CN104087626A - Method for preparing composition containing 2-palmitin - Google Patents

Method for preparing composition containing 2-palmitin Download PDF

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Publication number
CN104087626A
CN104087626A CN201410319597.6A CN201410319597A CN104087626A CN 104087626 A CN104087626 A CN 104087626A CN 201410319597 A CN201410319597 A CN 201410319597A CN 104087626 A CN104087626 A CN 104087626A
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palmitin
composition
preparation
acid
palmitic acid
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汪志明
李翔宇
陆姝欢
周强
汪锋
肖敏
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Chia Lung Biological Engineering (wuhan) Co Ltd
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Chia Lung Biological Engineering (wuhan) Co Ltd
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Priority to CN201410319597.6A priority Critical patent/CN104087626A/en
Priority to CN201611006726.1A priority patent/CN106591386A/en
Publication of CN104087626A publication Critical patent/CN104087626A/en
Priority to PCT/CN2015/082488 priority patent/WO2016004825A1/en
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/64Fats; 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
    • C12P7/6436Fatty acid esters
    • C12P7/6445Glycerides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10Ester interchange

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  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
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  • Fats And Perfumes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention relates to a method for preparing a composition containing 2-palmitin. The method comprises the steps of providing a glyceride containing a palmitate residue; mixing the glyceride containing the palmitate residue with palmitic acid, palmitate or palmitic acid non-glyceride, and performing ester exchange to obtain grease A; performing enzymatic directional ester exchange on the grease A and unsaturated fatty acid or non-glyceride of the unsaturated fatty acid to obtain mixed oil B; refining the mixed oil B to obtain the composition containing 2-palmitin. The preparation process is simple. Compared with the existing method, the method disclosed by the invention has the advantages that the content of palmitic acid at the second site in the product prepared by using the method is higher, and fewer byproducts are produced after preparation, so that the method is favorable for environment friendliness.

Description

The preparation method of the composition that contains 2-palmitin
Technical field
The present invention relates to a kind of preparation method of composition of the 2-of containing palmitin.
Background technology
Triglyceride level is the main composition that the mankind absorb.Modern nutriology is verified, human body in the process of devil's brew three esters, can selective hydrolysis Sn-1, the lipid acid on 3, forms 2-mono-glycerides and a large amount of free fatty acids.These free fatty acidies there will be two kinds of reactions in vivo: 1, absorbed by self; 2, with after interior other substance reactions of body be discharged from.Research shows, compared with free unsaturated fatty acid, free saturated fatty acid uptake rate is slow, more easily and calcium react, form insoluble soap calcium, and then be excreted.As can be seen here, with respect to the triglyceride level that produces free saturated fatty acid, the triglyceride level that produces free unsaturated fatty acid is more conducive to the absorption of human body.Commercially available edible oil is mainly derived from plant at present, and its saturated fatty acid is mainly distributed in sn-1,3, human body in digestive process, not only run off a large amount of fat and calcium, and the soap calcium of its generation can increase the hardness of ight soil, cause part population constipation and stomachache, even cause intestinal obstruction.If saturated fatty acid is concentrated on to the sn-2 position (also referred to as " 2 ") of triglyceride level, can effectively address this problem, especially in poor health, the individuality that functions of intestines and stomach is bad, effect is more obvious.
In breast milk, the fat of 98% left and right exists with the form of triglyceride level, wherein palmitinic acid (Palmitic acid, C16:0, saturated fatty acid) content account for 20-25%, oleic acid (oleic acid, C18:1, unsaturated fatty acids) content accounts for 30-38%.Further, most palmitinic acid is distributed in 2 of triglyceride level, and oleic acid is mainly distributed on Sn-1 and Sn-3 position, and in breast milk, the triglyceride structure of this uniqueness is called as 2-palmitin.At present, baby formula milk powder on market and the component content of breast milk are more approaching, and still, a large amount of human trial and experimentation on animalies all confirm, the absorption of human milk fat is better than baby formula milk powder, and one of them major reason is just triglyceride structure unique in breast milk.
