EP2522712A1 - Verfahren zur Herstellung von Fettsäureniedrigalkylestern auf Basis von nicht-raffinierten Fetten und Ölen - Google Patents

Verfahren zur Herstellung von Fettsäureniedrigalkylestern auf Basis von nicht-raffinierten Fetten und Ölen Download PDF

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Publication number
EP2522712A1
EP2522712A1 EP11165962A EP11165962A EP2522712A1 EP 2522712 A1 EP2522712 A1 EP 2522712A1 EP 11165962 A EP11165962 A EP 11165962A EP 11165962 A EP11165962 A EP 11165962A EP 2522712 A1 EP2522712 A1 EP 2522712A1
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EP
European Patent Office
Prior art keywords
fraction
oil
transesterification
alkyl esters
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Withdrawn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
EP11165962A
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English (en)
French (fr)
Inventor
Horst Josten
Ewelina Sobierska
Adrian Chan
Truc Tran Anh
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Cognis IP Management GmbH
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Cognis IP Management 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 Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP11165962A priority Critical patent/EP2522712A1/de
Publication of EP2522712A1 publication Critical patent/EP2522712A1/de
Withdrawn legal-status Critical Current

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    • 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

Definitions

  • a major advantage of the low pressure transesterification technology is related to the lower processing costs, in particular lower energy consumption, lower alcohol excess, lower maintenance costs and lower investment costs, if compared to high pressure transesterification.
  • the high pressure transesterification has the advantage, that cheaper raw materials and waste fat streams can be converted.
  • the column internals are chosen from structured or dumped packing or trays depending on the solids and gum content of the crude oil. For example, in case of coconut or palm kernel oil structured packing is preferred due to low pressure drop. For oils with higher solids/gum content umbrella bubble cap trays are preferred due to lower pressure drop than for other tray types.
  • the height of the packings can be about 3 to about 8 and preferably about 4 to about 6 m.
  • the number of trays should be about 6 to about 18, preferably about 8 to about 14. Partial condensation of the fatty acid vapors is performed by a partial condenser (dephlegmator) or preferably by a direct condensation in a packing (5) with recirculation loop and external plate cooler (6).
  • Vapors leaving the partial condenser are condensed in the second condenser (7).
  • An additional feature of the invention is to install an additional packing (8) above the feed and to run the column with a small reflux of the first distillate in order to reduce the amount of glycerides in the fatty acid distillate. In this case an additional reboiler (9) is required to provide the heat of vaporization for the reflux stream.
  • the de-acidification column should be operated at a vacuum of about 2 to about 20 and preferably about 5 to about 10 mbar.
  • the crude oil feed should be heated to about 225 to about 280 and preferably about 245 to about 260 °C.
  • the stripping steam rate should be adjusted to about 1 to about 5, and preferably about 1 to about 2 % of the crude oil feed rate.
  • the resulting acid values of the de-acidified oils are between about 0.02 and about 1, preferably about 0.1 to about 0.5, the resulting water content between about 0.01 and about 0.1, preferably about 0.01 to about 0.03 %.
  • the alkyl esters, generated by the described two esterification procedures can be routed to the following step (c) or to an additional high pressure transesterification step.
  • Step c Low pressure transesterification of de-acidified crude oil
  • the low pressure transesterification can be performed in two stages at temperatures in the range of about 65 to about 90 °C.
  • the de-acidified and dried crude oil is mixed with the lower alcohol, preferably methanol, and catalyst, heated to reaction temperature and routed to a first reactor (14). After the first reaction stage the formed glycerol is separated from the reaction mixture by gravity. The reaction mixture is then fed to a second reactor (15) together with additional alcohol and catalyst.
  • Suitable equipments to perform the reactions are e.g. static mixers combined with tube reactors or mixer settlers as shown in Figure 1 . Mixer settlers are advantageous with regard of turndown ratios, since at lower feed rates the mixing efficiency is still good and the conversion even improved, while for tube reactors the mixing efficiency is reduced at lower flow rates. It is also possible to combine the elements, e.g. a mixer-settler with a tube reactor.
  • the reaction pressure is dependent on reaction temperature due to the vapor pressure of the alcohol and may range from about 1 to about 5 bar.
  • Alcohol:oil ratios are typically in the range of about 0.2 to about 0.35, preferably about 100 % in excess compared to stoichiometric consumption for the first reaction step, while for the second reaction step the ratio can be decreased by a factor of about 10.
  • Step d Methanol removal from methyl ester
  • the alcohol recovered from the alkyl ester phase has a water content of typically less than 0.2 %, so that the alcohol can be recycled to the transesterification without further separation of water.
  • Short chain alkyl esters evaporated together with the methanol are trapped by a condenser and routed back to the feed as recycle stream.
  • a final embodiment of the present invention is directed to equipment for conducting a process for obtaining fatty acid C 1 -C 4 alkyl esters from unrefined fats and oils comprising
  • coconut fatty acid distillate achieved from the de-acidification step described in example 1 was fed to a static mixer at a flow rate of 2.5 kg/hr, where it was continuously mixed with 1.0 kg/hr methanol.
  • the mixture was preheated to 100 °C via a preheater and subsequently fed to two reaction vessels filled with granular acidic ion exchange catalyst Lewatit K2641, each catalyst bed having a volume of 10 l.
  • the reaction mixture from the 1 st reaction was stripped from water and methanol under vacuum before pas-sing a 2 nd static mixer together with 0.3 kg of methanol and entering the 2 nd fixed bed reactor.
  • Measured AV after 1 st and 2 nd reaction stages were 18.6 and 0.98 respectively
  • the methyl ester phase from the first settler was fed to the second mixing chamber together with 0.5 kg/hr of a methanol/sodium methylate/water mixture, having the same composition like added to the first mixing stage. Additional glycerol generated by the transesterification reaction in the second mixing chamber was separated by gravity from the methyl ester in the second settling zone and both phases were taken continuously from the second settler.

