WO2011033346A1 - A process for conversion of low cost and high ffa oils to biodiesel - Google Patents
A process for conversion of low cost and high ffa oils to biodiesel Download PDFInfo
- Publication number
- WO2011033346A1 WO2011033346A1 PCT/IB2010/000592 IB2010000592W WO2011033346A1 WO 2011033346 A1 WO2011033346 A1 WO 2011033346A1 IB 2010000592 W IB2010000592 W IB 2010000592W WO 2011033346 A1 WO2011033346 A1 WO 2011033346A1
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- WO
- WIPO (PCT)
- Prior art keywords
- oil
- biodiesel
- catalyst
- methanol
- process according
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
-
- 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
Definitions
- the present invention relates to a process for conversion of low cost and high free fatty acid (FFA) oils to biodiesel.
- the present invention particularly relates to a process of converting high FFA containing feed stocks (FFA 20-85 %) to biodiesel in the presence of macro reticular and gel type acidic heterogeneous resin followed by transesterification in presence of homogeneous basic catalyst and separation of biodiesel and glycerine.
- Vegetable oil or fat is generally obtained by extraction or pressing natural seeds. Vegetable oil usually contains free fatty acids, phospholipids, sterols, water, tocopherols and other impurities. While as Palm fatty acid distillate (PFAD), Soya deodistillate, acid oil, are obtained as byproducts during refining of Palm oil or soya oil. These oils are mainly low cost material containing FFA in the range of 20-85%, while as restaurant grease is the waste oil collecting in grease traps from Kitchens of hotels and restaurants.
- PFAD Palm fatty acid distillate
- Soya deodistillate acid oil
- Vegetable seed oils have about 90% of the heat content of petroleum based diesel fuel and a favorable energy output/input ratio and, therefore, have the potential to replace congenital diesel fuel for compression ignition engines.
- the vegetable oils have another advantage as these have high cetane number up to 50. Added advantage of ⁇ 10 Cetane number is further obtained when vegetable oils are converted to methyl/ethyl monoesters. Thus these esters, with viscosity, boiling point and heat values in the range of diesel fuel and higher cetane number, have an advantage over the use of vegetable oils , as such .Therefore, these can be used as high cetane number blending components to the diesel fuel.
- the most common catalysts used for transesterification of vegetable oils to produce biodiesel include alkali, acids and enzymes.
- the alkali includes NaOH, KOH, sodium and potassium alkoxides such as sodium methoxide, potassium methoxide.
- acid catalysts are sulfuric acid, phosphoric acid, hydrochloric acid and sulfonic acids.
- biocatalyst lipase can be used for transesterification.
- alkaline catalysts the free fatty acid and water contents in the oil or fats significantly affect the transesterification by deactivating the catalyst and interfering with the separation of fatty acid esters and glycerol and for acidic catalyst e.g. H 2 S0 4 large quantity of alkali is used to neutralize the mineral acids and hence the disposal problems.
- Patent No. W09115452 where in, they described fatty acid alkyl esters are produced by catalytic transesterification of a vegetable oil using alkaline earth metal calcium, (Ca), or compounds thereof, at normal atmospheric pressure and normal room temperature below 50°C,
- CA Patent No. 2,316,141 where in, they described a process comprises forming a single phase solution of said triglyceride in an alcohol selected from methanol and ethanol, the ratio of alcohol to triglyceride being 15: 1 to 35: 1.
- the solution further comprises a co-solvent in an amount to effect formation of a single phase and a base catalyst for the esterification reaction. After a period of time, ester is recovered from the solution. Esterification is rapid and proceeds essentially to completion.
- the esters may be used as biofuel or biodiesel.
- Patent No. WO 2005/052103A1 discloses a process for the preparation of biodiesel, whereby oil is subjected to catalytical transesterification, settling, separation, bubble washing and micro Alteration under controlled conditions of temperature and turbulence. The process enables production of high quality fuel, termed as biodiesel within a period of as low as 50 hrs.
- US Patent No. 20060058540 discloses a process for the preparation of fatty acid esters from fats and oils of biological origin by transesterification with monohydric alcohols in presence of basic catalyst, the catalyst using salts of basic organic compound and carbonic acid e.g. guanidine.
