CN104194946A - Method for producing biodiesel from grease raw material with high acid value - Google Patents
Method for producing biodiesel from grease raw material with high acid value Download PDFInfo
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- CN104194946A CN104194946A CN201410385820.7A CN201410385820A CN104194946A CN 104194946 A CN104194946 A CN 104194946A CN 201410385820 A CN201410385820 A CN 201410385820A CN 104194946 A CN104194946 A CN 104194946A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
Abstract
The invention provides a method for producing biodiesel from a grease raw material with a high acid value, which has the advantages of mild conditions, clean process and no corrosion to a device. The method is characterized by reacting glycerol instead of lower alcohols (for example methanol and ethanol) with fatty acid in presence of an acidic ionic liquid without corrosion to the device to obtain a mixture of monoglyceride, diglyceride or triglyceride, removing water generated in the reaction out of the reaction system to break the chemical equilibrium of the reaction, and then under the action of a basic catalyst, carrying out ester change reaction on the esterified products with the low acid values by virtue of a mixture of methanol, isopropanol or isobutanol to produce biodiesel (fatty acid esters) with the low acid value and a low condensation point. The ionic liquid is recycled and the process cleanness is achieved.
Description
The application be that December 9, application number in 2011 are 201110408006.9 the applying date, denomination of invention is dividing an application of mono-kind of the < < method > > that utilizes high-acid value grease raw material production biofuel.
Technical field
The present invention relates to a kind of production method of biofuel.More particularly, be the novel method of utilizing the low acid number of ionic liquid-catalyzed high-acid value grease raw material production, low freezing point biodiesel.
Background technology
Fossil energy is as the consumption gradually of the Nonrenewable resources such as oil, coal and Sweet natural gas, the renewable energy sources such as biofuel that the biomass of take are carrier come into one's own just day by day, and the biofuel (mixture of multiple fatty acid methyl ester) that animal-plant oil and methyl alcohol is raw material production of wherein take has obtained the attention of countries in the world.
At present, the biodiesel technology being obtained by transesterification reaction by refined plant grease and methyl alcohol is a lot, as CN101126031; CN101134904; US7420072; US7112229 etc.But Chinese Shi Yige populous nation, adopting the country such as American-European to take refined plant grease is unpractical as raw material carrys out production biofuel.Meanwhile, China, as Yi Ge populous nation, produces a large amount of catering trade waste greases and grease production producer fatty wastes (also claiming soap stock, acidification oil) every year, and the feature of these greases is that acid number is high.As the acid number of rapeseed oil acidification oil can reach 140mgKOH/g (amounting to fatty acid content is 70%), and the acid number of oleic acid carburetion can reach 170mg KOH/g (amounting to fatty acid content is 85%), the acid number of catering trade waste grease (being commonly called as sewer oil) is also in 40mgKOH/g left and right.Take these high acid value waste greases is raw material, adopts the disclosed method of above-mentioned patent, due to lipid acid generation saponification reaction in adopted basic catalyst and raw oil material, cannot obtain qualified biofuel product.
The problem of bringing for solving high-acid value grease raw material production biofuel, US6642399 is by adding the generation homogeneous systems such as tetrahydrofuran (THF) (THF) cosolvent, adopt very high alcohol/grease mol ratio, under anhydrous condition, carry out esterification and the transesterification reaction of sulfuric acid catalysis, and then neutralize and transesterification reaction under the anhydrous alcohol solution katalysis of alkali, realize and make the abundant esterification of organic acid, transesterify and remove remaining acid to make the object that product is qualified.The method is severe reaction conditions not only, also exists in sulfuric acid corrosion equipment, alkali and lipid acid causes the shortcomings such as product yield is low, the large energy consumption height of methanol loop amount.
A kind of preparation method of biofuel is disclosed in CN101020837A, elder generation methyl alcohol and methyl esterification of fatty acid under sulphuric acid catalysis, after under methyl alcohol exists, with potassium hydroxide carry out base-catalyzed transesterification and will be in residual fat acid and water elution remove, thereby realize the production of low acid number biofuel.The method, compares with the disclosed technology of US6642399, does not adopt cosolvent, has reduced solvent recuperation, but still take sulfuric acid as catalyzer and alkali neutralize not trans-fatty acids, cause equipment corrosion, product yield low, produce the problems such as alkaline residue discharge.
