WO2010065001A1 - Procédé pour le craquage catalytique d'huiles végétales et de graisses animales - Google Patents

Procédé pour le craquage catalytique d'huiles végétales et de graisses animales Download PDF

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Publication number
WO2010065001A1
WO2010065001A1 PCT/SK2009/050014 SK2009050014W WO2010065001A1 WO 2010065001 A1 WO2010065001 A1 WO 2010065001A1 SK 2009050014 W SK2009050014 W SK 2009050014W WO 2010065001 A1 WO2010065001 A1 WO 2010065001A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
cracking
oil
particles
lignocellulose
Prior art date
Application number
PCT/SK2009/050014
Other languages
German (de)
English (en)
Inventor
Ján CVENGROŠ
Eduard Buzetski
Karl Kunze
Wolfgang Ligotzky
Original Assignee
Cvengros Jan
Eduard Buzetski
Karl Kunze
Wolfgang Ligotzky
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 Cvengros Jan, Eduard Buzetski, Karl Kunze, Wolfgang Ligotzky filed Critical Cvengros Jan
Publication of WO2010065001A1 publication Critical patent/WO2010065001A1/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
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • 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
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • 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
    • C10G2300/1014—Biomass of vegetal origin
    • 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
    • C10G2300/1018—Biomass of animal origin
    • 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
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4006—Temperature
    • 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
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4012—Pressure
    • 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 invention relates to a process for the catalytic cracking of vegetable oils and / or animal fats as natural triacylglycerols with the aim of obtaining liquid condensates, which can be used after a certain treatment as vehicle fuel or as components of a vehicle fuel based on renewable raw materials.
  • alkanes, cycloalkanes and alkylbenzenes can be obtained with a total conversion of up to 100%, with a yield of C12 - Cl 8 alkanes between 65 and 75%.
  • Three independent processes are combined here - deoxygenation, decarboxylation and hydrogenation. After partial isomerization, the products are similar to fossil diesel.
  • the disadvantages of this process which results in products with excellent fuel properties, are that expensive high pressure technology using hydrogen and expensive catalysts are required, and that catalyst activity decreases.
  • the next group of known processes for the catalytic cracking of natural triacylglycerols employs zeolites as catalysts.
  • Zeolite catalysts are crystalline aluminosilicate materials based on a three-dimensional network of AIO4 and SiU4 tetrahedrally linked by oxygen atoms. Zeolites are porous and contain pores of defined size with areas of strong electrostatic field associated with the presence of cations. These areas are catalytically high reactive. The pore size can be changed depending on the requirements of the product.
  • the synthetic zeolite catalysts ZSM-5 or HZSM-5 convert triacylglycerols into gasoline-like products.
  • mesoporous forms of MCM zeolite catalysts produce linear, long-chain hydrocarbons with the boiling range of diesel. The disadvantage of this group of processes is the high price of zeolite catalysts and their limited recyclability as well as problems with the spent catalyst handling.
  • lignocellulose as a cracking catalyst. Mainly they are very low and negligible price and their easy availability.
  • various well-dried waste from agricultural production and from the woodworking industry such as sawdust particles, ground cereal or rape straw, hay, dry leaves, ground corncobs, nutshells, crushed press cake from rapeseed or sunflower seeds, but also waste paper, because of are used to short fibers no reuse, are used.
  • press cake the remaining oil in the cake can be utilized.
  • lignocellulose has a layered structure with staggered lignin layers and cellulosic layers. Removal of the lignin at the elevated temperature during cracking forms a spongy but strong structure with openings similar in size to those in zeolites. In the case of cellulose, these openings are already finished, they were produced during cellulose production. The porous structure then causes, in the same way as in Zeolites, the cracking. Also, the alkali metals present in lignocellulose have the same function that they have in zeolites.
  • the concentration in the reaction mixture is not limited.
  • the lignocellulose catalyst remains after the first application in the form of a porous material of low density, similar to charcoal. It is possible to use it more than once without any treatment, without reducing the yield and without changing the product parameters. Repeated use of the lignocellulose catalyst does not become a phenomenon
  • triacylglycerols used edible oils and kafilery fats.
  • the process of catalytic cracking of triacylglycerols according to the invention is as follows.
  • An appropriate amount of triacylglycerol is added to a batch reactor.
  • It may be vegetable oils such as rapeseed oil, soybean oil, sunflower, palm or cotton oil, inedible oil from the seeds of the plant Jatropha curcas, used frying oils, castor oil, oil from algae and the like.
  • animal fats tallow, lard, chicken fat, fish oils, kafilery fat from carcass utilization and the like can be used.
  • erfmdungsgefflessen catalytic cracking and mixtures of oils and fats can be used.
  • the oils and fats may also contain free fatty acids or other esters as triacylglycerols, e.g. B. Methyl esters of fatty acids.
  • the quality of the oil and fat, the extent of their pollution or depreciation do not play a decisive role here.
  • the oils and fats can be used without any pretreatment in catalytic cracking.
  • the catalyst is lignocellulose or cellulose in the form of granules, a powder, sawdust particles, waste or fibers, and the proportion of catalyst in the reaction mixture should be between 0.5 and 20% by weight, more often between 2 and 12% by weight. % and most often between 5 and 10% by weight.
  • the catalyst particles should be shaped to measure in at least one dimension between 0.01 and 10 mm, and most often between 0.1 and 2 mm.
