CN101709225A - Method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil - Google Patents
Method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil Download PDFInfo
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- CN101709225A CN101709225A CN200910155272A CN200910155272A CN101709225A CN 101709225 A CN101709225 A CN 101709225A CN 200910155272 A CN200910155272 A CN 200910155272A CN 200910155272 A CN200910155272 A CN 200910155272A CN 101709225 A CN101709225 A CN 101709225A
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- vegetable oil
- reaction
- catalytic hydrodeoxygenation
- diesel components
- lipoprotein
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- 235000015112 vegetable and seed oil Nutrition 0.000 title claims abstract description 33
- 239000008158 vegetable oil Substances 0.000 title claims abstract description 33
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003921 oil Substances 0.000 claims abstract description 16
- 235000019198 oils Nutrition 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims abstract description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000012263 liquid product Substances 0.000 claims abstract description 4
- 102000004895 Lipoproteins Human genes 0.000 claims description 18
- 108090001030 Lipoproteins Proteins 0.000 claims description 18
- 235000020238 sunflower seed Nutrition 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 235000019483 Peanut oil Nutrition 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 239000000312 peanut oil Substances 0.000 claims description 4
- 235000013311 vegetables Nutrition 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- ZJKABZNFELLAQQ-UHFFFAOYSA-N octane Chemical compound CCCCCCCC.CCCCCCCC ZJKABZNFELLAQQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 23
- 238000003756 stirring Methods 0.000 abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002485 combustion reaction Methods 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005336 cracking Methods 0.000 abstract description 2
- 238000005119 centrifugation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000012188 paraffin wax Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- 239000010773 plant oil Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003225 biodiesel Substances 0.000 description 2
- 239000002551 biofuel Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
-
- 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
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention provides a method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil, which prepares high heat-value alkane by catalytic hydrodeoxygenation of the vegetable oil. The method comprises the following reaction steps: adding the vegetable oil, barium sulphate-loaded palladium serving as a catalyst, as well as a solvent selected from n-hexane, n-heptane, n-octane and dodecane to a reactor; supplying hydrogen; allowing reaction pressure to be between 1 and 10 MPa; stirring and heating at 230 to 320 DEG C; performing reaction for 3 to 12 hours and then stopping the reaction; allowing the catalyst and liquid products to automatically separate after the obtained product is cooled to room temperature; and obtaining the diesel components containing high heat-value alkane without centrifugation, filtration and other complicated post treatment. The method has the advantages of simple preparation process, low reaction temperature, low solvent consumption, no cracking of carbon chain parts of the oil, high combustion heat value of target products and recyclable catalyst.
Description
Technical field
The present invention relates to the method for a kind of grease, be specifically related to the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil through catalytic hydrodeoxygenation process generation diesel component.
Background technology
Along with going from bad to worse of the in short supply day by day and global climate environment of Nonrenewable energy resources such as coal, oil, Sweet natural gas in the world wide, the development and use of the biomass resource of cleaning more and more cause people's attention.Longer chain fatty acid and ester thereof are the materials that a class is widespread in nature, and are saturated or the glyceryl ester of unsaturated fatty acids as the main ingredient of animal-plant oil, belong to renewable resources.In recent years, the technology of utilizing solid acid, alkaline catalysts catalysis animal-plant oil and methyl alcohol or ethanol to carry out preparing biodiesel by ester exchange has obtained research widely.Because the main ingredient of biofuel is fatty acid methyl ester or ethyl ester, so its oxygen level height, viscosity is big, calorific value is low, can not be directly used in power-equipments such as oil engine; Have a large amount of by-product glycerins in addition in the process of preparing biodiesel by ester exchange and generate, the aftertreatment meeting of glycerine increases production cost.
