WO2007025360A2 - Procede catalytique destine a la transesterification d'huiles vegetales et de graisses au moyen de catalyseurs solides de base - Google Patents

Procede catalytique destine a la transesterification d'huiles vegetales et de graisses au moyen de catalyseurs solides de base Download PDF

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Publication number
WO2007025360A2
WO2007025360A2 PCT/BR2006/000174 BR2006000174W WO2007025360A2 WO 2007025360 A2 WO2007025360 A2 WO 2007025360A2 BR 2006000174 W BR2006000174 W BR 2006000174W WO 2007025360 A2 WO2007025360 A2 WO 2007025360A2
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WO
WIPO (PCT)
Prior art keywords
fact
accordance
catalyzer
alcohol
catalyzers
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Application number
PCT/BR2006/000174
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English (en)
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WO2007025360A3 (fr
Inventor
Donato Alexandre Gomes Aranda
Shizhong Zhao
David P. Tolle
Rafael Richard JOÃO
Rafael Thomaz Pergentino Santos
Guilherme Luis Monteiro De Souza
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Universidade Federal Do Rio De Janeiro
Sud Chemie Do Brasil
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Application filed by Universidade Federal Do Rio De Janeiro, Sud Chemie Do Brasil filed Critical Universidade Federal Do Rio De Janeiro
Publication of WO2007025360A2 publication Critical patent/WO2007025360A2/fr
Publication of WO2007025360A3 publication Critical patent/WO2007025360A3/fr

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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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • 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

