CN106480116A - A kind of method of enzymatic clarification 1,3 distearyl acid 2 oleins - Google Patents
A kind of method of enzymatic clarification 1,3 distearyl acid 2 oleins Download PDFInfo
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- CN106480116A CN106480116A CN201610403577.6A CN201610403577A CN106480116A CN 106480116 A CN106480116 A CN 106480116A CN 201610403577 A CN201610403577 A CN 201610403577A CN 106480116 A CN106480116 A CN 106480116A
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
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Abstract
The invention discloses a kind of enzymatic clarification 1; the method of 3 distearyl acid 2 oleins; by high oleic acid vegetable oil and stearic acid acry radical donor with certain substrate mixed in molar ratio; under dicyandiamide solution or solvent-free system; add a certain amount of Digestive Enzyme; react 1～10h at 60～80 DEG C, obtain the product containing SOS.The present invention by using the specificity of enzyme, high efficiency and controls reaction condition to suppress acyl migration side reaction; reaction conversion ratio is very high; simultaneously; also shorten generated time; whole process is easily controllable, and reaction condition is gentle, simultaneously by substantially reducing cost to the recycling of enzyme; it is easy to large-scale industrialization promotion, its application potential is huge.
Description
Technical field
The invention belongs to the development technique field of special fat, it is related to a kind of enzymatic clarification 1,3- distearyl acid -2- Oleic acid
The method of glyceride (SOS).
Background technology
The cacao bean producing cocoa butter is grown on area within 20 ° of tropical equator north and south latitude degree.Due to geographical position and weather
Condition limit so that the yield of cocoa butter is far from the market demand meeting world's chocolate.In order to meet chocolate food
Demand, the research of cocoa butter substitutes flourished, the demand of wide market, especially developing country with
Day all increasings.In next existing industry standard of China, the regulation of national standard, cocoa butter substitutes have the interpolation of 10-15%
Amount extending space.Therefore wide consumption market and huge profit margin make cocoa butter substitutes have wide exploitation valency
Value.
Cocoa butter improver is a kind of cacaolike butter of heat resistant type, rich in the higher SOS of fusing point, can adjust natural cocoa
The soft or hard degree of fat, improve chocolate moisture-resisting hot with also to bloom ability etc. so as to become high-end chocolate product
Important adjuvant.By systematic study is carried out to the enzymatic clarification technique of cocoa butter improver, purifying process and physicochemical property, exploitation
Go out to solve the product of the problems referred to above of chocolate presence, there is obvious using value.
At present, prepare both at home and abroad more than cocoa butter improver using more traditional immobilized enzyme Lipozyme RM IM, solid
Surely change enzyme Novozym 435 etc., the SOS content obtaining is generally between 30～40%, and obtains with regard to probing into substrate comparison SOS
The impact of rate has no that pertinent literature is reported.
Content of the invention
The purpose of this part is to summarize some aspects of embodiments of the invention and briefly introduce some preferably to implement
Example.A little simplification may be done in this part and the description of the present application summary and denomination of invention or omit to avoid making our department
Point, the purpose of specification digest and denomination of invention obscure, and this simplify or omit cannot be used for limiting the scope of the present invention.
In view of problem present in above-mentioned and/or existing enzymatic clarification SOS is it is proposed that the present invention.
Therefore, it is an object of the invention to overcoming the deficiencies in the prior art, provide a kind of process is simple, yield high enzyme process
The method of synthesis SOS.
