CN108117933A - A kind of method of 2 palmitic acid relative amounts in raising grease - Google Patents
A kind of method of 2 palmitic acid relative amounts in raising grease Download PDFInfo
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- CN108117933A CN108117933A CN201611071892.XA CN201611071892A CN108117933A CN 108117933 A CN108117933 A CN 108117933A CN 201611071892 A CN201611071892 A CN 201611071892A CN 108117933 A CN108117933 A CN 108117933A
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- China
- Prior art keywords
- opo
- products
- acid
- palmitic acid
- lipase
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
- C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Abstract
The present invention provides a kind of method for improving 2 palmitic acid relative amounts in grease.Specifically, the present invention provides two palmitic acid relative amounts and/or 1 in a kind of raising OPO products, and the method for 3 two oleic acid, 2 palmitic acid, three ester content, the described method includes described in partial glyceride lipase and water process the step of OPO products.Present invention additionally comprises a kind of OPO product preparation methods, the described method includes using two palmitic acid relative amounts and/or 1 in raising OPO products as described herein, the method of 3 two oleic acid, 2 palmitic acid, three ester content is to improve two palmitic acid relative amounts and/or 1 in the OPO products, the step of 3 two oleic acid, 2 three ester content of palmitic acid.2 palmitic acid relative amounts of OPO products and 1,3 two oleic acid, 2 palmitic acid, three ester content in terms of C52 can be further improved using the method for the present invention.
Description
Technical field
The present invention relates to fats and oils processing fields, and in particular to a kind of method for improving 2 palmitic acid relative amounts in grease.
Background technology
Bis- oleic acid -2- palmitic acids of 1,3-, three ester (OPO) is the main feature ingredient of human milk fat.At present, OPO has become
For a kind of new nutrition fortifier, it is added in baby formula milk powder, realize from aliphatic acid composition and is distributed as far as possible
Imitate human milk fat.
(GB30604-2015) is provided in the food enrichment OPO national standards of 2015 Nian9Yue China issue, OPO
Two palmitic acids account for all palmitic acid contents and are greater than 52% in product, 1,3-Dioleic acid-2-palmitoyl triglyceride content (with
C52 is counted) it is higher than 40%.It is to use vegetable oil with oleic acid (from edible vegetable oil and fat) for original that OPO is also indicated that in standard
Material, is made through food industry with lipase-catalyzed transesterification.
At present, it has been disclosed that the major technique for preparing OPO include it is following several：
CN101258230 discloses a kind of method for preparing OPO, uses palm oil stearin and oleic acid of the iodine number for 2-12
Or the ester of its nonglyceride carries out enzymatic interesterification procedure preparation.
CN101679909 discloses a kind of method for preparing OPO, using the palmitic stearin of iodine number 18-40, is carried out
Random ester exchange reaction, then carry out enzymatic interesterification procedure preparation with the ester of oleic acid or its nonglyceride.
CN102827885 discloses a kind of method for preparing OPO, using the ester rich in saturated fatty acid residues and rich in not
The ester of saturated fatty acid residues carries out random ester exchange reaction, then carries out enzyme process orientation transesterification with unrighted acid or its ester
It is prepared by reaction.
CN101198261 discloses a kind of method for preparing OPO, using the vegetable triglyceride of enzymatic randomization with dissociating
Unsaturated fat acid source reacts preparation in the presence of insoluble catalyst.
CN102776077 discloses a kind of method for preparing OPO, is being urged using palm oil of the palmitic acid content more than 50%
The lower progress intramolecular of agent effect retakes reaction, then with the ester of fatty acid mixed or its nonglyceride in 1,3 specificity fat
Ester exchange reaction preparation is carried out under enzyme effect.
Application disclosed above mainly concentrates on the raw material and method for being used to prepare OPO, using different raw materials and side
Method can obtain satisfactory OPO products, not pay close attention to and the subsequent processing refining process of OPO.
OPO products generally remove the aliphatic acid in mixture using molecular distillation at present, then using traditional grease essence
Sweetening process is processed.
Although two palmitic acid relative amounts are more than 52% in national regulations OPO products, how to further improve
Two palmitic acid relative amounts are always the hot spot of this field research in OPO products.
