EP2522711A1 - Procédé pour l'obtention de produits oléochimiques ayant un contenu réduit en sous-produits - Google Patents

Procédé pour l'obtention de produits oléochimiques ayant un contenu réduit en sous-produits Download PDF

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Publication number
EP2522711A1
EP2522711A1 EP11165985A EP11165985A EP2522711A1 EP 2522711 A1 EP2522711 A1 EP 2522711A1 EP 11165985 A EP11165985 A EP 11165985A EP 11165985 A EP11165985 A EP 11165985A EP 2522711 A1 EP2522711 A1 EP 2522711A1
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EP
European Patent Office
Prior art keywords
oils
fats
distillate
fatty acids
oil
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EP11165985A
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German (de)
English (en)
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EP2522711B1 (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
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    • 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
    • C11B3/12—Refining fats or fatty oils by distillation
    • C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
    • 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

  • the present invention belongs to the area of oleochemicals and refers to an improved process for obtaining fatty acids, fatty acid alkyl esters and fatty alcohols with reduced content of ketones, aldehydes and phenols and their hydrogenation products.
  • EP 0127104 B1 discloses a process for making fatty acid esters of short-chain, aliphatic alcohols by catalytic transesterification of natural fats and/or oils containing free fatty acids (oil phase) with the corresponding alcohols, the oil phase is subjected to preliminary esterification with the alcohols in the presence of acidic esterification catalysts at temperatures no higher than 120 °C and under pressures of less than 5 bar and in the presence of a liquid entraining agent substantially immiscible with the oil phase, after which the reaction product is separated into an entraining agent phase containing the acidic catalyst and water of reaction and the treated oil phase.
  • the oil phase is then subjected to transesterification while the acidic catalyst-containing entraining agent phase is returned, after at least partial drying, to the preliminary esterification stage.
  • fats and/or oils with acid numbers of up to 60 can be processed in the preliminary esterification stage to give an oil phase having a low acid number.
  • EP 1092703 B1 (Cognis ) teaches the preparation of fatty acid methyl esters having an acid number of less than 0.1 comprises subjecting a fatty acid glyceride, having an acid number of 5 to 20, with methanol in a ratio of 0.4 to 0.7 % w/v to a two stage esterification process comprising a first high-pressure and a second low-pressure esterification
  • a first object of the present invention covers a process for obtaining fatty acids with reduced content of by-products, which is characterised in that
  • a second object of the present invention refers to a process for obtaining fatty acid alkyl esters with reduced content of by-products, which is characterised in that
  • a third object of the present invention is directed to a process for obtaining fatty alcohols with reduced content of by-products, which is characterised in that
  • the top fraction typically represents only 1, in particular about 0.5 % b.w. of the total mass of the distillation products (bottom product plus side streams) the amount of waste material compared to other processes is much smaller, what provides an additional economic advantage over the state of the art. Also, the first fatty acid distillate taken off as the side stream shows a seriously reduced content of by-products and thus represents also a valuable product, which can be combined with the bottom fraction of the de-acidified oils for transesterification or can be applied for other purposes.
  • the process according to the present invention can be applied to all kinds of vegetable oils, in particularly those oils showing an acid value typically of 1 to 20, but also higher.
  • suitable oils - without limitation - are palm oil, palm kernel oil, coconut oil, olive oil, sunflower oil, saflor oil, soy oil, line oil, rape oil, fish oil, lard oil, tallow and their mixtures.
  • the combined de-acidification and separation of impurities from crude fats or oils is preferably done under vacuum in a counter-current column with stripping steam as shown in Figure 1 .
  • the crude oil is pre-heated by economizers (1, 2) and pre-heater (3) and fed to the top of the column (4).
  • economizers (1, 2) and pre-heater (3) While trickling down the column free fatty acids and other low boiling impurities like aldehydes, ketones and phenols are stripped from the oil with stripping steam, which is introduced at the column bottom.
  • the stripped off fatty acids and impurities are condensed from the stripping steam in two steps while the de-acidified oil is taken from the column as bottom product.
  • the column internals can either be structured or dumped packing or trays depending on the solids or gum content of the crude oil.
  • coconut oil or palm kernel oil structured packing is preferred due to low pressure drop.
  • 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 packing can be about 3 to about 8, 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 vapours is typically performed by a partial condenser ("dephlegmator") or more preferably by a direct condensation in a packing (5) with recirculation loop and external plate cooler (6).