For solving above-mentioned technical problem, the invention provides following technical scheme：A kind of enzymatic clarification 1, the acid of 3- distearyl-
The method of 2- olein it is characterised in that mix high oleic acid vegetable oil with stearic acid acry radical donor with certain mol ratio
Close, in dicyandiamide solution or solvent-free system, add a certain amount of Digestive Enzyme, react 1～10h at 60～80 DEG C, contained
There is the product of SOS.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described high oleic acid vegetable oil includes, one of high oleic sunflower oil, high oleic acid Oleum Brassicae campestriss or high acid corn oil or
Several.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described stearic acid acry radical donor includes, one or more of stearic acid, methyl stearate or ethyl stearte.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described certain mol ratio is that high oleic acid vegetable oil is 1 with the mol ratio of stearic acid acry radical donor：2～16.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described high oleic acid vegetable oil is 1 with the mol ratio of stearic acid acry radical donor：12.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described dicyandiamide solution includes, one or more of hexane, petroleum ether, ethyl acetate or acetone.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described high oleic acid vegetable oil is 1 with the quality volume proportion of dicyandiamide solution:0～5.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described Digestive Enzyme includes, immobilized enzyme Lipozyme RM IM, immobilized enzyme Novozym435 or immobilized enzyme
One or more of NS40086.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：Described Digestive Enzyme is immobilized enzyme NS40086.
As enzymatic clarification 1 of the present invention, a kind of preferred version of the method for 3- distearyl acid -2- olein,
Wherein：The quality of described Digestive Enzyme is the 1%～15% of high oleic acid vegetable oil and stearic acid acry radical donor gross mass.
Beneficial effects of the present invention：The present invention by using the specificity of enzyme, high efficiency and controls reaction condition to press down
Acyl migration side reaction processed, reaction conversion ratio is very high, meanwhile, also shortens generated time, whole process is easily controllable, reacts bar
Part is gentle, simultaneously by substantially reducing cost to the recycling of enzyme, is easy to large-scale industrialization promotion, its application potential is huge
Greatly.Currently preferred new immobilized enzyme NS40086, is catalyzed Sn-1,3 specificitys are by force so that catalytic efficiency is very high；This
, so that reaction conversion ratio greatly improves, accounting in glycerol production three ester for the SOS is more than 70% for bright preferred substrate mol ratio；
Reaction condition of the present invention is gentle, and energy consumption is low, more environmentally friendly, by also substantially reducing cost, application potential to the recycling of enzyme
Huge.
Brief description
In order to be illustrated more clearly that the technical scheme of the embodiment of the present invention, below will be to required use in embodiment description
Accompanying drawing be briefly described it should be apparent that, drawings in the following description are only some embodiments of the present invention, for this
For the those of ordinary skill of field, without having to pay creative labor, other can also be obtained according to these accompanying drawings
Accompanying drawing.Wherein：
Fig. 1 is high oleic sunflower oil and stearic acid enzyme process product RP-HPLC liquid phase figure in embodiment 1.
Fig. 2 is high oleic acid Oleum Brassicae campestriss and stearic acid enzyme process product RP-HPLC liquid phase figure in embodiment 3.
Specific embodiment
Understandable for enabling the above objects, features and advantages of the present invention to become apparent from, with reference to specific embodiment pair
The specific embodiment of the present invention is described in detail.
Elaborate a lot of details in the following description in order to fully understand the present invention, but the present invention is acceptable
To be implemented different from alternate manner described here using other, those skilled in the art can be without prejudice to intension of the present invention
In the case of do similar popularization, therefore the present invention is not limited by following public specific embodiment.
Secondly, " embodiment " or " embodiment " referred to herein refers to may be included at least one realization side of the present invention
Special characteristic in formula, structure or characteristic.Different places occur in this manual " in one embodiment " not refers both to
Same embodiment, is not single or optionally mutually exclusive with other embodiment embodiment.
Embodiment 1
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high oleic sunflower oil
It is 1 with stearic mol ratio：12, by adding 10% immobilized enzyme NS40086, stirring reaction 6h at 70 DEG C of normal pressure.Reaction
After end, product by centrifugal sedimentation remove immobilized enzyme, after sample preparation enter chromatograph of liquid analysis, by with
SOS standard substance compare and determine that SOS content is 72.81%.As shown in figure 1, the triglyceride that three peaks of in figure represent successively is
OOO, SOO, SOS, under high substrate mol ratio, reaction conversion ratio is high.
