CN106905359B - A kind of preparation method for producing the refined deoiled phosphatides of medicinal high-purity phosphatidyl choline - Google Patents
A kind of preparation method for producing the refined deoiled phosphatides of medicinal high-purity phosphatidyl choline Download PDFInfo
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- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 128
- 239000000284 extract Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000001035 drying Methods 0.000 claims abstract description 20
- 150000002978 peroxides Chemical class 0.000 claims abstract description 18
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 238000000605 extraction Methods 0.000 claims description 36
- 239000012452 mother liquor Substances 0.000 claims description 29
- 238000003756 stirring Methods 0.000 claims description 29
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 17
- 239000004250 tert-Butylhydroquinone Substances 0.000 claims description 11
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 10
- 238000001291 vacuum drying Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000498 cooling water Substances 0.000 claims description 8
- 238000007599 discharging Methods 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 4
- -1 A Chemical compound 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 9
- 238000000746 purification Methods 0.000 description 6
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 5
- 239000002932 luster Substances 0.000 description 5
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 5
- 150000003905 phosphatidylinositols Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 210000004681 ovum Anatomy 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 108010000126 Gabolysat PC60 Proteins 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000002804 anti-anaphylactic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000000468 intravenous fat emulsion Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- 229940067626 phosphatidylinositols Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provide it is a kind of it is easier, at low cost, can large-scale industrial production lighter color, peroxide value it is low, the especially method of acetone insoluble matter height and the low refined deoiled phosphatides of lysophosphatidyl choline content, including extract, centrifuge repeatedly, drying and other steps.
Description
Technical field
The present invention relates to a kind of methods of refined deoiled phosphatides, in particular for producing the essence of medicinal high-purity phosphatidyl choline
The preparation method of deoiled phosphatides processed, belongs to technical field of chemical purification.
Background technology
Phosphatide is a kind of phosphorous fatty material for being present in living nature, is a kind of mixture, mainly by phosphatidyl choline (ovum
Phosphatide, PC), phosphatidyl-ethanolamine (cephalin, PE), phosphatidylserine (PS), phosphatidylinositols (lipositol, PI) and phosphorus
The compositions such as resin acid (PA).Phosphatide is natural emulsifier and surfactant, has higher nutritive value and special physiology
Characteristic can be widely applied to the fields such as medicine, food, feed, fiber, cosmetics, leather, dyeing, chemical industry, environmental protection.Phosphatide is not
High temperature resistant, 80 DEG C start to become brown, and 120 DEG C start to decompose, oxidizable rancid and make to darken, not easy to maintain.Wherein phosphatide
Phatidylcholine is one of main component of phosphatide, is a kind of amphiphatic molecule, is made of hydrophilic head and hydrophobic tail portion, also known as ovum
Phosphatide.
Lecithin is known as the third nutrient arranged side by side with protein, vitamin.Lecithin content is below big 55%
Certain applications can also apply in health food, nutraceutical and do medical auxiliary materials.60%-80% is used in cosmetics, pharmaceutic adjuvant
In, 90% or more is mainly used in pharmaceutical industry.By its purity height, be generally divided into PC50, PC60, PC70, PC80,
PC90,PC95.With deepening continuously to the research that phosphatide acts in terms of medicine and pharmacology, pharmacy industry is to high-purity phosphatide graded product
Demand increasingly increases.Especially high-purity phosphatidyl choline, it, which not only has, reduces the important physiology work such as atherosclerosis
With, and can be used for preparing intravenous fat emulsion infusion；As the liposome of anticancer drug and gene drug carriers, drug effect is being improved
Toxic side effect aspect is significant in efficacy with reducing；It is alternatively arranged as penicillin additive, is played and is promoted drug absorption, mitigates pain increase
Curative effect, antianaphylactic effect.