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  • Chemical & Material Sciences (AREA)
  • General 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)
  • Fats And Perfumes (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP11165962A 2011-05-13 2011-05-13 Verfahren zur Herstellung von Fettsäureniedrigalkylestern auf Basis von nicht-raffinierten Fetten und Ölen Withdrawn EP2522712A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11165962A EP2522712A1 (de) 2011-05-13 2011-05-13 Verfahren zur Herstellung von Fettsäureniedrigalkylestern auf Basis von nicht-raffinierten Fetten und Ölen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP11165962A EP2522712A1 (de) 2011-05-13 2011-05-13 Verfahren zur Herstellung von Fettsäureniedrigalkylestern auf Basis von nicht-raffinierten Fetten und Ölen

Publications (1)

Publication Number Publication Date
EP2522712A1 true EP2522712A1 (de) 2012-11-14

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EP11165962A Withdrawn EP2522712A1 (de) 2011-05-13 2011-05-13 Verfahren zur Herstellung von Fettsäureniedrigalkylestern auf Basis von nicht-raffinierten Fetten und Ölen

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EP (1) EP2522712A1 (de)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007113530A2 (en) * 2006-03-31 2007-10-11 Greenergy Biofuels Limited Biodiesel production
EP1892232A1 (de) * 2006-08-21 2008-02-27 Desmet Ballestra Oleo s.p.a. Produktion von Estern aus Fettsäuren und Niedrigalkoholen
US20090294358A1 (en) 2007-10-30 2009-12-03 Bayer Technology Services Gmbh Process for heterogeneously catalysed esterfication of fatty acids
US20100205853A1 (en) * 2007-10-09 2010-08-19 Council Of Scientific & Industrial Research Process for the Preparation of Biodiesel from Vegetable Oils Containing High FFA
US20100249442A1 (en) * 2007-10-30 2010-09-30 Bayer Technology Sevices Gmbh Continuous method for the heterogenically catalyzed esterification of fatty acids
US20100298586A1 (en) * 2007-12-19 2010-11-25 Bayer Technology Services Gmbh Method for producing fatty acid alkyl esters

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007113530A2 (en) * 2006-03-31 2007-10-11 Greenergy Biofuels Limited Biodiesel production
EP1892232A1 (de) * 2006-08-21 2008-02-27 Desmet Ballestra Oleo s.p.a. Produktion von Estern aus Fettsäuren und Niedrigalkoholen
US20100205853A1 (en) * 2007-10-09 2010-08-19 Council Of Scientific & Industrial Research Process for the Preparation of Biodiesel from Vegetable Oils Containing High FFA
US20090294358A1 (en) 2007-10-30 2009-12-03 Bayer Technology Services Gmbh Process for heterogeneously catalysed esterfication of fatty acids
US20100249442A1 (en) * 2007-10-30 2010-09-30 Bayer Technology Sevices Gmbh Continuous method for the heterogenically catalyzed esterification of fatty acids
US20100298586A1 (en) * 2007-12-19 2010-11-25 Bayer Technology Services Gmbh Method for producing fatty acid alkyl esters

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