WO2016060450A1 - Procédé de préparation de biocarburant pour l'aviation de qualité élevée faisant appel à une huile autre qu'une huile de cuisson, et biocarburant pour l'aviation ainsi préparé - Google Patents

Procédé de préparation de biocarburant pour l'aviation de qualité élevée faisant appel à une huile autre qu'une huile de cuisson, et biocarburant pour l'aviation ainsi préparé Download PDF

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WO2016060450A1
WO2016060450A1 PCT/KR2015/010800 KR2015010800W WO2016060450A1 WO 2016060450 A1 WO2016060450 A1 WO 2016060450A1 KR 2015010800 W KR2015010800 W KR 2015010800W WO 2016060450 A1 WO2016060450 A1 WO 2016060450A1
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oil
bio
edible
oils
catalyst
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PCT/KR2015/010800
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English (en)
Korean (ko)
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황경란
이진석
한정식
이경환
최일호
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한국에너지기술연구원
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Publication of WO2016060450A1 publication Critical patent/WO2016060450A1/fr

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    • 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
    • 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
    • C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • 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 high quality 100% bio-air fuel from non-edible fats and oils and bio-air oil produced thereby.
  • biomass is a carbon compound in which carbon dioxide, a global warming material, is fixed using solar energy
  • biomass is an energy storage material having a characteristic of carbon compound together with fossil fuel.
  • biomass described above is often used for vegetable sources such as corn, soybean, linseed, sugar cane and palm oil, but the term is generally used for all living organisms, or their metabolism, which is part of the carbon cycle. It can be extended to by-products.
  • FIG. 1 is a process chart showing a process for manufacturing a conventional bio-air fuel, in order to produce bio-air fuel according to the prior art, hydrogen is required for the deoxygenation reaction, selective pyrolysis and isomerization reaction, and paraffin through this process.
  • Synthetic Paraffinic Kerosene (SPK) having a series of hydrocarbons is prepared.
  • US Patent Publication Nos. US 2004/0230085 and US 2014/0275670 which are conventional techniques for minimizing the amount of hydrogen used in a bio-air fuel production process, are basically (1) deoxygenation for bio-air fuel production. Reaction (2) Isomerization and selective pyrolysis require two steps (US 2004/0230085).
  • Figure 2 is a reaction schematic showing the three forms of deoxygenation reaction through hydrogenation in the conventional bio-air oil production process, the deoxygenation reaction according to the form of oxygen is removed as shown in Figure 2, Three methods exist, and in particular, the development of a catalyst for the decarboxylation reaction of removing intramolecular oxygen in the form of carbon dioxide, which has relatively low hydrogen consumption, has been mainly carried out (US 2014/0275670).
  • US Patent Publication No. US 2014/0005448 discloses a 100% bio-air fuel by adding a step of separating a hydrocarbon having a short carbon number of a paraffinic hydrocarbon and modifying it into an aromatic in a paraffinic hydrocarbon produced after hydrogenation deoxygenation.
  • a reactor for hydrocarbon reforming was operated under a reforming temperature of 300 to 520 ° C., a hydrogen pressure of 3 to 27 bar, and a hydrogen to carbon ratio of 0.5 to 10.
  • the mixed bioair fuels contained 8 to 25% by weight of renewable aromatics.
  • the above method requires an additional process such as a separation process and a reforming process, and is a process in which hydrogen is consumed in large quantities.
  • the reaction was carried out while supplying a reaction temperature of 300 to 500 °C, hydrogen pressure of 20 to 150 bar, 100 to 5000 ml of hydrogen per 1 ml of the raw material, The conversion rate reached 92 to 99.9%.
  • the aromatic fuel oil range accounted for 35 to 60% of the total aromatic hydrocarbon content of 1 to 18%.
  • the present invention has been made to solve the above problems, the object of the present invention is 100% having a high energy density as a raw material for non-edible fats and oils through a single-step process without supplying hydrogen It is to provide a method for producing bio aviation oil.
  • the present invention provides a process for preparing paraffins through deoxygenation, isomerization and aromatization reactions from non-edible fats and liquids in the presence of a catalyst without adding hydrogen. Forming a reaction product comprising the system hydrocarbon and the aromatic compound; And (b) distilling the reaction product to extract the aviation oil.
  • non-edible fat and oil proposes a method for producing bio-avid oil using non-edible fat, characterized in that the triglyceride (triglyceride) or free fatty acid (free fatty acid) as a main component.
  • non-edible oil and fat is one selected from the group consisting of palm fatty acid distillate (PFAD), non-edible dark oil derived from edible oil, microalgae-derived oil, jatropha oil, camelina oil, waste oil, and animal fats and oils. It proposes a bio-air oil production method using a non-edible fat, characterized in that the above made.
