil can be effectively improved, decrease loaded down with trivial details chemical deacidification step simultaneously.
The beneficial outcomes of the present invention are:
1. whole reaction is carried out under low-temperature atmosphere-pressure, and without nitrogen protection, product is not susceptible to aoxidize, and equipment is simple, behaviour
Make easy；
2. a step enzymatic esterification just can substantially reduce the acid value of high acid value vegetable oil, obtain sterol ester activity simultaneously
Functional component；And product is substantially without isolating and purifying；Reaction condition is gentle；
3. pass through to control the ratio of two kinds of raw materials (plant sterol and high-acid value grease) can produce rich in different content
The biodiesel of sterol ester, to be applied to the needs of different product；
4. the method has raw material eurytopicity it is adaptable to multiple high acid value vegetable oil raw materials such as Testa oryzae oil, Semen Tritici aestivi germ oil.
Specific embodiment
For a better understanding of the present invention, it is further elucidated with present disclosure with reference to embodiment, but the present invention
Content is not limited solely to the following examples.
Embodiment 1:
A kind of utilization high valent acid vegetable oil produces the method rich in plant sterol ester biodiesel, and it comprises the steps:
(1) pretreatment of raw material: reaction dissolvent (normal hexane) adopts anhydrous sodium sulfate eliminating water (moisture < 0.1wt%), paddy steroid
80 DEG C of vacuum drying 12h of alcohol (plant sterol) (moisture < 1wt%), high-acid value grease adopts Testa oryzae oil (moisture < 0.2wt%, acid
Valency 20mgkoh/g)；
(2) input of reaction raw materials: by 5l normal hexane, 207g plant sterol (sitosterol, 100mm), Testa oryzae oil 1400g
(acid value 20mgkoh/g, 100mm containing free fatty), molecular sieve (addition is 50g/l, i.e. 250g) add in reactor, plus
Enter natural complex e antioxidant 200ppm, be heated to 45 DEG C stirring and supersound process (time be 30 minutes, supersound process
Power is 100w, and supersonic frequency is 25hz), obtain pre-composition；
(3) enzymatic interesterification procedure: add 25g (5g/l) antarctic candidia lipase, stir under 45 DEG C of condition of normal pressure
Mix reaction 12h, stop heating, naturally cool to room temperature；
(4) post processing of product: after completion of the reaction, be centrifuged off Digestive Enzyme (antarctic candidia lipase), molecular sieve
With unreacted plant sterol, vacuum rotary steam removing normal hexane, obtain rich in plant sterol ester biodiesel, overall yield of reaction is big
In 88%.Wherein plant sterol ester content is more than 20wt%, and product acid value is less than 5.0mgkoh/g, and peroxide value is less than
5.0meq/kg.Illustrate that the present invention can obviously reduce Testa oryzae oil acid value and obtains the biodiesel rich in plant sterol ester.
Embodiment 2:
A kind of utilization high valent acid vegetable oil produces the method rich in plant sterol ester biodiesel, and it comprises the steps:
(1) pretreatment of raw material: reaction dissolvent (isobutyltrimethylmethane .) adopts anhydrous sodium sulfate eliminating water (moisture < 0.1wt%), bean steroid
100 DEG C of alcohol (plant sterol) vacuum drying 10h (moisture < 1wt%), high-acid value grease with Semen Tritici aestivi germ oil (moisture < 0.2wt%,
Acid value 40mgkoh/g)；
(2) input of reaction raw materials: by 5l isobutyltrimethylmethane., 414g plant sterol (stigmasterol 200mm), Semen Tritici aestivi germ oil 700g
(acid value 40mgkoh/g, 100mm containing free fatty), molecular sieve (addition is 50g/l, i.e. 250g), add fat-soluble tea many
Phenolic antioxidant 150ppm, add reactor in, be heated to 55 DEG C stirring and supersound process (time be 50 minutes, supersound process
Power be 200w, supersonic frequency be 30hz), obtain pre-composition；
(3) enzymatic interesterification procedure: add 100g (20g/l) antarctic candidia lipase in pre-composition, at 55 DEG C often
Stirring reaction 10h under the conditions of pressure, stops heating, naturally cools to room temperature.
