WO2002102947A1 - Procede de traitement de matieres lipidiques - Google Patents

Procede de traitement de matieres lipidiques Download PDF

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Publication number
WO2002102947A1
WO2002102947A1 PCT/NL2002/000404 NL0200404W WO02102947A1 WO 2002102947 A1 WO2002102947 A1 WO 2002102947A1 NL 0200404 W NL0200404 W NL 0200404W WO 02102947 A1 WO02102947 A1 WO 02102947A1
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WO
WIPO (PCT)
Prior art keywords
lipid material
granulate
gas
lipid
reactive
Prior art date
Application number
PCT/NL2002/000404
Other languages
English (en)
Inventor
Geert Feye Woerlee
Hubert Clemens Pellikaan
Antonius Wilhelmus Petrus Gerardus Peters Rit
Original Assignee
Feyecon Development & Implementation B.V.
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 Feyecon Development & Implementation B.V. filed Critical Feyecon Development & Implementation B.V.
Publication of WO2002102947A1 publication Critical patent/WO2002102947A1/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
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • C11C1/06—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using solid catalysts
    • 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
    • C11B3/10—Refining fats or fatty oils by adsorption
    • 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
    • C11C1/08—Refining
    • C11C1/10—Refining by distillation
    • C11C1/103—Refining by distillation after or with the addition of chemicals
    • C11C1/106—Refining by distillation after or with the addition of chemicals inert gases or vapors
    • 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
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • C11C3/123—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on nickel or derivates

