CN110642708A - Method for separating and extracting caproic acid, heptanoic acid and octanoic acid from livestock and poultry manure anaerobic acidification liquid - Google Patents
Method for separating and extracting caproic acid, heptanoic acid and octanoic acid from livestock and poultry manure anaerobic acidification liquid Download PDFInfo
- Publication number
- CN110642708A CN110642708A CN201911051661.6A CN201911051661A CN110642708A CN 110642708 A CN110642708 A CN 110642708A CN 201911051661 A CN201911051661 A CN 201911051661A CN 110642708 A CN110642708 A CN 110642708A
- Authority
- CN
- China
- Prior art keywords
- acid
- controlling
- extracting
- livestock
- tower
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
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
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F3/00—Biological treatment of water, waste water, or sewage
- C02F3/28—Anaerobic digestion processes
-
- 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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Water Supply & Treatment (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Biodiversity & Conservation Biology (AREA)
- Hydrology & Water Resources (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of organic acid separation methods, and particularly relates to a method for separating and extracting caproic acid, heptanoic acid and caprylic acid from anaerobic acidification liquid of livestock and poultry manure, which comprises the following steps: A. solid-liquid separation; B. extracting with organic acid; C. recovering the extractant; D. and (4) multistage vacuum rectification. The method for separating and extracting the caproic acid, the heptanoic acid and the octanoic acid from the anaerobic acidification liquid of the livestock and poultry manure adopts solid-liquid separation to remove large-particle suspended matters, so that the extraction efficiency can be improved; the mixed acid liquid after solid-liquid separation is directly extracted without acid regulation treatment, and the extraction rate is more than 95%; the extraction agent recovery process is carried out by normal-pressure low-temperature distillation, so that volatilization of low-boiling-point short-chain organic acid is avoided, and the temperatures of a tower kettle and a tower top are jointly controlled, so that the extraction agent with the concentration of more than 92 percent is efficiently recovered; multi-stage vacuum rectification to respectively obtain high-purity caproic acid, heptanoic acid and caprylic acid; realizes high-value utilization of the livestock and poultry manure anaerobic acidification liquid rich in medium-chain fatty acid, and is beneficial to promoting the development and application of the medium-chain fatty acid biosynthesis process.
Description
Technical Field
The invention belongs to the field of organic acid separation methods, and particularly relates to a method for separating and extracting caproic acid, heptanoic acid and caprylic acid from anaerobic acidification liquid of livestock and poultry manure.
Background
The anaerobic digestion treatment process of the livestock and poultry feces can generate intermediate metabolites such as acetic acid, propionic acid, butyric acid, valeric acid and the like, and the short-chain fatty acids (C2-C5) can generate a carbon chain elongation reaction (a reverse beta oxidation process) under the driving of an external electron donor ethanol or lactic acid, so that part of the short-chain fatty acids can be converted into medium-chain fatty acids with high added values, and further a mixed organic acid solution containing the short-chain fatty acids and the medium-chain fatty acids is obtained (Liang S, Wan C. Carboxylic acid production from branched chain' S solvent vitamin mixed culture. [ J ]. Bioresource Technology,2015,182: 179-183.). Medium chain fatty acids have the following advantages over short chain fatty acids: (1) the carbon chain is long, the C/O ratio is high, and the heat value is high; (2) the solubility of the water phase is low, and the separation is easy; (3) can be used for synthesizing biological fuel and chemicals, such as biological diesel oil and synthetic resin; (4) used as feed additive, etc.
However, the unseparated mixed organic acid solution is difficult to be directly applied industrially, so in order to avoid resource waste and further improve the practical application value of the mixed organic acid solution, the separation and extraction of medium-chain fatty acids such as caproic acid, heptanoic acid and caprylic acid with higher added values in the livestock and poultry manure anaerobic fermentation liquor are required. In recent years, related scholars have preliminarily explored separation and extraction of medium-chain fatty acids in anaerobic fermentation liquor of simple substrates, for example, CN 107382708A discloses a method for extracting caproic acid from biological fermentation liquor, and the technical scheme of the method comprises sterilization, acid regulation, organic extraction, emulsion breaking and low-temperature reduced pressure distillation; kucek et al (Kucek L A, Spirito C M, antigen L.T.high n-phosphate production and peptides from di-lute ethanol and acetate: chain electron from products formation [ J ]. Energy & Environmental Science,2016,9(11):3482-3494.) achieved high efficiency extraction of medium chain fatty acids during the organic acid carbon chain extension reaction, followed by alkali recovery (pH 9.0) to obtain high concentration mixed medium chain fatty acid solution, which only achieved high efficiency separation of medium chain fatty acids from short chain fatty acids, but did not achieve organic separation of medium chain fatty acids.