Diesel oil mainly is made up of the alkane that contains 10~22 carbon atoms, alkene, naphthenic hydrocarbon etc., and the combustion heat value height is the good fuel of heavy equipment.The common feature (all containing long carbochain part) on structure is formed in view of animal-plant oil and diesel oil changes animal-plant oil into renewable diesel component that straight-chain paraffin can obtain cleaning by modes such as hydrogenation deoxidation, decarboxylation, decarbonylations.Present catalysis animal-plant oil hydrogenation deoxidation prepares the relevant document of diesel component and patent is also less and its catalyst system therefor preparation technology is numerous and diverse, severe reaction conditions, the carbochain fracture is serious, and the product calorific value is low, has aromatic hydrocarbons to generate in the reaction process and causes carbon distribution easily.Based on above the deficiencies in the prior art, be necessary very much the oil hydrogenation deoxidization technique is improved.
Summary of the invention
The objective of the invention is to: a kind of method that simply Vegetable oil lipoprotein is changed into the high heating value diesel component that is suitable for use as automotive fuel is provided.
The method of preparing diesel components by catalytic hydrodeoxygenation of vegetable oil of the present invention, Vegetable oil lipoprotein makes diesel component through catalytic hydrodeoxygenation reaction highly selective, adopts the one kettle way reaction process directly to prepare, and reaction formula is as follows:
Reactions steps: in reactor, add Vegetable oil lipoprotein, catalyzer and solvent charge into hydrogen, and reaction pressure is 1-10MPa, open and stir and heating, temperature of reaction is 230-320 ℃, and stopped reaction behind the reaction 3-12h is to be cooled to room temperature, catalyzer separates automatically with liquid product, need not the diesel component that numerous and diverse aftertreatments such as centrifugal, filtration can obtain containing high heating value alkane.
Vegetable oil lipoprotein of the present invention comprises sunflower seed oil, rapeseed oil, soybean oil, peanut oil, coconut wet goods vegetables oil.
Catalyzer of the present invention is the carrier loaded active component palladium of barium sulfate.The quality percentage composition of active component palladium is that the preferable content of 1-10% is 3-5%.
The weight ratio of catalyzer of the present invention and vegetables oil is 1: 2~5, and the weightmeasurement ratio of vegetables oil and solvent is 1g: 15~30mL.
Vegetable oil lipoprotein catalytic hydrodeoxygenation temperature of reaction of the present invention is 230-320 ℃, and preferable temperature of reaction is 250-290 ℃.
Vegetable oil lipoprotein catalytic hydrodeoxygenation reaction pressure of the present invention is 1-10MPa, and preferable reaction pressure is 3-5MPa.
Vegetable oil lipoprotein catalytic hydrodeoxygenation of the present invention reaction solvent for use is any in normal hexane, normal heptane, octane or the dodecane, and preferred solvents is a normal hexane.
Preparation method of the present invention, reaction has very high catalytic activity and selectivity to the Vegetable oil lipoprotein catalytic hydrodeoxygenation.Compared with the prior art, the substantive distinguishing features that has of the present invention is:
1, the grease carbochain does not partly have cracking, and is good to target product selectivity; Product combustion heat value height is the reproducible diesel oil alternative fuel of cleaning.
2, reaction finishes rear catalyst and separates automatically with liquid product, need not the diesel component that numerous and diverse aftertreatment such as centrifugal, filtration can obtain containing high heating value alkane.
3, compare with the preparation technology of biofuel, no glycerine generates in the Vegetable oil lipoprotein hydrogenation deoxidation process, thereby has effectively avoided the increase of the production cost that brings because of the glycerine aftertreatment.
4, catalyst preparation process is simple, and raw material is cheap and easy to get, and catalyzer can recycle, and is convenient to scale operation.
5, temperature of reaction reduces significantly, is the production process of less energy-consumption.
6, solvent load is few, and is cheap and easy to get, and boiling point is low, is easy to recycle.