(4) post processing of product: after completion of the reaction, be centrifuged off Digestive Enzyme (antarctic candidia lipase), molecular sieve
With unreacted plant sterol, vacuum rotary steam removing isobutyltrimethylmethane., obtain rich in plant sterol ester biodiesel, overall yield of reaction is big
In 85%.Wherein plant sterol ester content is more than 30wt%, and product acid value is less than 4.5mgkoh/g, and peroxide value is less than
3.0meq/kg.Illustrate that the present invention can obviously reduce Semen Tritici aestivi germ oil acid value and obtains the biodiesel rich in plant sterol ester.
Embodiment 3:
A kind of utilization high valent acid vegetable oil produces the method rich in plant sterol ester biodiesel, and it comprises the steps:
(1) pretreatment of raw material: reaction dissolvent (normal heptane) adopts anhydrous sodium sulfate eliminating water (moisture < 0.1wt%), Semen Allii Tuberosi
120 DEG C of sterol vacuum drying 8h (moisture < wt%), high-acid value grease adopts Testa oryzae oil, and (< 0.2wt%, acid value is moisture
100mgkoh/g)；
(2) input of reaction raw materials: by 5l normal heptane, 828g plant sterol (brassicasterol 400mm), Testa oryzae oil 280g
(acid value 100mgkoh/g, fatty acids 80mm), molecular sieve (addition is 50g/l, i.e. 250g), add l ascorbic acid Petiolus Trachycarpi
Acid esters antioxidant 200ppm, add reactor in, be heated to 60 DEG C stirring and supersound process (time be 60 minutes, ultrasonic place
The power of reason is 300w, and supersonic frequency is 40hz), obtain pre-composition；
(3) enzymatic interesterification procedure: add 200g (40g/l) Candida lipalytica Lipase in pre-composition, at 60 DEG C often
Stirring reaction 12h under the conditions of pressure, stops heating, naturally cools to room temperature.
(4) post processing of product: after completion of the reaction, be centrifuged off Digestive Enzyme (Candida lipalytica Lipase), molecular sieve
With unreacted plant sterol, vacuum rotary steam removing normal heptane, obtain rich in plant sterol ester biodiesel, overall yield of reaction is big
In 84%.Wherein plant sterol ester content is more than 50%, and product acid value is less than 4.0mgkoh/g, and peroxide value is less than 4.0meq/
kg.Illustrate that the present invention can obviously reduce Testa oryzae oil acid value and obtains the biodiesel rich in plant sterol ester.
Embodiment 4 (without solvent, with Testa oryzae oil as solvent):
A kind of utilization high valent acid vegetable oil produces the method rich in plant sterol ester biodiesel, and it comprises the steps:
(1) pretreatment of raw material: 80 DEG C of vacuum drying 12h of campesterol (plant sterol) (moisture < 1wt%), high acid value
Oils and fatss adopt Testa oryzae oil (moisture < 0.2wt%, acid value 20mgkoh/g)；
(2) input of reaction raw materials: (acid value 20mgkoh/g, containing fat by 207g campesterol (100mm), Testa oryzae oil 700g
Fat acid 50mm), molecular sieve (addition be 50g/l, i.e. 250g) add in reactor, add natural complex e antioxidant
200ppm, (time is 30 minutes, and the power of supersound process is 200w, and supersonic frequency is to be heated to 50 DEG C of stirrings supersound process
25-40hz), obtain pre-composition；
(3) enzymatic interesterification procedure: add 25g (5g/l) antarctic candidia lipase, stir under 50 DEG C of condition of normal pressure
Mix reaction 12h, stop heating, naturally cool to room temperature；
(4) post processing of product: after completion of the reaction, be centrifuged off Digestive Enzyme, molecular sieve and unreacted plant sterol, obtain
To rich in plant sterol ester biodiesel, overall yield of reaction is more than 85%.Wherein sterol ester content is more than 30wt%, and acid value is less than
4.0mgkoh/g, peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Testa oryzae oil acid value and obtains rich in plant
The biodiesel of sterol ester.
Embodiment 5:
Substantially the same manner as Example 2, difference is in step (1): plant sterol is the mixed of stigmasterol and sitosterol
The quality of compound, stigmasterol and sitosterol respectively accounts for 1/2；Obtain rich in plant sterol ester biodiesel, overall yield of reaction is more than
86%.Wherein plant sterol ester content is more than 30wt%, and acid value is less than 5.0mgkoh/g, and peroxide value is less than 4.0meq/kg.Say
The bright present invention can obviously reduce Testa oryzae oil acid value and obtains the biodiesel rich in plant sterol ester.