Biofuel (fatty acid ester) is aliphatic fatty acid ester, its condensation point is generally 10 ℃ of left and right, and take the condensation point of the biofuel that plam oil, animal grease be raw material production generally more than 17 ℃, limited biofuel in the winter time or the use of high latitude area.For reducing the condensation point of biofuel, generally add pour point depressant at present.The amplitude of using pour point depressant not only biodiesel congealing point to be reduced is limited, and pour point depressant is conventionally containing heteroatomss such as nitrogen phosphate and sulfurs, in combustion processes, can pollute air, has reduced the meaning of biofuel as clean energy.
Summary of the invention
The present invention, for solving the problems of the technologies described above, provides a kind of method of utilizing high-acid value grease raw material production biofuel.
The technical scheme that the present invention realizes goal of the invention employing is that a kind of method of utilizing high-acid value grease raw material production biofuel, comprises the following steps:
A. take glycerine and high-acid value grease raw material is reactant, take ionic liquid as catalyzer, in encloses container, carry out esterification, and by the method vacuumizing, the water of esterification generation in described encloses container is extracted out in reaction process, obtain glycerine esterification product;
B. isolate described glycerine esterification product, add basic catalyst, with the mixture of methyl alcohol and Virahol or isopropylcarbinol, described glycerine esterification product is carried out to transesterification reaction, obtain fatty acid ester product;
C. the method for passing through distillation, by described fatty acid ester product separation, obtains biofuel.
Preferably, by the method vacuumizing, the air pressure in described encloses container is controlled to 10-300KPa.
Preferably, in described step a, before esterification, also comprise the step of measuring fatty acid content in described high-acid value grease raw material, then the mol ratio of controlling glycerine and lipid acid is (2-6): 1, the quality of described ionic liquid is the 8-40% of described reactant total mass.
Preferably, the temperature of reaction condition of described esterification is controlled at 120-140 ℃, and the reaction times is 1-3 hour.
Preferably, described ionic liquid is acidic ion liquid.
Preferably, the negatively charged ion of described acidic ion liquid is that alkyl imidazole ion, positively charged ion are sulfonate ion.
Preferably, described basic catalyst is potassium hydroxide or sodium hydroxide; The add-on of described basic catalyst is the 0.5-1.0% of lipid acid quality in described high-acid value grease raw material.
Preferably, the add-on of the mixture of methyl alcohol and Virahol or isopropylcarbinol is the 10-30% of high-acid value grease raw material total mass.
Preferably, the temperature of reaction condition of described transesterification reaction is controlled at 60-70 ℃, and the reaction times is controlled at 0.5-1.0 hour.
Preferably, in described step c, described distillation is carried out under temperature 180-220 ℃, the condition of pressure 0.5-10KPa.
The invention has the beneficial effects as follows:
1, raw materials for production take full advantage of a large amount of high-acid value grease raw materials that produce in life, and be conducive to utilization of waste material and reduce environmental pollution;
2, due to the lipid acid vacuum esterification dehydration under ionic liquid-catalyzed effect adopting in glycerine and high-acid value grease raw material, breaking esterification reacts with hydrolysising balance, the biofuel making (fatty acid methyl ester) product acid number is low, the acid number of reaction product can be below 0.5mgKOH/g, without aftertreatment;
3, without the methyl alcohol of separated popular response and the knockout tower of water mixture, shorten reaction process, reduce process energy consumption;
4, ionic-liquid catalyst and glycerine dissolve each other, and direct circulation is used, and without the washing of popular response, eliminate sewage discharge, and process is clean;
5, adopt ionic-liquid catalyst, eliminated the equipment corrosion of conventional sulfuric acid catalysis, reduce facility investment, reduce production costs;
6, adopt production method of the present invention, eliminated the saponification reaction of high-acid value grease raw material and basic catalyst, object product biofuel (fatty acid ester) yield is high;
7, adopt production method of the present invention, the condensation point of target product is lower than-5 ℃, any containing heteroatomic pour point depressant without adding, and simplifies production of biodiesel process, realizes biofuel direct, clean use in the winter time.