- US Patent No. WO 2005/052103A1 discloses a process for the preparation of biodiesel, whereby oil is subjected to catalytical transesterification, settling, separation, bubble washing and micro Alteration under controlled conditions of temperature and turbulence. The process enables production of high quality fuel, termed as biodiesel within a
- reaction temperatures are typically in the range from about 20 to 200 degrees with reaction pressures in the range of about 150 psig to 400 psig.
- US Patent no. 20050274065 disclose a process for producing biofuels.
- the process may be enhanced by one or more of the following: 1) applying microwave or RF energy; (2) passing reactants over a heterogeneous catalyst; claim zeolite or cation exchange resin in H + at sufficiently high velocity to achieve high shear conditions; (3) maintaining the reaction at a pressure at or above autogeneous pressure, claim 10-100 psig.
- Enhanced processes using one or more of these steps can results in higher process rates, higher conversion levels or both.
- biodiesel process depends 70-80% on the cost of raw material.
- low cost raw materials e.g PFAD, soya deodistillate, acid oils restaurant grease, or waste cooking oil, Jatropha Curcas oil, mohua oil and animal fat for biodiesel process.
- the novelty of the present invention lies in the esterification of feedstock with high FFA content (20-85 %) without any pretreatment for biodiesel in the presence of macroreticular and gel type acidic heterogeneous resin as catalyst which can be used repeatedly (3-4 cycles) and no Alteration or washing is required after 1 st step of esterification.
- the esterified oil can be directly taken up for transesterification with base catalyst.
- the main object of the present invention is to provide a process for conversion of low cost and high FFA oils to biodiesel which obviates the drawbacks of the hitherto known prior art as detailed above.
- Another objective of the present invention is to provide a process for converting high FFA containing feed stocks( FFA 20-85 %) like palm fatty acid distillate (PFAD),restaurant grease, waste cooking oil , Soya deo distillate, acid oil, jatropha curcas oil, mohua oil etc to biodiesel.
- PFAD palm fatty acid distillate
- Soya deo distillate acid oil
- jatropha curcas oil mohua oil etc
- Yet another objective of the present invention is to provide the heterogenous resin either in a stainless steel basket or used directly with stirring to convert high FFA feedstock without neutralization or pretreatment.
- Still another objective of present invention is to use heterogenous resin repeatedly in the 1st step (4-5cycles) with lower alcohol.
- Yet another objective of the present invention is use of flexible feedstock without pretreatment or purification.
- Still another objective of present invention is to produce biodiesel at normal temperature and pressure from flexible feed stock having FFA 20-85% meeting the fuel grade quality as specified by ASTM/BIS.
- the present invention provides a process for converting high free fatty acid containing feedstocks (FFA 20-85 %) into biodiesel which comprises:
- step (b) heating the reactants of step (b) at a temperature in the range of 55-65 °C followed by mechanical stirring for a time period of 8 to 10 hours to obtain esterified oil;
- step (c) subjecting the esterified oil as obtained from step (c) to transesterification in the presence of homogeneous basic catalyst and methanol;
- step (d) separating product as obtained from step (d) into upper layer biodiesel and lower layer glycerol followed by recovering of methanol;
- step (e) washing the biodiesel layer as obtained from step (e) with hot water followed by drying to obtain biodiesel.
- the feedstocks containing 20-85% FFA are selected from the group consisting of palm fatty acid distillate (PFAD), restaurant grease, waste cooking oil, Soya deo distillate, acid oil, jatropha curcas oil and mohua oil.
- PFAD palm fatty acid distillate
- restaurant grease waste cooking oil
- Soya deo distillate acid oil
- jatropha curcas oil mohua oil
- the lower alcohols used for esterification is selected from the group consisting of methanol, ethanol or propanol in the ratio of 3: 1 to 35: 1 depending upon feedstock.
- the acidic heterogeneous resin catalyst is provided either in a jacketed glass reactor with stainless steel basket or used directly with stirring for esterification process without neutralization or pretreatment.
- the acidic heterogeneous resin catalyst in a basket is used repeatedly (4-5 cycles).
- the acidic heterogeneous resin catalyst used for esterification is selected from the group consisting of Tulsion-42 and Indion -130.
- the catalyst Tulsion-42 is used in the range of 5-20 % by weight of the feed stocks and Indion -130 is used in the range of 5-25
- homogeneous basic catalyst used for transesterification is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium methoxide and potassium methoxide.