Embodiment 6:
Substantially the same manner as Example 3, difference is: antarctic candidia lipase is by candida rugosa lipase
Substitute；Natural complex e antioxidant is changed to 100ppm；Obtain rich in plant sterol ester biodiesel, overall yield of reaction is more than
85%.Wherein plant sterol ester content is more than 50wt%.Acid value is less than 6.0mgkoh/g, and peroxide value is less than 5.0meq/kg.Say
The bright present invention can obviously reduce Testa oryzae oil acid value and obtains the biodiesel rich in plant sterol ester.
Embodiment 7:
Substantially the same manner as Example 3, difference is: antarctic candidia lipase is by Pseudomonas cepacia Digestive Enzyme
Substitute；Testa oryzae oil is changed to Testa oryzae oil and Semen Tritici aestivi germ oil, and Testa oryzae oil, the quality of Semen Tritici aestivi germ oil respectively account for 1/2；Obtain rich in plant
The biodiesel of sterol ester, overall yield of reaction is more than 85%.Wherein plant sterol ester content is more than 50wt%, and acid value is less than
5.0mgkoh/g, peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Testa oryzae oil acid value and obtains rich in plant
The biodiesel of sterol ester.
Embodiment 8:
Substantially the same manner as Example 3, difference is: antarctic candidia lipase is by Pseudomonas cepacia Digestive Enzyme
Substitute；Testa oryzae oil is changed to Testa oryzae oil and Semen Tritici aestivi germ oil, and Testa oryzae oil, the quality of Semen Tritici aestivi germ oil respectively account for 1/2；Obtain rich in plant
The biodiesel of sterol ester, overall yield of reaction is more than 85%.Wherein plant sterol ester content is more than 50wt%, and acid value is less than
5.0mgkoh/g, peroxide value is less than 5.0meq/kg.Illustrate that the present invention can substantially reduce Testa oryzae oil acid value and obtain rich in plant
The biodiesel of thing sterol ester.
Embodiment 9:
Substantially the same manner as Example 1, difference is: high-acid value grease adopts Testa oryzae oil (moisture < 0.2wt%, acid value
20mgkoh/g) and Semen Tritici aestivi germ oil (moisture < 0.2wt%, acid value 100mgkoh/g), the quality of Testa oryzae oil and Semen Tritici aestivi germ oil
Respectively account for 1/2；Obtain rich in plant sterol ester biodiesel, overall yield of reaction is more than 88%.Wherein plant sterol ester content is more than
20wt%, product acid value is less than 6.0mgkoh/g, and peroxide value is less than 5.0meq/kg.Illustrate that the present invention can obviously reduce Testa oryzae
Oleic acid valency simultaneously obtains the biodiesel rich in plant sterol ester.
Each raw material cited by the present invention, and the bound of each raw material of the present invention, interval value, and technological parameter
The bound of (as temperature, time etc.), interval value can realize the present invention, embodiment numerous to list herein.
Claims (7)
1. a kind of using high valent acid vegetable oil produce rich in plant sterol ester biodiesel method it is characterised in that it include as
Lower step:
(1) input of reaction raw materials: by the free fatty in plant sterol, high acid value oils and fatss mol ratio be 1:1-5:1, point
The addition of son sieve is 100g/l, plant sterol, high acid value oils and fatss, molecular sieve is added in reactor, adds 100-200ppm
Antioxidant, is heated to 45-60 DEG C of stirring supersound process, and process time is 30-60 minute, obtains pre-composition；
Described plant sterol is stigmasterol, sitosterol, brassicasterol, any one or more than two kinds in campesterol by appointing
The mixture of meaning proportioning；
Described high valent acid vegetable oil include acid value in the Testa oryzae oil, Semen Tritici aestivi germ oil of 20-100mgkoh/g any one
Or more than the two kinds mixture by any proportioning, do not include waste grease；
(2) enzymatic interesterification procedure: add 5-40g/l Digestive Enzyme in pre-composition, in the range of 45-60 DEG C, stir under condition of normal pressure
Mix reaction 6-12h, stop heating, naturally cool to room temperature；
(3) post processing of product: after completion of the reaction, be centrifuged off Digestive Enzyme, molecular sieve, be filtered to remove not anti-after being cooled to 4 DEG C
The plant sterol answered, that is, obtain rich in plant sterol ester biodiesel.
