WO2025003741A1 - Procédé pour la production de biopropane à partir d'huiles résiduaires - Google Patents

Procédé pour la production de biopropane à partir d'huiles résiduaires Download PDF

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Publication number
WO2025003741A1
WO2025003741A1 PCT/IB2023/056874 IB2023056874W WO2025003741A1 WO 2025003741 A1 WO2025003741 A1 WO 2025003741A1 IB 2023056874 W IB2023056874 W IB 2023056874W WO 2025003741 A1 WO2025003741 A1 WO 2025003741A1
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Prior art keywords
saponification
carboxylate
glycerol
residual oils
carried out
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English (en)
Spanish (es)
Inventor
Laura Haydée AZÓCAR ULLOA
Fabiola Alejandra VALDEBENITO ESCOBAR
Carolina Alejandra AGUIRRE CÉSPEDES
Robinson Eduardo MUÑOZ GONZÁLEZ
Ruby Alejandra RIVEROS ARRIAGADA
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Universidad Catolica de la Santisima Concepcion
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Universidad Catolica de la Santisima Concepcion
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Priority to PCT/IB2023/056874 priority Critical patent/WO2025003741A1/fr
Publication of WO2025003741A1 publication Critical patent/WO2025003741A1/fr
Anticipated expiration legal-status Critical
Priority to CONC2026/0000515A priority patent/CO2026000515A2/es
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C9/00—Aliphatic saturated hydrocarbons
    • C07C9/02—Aliphatic saturated hydrocarbons with one to four carbon atoms
    • C07C9/08—Propane
    • 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
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • 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
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/12—Liquefied petroleum gas