Definitions

  • the present invention is concerned with a new method of processing lipid materials, such as triglycerides and waxes, which process involves contacting such lipid materials with a reactive granulate in the presence of a gas in near supercritical state.
  • the reactive granulate employed in the present process may suitably be a catalyst, such as bleaching earth or hydrogenation catalyst, or an adsorbent, such as active carbon.
  • gases that can advantageously be used in the present method include carbon dioxide, ethane, propane and nitrous oxide.
  • the present invention specifically relates to methods of processing in which the composition of the lipid material is altered as a result of the interaction between the lipid material and the reactive granulate. This interaction may incite certain chemical reactions to occur in the lipid material and/or it may lead to selective adsorption of lipid material components onto the granulate.
  • the present invention is not concerned with an extraction or fractionation processes wherein a lipid material is separated into 2 or more lipid material fractions by means of extraction with a supercritical solvent.
  • Lipid materials such as triglycerides, waxes and fosfolipids all have in common that they are obtained from natural sources in a crude quality which is often unsuitable for human consumption or other commercial uses. Hence such crude lipid raw materials are usually subjected to a sequence of refining and other processing steps to upgrade the quality and/or applicability thereof. Processes commonly applied in the upgrading of crude lipid materials include bleaching, deodorisation, fractionation, hydrogenation, interesterification, hydrolysis etc.
  • lipid materials are well known in the art and are normally conducted at elevated temperatures and in some cases also at elevated pressures. Some of these processes may apply processing aids such as organic solvents, adsorbents and catalysts. Examples of adsorbents commonly used in the processing of lipid materials are active carbon and silica. Catalysts widely employed in oil processing include bleaching earth, hydrogenation catalysts and interesterification catalysts. Both chemical and enzymatic catalysis are used in the field of oil processing. Enzymatic interesterification, for instance, is applied on an industrial scale.
  • the application of supercritical gases in the processing of lipid materials is known in the art.
  • the known areas of application are extraction of lipid materials from plant materials and isolation of lipid fractions through supercritical extraction. These techniques have in common that the supercritical gas is added to the lipid material in an excess amount so that it may function as an extraction solvent.
  • the supercritical gas containing dissolved components is separated from the bulk of the material after which the extract is recovered by reducing the pressure and allowing the gas to escape through evaporation. This cycle is normally repeated several times, often as part of a semi-continuous process.
  • the following 2 prior art documents describe the use of supercritical gases in the processing of lipid materials, wherein said supercritical gas acts as an extraction solvent.
  • DE-A 4 306 303 (Schulmeyer et al.) relates to a process for obtaining vegetable oils by extraction with liquid or supercritical carbon dioxide, wherein the solvent flows through the comminuted oil seed or a crude oil and is subsequently passed through a bed of bleaching agent.
  • US 4,548,755 (Stahl et al) concerns a process for the extractive production of waxes from fossil, vegetable or animal starting material, by extraction with a gas at supercritical pressure and temperature conditions wherein the separation of the extract-containing gas is achieved in a separator part by pressure reduction and/or temperature change.
  • the present invention relates to methods of processing lipid materials that are more efficient than the corresponding conventional methods.
  • the present method was developed starting from the insight that in many existing processing methods, particularly in those cases where a reactive granulate is employed, the rate limiting factor is the rate of diffusion of the reactants in the lipid material. Surprisingly it was found that the diffusion rates of these reactants could be increased significantly by dissolving into the lipid material a gas at near supercritical conditions. The inclusion of a near supercritical gas was found to be particularly advantageous in processing methods that employ a reactive granulate, such as a catalyst or an adsorbent.
  • one aspect of the invention is concerned with a method of processing lipid material comprising the steps of a) dissolving into the lipid material from 5-95 wt.% of a gas selected from the group consisting of carbon dioxide, ethane, propane, or nitrous oxide and mixtures thereof, at a temperature and a pressure at which the gasper se (i.e. without lipid material) would be near its supercritical state, b) contacting the lipid material containing the dissolved gas with a reactive granulate, c) separating the granulate from the lipid material and d) allowing the gas to evaporate from the lipid material by reducing the pressure.
  • a gas selected from the group consisting of carbon dioxide, ethane, propane, or nitrous oxide and mixtures thereof
  • the lipid material is liquid when it is contacted with the reactive granulate and also when it is separated therefrom. In order to ensure that the material is liquid it is advisable to operate the method at a temperature well above the melting point of said lipid material.
  • the gas is dissolved into the lipid material and not the reverse, i.e. when the lipid material is dissolved into the gas.
  • the lipid material contains 10-90 wt.%, more preferably if 30-70 wt.% of the dissolved gas.
  • the percentage of dissolved gas will simply be determined by the applied temperature and pressure.
  • it is crucial that the streams are mixed in such a ratio that the amount of dissolved gas is maintained within the range needed to obtain the benefits of the present invention.
  • step b) is carried out at a temperature and pressure at which the gasper se would be near its supercritical state.
  • the temperature of the gas is at least T c - 60 °C and the pressure is at least 0.5xP c (i.e. P c /2), wherein T c and P c represent the critical temperature and critical pressure of the gas. More preferably the temperature of the gas is between T c -60 °C and T c +150 °C and the pressure is between 0.8xP c and 12xP c .
  • the critical temperatures and pressures for the (pure) gases that are preferentially used in the present method are listed in the table below.
  • the reactive granulate used in the present method is preferably selected from the group consisting of catalysts, adsorbents and mixtures thereof.
  • catalysts the present method offers the advantage that, due to the increased diffusion rates, at the catalyst surface reactants be replenished more quickly and, in addition, reaction products will disappear more quickly. Both these effects will increase catalytic effectiveness.
  • adsorbents the present method offers the advantage that components dissolved in the lipid material will be captured more quickly by the absorbent than is the case for conventional methods employing the same adsorbent.
  • Reactive granulates which can be used in accordance with the present invention are preferably selected from the group consisting of bleaching earth, active carbon, hydrogenation catalyst and mixtures thereof.
  • the colour of refined yellow sunflower oil at room temperature was determined with a spectrophotometer. Expressed in Lab values the colour was (77.9, 0.55, and 7.39). 100 gram of sunflower oil was put in an autoclave of 323 ml.
  • the colour of yellow beeswax was determined with a spectrophotometer. Expressed in Lab values the colour was (30.9, 4.71, and 21.9).
  • Example 3 was repeated except that the process was ca ⁇ ied out at ambient pressure, the temperature applied was 80 °C and contact time was increased to 20 minutes. Despite the fact that a longer contact time and higher temperature were applied, the yellow colour of the processes was not removed as effectively as in experiment 3. This observation was confirmed by the Lab values of the treated beeswax which were determined as (36.4, -0.54, 8.34).

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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)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un nouveau procédé de traitement de matières lipidiques, telles que les triglycérides et les cires, qui consiste à mettre lesdites matières lipidiques en contact avec un granulat réactif en présence d'un gaz proche de l'état supercritique. L'invention se rapporte en particulier à un procédé de traitement d'une matière lipidique qui consiste : a) à dissoudre dans la matière lipidique entre 5 et 95 % en poids d'un gaz choisi dans le groupe composé du dioxyde de carbone, de l'éthane, du propane, ou de l'oxyde nitreux et des mélanges des ces derniers, à une température et une pression auxquelles le gaz per se serait proche de son état supercritique ; b) à mettre en contact la matière lipidique contenant le gaz dissous avec un granulat réactif ; c) à séparer le granulat de la matière lipidique ; et d) à permettre au gaz de s'évaporer de la matière lipidique en réduisant la pression. Le granulat réactif utilisé dans le traitement de l'invention peut être de préférence un catalyseur, tel qu'une terre décolorante ou un catalyseur d'hydrogénation, ou un adsorbant tel que du charbon actif.
PCT/NL2002/000404 2001-06-19 2002-06-19 Procede de traitement de matieres lipidiques WO2002102947A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01202375A EP1270710A1 (fr) 2001-06-19 2001-06-19 Procédé pour le traitement de matières grasses
EP01202375.0 2001-06-19