Embodiment
As industrialized preparing process, will introduce in detail implementation process of the present invention below.
First measure fatty acid content in high-acid value grease raw material; By glycerine and high-acid value grease raw material, in the mol ratio of glycerine and lipid acid, be (2-6): 1 ratio adds in reactor, open and stir; By the amount of high-acid value grease raw material and glycerine total mass 8-40%, add ionic-liquid catalyst again; Then closed reactor, is heated to 120-140 ℃ to reactor, and opens vacuum pump, makes pressure in reactor maintain the pressure of 10-300KPa; The water that the esterification that vacuum is extracted out generates enters water collecting tank and uses as recirculated cooling water; At 120-140 ℃, react stopped reaction after 1-3 hour; By reaction product and ionic-liquid catalyst and excess of glycerol pump to catalyst separating tank, reaction product is now monoglyceride, triglyceride or triglyceride level or three's mixture, ionic-liquid catalyst and excess of glycerol are in separating tank lower floor, after esterification, glyceride stock is on separating tank upper strata, the mixture pump of lower floor's excess of glycerol and catalyzer to another reaction kettle of the esterification is recycled, thereby without carrying out catalyzer and sweet oil separating; Catalyst separating tank upper strata grease is pumped into transesterification reactor, and add the mixture of methyl alcohol or Virahol or isopropylcarbinol, add catalyzer potassium hydroxide or sodium hydroxide, the add-on of methyl alcohol and Virahol or isopropylcarbinol mixture is the 10-30% of glyceride stock total mass, the add-on of catalyzer potassium hydroxide or sodium hydroxide is the 0.5-1.0% of glyceride stock, then closed reactor reacts 0.5-1.0 hour under the condition of 60-70 ℃; After reaction finishes, reaction product is pumped into glycerine and fatty acid ester (biofuel) separating tank, this separating tank lower floor is glycerine, at glycerine withdrawing can, stores and recycles; Glycerine and fatty acid ester separating tank upper strata are fatty acid ester, pump into fatty acid ester vacuum distilling apparatus, under the condition that is 0.5-10KPa at 180-220 ℃, pressure, distillation obtains methyl alcohol and Virahol or isopropylcarbinol mixture and high purity, low acid number, low condensation point fatty acid ester (biofuel), methyl alcohol and Virahol or the isopropylcarbinol mixture rate of recovery reach 100%, and the yield of fatty acid ester can reach 90%; Fatty acid ester vacuum distilling apparatus remaining 5% is the unreacted tri-glyceride of part and transesterification catalyst potassium hydroxide or sodium hydroxide, is back to transesterification reactor and reacts; The yield of total fatty acids ester (biofuel) can reach more than 95%.
As high-acid value grease raw material esterif iotacation step (step a) can adopt following specific embodiment:
Embodiment 1
Taking acid number is the glyceride stock 100g of 40mgKOH/g, and wherein fatty acid content is 20g, takes glycerine 13.15g, and glycerine and lipid acid mol ratio are 2: 1; Add ionic-liquid catalyst 9.1g, account for 8% of glycerine and high-acid value grease raw materials quality; 100g high-acid value grease raw material, glycerine 13.15g and 9.1g ionic-liquid catalyst are added in 500ml reactor, are under 10.0KPa, to vacuumize reaction 3 hours at 120 ℃, pressure; After reaction finishes, temperature of reaction is down to room temperature stratification, upper strata is low acid number grease after esterification, and after detecting, acid number is 0.5mgKOH/g, and productive rate is 103.6g; Lower floor, for not anti-glycerine and ionic-liquid catalyst, recycles.
