EP1752522A1 - Procédé de traitement de graisses - Google Patents

Procédé de traitement de graisses Download PDF

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Publication number
EP1752522A1
EP1752522A1 EP06015943A EP06015943A EP1752522A1 EP 1752522 A1 EP1752522 A1 EP 1752522A1 EP 06015943 A EP06015943 A EP 06015943A EP 06015943 A EP06015943 A EP 06015943A EP 1752522 A1 EP1752522 A1 EP 1752522A1
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EP
European Patent Office
Prior art keywords
process according
carbon atoms
mono
saturated
fatty substances
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Withdrawn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
EP06015943A
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German (de)
English (en)
Inventor
Stefan Franzen
Thomas Kapala
Eike Ulf Mahnke
Yiwen Dong
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
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
Publication of EP1752522A1 publication Critical patent/EP1752522A1/fr
Withdrawn legal-status Critical Current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
    • 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
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases
    • 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

Definitions

  • the invention is in the field of oleochemistry and relates to a novel process for working up fatty substances from esterification and transesterification reactions, especially for refining and deacidification.
  • Dry refining uses solid or bound sodium hydroxide. If necessary, soaps are produced as neutralization products in these processes. In contrast, in the wet refining, aqueous caustic soda solution or crystal soda solution and a large amount of water are added, so that subsequent separation of the water is required. In addition, formed soap must be separated by washing several times from the reaction mixture. Subsequently, the reaction product optionally undergoes deodorization, drying and filtration steps.
  • the complex object of the present invention was therefore to develop an improved process for the workup of products from esterification and transesterification reactions for refining and deacidification, which is characterized in comparison to the prior art in that the number of purification steps and the amount of Wastewater is significantly reduced. At the same time, the loss due to product saponification should also be reduced. Finally, the process should be designed so that catalyst contaminants, e.g. Sulfate anions and mono- or polyvalent metal cations can be removed.
  • catalyst contaminants e.g. Sulfate anions and mono- or polyvalent metal cations
  • the invention relates to a process for working up fatty substances from esterification and transesterification reactions, which is characterized in that they are treated with ion exchangers.
  • the advantage of the method according to the invention is in particular that the free acid is bound directly to the ion exchanger by the use of anion exchangers.
  • water is formed only in stoichiometric amounts, which is then removed in the drying process.
  • the complex washing out of the soap and the filtration omitted at the same time the amount of wastewater is significantly reduced. Due to the lower basicity of the anion exchangers and the milder reaction temperatures, there is less loss due to product saponification in comparison to conventional wet refining. At the same time, other interfering anions, especially the undesirable sulfates, are removed.
  • monovalent or polyvalent metal cations can be separated by series connection of cation and anion exchange steps. The regeneration of the ion exchanger is possible as in aqueous ion exchanger systems with dilute aqueous sodium or potassium hydroxide solution and dilute hydrochloric or sulfuric acid.
  • esterification or transesterification products is not very critical to the process according to the invention.
  • glycerides of the formula (I) can be worked up as fatty substances, in the R 1 CO for a saturated and mono- or polyunsaturated acyl radical having 2 to 22 carbon atoms, and R 2 and R 3 are independently hydrogen or saturated and mono- or polyunsaturated acyl radicals having 2 to 22, preferably 6 to 18 carbon atoms stand.
