CN100347271C - Process of producing biological diesel oil through catalysis of fatty acid and acid-containing grease with microbe cell - Google Patents
Process of producing biological diesel oil through catalysis of fatty acid and acid-containing grease with microbe cell Download PDFInfo
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- CN100347271C CN100347271C CNB2006100897671A CN200610089767A CN100347271C CN 100347271 C CN100347271 C CN 100347271C CN B2006100897671 A CNB2006100897671 A CN B2006100897671A CN 200610089767 A CN200610089767 A CN 200610089767A CN 100347271 C CN100347271 C CN 100347271C
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- 239000002253 acid Substances 0.000 title claims abstract description 25
- 239000004519 grease Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 8
- 239000002283 diesel fuel Substances 0.000 title abstract description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract 2
- 229930195729 fatty acid Natural products 0.000 title abstract 2
- 239000000194 fatty acid Substances 0.000 title abstract 2
- 150000004665 fatty acids Chemical class 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000002808 molecular sieve Substances 0.000 claims abstract description 14
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 239000003921 oil Substances 0.000 claims description 30
- 235000019198 oils Nutrition 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 210000004027 cell Anatomy 0.000 claims description 16
- 239000003225 biodiesel Substances 0.000 claims description 15
- 239000002551 biofuel Substances 0.000 claims description 15
- 150000002632 lipids Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 235000021588 free fatty acids Nutrition 0.000 claims description 10
- 239000004367 Lipase Substances 0.000 claims description 7
- 102000004882 Lipase Human genes 0.000 claims description 7
- 108090001060 Lipase Proteins 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 235000019421 lipase Nutrition 0.000 claims description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 240000005384 Rhizopus oryzae Species 0.000 claims description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- 102000004895 Lipoproteins Human genes 0.000 claims description 4
- 108090001030 Lipoproteins Proteins 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
- 239000012075 bio-oil Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 210000001822 immobilized cell Anatomy 0.000 claims description 4
- 230000003834 intracellular effect Effects 0.000 claims description 4
- 230000000813 microbial effect Effects 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 3
- 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 description 2
- 241000195493 Cryptophyta Species 0.000 claims description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 244000057114 Sapium sebiferum Species 0.000 claims description 2
- 235000005128 Sapium sebiferum Nutrition 0.000 claims description 2
- 241000269319 Squalius cephalus Species 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008157 edible vegetable oil Substances 0.000 claims description 2
- 235000021323 fish oil Nutrition 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 239000011496 polyurethane foam Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 210000000582 semen Anatomy 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000002383 tung oil Substances 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 125000005456 glyceride group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 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
- 239000003513 alkali Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
The microbe cell catalyzed process of converting fatty acid and acid-containing grease into biological diesel oil belongs to the field of biological grease synthesizing technology. The reaction is performed inside in a no-solvent system or an organic solvent system, and 3A type molecular sieve in the amount of 5-10 times water produced in the reaction is added into the reaction system to absorb water selectively for the balance to be shifted toward the product direction so as to raise the catalysis efficiency and to raise the yield of biological diesel oil.
Description
Technical field
The invention belongs to the synthetic field of bio-oil, particularly proposed a kind of microorganism cells catalysis lipid acid and contained acid (lipid acid) grease production method of bio-diesel oil.When utilizing the whole-cell catalytic preparing biodiesel from lipid, in reaction system, add certain water-retaining agent, the novel process that bio-diesel yield significantly improves.
Background technology
One of prospect of oil prodution industry-biofuel is by the long chain fatty acid ester class material of bio-oil raw material by the transesterification reaction generation, is a kind of novel non-pollution of renewable energy.The combustionproperty of biofuel can be that diesel oil matches in excellence or beauty with traditional oil.Simultaneously, it is that diesel oil compares that to have a raw material renewable with traditional oil, environmental friendliness, flash-point height, cetane value advantages of higher.Thereby the research of biofuel and use to be subjected to widely and pay close attention to.
The production method of biofuel mainly contains chemical method, biological enzyme and supercutical fluid method at present, wherein because free fatty acids and less water that the biological enzyme biodiesel synthesis has in reaction conditions gentleness, non-pollutant discharge, the glyceride stock do not influence advantages such as enzymatic reaction, the developing direction that meets Green Chemistry, thereby be subject to people's attention day by day.
The obstruction biological enzyme prepares the cost of the principal element catalyzer enzyme of biofuel industrialization and compares higher with employed acid of chemical method or alkali.Adopt the microbe whole-cell that produces intracellular lipase to replace traditional fixed lipase catalyzed grease transesterification reaction to prepare biofuel, save the steps such as separation, purifying and immobilization in the immobilized lipase production process, be expected to reduce significantly the production cost of process for preparing biodiesel by enzyme.