The content of the invention
Be not only restricted to OPO prepares raw material and technique, and the present invention has been found surprisingly that one kind can further improve OPO productions
The method of 2 palmitic acid relative amounts in product can further improve 2 palmitic acid relative amounts of OPO products using this method
(content of 2 palmitic acids i.e. in terms of all palmitic acids in OPO products) and 1,3-Dioleic acid-2-palmitoyl triglyceride
Content (in terms of C52, is shown in the definition in GB30604-2015).
Therefore, first aspect present invention provides a kind of method for improving two palmitic acid relative amounts in OPO products, described
Method includes the step of OPO products described in partial glyceride lipase and water process.
Second aspect of the present invention provides bis- oleic acid -2- palmitic acids of 1,3-, three ester content in a kind of raising OPO products
Method, the described method includes described in partial glyceride lipase and water process the step of OPO products.
Third aspect present invention also provides a kind of OPO product preparation methods, and the described method includes with partial glyceride lipase
With described in water process the step of OPO products.
In one or more embodiments of above-mentioned aspect, the partial glyceride lipase is derived from aspergillus
(Aspergillus), the lipase of Penicillium (Penicillium) or Marxist philosophy lesson (Malassezia).
In one or more embodiments of above-mentioned aspect, the partial glyceride lipase is derived from sramana cypress cheese green grass or young crops
The lipase of mould (Penicillium camemberti) or penicillium cyclopium (Penicillium cyclopium).
In one or more embodiments of above-mentioned aspect, the partial glyceride lipase is lipase G50.
In one or more embodiments of above-mentioned aspect, the additive amount of the lipase is every gram of pending OPO production
The enzyme of 5~500U of product.
In one or more embodiments of above-mentioned aspect, the additive amount of the water is pending OPO product weights
More than 0.1%.
In one or more embodiments of above-mentioned aspect, the additive amount of the water is pending OPO product weights
0.1~30%.
In one or more embodiments of above-mentioned aspect, the processing is excellent to be stirred at a temperature of 10~50 DEG C
20~50 DEG C are selected in, more preferably 30~40 DEG C.
In one or more embodiments of above-mentioned aspect, when the time of stirring is 1~30 small.
In one or more embodiments of above-mentioned aspect, the OPO products are hair OPO products.
In one or more embodiments of above-mentioned aspect, the OPO products are triglyceride mixture, wherein with this
Total palmitic acid meter contained by OPO products, the content of the palmitic acid on Sn-2 positions are more than 30%；15~55% fat in total fatty acids
Fat acid is palmitic acid.
In one or more embodiments, in terms of total palmitic acid contained by the OPO products, palmitic acid on Sn-2 positions
Content is more than 45%.
In one or more embodiments of above-mentioned aspect, the processing carries out or before hair OPO product depicklings in hair
It is carried out after OPO product depicklings.
In one or more embodiments of above-mentioned aspect, further included after the processing in alkali refining, decoloration and deodorization
One or more steps.
In one or more embodiments of above-mentioned aspect, the OPO products are refining OPO products.
Fourth aspect present invention provides a kind of OPO products, in the OPO products, in terms of the weight of all palmitic acids, and two palm fibres
The content of palmitic acid acid is more than 30%；The aliphatic acid of 15~55wt% is palmitic acid in total fatty acids；Preferably, 1,3- in terms of C52
Two oleic acid -2- palmitic acids, three ester content is more than 36%, more preferably more than 40%.
In one or more embodiments, the OPO products are prepared using herein described method.
Specific embodiment
The present invention by using partial glyceride lipase and water process OPO products 2 palmitic acid relative amounts and/or with
The method of bis- oleic acid -2- palmitic acids of 1,3-, three ester content of C52 meters.
OPO products suitable for the method for the present invention can be various OPO products well known in the art, can be a mao OPO productions
Product or refining OPO products.In the present invention, hair OPO products refer to the product of transesterification acquisition, can be handled through depickling or not
It is handled through depickling.Refining OPO products refer to the OPO products through depickling, decoloration and/or deodorization processing.
