WO2002038529A1 - Procede de production d'esters d'acides gras d'alcools inferieurs - Google Patents

Procede de production d'esters d'acides gras d'alcools inferieurs Download PDF

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Publication number
WO2002038529A1
WO2002038529A1 PCT/AT2001/000348 AT0100348W WO0238529A1 WO 2002038529 A1 WO2002038529 A1 WO 2002038529A1 AT 0100348 W AT0100348 W AT 0100348W WO 0238529 A1 WO0238529 A1 WO 0238529A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
methanol
lower alcohols
phase
mixture
Prior art date
Application number
PCT/AT2001/000348
Other languages
German (de)
English (en)
Inventor
Theodor Wimmer
Original Assignee
Energea Umwelttechnologie Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Energea Umwelttechnologie Gmbh filed Critical Energea Umwelttechnologie Gmbh
Priority to AU2002213634A priority Critical patent/AU2002213634A1/en
Publication of WO2002038529A1 publication Critical patent/WO2002038529A1/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
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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
    • 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
    • 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 the preparation of fatty acid esters of lower alcohols with 1 to 4 carbon atoms, in particular methanol, suitable for use as diesel substitute fuels (biodiesel) by neutralizing the alkali-catalyzed transesterification of fatty acid glycerides with lower alcohols, in particular with methanol, as By-product of the heavy phase, the so-called glycerol phase, and by sulfuric acid-catalyzed esterification of the mixture of free fatty acids and fatty acid esters of lower alcohols, in particular methanol, obtained with the neutralization of the glycerol phase, with lower alcohols with 1-4 C atoms, preferably with methanol.
  • biodiesel Such methods are described for example in AT 397 510 B and EP 708 813 A.
  • These and most other processes use alkali metal hydrox.de or alcoholates as catalysts for the transesterification of fatty acid glycerides such as e.g. Rapeseed oil, sunflower oil or used edible fats with lower alcohols, especially with methanol, resulting in a by-product called glycerol phase, which contains, besides glycerol, a considerable proportion of alkali salts of fatty acids and fatty acid esters of the alcohol used for the transesterification.
  • the glycerol phase is economically worthless and represents a disposal product.
  • the fatty acids and fatty acid esters contained in it deteriorate the yield of biodiesel and thus the economy of a biodiesel plant.
  • carboxylic acid or Fatty acid esters can be esterified by esterifying the free acids with lower alcohols, preferably at the boiling point of the alcohols, in the presence of strong acids, such as hydrogen chloride, sulfuric acid or sulfonic acids.
  • a process for the esterification of a fatty acid / fatty acid ester mixture isolated from the glycerol phase is described in EP 708 813 A, the free fatty acids obtained from the neutralization of the glycerol phase being heated to 85 ° C. for two hours with methanol and concentrated sulfuric acid as catalyst, the content of free fatty acids decreases from approx. 50% to 12.5% and the entire mixture is fed to an alkali-catalyzed transesterification without further treatment and the catalyst acid is discharged via the transesterification process.
  • Concentrated sulfuric acid, benzene, p-toluene or methanesulfonic acid are mostly used as esterification catalysts.
  • One problem with the use of these acids is the recycling or disposal of the catalyst acid.
  • the acids either have to be regenerated, that is to say dewatered, in order to be able to be used again as catalysts, or they undergo, for example, an alkali-catalyzed transesterification process supplied or neutralized and get into the wastewater as non-biodegradable salts or accumulate as worthless by-products.
  • the object of the present invention is to provide an improved method for obtaining diesel substitute fuels
  • fatty acid esters of lower alcohols preferably methanol
  • glycerol phase obtained in the alkali-catalyzed transesterification of fatty acid glycerides with lower alcohols, which avoids the disadvantages mentioned and provides a fatty acid ester suitable as diesel fuel, and furthermore the lower alcohols contained in the glycerol phase are recovered and you get a raw glycerol with 60 to 90% glycerol.
  • phase containing the fatty acid esters of the lower alcohols in a manner known per se by treatment with alkali metal hydroxides, preferably potassium hydroxide solution, by washing with water and / or acids and evaporation of the excess lower alcohol, and that
  • the phase consisting of the excess lower alcohol, preferably methanol, sulfuric acid and water of reaction Neutralization of a further glycerol phase is used, the neutralized mixture being divided into a light phase consisting of free fatty acids, fatty acid esters of lower alcohols, preferably of methanol, and free lower alcohols, preferably methanol, and a heavier phase consisting of glycerol, the excess lower alcohol, preferably methanol, and Separates alkali sulfate.
  • the esterification of the mixture of free fatty acids and fatty acid esters of lower alcohols obtained from the neutralization of the glycerol phase is carried out at temperatures not above 50 ° C., preferably not above 40 ° C. and particularly preferably not above 35 ° C. This ensures an optimal manufacturing process, which is advantageously still energy-saving.
  • the concentrated sulfuric acid serving as catalyst is used in a concentration of 0.5-17% by mass, based on the mass of the fatty acid / fatty acid ester mixture.
  • the amount of sulfuric acid used is at most equal to or less than the amount required to neutralize the amount of alkali soaps contained in the glycerol phase. In the event that the amount of sulfuric acid used for the esterification is smaller than would be necessary to neutralize the glycerol phase, neutralization is carried out with additional sulfuric acid.
  • the lower alcohols with 1 to 4 carbon atoms are used in an amount of 15 to 200% by mass, based on the amount of the fatty acid / fatty acid ester mixture.
  • Ethanol, 1- and 2-propanol, 1-butanol, 2-butanol and isobutanol are also suitable as lower alcohols with 1 to 4 carbon atoms.
  • the esterification of the fatty acid / Fettklareestergemisches with 'the lower alcohols and which is concentrated sulfuric acid with vigorous stirring to generate the greatest possible turbulence in a period of 0.5 to 3 hours is thus accelerated by vigorous stirring, with the greatest possible turbulence, the degree of esterification being more than 95 percent after 0.5 to 3 hours.
