CN109082447A - A kind of preparation method of the mixed ester rich in OPO structured lipid - Google Patents
A kind of preparation method of the mixed ester rich in OPO structured lipid Download PDFInfo
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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
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Abstract
The present invention provides a kind of preparation methods of mixed ester rich in OPO structured lipid, belong to technical field of organic synthesis, preparation method provided by the invention is using high oleic acid peanut oil as raw material, the fatty-acid ethyl ester or fatty acid obtained by alcoholysis or middle pressure hydrolysis is directly and palm stearin synthesizes the mixed ester rich in OPO structured lipid under the catalytic action of enzyme, reduce the purification step of oleic acid, process flow is shortened, the safety of product is improved.Embodiment statistics indicate that, it is respectively 46.35%/44.17%, 60.73%/57.60%, 5.67%/4.07% that the present invention, which uses in fatty-acid ethyl ester/fatty acid and the palm stearin mixed ester obtained rich in OPO structured lipid that OPO content (national standard is in terms of C52 content of triglyceride), 2 palmitinic acids account for all palmitic acid contents and three ester content of remaining palmitic acid, and product index is all satisfied the regulation of standard GB/T 30604-2015.
Description
Technical field
The present invention relates to technical field of organic synthesis, in particular to the preparation side of a kind of mixed ester rich in OPO structured lipid
Method.
Background technique
Human milk is the best foods source of baby, it is supplied to the nutrition of baby's general equilibrium, and the growth of baby is promoted to send out
It educates.Have 4% or so lipid in human milk, wherein sweet three esters proportion is 98% or more, it be Major Nutrient in human milk at
/ mono-, certain energy is provided for baby.The case where lacking due to some areas there are breast-feeding condition, it is unable to get breast milk
Fed infant is mainly using formula milk as substitute.But the structure of conventional formulation Fatty Acids In Milk Powder differed with human milk fat compared with
Greatly, it is unfavorable for infantile health growth.Therefore, a suitable babies ' formula milk powder and its important is selected.And bis- oleic acid -2- of 1,3-
Sweet three ester of palmitinic acid (OPO structured lipid) is used as a kind of novel human milk fat substituted product, and addition OPO structured lipid is reachable in formula milk
To the feeding effect of closest breast milk.
Its position for being synthesized by enzyme process transesterification and making fatty acid on glycerol molecule of OPO structured lipid rearrange and
, fatty acid the Nomenclature Composition and Structure of Complexes is more nearly human milk fat.Compared with conventional formulation milk powder, palm in OPO type formula milk
Acid is concentrated mainly on the position Sn-2 (content of 2 palmitinic acids is higher than 40%), can promote absorption of the human body to fatty acid, ensures proper
When energy supply, the effective possibility for reducing calcium soap and generating reduces infant's difficult defecation, and can improve infant for
Being absorbed and utilized for energy and minerals, reduces internal calcium and magnesium ion and the missing of other nutritional ingredients, promote baby physique and
The natural growth of bone.Therefore, OPO structured lipid being added in milk powder can play and feeding effect similar in breast milk.
Currently, someone provides oleic acid using tea oil and olive oil to synthesize OPO structured lipid, but at high cost, glyceride stock comes
Source is few；And being commercialized oleic acid is using compound lard as raw material, source not can be traced, and pressure hydrolysis fat obtained in grease warp
Acid need to increase production process through high temperature rectifying purified oil acid.
Summary of the invention
In view of this, it is an object of that present invention to provide a kind of preparation method of mixed ester rich in OPO structured lipid, the present invention
The preparation method of offer reduces the step of oleic acid purifies, shortens process, improve product using high oleic acid peanut oil as raw material
Safety and can be up to state standards.