- the transesterification is carried out at a temperature in the range of 55-70 °C for a period of 1 to 2 hrs.
- biodiesel is purified by washing with water or by distillation or adsorbent or combinations thereof.
- the product with acid value in the range of l-2mgKOH/g were transesterified in presence of homogeneous catalyst 0.5-0.75% using 2-3mol of methanol at a temperature of 55-70 °C for a period of 1 to 2 hrs.
- the biodiesel and glycerol layers were separated and the work up resulted in fuel grade biodiesel meeting ASTM/BIS specifications.
- Example-1 is given by way of illustration of the working of invention in actual practice and should not be construed to limit the scope of the present invention.
- Example 1 was repeated except that 10.02 g (10%) of catalyst Tulsion-42 was taken and acid value is 2.70 mgKOH/g after interval of 8 hrs respectively.
- the esterified Jatropha curcas oil was taken in second reactor and the transesterification was carried out in presence of 0.75% of potassium hydroxide with 15g methanol at 60°C. The reaction was complete in one hour, stirring stopped. The glycerol and biodiesel layers were separated, methanol recovered, the biodiesel layer was washed with water, and there was slight emulsion formation water in first two washings in total of four washings. The biodiesel dried and acid value of biodiesel was 0.46mg KOH /g and the conversion to biodiesel was 98%.
- Example 1 was repeated except that 15.37 gms (15%) of catalyst Tulsion -42 was loaded and acid value after 8 hrs is 2.12 mg KOH/g respectively.
- the esterified Jatropha curcas oil was taken in second reactor and the transesterification was carried out in presence of 0.75% of potassium hydroxide with methanol (21.6 g) at 65°C . The reaction was completed in one hour, stirring stopped.
- the glycerol and biodiesel layers were separated, methanol recovered ,the biodiesel layer was washed with water, in first two washings there was slight emulsion formation in total of four washings, the biodiesel dried and acid value of biodiesel was 0.45mg KOH /g and the conversion to biodiesel was observed 99 %.
- Example 1 was repeated except that catalyst Tulsion-42 was replaced by 10.49 gms (10%) of Indion-130 (available commercially) and acid value after 8 hrs was 10.24 mgKOH/g.
- the esterified Jatropha curcas oil was taken in second reactor and the transesterification was carried out in presence of 0.75%of potassium hydroxide with (15g) methanol at 65°C . The reaction was complete in one hour, stirring stopped. The glycerol and biodiesel layers were separated, methanol recovered, the biodiesel layer was washed with water, in first three washings there was emulsion formation in total of six washings.
- the biodiesel dried and acid value of biodiesel was 1.83 KOH /g and the conversion to biodiesel was 68.9% ExampIe-5
- Example 4 was repeated and Indion-130 (15%) was loaded and acid value is 5.55 after 8 hrs.
- the esterified Jatropha curcas oil was taken in second reactor and the transesterification was carried out in presence of 0.75% of potassium hydroxide with (21.6g) of methanol at 70 °C.
- the reaction was complete in one hour, stirring stopped.
- the glycerol and biodiesel layers were separated, methanol recovered, the biodiesel layer was washed with water, in first two washings there was emulsion formation in total of four washings.
- the biodiesel dried and acid value of biodiesel was 0.95mg KOH /g and the conversion to biodiesel was 79.2% ExampIe-6
- Example 5 was repeated with 20% Indion-130 and acid value after 8 hrs was 1.99 mgKOH/g.
- the esterified Jatropha curcas oil was taken in second reactor and the transesterification was carried out in presence of 0.75%of potassium hydroxide (20.9g) of methanol at 65°C.
- the reaction was completed in one hour, stirring stopped.
- the glycerol and biodiesel layers were separated, methanol recovered, the biodiesel layer was washed with water, in first washing there was slight emulsion formation in total of four washings.
- the biodiesel dried and acid value of biodiesel was 0.52mg KOH /g and the conversion to biodiesel was 98%.
- Example-7
- Example 7 is repeated except that raw material taken was restaurant Grease having acid value 34 mg KOH/g. The acid value after 8 hrs was 1.92 mgKOH/g .Each esterified oil was then worked up in the same procedure as in example 7. The acid value of biodiesel is 0.39mgKOH/g and the conversion to biodiesel was observed 97%.