Definitions

  • the present invention relates to the field of technologies for the valorisation of domestic and/or industrial waste and in particular provides a method for the production of biopropane from residual oils.
  • US 2012/157728 AA discloses a method for producing bio-naphtha from a mixture of fats and oils of natural origin.
  • the oils and fats are treated and, after treatment, they are subjected to a saponification reaction from which soap and glycerol are obtained.
  • the soap obtained is subjected to a decarboxylation process from which bio-naphtha is obtained, which is a liquid biofuel similar to gasoline.
  • this document does not perform a subsequent treatment of the glycerol obtained, which results in a lower yield in the biofuel production process.
  • the present invention provides a method for the production of biopropane from residual oils, which is characterized in that it comprises the steps of: carrying out a saponification of the residual oils, obtaining carboxylate and glycerol; carrying out a separation of the carboxylate and glycerol; carrying out a fermentation of the glycerol obtained afterwards. saponification to obtain 1,3-propanediol; oxidation of 1,3-propanediol to obtain propanedioic acid; saponification of propanedioic acid to obtain carboxylate; and pyrolysis of the carboxylate obtained from residual oils and of the carboxylate obtained from propanedioic acid to obtain biopropane.
  • Fig. 1 illustrates a flow chart of a first embodiment of the method that is the object of the present invention.
  • the present invention provides a method (1) for the production of biopropane (10) from waste oils (100) comprising the steps of:
  • the method (1) may comprise performing a first saponification operation (2) of a first quantity of residual oils (100) and performing a second saponification operation (2) of a second quantity of residual oils (100).
  • the saponification (2) of the propanedioic acid (41) may be performed in conjunction with the second saponification operation (2) of the second quantity of residual oils (100).
  • the saponification (2) of the propanedioic acid (41) may be performed in conjunction with the second saponification operation (2) of the second quantity of residual oils (100).
  • the saponification (2) of the propanedioic acid (41) can be carried out independently of the saponification (2) of the residual oils (100).
  • the saponification (2) of the residual oils (100) can be carried out substantially continuously.
  • the propanedioic acid (41) obtained after the oxidation (4) of the 1,3-propanediol (31) can be introduced substantially continuously into the saponification process (2) of the residual oils (100).
  • biopropane will be understood as a biofuel based on propane and having properties similar to liquefied petroleum gas.
  • the method (1) may additionally comprise the step of filtering the residual oils (100) prior to the step of carrying out the saponification (2), separating particulate material from the residual oils (100).
  • the technique used to carry out said filtration does not limit the scope of the present invention and may depend, for example, on the specific implementation of the method (1) that is the object of the present invention, as well as on the origin and nature of said residual oils (100).
  • the filtration of the residual oils (100) may be carried out at a temperature between 50 °C and 80 °C.
  • the saponification step (2) of the residual oils (100) can be carried out using NaOH as a base, according to the reaction illustrated in scheme 1:
  • the saponification step (2) of the residual oils (100) can be carried out at a molar ratio of NaOH to fatty acids of between 0.5 and 2.5. In another more preferred embodiment, without limiting the scope of the present invention, the saponification step (2) of the residual oils (100) can be carried out at a molar ratio of NaOH to fatty acids of between 0.5 and 2.5. residual (100) can be carried out at a temperature between 20 °C and 40 °C, more preferably between 25 °C and 35 °C.
  • the separation of the carboxylate (21) and the glycerol (22) obtained after the saponification (2) of the residual oils (100) may comprise a decantation step to obtain a liquid phase, corresponding to glycerol (22) and water, and a solid phase, corresponding to carboxylate (21).
  • the method (1) may additionally comprise pressing the solid phase obtained after the decantation, in order to obtain a higher concentration of carboxylate (21).
  • the carboxylate (21) can be dehydrated, ground and/or sieved prior to the step of performing the pyrolysis (5).
  • the particle size of the carboxylate (21) after the dehydration, grinding and/or sieving stages does not limit the scope of the present invention.
  • the fermentation (3) of the glycerol (22) can be carried out under anaerobic or micro-aerobic conditions.
  • the fermentation (3) of the glycerol (22) can be carried out using a strain of Klebsiella pneumoniae DSM 2026, at a pH between 5.0 and 8.0 and at a temperature between 34 °C and 39 °C.
  • the oxidation (4) of 1,3-propanediol (31) can be done using a Jones oxidation reaction at room temperature, according to the reaction scheme illustrated in Scheme 2:
  • the saponification (2) of propanedioic acid (41) can be carried out using NaOH as a base, wherein the saponification (2) of propanedioic acid (41) is carried out at a molar ratio of propanedioic acid (41) to NaOH of 1.5.
  • the pyrolysis (5) of the carboxylate (21) is carried out using a fluidized bed reactor, with a temperature between 550 °C and 700 °C.
  • a fluidized bed reactor with a temperature between 550 °C and 700 °C.