The present invention provides a kind of preparation methods of mixed ester rich in OPO structured lipid, comprising the following steps:
1) high oleic acid peanut oil is obtained into reaction product through alcoholysis reaction or middle pressure hydrolysis；The high oleic acid peanut
Oily oleic acid content >=70%；The reaction product of the alcoholysis reaction is fatty-acid ethyl ester, and the reaction of medium pressure hydrolysis produces
Object is fatty acid；
2) it is carried out after reaction product, the palm stearin and Sn-1,3 specific lipases mixing obtained the step 1)
Ester exchange reaction obtains the mixed ester rich in OPO structured lipid.
Preferably, the temperature of alcoholysis is 60~80 DEG C in the step 1), and the time of alcoholysis is 1~3h.
Preferably, the temperature of middle pressure hydrolysis is 240~260 DEG C in the step 1), and the time of middle pressure hydrolysis is 8~10h.
Preferably, the pressure of middle pressure hydrolysis is 24~28kg/cm in the step 1)2。
Preferably, the temperature of ester exchange reaction is 50~90 DEG C in the step 2), time of ester exchange reaction is 1~
6h。
Preferably, reaction product and the molar ratio of palm stearin are 2:1~6:1 in the step 2).
Preferably, Sn-1 in the step 2), 3 specific lipases are that Novi believes immobilized lipase 40086, Novi
Believe immobilized lipase TL IM, the immobilization Candida Candida lipase of sp.99-125 or immobilized porcine pancreatic lipase.
Preferably, Sn-1 in the step 2), the quality of 3 specific lipases are the reaction product and palm stearin
The 2~10% of gross mass.
Advantageous effects: the present invention provides a kind of preparation method of mixed ester rich in OPO structured lipid, the present invention is mentioned
The preparation method of confession is using high oleic acid peanut oil as raw material, and the reaction product obtained by alcoholysis reaction or middle pressure hydrolysis can
Directly and palm stearin synthesizes the mixed ester rich in OPO structured lipid at Sn-1, the catalytic action of 3 specific lipases, saves
The purification step for having omited oleic acid, shortens process flow, improves the safety of product.Embodiment statistics indicate that, the present invention adopts
With fatty-acid ethyl ester/fatty acid, (national standard is sweet with C52 with OPO content in the mixed ester made from palm stearin rich in OPO structured lipid
Oily three ester content meters), 2 palmitinic acids account for all palmitic acid contents and three ester content of remaining palmitic acid is respectively
46.35%/44.17%, 60.73%/57.60%, 5.67%/4.07%, product index is all satisfied standard GB/T 30604-
2015 regulation.
Detailed description of the invention:
Fig. 1 is the flow chart of the preparation method of bis- sweet three ester of oleic acid -2- palmitinic acid of 1,3- in the present invention；
Fig. 2 is that the fatty acid of fatty-acid ethyl ester obtained in embodiment 1 forms gas chromatogram；
Fig. 3 is influence of the molar ratio of fatty-acid ethyl ester and palm stearin to synthetic effect in embodiment 1；
Fig. 4 is influence of the ester exchange reaction time to synthetic effect in embodiment 2；
Fig. 5 is influence of the enzyme content to synthetic effect in embodiment 3；
Fig. 6 is influence of the transesterification reaction temperature to synthetic effect in embodiment 4；
Fig. 7 is the tlc analysis figure of target product obtained in embodiment 5；
Fig. 8 is the gas chromatogram of target product obtained in embodiment 5；
Fig. 9 is that sweet three ester of target product obtained in embodiment 5 forms gas chromatogram；
Figure 10 is that sweet three esters bulk sample fatty acid forms gas chromatogram in target product obtained in embodiment 5；
Figure 11 is that Sn-2 fatty acid forms gas chromatogram in sweet three ester in target product obtained in embodiment 5；
Figure 12 is that the SFC of target product obtained in embodiment 5 varies with temperature curve；
Figure 13 is that sweet three ester of target product obtained in embodiment 6 forms gas chromatogram；
Figure 14 is that sweet three esters bulk sample fatty acid forms gas chromatogram in target product obtained in embodiment 6；
Figure 15 is that Sn-2 fatty acid forms gas chromatogram in sweet three ester in target product obtained in embodiment 6.