Under normal conditions, mixture of phospholipids obtains deoiled phosphatides after extraction, is further obtained by extraction purification
Medicinal high-purity phosphatidyl choline.It point is carried currently, the extracting method of medicinal phosphatidyl choline is mainly organic solvent extractionprocess, chromatography
Method and supercritical CO2Extraction, and due to using CO2Non-toxic gas can avoid the pollution problem brought using organic solvent, so
It has been generally acknowledged that the latter is more satisfactory, but this method is not only of high cost, and de-oiling is not thorough, and to obtain high-purity medicinal phosphatidyl courage
Alkali must finally use the de-oilings such as solvent such as acetone.It should be noted that high-purity phosphatidyl choline in order to obtain, need to take off
Oily phosphatide is as the further extraction purification of raw material, thus the complexity of the raw material of its extraction purification and of high cost low, to being
The no phosphatidyl choline for obtaining high-purity that can quickly, inexpensive is most important.The deoiled phosphatides obtained in the prior art,
There is the problems such as acetone insoluble matter is low, peroxide value is high, lysolecithin content is high, in the medicinal high-purity phosphatidyl choline of subsequent extracted
When, also to take reduces lysophosphatidyl choline and removing soybean oil processing step, causes extraction process complicated, cost mistake
It is high.A kind of method for extracting the refined deoiled phosphatides of high purity medical phosphatidyl choline is thus studied, is to solve high-purity
One vital factor of phosphatidyl choline extraction and purification process.In consideration of it, it is low to study a kind of lighter color, peroxide value,
Especially acetone insoluble matter content is high and the preparation method of the low deoiled phosphatides of lysophosphatidyl choline content, be the present invention urgently
It solves the problems, such as.
Invention content
Therefore, technical problem to be solved by the present invention lies in overcome deoiled phosphatides peroxide value in the prior art it is high,
The technological deficiency that acetone insoluble matter is low, lysophosphatidyl choline content is high, to provide it is a kind of it is easier, at low cost, can advise greatly
The industrial lighter color of mould, peroxide value are low, and it is refined that especially acetone insoluble matter is high and lysophosphatidyl choline content is low
The method of deoiled phosphatides.
For this purpose, the present invention provides a kind of preparation method of refined deoiled phosphatides, including：
A, high-purity acetone is added in extractor, nitrogen is passed through into extractor and removes air, TBHQ is added and has
Machine acid, stirring are slowly added to liquid phosphatide, open condensed water, are extracted；
B, it by extract liquor quiescent setting in step A, extracts upper layer mother liquor out, adds high-purity acetone and extractor is added together
In, it is passed through nitrogen into extractor and removes air, adds TBHQ and organic acid, stirs, is extracted；Repeat step B4 times；
C, it by extract liquor quiescent setting in step B, extracts upper layer mother liquor out, adds high-purity acetone and extractor is added together
In, it is passed through nitrogen into extractor and removes air, adds TBHQ, stirs, is extracted；Repeat step C3 times；
D, after extracting upper layer mother liquor, lower slurry goes to centrifuge, and mother liquor rectifying obtains filter cake, and rotatory vacuum drying machine is dry
It is dry, cooling water temperature is passed through to 25 DEG C of dischargings, obtains powdered refined deoiled phosphatides.
In the preparation method of above-mentioned refined deoiled phosphatides, liquid phosphatide in the step A：High-purity acetone:TBHQ:It is organic
Sour ratio is mass volume ratio (W/V/W/W) 1:2:0.0002:0.002-1:6:0.0006:0.006, preferably 1:3:0.0003:
0.003-1:5:0.0005:0.005, most preferably 1:4:0.0004:0.004.
In the preparation method of above-mentioned refined deoiled phosphatides, the liquid phosphatide in step A is relative to high-purity in the step B
The additional proportion of acetone is mass volume ratio (W/V) 1:1-1:3, preferably 1:2.
In the preparation method of above-mentioned refined deoiled phosphatides, organic acid is citric acid, tartaric acid, apple in step A, B
It is one or more in acid.
In the preparation method of above-mentioned refined deoiled phosphatides, speed of agitator is 400-800r/min in described step A, B, C, excellent
Select 600r/min.
In the preparation method of above-mentioned refined deoiled phosphatides, extraction temperature≤20 DEG C in described step A, B, C, preferably extraction temperature
≤ 15 DEG C are spent, extraction mixing time is 20-40min, preferably 30min in step A, and it is 10- that mixing time step B, is extracted in C
30min, preferably 20min.
Being dried in vacuo condition in the preparation method of above-mentioned refined deoiled phosphatides, in the step D is：50 DEG C of drying temperature,
Vacuum degree reaches stops drying after -0.098MPa after 30min.