It is not only restricted to it suitable for the OPO products of the method for the present invention and prepares raw material and technique.For example, it can be used palm oil hard
Transesterification grease is prepared under the action of catalyst (such as sodium methoxide) with high oleic sunflower oil in fat essence, then by the ester
It exchanges grease and progress enzyme process transesterification is mixed with oleic acid, so as to which the OPO products for the method for the present invention be prepared.In another example
Palm oil stearin is made to react under the action of catalyst (such as sodium methoxide), obtains transesterification grease, then hands over the ester
Fat of changing oil carries out enzyme process transesterification with oleic acid, so as to which the OPO products for being suitable for the method for the present invention be prepared.In another example it can make
Palm oil reacts under the action of catalyst (such as sodium methoxide), and transesterification grease is prepared, then by the ester-exchanged oil
Fat carries out enzyme process transesterification with oleic acid, so as to which the OPO products for being suitable for the method for the present invention be prepared.
The method of this field routine may be employed in transesterification and reagent (such as catalyst and lipase) carries out.As previously mentioned,
The OPO products being so prepared are hair OPO products.
The method of the present invention before processing is being used, can depickling processing first implemented to hair OPO products.Conventional method progress can be used
Depickling is handled.For example, free fatty can be removed by molecular distillation or can depickling be carried out by alkali refining.For example, it can will wait to locate
The hair OPO of reason is heated to 80 DEG C, and adding in appropriate alkaline liquor according to its acid value is stirred to react a period of time, centrifuging and taking light phase, you can obtain
Obtain the hair OPO products of depickling.
Alternatively, as it was noted above, the OPO products of refining also are adapted for being handled using the method for the present invention.This kind of refining OPO
Product includes but not limited to the refining OPO products that hair OPO products obtain after depickling, decoloration and/or deodorization processing, and also including will
The oil and fat product that refining OPO products obtain after being reconciled with other polished fats, i.e., diluted refining OPO products.
Other polished fats suitable for dilution refining OPO products can be arbitrary edible oil known in the art, especially
It is vegetable oil, includes but not limited to the one or more in sunflower oil, Canola Oil and coconut oil.Preferably, when
When preparing diluted refining OPO products, refining OPO products and other polished fats are reconciled, OPO products are refined in the product
Content accounts for being diluted for diluted other polished fats for more than 40% or addition of diluted refining OPO product gross weights
The content in refining OPO products afterwards is preferably less than 55% less than 60%, and more preferably less than 50%.
It should be understood that it is typically triglyceride mixture to be suitable for the invention OPO products, on a small quantity its may be contained
Its ingredient such as impurity (for example, would generally contain other impurity components in hair OPO products), but does not influence art technology
Personnel are classified as a kind of grease according to usual understanding.
In certain embodiments, OPO products are suitable for the invention (including previously described hair OPO products, refining
OPO products and diluted refining OPO products) in, in terms of the weight of total palmitic acid contained by it, palmitic acid on Sn-2 positions
Content is at least 30%, and such as at least 45%；And 15~55% aliphatic acid is palmitic acid in total fatty acids.
It waits to locate in general, being added to partial glyceride lipase with the amount of the lipase of every gram of 5~500U of pending OPO products
It manages in OPO products.
Herein, " partial glyceride lipase " refers to do not have catalyzing hydrolysis vigor to triglycerides, preferentially to diglyceride
And/or monoglyceride has the lipase of catalyzing hydrolysis vigor.Partial glyceride lipase mainly has two classes：Monoglyceride-glycerine
Diester lipase and monoglyceride lipase.Present invention preferably uses have catalyzing hydrolysis to monoglyceride and/or diglyceride
The partial glyceride lipase of vigor.Partial glyceride lipase well known in the art can be used, aspergillus is derived from for example, can be used
(Aspergillus), the partial glyceride lipase of Penicillium (Penicillium) or Marxist philosophy lesson (Malassezia).
It is further preferred that using from penicillium cammenberti (Penicillium camemberti) or penicillium cyclopium
The partial glyceride lipase of (Penicillium cyclopium).
