WO2008023728A1 - Procédé de production d'un ester d'acide gras à partir d'une huile végétale, et carburant diesel comprenant l'ester d'acide gras - Google Patents

Procédé de production d'un ester d'acide gras à partir d'une huile végétale, et carburant diesel comprenant l'ester d'acide gras Download PDF

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Publication number
WO2008023728A1
WO2008023728A1 PCT/JP2007/066261 JP2007066261W WO2008023728A1 WO 2008023728 A1 WO2008023728 A1 WO 2008023728A1 JP 2007066261 W JP2007066261 W JP 2007066261W WO 2008023728 A1 WO2008023728 A1 WO 2008023728A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
acid ester
oil
vegetable oil
reaction
Prior art date
Application number
PCT/JP2007/066261
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English (en)
Japanese (ja)
Inventor
Kazutoshi Ikenaga
Original Assignee
Biomass Japan Inc.
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 Biomass Japan Inc. filed Critical Biomass Japan Inc.
Priority to JP2008530937A priority Critical patent/JPWO2008023728A1/ja
Publication of WO2008023728A1 publication Critical patent/WO2008023728A1/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
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Definitions

  • the present invention relates to a method for producing a fatty acid ester from vegetable oil, and a diesel fuel containing the fatty acid ester.
  • Vegetable oil is composed of fatty acid triglycerides, and it has long been known that fatty acid methyl esters obtained by transesterifying glycerol with methanol can be used as diesel fuel. Due to the recent rise in crude oil prices and environmental issues, this fatty acid ester is notable from petroleum as a raw material, and is attracting attention as a biodiesel fuel!
  • biodiesel fuel In Europe, efforts are being made on biodiesel fuel using rapeseed as a raw material, and biodiesel fuel exceeding 2 million kl has already been produced. In the United States, biodiesel fuel made from soybeans is produced. In Japan, edible oil, especially biodiesel fuel made from waste edible oil, has been commercialized.
  • caustic soda caustic potash as a catalyst as disclosed in JP-A-10-245586.
  • alkali metal substances used as catalysts in this method react with fatty acids to form metal soaps when the reaction temperature is high, or when the catalyst content is high or the water content is high, and the viscosity of biodiesel fuel is increased. This may cause troubles such as an increase in the temperature or deposition of alkali metal substances on the fuel filter or spark plug.
  • JP-A-61-254255 As a method that does not require such a neutralization step, as disclosed in JP-A-61-254255, methanol-insoluble alkali metalation such as sodium carbonate and sodium hydrogen carbonate is possible. It has been proposed to use the compound as a heterogeneous solid catalyst. However, this method requires about 1 to 2 hours for the reaction as described in the examples of JP-B 61-254255, and is not an efficient method.
  • JP 2001-271090 uses calcium hydroxide or calcium oxide as a catalyst, and a reaction temperature of 90 °. It has been disclosed that the reaction time can be shortened to 5-30 minutes by raising the temperature to C-240 ° C, but this method requires heating the reaction system in order to carry out the reaction at a high temperature, It must be said that this is a disadvantageous method in terms of thermal energy.
  • Japanese Patent Application Laid-Open No. 2005-060591 discloses a method of performing a reaction without using a catalyst using supercritical conditions. This method has the advantage that there is no need to add a catalyst and the reaction time required is S4 ⁇ ; as short as 12 minutes. In this method, the reaction system must be 370 to 500 ° C. This means that the thermal energy to produce per unit weight of biodiesel fuel is large! /, Which is desirable and not the method! /.
  • An object of the present invention is to provide a method for producing a fatty acid ester from a vegetable oil in which the disadvantages of the prior art are eliminated, and a diesel fuel containing the fatty acid ester. That is, an object of the present invention is to provide a method for producing a fatty acid ester from a vegetable oil in a short reaction time, and a diesel fuel containing the fatty acid ester. Another object of the present invention is to provide a method for producing a fatty acid ester from a vegetable oil that does not require a neutralization step, and a diesel fuel containing the fatty acid ester. Another object of the present invention is to provide a method for producing a fatty acid ester from a vegetable oil advantageous in terms of heat energy, and a diesel fuel containing the fatty acid ester.
  • the present invention relates to a method for producing an alcohol and a vegetable oil-powered fatty acid ester, wherein the alcohol and the vegetable oil are reacted in the presence of an alkali metal phosphate. It is a manufacturing method. Further, the present invention is a method for producing a fatty acid ester from the above plant oil which is an alkali metal phosphate strength potassium phosphate hydrate.
  • the present invention is a method for producing a fatty acid ester from the above-mentioned plant oil which is an alkali metal phosphate strength tripotassium phosphate aqueous solution.