2. a kind of utilization high valent acid vegetable oil according to claim 1 produces the side rich in plant sterol ester biodiesel
Method it is characterised in that: the raw material in step (1) needs pretreatment: 80 DEG C -120 DEG C vacuum drying 8-12h of plant sterol, plant steroid
The moisture of alcohol controls in below 1wt%, and the moisture of high acid value oils and fatss controls in below 0.2wt%.
3. a kind of utilization high valent acid vegetable oil according to claim 1 produces the side rich in plant sterol ester biodiesel
Method it is characterised in that: in step (1), raw material also includes reaction dissolvent, and plant sterol is 100- with the proportioning of reaction dissolvent
400mmol:1l, reaction dissolvent is added in reactor together with plant sterol, high acid value oils and fatss, molecular sieve；Reaction dissolvent adopts
Anhydrous sodium sulfate eliminating water, the moisture of reaction dissolvent controls in below 0.1wt%；In step (3), vacuum rotary steam removes dereaction
Solvent.
4. a kind of utilization high valent acid vegetable oil according to claim 3 produces the side rich in plant sterol ester biodiesel
Method it is characterised in that: described reaction dissolvent is normal hexane, isobutyltrimethylmethane., hexamethylene, one or two or more kinds is pressed and appoints in normal heptane
The mixture of meaning proportioning.
5. a kind of utilization high valent acid vegetable oil according to claim 1 produces the side rich in plant sterol ester biodiesel
Method it is characterised in that: described Digestive Enzyme is free or immobilized form, including the gauffer vacation silk from fermentable
Yeast-lipase, Candida lipalytica Lipase, antarctic candidia lipase or Pseudomonas cepacia Digestive Enzyme.
6. a kind of utilization high valent acid vegetable oil according to claim 1 produces the side rich in plant sterol ester biodiesel
Method it is characterised in that: described antioxidant is natural complex e, fat-soluble tea polyphenol or l- ascorbyl palmitate.
7. a kind of utilization high valent acid vegetable oil according to claim 1 produces the side rich in plant sterol ester biodiesel
Method it is characterised in that: the power of described supersound process be 100w-300w, supersonic frequency be 25-40hz.
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| WO2017020143A1 (en) * | 2015-08-03 | 2017-02-09 | 于殿宇 | Method of biosynthesizing functional lipid using nano-magnetically immobilized enzyme for continuous targeted catalysis of phospholipid in soybean oil |
| CN106191142B (en) * | 2016-07-18 | 2018-08-14 | 中国农业科学院油料作物研究所 | A kind of preparation method of the biodiesel rich in phenolic acid structure ester |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102268464A (en) * | 2010-06-02 | 2011-12-07 | 河南工业大学 | Method for producing diglyceride with rice bran oil of high acid value |
| CN103352067A (en) * | 2013-08-04 | 2013-10-16 | 中国农业科学院油料作物研究所 | Method for preparing functional grease rich in phytosterol ester and diglyceride |
-
2014
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102268464A (en) * | 2010-06-02 | 2011-12-07 | 河南工业大学 | Method for producing diglyceride with rice bran oil of high acid value |
| CN103352067A (en) * | 2013-08-04 | 2013-10-16 | 中国农业科学院油料作物研究所 | Method for preparing functional grease rich in phytosterol ester and diglyceride |
Non-Patent Citations (2)
| Title |
|---|
| Enzymatic deacidification of the rice bran oil and simultaneous preparation of phytosterol esters-enriched functional oil catalyzed by immobilized lipase arrays;zheng mingming等;《RSC Adv 》;20150810;第5卷;第70073-70079页 * |
| Production of novel "functional oil" rich in diglycerides and phytosterol esters with "one pot" enzymatic transesterification;Ming ming zheng等;《Journal of agricultural and food chemistry》;20140512;第62卷;第5142-5148页 * |
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| CN104178531A (en) | 2014-12-03 |
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