- Example 7 is repeated except that raw material taken was soya deodistillate having acid value 38 mg KOH/g.
- the acid value after 8 hrs was 2.1mgKOH/g .
- the esterified oil was then worked up in the same procedure as in example 7.
- the acid value of biodiesel was0.47 mg KOH /g and the conversion to biodiesel was observed 94%.
- Examples 7-9 were repeated except that Indion-130 (15%) is used instead of Tulsion-42.
- the acid value of mohua oil, restaurant grease and soya deodistillate were 44mg KOH/g, 34mg KOH/g and 38 mg KOH/g respectively.
- Each esterified oil was then worked up in the same procedure as in examples 7, the acid value of biodiesel were 0.42mg KOH/g ,0.39mg KOH/g and 0.48mg KOH/g respectively and the conversion to biodiesel was observed 95%, 97% and 94% .
- Example 11 is repeated except that methanol is 216.49 gms (30moles).
- the acid value after removal of methanol is 4.12, 3.34, 3.17, 3.10 mgKOH/g after 2, 4, 6 and 8 hrs respectively.
- Example 12 is repeated except that Tulsion-42 (15%) is used instead of Indion-130.
- the acid value is 2.93 mg KOH/g after 8 hrs.
- Example 11 and 12 are repeated and the converted feed/biodiesel is purified by neutralization with NaOH and viscosity of fatty acid methyl ester at 40°C is 5.82 cSt (centistokes) after drying and washing.
- Example 15 is repeated and the feed is distilled off to get fuel grade palm fatty acid methyl ester with viscosity 4.47 cSt at 40°C and acid value 0.42-0.44 mg KOH/g.
- Another advantage of the process is using heterogeneous resins in SS basket where no Alteration of converted feed stock is required after 1 st stage.
- Another advantage is that flexible feedstocks can be used without pretreatment or neutralization.
- Yet another important advantage is the least disposal problems as no washing is required after 1 st stage/ester ification.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/395,871 US20120255223A1 (en) | 2009-09-15 | 2010-03-19 | process for conversion of low cost and high ffa oils to biodiesel |
CA2774343A CA2774343A1 (en) | 2009-09-15 | 2010-03-19 | A process for conversion of low cost and high ffa oils to biodiesel |
AU2010296982A AU2010296982A1 (en) | 2009-09-15 | 2010-03-19 | A process for conversion of low cost and high FFA oils to biodiesel |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN1900/DEL/2009 | 2009-09-15 | ||
IN1900DE2009 | 2009-09-15 |
Publications (1)
Publication Number | Publication Date |
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WO2011033346A1 true WO2011033346A1 (en) | 2011-03-24 |
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ID=42540143
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/IB2010/000592 WO2011033346A1 (en) | 2009-09-15 | 2010-03-19 | A process for conversion of low cost and high ffa oils to biodiesel |
Country Status (4)
Country | Link |
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US (1) | US20120255223A1 (en) |
AU (1) | AU2010296982A1 (en) |
CA (1) | CA2774343A1 (en) |
WO (1) | WO2011033346A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2623585A1 (en) * | 2012-01-24 | 2013-08-07 | Maria Aparecida Cirone Taboada ME | Process for producing high-yield biodiesel applying high acidity triglycerides with generation of glycerin 90% free of salts |
WO2013114381A1 (en) * | 2012-01-30 | 2013-08-08 | Venkata Sudhakar Edupuganti | Two stage process of producing fatty acid esters from palm fatty acid distillate (pfad) using acid chloride route for biodiesel |
EP2896608A1 (en) | 2014-01-15 | 2015-07-22 | Glycerosolution Quimica, Ltda | Process for the purification of crude glycerin |
WO2016098025A1 (en) * | 2014-12-17 | 2016-06-23 | Inis Biotech Llc | Process for the purification of biodiesel |
EP3299444A1 (en) * | 2016-09-21 | 2018-03-28 | Bio-Oils Huelva, S.L. | High efficiency method and catalyst for the production of alkyl esters from fatty acids with acid catalysis |
CZ308818B6 (en) * | 2019-12-20 | 2021-06-09 | Zdeněk Ing. Řičica | Method of producing alternative biofuel from waste fat sludge |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8957242B2 (en) | 2013-03-15 | 2015-02-17 | Renewable Energy Group, Inc. | Dual catalyst esterification |