In the preparation method of above-mentioned refined deoiled phosphatides, the ingredient of liquid phosphatide is in the step A：Acetone insoluble matter
62.3%, peroxide value 0.3meq/kg, LPC lysophosphatidyl choline 1.12%, amber viscous fluid；It is smart in the step D
The ingredient of deoiled phosphatides processed is：Acetone insoluble matter 99.2%, LPC0.2%, peroxide value 0.2, buff powder.
The applicant is by the discovery that studies for a long period of time, and during carrying out de-oiling using acetone, general extraction temperature is higher,
Time is longer.However, even if simply control extraction temperature keeps low-temperature extraction, since phosphatide easily aoxidizes, even if being added to
The antioxidants such as TBHQ, or be passed through nitrogen protection and prevent oxydrolysis, still it has been easy part in the deoiled phosphatides being obtained by extraction
Phosphatide is aoxidized, and a degree of oxidation product is generated, and is had residual in follow-up extraction, drying process, is led to final de-oiling phosphorus
Fat prod color and luster is deep, peroxide value is high, acetone insoluble matter is low, lysophosphatidyl choline content is high.Thus, the present inventor is adding
The antioxidants such as TBHQ are passed through on the basis of nitrogen protection prevents the safeguard measures such as oxydrolysis, in especially being extracted at first four times
It has selected organic acid to be added in acetone soln, has increased the polarity of acetone to increase lysophosphatidyl choline in acetone molten
Lysophosphatidyl choline in raw material is removed, the lysophosphatidyl choline content in finished product deoiled phosphatides is made greatly to drop by Xie Du
It is low.
The above technical solution of the present invention has the following advantages over the prior art：
1, in the preparation method of refined deoiled phosphatides of the present invention, by adding organic acid in acetone, increase haemolysis
The solubility of phosphatidyl choline in acetone, to reduce content of the lysophosphatidyl choline in deoiled phosphatides, after reducing
Continuous polishing purification extracts the difficulty and cost of medicinal phosphatidyl choline, and in the preparation whole flow of deoiled phosphatides obtained by this technique
It is natural material, and lighter color, the peroxide value of deoiled phosphatides obtained by this technique are low, only can obtain third after repeatedly extraction
The powdered refined deoiled phosphatides that ketone insolubles content is high, lysophosphatidyl choline content is low, peroxide value is low, yield are high, pure
Degree height, lighter color.
2, in extraction process, select acetone as de-oiling solvent, addition antioxidant increases deoiled phosphatides as protective agent
Shelf-life, while nitrogen is passed through to prevent raw material during anti-avulsion oil or product oxydrolysis.
3, generally, it is considered that extraction temperature is excessively high or drying temperature is high, it can make containing for phosphatidyl choline in deoiled phosphatides
Amount reduces, however inventor is by the addition of organic acid, and combines control and drying temperature and the vacuum degree of extractor temperature
Control, ensure that degree of oxidation is low while phosphatide removes lysophosphatidyl choline in degreasing process.
Specific implementation mode
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.
The organic acids such as citric acid used, tartaric acid, malic acid are the food-grade that commercially available purity is more than 99% in embodiment
Product.High-purity acetone soln purity 99.5%.
Prepared by embodiment 1-3 addition citric acids refines deoiled phosphatides
Embodiment 1
In the extractor of 1500L, the acetone of 800L purity 99.5% is first added, nitrogen is passed through into extractor and removes sky
Gas adds 80gTBHQ and 800g citric acids, opens stirring, mixing speed is 600r/min, is slowly added to 200kg liquid phosphorus
Fat (acetone insoluble matter 62.3%, LPC1.12%, peroxide value 0.3) opens condensed water, and extraction temperature controls within 15 DEG C,
Extraction stirring 30min.
Quiescent setting 30min extracts upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, into extractor
It is passed through nitrogen and removes air, add 40gTBHQ and 400g citric acids, open stirring, extract 20min.Repeat above step 4
It is secondary.
After extracting upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, nitrogen removing is passed through into extractor
Air adds 40gTBHQ, opens stirring, extracts 20min.Repeat above step 3 times.
After extracting upper layer mother liquor 400L, lower slurry goes to centrifuge, and mother liquor goes rectifying to obtain the acetone of purity 99.5%
It reuses, filter cake 180kg, goes rotatory vacuum drying machine to dry, 50 DEG C of drying temperature, after vacuum degree reaches -0.098MPa
Stop drying after 30min, is passed through cooling water temperature to 25 DEG C of dischargings, obtains the refined deoiled phosphatides of 120kg, acetone insoluble matter
99.2%, LPC0.2%, peroxide value 0.2.