Embodiment 2
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, high acid corn oil and methyl stearate mol ratio
For 1：4, high acid corn oil and the normal hexane ratio of interpolation are 1：4 (w/v), by adding 10% immobilized enzyme NS40086, often
Stirring reaction 6h at 75 DEG C of pressure.After reaction terminates, product removes immobilized enzyme by centrifugal sedimentation, enters after sample preparation
Chromatograph of liquid is analyzed, and is 43.18% by comparing determination SOS content with SOS standard substance.
Embodiment 3
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high oleic acid Oleum Brassicae campestriss and
Stearic acid mol ratio is 1：2, by adding 10% immobilized enzyme NS40086, stirring reaction 4h at 70 DEG C of normal pressure.Reaction terminates
Afterwards, product removes immobilized enzyme by centrifugal sedimentation, enters chromatograph of liquid analysis, by marking with SOS after sample preparation
Quasi- product compare and determine that SOS content is 23.77%.As shown in Fig. 2 the triglyceride that four peaks of in figure represent be OOL, OOO, SOO,
SOS, under low substrate mol ratio, reaction conversion ratio is low, leads to SOS yield relatively low.
Embodiment 4
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high acid corn oil and
Stearic acid mol ratio is 1：4, by adding 10% immobilized enzyme Lipozyme RM IM, stirring reaction 6h at 70 DEG C of normal pressure.Instead
After should terminating, product by centrifugal sedimentation remove immobilized enzyme, after sample preparation enter chromatograph of liquid analysis, by with
SOS standard substance compare and determine that SOS content is 38.29%.
Embodiment 5
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high oleic sunflower oil
It is 1 with ethyl stearte mol ratio：12, by adding 10% immobilized enzyme NS40086, stirring reaction 8h at 80 DEG C of normal pressure.Instead
After should terminating, product by centrifugal sedimentation remove immobilized enzyme, after sample preparation enter chromatograph of liquid analysis, by with
SOS standard substance compare and determine that SOS content is 60.34%.
Embodiment 6
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high oleic acid Oleum Brassicae campestriss and
Methyl stearate mol ratio is 1：8, by adding 10% immobilized enzyme NS40086, stirring reaction 10h at 60 DEG C of normal pressure.Reaction
After end, product by centrifugal sedimentation remove immobilized enzyme, after sample preparation enter chromatograph of liquid analysis, by with
SOS standard substance compare and determine that SOS content is 50.21%.
Embodiment 7
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high oleic sunflower oil
It is 1 with stearic acid mol ratio：8, by adding 2% immobilized enzyme NS40086, stirring reaction 10h at 60 DEG C of normal pressure.Reaction terminates
Afterwards, product removes immobilized enzyme by centrifugal sedimentation, enters chromatograph of liquid analysis, by marking with SOS after sample preparation
Quasi- product compare and determine that SOS content is 34.49%.
Embodiment 8
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high oleic sunflower oil
It is 1 with stearic acid mol ratio：6, by adding 10% immobilized enzyme NS40086, stirring reaction 6h at 70 DEG C of normal pressure.Reaction terminates
Afterwards, product removes immobilized enzyme by centrifugal sedimentation, enters chromatograph of liquid analysis, by marking with SOS after sample preparation
Quasi- product compare and determine that SOS content is 51.41%
Embodiment 9
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high acid corn oil and
Stearic acid mol ratio is 1：4, by adding 2% immobilized enzyme Novozym 435, stirring reaction 4h at 75 DEG C of normal pressure.Reaction knot
Shu Hou, product by centrifugal sedimentation remove immobilized enzyme, after sample preparation enter chromatograph of liquid analysis, by with SOS
Standard substance compare and determine that SOS content is 15.36%.
Embodiment 10
Batch (-type) enzyme reaction is carried out in batch-type agitator tank reactor, under solvent-free system, high acid corn oil and
Stearic acid mol ratio is 1：4, by adding 6% immobilized enzyme NS40086, stirring reaction 6h at 70 DEG C of normal pressure.After reaction terminates,
Product by centrifugal sedimentation remove immobilized enzyme, after sample preparation enter chromatograph of liquid analysis, by with SOS standard substance
Compare and determine that SOS content is 38.36%.
