CN107312049A - A kind of method that Rhoifolin and Japan wax are extracted from Rhus succedanea - Google Patents
A kind of method that Rhoifolin and Japan wax are extracted from Rhus succedanea Download PDFInfo
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- CN107312049A CN107312049A CN201710580765.0A CN201710580765A CN107312049A CN 107312049 A CN107312049 A CN 107312049A CN 201710580765 A CN201710580765 A CN 201710580765A CN 107312049 A CN107312049 A CN 107312049A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
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- 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
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The present invention relates to a kind of method that Rhoifolin and vegetable wax are extracted from Rhus succedanea, Rhus succedanea after dried is extracted through petroleum ether, filter residue again with diluted acid alcoholic solution refluxing extraction, filter, be concentrated to dryness, dissolved with sour water, Rhoifolin and Japan wax sterling is made in upper resin adsorption, stepwise elution, condensing crystallizing.The inventive method is simple to operate, substantially increases the yield of Japan wax and Rhoifolin, significantly reduces the production cost of Japan wax and Rhoifolin, simplifies its production process, moreover it is possible to obtain substantial amounts of oily substance.Using Rhus succedanea as raw material is extracted, the utilization ratio of Rhus succedanea was both substantially increased, the added value of Rhus succedanea is improved again.
Description
Technical field
The present invention relates to a kind of technology that Rhoifolin and vegetable wax are extracted from Rhus succedanea, belong to Separation of Natural Products
Technical field.
Background technology
Japan wax is water insoluble, cold ethanol；It is dissolved in hot ethanol and benzene, toluene, ether, petroleum ether, carbon disulfide, chlorine
Change the organic solvents such as ethene.Especially it should be noted that Japan wax is with coming from dynamic plant minerals, through artificial compound or chemical synthesis
Many cosmetics fatty, lipid component, through heated mutually molten platform into homogeneous phase body.The main composition of Japan wax is full
Sum with undersaturated the third blue alcohol ester for mixing resin acid.Lacquer tree fat purposes is extremely extensive, and lacquer tree fat has food medicine healthcare function, in China
There is edible and medicinal custom some areas always, for cooking, deep fried foodstuff and making lacquer tree fat wine, lacquer tree fat tea, do not have to skin
There are allergy and toxic side effect, be also prevented from stomach trouble and hemostasis, be the perfect nutriment of puerpera and operator；Lacquer tree fat is also important
Industrial chemicals, put acid, 15%~35% oleic acid and 3%~5% stearic acid containing more than 70% palm fibre in lacquer tree fat, can directly divide
Acid, stearic acid, oleic acid and linoleic acid and its salt are put from refined palm fibre；The higher aliphatics such as triacontanol can also be refined from lacquer tree fat
Alcohol, is the significant surfaces activating agent of the industries such as soapmaking, washing, lubrication, plasticising, cosmetics, not only can put oil instead of import palm fibre,
And the domestic and international market of lacquer tree fat can be expanded；The fatty acid cane sugar ester processed by lacquer tree fat, isopropyl fatty acid ester in the world should
With quite varied, it is especially useful in terms of superior cosmetics, emulsifying agent.Lacquer tree fat will be replaced gradually as important industrial chemicals
Palm fibre puts oil, and its prospect is very wide.
Rhoifolin is a kind of flavones ingredient being present in the plants such as Rhus succedanea, Exocarpium Citri Grandis, acute turpinia leaf and phoenix-tail fern,
With the biology such as oxidation, antitumor, anti-hypertension, xanthine oxidase inhibitor and heart rate and neuraminidase inhibition
Activity.
Rhoifolin and Japan wax are primarily present in Rhus succedanea, and Rhus succedanea refers mainly to Anacardiaceae, paint category
A Toxicodendron class plant.Paint category more than 20 is planted, and is distributed in east Asia and North America to Central America.There are 15 kinds, master in China
There are lacquer tree T.vernicifluum (Stokes), open country paint (big wood paint) T.succed aneum L, haze tallow tree T.sylvestre
Sieb, is largely distributed in western energy development.China has nearly 15~2,000,000,000 yuan of paint seed resources to be not yet processed utilization every year.Lacquer tree
Fruit be also known as paint seed, in flat tiltedly spherical, size is similar to soya bean, collection in annual 9~October of autumn.3 layers of pericarp point, outer fruit
Epithelium matter shows fish maw white, lark or yellow green, and middle pulp is wax coat, is light yellow or the extractable lacquer tree fat of celadon.It is interior
Core is seed, can squeeze urushoil.Its seed is used for processing lacquer tree fat (also known as haze tallow), because its kind is different, paints paraffin content, the chemistry of seed
Composition and physical characteristic difference, the paint seed paraffin content about 25%~40% of Rhus succedanea (Rhus Succedanea L).