Specific embodiment
The present invention provides a kind of preparation methods of mixed ester rich in OPO structured lipid, comprising the following steps:
1) high oleic acid peanut oil is obtained into reaction product through alcoholysis reaction or middle pressure hydrolysis；The high oleic acid peanut
Oily oleic acid content >=70%；The reaction product of the alcoholysis reaction is fatty-acid ethyl ester, and the reaction of medium pressure hydrolysis produces
Object is fatty acid；
2) it is carried out after reaction product, the palm stearin and Sn-1,3 specific lipases mixing obtained the step 1)
Ester exchange reaction obtains the mixed ester rich in OPO structured lipid.
High oleic acid peanut oil through alcoholysis reaction or middle pressure hydrolysis, is obtained reaction product by the present invention；The high oleic acid
Peanut oil oleic acid content >=70%；The reaction product of the alcoholysis reaction be fatty-acid ethyl ester, medium pressure hydrolysis it is anti-
Answering product is fatty acid.
In the present invention, the temperature of the alcoholysis is preferably 60~80 DEG C, and more preferably 65~75 DEG C；The alcoholysis when
Between preferably 1~3h, more preferably 1.5~2.5h.
In the present invention, the alcoholysis preferably carries out under agitation.The present invention does not have special limit to the method for stirring
It is fixed, select stirring means well known to those skilled in the art.
In the present invention, the alcoholysis carries out alcoholysis after preferably mixing high oleic acid peanut oil, ethyl alcohol and sodium hydroxide,
Obtain fatty-acid ethyl ester.
In the present invention, the mass ratio of the high oleic acid peanut oil, ethyl alcohol and sodium hydroxide is preferably 200:60~100:
1, more preferably 200:75~85:1.
The present invention further preferably includes that the reaction solution after alcoholysis is successively evaporated under reduced pressure, is layered, washes and is dehydrated, and is obtained
Fatty-acid ethyl ester.
In the present invention, the temperature of the vacuum distillation is preferably 40~60 DEG C, and more preferably 45~55 DEG C；The decompression
The time of distillation is preferably 0~60min, more preferably 40~50min, and the pressure of the vacuum distillation is preferably 0.03~
0.05kg/cm2, more preferably 0.035~0.045kg/cm2.The present invention is by being evaporated off excessive ethyl alcohol.
In the present invention, the liquid after distillation is preferably placed in stratification in separatory funnel by the layering, is obtained
Layer liquid.The present invention isolates the sodium hydroxide, glycerol and soap of lower layer by stratification.
In the present invention, the washing preferably washes supernatant liquid.
In the present invention, the washing is preferably washed with 50 DEG C of distilled water.The present invention does not have the number of washing
There are particular determination, washing to neutrality.
In the present invention, the dehydration is preferably dehydrated the supernatant liquid vacuum rotary steam after washing.
In the present invention, the temperature of the vacuum rotary steam is preferably 70~90 DEG C, and more preferably 75~85 DEG C；The decompression
The time of revolving is preferably 80~100min, more preferably 85~95min, and the pressure of the vacuum rotary steam is preferably 0.03~
0.05kg/cm2, more preferably 0.035~0.045kg/cm2。
In the present invention, the temperature of medium pressure hydrolysis is preferably 240~260 DEG C, and more preferably 240~255 DEG C；It is described
The time of middle pressure hydrolysis is preferably 8~10h；More preferably 8~9h；The pressure of medium pressure hydrolysis is preferably 24~28kg/
cm2, more preferably 24~27kg/cm2。
In the present invention, hydrolysis is pressed in progress after medium pressure hydrolysis preferably mixes high oleic acid peanut oil with water, is obtained
To fatty acid.
In the present invention, the volume ratio of the high oleic acid peanut oil and water is preferably 1:1.
In the present invention, the temperature of medium pressure hydrolysis is preferably 240~255 DEG C；The pressure of medium pressure hydrolysis is preferred
For 24~27kg/cm2, the time of medium pressure hydrolysis is preferably 8~9h.