Another principal element of decision production of biodiesel cost is the glyceride stock cost.Discussion is that the feedstock production biofuel more and more is subjected to people's attention with cheap grease.Often contain some lipid acid in the cheap glyceride stock.Lipid acid and short chain alcohol (using methyl alcohol) reaction can prepare biofuel equally, but the water byproduct that generates in the reaction process can influence the yield of biofuel, causes final grease transformation efficiency lower, and bio-diesel yield is low.So how to remove the water that generates in the reaction process timely and effectively and be the key that improves bio-diesel yield when being raw material with the acid-containing oil.
There is the scholar to propose in reaction system, to add silica gel, still because the micropore of silica gel is far longer than the molecular diameter of reactant methanol, so in suction, inevitably adsorb a certain amount of methyl alcohol to remove the water that dereaction produces.If the increase methanol usage not only increases cost, aggravated toxicity again to lipase.The present invention proposes utilizing full cell to transform as catalyzer in the process of lipid acid or preparing biodiesel by acid-containing greasy, and the adding micropore is littler than methyl alcohol diameter
Molecular sieve is as water-retaining agent, and optionally the water in the absorption system does not adsorb methyl alcohol, has improved the yield of catalytic efficiency and biofuel greatly.
Summary of the invention
The object of the present invention is to provide a kind of microorganism cells catalysis lipid acid and contain acid (lipid acid) grease production method of bio-diesel oil, improved the yield of catalytic efficiency and biofuel.
The present invention carries out in the preparation process of biofuel utilizing full cell to transform lipid acid or acid-containing oil and short chain alcohol (methyl alcohol, ethanol etc.) as catalyzer, this reaction can be carried out in solvent-free system, also can in organic solvent system, carry out, be reflected at 35-50 ℃ and carry out, in reaction system, add 5-10 doubly
Molecular sieve water-retaining agent (based on the water yield that produces), optionally the water in the absorption system does not adsorb methyl alcohol.
Described microbe whole-cell comprises bacterium, yeast and the fungal cell that produces intracellular lipase, and what these cells can be for free form also can be the immobilization form.Comprise R.oryzae IFO4697 free cell and be immobilized in immobilized cell on the polyurethane foam carrier, and through the crosslinked immobilized cell of linking agent (as glutaraldehyde etc.).
Described grease is a bio-oil, comprises free fatty acids, and the various Vegetable oil lipoprotein, animal grease, microbial oil, waste edible oil, the oil refining pin material that contain free fatty acids.
Described Vegetable oil lipoprotein is Viscotrol C, rapeseed oil, soybean oil, peanut oil, Semen Maydis oil, oleum gossypii seminis, Rice pollard oil, tung oil, Chinese vegetable tallow.
Described animal grease is fish oil, lard.
Described microbial oil comprises yeast grease, bacterium grease, algae grease.
The carbonatoms of described free fatty acids is 12-22.
Described short chain alcohol is methyl alcohol, ethanol, propyl alcohol, butanols or amylalcohol.
Described water-retaining agent is
Molecular sieve.
Reaction system can be solvent-free system; Also can be organic solvent system, particularly including the t-butanol solvent system.
The invention has the advantages that: with do not add
Molecular sieve is compared, and in the process of microbe whole-cell catalysis free fatty acids and acid-containing oil production biofuel, bio-diesel yield improves more than 10% in the identical time, has improved production efficiency greatly.
Embodiment
Embodiment 1
With mol ratio is 1.5: 1 methyl alcohol and oleic acid (oleic acid 5g), 3.2g
Molecular sieve, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 35 ℃ after, the adding dry weight is that the immobilization R.oryzae IFO4697 cell of oil quality 6% begins reaction, be about 88% through 24 hours artifact diesel oil yield, compare with contrast (do not add molecular sieve, other condition is identical), yield improves 12%.
Embodiment 2
With mol ratio be 1.5: 1 ethanol and oleic acid (oleic acid 5g), based on the trimethyl carbinol and the 6.4g of grease volume 100%
Molecular sieve, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, the adding dry weight is that the immobilization R.oryzae IFO4697 cell of oil quality 6% begins reaction, be about 90% through 24 hours artifact diesel oil yield, compare with contrast (do not add molecular sieve, other condition is identical), yield improves 14%.
Embodiment 3
With mol ratio be 4: 1 methyl alcohol and the waste oil (5g) that contains 20% (m/m) free fatty acids, based on the trimethyl carbinol and the 3.2g of grease volume 150%
Molecular sieve, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 35 ℃ after, the adding dry weight is that the free R.oryzae IFO4697 cell of oil quality 5% begins reaction, through 24 hours artifact diesel oil yield was 87%, compare with contrast (do not add molecular sieve, other condition is identical), yield improves 10%.According to the foregoing description, when the microbe whole-cell catalysis free fatty acids of utilization product intracellular lipase or acid-containing oil raw material and short chain alcohol are carried out the transesterification reaction biodiesel synthesis, add an amount of
Molecular sieve is removed the water that produces in the reaction process, can significantly improve bio-diesel yield.