Embodiment 2
In the extractor of 1500L, the acetone of 600L purity 99.5% is first added, nitrogen is passed through into extractor and removes sky
Gas adds 80gTBHQ and 800g citric acids, opens stirring, mixing speed is 400r/min, is slowly added to 200kg liquid phosphorus
Fat (acetone insoluble matter 62.3%, LPC1.12%, peroxide value 0.3) opens condensed water, and extraction temperature controls within 20 DEG C,
Extraction stirring 40min.
Quiescent setting 30min extracts upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, into extractor
It is passed through nitrogen and removes air, add 40gTBHQ and 400g citric acids, open stirring, extract 20min.Repeat above step 4
It is secondary.
After extracting upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, nitrogen removing is passed through into extractor
Air adds 40gTBHQ, opens stirring, extracts 20min.Repeat above step 3 times.
After extracting upper layer mother liquor 400L, lower slurry goes to centrifuge, and mother liquor goes rectifying to obtain the acetone of purity 99.5%
It reuses, filter cake 183kg, goes rotatory vacuum drying machine to dry, 50 DEG C of drying temperature, after vacuum degree reaches -0.098MPa
Stop drying after 30min, is passed through cooling water temperature to 25 DEG C of dischargings, obtains the refined deoiled phosphatides of 122kg, acetone insoluble matter
99.0%, LPC0.3%, peroxide value 0.3.
Embodiment 3
In the extractor of 1500L, the acetone of 1000L purity 99.5% is first added, nitrogen removing is passed through into extractor
Air adds 80gTBHQ and 300g citric acids, opens stirring, mixing speed is 600r/min, is slowly added to 200kg liquid
Phosphatide (acetone insoluble matter 62.3%, LPC1.12%, peroxide value 0.3), open condensed water, extraction temperature control 15 DEG C with
It is interior, extraction stirring 30min.
Quiescent setting 30min extracts upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, into extractor
It is passed through nitrogen and removes air, add 40gTBHQ and 200g citric acids, open stirring, extract 20min.Repeat above step 4
It is secondary.
After extracting upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, nitrogen removing is passed through into extractor
Air adds 40gTBHQ, opens stirring, extracts 20min.Repeat above step 3 times.
After extracting upper layer mother liquor 400L, lower slurry goes to centrifuge, and mother liquor goes rectifying to obtain the acetone of purity 99.5%
It reuses, filter cake 178kg, goes rotatory vacuum drying machine to dry, 50 DEG C of drying temperature, after vacuum degree reaches -0.098MPa
Stop drying after 30min, is passed through cooling water temperature to 25 DEG C of dischargings, obtains the refined deoiled phosphatides of 118kg, acetone insoluble matter
99.1%, LPC0.4%, peroxide value 0.4.
Comparative example 1-3 is not added with citric acid and prepares refined deoiled phosphatides
Comparative example 1
In the extractor of 1500L, the acetone of 800L purity 99.5% is first added, nitrogen is passed through into extractor and removes sky
Gas adds 80gTBHQ, opens stirring, and mixing speed is 600r/min, is slowly added to 200kg liquid phosphatide, opens condensation
Water, extraction temperature control within 15 DEG C, extraction stirring 30min.
Quiescent setting 30min extracts upper layer mother liquor 400L, the acetone of 400L purity 99.5% is added, into extractor
It is passed through nitrogen and removes air, add 40gTBHQ, open stirring, extract 20min.Repeat above step 7 times.
After extracting upper layer mother liquor 400L, lower slurry goes to centrifuge, and mother liquor goes rectifying to obtain the acetone of purity 99.5%
It reuses, filter cake 182kg, goes rotatory vacuum drying machine to dry, 50 DEG C of drying temperature, after vacuum degree reaches -0.098MPa
Stop drying after 30min, is passed through cooling water temperature to 25 DEG C of dischargings, obtains the powdered deoiled phosphatides of 121kg.