Embodiment 2
Taking acid number is the glyceride stock 100g of 80mgKOH/g, and wherein fatty acid content is 40g, takes glycerine 52.57g, and glycerine and lipid acid mol ratio are 4: 1; Add ionic-liquid catalyst 22.89g, account for 15% of glycerine and high-acid value grease raw materials quality; 100g high-acid value grease raw material, glycerine 52.57g and 22.89g ionic-liquid catalyst are added in 500ml reactor, are under 100.0KPa, to vacuumize reaction 3 hours at 130 ℃, pressure; After reaction finishes, temperature of reaction is down to room temperature stratification, upper strata is low acid number grease after esterification, and after detecting, acid number is 0.3mgKOH/g, and productive rate is 108.4g; Lower floor, for not anti-glycerine and ionic-liquid catalyst, recycles.
Embodiment 3
Taking acid number is the glyceride stock 100g of 160mgKOH/g, and wherein fatty acid content is 80g, takes glycerine 157.72g, and glycerine and lipid acid mol ratio are 6: 1; Add ionic-liquid catalyst 77.32g, account for 30% of glycerine and high-acid value grease raw materials quality; 100g high-acid value grease raw material, glycerine 157.72g and 77.32g ionic-liquid catalyst are added in 500ml reactor, are under 200.0KPa, to vacuumize reaction 3 hours at 140 ℃, pressure; After reaction finishes, temperature of reaction is down to room temperature stratification, upper strata is low acid number grease after esterification, and after detecting, acid number is 0.2mgKOH/g, and productive rate is 116.3g; Lower floor, for not anti-glycerine and ionic-liquid catalyst, recycles.
Embodiment 4
Taking acid number is the glyceride stock 100g of 140mgKOH/g, and wherein fatty acid content is 70g, takes glycerine 138.0g, and glycerine and lipid acid mol ratio are 6: 1; Add ionic-liquid catalyst 95.2g, account for 40% of glycerine and high-acid value grease raw materials quality; 100g high-acid value grease raw material, glycerine 138.0g and 95.2g ionic-liquid catalyst are added in 500ml reactor, are under 300.0KPa, to vacuumize reaction 3 hours at 130 ℃, pressure; After reaction finishes, temperature of reaction is down to room temperature stratification, upper strata is low acid number grease after esterification, and after detecting, acid number is 0.1mgKOH/g, and productive rate is 114.6g; Lower floor, for not anti-glycerine and ionic-liquid catalyst, recycles.
As the transesterification steps of step b, can adopt following specific embodiment:
Embodiment 5
The acid number that embodiment 1 is obtained is that after the 103.6g esterification of 0.5mgKOH/g, grease and 10.4g methyl alcohol and isopropanol mixture (account for 10% of grease, the mol ratio of methyl alcohol and Virahol is 5: 1) add 300ml reactor, and add 0.57g sodium hydroxide (account for grease and methyl alcohol and isopropanol mixture quality 0.5%), under 60 ℃, normal pressure, react 1 hour; After reaction finishes, extract not coelonychia alcohol and isopropanol mixture under vacuum out, methyl alcohol and isopropanol mixture recycle; By the reaction product cool to room temperature stratification after the complete methyl alcohol of separation and isopropanol mixture, upper strata is fatty acid ester and a small amount of unreacted grease completely, after collection as the charging of fatty acid ester vacuum distilling; Lower floor is glycerine and catalyzer sodium hydroxide, reclaims glycerine.
Embodiment 6
The acid number that embodiment 2 is obtained is that after the 108.4g esterification of 0.3mgKOH/g, grease and 21.68g methyl alcohol and isopropanol mixture (account for 20% of grease, the mol ratio of methyl alcohol and Virahol is 6: 1) add 300ml reactor, and add 1.04g potassium hydroxide (account for grease and methyl alcohol and isopropanol mixture 0.8%), under 60 ℃, normal pressure, react 1 hour; After reaction finishes, extract not coelonychia alcohol and isopropanol mixture under vacuum out, methyl alcohol and isopropanol mixture recycle; By the reaction product cool to room temperature stratification after the complete methyl alcohol of separation and isopropanol mixture, upper strata is fatty acid ester and a small amount of unreacted grease completely, after collection as the charging of fatty acid ester vacuum distilling; Lower floor is glycerine and catalyzer sodium hydroxide, reclaims glycerine.