The prior research or patent mostly discusses the extraction process of single medium-chain fatty acid caproic acid, and the extraction process of respectively obtaining high-purity caproic acid, heptanoic acid and caprylic acid from mixed fatty acid has not been reported.
Disclosure of Invention
The invention aims at the technical problem and provides a method for separating and extracting caproic acid, heptanoic acid and octanoic acid from anaerobic acidification liquid of livestock and poultry manure, which comprises the following steps:
A. solid-liquid separation: carrying out solid-liquid separation on the livestock and poultry manure anaerobic acidification liquid containing the medium-chain fatty acid, removing suspended matters and leaving supernatant;
B. organic acid extraction: adding a hydrophobic organic solvent into the supernatant, and extracting organic acid from the aqueous phase to an organic phase to obtain an organic phase mixed solution;
C. recovering the extractant: distilling the organic phase mixed solution at normal pressure and low temperature, recovering the extractant, and leaving the mixed organic acid solution;
D. and (3) multistage vacuum rectification: the multistage vacuum rectification is carried out on the mixed organic acid solution, and the specific steps are as follows:
d1, controlling the pressure in the rectifying tower to be 10KPa, controlling the temperature at the top of the rectifying tower to be 75-80 ℃, and rectifying to obtain short-chain volatile fatty acid;
d2, controlling the pressure in the rectifying tower to be 5KPa, controlling the temperature at the top of the tower to be 120-130 ℃, and rectifying to obtain caproic acid;
d3, controlling the pressure in the rectifying tower to be 2KPa, controlling the temperature at the top of the tower to be 120-130 ℃, and rectifying to obtain heptanoic acid;
d4, controlling the pressure in the rectifying tower to be 2KPa, controlling the temperature at the top of the tower to be 130-140 ℃, and rectifying to obtain the octanoic acid.
And B, performing solid-liquid separation in the step A, namely centrifuging the mixed organic acid-containing biological fermentation broth for 10-15 min at 4500rpm, and then removing large-particle suspended matters through a stainless steel filter with the pore size of 200 mu m.
Wherein, the hydrophobic organic solvent in the step B is methyl tert-butyl ether.
And B, extracting the organic acid in the step B, and treating the extract according to the following supernatant: extracting with the mass ratio of methyl tert-butyl ether (3-5) to 1.
And C, carrying out normal-pressure low-temperature distillation in the step C, controlling the temperatures of the distillation tower kettle and the tower top to be 60-80 ℃ and 50-55 ℃ respectively, and stopping distillation when the temperature of the tower top is reduced to be below 50 ℃.
Wherein, the livestock manure is preferably pig manure.
The invention has the beneficial effects that:
the invention can respectively obtain high-purity caproic acid, enanthic acid and caprylic acid through solid-liquid separation, organic acid extraction, extractant recovery and vacuum rectification treatment, and simultaneously realizes the recycling of short-chain organic acid. The system has the following advantages and effects:
(1) the extraction efficiency can be improved by adopting solid-liquid separation to remove large-particle suspended matters.
(2) The mixed acid liquid after solid-liquid separation is directly subjected to multistage extraction without acid regulation treatment, so that the acid regulation operation procedure is reduced, and the organic acid extraction rate is over 95 percent;
(3) the process of recovering the extractant by normal-pressure low-temperature distillation is adopted, the volatilization of the low-boiling-point short-chain organic acid is avoided, the temperatures of the tower kettle and the tower top are jointly controlled, the high-efficiency recovery of the extractant of more than 92 percent is realized, and the cost is reduced.
(4) Multi-stage vacuum rectification to respectively obtain high-purity caproic acid, heptanoic acid and caprylic acid; realizes the high-value utilization of the mixed organic acid solution, and is beneficial to promoting the development and application of the biosynthesis process of the medium-chain fatty acid.
Drawings
FIG. 1 is a process flow chart of a method for separating and extracting hexanoic acid, heptanoic acid and octanoic acid from anaerobic acidification liquid of livestock and poultry manure in an embodiment.