FR3015515B1 (en) * | 2013-12-19 | 2016-02-05 | IFP Energies Nouvelles | PROCESS FOR PRETREATMENT OF HETEROGENEOUS CATALYSIS VEGETABLE OILS OF ESTERIFICATION OF FATTY ACIDS |
ES2580531T3 (en) | 2014-06-11 | 2016-08-24 | Neste Oyj | Method and apparatus for mixing fluids |
US9476009B2 (en) | 2015-03-05 | 2016-10-25 | Drexel University | Acidic methanol stripping process that reduces sulfur content of biodiesel from waste greases |
US10385254B2 (en) * | 2017-07-27 | 2019-08-20 | Saudi Arabian Oil Company | Ecofriendly emulsifier synthesis from esterified waste vegetable oil for wellbore drilling fluids |
AU2019262044B2 (en) | 2018-05-03 | 2024-05-30 | Renewable Energy Group, Inc. | Methods and devices for producing biodiesel, diesel-range hydrocarbons, and products obtained therefrom |
JP6770554B2 (en) * | 2018-07-23 | 2020-10-14 | 国立大学法人東京農工大学 | Biofuel manufacturing method |
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EP0192035A2 (en) * | 1985-01-21 | 1986-08-27 | Henkel Kommanditgesellschaft auf Aktien | Process for the pre-esterification of free fatty acids in raw fats and/or oils |
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DE102007052064A1 (en) * | 2007-10-30 | 2009-05-07 | Bayer Technology Services Gmbh | Reducing content of free fatty acids, useful for biodiesel production, comprises reacting fatty acids with an alcohol under use of ion-exchange-resin catalyst, separating water and alcohol and further reacting fatty acids with alcohol |
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US3441600A (en) * | 1966-06-16 | 1969-04-29 | Sinclair Research Inc | Liquid esters of neoalkyl polyols and neoalkyl fatty acids |
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US20070232817A1 (en) * | 2006-04-04 | 2007-10-04 | Companhia Brasileira De Metalurgia E Mineracao | Production process of biodiesel from the esterification of free faty acids |
AU2008318000A1 (en) * | 2007-10-30 | 2009-05-07 | Bayer Intellectual Property Gmbh | Method for the heterogenically catalyzed esterification of fatty acids |
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2010
- 2010-03-19 AU AU2010296982A patent/AU2010296982A1/en not_active Abandoned
- 2010-03-19 WO PCT/IB2010/000592 patent/WO2011033346A1/en active Application Filing
- 2010-03-19 US US13/395,871 patent/US20120255223A1/en not_active Abandoned
- 2010-03-19 CA CA2774343A patent/CA2774343A1/en not_active Abandoned
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EP0192035A2 (en) * | 1985-01-21 | 1986-08-27 | Henkel Kommanditgesellschaft auf Aktien | Process for the pre-esterification of free fatty acids in raw fats and/or oils |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2623585A1 (en) * | 2012-01-24 | 2013-08-07 | Maria Aparecida Cirone Taboada ME | Process for producing high-yield biodiesel applying high acidity triglycerides with generation of glycerin 90% free of salts |
WO2013114381A1 (en) * | 2012-01-30 | 2013-08-08 | Venkata Sudhakar Edupuganti | Two stage process of producing fatty acid esters from palm fatty acid distillate (pfad) using acid chloride route for biodiesel |
EP2896608A1 (en) | 2014-01-15 | 2015-07-22 | Glycerosolution Quimica, Ltda | Process for the purification of crude glycerin |
WO2016098025A1 (en) * | 2014-12-17 | 2016-06-23 | Inis Biotech Llc | Process for the purification of biodiesel |
EP3299444A1 (en) * | 2016-09-21 | 2018-03-28 | Bio-Oils Huelva, S.L. | High efficiency method and catalyst for the production of alkyl esters from fatty acids with acid catalysis |
CZ308818B6 (en) * | 2019-12-20 | 2021-06-09 | Zdeněk Ing. Řičica | Method of producing alternative biofuel from waste fat sludge |
Also Published As
Publication number | Publication date |
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AU2010296982A1 (en) | 2012-04-19 |
CA2774343A1 (en) | 2011-03-24 |
US20120255223A1 (en) | 2012-10-11 |
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