As can be seen here, the present invention has been used new immobilized enzyme NS40086 as the catalyst of reaction, and preferred substrate rubs
Your ratio so that catalytic efficiency, reaction conversion ratio and SOS yield are significantly increased, and by can be big to the recycling of enzyme
Big reduces cost, whole course of reaction process is simple, very friendly to environment, application potential is huge.
It should be noted that above example is only in order to illustrate technical scheme and unrestricted, although with reference to preferably
Embodiment has been described in detail to the present invention, it will be understood by those within the art that, can be to the technology of the present invention
Scheme is modified or equivalent, and without deviating from the spirit and scope of technical solution of the present invention, it all should be covered at this
In the middle of bright right.
Claims (10)
1. a kind of enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：By high oleic acid vegetable oil with
Stearic acid acry radical donor, with certain mixed in molar ratio, in dicyandiamide solution or solvent-free system, adds a certain amount of Digestive Enzyme,
React 1～10h at 60～80 DEG C, obtain the product containing SOS.
2. according to claim 1 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described height
Oleic vegetable oils include, one or more of high oleic sunflower oil, high oleic acid Oleum Brassicae campestriss or high acid corn oil.
3. according to claim 1 or 2 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described
Stearic acid acry radical donor includes, one or more of stearic acid, methyl stearate or ethyl stearte.
4. according to claim 1 or 2 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described
Certain mol ratio is that high oleic acid vegetable oil is 1 with the mol ratio of stearic acid acry radical donor：2～16.
5. according to claim 4 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that:Described height
Oleic vegetable oils are 1 with the mol ratio of stearic acid acry radical donor：12.
6. according to claim 1 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described molten
Agent system includes, one or more of hexane, petroleum ether, ethyl acetate or acetone.
7. according to claim 1 or 6 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described
High oleic acid vegetable oil is 1 with the quality volume proportion of dicyandiamide solution:0～5.
8. according to claim 1 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described fat
Fat enzyme includes, one of immobilized enzyme Lipozyme RM IM, immobilized enzyme Novozym 435 or immobilized enzyme NS40086
Or it is several.
9. according to claim 1 or 8 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Described
Digestive Enzyme is immobilized enzyme NS40086.
10. according to claim 1 or 8 enzymatic clarification 1, the method for 3- distearyl acid -2- olein it is characterised in that：Institute
The quality stating Digestive Enzyme is the 1%～15% of high oleic acid vegetable oil and stearic acid acry radical donor gross mass.
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| CN201610403577.6A CN106480116B (en) | 2016-06-08 | 2016-06-08 | A kind of enzymatic clarification 1, the method for 3- distearyl acid -2- olein |
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| CN201610403577.6A CN106480116B (en) | 2016-06-08 | 2016-06-08 | A kind of enzymatic clarification 1, the method for 3- distearyl acid -2- olein |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108935743A (en) * | 2018-05-18 | 2018-12-07 | 吕莉 | A kind of trans-fatty acid-free smears rouge and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101878821A (en) * | 2010-05-05 | 2010-11-10 | 江南大学 | The biosynthesis of cocoa butter improver |
| CN102634547A (en) * | 2012-03-28 | 2012-08-15 | 江南大学 | Preparation method of symmetric triglyceride |
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2016
- 2016-06-08 CN CN201610403577.6A patent/CN106480116B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101878821A (en) * | 2010-05-05 | 2010-11-10 | 江南大学 | The biosynthesis of cocoa butter improver |
| CN102634547A (en) * | 2012-03-28 | 2012-08-15 | 江南大学 | Preparation method of symmetric triglyceride |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108935743A (en) * | 2018-05-18 | 2018-12-07 | 吕莉 | A kind of trans-fatty acid-free smears rouge and preparation method thereof |
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