In the figure, SCFAs are short chain fatty acids and MCCAs are medium chain fatty acids.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The invention discloses a method for separating and extracting caproic acid, heptanoic acid and caprylic acid from anaerobic acidification liquid of livestock and poultry manure. The invention will now be described with reference to the process flow diagram (see FIG. 1) and the following examples, which are provided to illustrate the invention but are not intended to limit the scope of the invention. The separation method comprises 4 parts of anaerobic fermentation liquor solid-liquid separation, organic solvent extraction, extractant recovery, multistage vacuum rectification and the like. The method comprises the following steps: 1) removing large-particle suspended matters in the fermentation liquor through solid-liquid separation, and carrying out next treatment on the supernatant; 2) adding a hydrophobic organic solvent into the supernatant after solid-liquid separation, and extracting organic acid from the water phase to an organic phase; 3) the acid-containing organic phase is distilled at normal pressure and low temperature, so that the organic acid is efficiently separated from the extracting agent, and the extracting agent is recovered to realize cyclic utilization; 4) and performing multistage vacuum rectification on the extracted mixed organic acid solution to sequentially obtain mixed short-chain fatty acid and high-purity caproic acid, heptanoic acid and caprylic acid.
Example 1
The embodiment comprises the following steps:
A. solid-liquid separation: centrifuging the livestock and poultry manure anaerobic acidification liquid containing medium-chain fatty acids for 10-15 min at 4500rpm, and then removing large-particle suspended matters through a stainless steel filter with the pore diameter of 200 mu m to leave supernatant.
B. Organic acid extraction: hydrophobic methyl tert-butyl ether was used as extractant, according to the supernatant: the mass ratio of the methyl tert-butyl ether is 2:1, 5:1 and 10:1, the mixture is stirred by magnetic force for about 10min to be fully mixed and then poured into a separating funnel for separating liquid, the lower layer is a water phase, and the upper layer is an organic phase; the aqueous phase was extracted 3 to 4 times repeatedly, and the organic phases obtained by each treatment were mixed to form an organic phase mixed solution. The extraction rates of the organic acid treated by the methyl tert-butyl ether with the mass ratios of 2:1, 5:1 and 10:1 are respectively 97.1%, 96.8% and 92.7%, wherein the extraction rates of 2:1 and 5:1 are not obviously different, and the extraction rate of the organic acid is reduced by 4.2% from 10:1 to 5: 1.
C. Recovering the extractant: distilling an organic phase obtained by extraction of methyl tert-butyl ether with a mass ratio of 5:1 under normal pressure, controlling the temperatures of a distillation tower kettle and a tower top to be 60-80 ℃ and 50-55 ℃ respectively, and stopping distillation when the temperature of the tower top is reduced to below 50 ℃. The distilled methyl tert-butyl ether was recovered by condensation with an extractant recovery of 92%.
D. And (3) rectification: the reduced pressure rectification is carried out by adopting a packed column with a reflux ratio, and is divided into two treatments, and the specific parameter setting and the recovery rate are as follows:
firstly, controlling the pressure in a rectifying tower to be 10KPa, the temperature at the top of the rectifying tower to be 70-80 ℃, and the recovery rate of short-chain fatty acid to be 95%; controlling the pressure in the rectifying tower to be 5KPa, the temperature at the top of the tower to be 120 ℃, and the recovery rate of the caproic acid to be 90 percent; the pressure of the rectifying tower is controlled to be 2KPa, the temperature of the top of the rectifying tower is controlled to be 120-130 ℃ and 130-140 ℃, and the recovery rates of heptanoic acid (C7) and octanoic acid (C8) are 85% and 90% respectively.
Secondly, controlling the pressure in the rectifying tower to be 10KPa, the temperature at the top of the rectifying tower to be 70-80 ℃, and the recovery rate of the short-chain fatty acid to be 95%; keeping the pressure in the rectifying tower at 10KPa, the temperature at the top of the tower at 120 ℃, and the recovery rate of the caproic acid only at 80%; the pressure of the rectifying tower is controlled to be 5KPa, the temperature of the top of the rectifying tower is controlled to be 120-130 ℃ and 130-140 ℃, and the recovery rates of heptanoic acid (C7) and octanoic acid (C8) are both lower than 70%.
The above description is only a preferred embodiment of the present invention, and it should be understood that a person skilled in the art may make several modifications and improvements without departing from the technical principle of the present invention, and the protection scope of the present invention should be considered.