Definitions

  • the present invention is related to the transesterification process of vegetable oils and animal fats.
  • the mono, di and triglycerides present in the oils and fats are transesterified with alcohols of 1 to 3 carbon atoms by the use of basic solid heterogeneous catalyzers in this process.
  • Biodiesel comprised of fatty acid esters, is an alternative fuel obtained as of renewable sources, such as vegetable oils and animal fats.
  • diesel derived from oil petro-diesel
  • biodiesel is an environmentally clean fuel, because it reduces the emissions of atmospheric pollutants and particulate material, in addition to being biodegradable and atoxic. Because it presents physical-chemical properties similar to petro-diesel, biodiesel can be used directly in the motor with no further significant mechanical modifications or expenditure in maintenance.
  • Biodiesel can be produced as of a series of oleaginous plants, such as soy, sunflower, canola, colza, castor bean, peanut, dende, cotton, fogger turnip oil, Jatopha curcas, among others.
  • animal fat as raw- material for biodiesel.
  • the oils and fats are hydrophobic substances, insoluble in water, consisting of 1 mol of glycerol and 3 moles of fatty acids, called triglycerides.
  • triglycerides There are four classic ways to achieve biodiesel as of triglycerides (F. Ma and M. A. Hanna, Bioresource Technology 70 (1999) 1-15) : direct use of the vegetable oils, microemulsions, thermal cracking (pyrolysis) and transesterification.
  • the direct use of the vegetable oils in natura as fuel presents a series of inconveniences, such as high viscosity, low volatility and presence of free fatty acids.
  • the main problems associated to the use of the vegetable oils in natura as combustibles are: incomplete combustion, leading to the accumulation of carbon deposits in the motor, and the thickening of the oil as a result of the polymerization of the unsaturated fatty acids.
  • the vegetable oil problem can be remedied by preparing microemulsions, making use of normal alcohols as surfactants, especially methanol and ethanol.
  • the use of these emulsions is limited by the instability to high temperatures and by the tendency of the alcohol to absorb air humidity, which requires special storage tanks to keep the fuel dry.
  • the thermal cracking of the triglycerides leads to the formation of paraffin, olefins and unsaturated methylic esters, with a composition similar to that of the oil derivatives.
  • the excess alcohol is recovered by distillation and glycerol is separated by decantation.
  • the ester is purified by washing and distillation. The transesterification results in a significant reduction of the viscosity, fitting into the specification of the diesel oil, and improving fuel atomization.
  • the transesterification catalyzed by homogeneous bases reguires the content of free fatty acids to be low, and the glycerids and alcohol to be anhydrides.
  • the presence of free acids requires a larger quantity of catalyzer so as to neutralize them, generating soluble soaps.
  • the water causes a saponification even more intense, decreasing the yield of the esters.
  • the formation of soap causes an increase in viscosity, formation of gel and solubilization of oil or fat in glycerol, thus making it more difficult to separate the esters.
  • the Patent US 2,383,601 recommends the use of alcohol anhydride when the content of free fat acids is high. Even so, inputs completely free from water, vegetable oils of acidity below 0.1% and homogeneous catalyzers as sodium hydroxide or potassium, methylate or sodium ethylate or potassium, the process presents a few problems.
  • the solubility, even if it is partial, of the homogeneous catalyzers in biodiesel, requires careful washing of the product, employing solutions of citric acid or another organic acid that will produce significant amounts of effluents demanding costs for the treatment.
  • Another relevant aspect is the quality of glycerol, important 5 byproduct generated in the process of transesterification, whose value is directly related to purity.
  • the current invention refers to the catalytic process presenting the ranges of optimal reaction conditions in terms of temperature, pressure, spatial time and concentration of reagents, for the efficient transformation of oils and fats into methylic or ethylic esters.
  • the current invention has also to do with the utilization of solid catalyzers, in the form of powder or granulates or extrudades in different sizes and forms, based on basic sites in the process of transesterification.
  • the objectives of the present invention include a process for the transesterification of vegetable oils and animal fats and the use of basic solid catalyzers in this process. IV. Description of the invention
  • tables 1 through 5 are shown which describe the reaction conditions employed respectively in samples from 1 through 5, as well as the results obtained in the transesterification of soy and sunflower oils.
  • the reactions were performed in autoclave batch reactor of the Parr type (Parr Instruments) with digital control of temperature, pressure and stirring.
  • the samples of solid catalyzers employed were in the form of cylindrical extrudades having an outside diameter of 1.5 mm or in the spherical form having an outside diameter of 3.0 mm or quadralobe extrudades having an outside diameter of 2.54 mm.
  • the conversion analyses were made by gas chromatography and presented values that were satisfactory for a single reaction step. Two or three reaction steps are sufficient to reach the specification of the product (biodiesel) .
  • basic solid catalyzers are used for the transesterification of mixtures of mono, di and tri-glycerides, with the esters of glycerol and carboxylic acids defined with chains containing between 10 and 22 carbon atoms, with or without double bonds between carbons, while said fatty compounds can be transesterified with methylic or ethylic alcohols.
  • solid catalyzers in the process of transesterification of glycerides of the present invention assumes that the solid catalyzers may be used in the form of powder or granulates or extrudades in different sizes and shapes, and the existence of basic sites capable of promoting the reaction.
  • esters may be employed also as solvents, tensoactives or intermediaries of tensoactives or detergents. In order to achieve high conversions and high selectivity for the esters, one must use alcohol/vegetable oils or animal alcohol/fats molar ratios between 3 and 15, being preferentially employed ratios between 4 and 12.
  • the high pressure favors the reaction; however, it is not indispensable.
  • the range of reactional temperature described above causes the pressure of the process to be mandatorily well above the atmospheric pressure.
  • the reactions involve components in the liquid phase and active sites located inside the particles of solid catalyzers, being, therefore, subject to limitation by mass transfer.
  • Any basic solid catalyzers that have thermal stability and baseline in the reaction conditions may be employed.
  • the following catalyzers are used: a) Catalyzers based on Hydrotalcites with an Mg/Al ratio between 0.2 and 700.
  • ratios of 0.38 to 500 are used.
  • catalyzers may be mixed to alumina at a content of hydrotalcite of 15 to 99%.
  • the alumina may have at least one of the following oxide additives: MgO, CaO, BeO, BaO, SrO, La 2 O 3 , CeO 2 , Pr 2 O 3 , Nd 2 O 3 , SmO 2 , Na 2 O, K 2 O, Cs 2 O, Rb 2 O, and ZrO 2 .
  • the content of these oxides introduced into the alumina can be of 5 to 90%.
  • the samples of catalyzers must be calcinated between 250 and 900 0 C. Preferentially, these catalyzers are calcinated between 300 and 750 0 C.
  • the catalyzers may be under the form of powder, or granulates, or extrudades with different formats; b) Alumina doped with alcalinous metals or terrous alkaline (doping content between 3% and 70%) .
  • the alumina can be doped with at least one of the following oxide additives: MgO, CaO, BeO, BaO, SrO, La 2 O 3 , CeO 2 , Pr 2 O 3 , Nd 2 O 3 , SmO 2 , Na 2 O, K 2 O, Cs 2 O, Rb 2 O, and ZrO 2 , pre-calcinated between 200 and 900 0 C. Preferentially, these catalyzers are calcinated between 300 and 700 0 C.
  • the catalyzers may be under the form of powder, or granulates or extrudades with different formats.
  • the process of transesterification on heterogeneous 5 catalyzers may be operated in batches, in continuous reactor of the tank type with mixture, as well as in fixed-bed reactors.
  • the spatial time in relation to the vegetable oil is 5 to 1000 min, being preferentially,