Embodiment
Embodiment 1
With 1.5g sunflower seed oil, 0.5g 2%Pd/BaSO
4Catalyzer and 30mL normal hexane add in the 100mL reactor, charge into hydrogen, and initial hydrogen pressure 3.0MPa opens and stirs and heating, stopped reaction behind 270 ℃ of reaction 7h, and to be cooled to room temperature, product liquid separates automatically with catalyzer, obtains clarifying diesel component.With high performance liquid chromatography and gas-chromatography product is carried out detection by quantitative respectively, the transformation efficiency of raw material sunflower seed oil can reach 100% as can be known, and the ultimate production of normal paraffin is 1.01g.Shown in the product table composed as follows:
Embodiment 2
With 1.0g sunflower seed oil, 0.4g 5%Pd/BaSO
4Catalyzer and 15mL octane add in the 100mL reactor, charge into hydrogen, and initial hydrogen pressure 5.0MPa opens and stirs and heating, stopped reaction behind 320 ℃ of reaction 5h, and to be cooled to room temperature, product liquid separates automatically with catalyzer, obtains clarifying diesel component.With high performance liquid chromatography and gas-chromatography product is carried out detection by quantitative respectively, the transformation efficiency of raw material sunflower seed oil can reach 98% as can be known, and the ultimate production of normal paraffin is 0.63g.Shown in the product table composed as follows:
Embodiment 3
With 1.5g peanut oil, 0.3g 5%Pd/BaSO
4Catalyzer and 25mL normal heptane add in the 100mL reactor, charge into hydrogen, and initial hydrogen pressure 6.0MPa opens and stirs and heating, stopped reaction behind 240 ℃ of reaction 12h, and to be cooled to room temperature, product liquid separates automatically with catalyzer, obtains clarifying diesel component.With high performance liquid chromatography and gas-chromatography product is carried out detection by quantitative respectively, the transformation efficiency of raw material peanut oil can reach 99% as can be known, and the ultimate production of normal paraffin is 1.00g.Shown in the product table composed as follows:
Embodiment 4
With 1.0g rapeseed oil, 0.3g 8%Pd/BaSO
4Catalyzer and 30mL dodecane add in the 100mL reactor, charge into hydrogen, and initial hydrogen pressure 3.0MPa opens and stirs and heating, stopped reaction behind 280 ℃ of reaction 8h, and to be cooled to room temperature, product liquid separates automatically with catalyzer, obtains clarifying diesel component.With high performance liquid chromatography and gas-chromatography product is carried out detection by quantitative respectively, the transformation efficiency of raw material rapeseed oil can reach 97% as can be known, and the ultimate production of normal paraffin is 0.69g.Shown in the product table composed as follows:
Embodiment 5
With 1.0g soybean oil, 0.2g 5%Pd/BaSO
4Catalyzer and 15mL normal hexane add in the 100mL reactor, charge into hydrogen, and initial hydrogen pressure 4.5MPa opens and stirs and heating, stopped reaction behind 270 ℃ of reaction 9h, and to be cooled to room temperature, product liquid separates automatically with catalyzer, obtains clarifying diesel component.With high performance liquid chromatography and gas-chromatography product is carried out detection by quantitative respectively, the transformation efficiency of raw soybeans oil can reach 98% as can be known, and the ultimate production of normal paraffin is 0.59g.Shown in the product table composed as follows:
Embodiment 6
With 1.0g Oleum Cocois, 0.5g 1%Pd/BaSO
4Catalyzer and 25mL octane add in the 100mL reactor, charge into hydrogen, and initial hydrogen pressure 3.5MPa opens and stirs and heating, stopped reaction behind 300 ℃ of reaction 3h, and to be cooled to room temperature, product liquid separates automatically with catalyzer, obtains clarifying diesel component.With high performance liquid chromatography and gas-chromatography product is carried out detection by quantitative respectively, the transformation efficiency of raw material Oleum Cocois can reach 95% as can be known, and the ultimate production of normal paraffin is 0.65g.Shown in the product table composed as follows.
