WO2009007234A1 - Nouveau procédé de fabrication d'esters à partir d'huiles végétales et/ou de graisses animales à l'aide de catalyseurs hétérogènes, en particulier en présence d'acidité libre et d'eau - Google Patents

Nouveau procédé de fabrication d'esters à partir d'huiles végétales et/ou de graisses animales à l'aide de catalyseurs hétérogènes, en particulier en présence d'acidité libre et d'eau Download PDF

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Publication number
WO2009007234A1
WO2009007234A1 PCT/EP2008/058030 EP2008058030W WO2009007234A1 WO 2009007234 A1 WO2009007234 A1 WO 2009007234A1 EP 2008058030 W EP2008058030 W EP 2008058030W WO 2009007234 A1 WO2009007234 A1 WO 2009007234A1
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WO
WIPO (PCT)
Prior art keywords
process according
reaction
acid
vegetable oils
animal fats
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
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PCT/EP2008/058030
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English (en)
Inventor
Luigi Siano
Luigi Cassar
Maurizio Guida
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ASER SRL
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ASER SRL
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Publication date
Application filed by ASER SRL filed Critical ASER SRL
Publication of WO2009007234A1 publication Critical patent/WO2009007234A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C11C3/003—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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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

Definitions

  • the present invention relates to a process for producing esters from vegetable oils and animal fats, particularly for producing biodiesel, which uses heterogeneous esterification and transesterification catalysts to produce esters by a reaction between vegetable oils or animal fats, aliphatic alcohols and dialkyl carbonates.
  • Biodiesel used as fuel in diesel engines, is constituted by a mixture of esters of fatty acids obtained by transesterification reaction of vegetable oils and animal fats with methanol or ethanol and subsequent separation from glycerin.
  • the transesterification reaction for producing biodiesel is performed generally by using as catalysts bases of alkaline metals such as for example NaOH, KOH, NaOCH 3 , KOCH 3 (1, 2).
  • Barium hydroxide dissolves, producing a substantially homogeneous catalyst, while calcium oxide produces suspensions (3). Suspensions of CaO make it difficult to separate the ester and glycerin phases.
  • ETS-10 are active in the transesterification reaction at temperatures below 125 0 C.
  • the activity of these catalysts is compromised by the presence of free acidity.
  • heterogeneous catalysts constituted by vanadyl phosphate dihydrate are active in partial oxidation reactions of hydrocarbons (8, 9). Vanadyl phosphates substituted with an M 3+ cation and supported on titania and silica have been tested in the partial oxidation reaction of propane (10). These catalysts, in addition to having remarkable redox properties, also have interesting Bronsted and Lewis acid properties.
  • the aim of the present invention is to provide a process which allows to produce biodiesel at lower costs than known processes even starting from oils which contain high free acidity and in the presence of water even derived from the esterification reaction.
  • An object of the present invention is to provide a process which has additional economic advantages, allowing to produce the byproduct of biodiesel, glycerin, with a higher degree of purity and therefore with a lower production cost.
  • Another object of the present invention is to provide a process in which the formation of surfactant species in solution, which by facilitating the formation of emulsions slow the step for separation of the glycerin and biodiesel, is limited, avoiding the need to neutralize the products and further avoiding the need for an operation for separating the glycerin from the residues of the homogeneous catalyst.
  • the process according to the present invention comprises in particular, among its stages, the mixing of vegetable oils or animal fats with aliphatic alcohols containing dialkyl carbonate, particularly dimethyl carbonate or diethyl carbonate, in a quantity which is at least stoichiometric with respect to the water plus the acid that is present in the mix, placing the mix in contact with the catalyst, and then heating to the reaction temperature.
  • dialkyl carbonate particularly dimethyl carbonate or diethyl carbonate
  • reaction stage of the process according to the present invention comprises the steps of:
  • the alcohol used can be for example an aliphatic monoalcohol, particularly an aliphatic monoalcohol which contains 1 to 5 carbon atoms, for example methanol or ethanol.