Be subject to the inspiration of triglyceride structure unique in breast milk, there is at present part manufacturer to utilize the modification of natural fats and oils has been produced to the composition that contains 2-palmitin, and added in baby milk powder and special diet, this not only can improve the assimilated efficiency of human body to fat and calcium, the hardness of ight soil be can also reduce, constipation and ileac probability of occurrence reduced.
China granted patent CN102229866B discloses one and has utilized lard for raw material, adopts the lipase-catalyzed acidolysis process of 1,3 regioselectivity, prepares low-cholesterol, the processing method of high 2-palmitin composition.But lard component complexity, therefore complicated process of preparation, and in practical application, also may be subject to the restriction of religion or national belief.
It is the method that the palm oil stearin of 8-12 and the ester of oleic acid or its nonglyceride carry out enzymatic transesterification acquisition 2-palmitin by making iodine number (IV) that China granted patent CN101258230B discloses a kind of.CN101679909B also discloses a kind of method of the 2-of acquisition palmitin composition, the method is mainly by one or more being comprised to three palmitoyl glycerides, iodine number is that approximately 18 to approximately 40 palm oil stearin fractions is carried out after random transesterify, with oleic acid or its nonglyceride 1, under the effect of 3 specificity enzymes, carry out after enzymatic interesterification procedure, after separation palmitinic acid or palmitic non-glyceride esters, make target product.But these methods are subject to the restriction of raw material, the purity of product is all lower.Even if improved the content of 2 upper palmitinic acids by random transesterify, the total but restriction that forms due to palmitinic acid, the purity of product is not still high.Such composition carry out follow-up refining in, can produce a large amount of wastes, as sodium soap etc., be unfavorable for environmental protection.
Therefore, still need to provide a kind of preparation method of the new composition that contains 2-palmitin.
art methods
(1) provide a kind of shortening, it is that 23.0%, 2 palmitic acid content is 16.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate shortening 400g, lipase 20g and deionized water 1g are placed in to container, stir and be warming up to 60 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, obtain fat A.
(3) fat A 300g is mixed with arachidonic acid 600g, be placed in container, stir and be warming up to 60 DEG C and keep constant, add 700ml octane, add sn-1,3 specific lipase 37g, maintain reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by dry method fractionation again, obtain the composition that contains 2-palmitin after deodorization, detecting 2 palmitic acid contents by GC and thin-layer chromatography is 20.1wt%.
Can find out by contrast, the present invention has added after ethyl palmitate in step 2, and in end product, 2 palmitic acid contents are greatly improved.
art methods
(1) provide a kind of palm oil stearin, it is that 43.7%, 2 palmitic acid content is 31.8% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 3000g, lipase 100g and deionized water 12.5g are placed in to flask, add nitrogen protection, it is constant that stirring is warming up to 160 DEG C of maintenances, sustained reaction 30 hours.After reaction finishes, obtain fat A.
(3) fat A 2500g is mixed with docosahexenoic acid 5000g, be placed in container, stir and be warming up to 65 DEG C and keep constant, add 7000ml hexane, add sn-1,3 specific lipase 375g, condensing reflux pipe is installed, is maintained reaction 5 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 38.4wt%.
Can find out by contrast, the present invention has added after potassium palmitate in step 2, and in end product, 2 palmitic acid contents are improved.
art methods
(1) provide a kind of palm oil stearin, it is that 64%, 2 palmitic acid content is 45.5% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 333.3g, lipase 10g and deionized water 1.25g are placed in to container, stir and be warming up to 220 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, obtain fat A.
(3) fat A 250g is mixed with arachidonic acid 500g, be placed in container, stir and be warming up to 60 DEG C and keep constant, add 700ml hexane, add sn-1,3 specific lipase 37.5g, condensing reflux pipe is installed, is maintained reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 56.5wt%.