Publication No. CN101319168 Chinese patent discloses a kind of method that Japan wax is prepared from Rhus succedanea seed,
Lacquer tree seed sieve through choosing, washing, drying, shell, selection by winnowing, paint seed pulp raw material, grind, solvent counter current is continuously extracted, extracted
Liquid is separated by filtration, decoloration and deodorization, filtering, thin film evaporation, vacuum concentration, lacquer tree fat ointment, cooling, shaping, granulation, boiled urushi cerotin
Product；Lacquer tree fat ointment is sent into molecular distillation apparatus vacuum outgas in addition and reclaims residual solvent, is gone out through first order molecular separated
The grease such as face cream cream and essential oil, residue distill into secondary molecules, isolate aliphatic acid, fatty alcohol, binary acid and fat
The products such as acid glyceride.
Publication No. CN101205505 Chinese patent discloses a kind of leach extraction method of Japan wax, it is characterised in that
Comprise the following steps：The first step, the pretreatment of raw material：Will after Rhus succedanea seed removal of impurities obtain Rhus succedanea seed pulp, then by its
It is broken into fine powder；Second step, extraction：Carrying out hoirzontally rotating to the fine powder with non-polar solven, continuously extraction obtains leaching liquor, carries
It is 10 DEG C~90 DEG C to take temperature, and charging rate is 50g~2000g/min, and the spray flux of non-polar solven is 1L~30L/min,
Extraction engine speed is 5~300 turns/min, and extraction time is 0.5h~20h；3rd step, insulation is decolourized：The leaching liquor is passed through
60~400 purposes material activated carbon decolorizing obtain activated carbon decolorizing liquid, activated carbon add quality for the leaching liquor weight 1~
25%, bleaching temperature is controlled at 60 DEG C~120 DEG C；4th step, tub and board-like secondary filter：By activated carbon decolorizing liquid warp
Cross tub filter carry out suction filtration obtain filtrate, filter use 200~500 mesh stainless (steel) wires, suction filtration pressure be 0.1~
0.01MPa, filtration temperature is 60 DEG C~90 DEG C, and the filtrate enters back into plate and frame filter press filtering, and filter cloth is that 300~500 mesh are oblique
Line cotton filter cloth, 60 DEG C~90 DEG C of filtration temperature, the filtrate clarified；5th step, is concentrated in vacuo：By the filtrate of the clarification
Progress, which is concentrated in vacuo, obtains Japan wax vacuum concentration thing.
Publication No. CN103833810A Chinese patent discloses a kind of new preparation technology of Rhoifolin, technology warp
Following steps：Dehydrogenation reaction；It is concentrated under reduced pressure；Precipitation, filtering；Concentration, extraction；Decolourize, concentration；Crystallization, centrifugation, crude product is dried,
Recrystallization etc..It is characterized in that the sustainable development of social economy, the consumption of dehydrogenating agent is reduced to the 1~5% of aurantiin amount, choosing
Optimal reaction system has been selected, the utilization rate of aurantiin has been improved, farthest takes full advantage of raw material resources, greatly improve
The yield of Rhoifolin synthetic intermediate, significantly reduces production cost, meets resource-conserving, friendly environment society
Demand for development.
Publication No. CN102633850A Chinese patent discloses a kind of Rhoifolin and its prepares medicinal usage, described
Rhoifolin is obtained using following extracting method：Take acute turpinia leaf or Exocarpium Citri Grandis, plus 5~15 times amount 30%~90% ethanol
Refluxing extraction 1~3 time, each refluxing extraction 1~3 hour, filtration；Merging filtrate, reclaims ethanol, and the aqueous solution passes through macroreticular resin
Post is eluted, and is collected elution fraction, is concentrated under reduced pressure, and is dried, is obtained the total glycosides of mixing of Rhoifolin, through separation, merges Rhoifolin stream
Part, crystallization obtains Rhoifolin sterling, and Rhoifolin can make neuraminidase inhibitor and be used in prevention and treatment influenza, be made
Pharmaceutically acceptable formulation.
