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WO2018191653A1 - Procédés et compositions pour la production de biodiesel - Google Patents

Procédés et compositions pour la production de biodiesel Download PDF

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Publication number
WO2018191653A1
WO2018191653A1 PCT/US2018/027548 US2018027548W WO2018191653A1 WO 2018191653 A1 WO2018191653 A1 WO 2018191653A1 US 2018027548 W US2018027548 W US 2018027548W WO 2018191653 A1 WO2018191653 A1 WO 2018191653A1
Authority
WO
WIPO (PCT)
Prior art keywords
biodiesel
methanol
feedstock
feedstock mixture
mixture
Prior art date
Application number
PCT/US2018/027548
Other languages
English (en)
Inventor
Sanjeev Gupta
Gangadhar M. RAO
Original Assignee
Aemetis, 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 Aemetis, Inc. filed Critical Aemetis, Inc.
Publication of WO2018191653A1 publication Critical patent/WO2018191653A1/fr

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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, 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/649—Biodiesel, i.e. fatty acid alkyl esters
    • 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
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • 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
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/26—Composting, fermenting or anaerobic digestion fuel components or materials from which fuels are prepared
    • 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
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/54—Specific separation steps for separating fractions, components or impurities during preparation or upgrading of a fuel
    • 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 disclosure provides a method of producing a biodiesel having an ester content of at least 95% comprising the steps of: a) adding a feedstock mixture comprising feedstock and 0.3% enzyme into a reactor, wherein the feedstock comprises at least 50% free fatty acids (FFA) and at least 30% triglyceride; b) adding between 5 and 15% methanol to the reactor within 4 hours of adding the feedstock mixture into the reactor, wherein the feedstock mixture, enzyme, and methanol are under constant agitation; c) adding an additional 13 to 16% methanol to the reactor at the rate of 1% per hour, for between 9 and 11 hours; d) testing the feedstock mixture for ester, FFA and triglycerides; e) adding between 9 and 11% NaOH solution to the reactor when the FFA concentration of the feedstock mixture is between 2 and 4% w/v; f) transferring the feedstock mixture to an intermediate tank when the FFA concentration of the feedstock mixture is between 0.2 and 2.
  • FFA free fatty
  • the method further comprises mixing the crude biodiesel and no greater than 10% ethanol with the feedstock before step a).
  • about 11% methanol is added in step b).
  • about 15% methanol is added for at least 10 hours in step c).
  • about 10% NaOH mixture is added when the FFA is about 3% w/v in step e).
  • the feedstock mixture is transferred when the FFA is about 0.3% in step f).
  • the temperature of the bioreactor is 65°C and the vacuum is 700 Torr in step g).
  • the enzyme catalyzes at least one of transesterification and esterification reactions. In a preferred embodiment, the enzyme catalyzes transesterification and esterification reactions.
  • the method comprises an additional step of distilling the biodiesel. In some embodiments, the distilled biodiesel has an ester content of at least 99.5%.
  • the method further comprises transferring the heavy phase produced in step h) to a second settlement tank, then skimming the top phase comprising FFA, and removing the bottom phase comprising crude glycerol.
  • the glycerol is at least partially purified and stored.
  • hydrochloric acid is added to the second settlement tank.
  • glycerol purification produces a byproduct comprising oleins.
  • the olein byproduct is saved for use in a further reaction for producing biodiesel.
  • the method further comprises adding citric acid to the feedstock mixture before centrifugation at step i).
  • the method further comprises adding the trace amount of methanol and moisture from the centrifuged light phase of step j) to a bioreactor for use in a further reaction for producing biodiesel.
  • FIG. 1 is a flow diagram of the disclosed method of producing a biodiesel.
  • DETAILED DESCRIPTION OF THE DISCLOSURE [0022] The present disclosure is directed to a method of producing a biodiesel. In certain embodiments, the biodiesel has a high ester content.
  • the high ester content is at least 90.0, 91.0, 92.0, 93.0, 94.0, 95.0, 95.5, 96.0, 96.5, 97.0, 97.5, 98.0, 98.5, 99.0, 99.5 or 100%
  • the biodiesel has an ester content of at least 95%.
  • the biodiesel has an ester content of greater than 99.5%.