The high oleic acid peanut oil mid-oleic that the present invention selects is preferably >=70%, more preferably 75~80%.
In the present invention, it is provided according to GB 30604-2015 standard, OPO is with edible vegetable oil oleic acid (from edible
Vegetable oil) it is to be made under raw material, then the catalytic action of enzyme.Oleic acid contains high oleic acid peanut oil in isolated product after hydrolysis
Amount reaches 75% or more, therefore, is suitable for and palm stearin and Sn-1,3 specific lipases after the hydrolysis of high oleic acid peanut oil
Ester exchange reaction is carried out after mixing, obtains the mixed ester rich in OPO structured lipid.
After obtaining reaction product, the present invention is preferably by the reaction product arrived, palm stearin and Sn-1,3 specificity fat
Ester exchange reaction is carried out after enzyme mixing, obtains the mixed ester rich in OPO structured lipid.
In the present invention, the temperature of the ester exchange reaction is preferably 50~90 DEG C, and more preferably 55~70 DEG C, most preferably
It is 60 DEG C；The time of the ester exchange reaction is preferably 1~6h, more preferably 1~3h, most preferably 1h.
In the present invention, reaction product and the molar ratio of palm stearin are preferably 2:1~6:1, more preferably 3:1~5:1；
Most preferably 5:1.
In the present invention, the Sn-1,3 specific lipases are preferably Novi's letter immobilized lipase 40086, Novi
Believe immobilized lipase TL IM, the immobilization Candida Candida lipase of sp.99-125 or immobilized porcine pancreatic lipase.
In the present invention, the Sn-1, the quality of 3 specific lipases are the reaction product and palmitic acid tristearin gross mass
2~10%, more preferably 5~8%, most preferably 6%.
It in the present invention, further preferably include molecular distillation after the ester exchange reaction.
In the present invention, the temperature of the molecular distillation is preferably 150~210 DEG C, more preferably 160~200 DEG C, described
The time of molecular distillation is preferably 30~90min, more preferably 50~80min.
Fatty acid or fatty-acid ethyl ester is evaporated off by molecular distillation in the present invention.
Fig. 1 is the flow chart of the preparation method of the mixed ester of the structured lipid containing OPO in the present invention.
For a better understanding of the present invention, below with reference to the embodiment content that the present invention is furture elucidated, but it is of the invention
Content is not limited solely to the following examples.
Embodiment 1
1) 2.16g NaOH is weighed in 1000mL three-necked flask, and 160g dehydrated alcohol and 432g high oleic acid peanut is added
Oil, under nitrogen protection in 75 DEG C of oil bath magnetic agitation 1.5h.End of reaction is cooled to room temperature, and vacuum rotary steam removes excessive
Ethyl alcohol is subsequently poured into stratification in separatory funnel, isolates the sodium hydroxide of lower layer, glycerol and soap, is washed with 50 DEG C of distillations
To neutrality, vacuum rotary steam dehydration obtains reaction product fatty-acid ethyl ester, is fitted into 500mL sample bottle, nitrogen charging gas shielded is simultaneously put into
It is spare in refrigerator.
It 2) is in molar ratio respectively that 2:1,3:1,4:1,5:1,6:1 weigh fatty-acid ethyl ester that step 1) obtains and palm is hard
Rouge, wherein palm stearin is 20g, 0.0225mol.Load weighted fatty-acid ethyl ester and palm stearin are placed in tri- mouthfuls of 250mL burnings
In bottle, in oil bath magnetic agitation (400r/min) to dissolving each other completely, it is incorporated as the 8% of fatty-acid ethyl ester and palm stearin gross mass
40086 lipase of Novozyme, 70 DEG C of reaction 4h.Distillation obtains target product.