Can find out by contrast, the present invention has added after potassium palmitate in step 2, and in end product, 2 palmitic acid contents are improved.
Summary of the invention
The object of this invention is to provide a kind of preparation method of the new composition that contains 2-palmitin.
For achieving the above object, the technical solution used in the present invention is as follows:
A preparation method for the composition that contains 2-palmitin, comprises the steps:
(1) provide the glyceryl ester that contains palmitic acid residues;
(2) glyceryl ester that contains palmitic acid residues is mixed and carries out transesterify with palmitinic acid, palmitate or palmitic non-glyceride esters, obtain fat A;
(3) fat A and unsaturated fatty acids or its nonglyceride are carried out to Sn-1,3 enzymatic directed inter-esterification, obtain mixing oil B;
(4) mixing oil B is refining, obtain the composition that contains 2-palmitin.
Press such scheme, described palmitate comprises Sodium pentadecanecarboxylate or potassium palmitate, and palmitate is not more than 4:1 with the weight ratio of the glyceryl ester that contains palmitic acid residues, is preferably 1:500-4:1, is more preferably 1:50-1:1.
Press such scheme, described palmitic non-glyceride esters comprises Uniphat A60 or ethyl palmitate, and palmitic non-glyceride esters is not more than 4:1 with the weight ratio of the glyceryl ester that contains palmitic acid residues, is preferably 1:500-4:1, is more preferably 1:50-1:1.
Press such scheme, described palmitinic acid is not more than 4:1 with the weight ratio of the glyceryl ester that contains palmitic acid residues, is preferably 1:500-4:1, is more preferably 1:50-1:1.
Press such scheme, in the transesterify system of described step (2), further add water, water is less than 5wt% with the proportion of the glyceryl ester that contains palmitic acid residues, is preferably less than 2wt%, is more preferably less than 1wt%.
Press such scheme, in the transesterify system of described step (2), while selecting palmitic non-glyceride esters to be reactant, can add lipase, lipase is 1wt%-50wt% with the proportion of the glyceryl ester that contains palmitic acid residues.
Press such scheme, after the transesterify of described step (2) finishes, through making fat A.
Press such scheme, in described step (3), the weight ratio of fat A and unsaturated fatty acids or its nonglyceride is 2:1-1:10, is preferably 1:1-1:3.
Press such scheme, in the enzymatic directed inter-esterification system of described step (3), further add solvent, described solvent comprises hexane, hexanaphthene, octane or octane-iso.
Press such scheme, the unsaturated fatty acids in described step (3) comprises oleic acid, linolic acid, linolenic acid, arachidonic acid, timnodonic acid and docosahexenoic acid.
The present invention proposes a kind of new preparation method who contains 2-palmitin composition, its preparation technology is simple.Compared with the conventional method, use in the product that method of the present invention makes, 2 palmitic acid contents are higher, and by product after preparation is less, is therefore conducive to environmental protection.
Embodiment
Below in conjunction with specific examples, the present invention is described in further detail.
Embodiment 1
(1) provide a kind of plam oil, it is that 21.7%, 2 palmitic acid content is 15.6% that its palmitinic acid accounts for total fatty acids ratio.Wherein, " 2 palmitic acid contents " refers to that 2 upper palmitinic acids account for the content of 2 upper all lipid acid, and its detection method is with reference to GB/T24894, lower same.
(2) reaction substrate plam oil 25g, palmitinic acid 1g and potassium hydroxide 0.5g are placed in to flask, stirring is warming up to 170 DEG C and keep constant, after sustained reaction 10 hours (transesterify, lower with), add hexane 50ml and fully dissolve the rear centrifugal lipid acid potassium of removing, obtain fat A.
