CN105037133B - A kind of method that nervonic acid is extracted from malania oleifera - Google Patents
A kind of method that nervonic acid is extracted from malania oleifera Download PDFInfo
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- CN105037133B CN105037133B CN201510501759.2A CN201510501759A CN105037133B CN 105037133 B CN105037133 B CN 105037133B CN 201510501759 A CN201510501759 A CN 201510501759A CN 105037133 B CN105037133 B CN 105037133B
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- 241000928579 Malania oleifera Species 0.000 title claims abstract description 76
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 title claims abstract description 37
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 title claims abstract description 37
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000001537 neural effect Effects 0.000 claims abstract description 20
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000012530 fluid Substances 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 13
- 238000007127 saponification reaction Methods 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 239000000284 extract Substances 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 6
- 210000005036 nerve Anatomy 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 238000000605 extraction Methods 0.000 claims description 86
- 238000000926 separation method Methods 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 17
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000013557 residual solvent Substances 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 238000011109 contamination Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 7
- 238000005520 cutting process Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000033228 biological regulation Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- AINIZSBLAFHZCP-KHPPLWFESA-N methyl cis-15-tetracosenoate Chemical class CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)OC AINIZSBLAFHZCP-KHPPLWFESA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 240000002234 Allium sativum Species 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001252483 Kalimeris Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 241001460678 Napo <wasp> Species 0.000 description 1
- 241000221014 Olacaceae Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 241000410468 Pterostyrax Species 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 240000007662 Tieghemella heckelii Species 0.000 description 1
- 235000000587 Tieghemella heckelii Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 230000007433 nerve pathway Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method that nervonic acid is extracted from malania oleifera.It is an object of the invention to overcome the problems such as low prior art products yield, environmental pollution.To reach above-mentioned purpose, the technical scheme steps of use are as follows：（One）Use supercritical CO2Fluid extracts Malania Oleifera Oil from malania oleifera；（Two）Malania Oleifera Oil carries out saponification process, and to obtain Malania Oleifera Oil saponified；（Three）Malania Oleifera Oil is saponified by supercritical CO2The unsaponifiable matter such as fluid removal high triacontanol obtain slightly neural hydrochlorate；（Four）Thick nerve hydrochlorate is acidified, filtering, washing, dry after neural acid product.Supercritical CO of the present invention2The neural acid product of technology gained is containing nervonic acid up to more than 50%, and the preparation process is simple is easy to operate, with the free of contamination feature of efficient cryogenic, is adapted to industrialized production.
Description
Technical field
The invention belongs to field of plant extraction, it is related to a kind of method that nervonic acid is extracted from malania oleifera.
Background technology
Nervonic acid also known as Nervonic Acid, chemical entitled nervonie acid is a kind of long-chain monounsaturated fatty acid
Acid, molecular formula is C24H46O2, relative molecular mass is 366.6, is at normal temperatures white plates crystal, can be dissolved in alcohol, is not dissolved in
Water, 39~40 DEG C of fusing point.
Nervonic acid be scientists from all over the world generally acknowledge can repair dredging injured brain nerve pathway --- nerve fibre, and promote
The economic benefits and social benefits material of nerve cell regeneration.Nervonic acid is the core natural component of cerebral nerve fiber and nerve cell.Nervonic acid
Shortage will cause the cerebral diseases such as cerebral apoplexy sequela, senile dementia, brain paralysis, encephalatrophy, failure of memory, insomnia forgetfulness.God
Synthesis itself is difficult through sour human body, it is necessary to by food intake supplement.
Malania oleifera belongs to aiphyllium for Olacaceae malania oleifera, alias be mountain paulownia really, Tieghemella heckelii Pierre, after kalimeris（Strong voice）
Deng, it is the distinctive single Pterostyrax plant of China, the tang of southeastern Yunnan and West Guangxi is distributed in, it is concentrated mainly on red
Region to the west of water river-line of Nanning-Longzhou one, Guangxi main wants the place of production for bar horse, Fengshan, Tianlin County, Tian Le, works in peace and contentment, and moral is precious, icepro
The counties such as cloud, Long Lin, Napo County and Longzhou.Malania oleifera benevolence contains grease 50 ~ 60%, with C in aliphatic acid18~C24Based on, wherein nervonic acid
Content is up to 40 ~ 60%.
