EP2262880A2 - Process for deacidification of high acidity vegetable oils and used frying oils as biodiesel feedstock - Google Patents

Process for deacidification of high acidity vegetable oils and used frying oils as biodiesel feedstock

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Publication number
EP2262880A2
EP2262880A2 EP09717468A EP09717468A EP2262880A2 EP 2262880 A2 EP2262880 A2 EP 2262880A2 EP 09717468 A EP09717468 A EP 09717468A EP 09717468 A EP09717468 A EP 09717468A EP 2262880 A2 EP2262880 A2 EP 2262880A2
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EP
European Patent Office
Prior art keywords
methanol
extraction
phase
lime
oils
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP09717468A
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German (de)
French (fr)
Inventor
Zeynep Selma Turkay
Hale Gurbuz
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Individual
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Individual
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Publication of EP2262880A2 publication Critical patent/EP2262880A2/en
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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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/006—Refining fats or fatty oils by extraction
    • 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
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
    • 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

  • Present invention relates to the removal of the free fatty acids from high acidity oils or used frying oils which is going to be used for the production of biodiesel.
  • Biodiesel which contains fatty acid methyl ester in a minimum amount of 96.5 % by weight, is produced mainly from homogeneous alkali catalyzed transesterification reaction of animal and vegetable fats and oils with methanol.
  • the feedstocks should meet some requirements for the high reaction efficiency. The most important requirement is that the free fatty acid (FFA) content of fats and oils should be less than 0.5 %. Otherwise, the free fatty acids react with the alkali catalyst to produce soap, which causes either loss of catalyst or difficulties for the separation of the ester and glycerine phases after the reaction. Water formation through the soap reaction causes serious problems such as loss of the catalyst activity or hydrolysis of both triglycerides and methyl esters. For this reason a pretreatment step is required for deacidification of feedstock before transesterification reaction (Mittelbach and Remschmidt, 2004).
  • the process of neutralization of free fatty acids with aqueous sodium hydroxide solution is widely used for the deacidification of crude oils and fats for edible and technical purposes. This process can be applied to oils and fats containing FFA up to 8-10 %. For oils and fats containing more FFA, deacidification process can be performed only with the high neutral oil losses due the formation of high amount of soap or it could not be possible to separate the soap phase from the oil.
  • numerous of processes can be used such as distilation (physical refining), miscella refining, re-esterification with glycerol or liquid-liquid extraction (solvent extraction) processes (Bhosle and Subramanian, 2005).
  • Deacidification by liquid-liquid extraction for the removal of free fatty acids from oils and fats is based on the different solubility of triglycerides and fatty acids in organic solvents, such as methanol, ethanol or aceton.
  • Operation conditions of a deacidification process such as the kind and the amount of solvent, temperature and the number of stages of the countercurrent or crosscurrent extraction systems for the removal of the desired amount of free fatty acids can be calculated using phase diagrams of three components systems, namely neutral oil (triglycerid)-fatty acid-solvent (Rius and Martinez-Moreno, 1948; Rigamonti et a/., 1951; Batista et a/., 1999; Gongalves et a/., 2004; Rodrigues et al.,2007).
  • Methanol in the extract phase consisting the essential part of the solvent fed in the column is also evaporated and is recycled to the extraction column together with the methanol recovered from the raffinate phase.
  • the flow diagram of this conventional deacidification process using methanol extraction is shown in Figure !
  • One object of the present invention is to apply a liquid-liquid extraction process to the high acidity vegetable oils and used frying oils with methanol to obtain a deacidified oil which can be used as biodiesel feedstock.
  • Another object of the present invention is to react the extract phase with lime (calcium oxide), slaked lime (calcium hydroxide), or dolomitic lime to precipitate the free fatty acids as calcium soaps,
  • Yet another object of the present invention is to feed back the regenerated methanol phase to the extraction process after the filtration of solid soaps.
  • the process of the invention consists of the following steps:
  • Figure 1 the flow diagram of the conventional deacidification process of oils and fats with methanol extraction is shown.
  • the recovery of methanol from the extract phases obtained after crosscurrent or countercurrent extraction is performed by the precipitation of free fatty acids dissolved in this phase with lime as calcium soap and by separating them through filtration.
  • Extraction In this operation, feedstock is extracted with methanol, preferably 100% methanol, at ambient temperature in batch or continuous, crosscurrent or countercurrent extraction apparatus wherein the number of stage and the amount of solvent is used according to the desired degree of deacidification. If the feedstock contains solid impurities, a pre-filtration is performed. 2. Feeding of the raffinate phase to biodiesel production: After the extraction, the raffinate phase which contains 8-10% methanol is sent to the transesterification reaction after completing the amount of methanol required for transesterification and adding the required kind and amount of catalyst.
  • methanol preferably 100% methanol
  • the extract phase which has a composition depending on the feedstock and the amount of solvent, and usually contains 90-95% methanol, is reacted with preferably powder calcium hydroxide in a reactor, preferably mixing under reflux at the temperature approximetly 55-60 0 C, according the following equation.
  • the reactor comprises a reflux condenser and a stirrer.
  • composition of the extract phase (E3) has been determined. Additionally, the qualitative analysis of compositions of three extract phases and also of the used frying oil has been performed by using thin layer chromatography as shown in Figure 3, where MG: monoglyceride, DG: diglyceride, FFA: free fatty acid, TG: triglyceride.
  • anhydrous methanol as solvent in liquid-liquid extraction.
  • aqueous methanol with water content up to 10% can be used in the extraction.
  • the water content of the raffinate phase after extraction is higher than the water content required in transesterification reaction (500 ppm), it can be used in biodiesel production after removing its solvent hence the water.
  • water is formed in the regenerated extract phase after the reaction with calcium hydroxide. Based on the reaction stoichiometry, the amount of water can be calculated as follows:

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

Abstract

This invention relates to a process to be used for deacidification of high FFA vegetable oils or used frying oils for using same in biodiesel production as feedstock.

Description

PROCESS FOR DEACIDIFICATION OF HIGH ACIDITY VEGETABLE OILS AND USED FRYING OILS AS BIODIESEL FEEDSTOCK
Technical Field
Present invention relates to the removal of the free fatty acids from high acidity oils or used frying oils which is going to be used for the production of biodiesel.
Background of the Invention
Biodiesel,which contains fatty acid methyl ester in a minimum amount of 96.5 % by weight, is produced mainly from homogeneous alkali catalyzed transesterification reaction of animal and vegetable fats and oils with methanol. The feedstocks should meet some requirements for the high reaction efficiency. The most important requirement is that the free fatty acid (FFA) content of fats and oils should be less than 0.5 %. Otherwise, the free fatty acids react with the alkali catalyst to produce soap, which causes either loss of catalyst or difficulties for the separation of the ester and glycerine phases after the reaction. Water formation through the soap reaction causes serious problems such as loss of the catalyst activity or hydrolysis of both triglycerides and methyl esters. For this reason a pretreatment step is required for deacidification of feedstock before transesterification reaction (Mittelbach and Remschmidt, 2004).
The process of neutralization of free fatty acids with aqueous sodium hydroxide solution is widely used for the deacidification of crude oils and fats for edible and technical purposes. This process can be applied to oils and fats containing FFA up to 8-10 %. For oils and fats containing more FFA, deacidification process can be performed only with the high neutral oil losses due the formation of high amount of soap or it could not be possible to separate the soap phase from the oil. For the deacidification of high acidity oils, numerous of processes can be used such as distilation (physical refining), miscella refining, re-esterification with glycerol or liquid-liquid extraction (solvent extraction) processes (Bhosle and Subramanian, 2005). Deacidification by liquid-liquid extraction for the removal of free fatty acids from oils and fats is based on the different solubility of triglycerides and fatty acids in organic solvents, such as methanol, ethanol or aceton. Operation conditions of a deacidification process, such as the kind and the amount of solvent, temperature and the number of stages of the countercurrent or crosscurrent extraction systems for the removal of the desired amount of free fatty acids can be calculated using phase diagrams of three components systems, namely neutral oil (triglycerid)-fatty acid-solvent (Rius and Martinez-Moreno, 1948; Rigamonti et a/., 1951; Batista et a/., 1999; Gongalves et a/., 2004; Rodrigues et al.,2007).
Industrial applications of the solvent extraction are usually carried out continuously at the countercurrent extraction towers. As an example, for the oil- fatty acid-methanol system, high acidity oil is fed at the top of the column, and methanol is fed at the bottom. While the raffinate phase which consists of the oil having desired FFA content and methanol dissolved in this oil is taken from the bottom of the column, the extract phase, which mainly consists of methanol and fatty acids dissolved in methanol and some amounts of triglycerides, diglycerides, monoglycerides, oxidized and polymerized compounds depending on the initial composition of oil, is withdrawn from the top. Methanol in the raffinate phase is evaporated and refined oil (raffinate) having low acidity is obtained. Methanol in the extract phase consisting the essential part of the solvent fed in the column is also evaporated and is recycled to the extraction column together with the methanol recovered from the raffinate phase. The flow diagram of this conventional deacidification process using methanol extraction is shown in Figure !
There are numbers of study in the art for deacidification of oils and fats with liquid-liquid extraction using various solvents, such as methanol (100 % or containing water in different ratio), ethanol, aceton, diethylene glycol or furfural (Andersen, 1962). In most of these studies, solvent recoveries from extract and raffinate phases have been performed using evaporation operation after the extraction (Drescher et al, 1999). In two studies investigating deacidifications of soybean and rice bran oils, methanol recoveries have been carried out by membrane technology (nanofltration) from the extract phases after liquid-liquid extractions of oils with methanol (Raman et al., 1996, Kale et a/., 1999 ).