Claims (1)
1. A method for separating and extracting caproic acid, heptanoic acid and octanoic acid from anaerobic acidification liquid of livestock and poultry manure is characterized by comprising the following steps:
A. solid-liquid separation: carrying out solid-liquid separation on the livestock and poultry manure anaerobic acidification liquid containing the medium-chain fatty acid, removing suspended matters and leaving supernatant;
B. organic acid extraction: adding a hydrophobic organic solvent into the supernatant, and extracting organic acid from the aqueous phase to an organic phase to obtain an organic phase mixed solution;
C. recovering the extractant: distilling the organic phase mixed solution at normal pressure and low temperature, recovering the extractant, and leaving the mixed organic acid solution;
D. and (3) multistage vacuum rectification: the multistage vacuum rectification is carried out on the mixed organic acid solution, and the specific steps are as follows:
d1, controlling the pressure in the rectifying tower to be 10KPa, controlling the temperature at the top of the rectifying tower to be 75-80 ℃, and rectifying to obtain short-chain volatile fatty acid;
d2, controlling the pressure in the rectifying tower to be 5KPa, controlling the temperature at the top of the tower to be 120-130 ℃, and rectifying to obtain caproic acid;
d3, controlling the pressure in the rectifying tower to be 2KPa, controlling the temperature at the top of the tower to be 120-130 ℃, and rectifying to obtain heptanoic acid;
d4, controlling the pressure in the rectifying tower to be 2KPa, controlling the temperature at the top of the tower to be 130-140 ℃, and rectifying to obtain the octanoic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911051661.6A CN110642708B (en) | 2019-10-31 | 2019-10-31 | Method for separating and extracting caproic acid, heptanoic acid and octanoic acid from livestock and poultry manure anaerobic acidification liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911051661.6A CN110642708B (en) | 2019-10-31 | 2019-10-31 | Method for separating and extracting caproic acid, heptanoic acid and octanoic acid from livestock and poultry manure anaerobic acidification liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110642708A true CN110642708A (en) | 2020-01-03 |
| CN110642708B CN110642708B (en) | 2020-07-07 |
Family
ID=68995298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911051661.6A Active CN110642708B (en) | 2019-10-31 | 2019-10-31 | Method for separating and extracting caproic acid, heptanoic acid and octanoic acid from livestock and poultry manure anaerobic acidification liquid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110642708B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394894A (en) * | 2022-01-27 | 2022-04-26 | 上海化工研究院有限公司 | Method and device for extracting high-purity heptanoic acid from side line by vacuum batch rectification |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07291890A (en) * | 1994-04-28 | 1995-11-07 | Daicel Chem Ind Ltd | Method for separating aliphatic carboxylic acid by extraction |
| CN101391908A (en) * | 2008-09-16 | 2009-03-25 | 通州市专用肥料厂 | Method for manufacturing amino-yellow humic acid by oxidation of faeces |
| CN102816332A (en) * | 2012-08-25 | 2012-12-12 | 福建超大集团有限公司 | Harmless extraction process for poultry manure prepared agricultural biochemical fulvic acid |
| CN106370500A (en) * | 2016-08-26 | 2017-02-01 | 中国农业科学院农产品加工研究所 | Extraction separation method of fat-soluble metabolite in faeces |
| CN107363076A (en) * | 2017-08-10 | 2017-11-21 | 中国科学院成都生物研究所 | A kind of reclaiming organic waste processing method |
| CN107382708A (en) * | 2017-08-10 | 2017-11-24 | 中国科学院成都生物研究所 | A kind of extracting method of medium chain fatty acid caproic acid |
| WO2019005628A1 (en) * | 2017-06-28 | 2019-01-03 | Vitaworks Ip, Llc | Process for the separation of long chain amino acids and dibasic acids |
| CN109913509A (en) * | 2018-04-28 | 2019-06-21 | 湖北大学 | A kind of fermentation medium and zymotechnique of efficient production short-chain branch fatty acid |
-
2019
- 2019-10-31 CN CN201911051661.6A patent/CN110642708B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07291890A (en) * | 1994-04-28 | 1995-11-07 | Daicel Chem Ind Ltd | Method for separating aliphatic carboxylic acid by extraction |
