CN1183238C - Method of manufacturing vegetable oil methyl aliphate using biological enzyme method - Google Patents
Method of manufacturing vegetable oil methyl aliphate using biological enzyme method Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 27
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 25
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 title abstract description 8
- 239000008158 vegetable oil Substances 0.000 title abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 28
- 108090001060 Lipase Proteins 0.000 claims abstract description 21
- 239000004367 Lipase Substances 0.000 claims abstract description 21
- 102000004882 Lipase Human genes 0.000 claims abstract description 21
- 235000019421 lipase Nutrition 0.000 claims abstract description 21
- 239000000047 product Substances 0.000 claims abstract description 8
- 235000013311 vegetables Nutrition 0.000 claims description 58
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 43
- 229930195729 fatty acid Natural products 0.000 claims description 43
- 239000000194 fatty acid Substances 0.000 claims description 43
- 239000003921 oil Substances 0.000 claims description 40
- 235000019198 oils Nutrition 0.000 claims description 40
- -1 fatty acids methyl esters Chemical class 0.000 claims description 38
- 108010084311 Novozyme 435 Proteins 0.000 claims description 9
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 235000019483 Peanut oil Nutrition 0.000 claims description 7
- 239000000312 peanut oil Substances 0.000 claims description 7
- 210000000582 semen Anatomy 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 claims description 6
- 235000017647 Brassica oleracea var italica Nutrition 0.000 claims description 6
- 240000003259 Brassica oleracea var. botrytis Species 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 5
- 235000012343 cottonseed oil Nutrition 0.000 claims description 5
- 239000002385 cottonseed oil Substances 0.000 claims description 5
- 235000019197 fats Nutrition 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 235000019482 Palm oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 239000002540 palm oil Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 108010048733 Lipozyme Proteins 0.000 claims description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 2
- 239000008159 sesame oil Substances 0.000 claims description 2
- 235000011803 sesame oil Nutrition 0.000 claims description 2
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 claims 1
- 239000004519 grease Substances 0.000 claims 1
- 230000010355 oscillation Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003054 catalyst Substances 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000003344 environmental pollutant Substances 0.000 abstract description 2
- 231100000719 pollutant Toxicity 0.000 abstract description 2
- 239000006184 cosolvent Substances 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003925 fat Substances 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 239000002283 diesel fuel Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001661345 Moesziomyces antarcticus Species 0.000 description 1
- 241000235403 Rhizomucor miehei Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000012809 cooling fluid Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
The present invention relates to a method for manufacturing fatty acid methyl ester of vegetable oil with a biological enzyme method. Natural vegetable oil and methanol are used as raw materials by the method. Cosolvent is added for reaction under the action of an immobilized lipase catalyst so as to prepare the fatty acid methyl ester of vegetable oil. A conversion rate reaches above 95%. The method for manufacturing fatty acid methyl ester of vegetable oil of the present invention has the advantages of mild reaction conditions, little alcohol consumption, simple technology, capacity of directly obtaining the fatty acid methyl ester of vegetable oil and byproduct glycerol, no need of refining processing, energy saving, no pollutant emission, high conversion rate, high product quality, etc.
Description
Technical field
The present invention relates to a kind ofly prepare the novel method of fatty acid methyl ester, particularly relate to a kind of novel method of making the vegetable fatty acids methyl esters with biological enzyme with biological enzyme.
Background technology
Vegetables oil or natural fats and oils fatty acid methyl esters are the important intermediate during oiling is learned, and very wide application field is arranged.It is a basic raw material of producing kinds of surface promoting agents such as non-ionic type, anionic, senior perfumed soap.The vegetable fatty acids methyl esters still is a kind of comparatively ideal leather fat simultaneously, particularly prepares one of important intermediate raw material of combined fat liquor.High carbon number fatty acid methyl ester also can be used as senior lubricant and cuts the oil that disappears, cooling fluid, rolls the additive that grinds oil and change hole wet goods mechanical workout oil product.In order to protect the limited petroleum resources of environment and saving that the exploitation of alternate energy source is seemed more and more important, the vegetable fatty acids methyl esters has also caused attention widely as the research that substitutes of diesel oil in recent years.The vegetable fatty acids methyl esters also has the cetane value higher than diesel oil, good lubricity and environmental-protecting performance except that having the performance similar to diesel oil, Given this, the whole world is just growing to the demand of vegetable fatty acids methyl esters.It is a lot of that the production of relevant vegetable fatty acids methyl esters prepares patent, described in the United States Patent (USP) 2271619 natural fats and oils and low mass molecule alcohol such as methyl alcohol and ℃ reaction of basic catalyst Hybrid Heating to 80, deglycerizin from reaction mixture, steam behind the excessive alcohol the method for fatty acid methyl ester.United States Patent (USP) 465206, Japan special permission communique (B) is clear and 60-25478 and Chinese patent application numbers 89107686.7, has all reported in the CN1073474 prospectus and has adopted an acidic catalyst to carry out adopting basic catalyst to carry out the method that alcoholysis prepares the vegetable fatty acids methyl esters after the pre-esterification.