Claims (8)
1. the method for a preparing diesel components by catalytic hydrodeoxygenation of vegetable oil, be that Vegetable oil lipoprotein makes high heating value alkane through catalytic hydrodeoxygenation, it is characterized in that adopting the one kettle way reaction process directly to prepare, adopt the one kettle way reaction process directly to prepare, reaction formula is as follows:
Step is as follows: in reactor, add Vegetable oil lipoprotein, catalyzer and solvent, charge into hydrogen, reaction pressure 1~10MPa, 230~320 ℃ of temperature, stopped reaction behind reaction 3~12h, to be cooled to room temperature, catalyzer separates automatically with liquid product, need not the diesel component that aftertreatments such as centrifugal, filtration can obtain containing high heating value alkane; Described catalyzer is the barium sulfate loaded palladium catalyst, and the quality percentage composition of palladium is 1~10%; Described solvent is a kind of in normal hexane, normal heptane, octane or the dodecane.
2. the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil according to claim 1 is characterized in that used Vegetable oil lipoprotein is a kind of in sunflower seed oil, rapeseed oil, soybean oil, peanut oil or the Oleum Cocois.
3. as the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil as described in the claim 2, it is characterized in that used Vegetable oil lipoprotein is sunflower seed oil and Oleum Cocois.
4. the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil according to claim 1 is characterized in that Vegetable oil lipoprotein hydrogenation deoxidation catalyst system therefor is the barium sulfate loaded palladium catalyst, and the quality percentage composition of palladium is 3~5%.
5. the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil according to claim 1, the weight ratio that it is characterized in that catalyzer and Vegetable oil lipoprotein is 1: 2~5, the weightmeasurement ratio of vegetables oil and solvent is 1g: 15~30mL.
6. the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil according to claim 1 is characterized in that Vegetable oil lipoprotein catalytic hydrodeoxygenation temperature of reaction is 250~290 ℃.
7. the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil according to claim 1 is characterized in that Vegetable oil lipoprotein catalytic hydrodeoxygenation reaction pressure is 3~5MPa
8. the method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil according to claim 1 is characterized in that Vegetable oil lipoprotein catalytic hydrodeoxygenation reaction solvent for use is a normal hexane.
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CN200910155272A CN101709225A (en) | 2009-12-10 | 2009-12-10 | Method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil |
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CN200910155272A CN101709225A (en) | 2009-12-10 | 2009-12-10 | Method for preparing diesel components by catalytic hydrodeoxygenation of vegetable oil |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101899318A (en) * | 2010-07-23 | 2010-12-01 | 浙江大学 | Method for preparing diesel hydrocarbons from vegetable fat through catalytic hydrogenation and deoxygenation |
CN102690673A (en) * | 2012-01-14 | 2012-09-26 | 河南科技大学 | Method for preparing biodiesel by vegetable oil through catalytic hydrocracking |
CN103725305A (en) * | 2013-12-17 | 2014-04-16 | 中国科学院广州能源研究所 | Method for preparing hydrocarbon liquid fuels from higher fatty acid methyl ester |
CN104479724A (en) * | 2014-11-19 | 2015-04-01 | 中国科学技术大学 | Method for preparing hydrocarbon liquid fuel from higher fatty acid and/or ester thereof by virtue of nonmetal catalysis |