(3) fat A 20g is mixed with oleic acid 20g, be placed in four-hole boiling flask, stir and be warming up to 68 DEG C and keep constant, add sn-1,3 specific lipase 2.4g, back flow reaction 8 hours (directed inter-esterification, lower with), obtains mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, free fatty acids is removed in dry method fractionation, after deodorization, obtain the composition that contains 2-palmitin, by GC (high temperature capillary column, fid detector, lower with) and thin-layer chromatography detect 2 palmitic acid contents be 20.1wt%.
Embodiment 2
(1) provide a kind of plam oil, it is that 22.8%, 2 palmitic acid content is 16.4% that its palmitinic acid accounts for total fatty acids ratio.
(2) plam oil 50g, Uniphat A60 1g and lipase 0.5g are added in flask, stir and be warming up to 76 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, remove fatty acid methyl ester by dry method fractionation, obtain fat A.
(3) fat A 40g is mixed with linolic acid 20g, be placed in four-hole boiling flask, stir and be warming up to 70 DEG C and keep constant, add 200ml hexanaphthene, add sn-1,3 specific lipase 2.4g, back flow reaction 7 hours, obtains mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, free fatty acids is removed in dry method fractionation, obtains containing 2-palmitin composition after deodorization, and detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 21.0wt%.
Embodiment 3
Under equal conditions, respectively by preparation method of the present invention and existing preparation method's preparing product, and compare.
the inventive method
(1) provide a kind of shortening, it is that 23.0%, 2 palmitic acid content is 16.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate shortening 200g, ethyl palmitate 200g, lipase 20g and deionized water 1g are placed in to container, stir and be warming up to 60 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, remove fatty-acid ethyl ester by molecular distillation, obtain fat A.
(3) fat A 300g is mixed with arachidonic acid 600g, be placed in container, stir and be warming up to 60 DEG C and keep constant, add 700ml octane, add sn-1,3 specific lipase 37g, maintain reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by dry method fractionation again, obtain the composition that contains 2-palmitin after deodorization, detecting 2 palmitic acid contents by GC and thin-layer chromatography is 49wt%.
Embodiment 4
(1) provide a kind of shortening, it is that 23%, 2 palmitic acid content is 16.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate shortening 2000g, ethyl palmitate 500g and lipase 1000g are placed in to container, under nitrogen protection, are heated to 50 DEG C and keep constant, sustained reaction 5 hours.After reaction finishes, remove fatty-acid ethyl ester by molecular distillation, obtain fat A.
(3) fat A 2000g is mixed and is placed in container with arachidonic acid 20000g, stir and be warming up to 75 DEG C and keep constant, add 7L hexane, add sn-1,3 specific lipase 500g, install condensing reflux pipe, and sustained reaction 6 hours, obtains mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 26.6%.
Embodiment 5
(1) provide a kind of shortening, it is that 42.4%, 2 palmitic acid content is 31.5% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 240g, Sodium pentadecanecarboxylate 24g and deionized water 12g are placed in to flask, under nitrogen protection, are heated to 190 DEG C and keep constant, sustained reaction 10 hours.After reaction finishes, add acetone 600ml and fully dissolve the rear centrifugal sodium soap of removing, obtain fat A.
(3) fat A 200g is mixed with timnodonic acid 600g, be placed in four-hole boiling flask, stir and be warming up to 45 DEG C and keep constant, add 700mL octane-iso, add sn-1,3 specific lipase 40g, condensing reflux pipe is installed, is maintained reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 40.2wt%.
Embodiment 6
Under equal conditions, respectively by preparation method of the present invention and existing preparation method's preparing product, and compare.
the inventive method
(1) provide a kind of palm oil stearin, it is that 43.7%, 2 palmitic acid content is 31.8% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 2500g, potassium palmitate 500g and deionized water 12.5g are placed in to flask, add nitrogen protection, it is constant that stirring is warming up to 160 DEG C of maintenances, sustained reaction 30 hours.After reaction finishes, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 2500g is mixed with docosahexenoic acid 5000g, be placed in container, stir and be warming up to 65 DEG C and keep constant, add 700ml hexane, add sn-1,3 specific lipase 375g, condensing reflux pipe is installed, is maintained reaction 5 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 45.4wt%.