The method of above-mentioned use chemical catalyst exists complex process, alcohol must be excessive, and subsequent technique must have corresponding pure retrieving arrangement, energy consumption height; Because adopt homogeneous catalyst last handling process complexity, homogeneous catalyst and reacted glycerine are removed and can not reuse, need neutralization, washing, can bring a large amount of trade effluents, cause environmental pollution; Moreover the more economic factors of alcoholysis technology is the purification of by-product glycerin, and when a large amount of inorganic materials must be removed, this purification was more difficult.
Summary of the invention
The objective of the invention is to overcome above-mentioned defective, be engaged in the development research and the suitability for industrialized production practice of vegetable fatty acids methyl esters for many years through the contriver, it is simple that exploitation proposes a kind of technology, the reaction conditions gentleness, need not refinement treatment, non-pollution discharge, high conversion, high-quality biological enzyme are made the novel method of vegetable fatty acids methyl esters.
The method that biological enzyme provided by the invention is made the vegetable fatty acids methyl esters comprises:
---vegetables oil, methyl alcohol, solubility promoter vegetable fatty acids methyl esters are dropped into closure and be equipped with in the container of stirring, after stirring, add the biological enzyme agent again, screw container cover, and the container that reaction mass will be housed is put into vibrator and is vibrated, the concussion frequency is 100-200rpm, under 30-60 ℃ of temperature, reacted 20-48 hour, wherein in 100 weight part vegetables oil, solubility promoter vegetable fatty acids methyl esters is the 50-100 weight part, biological enzyme agent 4-8 weight part, the mol ratio of methyl alcohol and vegetables oil is 1: 1.
---by filtering the biological enzyme agent is shifted out from reaction product.
---reactant placed leaves standstill more than 12 hours, treat deglycerizin layer after the layering, product vegetable fatty acids formicester.
Make according to biological enzyme provided by the invention in the novel method of vegetable fatty acids methyl esters, described vegetables oil comprises rapeseed oil, Oleum Gossypii semen, soya-bean oil, peanut oil, plam oil, Oleum Cocois.Siritch, Oleum Helianthi, sesame oil, Semen Maydis oil, broccoli oil or castor-oil plant wet goods are preferably rapeseed oil, Oleum Gossypii semen, soya-bean oil, peanut oil, broccoli oil, plam oil or Oleum Cocois.Main component is a tri-glyceride in described vegetables oil, wherein fatty acid part comprises components such as unsaturated fatty acids and saturated fatty acid, unsaturated fatty acids and saturated fatty acid content and degree of unsaturation and to some extent difference different along with vegetable oil kind, do not have essential difference but the present invention is made the vegetable fatty acids methyl esters with biological enzyme, can both realize purpose of the present invention.Vegetable fatty acids methyl esters of the present invention is exactly the general designation of the vegetable fatty acids methyl esters that made by above-mentioned vegetables oil, and rapeseed oil fatty acid methyl esters, cottonseed oil fatty acid methyl esters, methyl soyate, palm oil fatty acid methyl esters, peanut oil fatty acid methyl esters, coconut oil fatty acid methyl ester or broccoli fatty acid oil methyl esters etc. are arranged respectively.
Described solubility promoter vegetable fatty acids methyl esters is identical with above-mentioned vegetable fatty acids methyl esters, comprises rapeseed oil fatty acid methyl esters, cottonseed oil fatty acid methyl esters, methyl soyate, palm oil fatty acid methyl esters, peanut oil fatty acid methyl esters, coconut oil fatty acid methyl ester or broccoli fatty acid oil methyl esters etc.Make in the vegetable fatty acids methyl esters method at biological enzyme, the vegetables oil of preferred used solubility promoter vegetable fatty acids methyl esters and material plant oil phase are together, the various vegetable fatty acids methyl esters that are beneficial to make need not separate the direct pure vegetable fatty acids methyl esters that gets, otherwise get the mixed vegetable oil fatty acid methyl ester.The mutual solubility of these solubility promoter vegetable fatty acids methyl esters and methyl alcohol is good, simultaneously might as well with the vegetables oil mutual solubility, putting into the vegetable fatty acids methyl esters in reaction mixture just can make vegetables oil and methanol mixed even, accelerate response speed, also avoided methyl alcohol separately the toxic action of lipase to be caused the lipase inactivation simultaneously.The consumption of solubility promoter vegetable fatty acids methyl esters is counted the 50-100 weight part with 100 weight part vegetables oil.