The fatty-acid ethyl ester obtained with 1mL n-hexane dissolution 50mg, with spotting needle draw solution o'clock to 20 × 20cm thin layer
On chromatosheet, it is unfolded with solvent (n-hexane: ether: glacial acetic acid=80:20:2, v/v/v), after expansion completely, taking-up is dried,
Sweet three esters band, simple esterification, air inlet facies analysis are taken after being developed the color with 2 ', 7 '-dichlorofluoresceins.
Usable floor area normalization method analyzes each fatty acid relative amount in fatty-acid ethyl ester, calculates fatty acid phase by formula (1)
To content:
Fig. 2 is that the fatty acid of fatty-acid ethyl ester obtained in embodiment 1 forms gas chromatogram.
Table 1 is the fatty acid composition and relative amount of fatty-acid ethyl ester obtained in embodiment 1.
The fatty acid group and relative amount of fatty-acid ethyl ester obtained in 1 embodiment 1 of table
What C16:0 was represented is palmitinic acid；C18:0 is stearic acid；C18:1 is oleic acid；C18:2 is linoleic acid；C20:0 is colored
Raw acid；C20:1 is peanut monoenoic acid；C22:0 is behenic acid；C22:1 is erucic acid；C24:0 is lignoceric acid.
By Fig. 2, table 1 and combine formula (1) it is found that high oleic acid peanut oil fatty acid ethyl ester mid-oleic is up to
78.08%, it can be used as the desirable feedstock of synthesis OPO.
Table 2 is the physical and chemical index of fatty-acid ethyl ester obtained in embodiment 1.
The physical and chemical index of fatty-acid ethyl ester obtained in 2 embodiment 1 of table
As shown in Table 2, the physical and chemical index of fatty-acid ethyl ester obtained in embodiment 1 is preferable, can be used as the ideal of synthesis OPO
Raw material.
Fig. 3 is influence of the molar ratio of fatty-acid ethyl ester and palm oil fatty acid methyl ester to synthetic effect in embodiment 1.
From the figure 3, it may be seen that substrate molar ratio, during 2:1 increases to 6:1, OPO content, 2 palmitinic acids account for all palms
Acid content first increases then stable, and palmitic acid content is first reduced to be stablized afterwards；Substrate molar ratio increases to 5:1 by 2:1, and OPO content is aobvious
It writes and increases, this is because oleic acid concentration increases, reaction is promoted to carry out to positive reaction direction；Substrate molar ratio is continued growing to 6:1
When, the content for synthesizing OPO changes without conspicuousness, stablizes 41.14% or so, 2 palmitinic acids account for all palmitic acid contents at this time
Stablize 48% or so, palmitic acid content is stablized 4.7% or so, and excessive ethyl oleate is unfavorable for the separation of product, together
Shi Zengjia production cost, therefore the optimal selection of substrate molar ratio is 5:1.
Embodiment 2
The molar ratio of fatty-acid ethyl ester and palm oil fatty acid methyl ester be 5:1, the time of ester exchange reaction be respectively 30min, 1h, 2h,
4h,6h.Other reaction conditions are same as Example 1.Obtain target product.
Fig. 4 is influence of the ester exchange reaction time to synthetic effect in embodiment 2.
As shown in Figure 4, the reaction time, OPO content, 2 palmitinic acids accounted for all palmitinic acids during 30min increases to 6h
Content first increases to be reduced afterwards, and three ester content of palmitic acid is first reduced to be stablized afterwards.When increasing to 1h by 30min with the reaction time,
It reacts and is carried out to positive reaction direction, react more abundant, target product content dramatically increases, and reaction reaches balance in 1h,
OPO content is that account for all palmitic acid contents be 56.29% to 44.07%, 2 palmitinic acid, and the two content is maximum value, brown at this time
Palmitic acid acid content is 6.07%；In the reaction time between 1h~4h, with the increase in reaction time, OPO occurs in reaction process
Acyl group transfer, by-products content increase, and 2 palmitinic acids account for all palmitic acid contents and significantly reduce, and palmitic acid content becomes without significant
Change；When increasing to 6h by 4h between when reacted, since the by-product of acyl group transfer production is in Sn-1, the catalytic action of 3 lipase
Lower to react with palm stearin, causing OPO content and 2 palmitinic acids to account for all palmitic acid contents significantly reduces.Of the invention
Reaction time is short, high financial profit, guarantees preferably save power and the energy while product yield, it is contemplated that product yield
And power is saved, the optimal selection in reaction time is 1h.