  • the methods provided herein include providing a feedstock comprising free fatty acids (FFA), tryglyceride and in certain embodiments, other impurities.
  • the impurities can include water.
  • the feedstock is at least 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69 or 70 % FFA.
  • the feedstock also includes about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20% impurities.
  • the balance of the feedstock is triglyceride.
  • the feedstock is 60-70% FFA, 25-35% triglyceride with the balance of the feedstock being impurities. According to certain embodiments the feedstock is about 50% FFA, about 30% triglyceride and about 20% impurities. According to certain embodiments the feedstock is 50% FFA, 30% triglyceride and 20% impurities.
  • the feedstock is combined with biodiesel and ethanol. The biodiesel and ethanol are added to reduce the melting point of the mixture. According to certain embodiments, the melting point of the mixture is reduced to below 35, 36, 37, 38, 39, 40, 41, 42, 43, 44 or 45 °C.
  • the melting point of the mixture is reduced to below about 39 °C. According to certain embodiments, the melting point of the mixture is reduced to below 39 °C. [0025] In order to reduce the melting point of the mixture an amount of ethanol is added so that ethanol is up to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15% of the mixture w/v.
  • an amount of ethanol is added so that ethanol is up to 10% of the mixture w/v.
  • the feedstock either subject to treatment with biodiesel and/or ethanol or not, is added to a reactor.
  • enzyme is also added to the reactor.
  • enzyme is added so that it makes up about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9 or 1.0% of the total mixture in the reactor.
  • enzyme is added so that it makes up about 0.3% of the total mixture in the reactor.
  • the enzyme catalyzes at least one of transesterification and esterification reactions.
  • the enzyme catalyzes transesterification and esterification reactions.
  • the mixture is agitated while in the reactor.
  • Methanol is then gradually added to the mixture in the reactor.
  • the methanol is added over a period of at least 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 hours up to 15-20 hours.
  • the methanol is added over a period of at least 4 hours up to 15-20 hours.
  • the methanol is added over a period of about 4 hours.
  • the methanol is added over the period at a volume that is at least 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15% of the mixture.
  • the methanol is added over the period at a volume that is at least 11% of the mixture up to 15-20% of the mixture. According to certain embodiments, the methanol is added over the period at a volume that is about 11% of the mixture. [0028] In certain embodiments, additional methanol is then added to the mixture. This additional amount of methanol can be about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20% of the volume of the mixture. In certain embodiments, the additional amount of methanol can be about 15% of the volume of the mixture. This additional amount of methanol is added over a period of time. This period of time can be at least 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 hours up to 25 hours.
  • the additional amount of methanol is added over a period of 10-15 hours.
  • the mixture in the reactor is tested for the concentration of one or more of ester, FFA and triglycerides.
  • concentration of FFAs is reduced to at most 1, 2, 3, 4, 5, 6, 7 or 8% of the total mixture w/v then a basic solution is added to the mixture.
  • a basic solution is added to the mixture.
  • the concentration of FFAs is reduced to at most 3% of the total mixture w/v then a basic solution is added to the mixture. In certain embodiments, when the concentration of FFAs is reduced to about 3% of the total mixture w/v then a basic solution is added to the mixture.
  • the basic solution is NaOH. According to certain embodiments, the NaOH solution is about a 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15% solution of NaOH.
  • the NaOH solution is about a 10% solution of NaOH.
  • the reaction is stopped when the concentration of FFA in the mixture is at most 0.1, 0.2, 0.3, 0.40.5, 0.6, 0.7, 0.8, 0.9%, 1.0%, 1.1%, 1.2%, 1.3%, 1.4%, 1.5%, 1.6%, 1.7%, 1.8%, 1.9%, 2.0%, 2.1%, 2.2%, 2.3%, 2.4% or 2.5% w/v.
  • the mixture is then transferred to an intermediate tank.
  • the mixture is added to a flash drying chamber.
  • the flash drying chamber is capable of applying increased heat and reduced pressure to the mixture.
  • the elevated temperature is about 60, 61, 62, 63, 64, 65, 66, 67, 68, 69 or 70 °C. In certain embodiments, the elevated temperature is about 65 °C. In certain embodiments, the reduced pressure is about 650, 660, 670, 680, 670, 700, 710, 720 or 730 Torr. In certain embodiments, the reduced pressure is about 700 Torr. In certain embodiments,