It is reported that, the relevant report that separation nervonic acid is extracted from malania oleifera is less.Xiong Deyuan etc. is in " crystallisation separation garlic
The crude product mixing fat obtained after saponification, acidifying, washing to Malania Oleifera Oil in neural sour solvent Selecting research in a head fruit oil " text
Fat acid has carried out the research of solvent crystallization separating-purifying, although the content of nervonic acid is higher in end-product（Reach as high as 75.39%）,
But the rate of recovery is relatively low（Only up to 59.74%）.The weak point of the preparation technology is also resided in：It is big in extraction and purge process
Amount has used the organic solvents such as petroleum ether, ethanol, has certain harmful effect to environment.Hao Xuya etc. is " in Malania Oleifera Oil
The nervonic acid in Malania Oleifera Oil is separated using urea adduct method in the separating-purifying research of nervonic acid " paper, equally
There is the rate of recovery low（Only 46.81%）And the problems such as environmental pollution.
The content of the invention
It is existing to overcome the present invention solves the technical problem of a kind of method that nervonic acid is extracted from malania oleifera is provided
There is the problems such as low technical products yield, environmental pollution.
A kind of method that nervonic acid is extracted from malania oleifera that the present invention is provided, is realized by following steps：
（1）Use supercritical CO2Fluid extracts Malania Oleifera Oil from malania oleifera；
（2）Malania Oleifera Oil carries out saponification 3H and obtains malania oleifera oil soap with 20% sodium hydrate aqueous solution in 95 ~ 100 DEG C of water-baths
Compound；
（3）Malania Oleifera Oil is saponified by supercritical CO2The unsaponifiable matter such as fluid removal high triacontanol obtain slightly neural hydrochlorate；
（4）Thick nerve hydrochlorate be acidified through 10% sulfuric acid solution, filter, washing, dry after obtain neural acid product.
Step（1）Described in supercritical CO2The extraction conditions of extraction is：Extracting pressure in extraction kettle used is
15MPa, extraction temperature is 40 DEG C, extraction extraction time used 2 hours；Pressure during extraction in separation reactor I used is 6MPa,
Temperature in separation reactor I is 35 DEG C；Pressure in separation reactor I I used during extraction is 4MPa, and the temperature in separation reactor I I is 35
℃。
Step（3）Described in pass through supercritical CO2Unsaponifiable matter and residual during extraction removing Malania Oleifera Oil is saponified is molten
Agent, extracting pressure used is 15MPa, and extraction temperature is 35 DEG C, and extraction time is 1h.
It is a further object to provide application of the methods described in nervonic acid is extracted from malania oleifera.
It is raw material that the present invention uses the malania oleifera rich in nervonic acid, and separates nervonic acid process for being extracted from malania oleifera
Present in above mentioned problem, using the supercritical CO without entrainer2Fluid extraction obtains Malania Oleifera Oil, the method efficient cryogenic without
Pollution.And using saponification, CO2Supercritical fluid technique removal of impurities, the heavy method of acid, can desolvation water, it is carried out further pure
Change, the unsaponifiable matter such as removing saponified middle-and-high-ranking alkanol of Malania Oleifera Oil.The inventive method is quick, efficient, noresidue, compared with solvent method
Abstraction impurity removal can reduce product loss, and cost is lower.Neural acid content is reachable in the neural acid product that the present invention is prepared
50%, although content is low compared with document, but the rate of recovery is 75% or so, and method process is simple is easy to operate, with short production cycle, environment
Close friend, supercritical CO2Fluid technique environmental protection, is adapted to industrialized production.
Brief description of the drawings
Fig. 1 is the GC-MS figures of extract of the typical case rich in nervonic acid（Embodiment 7）.
Specific embodiment
The technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
All other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model of present invention protection
Enclose.
Embodiment one
Malania oleifera 4.00kg after shelling, cutting into slices is fitted into 20L extraction kettles, 40 DEG C of extraction temperature, extracting pressure
15MPa, the pressure in separation reactor I is 6MPa, and the temperature in separation reactor I is 35 DEG C；Pressure in separation reactor I I used during extraction
Power is 4MPa, and the temperature in separation reactor I I is 35 DEG C, and extraction time 2 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.10kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 1h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 2.33kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction removes the unsaponifiable matter such as high triacontanol, extraction pressure
Power is 15MPa, and extraction temperature is 35 DEG C, extraction time 1h, obtains slightly neural hydrochlorate 2.16kg；Plus 5% sulfuric acid solution regulation pH to 2 ~
3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.42kg.