| CN101391908A (en) * | 2008-09-16 | 2009-03-25 | 通州市专用肥料厂 | Method for manufacturing amino-yellow humic acid by oxidation of faeces |
| CN102816332A (en) * | 2012-08-25 | 2012-12-12 | 福建超大集团有限公司 | Harmless extraction process for poultry manure prepared agricultural biochemical fulvic acid |
| CN106370500A (en) * | 2016-08-26 | 2017-02-01 | 中国农业科学院农产品加工研究所 | Extraction separation method of fat-soluble metabolite in faeces |
| WO2019005628A1 (en) * | 2017-06-28 | 2019-01-03 | Vitaworks Ip, Llc | Process for the separation of long chain amino acids and dibasic acids |
| CN107363076A (en) * | 2017-08-10 | 2017-11-21 | 中国科学院成都生物研究所 | A kind of reclaiming organic waste processing method |
| CN107382708A (en) * | 2017-08-10 | 2017-11-24 | 中国科学院成都生物研究所 | A kind of extracting method of medium chain fatty acid caproic acid |
| CN109913509A (en) * | 2018-04-28 | 2019-06-21 | 湖北大学 | A kind of fermentation medium and zymotechnique of efficient production short-chain branch fatty acid |
Non-Patent Citations (3)
| Title |
|---|
| ALBERT TANGERMAN等: "Quantitative determination of C2-C8 volatile fatty acids in human serum by vacuum distillation and gas chromatography", 《CLINICA CHIMICA ACTA》 * |
| 夏纪鼎等: "合成脂肪酸 第三讲 合成脂肪酸的精制", 《日用化学工业》 * |
| 王福海等: "合成C5-9酸单离技术的研究", 《无锡轻工业学院学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394894A (en) * | 2022-01-27 | 2022-04-26 | 上海化工研究院有限公司 | Method and device for extracting high-purity heptanoic acid from side line by vacuum batch rectification |
| CN114394894B (en) * | 2022-01-27 | 2023-11-28 | 上海化工研究院有限公司 | Method and device for extracting Gao Chungeng acid from side line of vacuum batch distillation |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110642708B (en) | 2020-07-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6288275B1 (en) | Separation and purification of carboxylic acids from fermentation broths | |
| CN102746947A (en) | Method for separating and purifying DHA (docosahexaenoic acid) and saturated fatty acid from schizochytrium limacinum oil | |
| CN100537592C (en) | Method of coproducting phytosterol, biological diesel oil and vitamin E | |
| CN109294893B (en) | Resource utilization system and method for white spirit brewing byproduct yellow water | |
| JP2010539911A5 (en) | ||
| CN107628963B (en) | Vitamin B5Method for preparing crude product | |
| CN104651422A (en) | Method of extracting DHA and EPA in type of triglyceride from deep-sea fish | |
| CN103804337A (en) | Novel technology for extracting vitamin E and squalene by employing multi-stage counter-current liquid-liquid extraction method | |
| CN110642708B (en) | Method for separating and extracting caproic acid, heptanoic acid and octanoic acid from livestock and poultry manure anaerobic acidification liquid | |
| CN105132189B (en) | A kind of fine separation method of C18 series and C20~C22 series fatty acid methyl esters | |
| CN102320953B (en) | Method for preparing natural alpha-linolenic acid from crude oil of idesia polycarpa var.vestita diels | |
| CN102887821B (en) | A kind of method of extracting and separating marine microalgae broth extraction DHA | |
| CN114436731A (en) | Preparation method of cyclopropane derivative | |
| CN104017042B (en) | A kind of separation purification method of 7-DHC | |
| CN112159300A (en) | Method for extracting squalene from plant deodorized distillate | |
| US20190276861A1 (en) | Enzymatic method for preparing glyceryl butyrate | |
| CN102942995B (en) | Method for separating and modifying plant oil | |
| CN102219669B (en) | Method for extracting purslane linolenic acid with supercritical CO2 fluid | |
| CN104312731A (en) | Method for extracting torreya grandis aril volatile oil | |
| CN107382708B (en) | Method for extracting medium-chain fatty acid caproic acid | |
| CN1111168C (en) | Supercritical fluid extraction method of high-purity sterol | |
| CN105755059B (en) | Method for improving synthetic concentration of carbon chain biological extension product | |
| CN106831287B (en) | System and method for preparing bio-based butadiene | |
| CN104232289A (en) | Equipment and method for increasing yield of unsaturated fatty acid of rice oil | |
| CN106977394A (en) | A kind of technique of the low colourity arachidonic acid oil of rapid extraction |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |