WO2012113495A1 - Procédé pour l'obtention d'alcools gras a partir de déchets de graisses ou d'huiles - Google Patents

Procédé pour l'obtention d'alcools gras a partir de déchets de graisses ou d'huiles Download PDF

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Publication number
WO2012113495A1
WO2012113495A1 PCT/EP2012/000269 EP2012000269W WO2012113495A1 WO 2012113495 A1 WO2012113495 A1 WO 2012113495A1 EP 2012000269 W EP2012000269 W EP 2012000269W WO 2012113495 A1 WO2012113495 A1 WO 2012113495A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
fatty
acid alkyl
alkyl ester
stream
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.)
Ceased
Application number
PCT/EP2012/000269
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German (de)
English (en)
Inventor
Rudolf BÖNSCH
Eckhard Seidel
Martin Rothaemel
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Air Liquide Global E&C Solutions Germany GmbH
Original Assignee
Lurgi GmbH
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Filing date
Publication date
Application filed by Lurgi GmbH filed Critical Lurgi GmbH
Publication of WO2012113495A1 publication Critical patent/WO2012113495A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • 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
    • C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
    • 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
    • C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency
    • Y02P20/129—Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines
    • 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
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Definitions

  • the invention relates to a process for obtaining fatty alcohols from animal fats and / or vegetable oils.
  • the invention relates to the recovery of high-quality, biodegradable fatty alcohols from low-grade waste fats and waste oils.
  • biodegradable fatty alcohols as a raw material for example for the detergent industry is carried out according to the prior art either by catalytic hydrogenation of canned fatty acids in a batch reactor operated with catalyst slurry or continuously in a trickle bed reactor with solid catalyst bed based on methyl esters or Wax esters of the corresponding fatty acids.
  • Both fatty acid fractions are the intensively mixed in a stirred reactor with the addition of fatty alcohol at a temperature of about 250 ° C and at atmospheric pressure for an average of 12 hours, the reaction water is continuously removed.
  • the obtained during hydrogenation reaction product is cooled and thereby separated into hydrogen and crude fatty alcohol.
  • the hydrogen is reused to hydrogenate the wax ester on a fixed bed catalyst of copper-chromium oxide catalyst particles.
  • a portion of the crude fatty alcohol is recycled to the stirred reactor for the esterification of the fatty acids and the other part is either rehydrated once in the stirred reactor or used directly as a raw material.
  • a liquid intermediate product comprising at least 50% by weight of wax ester is produced from a liquid starting mixture containing fatty acids at temperatures of 120 to 320 ° C. and pressures of 20 to 400 bara , which is hydrogenated by the addition of hydrogen and with admixing of fine-grained catalyst and an at least 75 wt .-% of fatty alcohol existing crude product is formed. From the crude product, a partial flow containing fatty alcohol is separated and added to the liquid starting mixture. The hydrogenation of fatty acid methyl ester in the gas phase requires a separate cycle.
  • the subject of patent specification DE 3425758 C is a process for the preparation of alcohols by hydrogenating compounds having the corresponding number of carbon atoms with an acid, ester or aldehyde function, by the hydrogenation at a hydrogen pressure in the range of 20 to 100 bar and at a temperature in the range of 150 to 300 ° C in the presence of a catalyst consisting of a mixture of copper and chromium with about 20 to about 40 wt .-% copper (calculated as oxide) and a supported copper component with about 5 to about 45% by weight of copper.
  • the patent EP 0454704 B describes a process for the preparation of fatty alcohols from fatty acid with a lower alkanol to form the corresponding lower ester, in which the ester in the presence of a catalyst at a temperature in the range of 80 to 140 ° C and a pressure in Hydrogenated range of 0.1 to 25 bar to fatty alcohol and the hydrogenation product using an acidic ion exchange catalyst of a transesterification to react the unreacted ester of the hydrogenation product by reaction with the fatty alcohol to wax ester. Unreacted alkanol is evaporated from the mixture and the remaining mixture is distilled so that an ester-free fatty alcohol is produced as the top product and a distillation residue containing fatty alcohol and wax ester is formed.
  • the subject matter of the invention taught in DE-Offenlegungsschrift DE 4335781 A1 is a process for the preparation of vegetable-based fatty alcohols containing substantially unsaturated fatty alcohols and mixtures of saturated and unsaturated fatty alcohols having the general formula P »iOH, where PM is a saturated or unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms, containing the triglycerides contained in the vegetable fats raw materials either by pressure splitting into the fatty acids and then optionally esterified with methanol in the fatty acid methyl esters and finally the fatty acid or the Fatty acid methyl ester hydrogenated to fatty alcohol.
  • PM is a saturated or unsaturated, linear or branched alkyl radical having 8 to 22 carbon atoms
  • Waste fats and waste oils are first hydrolyzed with high pressure steam, for example in a splitting tower, thermally into fatty acids and glycerine water.
  • the separated glycerol water phase is purified according to methods known per se, for example by using membrane technology, if appropriate in combination with ion exchangers, to the extent that a salable glycerol with a pharmaceutical unit can be obtained as by-product in a final distillation.
  • the fatty acid fraction obtained by steam cracking is then subjected to purification by a thermal separation process; This can be done using a fractional distillation, a simple, single-stage distillation or even a demineralization by means of ion exchangers.
  • the thus freed of foreign substances fatty acid is then reacted in the ester synthesis step with short-chain alkenes in the presence of an acidic catalyst to a fatty acid alkyl ester.
  • the excess alkene can be recycled to the reaction.
  • alkenes which are gaseous at ambient conditions are to be understood; these are ethylene, propylene, 1-butene, cis-2-butene, trans-2-butene and isobutene.
  • ethylene propylene
  • 1-butene 1-butene
  • cis-2-butene cis-2-butene
  • trans-2-butene trans-2-butene
  • isobutene the simple and without equilibrium limitations, known per se known addition of short-chain alkenes to fatty acids to form the fatty acid to gozuver,den fatty acid alkyl ester in the art was not considered.
  • One reason for this could be the previous high price of the required alkenes.
  • typical petrochemical products they tend to be foreign to the technology field of fat and oil processing.
  • the fatty acid alkyl ester thus obtained is cleaved in a subsequent hydrogenation at 100 to 300 ° C, preferably from 180 to 250 ° C, and a plant pressure of 1 to 250 bara to the fatty alcohol product and an alkanol obtained as a coproduct.
  • a simple thermal separation process for example a single-stage evaporation separation, the two end products are easily and safely separated from each other due to the differences in boiling point. It is advantageous that in addition to the target product fatty alcohol and another alcohol is obtained as a much sought after commercial product.
  • the fatty acid alkyl ester which is unreacted in the hydrogenation can likewise be separated off by means of thermal separation processes in a manner known to the person skilled in the art and can preferably be recycled to the hydrogenation.
  • a preferred embodiment of the invention provides that the purification of second stream containing free fatty acids in process step 1 (b) takes place by distillation.
  • Suitable catalysts are both brönstedt and lewisacide compounds.
  • the acid catalysts used can be both liquid and solid.
  • mineral acids such as sulfuric acid or hydrochloric acid can be used as liquid catalysts.
  • Liquid acids have the advantage of being easily and homogeneously distributed in the reaction mixture.
  • Particularly suitable solid catalysts are acidic clays, zeolites or ion exchangers, for example sulphonic acid bases. In addition to their high catalytic activity they have the advantage of being easily separated from the reaction mixture.
  • a further embodiment of the inventive method provides that the order of the third reduction ⁇ purified fatty acids containing stream in step 1 (c) with ethylene, propylene, 1-butene, cis-2-butene, trans-2-butene, iso- Butene or mixtures of these alkenes, wherein the reaction with propylene is preferred.
  • various alcohols can be obtained as by-products of the fatty alcohol.
  • propylene is used, the by-product obtained in the hydrogenation of the fatty acid propyl ester is the alcohol isopropanol, which is a wished sales product.
  • a further modification of the process envisages reacting mixtures of short-chain alkenes which are gaseous under ambient conditions with the fatty acid obtained in process step 1 (b), not pure alkenes.
  • Such alkene mixtures are obtained, for example, as the primary product of the MTP® process.
  • the subsequent hydrogenation then falls to an alcohol mixture of ethanol, propanols and butanols, which is still easily due to their difference in boiling point to the fatty alcohol, for example, by simple distillation, separated from this and also represents a sought after commercial product.
  • the reaction of the third, purified fatty acid-containing stream in process step 1 (c) with the alkene is carried out at pressures of 1 to 50 bara, preferably 1 to 10 bara, most preferably 1 to 5 bara.
  • the reaction temperature is typically 100 to 300 ° C bara, preferably 150 to 250 ° C.
  • the short-chain alkene is preferably metered into the slurry in gaseous form; this can be done via gas distribution trays or gassing stirrers.
  • the purification of the fourth, fatty acid and fatty acid alkyl ester-containing stream in process step 1 (d) takes place according to a preferred embodiment of the process by distillation or rectification.
  • the corresponding fatty acid isopropyl ester is recovered, which is recovered in a subsequent distillation as a top product.
  • this distillation - as well as in the process steps 1 (b) and 1 (f) optionally distillations used - under partial vacuum, preferably at pressures below 10 mbara, carried out to ensure gentler distillation conditions and to prevent excessive thermal stress on the distillation feed.
  • a further embodiment of the invention provides that the hydrogenating cleavage of the fifth, fatty acid alkyl ester-containing stream in process step 1 (e) in a slurry of a solid, fine copper or nickel-based hydrogenation catalyst in the fatty acid alkyl ester at temperatures of 100 to 300 ° C. , preferably from 180 to 250 ° C and pressures of 1 bara to 250 bara.
  • the process can be designed so that the hydrogenating cleavage of the fifth, fatty acid alkyl ester-containing stream in process step 1 (e) in a trickle bed reactor at temperatures of 100 to 300 ° C, preferably from 180 to 250 ° C and pressures of 1 bara to 250 Bara is carried out, being applied to a bed of solid, granular hydrogenation catalyst based on copper or nickel, the fatty acid alkyl ester from above as a liquid phase and the required hydrogen is added in cocurrent or countercurrent to the liquid phase.
  • the direct current mode of operation is preferred because, under these conditions, partial mechanical flooding of the catalyst bed can not result in mechanically caused abrasion effects on the catalyst. In a countercurrent mode of operation there would be the risk of turbulence of the catalyst bed due to rising hydrogen.
  • the separation of the sixth stream comprising fatty alcohol, alkanol and unreacted fatty acid alkyl ester to obtain the fatty alcohol and the alkanol in process step 1 (e) takes place by distillation.
  • the fatty acid alkyl ester which is not reacted in the hydrogenation can likewise be separated off by means of thermal separation processes in a manner known to the person skilled in the art, and preferably recycled to the hydrogenation.
  • FIGURE shows a schematically illustrated basic flow diagram of an embodiment of the method according to the invention, which is explained in more detail below in connection with an exemplary embodiment.
  • the bottom product of the distillation column is withdrawn via line 1 1 and contains in addition to mono- and diglycerides still small amounts of unreacted fats or oils and the complete substance group of the sterol-containing compounds. In particular when vegetable oils are used, the tocopherols accumulate in the bottom product.
  • the stirred reactor (12) can be tempered via a heating / cooling jacket, as well as by optional, not shown, immersed in the reaction mixture heating / cooling elements. The reaction is carried out at pressures of 1 to 50 bara. The reaction temperature is around 200 ° C. Via line 14, the excess propylene is released discharged from the stirred reactor.
  • the top product of the distillation column (20) containing the fatty acid isopropyl ester is fed via line (22) at the top of the hydrogenation reactor (23), in which there is a fixed bed formed from catalyst moldings of the type E 860 (manufacturer: BASF AG, Ludwigshafen) , Hydrogen is recirculated via line (24) in an amount of 50 mol of hydrogen per mole of fatty acid alkyl ester.
  • Hydrogen is recirculated via line (24) in an amount of 50 mol of hydrogen per mole of fatty acid alkyl ester.
  • spent hydrogen is metered via line 28 by means of a compressor (31).
  • the fatty acid alkyl ester is converted to fatty alcohols and alkanols.
  • the mixture exiting the reaction vessel (23) via line (25) is separated in the cooler separator (26) into hydrogen and fatty alcohols and unreacted fatty acid alkyl ester.
  • the hydrogen is passed via line (27) in a compressor (29) and returned via line (24) in the reaction vessel (23), wherein spent hydrogen via line (28) is supplemented.
  • Via line (30) a product stream containing a maximum of about 620 kg / h of fatty alcohol and 200 kg / h of isopropanol, and fed to a distillation column, not shown in the figure, separated in a manner known in the art, the fatty alcohol from the isopropanol by distillation and Both substances are obtained as pure substances.
  • the invention provides a process by means of which desirable chemical raw materials, namely fatty alcohols and short-chain alkanols, can be obtained jointly and with high added value, since the raw material used is low-quality waste. greasy and waste oils are used.
  • the auxiliaries and catalysts used are commercially available and therefore readily available.
  • the process is characterized by a high degree of flexibility with regard to the waste greases and waste oils to be processed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé pour l'obtention d'alcools gras biodégradables de haute qualité à partir de déchets de graisses et/ou d'huiles. Dans un premier temps, les déchets d'huiles ou de graisses sont décomposés par hydrolyse. L'acide gras ainsi obtenu est purifié et ensuite transformé par une réaction avec des alcènes à chaîne courte, en esters d'alkyle d'acide gras qui, après une nouvelle purification, sont décomposés par hydrolyse en alcools gras et en alcanols. En plus des alcools gras, on obtient ainsi des alcanols comme produits dérivés recherchés.
PCT/EP2012/000269 2011-02-23 2012-01-21 Procédé pour l'obtention d'alcools gras a partir de déchets de graisses ou d'huiles Ceased WO2012113495A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011012177.3 2011-02-23
DE201110012177 DE102011012177A1 (de) 2011-02-23 2011-02-23 Verfahren zum Gewinnen von Fettalkoholen aus Abfallfetten oder Abfallölen

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WO2012113495A1 true WO2012113495A1 (fr) 2012-08-30

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PCT/EP2012/000269 Ceased WO2012113495A1 (fr) 2011-02-23 2012-01-21 Procédé pour l'obtention d'alcools gras a partir de déchets de graisses ou d'huiles

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WO (1) WO2012113495A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116354794A (zh) * 2021-12-28 2023-06-30 中国石油天然气股份有限公司 一种脂肪酸酯加氢反应制备脂肪醇的方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3425758C2 (de) 1983-07-14 1994-06-23 Oleofina Sa Verfahren zur Herstellung von Alkoholen
EP0454704B1 (fr) 1989-01-17 1994-09-28 DAVY McKEE (LONDON) LIMITED Procede de production d'alcools gras
DE4335781A1 (de) 1993-10-20 1995-04-27 Henkel Kgaa Verfahren zur Herstellung von Fettalkoholen auf pflanzlicher Basis
EP0737664B1 (fr) 1995-04-11 1998-01-28 Metallgesellschaft Ag Procédé de production d'ester cireux et d'hydrogénation de l'ester cireux en alcool gras
US20040133049A1 (en) * 1998-10-07 2004-07-08 Christian Pelzer Process for the continous fixed-bed hydrogenation of fatty acids and fatty acid esters
DE102008008872A1 (de) * 2008-02-13 2009-08-27 Lurgi Gmbh Verfahren zum Herstellen von Fettalkoholen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2306586B2 (de) * 1973-02-10 1978-08-24 Hoechst Ag, 6000 Frankfurt Verfahren zur kontinuierlichen Herstellung von Isopropylestern

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3425758C2 (de) 1983-07-14 1994-06-23 Oleofina Sa Verfahren zur Herstellung von Alkoholen
EP0454704B1 (fr) 1989-01-17 1994-09-28 DAVY McKEE (LONDON) LIMITED Procede de production d'alcools gras
DE4335781A1 (de) 1993-10-20 1995-04-27 Henkel Kgaa Verfahren zur Herstellung von Fettalkoholen auf pflanzlicher Basis
EP0737664B1 (fr) 1995-04-11 1998-01-28 Metallgesellschaft Ag Procédé de production d'ester cireux et d'hydrogénation de l'ester cireux en alcool gras
US20040133049A1 (en) * 1998-10-07 2004-07-08 Christian Pelzer Process for the continous fixed-bed hydrogenation of fatty acids and fatty acid esters
DE102008008872A1 (de) * 2008-02-13 2009-08-27 Lurgi Gmbh Verfahren zum Herstellen von Fettalkoholen

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116354794A (zh) * 2021-12-28 2023-06-30 中国石油天然气股份有限公司 一种脂肪酸酯加氢反应制备脂肪醇的方法

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Publication number Publication date
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