  • PFAD palm fatty acid distillate
  • the catalyst includes a support and a metal particle supported on the support, the support is a zeolite in which the volume fraction of the meso pores is larger than the volume fraction of the micropores, the metal particles are palladium (Pd), platinum (Pt)
  • the present invention proposes a method for producing bio-avid oil using non-edible fats and oils, characterized in that it is made of at least one metal selected from the group consisting of nickel (Ni), gallium (Ga), copper (Cu), and zinc (Zn).
  • step (a) proposes a bio-air oil production method using a non-edible fat, characterized in that carried out at a pressure of 10 to 50 bar and a temperature of 200 to 370 °C formed by an inert gas.
  • the present invention is prepared by the method for preparing bio-air oil using the non-edible fats and oils, wherein the isoparaffinic hydrocarbon and the aromatic compound are 30 to 70% by weight. It proposes a bio aviation oil comprising a.
  • the method for producing high quality bio-air fuel using non-edible fats and oils according to the present invention is a starting material by inducing deoxygenation, isomerization and aromatization reactions through a single step process by optimizing catalyst and reaction conditions without adding hydrogen.
  • High-density, high-quality, 100% bioair fuels including normal paraffinic hydrocarbons, isoparaffinic hydrocarbons and aromatics, can be produced directly and selectively from non-edible fats and oils, which is very economical in terms of manufacturing cost reduction and process simplification.
  • 1 is a process chart showing a conventional bio-air fuel production process.
  • Figure 2 is a reaction schematic showing three forms of deoxygenation reaction through hydrogenation in the conventional bio-air oil production process.
  • Figure 3 is a graph showing the oxygen removal rate in the raw material and the type and content of the components included in the bio-air oil prepared according to Example 2 of the present application.
  • Figure 4 is a graph showing the oxygen removal rate in the raw material and the type and content of the components included in the bio-air oil prepared according to Example 3 of the present application.
  • Bio-air oil production method (a) paraffinic hydrocarbons through the deoxygenation, isomerization and aromatization reaction from the liquid non-edible fat in the presence of a catalyst without the addition of hydrogen And forming a reaction product comprising the aromatic compound; And (b) distilling the reaction product to extract aviation oil.
  • the non-edible fats and oils supplied as a raw material to the reaction made in step (a) is composed of a hydrocarbon containing a carboxyl group as a non-edible biomass and is a mixture having no or more than one double bond in the hydrocarbon structure.
  • triglyceride (triglyceride) or free fatty acid (free fatty acid) may be included as a main component, in this case, the carbon number of the fatty acid group or free fatty acid contained in the triglyceride is preferably 10 to 24, More preferably, it may be 16-20.
  • non-edible fats and oils include palm fatty acid distillate (PFAD), non-edible dark oils derived from edible oils and fats, oils derived from microalgae, jatropha oil, camelina oil, waste oils, animal oils or mixtures thereof. However, it is not necessarily limited thereto.
  • PFAD palm fatty acid distillate
  • non-edible dark oils derived from edible oils and fats oils derived from microalgae, jatropha oil, camelina oil, waste oils, animal oils or mixtures thereof.
  • PFAD palm fatty acid distillate
  • Table 1 is a table showing the composition and characteristics of some substances belonging to the non-edible fats and oils used in the present invention.
  • non-edible fats and fats are present in the form of gel or gel rather than liquid according to the content and season of free fatty acid, it is preferable to add the non-edible fat to the reactor in the state of maintaining at a temperature of from room temperature to 60 ° C. Do.
  • the catalyst used in the reaction in this step (a) is deoxygenated not only to remove oxygen present in the hydrocarbon molecular structure included in the non-edible fats and oils, but also to mediate isomerization and conversion to aromatic hydrocarbons. It is preferred to be a bifunctional catalyst composed of a metal having an active point and a support having an acid point.
  • a zeolite having a medium and strong Bronsted acid point which is advantageous for cracking and isomerization, can be used, considering the carbon number range of the bio-air fuel fraction, among which 2 nm in diameter. It is preferable to use a zeolite having a large volume fraction of mesopores having a diameter of 2 to 50 nm as compared to the micropore volume fraction below, and furthermore, finer than a large pore zeolite or 10 zeolites having 10 or 12 oxygen atoms. It is more preferable to use zeolites having large pores and having 3D channels, which are advantageous for cracking reactions of hydrocarbons having long chains.
  • the Si / Al ratio of the zeolite affects the distribution of the product after the reaction and is operated under optimum reaction conditions to obtain the desired distribution.
  • the metal active material to be supported on the support includes at least one metal selected from the group consisting of palladium (Pd), platinum (Pt), nickel (Ni), gallium (Ga), copper (Cu) and zinc (Zn). Particles consisting of can be used.