Embodiment 3
With palm stearin in molar ratio it is that 5:1 is mixed by fatty-acid ethyl ester that 1 step 1) of embodiment obtains, is separately added into matter
Measure 2% that score is fatty-acid ethyl ester and palm oil fatty acid methyl ester gross mass, 4%, 6%, 8%, 10% 40086 fat of Novozyme
Enzyme, 70 DEG C of ester exchange reaction 1h.Other conditions are same as Example 1, obtain target product.
Fig. 5 is influence of the enzyme content to synthetic effect in embodiment 3.As shown in Figure 5, enzyme concentration increases to 10% 2%
In the process, OPO content, 2 palmitinic acids account for all palmitic acid contents and first increase stablizes afterwards, and palmitic acid content is first reduced to be stablized afterwards；
As enzyme concentration increases to 6% by 2%, enzyme-to-substrate contact area increases, positive reaction progress faster, reacts more abundant, target
Product assay dramatically increases；Change to 10%, OPO content without conspicuousness with enzyme concentration is increased, stablize 44.11% or so,
2 palmitinic acids account for all palmitic acid contents and stablize 56.37% or so at this time, and palmitic acid content is stablized 5.96% or so.This
Be be reacted into stable state because increasing to certain value when enzyme quantity, meanwhile, excessive lipase will increase the rate of back reaction.
Suitable lipase can reduce the generation of by-product just, reduce production cost under the premise of guaranteeing reaction rate.Synthesis is examined
Consider, the enzyme concentration optimal selection of reaction is 6%.
Embodiment 4
With palm stearin in molar ratio it is that 5:1 is mixed by fatty-acid ethyl ester that 1 step 1) of embodiment obtains, quality point is added
Number is 6% 40086 lipase of Novozyme of the gross masses of fatty-acid ethyl ester and palm stearin, respectively 50 DEG C, 60 DEG C,
1h is reacted at 70 DEG C, 80 DEG C and 90 DEG C, other conditions are same as Example 1.Obtain target product.
Fig. 6 is influence of the transesterification reaction temperature to synthetic effect in embodiment 4.It will be appreciated from fig. 6 that temperature is increased at 50 DEG C
During 90 DEG C, OPO content, which first increases, then to be reduced, and 2 palmitinic acids, which account for all palmitic acid contents and first tend towards stability, then to be reduced,
Three ester content of palmitic acid, which first reduces, then to be increased.When increasing to 60 DEG C by 50 DEG C with temperature, palm stearin is completely dissolved,
Increase with the intersolubility of ethyl oleate, enzyme is sufficiently mixed with reaction substrate, and positive reaction rate increases, and OPO content dramatically increases.For
(46.32 ± 0.03) %, three ester content of palmitic acid significantly reduce；When increasing to 80 DEG C by 60 DEG C with temperature, OPO content
All palmitic acid contents are accounted for 56.58% or so in 43.64% or so, 2 palmitinic acid, and palmitic acid content is 6.25% or so.
Continue to increase temperature, the stability of part enzyme is destroyed, while the acyl migration enhancing in lipase-catalyzed reaction, OPO contain
Amount and 2 palmitinic acids account for all palmitic acid contents and significantly reduce, and three ester content of palmitic acid significantly increases.According to Novozyme
The requirement of 40086 enzymes, we select optimal reaction temperature for 60 DEG C.