  • Typical examples are vegetable oils such as coconut oil, palm oil, palm kernel oil, olive oil, sunflower oil, thistle oil, rapeseed oil, almond oil and the like.
  • esters of monocarboxylic acids of the formula (II) can also be used as fatty substances, R 4 COO-R 5 (II) wherein R 4 CO is a saturated and mono- or polyunsaturated acyl radical having 2 to 22, preferably 6 to 18 and in particular 12 to 14 carbon atoms and R 5 is a saturated or mono- or polyunsaturated, optionally substituted alk (en) ylrest with 2 to 22, preferably 6 to 18 and especially 12 to 14 carbon atoms or the rest of a (poly) alkylene glycol, especially of ethylene glycol, diethylene glycol, propylene glycol or dipropylene glycol.
  • Typical examples are wax esters based on fatty acids having 6 to 22 and preferably 12 to 18 carbon atoms and corresponding fatty alcohols also having 6 to 22 and preferably 12 to 18 carbon atoms, such as myristyl myristate, myristyl palmitate, stearyl palmitate, stearyl stearate, cetearyl stearate, oleyl oleate and the like.
  • suitable starting materials are esters of dicarboxylic acids of the formula (III) , R 6 OOC- (A) n -COOR 7 (III) in the A for a linear or branched alkylene or alkenylene group having 1 to 10 carbon atoms or a phenyl radical, n is 0 or 1, R 6 and R 7 are independently saturated or mono- or polyunsaturated, optionally substituted alk (en) yl radicals with 2 to 22, preferably 6 to 22 and especially 12 to 18 carbon atoms or the radicals of a (poly) alkylene glycol, especially of ethylene glycol, diethylene glycol, propylene glycol or dipropylene glycol. Typical examples are the stearyl, palmityl or oleyl esters of malonic acid or adipic acid.
  • the starting materials may preferably have acid numbers in the range of 0.5 to 10.
  • ion exchangers for workup and catalysis in aqueous systems are well known in the art, e.g. Softening or desalination of water, recovery of metal. Otherwise, ion exchangers are used in chromatography. In oleochemistry, ion exchangers are used to purify glycerin (desalting). Another application is the use of cation exchangers for acid catalysis in esterification reactions (eg in the preparation of isopropyl myristate / palmitate). However, they have not yet been considered for the deacidification of esterification and transesterification products.
  • anion exchangers or combinations of series-connected anion and cation exchangers, depending on whether only free fatty acids and optionally further interfering anions or, in addition, metal cations are to be separated off.
  • ion exchangers based on polymeric resins and other solid matrices having functional groups are suitable (for example zeolites or oxidic ion exchangers).
  • anion exchangers are polymeric matrices based on polystyrene-divinylbenzene-dimethylamine, polystyrene-divinylbenzene-trimethylammonium chloride or polyacrylodimethylamine, as are commercially available, for example, from Purolite.
  • Typical examples of cation exchangers are polystyrene-divinylbenzene resins having sulfonic acid or carboxyl groups.
  • both weakly basic and strongly basic anion exchangers or strongly acidic or weakly acidic cation exchangers are suitable, with particle sizes in the range from 50 to 1000 .mu.m, preferably between 300 and 800 .mu.m, having proved to be particularly advantageous.
  • the ion exchangers have a range of application between 0 and 200 ° C, depending on the type; Synthetic resin-based cation exchangers can usually be used up to a maximum of 150 ° C. Synthetic resin based anion exchangers are common can be used up to a maximum of 70 ° C.
  • the workup is therefore carried out at temperatures in the range of 0 to 150 ° C, more preferably in the range of 25 to 95 ° C.
  • the anion exchangers can be used directly after conditioning. A drying of the anion exchanger and a pretreatment with organic substances are not necessary for use.
  • the loading capacity of the anion exchangers in the organic system differs only slightly from that in the aqueous system. The regeneration with dilute sodium hydroxide solution can be repeated several times.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP06015943A 2005-08-10 2006-08-01 Procédé de traitement de graisses Withdrawn EP1752522A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005037707A DE102005037707A1 (de) 2005-08-10 2005-08-10 Verfahren zur Aufarbeitung von Fettstoffen

