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WO2007060993A1 - Procede pour produire un ester d'alkyle d'acide gras - Google Patents

Procede pour produire un ester d'alkyle d'acide gras Download PDF

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Publication number
WO2007060993A1
WO2007060993A1 PCT/JP2006/323325 JP2006323325W WO2007060993A1 WO 2007060993 A1 WO2007060993 A1 WO 2007060993A1 JP 2006323325 W JP2006323325 W JP 2006323325W WO 2007060993 A1 WO2007060993 A1 WO 2007060993A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
oil
alkali
fat
reaction
Prior art date
Application number
PCT/JP2006/323325
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English (en)
Japanese (ja)
Inventor
Keiichi Tsuto
Yuuichiro Azuma
Tetsuya Koshikawa
Original Assignee
Revo International 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 Revo International Inc. filed Critical Revo International Inc.
Publication of WO2007060993A1 publication Critical patent/WO2007060993A1/fr

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Classifications

    • 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
    • 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
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • 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 alkyl ester. More specifically, fatty acid alkyl esters are produced by a transesterification reaction with alcohol using oils and fats derived from plants, or waste edible oils discarded from restaurants, food factories, general households, etc. as a suitable raw material fats and oils. Regarding the method. Background art
  • Fatty acid alkyl esters are important as raw materials for oil and fat products, for example, various surfactants, in the oil and fat chemical industry. Therefore, the manufacturing process is one of the most important processes in the oil and chemical industry as a J11 process.
  • fatty acid alkyl esters are attracting attention as a new energy alternative to petroleum because they can be used as diesel fuel derived from biomass.
  • Cooking oil (waste cooking oil) that is used and discarded in restaurants, food factories, general households, etc. is treated with a coagulant and buried in the soil, or discarded as household waste and incinerated.
  • a coagulant and buried in the soil, or discarded as household waste and incinerated.
  • the idea of cleansing the global environment has increased, the movement of effective reuse of these edible oils has become active. .
  • an attempt to produce an oil suitable for diesel fuel by obtaining fatty acid methyl ester by transesterification with methanol has begun for a while.
  • fatty acid methyl esters obtained from vegetable oils used for edible oils are similar to light oil in physical properties such as viscosity and specific gravity, and combustibility, and can be used without engine modification. Although it has been pointed out for a long time, it has recently been highlighted as a recyclable biofuel and is widely used especially in the United States and Europe. However, fatty acid methyl esters derived from edible oils are mainly used in mixed systems with light oil because of the higher cost compared to light oil.
  • fats and oils used as raw materials for edible oils contain about 3% by weight or less of free fatty acids, and the free fatty acids neutralize the alkali catalyst used in the transesterification reaction.
  • the amount of alkali catalyst required for the transesterification reaction increases, and subsequent catalyst removal costs high. Therefore, expensive fats and oils from which free fatty acids have been removed are required for the transesterification reaction.
  • the content of free fatty acid in the cooking oil before use is 0.1% by weight or less, but the cooking oil after use is usually deteriorated to 0.5%. Since it contains about 1% by weight of free fatty acids, it is necessary to remove the free fatty acids. Therefore, in order to use inexpensive fats and oils, it is necessary to solve this problem of free fatty acids.
  • Non-Patent Document 1 Edited by Akio Kato, “Use of palm oil and palm kernel oil”, Sachibo, 1990, P. 35
  • Non-Patent Document 2 “Biomass Handbook”, Japan Institute of Energy, 2002, P. 138
  • An object of the present invention is to provide an efficient method for producing a fatty acid alkyl ester, which can be carried out at a low operating cost, using an inexpensive raw material fat and oil in view of the above-described conventional technology. .
  • the present invention is a method for producing a fatty acid alkyl ester by carrying out a transesterification reaction of fats and oils in the presence of an alkali catalyst, wherein the alkali-containing glycerin by-produced by the transesterification reaction is produced. It is mixed with raw material fats and oils and fats obtained in a pretreatment step including a step of neutralizing free fatty acids in the raw material fats and oils with an alkali catalyst in an alkali-containing glycerin, and subjected to the transesterification, The present invention relates to a method for producing a fatty acid alkyl ester.
  • a fatty acid alkyl ester can be efficiently produced at a low operating cost by using an inexpensive raw material fat.
  • the present invention provides a method for producing a fatty acid alkyl ester by performing a transesterification reaction between an oil and a fat and an alcohol in the presence of an alkali catalyst, and treating the raw oil and fat with an alkali-containing glycerin by-produced in the transesterification reaction. Obtained in the pretreatment step It has a great feature in that fats and oils are subjected to a transesterification reaction.
  • the pretreatment step includes a step of mixing the alkali-containing glycerin by-produced in the ester exchange reaction with the raw material fat and oil, and neutralizing the free fatty acid in the raw material fat with an alkali catalyst in the alkali-containing glycerin.
  • a fatty acid alkyl ester can be efficiently produced by using the alkali-containing glycerin by-produced in the transesterification reaction by this pretreatment step.
  • the step of neutralizing the free fatty acid in the raw oil and fat is, for example, mixing alkali-containing glycerin and the raw oil and fat, and optionally heating appropriately to proceed with the neutralization reaction. Can be implemented.
  • the amount of alkali-containing glycerin used is such that the amount of the alkali catalyst contained is commensurate with the amount required for neutralization of the free fatty acid. It is preferable to adjust.
  • the content of the alkali catalyst in the alkali-containing glycerin used in the pretreatment step is not particularly limited, but is preferably about 2 to 10% by weight from the viewpoint of operability.
  • the usage form of alkali-containing glycerin produced as a by-product in the transesterification reaction should be selected as appropriate in consideration of the production scale and other factors, whether batch or continuous, in combination with the transesterification reaction. Can do.
  • the fats and oils can be separated by separating them into a fat layer and a glycerin layer containing an alkali metal salt of a fatty acid by a method such as stationary separation.
  • a method such as stationary separation.
  • an intermediate layer is hardly generated even in the case of stationary separation, so that the fat and oil layer can be separated with a high yield. Therefore, it is a method having excellent viewpoint power for removing gums only by free fatty acid treatment, and the pretreatment step in the present invention can be said to be a high yield defree fatty acid step and degumming step.
  • the fat and oil obtained in the pretreatment step has a reduced amount of free fatty acid, deactivation due to neutralization of the alkali catalyst used in the ester exchange reaction can be suppressed.
  • the fats and oils subjected to the ester exchange reaction are preferably reduced to 0.06 wt% or less, more preferably 0.03 wt% or less, by a method such as dehydration under reduced pressure.
  • glycerin containing an alkali metal salt of a fatty acid can be widely reused as a chemical product by removing the alkali metal salt and purifying it, or as a fuel as a heat source.
  • raw oils and fats used in the pretreatment process include rapeseed oil, sesame oil, soybean oil, corn oil, sunflower oil, palm oil, palm kernel oil, palm oil, safflower oil, and papaya seed oil. And one or a mixture of two or more selected from the group consisting of vegetable oils.
  • palm oil when fatty acid alkyl esters are produced in large quantities, palm oil is preferred because of its high productivity (cultivation efficiency) and easy availability.
  • papaya seed oil is preferable for the viewpoint of the amount of free fatty acid.
  • Papaya seed oil has a free fatty acid content of about 0.9 to 1.1% by weight, which is relatively toxic to vegetable oils. In addition to its low load, it is toxic to animals and humans.
  • the raw oil and fat used in the present invention is not limited to unused clean oil, and waste edible oil is preferable from the viewpoint of economic and social demands that may be waste edible oil.
  • the waste edible oil in the present invention refers to edible oil that is used and discarded in restaurants, food factories, general households, etc., and is a rational raw material. Free fatty acids contained in waste edible oil increase due to deterioration compared to unused edible oil, but 0.5 to 1 weight compared to fat and oil used as a raw material for edible oil before removal of free fatty acid Like papaya seed oil, which is a small percentage, it is also suitably used as a raw material fat in the present invention from the viewpoint of the amount of free fatty acid.
  • waste edible oil and Z or papaya seed oil can be suitably used as the raw oil and fat from the viewpoint that the amount of free fatty acid can be rationally utilized.
  • the alcohol used in the present invention is selected from the group consisting of alkyl alcohol having 1 to 10 carbon atoms such as methyl alcohol (methanol), ethyl alcohol (ethanol), isobutyl alcohol, etc. 1 Species or a mixture of two or more.
  • the purity of the alcohol is not particularly limited, but a lower water content is preferred.
  • methyl alcohol and ethyl alcohol are preferred in consideration of the use of fatty acid alkyl esters as diesel fuel oil. That's right.
  • the transesterification reaction is an equilibrium reaction, it is preferable to use as much alcohol as possible.
  • 100 parts by weight of fats and oils used for the transesterification reaction On the other hand, 12 to 50 parts by weight is preferred, and 15 to 35 parts by weight is more preferred.
  • Examples of the alkali catalyst that promotes the transesterification reaction between fat and alcohol include sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, sodium alcoholate, and potassium alcoholate.
  • the alkali catalysts at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium alcoholate and potassium alcoholate is preferred, which is preferably highly alkaline hydroxide sodium and Z or hydroxide. Potassium halide is more preferred.
  • fats and oils whose free fatty acid amount has been reduced by the pretreatment step are used, so that the amount of alkali catalyst consumed for neutralization of free fatty acids contained in the fats and oils is extremely small, and the ester exchange reaction itself. Is promoted by an Al force catalyst having a catalyst amount of 0.2 to 0.5 parts by weight per 100 parts by weight of fats and oils.
  • the by-produced alkali-containing glycerin is continuously used in the pretreatment step and mixed with the raw material fats and oils to neutralize the free fatty acids contained in the raw material fats and oils.
  • an alkali catalyst in an amount capable of neutralizing the free fatty acid contained in the raw material oil to be mixed for the transesterification reaction. For this reason, an alkali catalyst in an amount more than that required for the transesterification reaction may be used. In the present invention, however, the alkali catalyst is not only used as a catalyst. Can be used twice as an agent. As a result, it is possible to reduce the amount of alkaline compound required to use the raw fat and oil containing free fatty acids, and to remove the used alkali catalyst after the transesterification reaction. Powerful load will be reduced.
  • the amount of alkali catalyst used varies depending on the type of alkali catalyst and the type of raw material oil and fat, and cannot be determined unconditionally.
  • sodium hydroxide or potassium hydroxide as an alkali catalyst, In the method for continuously producing a fatty acid alkyl ester while subjecting the alkali-containing glycerin to a pretreatment step as needed, 0.5 to 3.0 weight of free fatty acid is obtained.
  • sodium hydroxide or potassium hydroxide is preferably used in an amount of 0.2 to 1.5 parts by weight with respect to 100 parts by weight of fats and oils used in the transesterification reaction. 2 to 1.0 part by weight is more preferable.
  • the amount of sodium hydroxide or potassium hydroxide used is the transesterification reaction. 0.2 to 0.6 parts by weight is preferable with respect to 100 parts by weight of the fats and oils to be supplied to the oil.
  • the amount of sodium hydroxide or potassium hydroxide used is 100 parts by weight of fats and oils used in the transesterification reaction. 0.5 to 1.5 parts by weight are preferred 0.5 to 1.0 parts by weight are more preferred.
  • the reaction temperature is 50 to 90 ° C. preferable.
  • a mixture containing the desired fatty acid alkyl ester, by-produced glycerin, an alkali catalyst, and the like is obtained by the transesterification of the above fat and alcohol.
  • the progress of the reaction can be confirmed by, for example, collecting the sample solution and allowing it to stand, and then analyzing the ester content of the upper ester layer by gas chromatography.
  • the residual alcohol is evaporated and removed as necessary, and the reaction mixture is phase-separated by using the difference in specific gravity by standing or centrifuging, so that the oil layer has a strong fatty acid alkyl ester strength.
  • the alkali-containing glycerin layer can be easily separated.
  • this alkali-containing glycerin is used in the pretreatment step in which it is mixed with newly used raw material fats and oils.
  • the content of fatty acid methyl ester is at least 96% as a nanofuel. Therefore, when the content of the fatty acid methyl ester obtained by the transesterification reaction is less than 96%, an alcohol and an alkali catalyst are mixed with the oil layer made of the fatty acid alkyl ester carbonate obtained by the transesterification reaction. It is preferable to increase the content of fatty acid methyl ester to such an extent that it can be suitably used as diesel fuel by subjecting it to an ester exchange reaction again. [0031] Furthermore, when the fatty acid alkyl ester contains a trace amount of an alkali component or the like, it can be removed by a purification operation such as washing with water.
  • the fatty acid alkyl ester can be produced economically and efficiently, so that the fatty acid alkyl ester as a biofuel expected as an alternative to light oil can be further spread.
  • alkali-containing glycerin obtained in the first stage reaction of Reference Example 1 was pretreated as follows. Used in the process. In Reference Example 1, unused edible oil was used, the amount of free fatty acid was as small as 0.07% by weight, and when the amount of free fatty acid was less than 0.2% by weight, free fatty acid was used. The amount of alkali catalyst consumed for neutralization is negligible. Therefore, the alkali-containing glycerin obtained in the first stage reaction of Reference Example 1 contains almost 0.3 part (0.9 g) of the alkali catalyst (sodium hydroxide) used in the transesterification reaction. Remained.
  • a fatty acid methyl ester was obtained in the same manner as in Example 1, except that the pretreatment step was performed using the alkali-containing glycerin obtained in the first-stage reaction of Example 1.
  • the alkali-containing product obtained in the first stage reaction of Example 1 was used.
  • Most of 0.3 part by weight (0.9 g) of the alkali catalyst (sodium hydroxide) used in the transesterification reaction remained in dalyserin.
  • the fatty acid alkyl ester obtained by the present invention can be suitably used as a biomass-derived diesel fuel that is attracting attention as a new energy alternative to petroleum.

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

Abstract

La présente invention concerne un procédé pour produire un ester d'alkyle d'acide gras par transestérification d'une graisse-huile avec un alcool en présence d’un catalyseur alcalin. Le procédé est caractérisé en ce qu'une telle graisse-huile est soumise à la transestérification qui est obtenue dans une étape de prétraitement comprenant l’étape consistant à mélanger une glycérine contenant un alcali produite dans la transestérification en tant que produit secondaire avec une graisse-huile brute pour neutraliser un acide gras libre contenu dans la graisse-huile brute avec un catalyseur alcalin contenu dans la glycérine contenant un alcali. L'ester d'alkyle d'acide gras peut être utilisé de manière appropriée en tant que carburant diesel dérivé de biomasse ou similaire qui est aujourd'hui l'objet d'attention en tant que nouvelle énergie pour remplacer le pétrole.
PCT/JP2006/323325 2005-11-28 2006-11-22 Procede pour produire un ester d'alkyle d'acide gras WO2007060993A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-342668 2005-11-28
JP2005342668A JP2007145759A (ja) 2005-11-28 2005-11-28 脂肪酸アルキルエステルの製造方法

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020175661A1 (fr) * 2019-02-27 2020-09-03 バイオ燃料技研工業株式会社 Procédé de traitement de l'eau, et procédé et système de production d'agent de dénitrification ou d'agent favorisant la nitrification
CN111690468A (zh) * 2020-06-24 2020-09-22 海南绿新新能源有限公司 一种新型生物油脂调和清洁燃料油生产方法
CN114196482A (zh) * 2021-12-23 2022-03-18 湖北新铭生物能源科技有限公司 一种餐厨废弃油脂制生物柴油的方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5124764B2 (ja) * 2006-07-21 2013-01-23 国立大学法人 鹿児島大学 バイオディーゼル燃料の製造方法
BRPI1004589A2 (pt) * 2010-11-10 2013-02-26 Arak Idea Servicos De Design E Patentes Ltda estrutura articulÁvel em forma de fractal
JP6457839B2 (ja) * 2015-02-27 2019-01-23 関西化学機械製作株式会社 改質油脂の製造方法およびそれを用いた脂肪酸エステルの製造方法
EP4071226A1 (fr) * 2021-04-08 2022-10-12 AT Agrar-Technik Int. GmbH Processus pour produire des esters d'alkyle d'acides gras

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5434279A (en) * 1991-11-06 1995-07-18 Wimmer; Theodor Process for preparing fatty acid esters of short-chain monohydric alcohols
JPH10182518A (ja) * 1996-12-27 1998-07-07 Someya Shoten:Kk 廃食用油等から高級脂肪酸のメチルエステルとグリセリンとを連続的に製造する方法および装置
US6538146B2 (en) * 1999-06-07 2003-03-25 At Agrar-Technik Gmbh Method for producing fatty acid esters of monovalent alkyl alcohols and use thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5434279A (en) * 1991-11-06 1995-07-18 Wimmer; Theodor Process for preparing fatty acid esters of short-chain monohydric alcohols
JPH10182518A (ja) * 1996-12-27 1998-07-07 Someya Shoten:Kk 廃食用油等から高級脂肪酸のメチルエステルとグリセリンとを連続的に製造する方法および装置
US6538146B2 (en) * 1999-06-07 2003-03-25 At Agrar-Technik Gmbh Method for producing fatty acid esters of monovalent alkyl alcohols and use thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020175661A1 (fr) * 2019-02-27 2020-09-03 バイオ燃料技研工業株式会社 Procédé de traitement de l'eau, et procédé et système de production d'agent de dénitrification ou d'agent favorisant la nitrification
JPWO2020175661A1 (ja) * 2019-02-27 2021-12-23 バイオ燃料技研工業株式会社 水処理方法、脱窒剤または硝化促進剤の製造方法および製造システム
JP7527657B2 (ja) 2019-02-27 2024-08-05 バイオ燃料技研工業株式会社 水処理方法、脱窒剤または硝化促進剤の製造方法および製造システム
CN111690468A (zh) * 2020-06-24 2020-09-22 海南绿新新能源有限公司 一种新型生物油脂调和清洁燃料油生产方法
CN114196482A (zh) * 2021-12-23 2022-03-18 湖北新铭生物能源科技有限公司 一种餐厨废弃油脂制生物柴油的方法

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