  • the particles have similar dimensions in all dimensions.
  • the catalyst is made from wood, straw, hay, dry leaves and similar other agricultural waste, and the wood industry such as sawdust particles, corn plants, rape plants and the like.
  • suitable crushing methods such as sawing, grinding, pulverization and the like may be employed.
  • the catalyst should be well dried otherwise it will take time to remove the water, energy will be consumed and the released water will cause intense foaming.
  • the reaction mixture thus prepared is then heated at a rate of 30 to 40 ° C / min. After the initial mixing, no further mixing is required as bubbles of released water and decomposition products naturally mix the mixture.
  • Intensive cracking processes take place between temperatures of 350 and 450 0 C.
  • the reaction mixture is held between these temperatures for about 20 to 25 minutes such that the cracking times are a total of 40 to 50 minutes depending on the batch amount, including the time required to cool the cracking residue.
  • the vapors formed in the reactor during the catalytic cracking of the triacylglycerols according to the invention flow directly into the condenser, which has a sufficient surface area for condensing and cooling and a sufficient length for condensing all condensable components.
  • the condenser / radiator must be sufficiently large be able to absorb even the random eruptions of cracking products.
  • the temperature is measured in the liquid reaction mixture and in the steam inlet into the condenser. No protective atmosphere is generated in the apparatus.
  • the vaporizing components fill the entire space in the apparatus, and thus the contact, the hot products with, the atmospheric oxygen is severely limited.
  • the heating is stopped and the reactor will be empty after cooling.
  • the residue after cracking consists mainly of the catalyst, which is now modified compared to a fresh one.
  • the spent catalyst, after washing, is solid and fragile, with lower density and a structure similar to charcoal.
  • the catalyst residue is in a viscous, tarry liquid, the residue after cracking of the triacylglycerol.
  • the solid fraction of the modified catalyst residue is about 80 to 90% of the mass of the fresh catalyst.
  • the liquid portion of the residue represents about 3 to 8% of the mass of processed oil / fat.
  • the liquid condensate represents about 80 to 90% and the gaseous portion about 5 to 8% of the mass of the processed oil / fat. It seems likely that some of the fresh catalyst will also be converted into cracking products.
  • the mass loss of the fresh catalyst is due to cracking, mainly due to water release.
  • the catalyst can be used repeatedly without a wash and without any other treatment in the reaction. Such use of the catalyst in the same amount of fresh oil resulted in similar product yields as well as similar product compositions. A test for the life of the catalyst has not yet been conducted. The question of its regeneration and recycle is not crucial in this case because of the negligible cost.
  • the used catalyst can be used instead of being burned, after suitable treatment, for example, as charcoal or carbon in steelmaking.
  • the liquid condensate which is the major product of the catalytic cracking of triacylglycerols according to the invention contains a small amount of about 2 to 4% of its mass of water. This water comes, in part from the catalyst, partly from the oil / fat as a product of the cracking reactions. The water is practically insoluble in the liquid condensate, it settles spontaneously and forms a separate phase.
  • the liquid condensate is a light brown or brown liquid with a sharp, irritating odor.
  • Such treated liquid condensate may be used as a fuel component for diesel engines in the form of a blend with fossil diesel fuel, which component may be mixed at any temperature at laboratory temperature.
  • the hydrogenation of this liquid condensate under mild conditions temperature up to 360 0 C, hydrogen pressure to 6 MPa, catalyst NiWZAl 2 O 3 ) is obtained a high quality diesel fuel.
  • the gaseous products of the inventive catalytic cracking of triacylglycerols contain mainly CO and CO 2 , and in small amount also CH 4 , C2H4 and C 2 H 6 .
  • the phenols or alkylphenols produced by cracking lignin can have a positive influence on the oxidation stability of the product.
  • the catalytic cracking of triacylglycerols according to the invention can also be carried out as a continuous process. Examples for carrying out the invention
  • rapeseed oil 250 g were taken after cold pressing and filtering in a filter press in a 1000 ml two-necked glass flask connected to an efficient water-cooled condenser.
  • 25 g of sawdust of fibrous particles with a diameter of about 0.1 mm and a length of about 2 mm mixed 25 g was heated within 10 minutes at 400 0 C, during the next 10 minutes at 420 0 C, during the next 10 minutes 10 minutes at 4 5 0 0 C, and at this temperature, the mixture was held for the next 10 minutes, a total of 40 minutes heated, and then the heating was interrupted.
  • Example 2 250 g rapeseed oil, the same as in Example 1, were mixed in the same apparatus as in Example 1 with 25 g of small cut cereal straw in the form of platelet-shaped particles with dimensions of approximately 0.1 ⁇ 1 ⁇ 3 mm.
  • Similar conditions were selected as in Example 1.
  • the balance of the process gaseous components 8.6% of the mass of the oil used, tar and liquid residue after cracking 3%, solid residue of the catalyst 21 g, liquid condensate, 90%
  • the increase in balance by 2% is due to the catalyst (4 g, probably water).
  • the yield of liquid condensate (organic layer) thereby dropped to 85% of the mass of the oil used.
  • the liquid condensate was then distilled; the fraction of the light end was removed in the temperature range up to 190 0 C in an amount corresponding to 7% of the mass of the oil used.
  • the inventive method for the catalytic cracking of vegetable oils and animal fats can be used in the production of alternative fuels from renewable raw materials for vehicles.
  • the liquid condensate from cracking may be used after a treatment as a fuel or as a component of a fuel for diesel engines.