  • the heterogeneous catalyst used in the process according to the present invention can be a heterogeneous catalyst for the esterification and transesterification reaction of vegetable oils or animal fats, for example a heterogeneous catalyst selected from the group consisting of vanadyl phosphate dihydrate, supported TiO 2 , hydrotalcites, sulfuric acid, p- toluenesulfonic acid, styrene-based sulfonic resins, et cetera.
  • the process according to the present invention can be performed at a temperature which is suitable for the reaction, for example at a temperature from 50 to 200 0 C, in particular at a temperature around 60-120 0 C.
  • the weight ratio of alcohol/vegetable oil or animal fat used in the process according to the present invention is comprised for example from 0.5 and 5.
  • the reaction occurs in the presence of free fatty acids, even in high concentrations, for example higher than 10%.
  • reaction can occur discontinuously or continuously.
  • the dialkyl carbonate is used in a quantity which is at least stoichiometric with respect to the sum of the acidity that is present in the oil and of the water that is present in the system.
  • the heterogeneous catalysts can be separated by filtration, the unreacted aliphatic alcohol can be separated by distillation, and the glycerin phase can be separated by decantation from the ester phase.
  • the process according to the present invention can also comprise a further stage of transesterification of the unreacted glycerides that are present in the ester phase.
  • the reaction can be performed discontinuously or in continuous reactors, both of the agitated type and of the fixed-bed type.
  • the process according to the present invention allows cost reduction and allows to work in continuous plants.
  • the process according to the invention consists in mixing vegetable oils or animal fats with an aliphatic alcohol, preferably methanol and dialkyl carbonate, particularly dimethyl carbonate. The reaction mix is then heated to the reaction temperature and placed in contact with the catalyst.
  • an aliphatic alcohol preferably methanol and dialkyl carbonate, particularly dimethyl carbonate.
  • the dry resin dried beforehand in a stove at a temperature of 100 0 C, and the methanol were added to the oil, which was initially homogenized and heated to a temperature of approximately 40 0 C. The reaction occurred at the boiling point of methanol, 70 0 C.
  • the test was subsequently repeated by using the same catalyst as in the preceding test in order to assess its catalytic activity and its lifespan.
  • Example 2 Esterification of acid oil in the presence of acid resin, dimethyl carbonate and methanol as cosolvent at 70 0 C. a) Test conducted with acid resin, dimethyl carbonate and methanol at 7O 0 C
  • the esterification test was conducted at 100 0 C to assess the influence of the temperature on the elimination of acidity.
  • Example 3 Esterification of acid oil in the presence of the catalyst vanadyl phosphate dihydrate, VOP 4 ⁇ 2 H 2 O, methanol and dimethyl carbonate.
  • the catalyst is prepared as described in WO2007062825 that is incorporated herein by reference.
  • Example 4 Esterification of acid oil in the presence of TiO 2 /SiO 2 , methanol and dimethyl carbonate.
  • the powdered catalyst TiO 2 /SiO 2 is acidified with stearic acid.
  • conversion in the presence of a free acidity of 5% in OA is assessed.
  • Free acidity has an only partial effect on the catalyst, reducing its activity by approximately 27%.
  • the resulting conversion is determined by using H-NMR.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General 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 Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention porte sur un procédé de fabrication d'esters à partir d'huiles végétales ou de graisses animales. Ce procédé comporte l'étape de réaction d'estérification et/ou de transestérification des huiles végétales et/ou des graisses animales par au moins un alcool aliphatique en présence de catalyseurs hétérogènes, la réaction d'estérification et/ou de transestérification ayant lieu en présence d'un carbonate de dialkyle.
PCT/EP2008/058030 2007-07-09 2008-06-24 Nouveau procédé de fabrication d'esters à partir d'huiles végétales et/ou de graisses animales à l'aide de catalyseurs hétérogènes, en particulier en présence d'acidité libre et d'eau Ceased WO2009007234A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT001368A ITMI20071368A1 (it) 2007-07-09 2007-07-09 Nuovo processo per la produzione di esteri da oli vegetali e/o grassi animali con l'impiego di catalizzatori eterogenei, in particolare in presenza di acidita' libera e di acqua.
ITMI2007A001368 2007-07-09

Publications (1)

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WO2009007234A1 true WO2009007234A1 (fr) 2009-01-15

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PCT/EP2008/058030 Ceased WO2009007234A1 (fr) 2007-07-09 2008-06-24 Nouveau procédé de fabrication d'esters à partir d'huiles végétales et/ou de graisses animales à l'aide de catalyseurs hétérogènes, en particulier en présence d'acidité libre et d'eau

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IT (1) ITMI20071368A1 (fr)
WO (1) WO2009007234A1 (fr)