Embodiment 7
The acid number that embodiment 3 is obtained is that after the 116.3g esterification of 0.2mgKOH/g, the mixture of grease and 34.89g methyl alcohol and isopropylcarbinol (accounts for 30% of grease, the mol ratio of methyl alcohol and isopropylcarbinol is 7: 1) add 300ml reactor, and add 1.51g potassium hydroxide (account for grease and methyl alcohol and isopropylcarbinol mixture 1.0%), under 65 ℃, normal pressure, react 0.5 hour; After reaction finishes, extract not coelonychia alcohol and isopropylcarbinol mixture under vacuum out, methyl alcohol and isopropylcarbinol mixture recycle; By the reaction product cool to room temperature stratification after the complete methyl alcohol of separation and isopropylcarbinol mixture, upper strata is fatty acid ester and a small amount of unreacted grease completely, after collection as the charging of fatty acid ester vacuum distilling; Lower floor is glycerine and catalyzer sodium hydroxide, reclaims glycerine.
Embodiment 8
The acid number that embodiment 4 is obtained is that after the 114.6g esterification of 0.1mgKOH/g, grease and 22.92g methyl alcohol and isopropylcarbinol mixture (account for 20% of grease, the mol ratio of methyl alcohol and isopropylcarbinol is 6: 1) add 300ml reactor, and add 1.11g potassium hydroxide (account for grease and methyl alcohol and isopropylcarbinol mixture 0.8%), under 65 ℃, normal pressure, react 0.5 hour; After reaction finishes, extract not coelonychia alcohol and isopropylcarbinol mixture under vacuum out, methyl alcohol and isopropylcarbinol mixture recycle; By the reaction product cool to room temperature stratification after the complete methyl alcohol of separation and isopropylcarbinol mixture, upper strata is fatty acid ester and a small amount of unreacted grease completely, after collection as the charging of fatty acid ester vacuum distilling; Lower floor is glycerine and catalyzer sodium hydroxide, reclaims glycerine.
Embodiment as step c is as follows:
By embodiment 5-8 collect 445g fatty acid ester and on a small quantity not anti-rich mixture join in 1000ml reactor, under 180-220 ℃, the condition of 0.5-10KPa, vacuum distilling obtains faint yellow fatty acid ester 423g, it is 99.92% that fatty acid ester content in product is collected in stratographic analysis, and monoglyceride content is 0.06%; Acid number is 0.1mgKOH/g, and the condensation point of fatty acid ester is-6 ℃.
Finally it should be noted that: above embodiment is only in order to illustrate the present invention and unrestricted technical scheme described in the invention; Although therefore this specification sheets has been described in detail the present invention with reference to each above-mentioned embodiment, it will be understood by those of skill in the art that still and can modify or be equal to replacement the present invention; And all do not depart from technical scheme and the improvement thereof of the spirit and scope of the present invention, it all should be encompassed in claim scope of the present invention.
Claims (10)
1. a method of utilizing high-acid value grease raw material production biofuel, is characterized in that, comprises the following steps:
A. take glycerine and high-acid value grease raw material is reactant, take ionic liquid as catalyzer, in encloses container, carry out esterification, and by the method vacuumizing, the water of esterification generation in described encloses container is extracted out in reaction process, obtain glycerine esterification product;
B. isolate described glycerine esterification product, add basic catalyst, with the mixture of methyl alcohol and Virahol or isopropylcarbinol, described glycerine esterification product is carried out to transesterification reaction, obtain fatty acid ester product;
C. the method for passing through distillation, by described fatty acid ester product separation, obtains biofuel.
2. the method for production biofuel according to claim 1, is characterized in that, by the method vacuumizing, the air pressure in described encloses container is controlled to 10-300KPa.
