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WO2025205990A1 - Procédé de production de carburant d'aviation durable et carburant biodiesel - Google Patents

Procédé de production de carburant d'aviation durable et carburant biodiesel

Info

Publication number
WO2025205990A1
WO2025205990A1 PCT/JP2025/012105 JP2025012105W WO2025205990A1 WO 2025205990 A1 WO2025205990 A1 WO 2025205990A1 JP 2025012105 W JP2025012105 W JP 2025012105W WO 2025205990 A1 WO2025205990 A1 WO 2025205990A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
acid alkyl
mixture
alkyl ester
coconut oil
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.)
Pending
Application number
PCT/JP2025/012105
Other languages
English (en)
Japanese (ja)
Inventor
泰昭 前田
規訓 竹中
健二 興津
フィン プオン ウイエン グエン
秦一郎 小川
浩一 森
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mannryu Ltd
Naolab
Naolab Ltd
Original Assignee
Mannryu Ltd
Naolab
Naolab Ltd
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 Mannryu Ltd, Naolab, Naolab Ltd filed Critical Mannryu Ltd
Publication of WO2025205990A1 publication Critical patent/WO2025205990A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • 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

  • a method for producing sustainable aviation fuel comprising: using coconut oil as a raw material, producing a mixture of fatty acid alkyl esters by reacting fatty acid triglycerides and/or fatty acids that are degradation products thereof with a lower alcohol; and vacuum distilling the mixture of fatty acid alkyl esters to separate a C8 fatty acid alkyl ester fraction and/or a C10 fatty acid alkyl ester fraction.
  • the production method according to [1] further comprising distilling the mixture obtained after separating the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction under reduced pressure to separate the C12 fatty acid alkyl ester fraction.
  • a mixture of fatty acid alkyl esters is produced by reacting fatty acid triglycerides and/or fatty acids that are decomposition products thereof with a lower alcohol;
  • a method for producing a biodiesel fuel comprising: distilling a mixture of fatty acid alkyl esters under reduced pressure to remove a C8 fatty acid alkyl ester fraction and/or a C10 fatty acid alkyl ester fraction; and obtaining a mixture obtained after removing the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction.
  • Coconut oil may be virgin coconut oil or used, waste coconut oil. Examples of the fatty acid composition of virgin coconut oil and waste coconut oil are shown in Table 2.
  • Method for manufacturing SAF In a first aspect, a method for producing an SAF is provided.
  • the method of the present embodiment includes producing a mixture of fatty acid alkyl esters using coconut oil as a feedstock.
  • the fatty acid composition in the mixture of fatty acid alkyl esters has a composition derived from the coconut oil used as a raw material.
  • the mixture of fatty acid alkyl esters can be produced, for example, by the following method.
  • coconut oil is used as a raw material.
  • coconut oil itself may be used as a raw material, or fatty acid triglycerides extracted from coconut oil may be used as a raw material.
  • fatty acid triglycerides derived from fatty acid alkyl esters are the starting material in the production reaction.
  • the production reaction include a transesterification reaction using a fatty acid triglyceride derived from coconut oil and a lower alkyl alcohol, or an ester formation reaction using a fatty acid obtained by hydrolyzing a fatty acid triglyceride derived from coconut oil and a lower alkyl alcohol.
  • the mixing may be carried out to the extent that the reaction system becomes a homogeneous phase system, which means that the fatty acid triglyceride or fatty acid, catalyst, organic solvent, and lower alkyl alcohol form a single phase.
  • the catalyst may be a catalyst commonly used in transesterification reactions. Examples include alkali catalysts such as sodium hydroxide and potassium hydroxide, acid catalysts such as hydrochloric acid, sulfuric acid, and hydrofluoric acid, enzymes such as lipase, inorganic substances such as calcium oxide, and solid catalysts such as ion exchange resins such as cation exchange resins and anion exchange resins. Preferably, an alkali catalyst or an acid catalyst is used. Furthermore, a single catalyst may be used, or multiple catalysts may be used in combination.
  • the alkali catalyst or acid catalyst may be used in the form of an aqueous solution or the like according to a known method.
  • the transesterification reaction involves mixing fatty acid triglycerides derived from coconut oil or fatty acids produced by decomposing fatty acid triglycerides derived from coconut oil, a catalyst, an organic solvent, and a lower alkyl alcohol.
  • Mixing may be carried out in a container equipped with a stirring means.
  • the fatty acid triglyceride or fatty acid, catalyst, organic solvent, and lower alkyl alcohol are placed in the container and mixed.
  • the stirring may be done manually or by using a device, and any known stirring means may be used.
  • the method of this embodiment further includes recovering acetone, alcohol, and glycerin.
  • the recovery of acetone and alcohol may be carried out by distilling or vacuum distilling the reaction solution containing the fatty acid alkyl ester obtained by the above reaction.
  • the distillation or vacuum distillation may be carried out according to a known method.
  • the distillation or vacuum distillation may be carried out at a temperature of 100°C or less, preferably 60°C to 80°C, and more preferably 65°C to 75°C.
  • the distillation or vacuum distillation may also be carried out at a pressure of 1 atmosphere or less, preferably 0.9 atmospheres or less, and more preferably 0.8 atmospheres or less.
  • the reaction time is adjusted appropriately depending on the reaction, so is not particularly limited, but is set to a reaction time of 1 minute to 3 hours, preferably 5 minutes to 2 hours, and more preferably 10 minutes to 1 hour.
  • Glycerin may be recovered by allowing the reaction solution to stand and separate into a fatty acid alkyl ester layer (upper layer) and a glycerin layer (lower layer), and then recovering the lower glycerin layer.
  • the method of this embodiment may include washing the reaction solution after glycerin recovery. This washing may be carried out by adding water to the reaction solution after glycerin recovery, leaving it to stand to separate into an alkyl ester layer and a water layer, and then recovering the water in the lower layer. This washing may be carried out multiple times until the pH of the washed water becomes neutral.
  • distillation or reduced pressure distillation may be carried out at a pressure of 1 atmosphere or less, preferably 0.9 atmospheres or less, more preferably 0.8 atmospheres or less.
  • the reaction time is adjusted appropriately depending on the reaction and is not particularly limited, but is set to 1 minute to 3 hours, preferably 5 minutes to 2 hours, and more preferably 10 minutes to 1 hour.
  • the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction are separated, they may be separated under conditions for separating both fractions simultaneously, or separately, or a portion may be separated simultaneously and the remainder separately.
  • fractions containing C8 fatty acid alkyl esters and/or C10 fatty acid alkyl esters may be mixed.
  • the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction obtained by the above-mentioned vacuum distillation may be heated under reduced pressure to remove moisture.