CN104497992A (en) * | 2014-11-28 | 2015-04-08 | 中山职业技术学院 | Preparation method of antifreezing solution for engine cooling |
US9079811B2 (en) | 2013-06-10 | 2015-07-14 | Uop Llc | Linear alkylbenzenes from natural oils and methods of producing |
US9079814B2 (en) | 2013-06-10 | 2015-07-14 | Uop Llc | Linear alkylbenzenes from natural oils and methods of producing |
US9080134B2 (en) | 2013-06-10 | 2015-07-14 | Uop Llc | Linear alkylbenzenes from natural oils and methods of producing |
CN105176698A (en) * | 2015-08-12 | 2015-12-23 | 中国科学技术大学先进技术研究院 | Method for preparing aviation biofuel by catalytic hydrogenation of Jatropha carcas L. oil |
CN112495392A (en) * | 2020-11-16 | 2021-03-16 | 华南理工大学 | Method for preparing hydrocarbon compound by catalyzing grease with spinel catalyst loaded with Pd |
CN113200807A (en) * | 2021-05-12 | 2021-08-03 | 中国科学院山西煤炭化学研究所 | Method for preparing high-purity C16 and C18 normal mono-alkane |
CN114011415A (en) * | 2021-11-19 | 2022-02-08 | 南京师范大学 | Preparation method of high-load layered cobalt catalyst for preparing green diesel oil by grease hydrodeoxygenation |
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CN101103093A (en) * | 2005-01-14 | 2008-01-09 | 耐思特石油公司 | Method for the manufacture of hydrocarbons |
CN101020668A (en) * | 2006-10-20 | 2007-08-22 | 清华大学 | Process of synthesizing 4-methyl-5-formyl thiazole |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101899318A (en) * | 2010-07-23 | 2010-12-01 | 浙江大学 | Method for preparing diesel hydrocarbons from vegetable fat through catalytic hydrogenation and deoxygenation |
CN102690673A (en) * | 2012-01-14 | 2012-09-26 | 河南科技大学 | Method for preparing biodiesel by vegetable oil through catalytic hydrocracking |
US9080134B2 (en) | 2013-06-10 | 2015-07-14 | Uop Llc | Linear alkylbenzenes from natural oils and methods of producing |
US9079811B2 (en) | 2013-06-10 | 2015-07-14 | Uop Llc | Linear alkylbenzenes from natural oils and methods of producing |
US9079814B2 (en) | 2013-06-10 | 2015-07-14 | Uop Llc | Linear alkylbenzenes from natural oils and methods of producing |
CN103725305A (en) * | 2013-12-17 | 2014-04-16 | 中国科学院广州能源研究所 | Method for preparing hydrocarbon liquid fuels from higher fatty acid methyl ester |
CN103725305B (en) * | 2013-12-17 | 2016-02-24 | 中国科学院广州能源研究所 | A kind of higher fatty acid methyl esters prepares the method for liquid hydrocarbon fuel |
CN104479724A (en) * | 2014-11-19 | 2015-04-01 | 中国科学技术大学 | Method for preparing hydrocarbon liquid fuel from higher fatty acid and/or ester thereof by virtue of nonmetal catalysis |
CN104479724B (en) * | 2014-11-19 | 2016-02-03 | 中国科学技术大学 | A kind of nonmetal catalyzed higher fatty acid and/or its ester prepare the method for liquid hydrocarbon fuel |
CN104497992A (en) * | 2014-11-28 | 2015-04-08 | 中山职业技术学院 | Preparation method of antifreezing solution for engine cooling |
CN105176698A (en) * | 2015-08-12 | 2015-12-23 | 中国科学技术大学先进技术研究院 | Method for preparing aviation biofuel by catalytic hydrogenation of Jatropha carcas L. oil |
CN112495392A (en) * | 2020-11-16 | 2021-03-16 | 华南理工大学 | Method for preparing hydrocarbon compound by catalyzing grease with spinel catalyst loaded with Pd |
CN113200807A (en) * | 2021-05-12 | 2021-08-03 | 中国科学院山西煤炭化学研究所 | Method for preparing high-purity C16 and C18 normal mono-alkane |
CN114011415A (en) * | 2021-11-19 | 2022-02-08 | 南京师范大学 | Preparation method of high-load layered cobalt catalyst for preparing green diesel oil by grease hydrodeoxygenation |
CN114011415B (en) * | 2021-11-19 | 2024-06-04 | 南京师范大学 | Preparation method of high-loading layered cobalt catalyst for preparing green diesel oil through grease hydrodeoxygenation |
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