Publications (1)

Publication Number Publication Date
EP1752522A1 true EP1752522A1 (fr) 2007-02-14

Family

ID=37430106

Family Applications (1)

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EP06015943A Withdrawn EP1752522A1 (fr) 2005-08-10 2006-08-01 Procédé de traitement de graisses

Country Status (3)

Country Link
US (1) US20070060763A1 (fr)
EP (1) EP1752522A1 (fr)
DE (1) DE102005037707A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB762362A (en) * 1953-06-10 1956-11-28 Unilever Ltd Improvements in the treatment of solutions containing carboxylic acids and derivatives thereof
GB934681A (en) * 1960-10-27 1963-08-21 Armour & Co Improvements in or relating to the preparation of mixed glycerol esters of fatty and lactic acids
DE2743443A1 (de) * 1976-09-30 1978-04-06 Rohm & Haas Verfahren zur entfernung von organischen lewis-saeuren aus einem mit wasser nicht mischbaren fluid
JPS54152672A (en) * 1978-05-24 1979-12-01 Asahi Chem Ind Co Ltd Preparation of sebacic acid
EP0333472A2 (fr) * 1988-03-16 1989-09-20 PALM OIL RESEARCH & DEVELOPMENT BOARD Production de tocophénols et de tocotriénols de haute concentration à partir de produits secondaires de l'huile de palme
DE19739203A1 (de) * 1997-09-08 1999-03-11 Bayer Ag Verfahren zur Reinigung von Esterölen
DE20202083U1 (de) * 2002-02-12 2002-07-18 Kuntschar & Schlueter Gmbh Ene Anlage zur Veresterung von glyzerinhaltigen Pflanzenfetten, insbesondere fetten Ölen und hier insbesondere von gebrauchten Frittierfetten mit mehreren Anlagenkomponenten
WO2003040081A1 (fr) * 2001-11-08 2003-05-15 Kovacs Andras Ameliorations apportees ou associees a un procede de transesterification d'huiles vegetales
WO2004065532A1 (fr) * 2003-01-22 2004-08-05 Cognis Ip Management Gmbh Attenuation de l'odeur de composants huileux par adsorption avec des adsorbants polymeres

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4382124B1 (en) * 1958-07-18 1994-10-04 Rohm & Haas Process for preparing macroreticular resins, copolymers and products of said process
US6316647B1 (en) * 1993-02-26 2001-11-13 Shiseido Company, Ltd. Cation-exchanged clay mineral, packing material for chromatography using the same and method of producing the same
JP4278910B2 (ja) * 2002-03-13 2009-06-17 花王株式会社 エステルの製造法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB762362A (en) * 1953-06-10 1956-11-28 Unilever Ltd Improvements in the treatment of solutions containing carboxylic acids and derivatives thereof
GB934681A (en) * 1960-10-27 1963-08-21 Armour & Co Improvements in or relating to the preparation of mixed glycerol esters of fatty and lactic acids
DE2743443A1 (de) * 1976-09-30 1978-04-06 Rohm & Haas Verfahren zur entfernung von organischen lewis-saeuren aus einem mit wasser nicht mischbaren fluid
JPS54152672A (en) * 1978-05-24 1979-12-01 Asahi Chem Ind Co Ltd Preparation of sebacic acid
EP0333472A2 (fr) * 1988-03-16 1989-09-20 PALM OIL RESEARCH & DEVELOPMENT BOARD Production de tocophénols et de tocotriénols de haute concentration à partir de produits secondaires de l'huile de palme
DE19739203A1 (de) * 1997-09-08 1999-03-11 Bayer Ag Verfahren zur Reinigung von Esterölen
WO2003040081A1 (fr) * 2001-11-08 2003-05-15 Kovacs Andras Ameliorations apportees ou associees a un procede de transesterification d'huiles vegetales
DE20202083U1 (de) * 2002-02-12 2002-07-18 Kuntschar & Schlueter Gmbh Ene Anlage zur Veresterung von glyzerinhaltigen Pflanzenfetten, insbesondere fetten Ölen und hier insbesondere von gebrauchten Frittierfetten mit mehreren Anlagenkomponenten
WO2004065532A1 (fr) * 2003-01-22 2004-08-05 Cognis Ip Management Gmbh Attenuation de l'odeur de composants huileux par adsorption avec des adsorbants polymeres

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE FSTA [online] INTERNATIONAL FOOD INFORMATION SERVICE (IFIS), FRANkFURT-MAIN, DE; 1993, DEWETTINCK K ET AL: "Lipase-catalysed interesterification of milkfat: influence on the free fatty acid profile.", XP002409057, Database accession no. 93-1-09-p0001 *
MEDEDELINGEN VAN DE FACULTEIT LANDBOUWWETENSCHAPPEN RIJKSUNIVERSITEIT GENT, vol. 57, no. 4B, 1992, LAB. OF FOOD TECH., CHEM. & MICROBIOL., FAC. OF AGRIC. SCI., UNIV. OF GHENT, B-9000 GHENT, BELGIUM, pages 1905 *

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DE102005037707A1 (de) 2007-02-15
US20070060763A1 (en) 2007-03-15

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