WO2010061702A1 - Procédé de fabrication d'un ester d'acide gras - Google Patents

Procédé de fabrication d'un ester d'acide gras Download PDF

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Publication number
WO2010061702A1
WO2010061702A1 PCT/JP2009/068197 JP2009068197W WO2010061702A1 WO 2010061702 A1 WO2010061702 A1 WO 2010061702A1 JP 2009068197 W JP2009068197 W JP 2009068197W WO 2010061702 A1 WO2010061702 A1 WO 2010061702A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
oil
acid ester
reaction
fats
Prior art date
Application number
PCT/JP2009/068197
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English (en)
Japanese (ja)
Inventor
淳 安孫子
真 上山
Original Assignee
国立大学法人京都工芸繊維大学
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Priority to JP2010540429A priority Critical patent/JPWO2010061702A1/ja
Publication of WO2010061702A1 publication Critical patent/WO2010061702A1/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
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • 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 present invention relates to a method for producing a fatty acid ester by transesterification using fats and oils as a raw material.
  • Biodiesel fuel compared to conventional petroleum diesel fuel (light oil), (1) The exhaust gas when burned is about 75% cleaner, (2) 10-20% reduction in emissions of carbon monoxide, hydrocarbons, particulate matter, etc. (3) The exhaust gas does not contain sulfur oxides or sulfates, (4) It has many advantages such as high lubrication performance.
  • Biodiesel fuel uses natural fats and oils derived from animals and plants, so even if it is used as a fuel, it has zero load for carbon dioxide production and is an environmentally friendly fuel.
  • This fuel has the advantage that it can be used as it is without modification to any diesel engine.
  • waste edible oil that contributes to environmental pollution can also be used as a raw material, it is a biomass raw material that can double the environmental burden.
  • biodiesel fuel mixed with petroleum-based diesel fuel we have already started using 1 to 20% biodiesel fuel mixed with petroleum-based diesel fuel, and that alone reduces the load on the engine due to its high lubricity and is environmentally friendly. It has been reported that the burden on health and health has also been reduced.
  • Patent Document 1 a method using a composite oxide having a perovskite type structure such as CaTiO 3 and CaMnO 3 as a heterogeneous solid catalyst for direct production of biodiesel fuel (Patent Document 1), alcohol in a supercritical state
  • Patent Document 2 a method using alkaline earth metal oxide, hydroxide or carbonate in a subcritical state
  • Patent Document 3 a method using quick lime or bitter lime
  • Patent Document 4 a method using quick lime or bitter lime
  • calcium hydroxide or calcium oxide A method to be used (Patent Document 4) has been proposed.
  • these methods have problems such as requiring high temperature and high pressure, difficulty in regenerating the catalyst, expensive catalyst, and insufficient reaction rate.
  • Patent Document 6 Also known is a method (Patent Document 6) in which triglyceride and alcohol are reacted in the presence of a solid acid catalyst such as a composite metal compound, metal sulfate, heteropolyacid, synthetic zeolite, or ion exchange resin.
  • a solid acid catalyst such as a composite metal compound, metal sulfate, heteropolyacid, synthetic zeolite, or ion exchange resin.
  • the method of Patent Document 6 has an advantage that the fatty acid soap is not produced as a by-product without pretreatment of free fatty acids in fats and oils, but the activity of the acid catalyst for transesterification is lower than that of the alkali catalyst. There was a problem that the reaction rate was small and not practical.
  • the present invention eliminates the need for a catalyst separation process, and allows the fatty acid ester to be produced efficiently and at low cost by allowing the ester exchange reaction to proceed at a high reaction rate under mild conditions.
  • An object of the present invention is to provide a manufacturing method.
  • the method for producing a fatty acid ester according to the present invention is a method for producing a fatty acid ester by an ester exchange reaction between fats and oils and using an organic onium hydrogen sulfate as a catalyst. .
  • natural fats and oils synthetic fats and oils, synthetic triglycerides, synthetic triglycerides containing monoglycerides and / or diglycerides, modified products thereof, or waste oils and fats containing these can be used as fats and oils.
  • alcohol having 1 to 8 carbon atoms or methyl cellosolve can be used as the alcohol.
  • ammonium, nitrogen-containing heterocyclic compounds, or phosphonium hydrogen sulfate can be used as the organic onium hydrogen sulfate. More preferably, either dichloroanilinium hydrogensulfate or trichloroanilinium hydrogensulfate can be used.
  • a triflate salt having a fluorine-containing sulfonic acid as an anion is known as a conventional organic onium salt, but it is expensive because a fluorine-containing sulfonic acid is used.
  • the organic onium hydrogensulfate used as a catalyst in the present invention uses a hydrogensulfate anion as an anion, and therefore can be produced using sulfuric acid as a raw material, so that it is produced at a lower cost than a triflate salt. be able to. Thereby, manufacture of biodiesel oil can be performed at lower cost.
  • the organic onium hydrogen sulfate of the present invention has the same performance as the conventional triflate salt. That is, the organic onium hydrogen sulfate salt of the present invention is used by dissolving in alcohol, but at the time of reaction, its catalytic action is expressed at the two-layer interface between fat and alcohol and dissolved in the glycerin produced after the reaction. Therefore, after recovering fatty acid ester, glycerin, and alcohol by distillation, they can remain in the reaction vessel as a residue. Therefore, the following reaction can be performed by adding a new fat and alcohol to the reaction vessel. This eliminates the need for a catalyst separation step, unlike the conventional soaking alkali catalyst method.
  • fatty acid soap is not produced. Moreover, the production amount of fatty acid ester per time is large. Moreover, it is possible to use fats and oils at high concentration. Thereby, compared with the past, fatty acid ester can be manufactured more efficiently.
  • An organic onium cation is a cation generated by coordination bonding of a proton or another cation to a lone electron pair in a compound containing an element having a lone electron pair.
  • R 1 to R 4 are each independently a hydrogen atom, or a linear or branched aliphatic hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon which may have a substituent. Represents a group or a heterocyclic group.
  • A represents a nitrogen atom or a phosphorus atom.
  • One to three of R 1 to R 4 may be a hydrogen atom.
  • X ⁇ represents a hydrogen sulfate anion.
  • Examples of the linear or branched aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group.
  • Examples of the alicyclic hydrocarbon group include a cycloalkyl group.
  • Examples of the aromatic hydrocarbon group include an aryl group and an aralkyl group.
  • Examples of the heterocyclic group include nitrogen-containing monocyclic or condensed ring compounds.
  • Examples of the substituent such as the aliphatic hydrocarbon group include a halogen atom. Preferred is a fluorine atom.
  • organic onium cations include the following nitrogen cations.
  • Tetraalkylammonium such as triethylammonium, triethylammonium, ethyldimethylammonium, diethylmethylammonium, tetramethylammonium, tetraethylammonium, tetra-n-propylammonium, tetraisopropylammonium, tetra-n-butylammonium, anilinium, diphenylammonium, tetra Aromatic ammonium such as phenylammonium, alicyclic ammonium such as N, N-dimethylpyrrolidinium, N, N-dimethylpiperidinium, N, N-dimethylmorpholinium, pyridinium, pyrazolium, N-methylimidazolium And nitrogen-containing heterocyclic compounds such as N-methylpyridinium.
  • nitrogen-containing heterocyclic compounds may contain a substituent such as an alkyl group, an aralkyl group, a halogen group, or an alkoxy group.
  • a substituent such as an alkyl group, an aralkyl group, a halogen group, or an alkoxy group.
  • Anilinium, pyrazolium and N-methylimidazolium are preferred.
  • the anilinium is preferably a fluorine-substituted product or a chlorine-substituted product, specifically pentafluoroanilinium, dichloroanilinium or trichloroanilinium. More preferably, it is a chlorine substitution product, and is dichloroanilinium or trichloroanilinium.
  • the reason why the chlorine substitution product of anilinium is preferable is as follows.
  • the reaction solution is cooled after completion of the reaction, it is separated into an upper layer containing glycerin and methanol and a lower layer containing a fatty acid ester.
  • the organic onium salt is dissolved in the lower layer and both layers are in a cloudy state, thereby achieving two-layer separation. It took at least one day to complete.
  • the chlorine substitution product of anilinium is used, two-layer separation can be achieved in a short time of about 1 hour. Therefore, since recovery of the fatty acid ester from the reaction solution can be performed in a short time, the manufacturing cost can be further reduced.
  • a phosphorus cation examples thereof include triarylphosphonium, aryldialkylphosphonium, diarylalkylphosphonium, and trialkylphosphonium. Preferred is triarylphosphonium, specifically triphenylphosphonium.
  • the organic onium salt used in the present invention catalyzes the transesterification reaction as a Brensted acid, the smaller the pKa (the stronger the acidity), the better. Therefore, hydrogen sulfate ions are used as anions.
  • the organic onium salt of the present invention is not particularly limited as long as it is a combination of the above-described nitrogen cation or phosphorus cation and a hydrogen sulfate anion, but preferably comprises dichloroaniline (regardless of the substitution position) and a hydrogen sulfate anion. It is a trichloroanilinium hydrogensulfate composed of dichloroanilinium hydrogensulfate, trichloroaniline (regardless of the substitution position) and a hydrogensulfate anion.
  • dichloroanilinium hydrogensulfate and trichloroanilinium hydrogensulfate More preferred are dichloroanilinium hydrogensulfate and trichloroanilinium hydrogensulfate, and more preferred are 2,4-dichloroanilinium hydrogensulfate and 2,5-dichloroanilinium hydrogensulfate.
  • the catalyst concentration with respect to fats and oils is 0.1 to 30 mol%, more preferably 0.1 to 10 mol%.
  • the catalyst concentration affects the reaction temperature and reaction time, and can be appropriately selected within the above range. For example, when the catalyst is used at 10 mol% with respect to the fat and oil, methanol is used as the alcohol and the reaction temperature is 60 ° C., the conversion rate of the fat becomes 100% in 24 hours. %, When methanol is used as the alcohol and the reaction temperature is 130 ° C., the conversion of fats and oils becomes 100% in 4 hours. That is, since the reaction is a pseudo-primary reaction that completely depends on the amount of catalyst, the temperature and the time required for the reaction have an inversely proportional relationship.
  • the fats and oils used in the present invention are not particularly limited, and may be natural fats and oils, synthetic fats and oils, or a mixture thereof.
  • fats and oils components other than fats and oils may be mixed. Specifically, crude oil, heavy oil, light oil, mineral oil, essential oil, coal, fatty acid, sugar, metal powder, metal salt, protein, amino acid, hydrocarbon, cholesterol, flavor, pigment compound, enzyme, perfume, alcohol, fiber, Resins, rubbers, paints, cements, detergents, aromatic compounds, aliphatic compounds, soot, glass, earth and sand, nitrogen-containing compounds, sulfur-containing compounds, phosphorus-containing compounds, halogen-containing compounds, etc. It is not limited. These foreign components are preferably used after being removed by sedimentation, filtration, liquid separation or the like. In addition, about water
  • Alcohols used in the present invention are not particularly limited, but are alcohols having a saturated linear or branched aliphatic hydrocarbon skeleton. Preferred are alcohols having 1 to 8 carbon atoms, more preferably 1 to 5 carbon atoms. Furthermore, you may have a halogen atom and an ether group as a substituent. For example, methanol, ethanol, n-propanol, isopropanol, n-butanol, t-butanol, n-pentanol, methyl cellosolve and the like can be mentioned. These alcohols can be used alone or in admixture of two or more.
  • any one of methanol, ethanol and methyl cellosolve is used. This is because it is easily available and the availability of the resulting fatty acid ester is high.
  • alcohols act as a reaction substrate for subjecting fats and oils to alcoholysis (transesterification reaction), and also act as a solvent for adjusting the dilution and viscosity of fats and oils.
  • [4] Molar ratio of fats and oils and alcohols There is no particular limitation as long as the molar ratio of fats and fats and alcohols used as a reaction substrate (fats / alcohols) is 1/1 or more, but preferably 1 / 20 to 1/2, more preferably 1/15 to 1/3, and still more preferably 1/10 to 1/3.
  • the reaction becomes a secondary reaction, the time required for the completion of the reaction becomes long, and when the molar ratio of fats and oils to alcohols is large (for example, 1/10) ) The reaction becomes a false primary reaction, and the reaction can be completed in a short time.
  • fats and oils and alcohol should just exist as a mixture of both, and if sufficient stirring is made, it is not necessary to form a uniform phase in particular.
  • the molar ratio of fats and oils to alcohols is represented by the number of moles of alcohol per ester in the fats and oils.
  • the reaction temperature is from room temperature to 200 ° C, more preferably from 60 to 130 ° C.
  • the reaction is a secondary reaction or a pseudo-primary reaction depending on the molar ratio of fats and alcohols to be used. Therefore, the higher the reaction temperature, the faster the reaction rate can be obtained, but the reaction is preferably carried out at 60 to 130 ° C.
  • the reaction time depends on the reaction temperature and the amount of catalyst used. For example, when the reaction temperature is 60 ° C., 10 mol% of the catalyst is used with respect to the fat and oil, and methanol is used as the alcohol, the conversion rate of the fat and oil becomes 100% in 24 hours. On the other hand, when the reaction temperature is 130 ° C., 1 mol% of the catalyst is used with respect to the oil and fat, and when methanol is used as the alcohol, the conversion of the oil and fat becomes 100% in 4 hours. Therefore, the reaction time can be appropriately selected depending on the catalyst concentration and the reaction temperature.
  • the reaction pressure is not particularly limited. Although it is convenient in terms of operation to carry out under normal pressure, the pressure may be increased to about 1 to 10 atm if necessary. When using a low-boiling point alcohol, it is desirable to carry out the reaction under pressure in a sealed container in order to ensure a desired reaction temperature.
  • the type of reaction apparatus for carrying out the present invention is not particularly limited. Depending on the reaction method such as a batch method or a continuous method, the reaction can be performed using a stirring tank, a fluidized bed reactor, a shaking reactor, or the like.
  • alcohols and glycerin can be recovered by direct distillation after completion of the reaction, and a fatty acid ester can be recovered without using a phase separation operation.
  • the catalyst remains in the reaction vessel as a distillation residue. Thereby, new fats and oils and alcohols can be added and the next reaction can be performed, and the catalyst can be reused.
  • the catalyst can be purified by recrystallization and reused as necessary.
  • Example 1 Oil and fat (Nissin Food Formulation, 10.41 g), methanol (Wako Pure Chemical Grade 1, 30 ml), 2,4-dichloroanilinium hydrogensulfate catalyst [28.5 mg (1.14 mol%)] and stir bar It put into the reaction container (made by a pressure
  • the lower layer (hereinafter referred to as FAME) was separated and the residual methanol was removed using an evaporator, and then the yield and conversion were analyzed by NMR. Yield 8.49 g (85%), conversion 100%, glycerin content ⁇ 0.1%.
  • Example 2 The same procedure as in Example 1 was conducted, except that 26.2 mg (1.05 mol%) of 2,5-dichloroanilinium hydrogen sulfate was used. The two layers separated by standing for 1 hour. FAME was isolated and analyzed. Yield 6.35 g (63%), conversion 100%, glycerin content ⁇ 0.1%.
  • Example 3 The same procedure as in Example 1 was performed except that 2,4,6-trichloroanilinium hydrogen sulfate (33.0 mg, 1.15 mol%) was used. The two layers separated by standing for 1 hour. FAME was isolated and analyzed. Yield 5.03 g (50%), conversion 100%, glycerin content ⁇ 0.1%.
  • Example 4 The same procedure as in Example 1 was conducted except that 40.0 mg (1.00 mol%) of triphenylphosphonium hydrogen sulfate was used as the catalyst. The two layers separated by standing for 1 hour. FAME was isolated and analyzed. Yield 7.34 g (73%), conversion 100%, glycerin content ⁇ 0.1%.
  • Example 1 The same procedure as in Example 1 was conducted except that 2,5-dichloroanilinium triflate (21.0 mg, 1.05 mol%) was used as the catalyst. The two layers separated by standing for 1 hour. FAME was isolated and analyzed. Yield 7.13 g (71%), conversion 100%, glycerin content ⁇ 0.1%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention porte sur un procédé de fabrication d'un ester d'acide gras, suivant lequel un acide gras peut être produit de manière efficace à faible coût par la mise en œuvre d'une réaction de transestérification à une vitesse de réaction élevée dans des conditions douces sans avoir besoin d'un procédé de séparation de catalyseur. Dans le procédé, suivant lequel un ester d'acide gras est produit par une réaction de transestérification entre un alcool et une matière grasse ou une huile, un hydrogénosulfate d'un composé onium organique est utilisé comme catalyseur. Dans la mesure où l'hydrogénosulfate permet de produire un ester d'acide gras de façon plus efficace à l'aide d'acide sulfurique comme matière de départ, le coût de fabrication peut être réduit par comparaison avec les sels triflates classiques.
PCT/JP2009/068197 2008-11-28 2009-10-22 Procédé de fabrication d'un ester d'acide gras WO2010061702A1 (fr)

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JP2010540429A JPWO2010061702A1 (ja) 2008-11-28 2009-10-22 脂肪酸エステルの製造方法

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1696248A (zh) * 2005-07-08 2005-11-16 中国科学院过程工程研究所 基于离子液体的生物柴油合成方法
WO2009114830A2 (fr) * 2008-03-14 2009-09-17 University Of Hawaii Procédés et compositions pour extraction et transestérification de composants de biomasse

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1696248A (zh) * 2005-07-08 2005-11-16 中国科学院过程工程研究所 基于离子液体的生物柴油合成方法
WO2009114830A2 (fr) * 2008-03-14 2009-09-17 University Of Hawaii Procédés et compositions pour extraction et transestérification de composants de biomasse

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 145, no. 16, 2006, Columbus, Ohio, US; abstract no. 316935N, page 1426; *
LI, HUAIPING: "Preparation of biodiesel from rapeseed oil catalyzed by ionic liquid [Hmim] HS04", ZHONGGUO YOUZHI, vol. 33, no. 4, April 2008 (2008-04-01), pages 57 - 59 *
WU, QIN: "Transesterification of Cottonseed Oil Catalyzed by Bronsted Acidic Ionic Liquids", IND. ENG. CHEM. RES., vol. 46, no. 24, 2007, pages 7955 - 7960 *

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