  • the deoxygenation, isomerization and aromatization reactions carried out in this step (a) are carried out in a reactor in which the non-edible fats and oils as raw materials are supplied to the reactor in the presence of the catalyst described above without hydrogen being supplied to the reaction. It is characterized by the anhydrous catalyst conversion process carried out.
  • the reaction of this step is preferably carried out at a temperature of 200 °C to 370 °C, more preferably can be carried out at a temperature of 250 °C to 350 °C.
  • the type and content of the constituents of the reaction product obtained through this step are greatly influenced by the reaction temperature, operating at a relatively high temperature to increase the content of aromatic products, and relatively low temperature to increase the content of normal and isomerized hydrocarbons. You can drive at a relatively high temperature to increase the content of aromatic products, and relatively low temperature to increase the content of normal and isomerized hydrocarbons. You can drive at
  • the initial reactor pressure 10 bar to 50 bar by using an inert gas such as nitrogen, helium or argon so that the reaction can proceed while the raw material is maintained in the liquid phase at the reaction temperature.
  • an inert gas such as nitrogen, helium or argon
  • reaction time of the anhydrous catalytic decomposition process in this step may vary depending on the acidity of the catalyst used, but is preferably made in the range of 0.5 to 6 hours, more preferably by reacting for 1 to 3 hours Reaction products including paraffinic hydrocarbons and aromatic compounds can be prepared.
  • step (a) may be configured to recover and reuse the used catalyst.
  • the step (b) is a step of obtaining bio-air fuel by distilling the air product by distilling the reaction product obtained in the step (a) because it can use a known technique such as vacuum distillation (vaccum distillation) Will be omitted.
  • the method for producing high-quality bio-air fuel using non-edible fats and oils according to the present invention described above, a plurality of hydrogenation processes for supplying a large amount of hydrogen for deoxygenation and isomerization of raw materials are required, and after completion of the hydrogenation process, Unlike the existing multistage aviation oil production process, which requires the addition of a separate petroleum aromatic compound to satisfy the quality, the single-step process for deoxygenation, isomerization and aromatization reaction is performed by optimizing the catalyst and reaction conditions without adding hydrogen.
  • the bio-air oil prepared by the bio-air oil production method using the non-edible fat and oil is composed of 15 to 30% by weight of iso-paraffinic hydrocarbons and 30 to 70% by weight of aromatic compounds, It also contains normal paraffinic (n-paraffin) hydrocarbons, and has a high calorific value, good low temperature characteristics, and a hydrocarbon chain having 12 to 18 carbon atoms that does not contain impurities. have.
  • bio-air fuel in which 5 g by weight of palladium is supported by 10 g of stearic acid or oleic acid, which are non-edible fats and oils, as an active material without solvent.
  • Catalytic reaction was induced using a zeolite catalyst, and the catalytic reaction proceeded at a pressure of 15 bar under a nitrogen atmosphere.
  • Table 2 is a table showing the content and characteristics of the bio-air oil prepared according to the amount of catalyst, reaction temperature and reaction time used in the bio-air oil production process using the non-edible fat and oil according to the first embodiment.
  • the biofuel oil prepared according to Example 1 showed that the conversion rate of non-edible oil and fat was increased as the amount of catalyst supplied increased.
  • the proportion of hydrocarbons between the corresponding C12 and C18 also increased.
  • Figure 3 is a graph showing the oxygen removal rate in the raw material and the type and content of the components included in the bio-air oil prepared according to Example 2 of the present application.
  • the bio-air fuel prepared from the waste cooking oil of Example 2 showed an oxygen removal rate (DO) of 95.5% or 76.1%, and normal paraffinic hydrocarbons at C12 to C18 corresponding to bio-air fuel fractions.
  • DO oxygen removal rate
  • Isoparaffinic hydrocarbons and aromatic compounds accounted for 38-42% of the total product.
  • the normal paraffinic hydrocarbon was 23.5%
  • the isoparaffinic hydrocarbon was 15.8%
  • the aromatic compound was 60.7%.
  • PFAD a non-edible fat and oil raw material
  • Y zeolite Pd (5) / Y
  • beta loaded with 5% by weight of palladium as an active material without solvent Catalytic reaction was induced using 3 g of zeolite (Pd (5) / BEA) catalyst, and the catalytic reaction proceeded at 300 ° C. for 3 hours at a pressure of 15 bar under nitrogen atmosphere.
  • Figure 4 is a graph showing the oxygen removal rate in the raw material and the type and content of the components included in the bio-air oil prepared according to Example 3 of the present application.
  • the bio-air oil prepared by the PFAD of Example 3 showed 94.3% deoxygenation degree in the beta zeolite catalyst and 80% deoxygenation degree in the Y zeolite catalyst.
  • the normal paraffinic hydrocarbon was 16.2%
  • the isoparaffinic hydrocarbon was 16.8%
  • the aromatic compound was 69%.