  • moisture may be removed at a pressure of 1 atmosphere or less, preferably 0.9 atmospheres or less, more preferably 0.8 atmospheres or less, and at a temperature of 100°C or less, preferably 90°C or less, more preferably 80°C or less.
  • the C8 fatty acid alkyl ester and/or the C10 fatty acid alkyl ester obtained in this manner can be used as SAF.
  • distillation or vacuum distillation may be carried out at a pressure of 1 atmosphere or lower, preferably 0.9 atmospheres or lower, more preferably 0.8 atmospheres or lower.
  • the reaction time is adjusted appropriately depending on the reaction and is not particularly limited, but is set to 1 minute to 3 hours, preferably 5 minutes to 2 hours, and more preferably 10 minutes to 1 hour.
  • the C12 fatty acid alkyl ester fraction separated by the above-mentioned vacuum distillation may be subjected to a known hydrodecarboxylation reaction to produce C12 isoparaffins.
  • the C12 fatty acid alkyl esters may be subjected to a sulfide treatment using a known method, and after the sulfide treatment, hydrogen may be added and the reaction may be carried out at 200°C to 300°C, preferably 230°C to 270°C, and more preferably 240°C to 260°C, for 30 minutes to 4 hours, preferably 1 hour to 3 hours.
  • the C12 isoparaffins obtained in this manner can be used as SAF.
  • the method of the present embodiment includes producing isopropyl esters by an esterification reaction, which may be carried out by reacting a C8 fatty acid and/or a C10 fatty acid with a catalyst, an organic solvent, and isopropanol.
  • the catalyst used in the ester production reaction may be an acid catalyst, preferably sulfuric acid.
  • the amount of catalyst used in the ester production reaction may be adjusted appropriately depending on the amount of fatty acid in the raw material, the scale of the reaction system, etc. Specifically, an amount may be determined appropriately so that the rate of the ester production reaction does not decrease, the reaction can proceed sufficiently, and the catalyst can be separated during purification.
  • the ester production reaction involves heating a solution containing a mixture of C8 fatty acids and/or C10 fatty acids, a catalyst, an organic solvent, and isopropanol.
  • the heating is carried out at a temperature of 30°C to 90°C, preferably 40°C to 80°C, more preferably 50°C to 70°C, and even more preferably 55°C to 65°C.
  • the reaction time is adjusted appropriately depending on the reaction, so is not particularly limited, but is typically set to 1 to 12 hours, preferably 2 to 8 hours, and more preferably 4 to 6 hours.
  • reaction solution may be allowed to stand to separate into a fatty acid alkyl ester layer (upper layer) and a water layer (lower layer), and the lower water layer may then be collected to recover water containing the catalyst.
  • the method of this embodiment may also include washing the reaction solution after catalyst recovery. This washing may be carried out by adding water to the reaction solution after catalyst recovery, leaving it to stand to separate into an alkyl ester layer and a water layer, and then recovering the water from the lower layer. This washing may be repeated multiple times until the pH of the washed water becomes neutral.
  • the method of this embodiment may also include drying the reaction solution after washing.
  • This drying may be carried out according to a known method. For example, drying may be carried out at a temperature of 100°C or less, preferably 60°C to 90°C, and more preferably 75°C to 85°C. Drying may also be carried out at a pressure of 1 atmosphere or less, preferably 0.9 atmospheres or less, and more preferably 0.8 atmospheres or less.
  • the C8 fatty acid isopropyl ester and/or C10 fatty acid isopropyl ester obtained in this manner can be used as an SAF.
  • Method for producing BDF In a second aspect, a method for producing BDF is provided.
  • the method of this embodiment includes producing a mixture of fatty acid alkyl esters, recovering acetone, alcohol, and glycerin, and distilling off the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction, but these may be similar to the producing a mixture of fatty acid alkyl esters, recovering acetone, alcohol, and glycerin, and separating off the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction described in the above-mentioned method for producing SAF, and therefore further explanation will be omitted.
  • the method of this embodiment may also include obtaining the reaction solution after the C8 fatty acid alkyl ester fraction and/or the C10 fatty acid alkyl ester fraction has been distilled off as BDF.
  • the method of this embodiment may further include distilling off the C12 fatty acid alkyl ester fraction, and this distillation may be similar to the separation of the C12 fatty acid alkyl ester fraction described in the above-mentioned method for producing SAF.
  • the method of this embodiment may also include obtaining the reaction solution after distilling off the C12 fatty acid alkyl ester fraction as BDF.
  • C6, C8, and C10 methyl esters, C6, C8, C10, and C12 ethyl esters, C6, C8, C10, and C12 propyl esters, C6, C8, C10, and C12 isopropyl esters, and C6, C8, and C10 butyl esters may be used as SAFs.
  • C12, C14, C16, and C18 methyl esters, C14, C16, and C18 ethyl esters, C14, C16, and C18 propyl esters, C14, C16, and C18 isopropyl esters, and C12, C14, C16, and C18 butyl esters may be used as BDFs.
  • the SAF produced by the above-mentioned method may be added to kerosene in an amount of 10% or more, preferably 30% or more, and more preferably 50% or more.
  • the SAF is C8, C10, and C12 fatty acid ethyl esters, fatty acid propyl esters, and isopropyl esters
  • the SAF may be added to kerosene in an amount of 30% or more.
  • the SAF is C8 and C10 fatty acid methyl esters
  • the SAF may be added to kerosene in an amount of 10% or more.
  • the SAF is C8 and C10 fatty acid ethyl esters and fatty acid propyl esters
  • the SAF may be added to kerosene in an amount of up to 50%.
  • L/LSAF refers to a numerical unit that converts the amount of energy consumed for heating a solution, etc., when producing 1 L of SAF into the amount of petroleum.
  • the numerical value expressed in this unit serves as an evaluation index of the energy consumption during SAF production.
  • the energy consumption during production, converted into petroleum equivalent is preferably 1 L/LSAF or less, more preferably 0.7 L/LSAF or less, more preferably 0.5 L/LSAF or less, and even more preferably 0.2 L/LSAF.
  • Example 2 The same steps as in the processes (1-1) to (1-3) of Example 1 were carried out, except that the dried C12 to C18 fatty acid alkyl component remaining in the reactor was not recovered.
  • Example 3 The same steps as in (1-1) to (1-3) of Example 1 were carried out to obtain C8 and C10 alkyl esters.
  • Figures 2 to 9 show that the yields of SAF and BDF in the examples were all within the range of 97% to 99%.
  • the yield of BDF in this example exceeded the 96.5% fatty acid ester content standard specified in JIS K2390.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production d'un carburant d'aviation durable et d'un carburant biodiesel.
PCT/JP2025/012105 2024-03-26 2025-03-26 Procédé de production de carburant d'aviation durable et carburant biodiesel Pending WO2025205990A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2024050422 2024-03-26
JP2024-050422 2024-03-26