  • An additional feature of the invention is to install an additional packing (8) above the feed and run the column with a small reflux - about 1 to about 10 % of the distillate - of the first distillate in order to reduce the amount of glycerides in the fatty acid distillate.
  • 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, preferably about 5 to about 10 mbar.
  • the crude oil feed should be heated to about 225 to about 280, preferably about 245 to about 260 °C.
  • the stripping steam rate should be adjusted to about 1 to about 5 % w/w, while it is preferred to adjust the rate to about 1 to about 2 % w/w of the crude oil feed rate.
  • the resulting acid values of the de-acidified oils and fats are typically between about 0.02 and about 1 and preferably between about 0.1 and about 0.5, the resulting water content between about 0.01 and about 0.1, preferably between about 0.01 to about 0.03 %.
  • the second condensate can either be discarded as waste or be used as a low fatty acid quality for technical applications.
  • the first distillate of the de-acidification column contains mainly - which means about 50 to about 99 % b.w. - fatty acids, the rest being glycerides.
  • This stream can either directly be routed to high pressure transesterification or esterified and subsequently routed to a low or high pressure transesterification together with the bottom product from the column.
  • an alternative procedure is to replace the partial condensation shown in Figure 1 by a fractionation in a packed section in the top of the column (5) with refluxing and fractionating at least a part of the second quality fatty acid as shown in Figure 2 . Doing this the split of the low-boilers between the fatty acid qualities can substantially be improved.
  • reaction mixture leaving the transesterification step is then hydrogenated and the resulting fatty alcohol mixture is improved in quality compared to the processing of unrefined oils without the described de-acidification procedure.
  • These processes represent major operations in technical industry and are well known for one skilled in the art so that additional explanations are not necessary.
  • EP 0332971 B1 (Henkel ) referring to the transesterification of fatty acid lower alkyl esters and DE 4321837 A1 (Henkel ) disclosing the hydrogenation of methyl esters to fatty alcohols which is conducted in two fixed-bed reactors.
  • Raw coconut oil with an acid value of 12 had the following content of low-boiling impurities: Impurity Content [ppm] C 7 Ketone 29 C 9 Ketone 71 C 11 Ketone 581 C 13 Ketone 19 Phenol 214
  • the oil was pre-heated to 260 °C via a pre-heater and pumped at a flow rate of 200 kg/hr to the top of a column with an internal diameter of 130 mm packed with 4.6 m of a structured packing with a specific surface of 350 m 2 /m 3 .
  • the column was run at a top pressure of 10 mbar. Stripping steam was introduced into the bottom of the column at a flow rate of 2.0 kg/h.
  • the condenser of the column was adjusted to 80 °C, a second condenser to 40 °C.
  • the de-acidified oil had an acid value of 0.14, ketone and phenol contents were reduced to below detection limit.
  • a fatty acid stream of 10.6 kg/h was condensed having an acid value of 182.4 and a glyceride content of 16 %.
  • Contents of low-boiling impurities were: Impurity Content [ppm] C 7 Ketone 17 C 9 Ketone 70 C 11 Ketone 1,971 C 13 Ketone 343 Phenol 240
  • In the second condenser 0.6 kg/hr were condensed, having an acid value of 284 and a glyceride content of 0.5 %.
  • Contents of low boiling impurities were: Impurity Content [ppm] C 7 Ketone 0 C 9 Ketone 310 C 11 Ketone 30,423 C 13 Ketone 351 Phenol 10,478
  • the resulting ketone and phenol contents of a mixture of the de-acidified oil and the recovered fatty acids prior to a transesterification according to the current invention would be: Impurity Content [ppm] C 7 Ketone 0.9 C 9 Ketone 3.7 C 11 Ketone 104.8 C 13 Ketone 18.2 Phenol 12.8 Compared to the feed material an overall reduction of total ketones by 82 % and of phenol by 94 % was achieved.
  • Raw coconut oil with an acid value of 9.5 had the following content of low-boiling impurities: Impurity Content [ppm] C 7 Ketone 33 C 9 Ketone 73 C 11 Ketone 570 C 13 Ketone 14 Phenol 237
  • the oil was pre-heated to 245 °C via a pre-heater and feeded at a flow rate of 200 kg/h to the third packing of a column as shown in Figure 2 with an internal diameter of 130 mm equipped with three sections of a structured packing with a specific surface of 500 m 2 /m 3 , each of the packages having a height of 1.25 m.
  • the column was run at a top pressure of 10 mbar. Stripping steam was introduced into the bottom of the column at a flow rate of 2.0 kg/h.
  • the condenser of the column was adjusted to 40 °C.
  • the condensed second quality fatty acid was split into 0.2 kg, which were taken as top-cut and 14.7 kg reflux, which were fed back to the column top.
  • the second fatty acid quality had an acid value of 288 and a glyceride content of 0.1 %.
  • Contents of low-boiling impurities were: Impurity Content [ppm] C 7 Ketone 35.5 C 9 Ketone 498 C 11 Ketone 33,270 C 13 Ketone 3,330 Phenol 893
EP11165985.0A 2011-05-13 2011-05-13 Procédé pour l'obtention de produits oléochimiques ayant un contenu réduit en sous-produits Active EP2522711B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11165985.0A EP2522711B1 (fr) 2011-05-13 2011-05-13 Procédé pour l'obtention de produits oléochimiques ayant un contenu réduit en sous-produits