Publications (1)

Publication Number Publication Date
WO2002102947A1 true WO2002102947A1 (fr) 2002-12-27

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Application Number Title Priority Date Filing Date
PCT/NL2002/000404 WO2002102947A1 (fr) 2001-06-19 2002-06-19 Procede de traitement de matieres lipidiques

Country Status (2)

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EP (1) EP1270710A1 (fr)
WO (1) WO2002102947A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2245901A1 (es) * 2004-07-15 2006-01-16 Universitat Politecnica De Catalunya Proceso de hidrogenacion parcial de trigliceridos insaturados en fase vapor a alta presion y reactor para la realizacion de dicho proceso.
WO2014083124A1 (fr) 2012-11-28 2014-06-05 Dsm Ip Assets B. V. Formulation pulvérulente
EP3766557A1 (fr) 2019-07-19 2021-01-20 Folium Biosciences Europe B.V. Procédé d'extraction
EP3766558A1 (fr) 2019-07-19 2021-01-20 Folium Biosciences Europe B.V. Procédé d'extraction
EP3766556A1 (fr) 2019-07-19 2021-01-20 Folium Biosciences Europe B.V. Procédé d'extraction
WO2021013697A1 (fr) 2019-07-19 2021-01-28 Folium Biosciences Europe B.V. Procédé d'extraction

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0800875D0 (en) * 2008-01-17 2008-02-27 Pharma Marine As Process
ES2350669B1 (es) * 2009-06-03 2011-11-15 Universitat Politècnica De Catalunya Proceso continuo de hidrogeneracion de aceites vegetales en fase liquida a presion y a temperatura con obtencion de una grasa con bajo contenido en isomero trans
CN101942359A (zh) * 2010-09-27 2011-01-12 东北农业大学 一种co2超临界状态下生产低反式脂肪酸含量食用植物油脂的脱色方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2420761A (en) * 1942-10-23 1947-05-20 Universal Oil Prod Co Process for treating a liquid with a suspension of solids by passage thereof througha separator, regenerating the separated solids for re-use with untreated liquid
WO1996001304A1 (fr) * 1994-07-01 1996-01-18 Poul Möller Ledelses- Og Ingeniörrrådgivning Aps Procede d'hydrogenation d'un substrat et produits fabriques selon ce procede
WO2000005327A1 (fr) * 1998-07-24 2000-02-03 Lockheed Martin Idaho Technologies Company Procede de production de biodiesel, de lubrifiants, et d'additifs pour carburants et lubrifiants dans un milieu de liquide critique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2420761A (en) * 1942-10-23 1947-05-20 Universal Oil Prod Co Process for treating a liquid with a suspension of solids by passage thereof througha separator, regenerating the separated solids for re-use with untreated liquid
WO1996001304A1 (fr) * 1994-07-01 1996-01-18 Poul Möller Ledelses- Og Ingeniörrrådgivning Aps Procede d'hydrogenation d'un substrat et produits fabriques selon ce procede
WO2000005327A1 (fr) * 1998-07-24 2000-02-03 Lockheed Martin Idaho Technologies Company Procede de production de biodiesel, de lubrifiants, et d'additifs pour carburants et lubrifiants dans un milieu de liquide critique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MACHER M-B ET AL: "PARTIAL HYDROGENATION OF FATTY ACID METHYL ESTERS AT SUPERCRITICAL CONDITIONS", FETT - LIPID, WILEY-VCH VERLAG,WEINHEIM, DE, vol. 101, no. 8, August 1999 (1999-08-01), pages 301 - 305, XP000848744, ISSN: 0931-5985 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2245901A1 (es) * 2004-07-15 2006-01-16 Universitat Politecnica De Catalunya Proceso de hidrogenacion parcial de trigliceridos insaturados en fase vapor a alta presion y reactor para la realizacion de dicho proceso.
WO2014083124A1 (fr) 2012-11-28 2014-06-05 Dsm Ip Assets B. V. Formulation pulvérulente
EP3766557A1 (fr) 2019-07-19 2021-01-20 Folium Biosciences Europe B.V. Procédé d'extraction
EP3766558A1 (fr) 2019-07-19 2021-01-20 Folium Biosciences Europe B.V. Procédé d'extraction
EP3766556A1 (fr) 2019-07-19 2021-01-20 Folium Biosciences Europe B.V. Procédé d'extraction
WO2021013697A1 (fr) 2019-07-19 2021-01-28 Folium Biosciences Europe B.V. Procédé d'extraction

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Publication number Publication date
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