Embodiment 5
It with palm stearin is in molar ratio that 5:1 is mixed by fatty-acid ethyl ester that 1 step 1) of embodiment obtains, wherein palm is hard
Rouge is 20g, 0.0225mol, and 8% Novozyme of the gross mass that mass fraction is fatty-acid ethyl ester and palm stearin is added
40086 lipase, react 2h at 70 DEG C, and other conditions are same as Example 1.Obtain target product.
Tlc analysis is carried out to target product obtained in embodiment 5, result is as shown in Figure 7.Right side be glyceride and
The standard specimen of ethyl oleate blend, left side are target product obtained in embodiment 5.
Fig. 8 is the gas chromatogram of target product obtained in embodiment 5.
Table 3 is the composition and relative amount of target product obtained in embodiment 5.
The composition and relative amount of target product obtained in 3 embodiment 5 of table
As Fig. 7, Fig. 8 and table 3 it is found that the fatty acid and ethyl ester content of target product obtained in embodiment 5 are few, big portion
It is divided into diglyceride and sweet three ester.
Fig. 9 is that sweet three ester of target product obtained in embodiment 5 forms gas chromatogram.
Table 4 is the composition and relative amount of sweet three ester of target product obtained in embodiment 5.
The composition and relative amount of sweet three ester of target product obtained in 4 embodiment 5 of table
It is analyzed by Fig. 9 and table 4 it is found that being made up of gas chromatograph to sweet three ester, obtains the relative amount of C52,
The result (C52 is 40% or so) studied with national standard (C52 >=40%) and some scholars compares, and obtains and obtains in embodiment 5
Target product OPO structured lipid content it is higher, remaining three ester content of palmitic acid is less, meets national standard.
Figure 10 is that sweet three esters bulk sample fatty acid forms gas chromatogram in target product obtained in embodiment 5.
Table 5 is sweet three esters bulk sample fatty acid composition and relative amount in target product obtained in embodiment 5.
Sweet three esters bulk sample fatty acid composition and content in target product obtained in 5 embodiment 5 of table
Figure 11 is that Sn-2 fatty acid forms gas chromatogram in sweet three ester in target product obtained in embodiment 5；
Table 6 is Sn-2 fatty acid composition and content in sweet three ester in target product obtained in embodiment 5.
In target product obtained in 6 embodiment 5 of table in sweet three ester Sn-2 fatty acid composition and relative amount
Sn- in the target product obtained when it is found that reaction temperature being 60 DEG C in embodiment 5 by Figure 10, table 5, Figure 11 and table 6
2 palmitinic acids reach 58.3%, bulk sample oleic acid content 52.2%, and oleic acid insertion rate is higher.
Figure 12 is that the SFC of target product obtained in embodiment 5 varies with temperature curve.
As shown in Figure 12, the SFC of target product sharply declines at 10~30 DEG C, and the SFC of OPO is down to by 30.968%
2.874%, illustrate that the sweet three esters fusing point for forming OPO concentrates between 10~30 DEG C, this is molten with unsaturated sweet three ester of a saturation two
The range of point is consistent (1~23 DEG C).Because still containing a small amount of higher melting-point palm stearin in target product, at 30 DEG C
Still contain minimal amount of solid fat between~45 DEG C, content is 0.203% or so.
To sum up, the physical and chemical index of target product obtained in embodiment 5 is as shown in table 7.
The physical and chemical index of target product obtained in 7 embodiment 5 of table
As shown in Table 7, target product obtained in embodiment 5 is the mixed ester rich in OPO structure ester, and reaches national mark
It is quasi-.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Embodiment 6
6:1 weighs the high oleic acid peanut oil free fatty acid and palm stearin that middle pressure hydrolysis obtains in molar ratio, wherein palm fibre
Palmitic acid tristearin is 20g, 0.0225mol.Load weighted free fatty acid and palm stearin are placed in 250mL three-necked flask, in oil
Magnetic agitation (400r/min) is bathed to dissolving each other completely, is incorporated as the 10% of free fatty acid and palm stearin gross mass
40086 lipase of Novozyme, 70 DEG C of reaction 4h.Distillation obtains target product.