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010144597A1 (fr) * 2009-06-09 2010-12-16 Mcneff Research Consultants, Inc. Systèmes et procédés pour raffiner des compositions d'ester alkylique
US20110060153A1 (en) * 2006-08-04 2011-03-10 Mcneff Research Consultants, Inc. Systems and methods for refining alkyl ester compositions
US20110172450A1 (en) * 2006-08-04 2011-07-14 Mcneff Clayton V Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
US8017796B2 (en) 2007-02-13 2011-09-13 Mcneff Research Consultants, Inc. Systems for selective removal of contaminants from a composition and methods of regenerating the same
US8361174B2 (en) 2008-10-07 2013-01-29 Sartec Corporation Catalysts, systems, and methods for producing fuels and fuel additives from polyols
US8466305B2 (en) 2007-09-28 2013-06-18 Mcneff Research Consultants, Inc. Methods and compositions for refining lipid feed stocks
US8585976B2 (en) 2007-02-13 2013-11-19 Mcneff Research Consultants, Inc. Devices for selective removal of contaminants from a composition
US8642824B2 (en) 2007-08-09 2014-02-04 Elevance Renewable Sciences, Inc. Chemical methods for treating a metathesis feedstock
US8692006B2 (en) 2007-08-09 2014-04-08 Elevance Renewable Sciences, Inc. Thermal methods for treating a metathesis feedstock
US8735640B2 (en) 2009-10-12 2014-05-27 Elevance Renewable Sciences, Inc. Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks
US8889932B2 (en) 2008-11-26 2014-11-18 Elevance Renewable Sciences, Inc. Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions
US8933285B2 (en) 2008-11-26 2015-01-13 Elevance Renewable Sciences, Inc. Methods of producing jet fuel from natural oil feedstocks through metathesis reactions
US8957268B2 (en) 2009-10-12 2015-02-17 Elevance Renewable Sciences, Inc. Methods of refining natural oil feedstocks
US9000246B2 (en) 2009-10-12 2015-04-07 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US9051519B2 (en) 2009-10-12 2015-06-09 Elevance Renewable Sciences, Inc. Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters
US9102877B2 (en) 2008-11-12 2015-08-11 Sartec Corporation Systems and methods for producing fuels from biomass
US9133416B2 (en) 2011-12-22 2015-09-15 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9139493B2 (en) 2011-12-22 2015-09-22 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9169174B2 (en) 2011-12-22 2015-10-27 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9169447B2 (en) 2009-10-12 2015-10-27 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9175231B2 (en) 2009-10-12 2015-11-03 Elevance Renewable Sciences, Inc. Methods of refining natural oils and methods of producing fuel compositions
US9222056B2 (en) 2009-10-12 2015-12-29 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9284515B2 (en) 2007-08-09 2016-03-15 Elevance Renewable Sciences, Inc. Thermal methods for treating a metathesis feedstock
US9365487B2 (en) 2009-10-12 2016-06-14 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US9382502B2 (en) 2009-10-12 2016-07-05 Elevance Renewable Sciences, Inc. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks
US9388098B2 (en) 2012-10-09 2016-07-12 Elevance Renewable Sciences, Inc. Methods of making high-weight esters, acids, and derivatives thereof
US10239812B2 (en) 2017-04-27 2019-03-26 Sartec Corporation Systems and methods for synthesis of phenolics and ketones
US10544381B2 (en) 2018-02-07 2020-01-28 Sartec Corporation Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid
US10696923B2 (en) 2018-02-07 2020-06-30 Sartec Corporation Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids
CN114657027A (zh) * 2022-02-15 2022-06-24 湖北天基生物能源科技发展有限公司 一种地沟油-气相甲醇催化酯化方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020035282A1 (en) * 2000-03-06 2002-03-21 Suppes Galen J. Carbonate catalyzed alcoholysis of triglycerides
US20050274065A1 (en) * 2004-06-15 2005-12-15 Carnegie Mellon University Methods for producing biodiesel
WO2007062825A1 (fr) * 2005-12-01 2007-06-07 Aser S.R.L. Procede de production d'esters a partir d'huiles vegetales ou de graisses animales, utilisant des catalyseurs a base de composes de vanadium

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020035282A1 (en) * 2000-03-06 2002-03-21 Suppes Galen J. Carbonate catalyzed alcoholysis of triglycerides
US20050274065A1 (en) * 2004-06-15 2005-12-15 Carnegie Mellon University Methods for producing biodiesel
WO2007062825A1 (fr) * 2005-12-01 2007-06-07 Aser S.R.L. Procede de production d'esters a partir d'huiles vegetales ou de graisses animales, utilisant des catalyseurs a base de composes de vanadium