  • other pyrolysis methods (5) are also applicable to the method (1) for producing biopropane (10) which is the object of the present invention, without limiting the scope of the protection requested.
  • Collected frying waste oil was subjected to a filtration process to remove particulate matter present.
  • the process was carried out at temperatures between 50 °C and 80 °C in order to facilitate filtration.
  • Filtration was performed using a vacuum filtration system consisting of a Büchner funnel, a Kitasato flask, filter paper and a vacuum pump. At this stage, drying of the oil was not required.
  • Carboxylates were produced through the saponification of previously filtered residual frying oils obtained from examples 1 and 2. The process additionally generated glycerol and water as secondary products.
  • the process started with an amount of oil calculated from the stoichiometry of the triglyceride saponification reaction (Scheme 1) under a molar ratio of 0.5 to 2.5 NaOH/fatty acid.
  • the mass of NaOH used was calculated from the stoichiometry of the reaction, considering approximately a 10% excess.
  • the calculated mass of NaOH was diluted in water until reaching a concentration of 23% m/v.
  • the NaOH solution was added to the oil, under constant stirring and at room temperature for approximately 10 minutes.
  • the reaction mixture was then left to settle for 24 hours, until phase separation was observed, where the solid phase corresponds to the carboxylate and the liquid phase to the glycerol.
  • Example 4 Separation of carboxylate and glycerol
  • the decanted mixture obtained from the previous example was subjected to a separation to separate the carboxylate from the glycerol.
  • the solid phase, corresponding to the carboxylate was separated from the liquid phase, corresponding to the glycerol.
  • the solid phase obtained from Examples 3 and 4 was conditioned for use in the carboxylate pyrolysis stage. For this, the solid phase was dried in a convective tunnel between 70 °C and 100 °C for between 20 h and 30 h. The dried product was ground and sieved, collecting the fraction remaining between the 500 and 250 pm sieves, according to the requirements of the subsequent pyrolysis study.
  • the liquid phase obtained from Examples 3 and 4 corresponding to residual glycerol, was conditioned to be subsequently taken to the biotechnological fermentation process to produce 1,3-propanediol. For this, ethanol was poured onto the liquid phase in order to extract the glycerol. Upon adding the ethanol, a brown liquor was obtained containing dissolved glycerol, water and other colored impurities. In addition, a pale yellow precipitate was formed, corresponding to residual carboxylate.
  • the liquid fraction was filtered to separate the remaining carboxylates, followed by evaporation of all the ethanol in a rotary evaporator.
  • the liquid concentrate obtained was cooled in a water-ice mixture and then neutralized with a 20% m/v hydrochloric acid solution until a pH of around 6.0 was obtained, thus generating the precipitation of fatty acids and carboxylates that were dissolved in the concentrated liquor.
  • the precipitated residues, corresponding to fatty acids and carboxylates, were separated by vacuum filtration.
  • the liquid fraction was heated to between 100 °C and 110 °C, after which activated carbon was added and stirred for approximately 10 minutes to adsorb the colored impurities. This mixture was then filtered while hot to remove the activated carbon, obtaining a pale yellow solution. Finally, this solution was distilled to remove as much water as possible from the glycerol. The final liquid obtained, rich in glycerol, had a viscous appearance and a pale yellow color.
  • Example 8 Implementation of glycerol conditioning
  • the liquid concentrate obtained was cooled in a water-ice mixture and then neutralized with 500 ml of a 20% m/v hydrochloric acid solution, until a pH of around 6.0 was obtained, thus generating the precipitation of the fatty acids that were dissolved in the concentrated liquor.
  • the precipitated fatty acids were separated by vacuum filtration and the liquid fraction was heated to 105 °C, activated carbon was added to adsorb the colored impurities and the mixture was stirred for 10 minutes. This mixture was then filtered while hot to remove the activated carbon, obtaining a pale yellow solution. Finally, this solution was distilled to remove as much water as possible from the glycerol.
  • the final liquid obtained, rich in glycerol had a viscous appearance of a pale yellow color.
  • Example 9 Obtaining 1,3-propanediol from glycerol
  • Glycerol fermentation was carried out using the Klebsiella pneumoniae strain DSM 2026, which was acquired in lyophilized condition, and had to be rehydrated and reactivated according to the DSM2026 technical data sheet of the DSMZ strain bank (Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH). This last step was carried out in two plate reactivation media, one according to the DSM 2026 sheet and another in Columbia agar medium, to select the medium that allows obtaining the highest cell density. The results obtained allowed defining the Columbia Agar medium as the ideal one to obtain the highest cell density.
  • the strain was reactivated in agar culture medium at 37 °C and pH 7.0 for 24 h and was replated using preinoculum for the fermentation and 1,3-propanediol production assays.
  • the assays were performed by adjusting the pH to 7.0 with 12 N NaOH.
  • the useful volume for each assay corresponded to 50% in flasks (100 ml) and the preinoculum used corresponded to 10% of the useful volume of the flasks.