Described methyl alcohol must be purity greater than more than 99.5%, for example industrial grade benzenemethanol or chemical reagent-grade methyl alcohol, analytical pure methyl alcohol etc., purity is all more than 99.5%, all applicable in the inventive method, methanol purity is high more favourable more to the biological enzyme agent.Methanol usage is and plant wet goods mole that both vegetables oil methyl alcohol mol ratio was 1: 1.
Described biological enzyme is meant lipase, NOVOZYM435 immobilized lipase (CANDIDA ANTARCTICA for example, NOVO NORDISK company sell goods), LIPOZYME RM IM immobilized lipase (RHIZOMUCOR MIEHEI, NOVONORDISK company sell goods), LIPASE-RH immobilized lipase (RHIZOPUSDELEMAR, TANABE SEIYAKU company limited sell goods), be preferably the NOVOZYM435 immobilized lipase, its consumption is the 4-8 weight part with respect to 100 weight part vegetables oil.
The novel method characteristics that biological enzyme provided by the invention is made the vegetable fatty acids methyl esters adopt biological enzyme one immobilized lipase to do to make vegetable fatty acids by the reaction of crude vegetal and methyl alcohol under the condition of catalyzer and importing solubility promoter vegetable fatty acids methyl esters.This method has the reaction conditions gentleness, pure consumption is little, and technology is simple, can directly obtain fatty acid methyl ester and by-product glycerin, need not refinement treatment, and save energy, advantages such as non-pollutant discharge, reaction conversion ratio height, the product quality height of conversion.
Embodiment
The present invention further specifies the present invention with the following examples, but protection scope of the present invention is not limited to embodiment.
Embodiment 1
After in the Erlenmeyer flask of 50ml, adding Oleum Gossypii semen 11.5 grams, methyl alcohol 0.4 gram, the abundant stirring of cottonseed oil fatty acid methyl esters 6.0 grams, add NOVOZYM435 immobilized lipase 0.5 gram, with tapered bottleneck sealing, and put it in the vibrator, open vibrator, shake under the frequency of 150RPM, be warming up to 30 ℃, reaction was carried out about 24 hours.After reaction finishes, the NOVOZYM435 immobilized lipase is shifted out from reaction product, reaction product is placed left standstill 13 hours then, treat deglycerizin layer after the layering by filtering, product cottonseed oil fatty acid methyl esters, the transformation efficiency of reaction is 97.8%.
Embodiment 2
After in the Erlenmeyer flask of 50ml, adding rapeseed oil 10.0 grams, methyl alcohol 0.4 gram, the abundant stirring of rapeseed oil fatty acid methyl esters 5.2 grams, add NOVOZYM435 immobilized lipase acid enzyme 0.4 gram, with tapered bottleneck sealing, and put it in the vibrator, open vibrator, shake under the frequency of 150RPM, be warming up to 30 ℃, reaction was carried out about 24 hours.After reaction finishes, the NOVOZYM435 immobilized lipase is shifted out from reaction product, reactant is placed left standstill 12 hours then, treat deglycerizin layer after the layering by filtering, product rapeseed oil fatty acid methyl esters, the transformation efficiency of reaction reaches 95.6%.
Embodiment 3
After in the Erlenmeyer flask of 50ml, adding soya-bean oil 11.0 grams, methyl alcohol 0.45 gram, the abundant stirring of methyl soyate 5.8 grams, add NOVOZYM435 immobilized lipase acid enzyme 0.45 gram, with tapered bottleneck sealing, and put it in the vibrator, open vibrator, shake under the frequency of 150RPM, be warming up to 30 ℃, reaction was carried out about 24 hours.After reaction finishes, the NOVOZYM435 immobilized lipase is shifted out from reaction product, reaction product is placed left standstill 15 hours then, treat deglycerizin layer after the layering by filtering, the product methyl soyate, the transformation efficiency of reaction reaches 96.2%.
Embodiment 4
Preparation method's step of embodiment 4 is same as embodiment 1, and not being both lipase is LIPOZYMERM ZI immobilized lipase, and the transformation efficiency of its reaction reaches 59%.