Embodiment two
Malania oleifera 4.50kg after shelling, cutting into slices is fitted into 20L extraction kettles, 45 DEG C of extraction temperature, extracting pressure
20MPa, the pressure in separation reactor I is 8MPa, and the temperature in separation reactor I is 35 DEG C；Pressure in separation reactor I I used during extraction
Power is 5MPa, and the temperature in separation reactor I I is 35 DEG C, and extraction time 2 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.29kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 2h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 2.56kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction removes the unsaponifiable matter such as high triacontanol, extraction pressure
Power is 15MPa, and extraction temperature is 40 DEG C, extraction time 1h, obtains slightly neural hydrochlorate 2.38kg；Plus 5% sulfuric acid solution regulation pH to 2 ~
3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.56kg.
Embodiment three
Malania oleifera 4.80kg after shelling, cutting into slices is fitted into 20L extraction kettles, 50 DEG C of extraction temperature, extracting pressure
25MPa, the pressure in separation reactor I is 10MPa, and the temperature in separation reactor I is 40 DEG C；Pressure in separation reactor I I used during extraction
Power is 6MPa, and the temperature in separation reactor I I is 40 DEG C, and extraction time 3 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.60kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 2h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 3.01kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction removes the unsaponifiable matter such as high triacontanol, extraction pressure
Power is 20MPa, and extraction temperature is 40 DEG C, extraction time 2h, obtains slightly neural hydrochlorate 2.77kg；Plus 5% sulfuric acid solution regulation pH to 2 ~
3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.87kg.
Example IV
Malania oleifera 4.00kg after shelling, cutting into slices is fitted into 20L extraction kettles, 40 DEG C of extraction temperature, extracting pressure
20MPa, the pressure in separation reactor I is 8MPa, and the temperature in separation reactor I is 45 DEG C；Pressure in separation reactor I I used during extraction
Power is 6MPa, and the temperature in separation reactor I I is 45 DEG C, and extraction time 2 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.12kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 2h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 2.36kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction remove the unsaponifiable matter such as high triacontanol and, extraction
Pressure is 20MPa, and extraction temperature is 40 DEG C, extraction time 2h, obtains slightly neural hydrochlorate 2.20kg；Plus 5% sulfuric acid solution adjust pH to
2 ~ 3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.44kg.
Embodiment five
Malania oleifera 4.50kg after shelling, cutting into slices is fitted into 20L extraction kettles, 45 DEG C of extraction temperature, extracting pressure
25MPa, the pressure in separation reactor I is 7MPa, and the temperature in separation reactor I is 50 DEG C；Pressure in separation reactor I I used during extraction
Power is 5MPa, and the temperature in separation reactor I I is 50 DEG C, and extraction time 3 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.31kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 3h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 2.62kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction removes the unsaponifiable matter such as high triacontanol, extraction pressure
Power is 20MPa, and extraction temperature is 45 DEG C, extraction time 2h, obtains slightly neural hydrochlorate 2.40kg；Plus 5% sulfuric acid solution regulation pH to 2 ~
3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.60kg.
Embodiment six
Malania oleifera 4.80kg after shelling, cutting into slices is fitted into 20L extraction kettles, 50 DEG C of extraction temperature, extracting pressure
25MPa, the pressure in separation reactor I is 9MPa, and the temperature in separation reactor I is 40 DEG C；Pressure in separation reactor I I used during extraction
Power is 7MPa, and the temperature in separation reactor I I is 45 DEG C, and extraction time 3 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.56kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 2h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 3.02kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction removes the unsaponifiable matter such as high triacontanol, extraction pressure
Power is 20MPa, and extraction temperature is 40 DEG C, extraction time 3h, obtains slightly neural hydrochlorate 2.70kg；Plus 5% sulfuric acid solution regulation pH to 2 ~
3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.81kg.
Embodiment seven
Malania oleifera 4.80kg after shelling, cutting into slices is fitted into 20L extraction kettles, 50 DEG C of extraction temperature, extracting pressure
25MPa, the pressure in separation reactor I is 8MPa, and the temperature in separation reactor I is 50 DEG C；Pressure in separation reactor I I used during extraction
Power is 6MPa, and the temperature in separation reactor I I is 45 DEG C, and extraction time 3 hours is obtained by extraction faint yellow Malania Oleifera Oil 2.35kg.Really
Oil 10% sodium hydroxide solution agitating heating backflow 2h, it is saponified that the rearmounted cold analysis of saponification goes out Malania Oleifera Oil, filters to obtain Malania Oleifera Oil
Saponified 2.60kg；Malania Oleifera Oil is saponified by supercritical CO2Fluid extraction removes the unsaponifiable matter such as high triacontanol, extraction pressure
Power is 25MPa, and extraction temperature is 50 DEG C, extraction time 3h, obtains slightly neural hydrochlorate 2.39kg；Plus 5% sulfuric acid solution regulation pH to 2 ~
3, heating stirring 2h, put it is cold after filtering, distillation be washed to neutral, dry thick nervonic acid 1.59kg.The sampled first of thick nervonic acid
Esterification, thick nervonic acid methyl esters GC-MS detect neural acid content be 50%.
Embodiment eight is detected to the thick nervonic acid of the gained of embodiment seven
Nervonic acid methyl esters reference substance preparation condition：It is accurate to weigh nervonic acid reference substance 0.6g, add 15ml methyl alcohol, 6ml bodies
Fraction is 47% BF3Diethyl ether solution is heated to reflux 10min in 70 ~ 80 DEG C of water-baths, after cooling, pours into separatory funnel, plus
10ml saturated aqueous common salts, with 15ml n-hexane extractions 3 times, merge supernatant, are settled in 100ml volumetric flasks with n-hexane, match somebody with somebody
Generating nervous acid methacrylate standard solution.
Thick nervonic acid esterification sample preparation condition：Thick nervonic acid 0.6g is accurately weighed, remaining step is ibid.
GC-MS testing conditions：The nonpolar chromatographic columns of HP-5MS, 60m*0.25mm*0.25 μm, carrier gas is high pure nitrogen, pure
Degree 99.995%.Temperature programming：160 DEG C of holding 2min, 270 DEG C are risen to 4 DEG C/min, keep 20min, split ratio 1:50, sample introduction
270 DEG C of temperature of mouth, 250 DEG C of interface temperature, the μ L of sample size 1.Mass Spectrometry Conditions（EI ion guns, electron energy 70eV, electron multiplier
Voltage 1.5kV, mass scan range m/z 30 ~ 400, full scan mode, solvent delay 3min）.Its data results such as Fig. 1
Shown, there is nervonic acid methyl esters absworption peak in retention time 37.639min.
Embodiments of the invention are the foregoing is only, the scope of the claims of the invention is not thereby limited, it is every to utilize this hair
Equivalent structure or equivalent flow conversion that bright description is made, or directly or indirectly it is used in other related technology necks
Domain, is included within the scope of the present invention.
Claims (3)
1. it is a kind of from malania oleifera extract nervonic acid method, it is characterised in that by following steps realize：
（1）Use supercritical CO2Fluid extracts Malania Oleifera Oil from malania oleifera；
（2）Malania Oleifera Oil carries out saponification process, and to obtain Malania Oleifera Oil saponified；
（3）Malania Oleifera Oil is saponified by supercritical CO2Fluid removal high triacontanol unsaponifiable matter obtains slightly neural hydrochlorate；
（4）Thick nerve hydrochlorate is acidified, filtering, washing, dry after neural acid product；
Wherein step（1）Middle malania oleifera loads extraction kettle after shelling, section, 50 DEG C of extraction temperature, 15 ~ 25MPa of extracting pressure,
Pressure in separation reactor I is 7 ~ 10MPa, and the temperature in separation reactor I is 30 ~ 50 DEG C；Pressure in separation reactor I I used during extraction
Power is 4 ~ 5MPa, and the temperature in separation reactor I I is 30 ~ 50 DEG C, and extraction time 1 ~ 3 hour is obtained by extraction faint yellow Malania Oleifera Oil；
Step（2）It is middle that saponification process is carried out in 95 ~ 100 DEG C of water-baths with 20% sodium hydrate aqueous solution；Step（3）Use supercritical CO2
Unsaponifiable matter and residual solvent during fluid extraction removing Malania Oleifera Oil is saponified, extracting pressure are 15 ~ 25MPa, extraction temperature
It is 35 ~ 50 DEG C, extraction time is 1 ~ 3h, obtains slightly neural hydrochlorate.
2. the method that nervonic acid is extracted in a kind of malania oleifera according to claim 1, it is characterised in that step（4）In it is thick
Neural hydrochlorate is acidified using 10% sulfuric acid solution.
3. in a kind of malania oleifera according to claim 1 extract nervonic acid method from malania oleifera extract nervonic acid in
Application.
Priority Applications (1)
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| CN107445813A (en) * | 2017-08-10 | 2017-12-08 | 王显权 | The method that Malania Oleifera Oil prepares cyclopentadecanone |
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| CN1398844A (en) * | 2002-09-04 | 2003-02-26 | 杭州施惠泰食品化学有限公司 | Nervonic acid extracting and purifying production process |
| CN104629899A (en) * | 2014-12-30 | 2015-05-20 | 广州白云山汉方现代药业有限公司 | Method for extracting malania oleifera oil by virtue of supercritical CO2 fluid |
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