  • glycerol was used as a carbon source at an initial concentration of 40 g/l, but the preinoculum was also previously prepared with the same concentration, finally providing 38.5% to the initial concentration, therefore, the initial concentration was 65 g/l of glycerol in the flask.
  • the culture conditions correspond to 37 °C, pH 7.0 and 150 rpm for 24 h. To carry out the fermentation kinetics, samples were taken every 2 h, during the first 12 h and subsequently a sample at 24 h.
  • the samples were centrifuged (10,000 rpm, 2 e C and 20 min), storing the upper phase (liquid), where the reaction products are found: 1,3-propanediol and the unconsumed substrate (glycerol), which were quantified by gas chromatography coupled to mass spectrometry (GC-MS), and in the lower phase (solid) the cellular concentration of Klebsiella pneumoniae was determined, using dry weight methodology.
  • GC-MS gas chromatography coupled to mass spectrometry
  • Example 10 Optimization of the process for obtaining biomass and 1,3-propanediol
  • Biomass production was optimized by taking as an optimization condition the highest amount of biomass produced (12.28 g/l) in the shortest possible time (8 h), so as not to affect productivity.
  • the selection of the maximum concentration obtained of 1,3-propanediol was carried out under the same criteria as for biomass, that is, the highest concentration obtained (20.79 g/l) was selected in the shortest possible time (8 h), but without penalizing the concentration of 1,3-propanediol by more than 5% with respect to the maximum value obtained. (21.95 g/l).
  • the yield obtained with respect to the initial glycerol was calculated with the value obtained at time zero (65 g/l).
  • Example 11 Glycerol fermentation in a bioreactor
  • the fermentation kinetics of Klebsiella pneumoniae DSM 2026 were performed using batch tests in a 3I bioreactor using commercial glycerol concentrations (WINKLER) of 20 g/l, 40 g/l and 60 g/l. To carry out these fermentations, the concentration of commercial glycerol in the preinoculum was maintained at 40 g/l. In addition to the above, for the preparation of the preinoculum and kinetics, the culture media described by Mitrea et al. (2019) were used, which had to be adjusted to pH 7.0, with 12 N NaOH.
  • WINKLER commercial glycerol concentrations
  • a useful volume of 50% of the total bioreactor volume was used.
  • the preinoculum used corresponded to 10% of the useful volume of the bioreactor volume and the operational conditions of the fermentation were 37 °C, pH 7.0 and 150 rpm for 24 h.
  • glycerol concentration was evaluated at increasing concentrations of commercial glycerol, with the aim of optimizing this variable for the production of 1,3-propanediol. Fermentations were carried out at bioreactor scale using a 3 L steel heater, with pH and temperature control.
  • 1,3-propanediol was identical between the highest concentrations of glycerol used (40 g/l and 60 g/l), with maximum concentrations of approximately 16 g/l of 1,3-propanediol. However, with 20 g/l of glycerol, maximum concentrations of approximately 6 g/l were obtained.
  • Example 12 Production results of 1,3-propanediol
  • Table 1 presents the production parameters of 1,3-propanediol, observing a higher production of 1,3-propanediol with 40 g/l at 12 h of fermentation (15.78 g/l), this condition being selected that achieves a higher conversion of glycerol to 1,3-propanediol in molar ratio, this being 0.48 and 0.47 at 12 h and 10 h respectively.
  • the optimal fermentation time of 10 h is defined since a higher volumetric productivity is obtained (1,55 g 1,3-propanediol /L/h).
  • Example 15 Oxidation of 1,3-propanediol from bioreactor
  • an Erlenmeyer flask was assembled and 100 drops of Jones reagent and 100 ml of the bioreactor culture broth were added. The flask was shaken and its contents were subsequently emptied into a 500 ml separatory funnel, to which 200 ml of petroleum ether were added.
  • the separating funnel was shaken and allowed to settle. Then, 30 ml of water was added and the mixture was allowed to stand until phase separation was observed.
  • the organic phase corresponding to the upper phase, clean and colourless, was collected in a beaker.
  • the solvent was evaporated under a hood overnight, thus obtaining a propanedioic acid.
  • the oxidation reaction yield of the bioreactor broth was 95% calculated by gravimetry.
  • the propanedioic acid obtained from the previous example was saponified with 1.5 molar ratio of NaOH to obtain carboxylate.
  • the carboxylate obtained was dried at 105 °C to determine the reaction yield.
  • Biopropane production from carboxylate was carried out at 550-700 °C and with a carrier gas flow that ensures a residence time of over 2 seconds for the devolatilized pyrolytic gases and products in the reactor.
  • the raw material ground carboxylate from the carboxylate production stage
  • propane, butane and other light olefins are produced, to be carried out of the reactor by the carrier gas.
  • the carriers gas After the products carried by the carrier gas left the reactor, they were taken to a condensation section, which cooled the products, retaining the condensable products.
  • the flow of products that are not condensed was taken to an electrostatic precipitator, precipitating aerosols and condensables that were not previously condensed.
  • the transported products that were not retained and/or precipitated are pyrolytic gases rich in propane/propene (26% approx.), butane, pentane, among other olefins.
  • Example 18 Integrated process Based on the results obtained in the previous examples, the sequence of the integrated method was validated, i.e. incorporating each of the essential stages, for the production of biopropane from residual oils.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