Publication No. CN102391337A Chinese patent discloses a kind of side that Rhoifolin is extracted from acute turpinia leaf
Method.Method and step is as follows：Take acute turpinia leaf raw material to crush 40~80 mesh, add in supercritical extraction reactor, be passed through liquid CO 2 and folder
Band agent, in the environment of 20~30MPa of extracting pressure, 40~50 DEG C of temperature, is extracted 2~3 hours, timing parsing extract, is returned
Reagent is received, gained medicinal extract hot water dissolving adds activated carbon decolorizing, and destainer adds polyamide absorption, ethanol water ladder
Degree elution, collects target component and is concentrated under reduced pressure, and concentrate crystallization filters out crystal hot water dissolving recrystallization, is drying to obtain wild paint
Set glycosides.Rhoifolin is produced using this method, energy consumption is low, pollute small, processing step is simple, products obtained therefrom purity is high, be adapted to work
Industry metaplasia is produced.
Publication No. CN102286043A Chinese patent discloses a kind of purification process of Rhoifolin, and its feature exists
In：Using acute turpinia leaf as raw material, crush, plus 55~70% EtOH Sonicate extract 1~3 time, extract solution is concentrated under reduced pressure, concentrate adjust
PH3~4, filtering are saved, filtrate adds polyamide absorption, and ethanol water elution, collection liquid concentration and recovery ethanol, concentrate passes through
Supercentrifuge is filtered, and filtrate is separated by membrane separator, and obtained component is separated using high speed adverse current chromatogram, UV-detector inspection
Survey, collect target component, be dried under reduced pressure and produce Rhoifolin.The method of the present invention is simple to operate, with short production cycle, preparation amount
Greatly, efficiency high, is adapted to high-purity Rhoifolin and prepares.
Fail to carry out the active ingredient of its in extraction process comprehensive development and utilization from presently disclosed documents and materials, it is main right
Lacquer tree fat, which is extracted, in Rhus succedanea studies more, and because extracting method is improper, recovery rate is low to bring very big economic loss.Therefore, open
Rhus succedanea comprehensive study is opened up, its application value is excavated, the forest resourceies for making full use of China's abundant improve secondary product of forestry
Quality, develops the flanker of high added value, promotes China's sustainable economic development, with important and far-reaching meaning.
The content of the invention
The technical solution adopted by the present invention includes：Rhus succedanea after dried is extracted through petroleum ether, filter residue uses diluted acid alcohol again
Solution refluxing extraction, filter, be concentrated to dryness, being dissolved with sour water, open country is made in upper resin adsorption, stepwise elution, condensing crystallizing
Lacquer tree glycosides and Japan wax sterling.
Therefore, the present invention provides a kind of method that Japan wax and Rhoifolin are extracted from Rhus succedanea, and step includes：
(1) crush dry Rhus succedanea fruit to be mixed with petroleum ether to 10~20 mesh, and by Rhus succedanea fruit, 45~65
DEG C 60~90min of refluxing extraction, ceramic membrane filter once, obtains filtrate, then dry obtains Rhus succedanea waxy stone through being concentrated under reduced pressure into；
(2) Rhus succedanea filter residue is mixed with ethanol solution, 45~55 DEG C of 40~60min of refluxing extraction, ceramic membrane mistake
Filter once, obtains extract solution；
(3) extract solution is carried out being concentrated into the 1/4~1/10 of original volume in 50~60 DEG C of decompressions, obtains concentrate I, on
AB-8 macroporous resin adsorption concentrates, and eluted with the solution A of twice to five times of column volume, eluent I is obtained, and will wash
De- liquid I carries out 50~60 DEG C and is concentrated under reduced pressure into the 1/4~1/10 of original volume, obtains concentrate II；
(4) the cold ethanol for adding 4~10 DEG C to Rhus succedanea waxy stone is washed twice, and discards ethanol, is added after ether dissolution, then
Granular activated carbon is added, it adds 5% or so that weight kg is Rhus succedanea waxy stone weight kg, and bleaching temperature is controlled 60~75
DEG C, activated carbon decolorizing time control is in 45~55min, filtering, and dry the smart wax of Rhus succedanea is concentrated under reduced pressure at 50~60 DEG C；
(5) concentrate II is adjusted into pH to 4.5~5.5 or so with 0.01mol/L hydrochloric acid solution, 4 DEG C stand overnight knot
Crystalline substance, filters to obtain crystal, as Rhoifolin.
In one embodiment, petroleum ether described in step (1) is to use boiling range for 30 DEG C~60 DEG C of petroleum ether, plus
Volume L and Rhus succedanea fruit weight the kg ratio for entering petroleum ether are 2~4：1.
In one embodiment, ethanol solution described in step (2), refer to containing 65~75% ethanol,
The ethanol water of 0.0001mol/L hydrochloric acid, volume L and Rhus succedanea fruit weight the kg ratio for adding ethanol solution is 3~6：1.
In one embodiment, solution A described in step (3), refers to containing 55~65% ethanol, 0.001mol/L
The ethanol water of hydrochloric acid.