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP11165985.0A EP2522711B1 (fr) 2011-05-13 2011-05-13 Procédé pour l'obtention de produits oléochimiques ayant un contenu réduit en sous-produits

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EP2522711A1 true EP2522711A1 (fr) 2012-11-14
EP2522711B1 EP2522711B1 (fr) 2018-12-05

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015164106A1 (fr) * 2014-04-24 2015-10-29 The Procter & Gamble Company Procédé de conversion de substance odorante contenant des acides gras en glycérides désodorisés

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0127104B1 (fr) 1983-05-30 1987-03-18 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'esters d'acides gras et d'alcools aliphatiques à courte chaîne à partir de graisses et/ou d'huiles contenant des acides gras libres
US4838997A (en) * 1983-05-25 1989-06-13 Atlas-Danmark A/S Deodorization process for triglyceride oil
EP0332971B1 (fr) 1988-03-14 1993-09-15 Henkel Kommanditgesellschaft auf Aktien Procédé de transestérification continue d'esters d'alkyle à courte chaîne et d'acides gras
DE4321837A1 (de) 1993-07-01 1995-01-12 Henkel Kgaa Herstellung von Fettalkoholen durch Hydrieren von Fettderivaten, insbesondere Fettsäuremethylester
US6187974B1 (en) * 1998-03-11 2001-02-13 Dhw Deutsche Hydrierwerke Gmbh Rodleben Process for producing unsaturated fatty alcohols from lauric oils
EP1092703B1 (fr) 1999-10-14 2004-01-07 Cognis Deutschland GmbH & Co. KG Procédé de préparation d'esters méthyliques d'acides gras
US20050085653A1 (en) * 2001-11-01 2005-04-21 Garro Juan M. Method for fractionating grease trap waste and uses of fractions therefrom
EP1894913A1 (fr) * 2006-08-21 2008-03-05 Desmet Ballestra Oleo s.p.a. Production d'esters d'acides gras et d'alcools inférieurs
US20100022664A1 (en) * 2006-10-11 2010-01-28 Cognis Ip Management Gmbh Process for the partial hydrogenation of fatty acid esters

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4838997A (en) * 1983-05-25 1989-06-13 Atlas-Danmark A/S Deodorization process for triglyceride oil
EP0127104B1 (fr) 1983-05-30 1987-03-18 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'esters d'acides gras et d'alcools aliphatiques à courte chaîne à partir de graisses et/ou d'huiles contenant des acides gras libres
EP0332971B1 (fr) 1988-03-14 1993-09-15 Henkel Kommanditgesellschaft auf Aktien Procédé de transestérification continue d'esters d'alkyle à courte chaîne et d'acides gras
DE4321837A1 (de) 1993-07-01 1995-01-12 Henkel Kgaa Herstellung von Fettalkoholen durch Hydrieren von Fettderivaten, insbesondere Fettsäuremethylester
US6187974B1 (en) * 1998-03-11 2001-02-13 Dhw Deutsche Hydrierwerke Gmbh Rodleben Process for producing unsaturated fatty alcohols from lauric oils
EP1092703B1 (fr) 1999-10-14 2004-01-07 Cognis Deutschland GmbH & Co. KG Procédé de préparation d'esters méthyliques d'acides gras
US20050085653A1 (en) * 2001-11-01 2005-04-21 Garro Juan M. Method for fractionating grease trap waste and uses of fractions therefrom
EP1894913A1 (fr) * 2006-08-21 2008-03-05 Desmet Ballestra Oleo s.p.a. Production d'esters d'acides gras et d'alcools inférieurs
US20100022664A1 (en) * 2006-10-11 2010-01-28 Cognis Ip Management Gmbh Process for the partial hydrogenation of fatty acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015164106A1 (fr) * 2014-04-24 2015-10-29 The Procter & Gamble Company Procédé de conversion de substance odorante contenant des acides gras en glycérides désodorisés

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