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110060153A1 (en) * 2006-08-04 2011-03-10 Mcneff Research Consultants, Inc. Systems and methods for refining alkyl ester compositions
US20110172450A1 (en) * 2006-08-04 2011-07-14 Mcneff Clayton V Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
US8445709B2 (en) * 2006-08-04 2013-05-21 Mcneff Research Consultants, Inc. Systems and methods for refining alkyl ester compositions
US8686171B2 (en) * 2006-08-04 2014-04-01 Mcneff Research Consultants, Inc. Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
US8017796B2 (en) 2007-02-13 2011-09-13 Mcneff Research Consultants, Inc. Systems for selective removal of contaminants from a composition and methods of regenerating the same
US8585976B2 (en) 2007-02-13 2013-11-19 Mcneff Research Consultants, Inc. Devices for selective removal of contaminants from a composition
US9284515B2 (en) 2007-08-09 2016-03-15 Elevance Renewable Sciences, Inc. Thermal methods for treating a metathesis feedstock
US9216941B2 (en) 2007-08-09 2015-12-22 Elevance Renewable Sciences, Inc. Chemical methods for treating a metathesis feedstock
US8642824B2 (en) 2007-08-09 2014-02-04 Elevance Renewable Sciences, Inc. Chemical methods for treating a metathesis feedstock
US8692006B2 (en) 2007-08-09 2014-04-08 Elevance Renewable Sciences, Inc. Thermal methods for treating a metathesis feedstock
US8466305B2 (en) 2007-09-28 2013-06-18 Mcneff Research Consultants, Inc. Methods and compositions for refining lipid feed stocks
US8361174B2 (en) 2008-10-07 2013-01-29 Sartec Corporation Catalysts, systems, and methods for producing fuels and fuel additives from polyols
US9102877B2 (en) 2008-11-12 2015-08-11 Sartec Corporation Systems and methods for producing fuels from biomass
US8889932B2 (en) 2008-11-26 2014-11-18 Elevance Renewable Sciences, Inc. Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions
US8933285B2 (en) 2008-11-26 2015-01-13 Elevance Renewable Sciences, Inc. Methods of producing jet fuel from natural oil feedstocks through metathesis reactions
WO2010144597A1 (fr) * 2009-06-09 2010-12-16 Mcneff Research Consultants, Inc. Systèmes et procédés pour raffiner des compositions d'ester alkylique
US9365487B2 (en) 2009-10-12 2016-06-14 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US8735640B2 (en) 2009-10-12 2014-05-27 Elevance Renewable Sciences, Inc. Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks
US10689582B2 (en) 2009-10-12 2020-06-23 Elevance Renewable Sciences, Inc. Methods of refining natural oil feedstocks
US9732282B2 (en) 2009-10-12 2017-08-15 Elevance Renewable Sciences, Inc. Methods of refining natural oil feedstocks
US9469827B2 (en) 2009-10-12 2016-10-18 Elevance Renewable Sciences, Inc. Methods of refining natural oil feedstocks
US9169447B2 (en) 2009-10-12 2015-10-27 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9175231B2 (en) 2009-10-12 2015-11-03 Elevance Renewable Sciences, Inc. Methods of refining natural oils and methods of producing fuel compositions
US9000246B2 (en) 2009-10-12 2015-04-07 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US9222056B2 (en) 2009-10-12 2015-12-29 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US8957268B2 (en) 2009-10-12 2015-02-17 Elevance Renewable Sciences, Inc. Methods of refining natural oil feedstocks
US9284512B2 (en) 2009-10-12 2016-03-15 Elevance Renewable Sicences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US9051519B2 (en) 2009-10-12 2015-06-09 Elevance Renewable Sciences, Inc. Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters
US9382502B2 (en) 2009-10-12 2016-07-05 Elevance Renewable Sciences, Inc. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks
US9464258B2 (en) 2009-10-12 2016-10-11 Elevance Renewable Sciences, Inc. Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters
US9169174B2 (en) 2011-12-22 2015-10-27 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9481627B2 (en) 2011-12-22 2016-11-01 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9139493B2 (en) 2011-12-22 2015-09-22 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9133416B2 (en) 2011-12-22 2015-09-15 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9388098B2 (en) 2012-10-09 2016-07-12 Elevance Renewable Sciences, Inc. Methods of making high-weight esters, acids, and derivatives thereof
US10239812B2 (en) 2017-04-27 2019-03-26 Sartec Corporation Systems and methods for synthesis of phenolics and ketones
US10544381B2 (en) 2018-02-07 2020-01-28 Sartec Corporation Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid
US10696923B2 (en) 2018-02-07 2020-06-30 Sartec Corporation Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids
CN114657027A (zh) * 2022-02-15 2022-06-24 湖北天基生物能源科技发展有限公司 一种地沟油-气相甲醇催化酯化方法

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