In one embodiment, the volume L and the thick weight kg ratios of Rhus succedanea that ethanol is added in step (4) are 2~3：
1, the volume L and the thick weight kg ratios of Rhus succedanea for adding ether are 1~2：1.
In one embodiment, filter, refer to using 0.2 μm of pore size described in step (1), (2), (4) and (5)
Ceramic membrane filter once.
Technique effect
1st, the inventive method is simple to operate, substantially increases the yield of Japan wax and Rhoifolin, significantly reduces
The production cost of Japan wax and Rhoifolin, simplifies its production process, moreover it is possible to obtain substantial amounts of oily substance.
2nd, using Rhus succedanea as raw material is extracted, the utilization ratio of Rhus succedanea had both been substantially increased, Rhus succedanea is improved again
Added value.
Tool stops embodiment
Below, the present invention will be further detailed with embodiment, but it is not limited to any of these embodiments
One or similar example.
Embodiment 1
100kg will be weighed below Rhus succedanea fruit crushed after being dried to 10 mesh, (boiling range is 30 DEG C to addition 400L petroleum ether
~60 DEG C) 45~50 DEG C of refluxing extraction 80min of mixing are carried out, ceramic membrane filter once, obtains filtrate, then dry through being concentrated under reduced pressure into
To 45.6kg Rhus succedanea waxy stones.The ethanol of addition 70%, the ethanol water of 0.0001mol/L hydrochloric acid into Rhus succedanea filter residue
300L is mixed, and 45 DEG C or so refluxing extraction 50min, ceramic membrane filter once, obtains extract solution；By 250L extract solutions at 50 DEG C
Decompression progress is concentrated into 30L, obtains concentrate I, upper AB-8 macroporous resin adsorptions concentrate, and with the 60% of four times of column volumes
Ethanol, the ethanol water of 0.001mol/L hydrochloric acid are eluted, and obtain 60L eluents I, and eluent I is carried out into 50 DEG C subtracting
Pressure is concentrated into 10L, obtains concentrate II；6 DEG C of cold ethanol 25L are added to 10kg Rhus succedaneas waxy stone to wash twice, ethanol is discarded, and are added
After 20L ether dissolutions, 0.5kg granular activated carbons are added, bleaching temperature is controlled at 70 DEG C, and activated carbon decolorizing time control exists
55min, filtering is concentrated under reduced pressure into the smart wax of dry 9.24kg Rhus succedaneas at 55 DEG C；With 0.01mol/L hydrochloric acid solution by concentrate
II regulation pH to 5 or so, 4 DEG C stand overnight crystallization, filter to obtain crystal, as 356g Rhoifolins.Carried out using HPLC methods
Rhoifolin is detected, the purity of Rhoifolin sample is 95.54%；Detection Japan wax, Japan wax sample are carried out using GC
Purity be 97.25%.
Embodiment 2
200kg will be weighed below Rhus succedanea fruit crushed after being dried to 10 mesh, (boiling range is 30 DEG C to addition 600L petroleum ether
~60 DEG C) 50~55 DEG C of refluxing extraction 60min of mixing are carried out, ceramic membrane filter once, obtains filtrate, then dry through being concentrated under reduced pressure into
To 93.8kg Rhus succedanea waxy stones.The ethanol of addition 75%, the ethanol water of 0.0001mol/L hydrochloric acid into Rhus succedanea filter residue
800L is mixed, and 50 DEG C of refluxing extraction 50min, ceramic membrane filter once, obtains extract solution；By 700L extract solutions in 50 DEG C of decompressions
Progress is concentrated into 80L, obtains concentrate I, upper AB-8 macroporous resin adsorptions concentrate, and with 60% second of three times column volume
Alcohol, the ethanol water of 0.001mol/L hydrochloric acid are eluted, and obtain 100L eluents I, and eluent I is carried out into 50 DEG C of decompressions
15L is concentrated into, concentrate II is obtained；4 DEG C of cold ethanol 80L are added to 40kg Rhus succedaneas waxy stone to wash twice, ethanol is discarded, and are added
After 40L ether dissolutions, 2kg granular activated carbons are added, bleaching temperature is controlled at 75 DEG C, and activated carbon decolorizing time control exists
45min, filtering is concentrated under reduced pressure into the smart wax of dry 38.55kg Rhus succedaneas at 60 DEG C；With 0.01mol/L hydrochloric acid solution by concentrate
II regulation pH to 5 or so, 4 DEG C stand overnight crystallization, filter to obtain crystal, as 812g Rhoifolins.Carried out using HPLC methods
Rhoifolin is detected, the purity of Rhoifolin sample is 95.66%；Detection Japan wax, Japan wax sample are carried out using GC
Purity be 97.21%.