Embodiment 7
(1) provide a kind of palm oil stearin, it is that 61.9%, 2 palmitic acid content is 43.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 200g, Sodium pentadecanecarboxylate 50g and deionized water 1.25g are placed in to flask, stir and be warming up to 190 DEG C and keep constant, sustained reaction 10 hours.After reaction finishes, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 200g is mixed with oleic acid 700g, be placed in four-hole boiling flask, stir and be warming up to 50 DEG C and keep constant, add 70ml hexane, add sn-1,3 specific lipase 50g, install condensing reflux pipe, maintain reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 63.3wt%.
Embodiment 8
(1) provide a kind of palm oil stearin, it is that 61.9%, 2 palmitic acid content is 43.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 2500g, Sodium pentadecanecarboxylate 500g and deionized water 12.5g are placed in to container, stir and be warming up to 190 DEG C and keep constant, sustained reaction 10 hours.After reaction finishes, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 2500g is mixed with oleic acid 7500g, be placed in container, stir and be warming up to 50 DEG C and keep constant, add 7000ml hexane, add sn-1,3 specific lipase 500g, install condensing reflux pipe, maintain reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 62.0wt%.
Embodiment 9
Under equal conditions, respectively by preparation method of the present invention and existing preparation method's preparing product, and compare.
the inventive method
(1) provide a kind of palm oil stearin, it is that 64%, 2 palmitic acid content is 45.5% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 250g, potassium palmitate 83.3g and deionized water 1.25g are placed in to container, stir and be warming up to 220 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 250g is mixed with arachidonic acid 500g, be placed in container, stir and be warming up to 60 DEG C and keep constant, add 700ml hexane, add sn-1,3 specific lipase 37.5g, condensing reflux pipe is installed, is maintained reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 68.2wt%.
Embodiment 10
(1) provide a kind of palm oil stearin, it is that 62.3%, 2 palmitic acid content is 44.4% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 250g, potassium palmitate 15g and deionized water 1.25g are placed in to container, stir and be warming up to 160 DEG C and keep constant, sustained reaction 10 hours.After reaction finishes, add hexane 600mL and fully dissolve, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 200g is mixed with oleic acid 1200g, be placed in container, stir and be warming up to 70 DEG C and keep constant, add sn-1,3 specific lipase 70g, install condensing reflux pipe, maintain reaction 6 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 58.1wt%.
Embodiment 11
(1) provide a kind of palm oil stearin, it is that 64%, 2 palmitic acid content is 45.5% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 5000g, potassium palmitate 150g and deionized water 12g are placed in to container, stir and be warming up to 220 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, add acetone 16L and fully dissolve, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 3000g is mixed with linolenic acid 6000g, be placed in container, stir and be warming up to 60 DEG C and keep constant, add 7000ml hexane, add sn-1,3 specific lipase 400g, install condensing reflux pipe, maintain reaction 4 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 59.2wt%.
Embodiment 12
(1) provide a kind of palm oil stearin, it is that 71.5%, 2 palmitic acid content is 55.6% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate palm oil stearin 10000g, Sodium pentadecanecarboxylate 20g and deionized water 12g are placed in to container, stir and be warming up to 160 DEG C and keep constant, sustained reaction 10 hours.After reaction finishes, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 5000g is mixed with ethyl linoleate 30000g, be placed in container, stir and be warming up to 68 DEG C and keep constant, add 7000ml hexane, add sn-1,3 specific lipase 4000g, condensing reflux pipe is installed, is maintained reaction 9 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove fatty-acid ethyl ester by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 63.1wt%.
Embodiment 13
(1) provide a kind of shortening, it is 16.5% that its palmitinic acid accounts for total fatty acids ratio,, 2 palmitic acid contents are 13.3%.