  • methanol is used as the lower alcohol.
  • the phase consisting of the fatty acid esters of the lower alcohols, preferably of methanol, which still contains small amounts of free fatty acids is treated in a manner known per se with alkali metal hydroxides, preferably potassium hydroxide solution, and by washing with water and / or diluted acids and evaporation of the excess lower alcohol are cleaned or can be introduced into the washing process of a biodiesel plant.
  • alkali metal hydroxides preferably potassium hydroxide solution
  • the glycerol phases used are preferably those obtained in the transesterification of fatty acid glycerides with lower alcohols catalyzed by potassium hydroxide or potassium alcoholate.
  • the heavy phase resulting from the neutralization of the glycerol phase consisting of glycerol, excess lower alcohol and alkali sulfate, can be distilled to give lower alcohol which is returned to the esterification and a crude glycerol with 60-90 percent glycerol and in solid alkali sulfate, which in the case of potassium sulfate as Fertilizers used in agriculture can be refurbished.
  • a particular advantage of the process according to the invention can be seen in the fact that the sulfuric acid is used both as a catalyst for the esterification and subsequently for the neutralization of the glycerol phase, so that only one auxiliary substance is required for both processes, which is converted into an alkali metal sulfate, preferably potassium sulfate that can be used as a fertilizer in agriculture and that no biodegradable products such as sulfonic acids or their salts as waste products and that the esterification takes place in an energy-saving manner at moderate temperatures with high degrees of esterification of over 95%.
  • the process also meets the requirements.
  • Another advantage of the process according to the invention is that the amount of sulfuric acid required to neutralize the alkali metal salts of the fatty acids in the glycerol phase far exceeds the amount required to esterify the same amount of fatty acid, so that relatively high sulfuric acid concentrations can be used for the esterification, which at the low temperatures and times of 0.5-3 hours cause a high degree of esterification.
  • ester phase (108 grams) is mixed with 0.35 grams of a 50 percent potassium hydroxide solution and stirred for 2 minutes. After the stirrer has been switched off, the mixture separates into a phase which is 5 grams heavier and consists of the potassium salts of rapeseed fatty acids, methanol and water and in 103 grams of a lighter ester phase.
  • the ester phase is then washed first with water and then with dilute sulfuric acid and the excess methanol is removed in a rotary evaporator.
  • the rapeseed fatty acid methyl ester thus obtained contains less than 0.2% free fatty acids and meets all other requirements for usability as diesel fuel.
  • the phase (73.3 grams) consisting of 11.0 grams of sulfuric acid, 58.3 grams of methanol and 4 grams of water of reaction is separated off and allowed to flow into 300 grams of a glycerol phase which stems from a transesterification of rapeseed oil with methanol catalyzed by potassium hydroxide and has the following composition: 73 grams of potassium salts of rapeseed fatty acids 26 grams of rapeseed methyl ester 100 grams of glycerol 56 grams of methanol 45 grams of water
  • the neutralized mixture is filtered or centrifuged to separate solid potassium sulfate, after which the filtrate is dissolved in 100 grams of a lighter phase consisting of 65 grams of rapeseed fatty acids, 26 grams of rapeseed methyl ester and 9 grams of methanol and 246 grams of a heavier phase which contains glycerol, methanol and water , and which after evaporation of the methanol gives a crude glycerol with at least 60% glycerol.
  • a lighter phase consisting of 65 grams of rapeseed fatty acids, 26 grams of rapeseed methyl ester and 9 grams of methanol and 246 grams of a heavier phase which contains glycerol, methanol and water , and which after evaporation of the methanol gives a crude glycerol with at least 60% glycerol.
  • a lighter phase consisting of 65 grams of rapeseed fatty acids, 26 grams of rapeseed methyl este
  • reaction mixture 100 grams of a mixture consisting of 40% fatty acids, 52% fatty acid hylester and 8% methanol are stirred intensively with 120 grams of methanol and 2.8 grams of concentrated sulfuric acid for 2 hours at a temperature of 50 ° C with a magnetic stirrer. After switching off the stirrer, the reaction mixture separates into 102 grams of an ester phase consisting of 93.6 grams of fatty acid methyl ester, 0.4 grams of free fatty acids and 8 grams of methanol, and into 120.8 grams of a phase consisting of 2.7 grams of sulfuric acid, 2. 5 grams of water of reaction and 115 grams of methanol.
  • ester phase (102 grams) is mixed with 0.30 grams of a 30 percent solution of potassium hydroxide in methanol, stirred for 2 minutes, and proceed as in Example 1).
  • the fatty acid methyl ester thus obtained contains 0.08% free fatty acids.
  • Deep-frying oil with methanol comes from and has the following composition:
  • the neutralized mixture is filtered or centrifuged to separate solid potassium sulfate, after which the filtrate is in 100 grams of a lighter phase consisting of 40 grams of fatty acids, 52 grams of fatty acid methyl ester and 8 grams of methanol and 350 grams of a heavy phase containing glycerin methanol and water.
  • the lighter phase is fed to a further esterification as described at the beginning in this example.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production d'esters d'acides gras d'alcools inférieurs, notamment de méthanol, à partir de la phase glycérine qui résulte de la transestérification catalysée par voie basique de glycérides d'acides gras, notamment avec du méthanol. Les acides gras formés lors de la neutralisation de la phase glycérine sont estérifiés avec des alcools inférieurs, de préférence avec du méthanol et de l'acide sulfurique concentré. La phase obtenue après la séparation des phases du mélange de transestérification, constituée d'acide sulfurique, de méthanol et d'eau, est utilisé pour la neutralisation de la phase glycérine.
PCT/AT2001/000348 2000-11-08 2001-11-07 Procede de production d'esters d'acides gras d'alcools inferieurs WO2002038529A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002213634A AU2002213634A1 (en) 2000-11-08 2001-11-07 Method for the production of fatty acid esters of lower alcohols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AT0188700A AT410443B (de) 2000-11-08 2000-11-08 Verfahren zur herstellung von fettsäureestern niederer alkohole
ATA1887/00 2000-11-08