Claims (5)
1. a kind of method that Japan wax and Rhoifolin are extracted from Rhus succedanea, step includes：
(1) crush dry Rhus succedanea fruit to be mixed with petroleum ether to 10~20 mesh, and by Rhus succedanea fruit, 45~65 DEG C are returned
Stream extracts 60~90min, and ceramic membrane filter once, obtains filtrate, then dry obtains Rhus succedanea waxy stone through being concentrated under reduced pressure into；
(2) Rhus succedanea filter residue is mixed with ethanol solution, 45~55 DEG C of 40~60min of refluxing extraction, ceramic membrane filter one
It is secondary, obtain extract solution；
(3) extract solution is carried out being concentrated into the 1/4~1/10 of original volume in 50~60 DEG C of decompressions, obtains concentrate I, upper AB-8
Macroporous resin adsorption concentrate, and being eluted with the solution A of twice to five times of column volume, obtains eluent I, and by eluent
I, which carries out 50~60 DEG C, is concentrated under reduced pressure into the 1/4~1/10 of original volume, obtains concentrate II；
(4) the cold ethanol for adding 4~10 DEG C to Rhus succedanea waxy stone is washed twice, and discards ethanol, is added after ether dissolution, is added
Granular activated carbon, it adds 5% or so that weight kg is Rhus succedanea waxy stone weight kg, and bleaching temperature is controlled at 60~75 DEG C, living
Property carbon decoloring time control in 45~55min, filtering is concentrated under reduced pressure into dry the smart wax of Rhus succedanea at 50~60 DEG C；
(5) concentrate II is adjusted into pH to 4.5~5.5 or so with 0.01mol/L hydrochloric acid solution, 4 DEG C stand overnight crystallization, mistake
Filter to obtain crystal, as Rhoifolin.
2. method according to claim 1, petroleum ether described in step (1) is to use boiling range for 30 DEG C~60 DEG C of petroleum ether,
Volume L and Rhus succedanea fruit weight the kg ratio for adding petroleum ether are 2~4：1.
3. method according to claim 1, ethanol solution described in step (2), refer to containing 65~75% ethanol,
The ethanol water of 0.0001mol/L hydrochloric acid, volume L and Rhus succedanea fruit weight the kg ratio for adding ethanol solution is 3~6：1.
4. method according to claim 1, solution A described in step (3), refers to containing 55~65% ethanol, 0.001mol/
The ethanol water of L hydrochloric acid.
5. volume L and the thick weight kg ratios of Rhus succedanea that ethanol is added in method according to claim 1, step (4) are 2~3：
1, the volume L and the thick weight kg ratios of Rhus succedanea for adding ether are 1~2：1.
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| CN201710580765.0A CN107312049A (en) | 2017-07-17 | 2017-07-17 | A kind of method that Rhoifolin and Japan wax are extracted from Rhus succedanea |
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| CN201710580765.0A CN107312049A (en) | 2017-07-17 | 2017-07-17 | A kind of method that Rhoifolin and Japan wax are extracted from Rhus succedanea |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110538712A (en) * | 2019-09-16 | 2019-12-06 | 河南省予北粮油机械有限公司 | Deparaffinization production method of lacquer seeds |
| CN112998264A (en) * | 2021-03-22 | 2021-06-22 | 中南林业科技大学 | Organic gel and preparation method and application thereof |
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| CN101906122A (en) * | 2010-08-16 | 2010-12-08 | 江西山香药业有限公司 | Method for extracting rhoifolin and prepared medicament application thereof |
| CN102286043A (en) * | 2011-10-10 | 2011-12-21 | 南京泽朗医药科技有限公司 | Purification method of rhoifolin |
| CN106349308A (en) * | 2016-08-02 | 2017-01-25 | 重庆工商大学 | Method for extracting apigenin-7-O-neohesperidoside from paeonia suffruticosa andrews and application of apigenin-7-O-neohesperidoside |
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| CN102286043A (en) * | 2011-10-10 | 2011-12-21 | 南京泽朗医药科技有限公司 | Purification method of rhoifolin |
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| 董艳鹤: "漆蜡的物化特征及精制加工工艺研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110538712A (en) * | 2019-09-16 | 2019-12-06 | 河南省予北粮油机械有限公司 | Deparaffinization production method of lacquer seeds |
| CN112998264A (en) * | 2021-03-22 | 2021-06-22 | 中南林业科技大学 | Organic gel and preparation method and application thereof |
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Application publication date: 20171103 |