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé de transestérification de mono-, di et triglycérides présents dans des huiles végétales et des graisses animales, lesquels sont transestérifiés au moyen d'alcool constitués de 1 à 3 atomes de carbones au moyen de catalyseurs hétérogènes solides de base, ceux-ci étant les produits de la réaction utilisée comme combustible ou additif de combustible, comme solvants, comme intermédiaires de tensioactifs ou comme détergeants.
PCT/BR2006/000174 2005-09-01 2006-09-01 Procede catalytique destine a la transesterification d'huiles vegetales et de graisses au moyen de catalyseurs solides de base WO2007025360A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BRPI0504759-5 2005-09-01
BRPI0504759-5A BRPI0504759A (pt) 2005-09-01 2005-09-01 processo catalìtico para transesterificação de óleos vegetais e gorduras utilizando-se catalisadores sólidos básicos

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Publication Number Publication Date
WO2007025360A2 true WO2007025360A2 (fr) 2007-03-08
WO2007025360A3 WO2007025360A3 (fr) 2007-05-18

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009138298A1 (fr) * 2008-05-16 2009-11-19 Biocompany S.R.L. Procédé de préparation de biodiesel
DE102008036295A1 (de) 2008-08-04 2010-02-11 Bayer Technology Services Gmbh Katalysatorzusammensetzung zur Umesterung
ITNA20090024A1 (it) * 2009-05-08 2010-11-09 Eurochem Engineering S R L Uso di reattori innovativi per reazioni multifasiche liquido-liquido.
EP2305784A1 (fr) * 2009-10-02 2011-04-06 Green Finance AG Procédé et dispositif de fabrication continue d'alkyl-ester d'acides gras élevés
WO2013072664A1 (fr) 2011-11-17 2013-05-23 Davy Process Technology Limited Procédé de production d'alcools gras à partir d'acides gras
US8685881B2 (en) 2008-11-21 2014-04-01 Rohm And Haas Company Catalyst for transesterification process
KR101459334B1 (ko) * 2013-12-04 2014-11-10 희성촉매 주식회사 지방산 알킬 에스테르 제조용 촉매
US9212114B2 (en) 2012-10-09 2015-12-15 Johnson Matthey Davy Technologies Limited Process for the production of a fatty alcohol from a fatty acid
US9528059B2 (en) 2011-06-21 2016-12-27 W. R. Grace & Co.-Conn. Catalytic purification of fatty acid alkyl esters used in fuels
CN106471457A (zh) * 2014-09-26 2017-03-01 深圳市汇顶科技股份有限公司 指纹传感器
US10184085B2 (en) 2014-06-09 2019-01-22 W. R. Grace & Co.-Conn Method for catalytic deoxygenation of natural oils and greases
US10239812B2 (en) 2017-04-27 2019-03-26 Sartec Corporation Systems and methods for synthesis of phenolics and ketones
US10544381B2 (en) 2018-02-07 2020-01-28 Sartec Corporation Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid
US10696923B2 (en) 2018-02-07 2020-06-30 Sartec Corporation Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9102877B2 (en) 2008-11-12 2015-08-11 Sartec Corporation Systems and methods for producing fuels from biomass

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT386222B (de) * 1986-09-02 1988-07-25 Hans Dr Junek Verfahren und vorrichtung zur herstellung eines als kraft- bzw. brennstoff geeigneten fettsaeureestergemisches
AT388743B (de) * 1986-09-02 1989-08-25 Mittelbach Martin Verfahren zur herstellung eines fettsaeureestergemisches aus abfallfetten bzw. oelen und verwendung dieses gemisches als kraftbzw. brennstoff
AT394571B (de) * 1991-01-10 1992-05-11 Wimmer Theodor Verfahren zur herstellung von fettsaeureestern kurzkettiger alkohole
WO1998056747A1 (fr) * 1997-06-10 1998-12-17 Universidad Politecnica De Valencia Procede et catalyseurs pour l'obtention selective d'esters d'acides gras
ES2124166A1 (es) * 1996-05-16 1999-01-16 Univ Politecnica De Valencia Y Procedimiento y catalizadores para la obtencion selectiva de esteres de acidos grasos.
EP1126011A2 (fr) * 2000-02-17 2001-08-22 Sumitomo Chemical Company, Limited Procédé de préparation d'esters d'acide gras et combustible comprenant des esters d'acide gras
WO2006050925A1 (fr) * 2004-11-11 2006-05-18 Aser S.R.L. Procede permettant de produire desespere a partir d'huiles vegetales ou de graisses animales au moyen de catalyseurs heterogenes