  • the flash dying chamber is an A4 reactor used in a biodiesel plant.
  • excess methanol is removed from the mixture.
  • the excess methanol is about 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20% of the mixture w/v.
  • the excess methanol is about 15% of the mixture w/v.
  • the mixture is then allowed to settle. In certain embodiments, this settling step is done in a settlement tank.
  • the settlement tank is an S1 tank. The settlement of the mixture results in a light and heavy phase.
  • the light phase comprises most of the biodiesel and some quantity of methanol and water.
  • the light phase contains at least 90, 91, 92, 93, 94, 95, 96, 97, 98, 99 or 100% of the biodiesel from the total mixture.
  • the heavy phase comprises most of the soap, glycerol and water in the mixture.
  • the heavy phase contains at least 90, 91, 92, 93, 94, 95, 96, 97, 98, 99 or 100% of the soap, glycerol and water from the total mixture.
  • the light and heavy phases are separated. In certain embodiments, the light phase undergoes centrifugation to separate residual methanol and water from the biodiesel.
  • the light phase contains at least 90.0, 91.0, 92.0, 93.0, 94.0, 95.0, 95.5, 96.0, 96.5, 97.0, 97.5, 98.0, 98.5, 99.0% biodiesel. In certain embodiments, the light phase is at least 96.5% biodiesel.
  • the light phase can undergo additional distillation. As a result of the optional distillation, the light phase can contain at least 93.0, 94.0, 95.0, 95.5, 96.0, 96.5, 97.0, 97.5, 98.0, 98.5, 99.0, 99.5 or 100% biodiesel.
  • the distilled light phase is at least 99.5% biodiesel.
  • the heavy phase is subject to a process which separates FFA from their salts. In certain embodiments, this process includes acid treatment. According to certain embodiments, the acid is hydrochloric acid. According to certain embodiments, the FFA are skimmed away from the remainder of the heavy phase. According to certain embodiments, the glycerol is isolated and concentrated. [0035] It is to be understood that the methods described in this disclosure are not limited to particular methods and experimental conditions disclosed herein; as such methods and conditions may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to be limiting.
  • the term“biodiesel” refers to a vegetable oil or animal fat-based diesel fuel consisting of long-chain alkyl esters.
  • the term“feedstock” refers to the starting material from which the biodiesel is produced. In some embodiments, the feedstock comprises 65% free fatty acids (FFA) and 30% glycerol.
  • the term“olein” refers to residual fatty acids. In some embodiments, glycerol purification produces a byproduct comprising oleins.
  • the term“bioreactor” or“flash drying chamber” refers to a vessel that carries out a reaction.
  • bioreactor or flash drying chamber is capable of applying increased heat and reduced pressure to the mixture.
  • Example 1 Enzymatic Conversion of Biodiesel
  • Feedstock which is 65% free fatty acids (FFA) and 30% triglyceride (the balance is made up of unsaps/impurities) is mixed with biodiesel and maximum 10% ethanol to reduce melting point down to 39 o C. If the melting point of feedstock is in any case 39 o C or less, the feedstock does not need any pretreatment.
  • the feedstock with 0.3% enzyme is fed into the reactor. The reaction requires 11% methanol dosing which is pumped into the reactor 4 hours from the start of the reaction. The reactants inside the reactor are under constant agitation. An additional 15% methanol is then added to the reactor at the rate of 1% per hour.
  • the homogenous solution inside the reactor is tested for ester, FFA, and triglycerides. Once the FFA is down to 3%, NaOH solution (10% concentration) is added to the reactor. Once the FFA is down to 0.3%, the reaction is stopped and the entire feedstock is transferred to an intermediate tank. [0046] From the intermediate tank, the feedstock is fed into the A4 reactor in the biodiesel plant. A4 is a flash drying chamber which recovers the excess 15% methanol. The temperature is 65 o C and the vacuum is 700.
  • the reaction is then sent to the S1 tank which is a settlement tank where the light phase consisting of all the biodiesel and some small quantity of methanol and moisture is separated from the heavy phase consisting of soap, glycerol, and water is separated.
  • the lighter phase goes to the centrifuge for clean- up and the heavy phase goes to S2 for splitting soap to FFA and salts.
  • FFA floats to the top and is skimmed.
  • the bottom phase is crude glycerol which is then refined.
  • the cleaned from the centrifuge is then either stored as biodiesel, or sent to the distillation column for distillation.
  • the biodiesel thus produced has an ester content of 96.5%.