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  • 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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

Cette invention concerne un procédé de préparation de biocarburant pour l'aviation faisant appel à une huile autre qu'une huile de cuisson, ledit procédé comprenant les étapes suivantes : (a) la formation d'un produit de réaction contenant un hydrocarbure à base de paraffine et un composé aromatique par désoxygénation, isomérisation et aromatisation d'une huile liquide autre qu'une huile de cuisson en présence d'un catalyseur sans ajout d'hydrogène ; et (b) l'extraction d'une fraction de carburant pour l'aviation par distillation du produit réactionnel. Selon la présente invention, un biocarburant de haute qualité 100 % dédié à l'aviation ayant une densité d'énergie élevée, contenant un hydrocarbure à base d'isoparaffine et un composé aromatique, peut être directement et sélectivement préparé à partir d'une huile autre qu'une huile de cuisson, qui est un matériau de départ, par optimisation du catalyseur et des conditions de réaction et sans ajout d'hydrogène de façon à induire la désoxygénation, l'isomérisation et l'aromatisation par un procédé en une seule étape, la présente invention étant ce faisant très économique en termes de réduction des coûts de préparation et de simplification de procédé.
PCT/KR2015/010800 2014-10-14 2015-10-14 Procédé de préparation de biocarburant pour l'aviation de qualité élevée faisant appel à une huile autre qu'une huile de cuisson, et biocarburant pour l'aviation ainsi préparé WO2016060450A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019221287A1 (fr) 2018-05-18 2019-11-21 一般社団法人 ＨｉＢＤ研究所 Procédé de production de carburéacteur biologique
CN111036257A (zh) * 2019-06-28 2020-04-21 南京工程学院 用于制备生物航油的多孔框架负载型催化剂及制备方法
WO2023116168A1 (fr) * 2021-12-23 2023-06-29 中国石油天然气股份有限公司 Procédé de préparation de combustible liquide par désoxydation catalytique sélective de graisse et combustible liquide

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101750230B1 (ko) 2016-04-08 2017-06-23 한국에너지기술연구원 촉매를 이용하여 비식용 유지로부터 고품질의 탄화수소 제조 방법
KR20240008450A (ko) 2022-07-11 2024-01-19 한국에너지기술연구원 바이오항공유분 제조용 촉매 및 바이오항공유분 제조방법

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US20130018213A1 (en) * 2010-08-02 2013-01-17 Battelle Memorial Institute Deoxygenation of fatty acids for preparation of hydrocarbons
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US8742183B2 (en) * 2007-12-21 2014-06-03 Uop Llc Production of aviation fuel from biorenewable feedstocks
US20140275670A1 (en) * 2013-03-14 2014-09-18 Ted R. Aulich Process for low-hydrogen-consumption conversion of renewable feedstocks to alkanes

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US7928273B2 (en) * 2005-08-29 2011-04-19 David Bradin Process for producing a renewable fuel in the gasoline or jet fuel range
US20140045239A1 (en) * 2007-07-27 2014-02-13 Swift Fuels, Llc Renewable engine fuel and method of producing same
US8742183B2 (en) * 2007-12-21 2014-06-03 Uop Llc Production of aviation fuel from biorenewable feedstocks
US20130018213A1 (en) * 2010-08-02 2013-01-17 Battelle Memorial Institute Deoxygenation of fatty acids for preparation of hydrocarbons
US20140275670A1 (en) * 2013-03-14 2014-09-18 Ted R. Aulich Process for low-hydrogen-consumption conversion of renewable feedstocks to alkanes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019221287A1 (fr) 2018-05-18 2019-11-21 一般社団法人 ＨｉＢＤ研究所 Procédé de production de carburéacteur biologique
KR20200141087A (ko) 2018-05-18 2020-12-17 잇판샤단호징 에이치아이비디 겡큐쇼 바이오제트 연료의 제조 방법
US11603501B2 (en) 2018-05-18 2023-03-14 Hibd Laboratory Association Method for producing bio-jet fuel
CN111036257A (zh) * 2019-06-28 2020-04-21 南京工程学院 用于制备生物航油的多孔框架负载型催化剂及制备方法
CN111036257B (zh) * 2019-06-28 2022-11-25 南京工程学院 用于制备生物航油的多孔框架负载型催化剂及制备方法
WO2023116168A1 (fr) * 2021-12-23 2023-06-29 中国石油天然气股份有限公司 Procédé de préparation de combustible liquide par désoxydation catalytique sélective de graisse et combustible liquide

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