  • this invention is a method of manufacturing fatty acid ester from said vegetable oil whose vegetable oil is waste edible oil.
  • the present invention is a method for producing a fatty acid ester from the above vegetable oil which is alcoholic methanol or ethanol.
  • the present invention is a method for producing a fatty acid ester from the above vegetable oil, wherein the reaction is performed while irradiating with microwaves.
  • the present invention is a diesel fuel containing a fatty acid ester produced by any one of the production methods described above.
  • the production method of the present invention has shortened the problem of a long reaction time when producing a fatty acid ester from vegetable oil, and has made it possible to carry out the reaction quickly.
  • a special pressurizing apparatus is not required, and the process can be carried out with a simple apparatus.
  • the production method of the present invention does not require a neutralization step, and is an economically advantageous method for producing biodiesel fuel.
  • the biodiesel fuel produced by the method of the present invention has a small amount of metal components, particularly metal soap, it is difficult to damage the diesel engine.
  • vegetable oil is used as a reaction raw material.
  • vegetable oils include Amani oil, castor oil, tung oil, olive oil, cacao oil, canola oil, sesame oil, rice bran oil, corn oil, safflower oil, salad oil, soybean oil, rapeseed oil, palm oil, Peanut oil, safflower oil, coconut oil, cottonseed oil, etc. can be mentioned.
  • edible oils used for food processing for example, production of fried foods and discarded, are preferable from the viewpoint of cost or environment.
  • Such edible oils include, for example, olive oil, cacao oil, canola oil, sesame oil, rice bran oil, corn oil, safflower oil, sarah Examples include oil, soybean oil, rapeseed oil, palm oil, peanut oil, safflower oil, and coconut oil.
  • the above-mentioned vegetable oil is a triglyceride in which glycerin and three higher fatty acids are ester-bonded.
  • Higher fatty acids forming such vegetable oils are fatty acids having 12 to 18 carbon atoms, such as saturated fatty acids such as lauric acid, myristic acid, normitic acid and stearic acid, and monovalent unsaturated compounds such as oleic acid. Examples thereof include polyunsaturated fatty acids such as fatty acids, linoleic acid and linolenic acid, and mixtures thereof.
  • fatty acid ester examples include glycerin palmitic acid ester, glycerin stearic acid ester, glycerin linoleic acid ester, and glycerin linolenic acid ester.
  • the fatty acids in the glycerin fatty acid diester and the glycerin fatty acid triester may be the same or different.
  • the fatty acid glycerol ester and alcohol are reacted to produce a fatty acid lower alcohol ester.
  • the alcohol used in the production method of the present invention include methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, pentanol, hexanol, Examples include cyclohexanol and heptanol. Of these, methanol is preferred, and methanol is particularly preferred.
  • the present invention is characterized in that an alkali metal phosphate is used as a catalyst in a method for producing a fatty acid ester from a vegetable oil.
  • the alkali metal in the present invention refers to a metal such as lithium, sodium, potassium, norevidium and cesium. Among these, potassium is preferable because it has the most excellent catalytic effect among sodium and potassium, which are relatively inexpensive.
  • alkaline metal phosphate used as a catalyst for transesterification in the production method of the present invention, specifically, potassium phosphate (K 3 PO 4), sodium phosphate, phosphorus Acid
  • the reaction catalyst used in the present invention includes the above-mentioned aqueous solution of alkali metal phosphoric acid, such as tripotassium phosphate aqueous solution. I ’ll use the power S.
  • the amount of alkali metal phosphate used as a catalyst is preferably in the range of 0.01 to 5 parts by weight based on the power of rhodium per 100 parts by weight of vegetable oil. A range of 3 parts by weight is more preferred.
  • the alkali metal phosphate used as the transesterification reaction catalyst does not dissolve in alcohol. Therefore, when dispersing the catalyst in alcohol, It is preferable to prepare a fine powder of alkali metal phosphate in advance or add it to the reaction system as an aqueous solution in which the alkali metal phosphate is dissolved in a small amount of water.
  • a microwave is used to produce a fatty acid ester from a vegetable oil, and preferably to promote an ester exchange reaction.
  • Microwaves are high-frequency radio waves with a frequency of about 100 MHz to 100 GHz. In Japan, use of 2450 MHz is generally approved for home use.
  • a device for generating microwaves for example, a variety of continuous microwave generation and processing devices having a conveying unit such as a known batch type or a belt conveyor can be used.
  • the container for containing the reaction raw material consisting of vegetable oil / alcohol is made of glass, ceramic or fluororesin.
  • a quartz glass or heat-resistant glass window may be partially provided, and a microphone mouth wave oscillating part may be attached thereto to irradiate the inside of the reactor. It is also possible to use a device that conducts microwaves from the oscillator through a metal conduit.