La présente invention concerne un procédé pour la production de biopropane à partir d'huiles résiduaires caractérisé en ce qu'il comprend les étapes de : réalisation d'une saponification des huiles résiduaires, avec obtention de carboxylate et de glycérol ; réalisation d'une séparation du carboxylate et du glycérol ; réalisation d'une fermentation du glycérol obtenu après la saponification pour obtenir du 1,3-propanodiol ; réalisation d'une oxydation du 1,3-propanodiol pour obtenir de l'acide propanedioïque ; réalisation d'une saponification de l'acide propanedioïque pour obtenir du caboxylate ; et réalisation d'une pyrolyse du carboxylate obtenu à partir des huiles résiduaires et du carboxylate obtenu à partir de l'acide propanedioïque pour obtenir du biopropane.
PCT/IB2023/056874 2023-06-30 2023-06-30 Procédé pour la production de biopropane à partir d'huiles résiduaires Ceased WO2025003741A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IB2023/056874 WO2025003741A1 (fr) 2023-06-30 2023-06-30 Procédé pour la production de biopropane à partir d'huiles résiduaires
CONC2026/0000515A CO2026000515A2 (es) 2023-06-30 2026-01-19 Método para la producción de biopropano a partir de aceites residuales

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011012439A1 (fr) * 2009-07-27 2011-02-03 Total Petrochemicals Research Feluy Procédé de production de bio-pétrole à partir de mélanges complexes d'huiles et de graisses existant à l'état naturel
WO2014111598A2 (fr) * 2013-01-21 2014-07-24 Total Research & Technology Feluy Procédé de production de bionaphta à partir de mélanges complexes de graisses et huiles d'origine naturelle
EP2358653B1 (fr) * 2008-11-05 2015-07-22 BioFuel-Solution AB Procédé pour la préparation d'hydrocarbures inférieurs à partir de glycérol
KR102483966B1 (ko) * 2022-09-26 2022-12-30 (주)건강생활연구소 폐유 및 착즙고형분을 이용한 비누 제조방법

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2358653B1 (fr) * 2008-11-05 2015-07-22 BioFuel-Solution AB Procédé pour la préparation d'hydrocarbures inférieurs à partir de glycérol
WO2011012439A1 (fr) * 2009-07-27 2011-02-03 Total Petrochemicals Research Feluy Procédé de production de bio-pétrole à partir de mélanges complexes d'huiles et de graisses existant à l'état naturel
WO2014111598A2 (fr) * 2013-01-21 2014-07-24 Total Research & Technology Feluy Procédé de production de bionaphta à partir de mélanges complexes de graisses et huiles d'origine naturelle
KR102483966B1 (ko) * 2022-09-26 2022-12-30 (주)건강생활연구소 폐유 및 착즙고형분을 이용한 비누 제조방법

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Title
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IGBOKWE VICTOR C., EZUGWORIE FLORA N., ONWOSI CHUKWUDI O., ALIYU GODWIN O., OBI CHINONYE J.: "Biochemical biorefinery: A low-cost and non-waste concept for promoting sustainable circular bioeconomy", JOURNAL OF ENVIRONMENTAL MANAGEMENT, ELSEVIER, AMSTERDAM, NL, vol. 305, 1 March 2022 (2022-03-01), AMSTERDAM, NL , pages 114333, XP093257695, ISSN: 0301-4797, DOI: 10.1016/j.jenvman.2021.114333 *
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MOKLIS MUHAMMAD HARUSSANI, CHENG SHOU, CROSS JEFFREY S.: "Current and Future Trends for Crude Glycerol Upgrading to High Value-Added Products", SUSTAINABILITY, MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL (M D P I), CH, vol. 15, no. 4, CH , pages 2979, XP093257693, ISSN: 2071-1050, DOI: 10.3390/su15042979 *

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