Publications (1)

Publication Number Publication Date
WO2025205990A1 true WO2025205990A1 (fr) 2025-10-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2025/012105 Pending WO2025205990A1 (fr) 2024-03-26 2025-03-26 Procédé de production de carburant d'aviation durable et carburant biodiesel

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Country Link
WO (1) WO2025205990A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008081559A (ja) * 2006-09-26 2008-04-10 Nippon Shokubai Co Ltd バイオディーゼル燃料組成物およびその製造方法
JP2011508047A (ja) * 2007-12-27 2011-03-10 サイバス，エルエルシー アルキルエステル脂肪酸配合物およびその用途
JP2021523255A (ja) * 2018-05-03 2021-09-02 リニューアブル エナジー グループ インコーポレイテッド バイオディーゼル、ディーゼルレンジ炭化水素を製造するための方法及び装置並びに生成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008081559A (ja) * 2006-09-26 2008-04-10 Nippon Shokubai Co Ltd バイオディーゼル燃料組成物およびその製造方法
JP2011508047A (ja) * 2007-12-27 2011-03-10 サイバス，エルエルシー アルキルエステル脂肪酸配合物およびその用途
JP2021523255A (ja) * 2018-05-03 2021-09-02 リニューアブル エナジー グループ インコーポレイテッド バイオディーゼル、ディーゼルレンジ炭化水素を製造するための方法及び装置並びに生成物

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