  • the method for producing a fatty acid ester from the vegetable oil of the present invention will be described step by step with respect to a case using waste edible oil as a raw material.
  • impurities are first removed from the recovered waste edible oil.
  • solid impurities are removed with a wire mesh, a filter, or the like.
  • Moisture is allowed to stand and phase-separated for removal.
  • moisture forms a lower layer, which is removed. If necessary, centrifuge to remove impurities.
  • the vegetable oil and alcohol are first charged into the reactor.
  • Weight of vegetable oil vs. alcohol used for reaction The ratio is usually 10 to 100 parts by weight, preferably 100 to 100 parts by weight, preferably 30 to 70 parts by weight with respect to 100 parts by weight of vegetable oil! /.
  • Alcohol phosphate which is a transesterification reaction catalyst, is added and dispersed in advance in alcohol or vegetable oil, or in the mixture after charging with vegetable oil / alcohol.
  • a method of dispersing the catalyst a method of supplying and dispersing the alkali metal phosphate little by little while stirring the alcohol is preferable.
  • a disperser such as an ultrasonic generator! /.
  • the temperature condition for the reaction is preferably 40 ° C to 90 ° C, particularly 60 to 80 ° C.
  • atmospheric pressure is preferable as the pressure condition in the reaction vessel for reacting the vegetable oil and the alcohol.
  • the time for reacting the vegetable oil and the alcohol is preferably in the range of 1 minute to 60 minutes, more preferably in the range of 2 minutes to 30 minutes. In particular, the range of 3 minutes to 15 minutes is most preferable.
  • the above-mentioned alcohol / vegetable oil mixture is preferably irradiated with microwaves.
  • the reaction format may be either a continuous reaction system or a batch system.
  • the alcohol / vegetable oil mixture is usually subjected to the reaction in a state where it is contained in a container that does not absorb microwaves, for example, a container made of glass, ceramic and fluororesin.
  • the reaction time is preferably in the range of 1 minute to 30 minutes. 1. The range of 5 minutes to 15 minutes is more preferable. In particular, the range of 2 minutes to 10 minutes is most preferable.
  • fatty acid lower alcohol ester and glycerin are obtained.
  • the fatty acid ester is separated into the upper layer and dariserine is separated into the lower layer. Separation of glycerin can be performed by a method such as centrifugation.
  • the upper layer is taken out, the catalyst and other impurities are removed, and the product is dried with a desiccant.
  • a catalyst comprising an alkali metal phosphate used in the transesterification reaction in the present invention is insoluble in alcohol. This catalyst must be separated after the transesterification reaction. The catalyst can be separated by various filters, centrifugation, or the like. Also separate By washing the fatty acid ester with water, the catalyst can be dissolved in water, preferably warm water, and separated by force S.
  • the fatty acid ester produced as described above may be used alone or in combination with other components in fuels such as diesel fuel, lubricating base oils, fuel oil additives, etc., depending on the application requirements. Use with power S.
  • potassium phosphate hydrate powder K PO ⁇ ⁇ ⁇
  • Example 1 the same procedure as in Example 1 was performed except that the reaction time was changed from 3 minutes to 5 minutes. The results are shown in Table 1.
  • Example 1 the reaction was performed in the same manner as in Example 1 except that the reaction time was changed from 3 minutes to 10 minutes. The results are shown in Table 1.
  • Example 1 the reaction was performed in the same manner as in Example 1 except that the reaction time was changed from 3 minutes to 15 minutes. The results are shown in Table 1. [0035] [Example 5]
  • Example 4 the same procedure as in Example 4 was carried out except that the amount of potassium phosphate hydrate as the catalyst was about 1 ⁇ 2. The results are also shown in Table 1.
  • Example 1 the same procedure as in Example 1 was carried out except that the amount of potassium phosphate hydrate as the catalyst was about 1/7 and the reaction time was 45 minutes. The results are also shown in Table 1.
  • Waste cooking oil 100 parts by weight, methanol 67 parts by weight, tripotassium phosphate hydrate (K PO ⁇ ⁇
  • the production method of the present invention can reduce the time required for fatty acid ester production and can be produced with a simple apparatus that can eliminate the neutralization step. Therefore, the production method of biodiesel fuel is more economical. As useful.
  • FIG. 1 is a schematic view showing an example of an apparatus used in the production method of the present invention.
  • FIG. 2 is a photograph showing an example of an apparatus used in the production method of the present invention.
  • FIG. 3 is a photograph showing an example of an apparatus used in the production method of the present invention.
  • FIG. 4 is a photograph showing an example of an apparatus used in the production method of the present invention.

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

Abstract

L'invention concerne un procédé de production d'un ester d'acide gras en effectuant la transestérification d'une huile végétale rapidement dans un appareil simple. Ce procédé de production d'un ester d'acide gras à partir d'une huile végétale est caractérisé en ce que l'on fait réagir un alcool avec une huile végétale en présence d'un phosphate de métal alcalin. L'invention concerne également un carburant diesel produit par ce procédé.
PCT/JP2007/066261 2006-08-25 2007-08-22 Procédé de production d'un ester d'acide gras à partir d'une huile végétale, et carburant diesel comprenant l'ester d'acide gras WO2008023728A1 (fr)

Priority Applications (1)

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JP2008530937A JPWO2008023728A1 (ja) 2006-08-25 2007-08-22 植物油から脂肪酸エステルを製造する方法および該脂肪酸エステルを含むディーゼル燃料

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JP2006-228654 2006-08-25
JP2006228654 2006-08-25

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009203346A (ja) * 2008-02-28 2009-09-10 Kagawa Industry Support Foundation 簡便な油脂類分解反応方法
JP2009262075A (ja) * 2008-04-25 2009-11-12 Ohbayashi Corp グリセリン副産物のリサイクル方法
JP2010013511A (ja) * 2008-07-02 2010-01-21 Esupekku:Kk バイオディーゼル燃料及びその製造方法
WO2010082527A1 (fr) * 2009-01-16 2010-07-22 富士フイルム株式会社 Procédé de fabrication d'un ester alkylique d'acide gras, et carburant diesel
JP2011046803A (ja) * 2009-08-26 2011-03-10 Kagawa Industry Support Foundation バイオディーゼル燃料の製造装置とバイオディーゼル燃料の製造方法
JPWO2015029148A1 (ja) * 2013-08-28 2017-03-02 株式会社日立製作所 化学物質の生産システム及び化学物質の生産方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007077347A (ja) * 2005-09-16 2007-03-29 Fujifilm Corp 脂肪酸アルキルエステルの製造方法及び燃料

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Publication number Priority date Publication date Assignee Title
JP4876111B2 (ja) * 2008-09-18 2012-02-15 富士フイルム株式会社 脂肪酸石鹸含有量の調整法

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Publication number Priority date Publication date Assignee Title
JP2007077347A (ja) * 2005-09-16 2007-03-29 Fujifilm Corp 脂肪酸アルキルエステルの製造方法及び燃料

Non-Patent Citations (2)

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Title
FILIPPIS ET AL: "Rapeseed Oil Transesterification Catalyzed by Sodium Phosphates", ENERGY & FUELS, vol. 19, no. 6, 2005, pages 2225 - 2228, XP003010535 *
MAZZOCCHIA ET AL: "Fatty acid methyl esters synthesis from triglyceride over heterogeneous catalysts in the presence of microwaves", COMPTES RENDUS CHIMIE, vol. 7, no. 6-7, 2004, pages 601 - 605, XP003021327 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009203346A (ja) * 2008-02-28 2009-09-10 Kagawa Industry Support Foundation 簡便な油脂類分解反応方法
JP2009262075A (ja) * 2008-04-25 2009-11-12 Ohbayashi Corp グリセリン副産物のリサイクル方法
JP2010013511A (ja) * 2008-07-02 2010-01-21 Esupekku:Kk バイオディーゼル燃料及びその製造方法
WO2010082527A1 (fr) * 2009-01-16 2010-07-22 富士フイルム株式会社 Procédé de fabrication d'un ester alkylique d'acide gras, et carburant diesel
JP2011046803A (ja) * 2009-08-26 2011-03-10 Kagawa Industry Support Foundation バイオディーゼル燃料の製造装置とバイオディーゼル燃料の製造方法
JPWO2015029148A1 (ja) * 2013-08-28 2017-03-02 株式会社日立製作所 化学物質の生産システム及び化学物質の生産方法

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