Disclosure of Invention
One object of the present invention is to apply a liquid-liquid extraction process to the high acidity vegetable oils and used frying oils with methanol to obtain a deacidified oil which can be used as biodiesel feedstock.
Another object of the present invention is to react the extract phase with lime (calcium oxide), slaked lime (calcium hydroxide), or dolomitic lime to precipitate the free fatty acids as calcium soaps,
Yet another object of the present invention is to feed back the regenerated methanol phase to the extraction process after the filtration of solid soaps.
To achieve the above-mentioned objects, the process of the invention consists of the following steps:
- extracting the high acidity vegetable oil or used frying oil with methanol in a liquid-liquid extraction apparatus,
- optionally pre-filtrating the feedstock before extraction,
- forwarding the raffinate phase containing methanol to the transesterification reaction without subjecting thereof evaporation operation after the extraction,
- reacting the extract phase obtained from the said extraction with a lime,
- separating the lime soaps occurred at the above reaction from the methanol phase,
- forwarding the obtained methanol phase to the extraction process again. - adding supplementary fresh methanol to the methanol phase before forwarding thereof to the extraction again. Brief Description of Figures
In Figure 1 the flow diagram of the conventional deacidification process of oils and fats with methanol extraction is shown.
In Figure 2 the flow diagram of the process of invention for the production of biodiesel feedstock from high acidity oils and used frying oils is shown.
In Figure 3 thin layer chromatogram which shows qualitative composition of the extract phases is given.
Detailed Disclosure of the Invention
In the process of the invention wherein production of biodiesel feedstock from high acidity vegetable oils or used frying oils, the recovery of methanol from the extract phases obtained after crosscurrent or countercurrent extraction is performed by the precipitation of free fatty acids dissolved in this phase with lime as calcium soap and by separating them through filtration.
The process according to the invention illustrated in Figure 2, consists mainly the following steps:
1. Extraction: In this operation, feedstock is extracted with methanol, preferably 100% methanol, at ambient temperature in batch or continuous, crosscurrent or countercurrent extraction apparatus wherein the number of stage and the amount of solvent is used according to the desired degree of deacidification. If the feedstock contains solid impurities, a pre-filtration is performed. 2. Feeding of the raffinate phase to biodiesel production: After the extraction, the raffinate phase which contains 8-10% methanol is sent to the transesterification reaction after completing the amount of methanol required for transesterification and adding the required kind and amount of catalyst.
3. Lime treatment of extract phase: The extract phase, which has a composition depending on the feedstock and the amount of solvent, and usually contains 90-95% methanol, is reacted with preferably powder calcium hydroxide in a reactor, preferably mixing under reflux at the temperature approximetly 55-60 0C, according the following equation.
2 RCOOH + Ca(OH)2 ( RCOO)2 Ca + 2 H2O (1 )
Instead of calcium hydroxide or calcium oxide, another type of lime, for example dolomitic lime can be used in the lime treatment operation according to the invention. The reactor comprises a reflux condenser and a stirrer.
4. Filtration of calcium soaps: After the mixing is terminated at the end of the reaction calcium soaps precipitate immediately and a clear methanol solution is obtained at supernatant. After cooling to the room temperature the mixture is filtered and the clear methanol phase is sent back to the extractor for reusing. For a new extraction operation fresh methanol is added to this methanol phase to complete the amount dissolved in the raffinate phase and hold by calcium soaps. Therefore, the amount of makeup methanol is equal to the amount of methanol that passed into the raffinate phase plus retained by the calcium soaps under the given conditions of extraction