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT386222B (de) * 1986-09-02 1988-07-25 Hans Dr Junek Verfahren und vorrichtung zur herstellung eines als kraft- bzw. brennstoff geeigneten fettsaeureestergemisches
AT388743B (de) * 1986-09-02 1989-08-25 Mittelbach Martin Verfahren zur herstellung eines fettsaeureestergemisches aus abfallfetten bzw. oelen und verwendung dieses gemisches als kraftbzw. brennstoff
AT394571B (de) * 1991-01-10 1992-05-11 Wimmer Theodor Verfahren zur herstellung von fettsaeureestern kurzkettiger alkohole
ES2124166A1 (es) * 1996-05-16 1999-01-16 Univ Politecnica De Valencia Y Procedimiento y catalizadores para la obtencion selectiva de esteres de acidos grasos.
WO1998056747A1 (fr) * 1997-06-10 1998-12-17 Universidad Politecnica De Valencia Procede et catalyseurs pour l'obtention selective d'esters d'acides gras
EP1126011A2 (fr) * 2000-02-17 2001-08-22 Sumitomo Chemical Company, Limited Procédé de préparation d'esters d'acide gras et combustible comprenant des esters d'acide gras
WO2006050925A1 (fr) * 2004-11-11 2006-05-18 Aser S.R.L. Procede permettant de produire desespere a partir d'huiles vegetales ou de graisses animales au moyen de catalyseurs heterogenes

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009138298A1 (fr) * 2008-05-16 2009-11-19 Biocompany S.R.L. Procédé de préparation de biodiesel
DE102008036295A1 (de) 2008-08-04 2010-02-11 Bayer Technology Services Gmbh Katalysatorzusammensetzung zur Umesterung
US8685881B2 (en) 2008-11-21 2014-04-01 Rohm And Haas Company Catalyst for transesterification process
ITNA20090024A1 (it) * 2009-05-08 2010-11-09 Eurochem Engineering S R L Uso di reattori innovativi per reazioni multifasiche liquido-liquido.
EP2305784A1 (fr) * 2009-10-02 2011-04-06 Green Finance AG Procédé et dispositif de fabrication continue d'alkyl-ester d'acides gras élevés
US9528059B2 (en) 2011-06-21 2016-12-27 W. R. Grace & Co.-Conn. Catalytic purification of fatty acid alkyl esters used in fuels
WO2013072664A1 (fr) 2011-11-17 2013-05-23 Davy Process Technology Limited Procédé de production d'alcools gras à partir d'acides gras
US9212114B2 (en) 2012-10-09 2015-12-15 Johnson Matthey Davy Technologies Limited Process for the production of a fatty alcohol from a fatty acid
KR101459334B1 (ko) * 2013-12-04 2014-11-10 희성촉매 주식회사 지방산 알킬 에스테르 제조용 촉매
US10184085B2 (en) 2014-06-09 2019-01-22 W. R. Grace & Co.-Conn Method for catalytic deoxygenation of natural oils and greases
CN106471457A (zh) * 2014-09-26 2017-03-01 深圳市汇顶科技股份有限公司 指纹传感器
CN106471457B (zh) * 2014-09-26 2020-07-17 深圳市汇顶科技股份有限公司 指纹传感器
US10239812B2 (en) 2017-04-27 2019-03-26 Sartec Corporation Systems and methods for synthesis of phenolics and ketones
US10544381B2 (en) 2018-02-07 2020-01-28 Sartec Corporation Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid
US10696923B2 (en) 2018-02-07 2020-06-30 Sartec Corporation Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids

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Publication number Publication date
BRPI0504759A (pt) 2007-06-12
WO2007025360A3 (fr) 2007-05-18

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