Comparative example 2
In the extractor of 1500L, the acetone of 600L purity 99.5% is first added, nitrogen is passed through into extractor and removes sky
Gas adds 80gTBHQ, opens stirring, and mixing speed is 400r/min, is slowly added to 200kg liquid phosphatide, opens condensation
Water, extraction temperature control within 20 DEG C, extraction stirring 40min.
Quiescent setting 30min extracts upper layer mother liquor 400L, the acetone of 200L purity 99.5% is added, into extractor
It is passed through nitrogen and removes air, add 40gTBHQ, open stirring, extract 20min.Repeat above step 7 times.
After extracting upper layer mother liquor 400L, lower slurry goes to centrifuge, and mother liquor goes rectifying to obtain the acetone of purity 99.5%
It reuses, filter cake 184kg, goes rotatory vacuum drying machine to dry, 50 DEG C of drying temperature, after vacuum degree reaches -0.098MPa
Stop drying after 30min, is passed through cooling water temperature to 25 DEG C of dischargings, obtains the powdered deoiled phosphatides of 122kg.
Comparative example 3
In the extractor of 1500L, the acetone of 1000L purity 99.5% is first added, nitrogen removing is passed through into extractor
Air adds 80gTBHQ, opens stirring, and mixing speed is 800r/min, is slowly added to 200kg liquid phosphatide, opens condensation
Water, extraction temperature control within 15 DEG C, extraction stirring 30min.
Quiescent setting 30min extracts upper layer mother liquor 400L, the acetone of 600L purity 99.5% is added, into extractor
It is passed through nitrogen and removes air, add 40gTBHQ, open stirring, extract 20min.Repeat above step 7 times.
After extracting upper layer mother liquor 400L, lower slurry goes to centrifuge, and mother liquor goes rectifying to obtain the acetone of purity 99.5%
It reuses, filter cake 178kg, goes rotatory vacuum drying machine to dry, 50 DEG C of drying temperature, after vacuum degree reaches -0.098MPa
Stop drying after 30min, is passed through cooling water temperature to 25 DEG C of dischargings, obtains the powdered deoiled phosphatides of 118kg.
The component of deoiled phosphatides is analyzed, acetone insoluble matter content average out to 99.1%, passes through in deoiled phosphatides
HPLC is analyzed, the HPLC chromatogram of standard of comparison, by external standard method calculating each component content, obtains that the results are shown in Table 1.
The each component content of 1 deoiled phosphatides of table
As shown in Table 1, the key component of deoiled phosphatides is phosphatidyl-ethanolamine (PE), phosphatidyl choline (PC) and phosphatidyl
Inositol (PI).Embodiment 1-3 is compared with the deoiled phosphatides of comparative example 1-3, PC content balance examples 1- in embodiment 1-3 deoiled phosphatides
PC contents are high in 3 deoiled phosphatides, and PE contents are slightly lower, and PI contents are substantially suitable, and especially PC contents are up in deoiled phosphatides
23.5%.
The indices of deoiled phosphatides are analyzed, analysis result is shown in Table 2.
The indices-of 2 deoiled phosphatides of table meet GB28401-2012
As shown in Table 2, the lysophosphatidyl choline content of the deoiled phosphatides in embodiment is said obviously than low in comparative example
It is bright that by the way that organic acid is added in acetone to reduce the method for the lysophosphatidyl choline content in deoiled phosphatides highly effective.Third
Ketone insoluble matter value is higher, illustrates that the de-oiling effect of deoiled phosphatides is better, soybean oil contained by product is fewer.Embodiment 1-3 and comparison
The deoiled phosphatides of example 1-3 are compared, the acetone insoluble matter higher of the deoiled phosphatides in embodiment, and acid value is lower.
The appearance luster of deoiled phosphatides is analyzed, analysis result is shown in Table 3.
The appearance luster of 3 deoiled phosphatides of table
| Index | Color |
| Embodiment 1 | It is yellowish |
| Embodiment 2 | It is yellowish |
| Embodiment 3 | It is yellowish |
| Comparative example 1 | Micro- Huang |
| Comparative example 2 | It is slightly yellow |
| Comparative example 3 | It is slightly yellow |
As shown in Table 3, the color and luster of deoiled phosphatides is more shallow, illustrates that the degree that it is aoxidized is lighter.Embodiment 1-3 and comparative example
The deoiled phosphatides of 1-3 are compared, and color and luster is more shallow in deoiled phosphatides, lighter by degree of oxidation.
Phosphatide is placed very oxidizable rotten in exposure air, and especially under temperature higher state, color adds rapidly
It is deep, therefore when preparing refined deoiled phosphatides, should be carried out in nitrogen atmosphere at a lower temperature as far as possible.From this experimental result
It sums up to draw a conclusion：Extraction temperature be less than 15 DEG C, vacuum drying temperature be less than 50 DEG C, vacuum degree -0.098MPa, lead to nitrogen,
Addition organic acid and antioxidant are the optimum conditions for the refined deoiled phosphatides for preparing medicinal high-purity phosphatidyl choline in acetone.
Obviously, the specific type of the organic acid used in above-described embodiment is only intended to clearly illustrate example,
And it does not limit the embodiments.For those of ordinary skill in the art, may be used also on the basis of the above description
To make other variations or changes in different ways.There is no necessity and possibility to exhaust all the enbodiments.And thus
The obvious changes or variations extended out are still within the protection scope of the invention.
Claims (11)
1. a kind of preparation method for producing the refined deoiled phosphatides of medicinal high-purity phosphatidyl choline, including：
A, high-purity acetone is added in extractor, nitrogen is passed through into extractor and removes air, adds TBHQ and citric acid,
Stirring is slowly added to liquid phosphatide, opens condensed water, is extracted；
B, by extract liquor quiescent setting in step A, upper layer mother liquor is taken, is added in extractor together with high-purity acetone, to extraction
It is passed through nitrogen in tank and removes air, adds TBHQ and citric acid, stirs, is slowly added to liquid phosphatide, opens condensed water, carries out
Extraction；Repeat step B 4 times；
C, it by extract liquor quiescent setting in step B, extracts upper layer mother liquor out, adds high-purity acetone and be added in extractor together,
It is passed through nitrogen into extractor and removes air, adds TBHQ, stirs, is extracted；Repeat step C 3 times；
D, after extracting upper layer mother liquor, lower slurry goes to centrifuge, and mother liquor rectifying obtains filter cake, and rotatory vacuum drying machine is dried,
Cooling water temperature is passed through to 25 DEG C of dischargings, obtains powdered refined deoiled phosphatides.
2. according to the method described in claim 1, liquid phosphatide in the step A：High-purity acetone：TBHQ：Citric acid：Acetone
Solution proportion is mass volume ratio (W/V/W/W) 1:2:0.0002:0.002-1:6:0.0006:0.006.
3. according to the method described in claim 1, liquid phosphatide in the step A：High-purity acetone：TBHQ：Citric acid：Acetone
Solution proportion is mass volume ratio (W/V/W/W) 1:3:0.0003:0.003-1:5:0.0005:0.005.
4. according to the method described in claim 1, the liquid phosphatide in step A is relative to high-purity acetone in the step B
Additional proportion is mass volume ratio (W/V) 1:1-1:3.
5. according to the method described in claim 1, the liquid phosphatide in step A is relative to high-purity acetone in the step B
Additional proportion is mass volume ratio (W/V) 1:2.
6. according to the method described in claim 1, speed of agitator is 400-800r/min in described step A, B, C.
7. according to the method described in claim 1, speed of agitator is 600r/min in described step A, B, C.
8. extract stirring according to the method described in claim 1, extraction temperature≤20 DEG C in described step A, B, C, in step A
Between be 20-40min, step B, in C extract mixing time be 10-30min.
9. extract stirring according to the method described in claim 1, extraction temperature≤15 DEG C in described step A, B, C, in step A
Between be 30min, step B, in C extract mixing time be 20min.
10. being dried in vacuo condition according to claim 1-9 any one of them methods, in the step D is：Drying temperature 50
DEG C, vacuum degree reaches stops drying after -0.098MPa after 30min.
11. according to claim 1-9 any one of them methods, the ingredient of liquid phosphatide is in the step A：Acetone insoluble matter
62.1%, n-hexane insoluble matter 0.3%, peroxide value 0.3meq/kg, lysophosphatidyl choline 1.12%, amber sticky stream
Body；The ingredient of refined deoiled phosphatides is in the step D：Acetone insoluble matter 99.2%, LPC0.2%, peroxide value 0.2 are pale yellow
Color powder, wherein phosphatidylcholine content 23.5%.
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