(2) reaction substrate shortening 250g, Sodium pentadecanecarboxylate 50g and deionized water 1.25g are placed in to flask, add helium protection, stir and be warming up to 150 DEG C and keep constant, sustained reaction 20 hours.After reaction finishes, add acetone 700ml, after fully dissolving, soap (content of soap is less than 10ppm) is removed in centrifuging, obtains fat A.
(3) fat A 250g is mixed with oleic acid 500g, be placed in four-hole boiling flask, stir and be warming up to 72 DEG C and keep constant, add 700ml hexane, add sn-1,3 specific lipase 37.5g, condensing reflux pipe is installed, is maintained reaction 12 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain containing 2-palmitin composition after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 21.1wt%.
Embodiment 14
(1) provide a kind of shortening, it is that 23.0%, 2 palmitic acid content is 16.9% that its palmitinic acid accounts for total fatty acids ratio
(2) reaction substrate shortening 200g, ethyl palmitate 400g, lipase 10g and deionized water 1g are placed in to flask, add helium protection, stir and be warming up to 60 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, molecular distillation method is removed fatty-acid ethyl ester, obtains fat A.
(3) fat A 300g is mixed with arachidonic acid 600g, be placed in four-hole boiling flask, stir and be warming up to 60 DEG C and keep constant, add 700ml octane, add sn-1,3 specific lipase 37g, condensing reflux pipe is installed, is maintained reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain the composition that contains 2-palmitin after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 50.8wt%.
Embodiment 15
(1) provide a kind of shortening, it is that 23.0%, 2 palmitic acid content is 16.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate shortening 200g, ethyl palmitate 600g, lipase 10g and deionized water 1g are placed in to flask, add helium protection, stir and be warming up to 60 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, molecular distillation method is removed fatty-acid ethyl ester, obtains fat A.
(3) fat A 300g is mixed with arachidonic acid 600g, be placed in four-hole boiling flask, stir and be warming up to 60 DEG C and keep constant, add 700ml octane, add sn-1,3 specific lipase 37g, condensing reflux pipe is installed, is maintained reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain the composition that contains 2-palmitin after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 52.6wt%.
Embodiment 16
(1) provide a kind of shortening, it is that 23.0%, 2 palmitic acid content is 16.9% that its palmitinic acid accounts for total fatty acids ratio.
(2) reaction substrate shortening 200g, ethyl palmitate 800g, lipase 10g and deionized water 1g are placed in to flask, add helium protection, stir and be warming up to 60 DEG C and keep constant, sustained reaction 8 hours.After reaction finishes, molecular distillation method is removed fatty-acid ethyl ester, obtains fat A.
(3) fat A 300g is mixed with arachidonic acid 600g, be placed in four-hole boiling flask, stir and be warming up to 60 DEG C and keep constant, add 700ml octane, add sn-1,3 specific lipase 37g, condensing reflux pipe is installed, is maintained reaction 8 hours, obtain mixing oil B.
(4) by mixing oil B purifying, the step of purifying includes but not limited to: remove by filter lipase, remove free fatty acids by molecular distillation again, obtain the composition that contains 2-palmitin after deodorization, detecting 2 upper palmitic acid contents by GC and thin-layer chromatography is 63.3wt%.
the application of the composition that contains 2-palmitin
The above-mentioned composition that contains 2-palmitin making can be used for the fields such as infant formula powder, baby formula ground rice, children's milk, acidophilus milk for child and the abnormal patient's of digestive function special diet, below only taking the abnormal patient's of digestive function special diet as example, introduce in detail the application of the composition of the 2-of containing palmitin of the present invention.