3. the method for production biofuel according to claim 1 and 2, it is characterized in that, in described step a, before esterification, also comprise the step of measuring fatty acid content in described high-acid value grease raw material, the mol ratio of controlling again glycerine and lipid acid is (2-6): 1, and the quality of described ionic liquid is the 8-40% of described reactant total mass.
4. the method for production biofuel according to claim 3, is characterized in that, the temperature of reaction condition of described esterification is controlled at 120-140 ℃, and the reaction times is 1-3 hour.
5. the method for production biofuel according to claim 3, is characterized in that, described ionic liquid is acidic ion liquid.
6. the method for production biofuel according to claim 5, is characterized in that, the negatively charged ion of described acidic ion liquid is that alkyl imidazole ion, positively charged ion are sulfonate ion.
7. the method for production biofuel according to claim 3, is characterized in that, described basic catalyst is potassium hydroxide or sodium hydroxide; The add-on of described basic catalyst is the 0.5-1.0% of high-acid value grease raw materials quality.
8. the method for production biofuel according to claim 3, is characterized in that, the add-on of the mixture of methyl alcohol and Virahol or isopropylcarbinol is the 10-30% of high-acid value grease raw material total mass.
9. the method for production biofuel according to claim 3, is characterized in that, the temperature of reaction condition of described transesterification reaction is controlled at 60-70 ℃, and the reaction times is controlled at 0.5-1.0 hour.
10. the method for production biofuel according to claim 3, is characterized in that, in described step c, described distillation is carried out under temperature 180-220 ℃, the condition of pressure 0.5-10KPa.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011104080069A CN103160379A (en) | 2011-12-09 | 2011-12-09 | Method for producing biodiesel by virtue of high-acid-value oil raw material |
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| CN2011104080069A Division CN103160379A (en) | 2011-12-09 | 2011-12-09 | Method for producing biodiesel by virtue of high-acid-value oil raw material |
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| CN104194946A true CN104194946A (en) | 2014-12-10 |
| CN104194946B CN104194946B (en) | 2015-09-16 |
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| CN201410385820.7A Expired - Fee Related CN104194946B (en) | 2011-12-09 | 2011-12-09 | A kind of method utilizing high-acid value grease raw material production biofuel |
| CN2011104080069A Pending CN103160379A (en) | 2011-12-09 | 2011-12-09 | Method for producing biodiesel by virtue of high-acid-value oil raw material |
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Cited By (3)
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| CN105001983A (en) * | 2014-12-12 | 2015-10-28 | 北京恩泽福莱科技有限公司 | Method for reducing acid values of waste oils and fats by extraction esterification |
| WO2020074435A1 (en) | 2018-10-10 | 2020-04-16 | Basf Se | Method of producing biodiesel |
| WO2021204610A1 (en) | 2020-04-07 | 2021-10-14 | Basf Se | Energy efficient biodiesel production from natural or industrial waste oil |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104152276A (en) * | 2014-07-14 | 2014-11-19 | 石家庄新泰特种油有限公司 | Method for catalytic synthesis of monoglyceride from ionic liquid |
| CN104560412A (en) * | 2014-12-24 | 2015-04-29 | 江苏三力生物科技有限公司 | Preparation method for biodiesel |
| CN104593159B (en) * | 2015-02-05 | 2017-11-10 | 上海绿铭环保科技股份有限公司 | Using the method for complex solid Catalyst Production biodiesel |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105001983A (en) * | 2014-12-12 | 2015-10-28 | 北京恩泽福莱科技有限公司 | Method for reducing acid values of waste oils and fats by extraction esterification |
| CN105001983B (en) * | 2014-12-12 | 2019-04-05 | 北京恩泽福莱科技有限公司 | A kind of method that extracting, esterifying reduces waste grease acid value |
| WO2020074435A1 (en) | 2018-10-10 | 2020-04-16 | Basf Se | Method of producing biodiesel |
| WO2021204610A1 (en) | 2020-04-07 | 2021-10-14 | Basf Se | Energy efficient biodiesel production from natural or industrial waste oil |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103160379A (en) | 2013-06-19 |
| CN104194946B (en) | 2015-09-16 |
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