Figure 13 is that sweet three ester of target product obtained in embodiment 6 forms gas chromatogram.
Table 8 is the composition and relative amount of sweet three ester of target product obtained in embodiment 6
The composition and relative amount of sweet three ester of target product obtained in 8 embodiment 6 of table
As Figure 13 and table 8 it is found that target product OPO structured lipid content obtained in embodiment 6 is greater than 40%, remaining palm
Acid glycerol three ester content is less, meets national standard.
Figure 14 is that sweet three esters bulk sample fatty acid forms gas chromatogram in target product obtained in embodiment 6.
Table 9 is sweet three esters bulk sample fatty acid composition and relative amount in target product obtained in embodiment 6.
Sweet three esters bulk sample fatty acid composition and content in target product obtained in 9 embodiment 6 of table
Figure 15 is that sweet three esters Sn-2 fatty acid forms gas chromatogram in target product obtained in embodiment 6.
Table 10 is Sn-2 fatty acid composition and relative amount in sweet three ester in target product obtained in embodiment 6.
In target product obtained in 10 embodiment 6 of table in sweet three ester Sn-2 fatty acid composition and relative amount
As Figure 14, Figure 15, table 10 and table 10 it is found that sn-2 palmitinic acids reach in target product obtained in embodiment 6
55.89%, bulk sample oleic acid content 50.18%.
To sum up, the physical and chemical index of target product obtained in embodiment 6 is as shown in table 11.
The physical and chemical index of target product obtained in 11 embodiment 6 of table
As chart 11 it is found that target product obtained in embodiment 6 is the mixed ester rich in OPO structure ester, and reach state
Family's standard.
The above is only an embodiment of the invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (8)
1. a kind of preparation method of the mixed ester rich in OPO structured lipid, comprising the following steps:
1) high oleic acid peanut oil is obtained into reaction product through alcoholysis reaction or middle pressure hydrolysis；The high oleic acid peanut oil
Oleic acid content >=70%；The reaction product of the alcoholysis reaction is fatty-acid ethyl ester, the reaction product of medium pressure hydrolysis
For fatty acid；
2) ester friendship is carried out after reaction product, the palm stearin and Sn-1,3 specific lipases mixing obtained the step 1)
Reaction is changed, the mixed ester rich in OPO structured lipid is obtained.
2. preparation method according to claim 1, which is characterized in that the temperature of alcoholysis is 60~80 in the step 1)
DEG C, the time of alcoholysis is 1~3h.
3. preparation method according to claim 1, which is characterized in that the temperature of middle pressure hydrolysis is 240 in the step 1)
~260 DEG C, the time of middle pressure hydrolysis is 8~10h；Amount of water is 1~1.2 times of grease.
4. preparation method according to claim 1 or 3, which is characterized in that the pressure of middle pressure hydrolysis is in the step 1)
24~28kg/cm2。
5. preparation method according to claim 1, which is characterized in that the temperature of ester exchange reaction is 50 in the step 2)
~90 DEG C, the time of ester exchange reaction is 1~6h.
6. preparation method according to claim 1, which is characterized in that reaction product and palm stearin in the step 2)
Molar ratio is 2:1~6:1.
7. preparation method according to claim 1, which is characterized in that Sn-1 in the step 2), 3 specific lipases
Believe that immobilized lipase 40086, Novi believe immobilized lipase TL IM, immobilization Candida Candida for Novi
125 lipase of sp.99-or immobilized porcine pancreatic lipase.
8. preparation method according to claim 1 or claim 7, which is characterized in that Sn-1 in the step 2), 3 specificity rouge
The quality of fat enzyme is the 2~10% of the reaction product and palm stearin gross mass.
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| WO2022045953A1 (en) * | 2020-08-31 | 2022-03-03 | Aak Ab (Publ) | A process for production of a vegetable oil composition having at least 50% palmitic acid present in the sn2-position out of total palmitic acid in the triglycerides of the vegetable oil composition |
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