Publications (1)

Publication Number Publication Date
WO2002038529A1 true WO2002038529A1 (fr) 2002-05-16

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003087278A1 (fr) * 2002-04-12 2003-10-23 Energea Umwelttechnologie Gmbh Procede et installation d'esterification d'acides gras
US6822105B1 (en) 2003-08-12 2004-11-23 Stepan Company Method of making alkyl esters using glycerin
US6890451B2 (en) * 2003-09-23 2005-05-10 Richard Sapienza Environmentally benign anti-icing or deicing fluids employing triglyceride processing by-products
US7045100B2 (en) 1997-11-24 2006-05-16 Energea Unwelttechnologie Gmbh Method for producing fatty acid methyl ester and equipment for realizing the same
US7806945B2 (en) 2003-01-27 2010-10-05 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US7871448B2 (en) 2003-01-27 2011-01-18 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
CN101955850A (zh) * 2010-09-28 2011-01-26 上海绿铭环保科技股份有限公司 酸化油生产生物柴油的复合酸催化剂及生物柴油的生产方法
US8088183B2 (en) 2003-01-27 2012-01-03 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US8313667B2 (en) 2003-09-23 2012-11-20 Mli Associates, L.L.C. Environmentally benign anti-icing or deicing fluids employing triglyceride processing by-products
US9725397B2 (en) 2003-01-27 2017-08-08 REG Seneca, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
EP2358851B2 (fr) † 2008-11-17 2018-01-10 Basf Se Utilisation de l'acide méthanesulfonique pour la fabrication d'esters d'acide gras
US9957464B2 (en) 2013-06-11 2018-05-01 Renewable Energy Group, Inc. Methods and devices for producing biodiesel and products obtained therefrom

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT510636B1 (de) 2010-10-28 2016-11-15 Wimmer Theodor Verfahren zur herstellung von fettsäureestern niederer alkohole

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB612667A (en) * 1945-05-29 1948-11-16 Unilever Ltd Improvements in or relating to methods of alcoholysis of low grade fatty materials
EP0708813A1 (fr) * 1993-07-14 1996-05-01 Vogel & Noot Industrieanlagen Procede de preparation d'esters d'alkyle d'acide gras

Family Cites Families (5)

* 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
AT387399B (de) * 1987-04-03 1989-01-10 Gaskoks Vertrieb Ges Mit Besch Verfahren und vorrichtung zur herstellung von fettsaeureestern und deren verwendung
AT392977B (de) * 1989-10-13 1991-07-25 Wimmer Theodor Verfahren zur aufbereitung der bei der umesterung von fetten und oelen mit niederen alkoholen anfallenden glycerinphase
AT394374B (de) * 1990-06-29 1992-03-25 Wimmer Theodor Verfahren zur herstellung von fettsaeureestern niederer alkohole
AT397510B (de) * 1991-11-06 1994-04-25 Wimmer Theodor Verfahren zur herstellung von fettsäureestern kurzkettiger alkohole

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB612667A (en) * 1945-05-29 1948-11-16 Unilever Ltd Improvements in or relating to methods of alcoholysis of low grade fatty materials
EP0708813A1 (fr) * 1993-07-14 1996-05-01 Vogel & Noot Industrieanlagen Procede de preparation d'esters d'alkyle d'acide gras

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7045100B2 (en) 1997-11-24 2006-05-16 Energea Unwelttechnologie Gmbh Method for producing fatty acid methyl ester and equipment for realizing the same
WO2003087278A1 (fr) * 2002-04-12 2003-10-23 Energea Umwelttechnologie Gmbh Procede et installation d'esterification d'acides gras
EA007630B1 (ru) * 2002-04-12 2006-12-29 Энергеа Умвельттехнологи Гмбх Способ и установка для этерификации жирных кислот
US7256301B2 (en) 2002-04-12 2007-08-14 Energea Umwelttechnologie Gmbh Method and system for the esterification of fatty acids
US8088183B2 (en) 2003-01-27 2012-01-03 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US9725397B2 (en) 2003-01-27 2017-08-08 REG Seneca, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
US8728177B2 (en) 2003-01-27 2014-05-20 Seneca Landlord, L.L.C. Production of biodiesel and glycerin from high free fatty acid feedstocks
US7806945B2 (en) 2003-01-27 2010-10-05 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US7871448B2 (en) 2003-01-27 2011-01-18 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US7087771B2 (en) 2003-08-12 2006-08-08 Biosource America, Inc. Method of making alkyl esters using glycerin
US6822105B1 (en) 2003-08-12 2004-11-23 Stepan Company Method of making alkyl esters using glycerin
US8313667B2 (en) 2003-09-23 2012-11-20 Mli Associates, L.L.C. Environmentally benign anti-icing or deicing fluids employing triglyceride processing by-products
US8377328B2 (en) 2003-09-23 2013-02-19 Mli Associates, L.L.C. Environmentally benign anti-icing or deicing fluids
US6890451B2 (en) * 2003-09-23 2005-05-10 Richard Sapienza Environmentally benign anti-icing or deicing fluids employing triglyceride processing by-products
EP2358851B2 (fr) † 2008-11-17 2018-01-10 Basf Se Utilisation de l'acide méthanesulfonique pour la fabrication d'esters d'acide gras
CN101955850A (zh) * 2010-09-28 2011-01-26 上海绿铭环保科技股份有限公司 酸化油生产生物柴油的复合酸催化剂及生物柴油的生产方法
US9957464B2 (en) 2013-06-11 2018-05-01 Renewable Energy Group, Inc. Methods and devices for producing biodiesel and products obtained therefrom
US10450533B2 (en) 2013-06-11 2019-10-22 Renewable Energy Group, Inc. Methods and devices for producing biodiesel and products obtained therefrom

Also Published As

Publication number Publication date
AT410443B (de) 2003-04-25
AU2002213634A1 (en) 2002-05-21
ATA18872000A (de) 2002-09-15

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