Claims (6)
1, a kind of biological enzyme is made the method for vegetable fatty acids methyl esters, it is characterized in that this method comprises:
---with vegetables oil, methyl alcohol and solubility promoter vegetable fatty acids methyl esters, drop into closure and be equipped with in the container of stirring, after stirring, add lipase-catalyzed dose again, screw container cover, and the container that reactant will be housed is put into vibrator and is vibrated, oscillation frequency is 100RPM-200RPM, under 30 ℃ of-60 ℃ of temperature, reacted about 20-48 hour, wherein in 100 weight part vegetables oil, solubility promoter vegetable fatty acids methyl esters is the 50-100 weight part, lipase-catalyzed dose is the 4-8 weight part, and the mol ratio of vegetables oil and methyl alcohol is 1: 1;
---by filtering lipase-catalyzed dose is shifted out from reaction product;
---reaction product placed leaves standstill more than 12 hours, treat deglycerizin layer after the layering, product vegetable fatty acids methyl esters.
2, biological enzyme according to claim 1 prepares the method for vegetable fatty acids methyl esters, it is characterized in that described vegetables oil is Oleum Gossypii semen, rapeseed oil, soya-bean oil, peanut oil, plam oil, Oleum Cocois, siritch, Oleum Helianthi, sesame oil, Semen Maydis oil, broccoli oil or Viscotrol C.
3, biological enzyme according to claim 1 prepares the method for vegetable fatty acids methyl esters, it is characterized in that described vegetables oil is rapeseed oil, Oleum Gossypii semen, soya-bean oil, peanut oil, plam oil or Oleum Cocois.
4, biological enzyme according to claim 1 is made the method for vegetable fatty acids methyl esters, it is characterized in that described methanol purity is greater than 99.5%.
5, biological enzyme according to claim 1 is made the method for vegetable fatty acids methyl esters, it is characterized in that described solubility promoter vegetable fatty acids methyl esters is vegetable seed grease fat methyl esters, cottonseed oil fatty acid methyl esters, methyl soyate or palm oil fatty acid methyl esters, peanut oil fatty acid methyl esters, coconut oil fatty acid methyl ester or broccoli fatty acid oil methyl esters.
6, biological enzyme according to claim 1 is made the method for vegetable fatty acids methyl esters, it is characterized in that described lipase is NOVOZYM435 immobilized lipase, LIPOZYME RM IM immobilized lipase or LIPASE-RH immobilized lipase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031214940A CN1183238C (en) | 2003-03-28 | 2003-03-28 | Method of manufacturing vegetable oil methyl aliphate using biological enzyme method |
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| Application Number | Priority Date | Filing Date | Title |
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| CNB031214940A CN1183238C (en) | 2003-03-28 | 2003-03-28 | Method of manufacturing vegetable oil methyl aliphate using biological enzyme method |
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| CN1442472A CN1442472A (en) | 2003-09-17 |
| CN1183238C true CN1183238C (en) | 2005-01-05 |
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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7473539B2 (en) | 2004-09-20 | 2009-01-06 | Sunho Biodiesel Corporation | Methods for producing alkyl esters |
| CN101194019A (en) | 2005-06-13 | 2008-06-04 | 诺维信公司 | Production of degummed fatty acid alkyl esters |
| CN101831280B (en) * | 2010-05-19 | 2013-12-18 | 濮阳市诚信钻采助剂有限公司 | Carrier of active ingredient of defoaming agent and preparation method thereof |
| CN105950673A (en) * | 2010-06-18 | 2016-09-21 | 布特马斯先进生物燃料有限责任公司 | Extraction solvents derived from oil for alcohol removal in extractive fermentation |
| KR20130032897A (en) * | 2010-06-18 | 2013-04-02 | 부타맥스 어드밴스드 바이오퓨얼스 엘엘씨 | Production of alcohol esters and in situ product removal during alcohol fermentation |
| CN103695184A (en) * | 2013-12-31 | 2014-04-02 | 张锦碧 | Novel process for preparing biodiesel from illegal cooking oil |
| CN109852483A (en) * | 2018-12-29 | 2019-06-07 | 中南林业科技大学 | A method of fatty acid methyl ester is prepared with Rice bran crude oil |
| CN111378700A (en) * | 2020-02-24 | 2020-07-07 | 广东聚石化学股份有限公司 | Preparation method of camellia oil fatty acid ester |
| CN111437220B (en) * | 2020-04-29 | 2022-09-06 | 广东聚石化学股份有限公司 | Camellia oil fatty acid ester composition and preparation method and application thereof |
| CN115197784B (en) * | 2022-07-08 | 2024-01-09 | 华南理工大学 | A lard substitute for fat and its preparation method and application |
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