In certain embodiments, it is suitable for the invention partial glyceride lipase and includes but not limited to such as CN
Partial glyceride lipase disclosed in 201410182887.0, commercially available partial glyceride lipase is as come from Tian Ye companies lipase
G50 (Lipase G " Amano " 50) and lipase GH1 (Huang J, Yang Z, Guan F etc., A novel mono-and
diacylglycerol lipase highly expressed in Pichia pastoris,and its application
For food emulsifier preparation, Process Biochemistry, 2013,48 (12):1899-1904)、
Lipase SMG1 (Xu T, Lu L, Hou S etc., Crystal structure of a mono-and diacylglycerol
lipase from Malassezia globosa,reveals a novel lid conformation and insights
Into the substrate specificity, Journal of Structural Biology, 2012,178 (3):363-
And lipase rePcMdl (Tan Z B, Li J F, Li X T etc., A unique mono-and diacylglycerol 9)
lipase from Penicillium cyclopium:heterologous expression,biochemical
Characterization and molecular basis for its substrate selectivity, Plos One,
2014,9 (7):E102040) etc..
Without wishing to be bound by any theory, selected various partial glyceride lipases have the same or similar in the present invention
Reaction principle, thus using the method in invention to OPO product treatments after, technique effect as reaching identical or thinking.
In certain embodiments, the dosage of partial glyceride lipase for every gram of 5~50U of pending OPO products, 50~
250U, 250~500U, 10~450U or 50~450U.
In general, the additive amount of water be pending OPO product weights more than 0.1%, such as 0.1~30%, 0.1~20,
0.1~15%, 1~20%, 1~10% or 10~20% etc..
Partial glyceride lipase can be added successively with water, can also be added simultaneously.Alternatively, can first with partial glyceride lipase with
It is then added to after water mixing in grease.
" processing " of the present invention includes but not limited to the OPO productions that partial glyceride lipase and water are with the addition of described in stirring
Product.In general, at 10~50 DEG C, such as stirred at a temperature of 20~50 DEG C, 20~30 DEG C, 20~40 DEG C or 30~40 DEG C.Stirring
Time when can be 1~30 small, such as 1~6 it is small when, 1~24 it is small when, 2~6 it is small when, 6~24 it is small when or 2~24 it is small when.
For hair OPO products, using the method for the present invention before processing, depickling processing can be first carried out as mentioned before.It is alternatively, right
In the hair OPO products of not advance depickling, after being handled through the method for the present invention, any one of depickling, decoloration and deodorization can be carried out
Or a variety of processing.The method that this field routine can be used in decoloration and deodorization carries out.For example, for decoloration, it can be by grease in vacuum
Under be heated to 100~110 DEG C, add in the decolorising agent (such as atlapulgite) of appropriate (such as grease weight 1~2%), vacuum kept to stir
A period of time is mixed, then filtering can obtain bleached oil fat.For deodorization, it is passed through nitrogen and serves as stirring and deodorization medium, very
Reciprocal of duty cycle is about 10-20mBar, and a period of time is kept at 230~250 DEG C.For refining OPO products, it can add in the present invention's
Partial glyceride lipase and water are handled as described herein, then can be carried out according to actual conditions in alkali refining, decoloration and deodorization
One or more.
The present invention is there is thus also provided a kind of OPO products, and two palmitic acid relative amounts are more than 30% in the OPO products, such as
More than 50%, preferably greater than 54%, be greater than 55%, more than 56%, more than 60%.It is furthermore preferred that the OPO products of the present invention
In 1,3-Dioleic acid-2-palmitoyl triglyceride content in terms of C52 be more than 36%, preferably greater than 40%, be greater than
41%th, more than 42%, more than 43% etc..
In certain embodiments, OPO products of the invention with its without the method for the present invention processing reference product compared with,
Two palmitic acid relative amounts have at least 5% raising, for example, at least 6%, at least 7%, at least 8%, at least 9% raising.
In certain embodiments, OPO products of the invention are compared with its reference product not processed by the invention, and 1 in terms of C52,
Bis- oleic acid -2- palmitic acids of 3-, three ester content has at least 3%, for example, at least 3.5%, at least 4%, and at least 5% or at least 6%
Raising.
In certain embodiments, the OPO products are prepared using the method for the present invention.
Hereafter the present invention will be illustrated in a manner of specific embodiment.It is to be understood that these embodiments are only illustrative, and
It is not intended to limit the scope of the invention.Method and reagent employed in embodiment, unless otherwise stated, being ability
The method and reagent of domain routine.
Grease used derives from Southseas Specialty Fats Industrial (Shanghai) Co., Ltd., sodium methoxide source in following embodiments
Sigma-Aldrich, immobilized lipase Lipozyme RM IM derive from Novozymes Company, and lipase G50 is wild from day
Company.What is used in the embodiment of the present invention refers to object detection method with reference to national standard GB30604-2015 on OPO.
Embodiment 1
800g palm oil stearins (IV16) and 200g high oleic sunflower oils are mixed, are heated to 105 DEG C, under vacuo
Stirring 30min is dehydrated.1g sodium methoxides are added in, reaction 30min is stirred under vacuum at 105 DEG C, adds in 20g aqueous citric acid solutions
(15% weight ratio), stirring 20min terminate reaction.Reactant is washed repeatedly with hot water, takes off soap.105 DEG C are heated to, very
Sky stirring 30min is dehydrated, and obtains transesterification grease.The above-mentioned transesterification greases of 500g and 1000g oleic acid is taken to mix, is pressed
Pass through the enzyme column of filling 100g Lipozyme RM IM according to the flow velocity of 200g/h, reaction temperature is controlled at 60 DEG C.It collects by enzyme column
The hair OPO-1 of outflow.
Take 500g maos of OPO-1, lipase G50 added according to every gram of grease of 250U enzyme activity, add in account for oily weight 10% go from
Sub- water when 30 DEG C of stirrings 2 are small, is centrifuged off water.Free fatty is removed by molecular distillation, by the grease after depickling true
105 DEG C are heated under sky, adds in the atlapulgite of grease weight 1.5%, keeps being stirred under vacuum 30 minutes, decoloration is obtained by filtration
Grease.Nitrogen (serving as stirring and deodorization medium) is passed through to the grease after decoloration, vacuum degree is about 10-20mBar, 240
It is deodorized to obtain refining OPO-1 when holding 1 is small at DEG C, be measured secondly position palmitic acid accounts for bis- oil of all palmitic acid contents and 1,3-
Three ester content (in terms of C52) of acid -2- palmitic acids, the results are shown in Table 1.
Comparative example 1
The hair OPO-1 that 500g embodiments 1 are prepared is taken, free fatty is removed by molecular distillation, according to embodiment 1
The method is decolourized to the grease after depickling, is deodorized, and obtains refining OPO-2, measures secondly position palmitic acid accounts for all palm fibres
Palmitic acid acid content and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 1.
Embodiment 2
The hair OPO-1 that 1000g embodiments 1 are prepared is taken, free fatty is removed by molecular distillation.Take 200g depicklings
Oil afterwards adds in lipase G50 according to every gram of grease of 5U enzyme activity, adds in the deionized water for accounting for oily weight 1%, small in 20 DEG C of stirrings 24
When.80 DEG C will be heated to by the grease of washing, adding in appropriate alkaline liquor according to the acid value of grease is stirred to react 30 minutes, centrifuging and taking
Light phase.Above-mentioned grease is heated to 105 DEG C under vacuo, adds in the atlapulgite of grease weight 1.5%, keeps being stirred under vacuum
30 minutes, the grease of decoloration is obtained by filtration.Nitrogen (serving as stirring and deodorization medium), vacuum degree are passed through to the grease after decoloration
About 10-20mBar is deodorized to obtain alkali refining OPO-1 when holding 1 is small at 240 DEG C, be measured secondly position palmitic acid accounts for institute
There are palmitic acid content and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 1.
Comparative example 2
The hair OPO-1 that 1000g embodiments 1 are prepared is taken, free fatty is removed by molecular distillation.Take 200g depicklings
Grease afterwards carries out alkali refining according to the method described in embodiment 2, and decoloration, deodorization obtain alkali refining OPO-2, measure secondly position palmitic acid
All palmitic acid contents and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52) are accounted for, the results are shown in Table 1.
Table 1
Above-described embodiment it can be found that traditional refining or alkali-refining process to 2 palmitic acid relative amounts of OPO and
Bis- oleic acid -2- palmitic acids of 1,3-, three ester content (in terms of C52) does not influence substantially.By the present invention method to OPO into
Row post-processing, 2 palmitic acid relative amounts and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52) promote effect
Fruit is notable.
Embodiment 3
1000g palm oil stearins (IV16) are heated to 105 DEG C, 30min is stirred under vacuo and is dehydrated.Add in 1g
Sodium methoxide is stirred under vacuum reaction 30min at 105 DEG C, adds in 20g aqueous citric acid solutions (15% weight ratio), and stirring 20min is terminated
Reaction.Reactant is washed repeatedly with hot water, takes off soap.105 DEG C are heated to, 30min is stirred under vacuum and is dehydrated, obtained
To transesterification grease.The above-mentioned transesterification greases of 500g and 1000g oleic acid is taken to mix, according to the flow velocity of 200g/h by filling 100g
The enzyme column of Lipozyme RM IM, reaction temperature are controlled at 60 DEG C.Collect the hair OPO-3 flowed out by enzyme column.
Take 500g maos of OPO-3, lipase G50 added according to every gram of grease of 500U enzyme activity, add in account for oily weight 20% go from
Sub- water when 40 DEG C of stirrings 1 are small, is centrifuged off water.Free fatty is removed by molecular distillation, by the grease after depickling true
105 DEG C are heated under sky, adds in the atlapulgite of grease weight 1.5%, keeps being stirred under vacuum 30 minutes, decoloration is obtained by filtration
Grease.Nitrogen (serving as stirring and deodorization medium) is passed through to the grease after decoloration, vacuum degree is about 10-20mBar, 240
It is deodorized to obtain refining OPO-3 when holding 1 is small at DEG C, be measured secondly position palmitic acid accounts for bis- oil of all palmitic acid contents and 1,3-
Three ester content (in terms of C52) of acid -2- palmitic acids, the results are shown in Table 2.
Comparative example 3
The hair OPO-3 that 500g embodiments 3 are prepared is taken, free fatty is removed by molecular distillation, after depickling
Grease is decolourized according to the method described in embodiment 3, is deodorized, and is obtained refining OPO-4, is measured secondly position palmitic acid accounts for all palm fibres
Palmitic acid acid content and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 2.
Embodiment 4
1000g palm oils are heated to 105 DEG C, 30min is stirred under vacuo and is dehydrated.1g sodium methoxides are added in, 105
DEG C be stirred under vacuum reaction 30min, add in 20g aqueous citric acid solutions (15% weight ratio), stirring 20min terminate reaction.Use hot water
Reactant is washed repeatedly, takes off soap.105 DEG C are heated to, 30min is stirred under vacuum and is dehydrated, obtain ester-exchanged oil
Fat.The above-mentioned transesterification greases of 500g and 500g oleic acid is taken to mix, according to the flow velocity of 200g/h by filling 100g Lipozyme
The enzyme column of RM IM, reaction temperature are controlled at 60 DEG C.Collect the hair OPO-4 flowed out by enzyme column.
500g maos of OPO-4 are taken, lipase G50 is added according to every gram of grease of 50U enzyme activity, adds in the deionization for accounting for oily weight 10%
Water when 30 DEG C of stirrings 6 are small, is centrifuged off water.Free fatty is removed by molecular distillation, by the grease after depickling in vacuum
Under be heated to 105 DEG C, add in the atlapulgite of grease weight 1.5%, keep being stirred under vacuum 30 minutes, the oil of decoloration is obtained by filtration
Fat.Nitrogen (serving as stirring and deodorization medium) is passed through to the grease after decoloration, vacuum degree is about 10-20mBar, at 240 DEG C
It is lower keep 1 it is small when be deodorized to obtain refining OPO-5, measure secondly position palmitic acid accounts for bis- oil of all palmitic acid contents and 1,3-
Three ester content (in terms of C52) of acid -2- palmitic acids, the results are shown in Table 2.
Comparative example 4
The hair OPO-4 that 500g embodiments 4 are prepared is taken, free fatty is removed by molecular distillation, after depickling
Grease is decolourized according to the method described in embodiment 4, is deodorized to obtain refining OPO-6, is measured secondly position palmitic acid accounts for all palm fibres
Palmitic acid acid content and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 2.
Table 2
The above embodiments show the OPO products prepared for different material, and the present invention can still be handled by post-processing
Improve three ester content of 2 palmitic acid relative amounts and bis- oleic acid -2- palmitic acids of 1,3- of product (in terms of C52).
Embodiment 5
The hair OPO-3 that 1000g embodiments 3 are prepared is taken, free fatty is removed by molecular distillation.Take 300g depicklings
Grease afterwards and the mixing of 300g oleic acid, according to the flow velocity of 200g/h by the enzyme column of filling 100g Lipozyme RM IM, reaction
Temperature is controlled at 60 DEG C.Collect the hair OPO-5 flowed out by enzyme column.Free fatty is removed by molecular distillation.Take 200g depicklings
Oil afterwards adds in lipase G50 according to every gram of grease of 50U enzyme activity, adds in the deionized water for accounting for oily weight 10%, 6 are stirred at 40 DEG C
Hour.
80 DEG C will be heated to by the grease of washing, adding in appropriate alkaline liquor according to the acid value of grease is stirred to react 30 minutes,
Centrifuging and taking light phase.Above-mentioned grease is heated to 105 DEG C under vacuo, adds in the atlapulgite of grease weight 1.5%, keeps true
The grease of decoloration is obtained by filtration in sky stirring 30 minutes.Nitrogen (serving as stirring and deodorization medium) is passed through to the grease after decoloration,
Vacuum degree is about 10-20mBar, is deodorized to obtain alkali refining OPO-5 when holding 1 is small at 240 DEG C, be measured secondly position palm
Acid accounts for all palmitic acid contents and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 3.
Comparative example 5
The hair OPO-5 that 500g embodiments 5 are prepared is taken, free fatty is removed by molecular distillation.Take 200g depicklings
Oil afterwards carries out alkali refining, decoloration and deodorization according to the method described in embodiment 5, obtains alkali refining OPO-6, measures secondly position palm
Acid accounts for all palmitic acid contents and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 3.
Comparative example 6
The hair OPO-5 that 500g embodiments 5 are prepared is taken, free fatty is removed by molecular distillation.Take 200g depicklings
Oil afterwards adds in lipase G50 according to every gram of grease of 50U enzyme activity, does not add additional water, when 40 DEG C of stirrings 6 are small.According to reality
It applies the method described in example 5 and carries out alkali refining, decoloration and deodorization, obtain alkali refining OPO-7, measure secondly position palmitic acid accounts for all palmitic acids
Content and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 3.
Comparative example 7
The hair OPO-5 that 500g embodiments 5 are prepared is taken, free fatty is removed by molecular distillation.Take 200g depicklings
Oil afterwards according to the deionized water of the weight of grease addition 10%, does not add lipase, when 40 DEG C of stirrings 6 are small.According to implementation
Method described in example 5 carries out alkali refining, decoloration and deodorization, obtains alkali refining OPO-8, measures secondly position palmitic acid accounts for all palmitic acids contains
Amount and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), the results are shown in Table 3.
Table 3
It is above-mentioned the result shows that OPO greases individually and lipase contact or individually contact with water and cannot all play raising two
Position palmitic acid accounts for the effect of all palmitic acid contents and 1,3-Dioleic acid-2-palmitoyl triglyceride content (in terms of C52), only
OPO greases and the water containing lipase are subjected to contact competence exertion effect.
Comparative example 8
The alkali refining OPO-6 and sunflower oil that comparative example 5 is prepared, Canola Oil and coconut oil are taken according to 5:2:2:
1 is mixed to get dilution type OPO-1.It measures secondly position palmitic acid accounts for all palmitic acid contents and bis- oleic acid -2- palmitic acids of 1,3- are sweet
Oily three ester contents (in terms of C52), the results are shown in Table 4.