EXAMPLE: In order to prove the repeated usability of the extract phase after treatment with calcium hydroxide, one volume of used frying oil (UFO) containing 7.1 %wt of free fatty acid has been extracted with two volumes of methanol (JT. Baker®) in a single step. Extract and raffinate phases have been separated. After determining its composition, the extract phase (E1) has been reacted with calcium hydroxide (Merck®) by stirring with a magnetic stirrer under reflux at 65°C. The composition of the methanol phase (E2), which has been separated from the reaction mixture by filtration, has been determined and it has been reused in the extraction of a new part of used frying oil by applying the same conditions as with the first extraction. The composition of the extract phase (E3) has been determined. Additionally, the qualitative analysis of compositions of three extract phases and also of the used frying oil has been performed by using thin layer chromatography as shown in Figure 3, where MG: monoglyceride, DG: diglyceride, FFA: free fatty acid, TG: triglyceride.
In Table 1 below, the compositions of three extract phases are given. The total dissolved material in the extract phases has been determined by evaporation, whereas the free fatty acid content by alkali titration.
Table 1. Composition of the Extract Phases Before and After the Treatment with Lime
Extraction conditions: % FFA content of UFO=7.1 MeOH/UFO=2:1 (vol.)
According to the result given in Table 1 , (18.2-0.27)χ100/18.2= 98.5% of free fatty acids in the first extract phase has been removed by the reaction of extract phase with lime. After using the regenerated extract phase for another new extraction step of used frying oil, both the amount of total dissolved material and free fatty acids has increased in the extract phase (E3). The reason of this increase is the increase of pH from 5.5 to 7.0 after the reaction of extract phase with lime.
The examination of the thin layer chromatogram in Figure 3 in the light of the results given in Table 1 indicates that the amount of free fatty acids in the regenerated extract phase (E2) decreases drastically. It is clearly seen that the composition of extract phase (E3) obtained from the extraction of used frying oil with the regenerated extract phase is not quite different from the composition of the extract phase (E1) obtained from extraction with fresh methanol. The same chromatogram shows the presence of small amount of free fatty acids and diglycerides in addition to triglycerides as dissolved material in the extract phase after regeneration with lime. Since the regenerated extract phase will dissolve less triglyceride, decrease in the loss of triglyceride during the deacidification is an inherent result in the case of using this phase for a new extraction.
In the invented process, depending on the free fatty acid content and the amount and type of other impurities, it is preferred to use anhydrous methanol as solvent in liquid-liquid extraction. However, if the amount and the type of free fatty acids and other impurities in initial raw material are not suitable for the formation of two phases, aqueous methanol with water content up to 10% can be used in the extraction. In this case, if the water content of the raffinate phase after extraction is higher than the water content required in transesterification reaction (500 ppm), it can be used in biodiesel production after removing its solvent hence the water.
According to the reaction equation (1), water is formed in the regenerated extract phase after the reaction with calcium hydroxide. Based on the reaction stoichiometry, the amount of water can be calculated as follows:
Amount of formed water =0.064 x Amount of reacted free fatty acid From the calculation for the experiment, for which the conditions and the results are given in Table 1 , the amount of water formed in the reaction is found to be 0.064 x (18.2-0.27) = 1.15 g/L.
According to this calculation, when anhydrous methanol (100%) is used in the first extraction, methanol concentration of the extract phase decreases to 98.85% after the reaction with lime due to the water formed in the reaction. Furthermore, the water content of the extract phase increases more if the raw oil entering to the extraction contains water. Therefore, when the water content reaches to the allowable limit value (5%) during the process, dehydration should be applied to the extract phase.