The composition that contains 2-palmitin that uses above-described embodiment 5 to make, carries out proportioning according to the following formulation:
Title Ratio (%) in product
The composition that contains 2-palmitin 10
Selected rice 85.9
White sugar 3
Vitamin premix 0.1
Mineral substance premix 1
First rice is pulverized, obtained about 100-120 object ground rice.According to above-mentioned formula, the slip of preparation 45% solid substance after 5000rpm rotating speed cutting 25min, carries out homogeneous under 20MPa, obtains the slip after homogeneous.Then add 0.8% amylorrhexis 4hr, then gelatinization 45min at 85 DEG C.The slip that gelatinization is good carries out steam roller tube according to following parameter and is dried:
Vapor pressure Drum rotational speed Film thickness
0.45MPa 4rpm 2.5mm
Finally can obtain special diet ground rice moisture content 3% left and right, that contain 2-palmitin by above operation.

Claims (10)

1. the preparation method who contains the composition of 2-palmitin, comprises the steps:
(1) provide the glyceryl ester that contains palmitic acid residues;
(2) glyceryl ester that contains palmitic acid residues is mixed and carries out transesterify with palmitinic acid, palmitate or palmitic non-glyceride esters, obtain fat A;
(3) fat A and unsaturated fatty acids or its nonglyceride are carried out to Sn-1,3 enzymatic directed inter-esterification, obtain mixing oil B;
(4) mixing oil B is refining, obtain the composition that contains 2-palmitin.
2. the preparation method of the composition that contains 2-palmitin according to claim 1, it is characterized in that: described palmitate comprises Sodium pentadecanecarboxylate or potassium palmitate, palmitate is not more than 4:1 with the weight ratio of the glyceryl ester that contains palmitic acid residues, be preferably 1:500-4:1, be more preferably 1:50-1:1.
3. the preparation method of the composition that contains 2-palmitin according to claim 1, it is characterized in that: described palmitic non-glyceride esters comprises Uniphat A60 or ethyl palmitate, palmitic non-glyceride esters is not more than 4:1 with the weight ratio of the glyceryl ester that contains palmitic acid residues, be preferably 1:500-4:1, be more preferably 1:50-1:1.
4. the preparation method of the composition that contains 2-palmitin according to claim 1, is characterized in that: palmitinic acid is not more than 4:1 with the weight ratio of the glyceryl ester that contains palmitic acid residues, is preferably 1:500-4:1, is more preferably 1:50-1:1.
5. according to the arbitrary described preparation method who contains 2-palmitin composition of claim 1-4, it is characterized in that: in the transesterify system of step (2), further add water, water is less than 5wt% with the proportion of the glyceryl ester that contains palmitic acid residues, preferably be less than 2wt%, be more preferably less than 1wt%.
6. according to the arbitrary described preparation method who contains 2-palmitin composition of claim 1-4, it is characterized in that: after the transesterify of step (2) finishes, through making fat A.
7. according to the preparation method of the arbitrary described composition that contains 2-palmitin of claim 1-4, it is characterized in that: in step (3), the weight ratio of fat A and unsaturated fatty acids or its nonglyceride is 2:1-1:10, is preferably 1:1-1:3.
8. according to the preparation method of the arbitrary described composition that contains 2-palmitin of claim 1-4, it is characterized in that: in the enzymatic directed inter-esterification system of step (3), further add solvent, described solvent comprises hexane, hexanaphthene, octane or octane-iso.
9. according to the preparation method of the arbitrary described composition that contains 2-palmitin of claim 1-4, it is characterized in that: described unsaturated fatty acids comprises oleic acid, linolic acid, linolenic acid, arachidonic acid, timnodonic acid and docosahexenoic acid.
10. a composition that contains 2-palmitin, is characterized in that: described in contain 2-palmitin composition be obtained according to arbitrary preparation method in claim 1-9.
CN201410319597.6A 2014-07-07 2014-07-07 Method for preparing composition containing 2-palmitin Pending CN104087626A (en)

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PCT/CN2015/082488 WO2016004825A1 (en) 2014-07-07 2015-06-26 Composition comprising 2-palmitic acid glyceride and preparation method thereof, structural fat comprising 1, 3-diunsaturated fatty acid-2-palmitic acid and preparation method, and special food

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