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Abstract

L'invention concerne des compositions et des procédés pour la production d'un biodiesel présentant une teneur en ester spécifiée.
PCT/US2018/027548 2017-04-13 2018-04-13 Procédés et compositions pour la production de biodiesel WO2018191653A1 (fr)

Applications Claiming Priority (2)

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US201762485348P 2017-04-13 2017-04-13
US62/485,348 2017-04-13

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WO2018191653A1 true WO2018191653A1 (fr) 2018-10-18

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114250116A (zh) * 2021-12-30 2022-03-29 唐河金海生物科技有限公司 将生物酶酯化和超临界技术相结合生产生物柴油的方法
WO2023037360A1 (fr) * 2021-09-13 2023-03-16 Univice M.E Ltd Procédés de fabrication de biodiesel à partir de déchets gras
WO2024189621A1 (fr) * 2023-03-13 2024-09-19 Univice M.E Ltd Procédés de fabrication de biodiesel à partir de déchets gras

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6712867B1 (en) * 1999-08-18 2004-03-30 Biox Corporation Process for production of fatty acid methyl esters from fatty acid triglycerides
US20070282118A1 (en) * 2003-12-30 2007-12-06 Gupta Ashok K Process For Preparing Fatty Acid Alkylesters Using As Biodiesel
US7666234B2 (en) * 2004-10-20 2010-02-23 Council Of Scientific And Industrial Research Process for the preparation of fatty acid methyl ester from triglyceride oil by transesterification
US20100132252A1 (en) * 2007-03-23 2010-06-03 Bio Energies Japan Corporation Method of producing biodiesel fuel
US9133406B2 (en) * 2009-09-25 2015-09-15 REG Life Sciences, LLC Production of fatty acid derivatives

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6712867B1 (en) * 1999-08-18 2004-03-30 Biox Corporation Process for production of fatty acid methyl esters from fatty acid triglycerides
US20070282118A1 (en) * 2003-12-30 2007-12-06 Gupta Ashok K Process For Preparing Fatty Acid Alkylesters Using As Biodiesel
US7666234B2 (en) * 2004-10-20 2010-02-23 Council Of Scientific And Industrial Research Process for the preparation of fatty acid methyl ester from triglyceride oil by transesterification
US20100132252A1 (en) * 2007-03-23 2010-06-03 Bio Energies Japan Corporation Method of producing biodiesel fuel
US9133406B2 (en) * 2009-09-25 2015-09-15 REG Life Sciences, LLC Production of fatty acid derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023037360A1 (fr) * 2021-09-13 2023-03-16 Univice M.E Ltd Procédés de fabrication de biodiesel à partir de déchets gras
CN114250116A (zh) * 2021-12-30 2022-03-29 唐河金海生物科技有限公司 将生物酶酯化和超临界技术相结合生产生物柴油的方法
CN114250116B (zh) * 2021-12-30 2023-11-28 唐河金海生物科技有限公司 将生物酶酯化和超临界技术相结合生产生物柴油的方法
WO2024189621A1 (fr) * 2023-03-13 2024-09-19 Univice M.E Ltd Procédés de fabrication de biodiesel à partir de déchets gras

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