Claims

1. A deacidification process for high acidity vegetable oils or used frying oils for using as raw material in biodiesel production, containing the following steps of:
- extracting the high acidity vegetable oil or used frying oil with methanol in a liquid-liquid extraction apparatus,
- optionally pre-filtrating the feedstock before extraction, - forwarding the raffinate phase containing methanol to the transesterification reaction without subjecting thereof evaporation operation after the extraction,
- reacting the extract phase obtained from the said extraction with a lime,
- separating the lime soaps occurred at the above reaction from the methanol phase,
- forwarding the obtained methanol phase to the extraction process again.
- adding supplementary fresh methanol to the methanol phase before forwarding thereof to the extraction again.
2. Process according to claim 1 wherein extraction apparatus is of the type operated either in cocurrent or countercurrent mode.
3. Process according to claim 1 wherein optional pre-filtration is applied when the raw material contains solid impurities.
4. Process according to claim 1 wherein methanol used to extract the raw material is either pure (anhydrous) methanol or aqueous methanol having water.
5. Process according to claim 1 wherein lime is selected optionally from a group containing calcium oxide, calcium hydroxide or dolomitic lime.
6. Process according to claim 1 wherein the reaction of extract phase with lime is performed in a reactor having a reflux condenser and a stirrer.
7. Process according to claim 1 in which the amount of makeup methanol is equal to the amount of methanol that passed into the raffinate phase plus retained by the calcium soaps under the given conditions of extraction.
EP09717468A 2008-03-07 2009-02-17 Process for deacidification of high acidity vegetable oils and used frying oils as biodiesel feedstock Withdrawn EP2262880A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2008/01480A TR200801480A2 (en) 2008-03-07 2008-03-07 A process for the removal of acid from high acid vegetable oils and frying oils for use in biodiesel production.
PCT/TR2009/000026 WO2009110854A2 (en) 2008-03-07 2009-02-17 Process for deacidification of high acidity vegetable oils and used frying oils as biodiesel feedstock

Publications (1)

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EP2262880A2 true EP2262880A2 (en) 2010-12-22

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EP09717468A Withdrawn EP2262880A2 (en) 2008-03-07 2009-02-17 Process for deacidification of high acidity vegetable oils and used frying oils as biodiesel feedstock

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WO (1) WO2009110854A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2395964B1 (en) * 2011-07-27 2013-12-27 Consejo Superior De Investigaciones Cientificas (Csic) METHOD OF ELIMINATION OF CALCICO SOAPS AND PROCEDURE OF SYNTHESIS OF BIODIESEL FREE OF SOAPS USING CAO AS CATALYST
US10059905B2 (en) 2012-11-13 2018-08-28 Rrip, Llc Method to recover free fatty acids from fats and oils
CN103981026A (en) * 2014-06-12 2014-08-13 深圳市新宝环保能源科技有限公司 Method for lowering acid value of biodiesel

Citations (1)

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Publication number Priority date Publication date Assignee Title
US20050204612A1 (en) * 2002-09-20 2005-09-22 Joosten Connemann Method and device for producing biodiesel

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US1862037A (en) * 1929-12-04 1932-06-07 Schlenker Ernst Process for the separation of liquid and solid fatty acids
GB578751A (en) * 1942-10-17 1946-07-10 Colgate Palmolive Peet Co Process for the production of alkyl esters from fats and fatty oils
US3558679A (en) * 1967-09-22 1971-01-26 Laroche Navarron Lab Process for the extraction of the unsaponifiable fraction of vegetable oils
AUPN475095A0 (en) * 1995-08-11 1995-09-07 Hyam Myers Consulting Pty. Limited Removal of free fatty acids from oil and fats
DE10164274B4 (en) * 2001-12-27 2005-12-29 Energietechnik Leipzig Gmbh Process and device for the continuous extraction of free fatty acids, tocopherols and / or sterols from native oils and for transesterification of native oils
ITMI20060279A1 (en) * 2006-02-15 2007-08-16 Aser S R L PROCEDURE FOR DEACIDIFYING OILS AND GREASES

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US20050204612A1 (en) * 2002-09-20 2005-09-22 Joosten Connemann Method and device for producing biodiesel

Also Published As

Publication number Publication date
TR200801480A2 (en) 2009-09-23
WO2009110854A2 (en) 2009-09-11
WO2009110854A3 (en) 2009-12-30

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