Embodiment 6
The dilution type OPO-1 that 200g comparative examples 8 are prepared is taken, lipase G50 is added according to every gram of grease of 50U enzyme activity,
0.1% deionized water is added in, when 30 DEG C of stirrings 24 are small.Alkali refining, decoloration are carried out according to the method described in embodiment 5 and are taken off
It is smelly, obtain dilution type OPO-2.It measures secondly position palmitic acid accounts for bis- oleic acid -2- palmitic acids of all palmitic acid contents and 1,3-
Three ester contents (in terms of C52), the results are shown in Table 4.
Table 4
Table 4 the result shows that, for the compound lard of OPO and other refining vegetable oils, the method for the present invention still can be effective
It improves two palmitic acids and accounts for three ester content of all palmitic acid contents and bis- oleic acid -2- palmitic acids of 1,3- (in terms of C52).
Claims (10)
1. a kind of, to improve two palmitic acid relative amounts and/or bis- oleic acid -2- palmitic acids of 1,3- in terms of C52 in OPO products sweet
The method of oily three ester contents, which is characterized in that the described method includes the OPO products described in partial glyceride lipase and water process
Step.
2. the method as described in claim 1, which is characterized in that the partial glyceride lipase is derived from aspergillus
(Aspergillus), the lipase of Penicillium (Penicillium) or Marxist philosophy lesson (Malassezia)；
Preferably, the partial glyceride lipase is derived from penicillium cammenberti (Penicillium camemberti) or circle
The lipase of arc Penicillium notatum (Penicillium cyclopium)；
It is highly preferred that the partial glyceride lipase is lipase G50.
3. method as claimed in claim 1 or 2, which is characterized in that the additive amount of the partial glyceride lipase is treated for every gram
Handle the enzyme of 5~500U of OPO products, such as 5~50U, 50~250U, 250~500U, 10~450U or 50~450U.
4. such as the method any one of claim 1-3, which is characterized in that the additive amount of the water produces for pending OPO
More than the 0.1% of product weight, such as 0.1~30%, 0.1~20,0.1~15%, 1~20%, 1~10% or 10~20%.
5. such as the method any one of claim 1-4, which is characterized in that the processing is the temperature at 10~50 DEG C
Lower stirring is preferably 20~50 DEG C, more preferably 30~40 DEG C；
Preferably, when the time of stirring is 1~30 small.
6. such as the method any one of claim 1-5, which is characterized in that the OPO products are hair OPO products or essence
Refine OPO products；
Preferably, the OPO products are triglyceride mixture, and aliphatic acid is the triglycerides of palmitic acid wherein on Sn-2 positions
Content is more than 30%, and the aliphatic acid of 15~55wt% is palmitic acid in total fatty acids.
7. method as claimed in claim 6, which is characterized in that the OPO products are hair OPO products, and the processing is in hair OPO
It carries out before product depickling or is carried out after hair OPO product depicklings.
8. such as the method any one of claim 1-7, which is characterized in that further include depickling, decoloration after the processing
With deodorization one or more of step.
9. a kind of OPO product preparation methods, which is characterized in that the described method includes using any one of claim 1-8
Method it is sweet to improve two palmitic acid relative amounts in the OPO products and/or the bis- oleic acid -2- palmitic acids of 1,3- in terms of C52
The step of oily three ester content.
10. a kind of OPO products, in the OPO products, with total restatement of all palmitic acids, the content of two palmitic acids is more than 30%,
And the aliphatic acid of 15~55wt% is palmitic acid in total fatty acids, it is preferred that 1,3-, the bis- oleic acid -2- palmitic acids in terms of C52 are sweet
Oily three ester contents are more than 36%, more preferably more than 40%；
Preferably, the OPO products are prepared using the method any one of claim 1-9.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111961527A (en) * | 2020-09-03 | 2020-11-20 | 广州白云山汉方现代药业有限公司 | Accurate control method for palmitic acid content in olive oil |
| CN112195199A (en) * | 2020-10-29 | 2021-01-08 | 赞宇科技集团股份有限公司 | Production method of 1, 3-dioleoyl-2-palmitic acid triglyceride |
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| CN112195199A (en) * | 2020-10-29 | 2021-01-08 | 赞宇科技集团股份有限公司 | Production method of 1, 3-dioleoyl-2-palmitic acid triglyceride |
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