Claims (6)
1. microorganism cells catalysis lipid acid and acid-containing oil production method of bio-diesel oil, it is characterized in that: carry out in the preparation process of biofuel utilizing full cell to transform lipid acid or acid-containing oil and short chain alcohol as catalyzer, this be reflected at carry out in the solvent-free system or organic solvent system in carry out, in reaction system, add doubly based on the water yield 5-10 that produces in the reaction process
The molecular sieve water-retaining agent is reflected at 35-50 ℃ and carries out, and methyl alcohol or ethanol and oleic mol ratio are 1.5～4: 1, and the quality of molecular sieve is 60%～120% of an oil quality; Optionally the water that generates in the absorption system makes balance move to the product direction, has improved the yield of catalytic efficiency and biofuel.
2, in accordance with the method for claim 1, it is characterized in that: described microbe whole-cell comprises bacterium, yeast and the fungal cell that produces intracellular lipase, and these cells are free form or immobilization form; Comprise R.oryzae IFO 4697 free cells or be immobilized in immobilized cell on the polyurethane foam carrier, through linking agent glutaraldehyde cross-linking immobilized cell.
3, in accordance with the method for claim 1, it is characterized in that: described solvent-free system comprises the system of not adding any other reaction medium; Organic solvent system comprises the t-butanol solvent system, and it is 30%-200% that solvent has greasy volume ratio.
4, in accordance with the method for claim 1, it is characterized in that: described acid-containing oil is a bio-oil, comprises free fatty acids, contains Vegetable oil lipoprotein, animal grease, microbial oil, the waste edible oil of free fatty acids or the pin material of refining oil; Described Vegetable oil lipoprotein is Viscotrol C, rapeseed oil, soybean oil, peanut oil, Semen Maydis oil, oleum gossypii seminis, Rice pollard oil, tung oil or Chinese vegetable tallow; Described animal grease is fish oil or lard; Described microbial oil comprises yeast grease, bacterium grease or algae grease.
5, in accordance with the method for claim 4, it is characterized in that: the carbonatoms of described free fatty acids is 12-22.
6: described short chain alcohol is methyl alcohol, ethanol, propyl alcohol, butanols or amylalcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100897671A CN100347271C (en) | 2006-07-14 | 2006-07-14 | Process of producing biological diesel oil through catalysis of fatty acid and acid-containing grease with microbe cell |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100897671A CN100347271C (en) | 2006-07-14 | 2006-07-14 | Process of producing biological diesel oil through catalysis of fatty acid and acid-containing grease with microbe cell |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1888020A CN1888020A (en) | 2007-01-03 |
| CN100347271C true CN100347271C (en) | 2007-11-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100897671A Active CN100347271C (en) | 2006-07-14 | 2006-07-14 | Process of producing biological diesel oil through catalysis of fatty acid and acid-containing grease with microbe cell |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105694992A (en) * | 2014-11-24 | 2016-06-22 | 曹小恭 | Bionic light crude oil, and preparation method thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102021207B (en) * | 2010-11-04 | 2013-08-14 | 清华大学 | On-line dehydration process for preparing biodiesel from renewable grease through catalysis of lipase |
| CN103695484A (en) * | 2013-12-23 | 2014-04-02 | 山西华顿实业有限公司 | Method of synthesizing biodiesel by applying lipase catalysis |
| CN105985867A (en) * | 2015-02-05 | 2016-10-05 | 昆明红火科技有限公司 | Method for preparing biological fuel oil from microbial catalytic oil and fat |
| CN108384729A (en) * | 2018-01-15 | 2018-08-10 | 浙江工业大学 | A kind of microbial cell crystalline substance glue and its preparation method and application |
| CN110129400B (en) * | 2019-05-25 | 2023-09-01 | 华南理工大学 | Method for improving odd-carbon chain fatty acid content of microbial oil |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1453332A (en) * | 2003-04-24 | 2003-11-05 | 华南理工大学 | Biologically catalystic process of converting fat into ester to produce biological diesel oil |
| CN1648207A (en) * | 2004-12-23 | 2005-08-03 | 大连理工大学 | Process for coupling producing bioloigical diesel oil and 1,3-propylene glycol |
-
2006
- 2006-07-14 CN CNB2006100897671A patent/CN100347271C/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1453332A (en) * | 2003-04-24 | 2003-11-05 | 华南理工大学 | Biologically catalystic process of converting fat into ester to produce biological diesel oil |
| CN1648207A (en) * | 2004-12-23 | 2005-08-03 | 大连理工大学 | Process for coupling producing bioloigical diesel oil and 1,3-propylene glycol |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105694992A (en) * | 2014-11-24 | 2016-06-22 | 曹小恭 | Bionic light crude oil, and preparation method thereof |
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| CN1888020A (en) | 2007-01-03 |
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