Abstract

L'invention porte sur un procédé de craquage catalytique de triacylglycérols naturels, l'objectif étant la production de carburants alternatifs, ou de leurs composants, à partir de matières premières renouvelables. Selon l'invention, le catalyseur est la lignocellulose ou la cellulose sous forme de grains, de particules de sciure ou de fibres, les particules de catalyseur ayant au moins une dimension comprise entre 0,01 et 10 mm. Le catalyseur est fabriqué à partir de bois, de paille, de foin, de feuilles sèches et de différents autres déchets de l'agriculture et de l'industrie de transformation du bois. La proportion du catalyseur dans le mélange réactionnel est comprise entre 0,5 et 20 % en poids.
PCT/SK2009/050014 2008-12-04 2009-11-24 Procédé pour le craquage catalytique d'huiles végétales et de graisses animales WO2010065001A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008060558A DE102008060558B4 (de) 2008-12-04 2008-12-04 Verfahren zum katalytischen Cracken von Pflanzenölen und tierischen Fetten
DEDE102008060558.1 2008-12-04

Publications (1)

Publication Number Publication Date
WO2010065001A1 true WO2010065001A1 (fr) 2010-06-10

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PCT/SK2009/050014 WO2010065001A1 (fr) 2008-12-04 2009-11-24 Procédé pour le craquage catalytique d'huiles végétales et de graisses animales

Country Status (3)

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DE (1) DE102008060558B4 (fr)
SK (1) SK287982B6 (fr)
WO (1) WO2010065001A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10184085B2 (en) 2014-06-09 2019-01-22 W. R. Grace & Co.-Conn Method for catalytic deoxygenation of natural oils and greases
WO2021230987A1 (fr) 2020-05-13 2021-11-18 Voyager Therapeutics, Inc. Redirection de tropisme de capsides de vaa

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4102938A (en) * 1977-03-02 1978-07-25 Kalur Vijaya Chandra Rao Production of hydrocarbons by thermolysis of vegetable oils
US4992605A (en) 1988-02-16 1991-02-12 Craig Wayne K Production of hydrocarbons with a relatively high cetane rating
EP0414384A2 (fr) * 1989-08-08 1991-02-27 Nabisco Brands, Inc. Procédé de préparation de triesters de neoalkyletriols
CA1313200C (fr) 1988-02-16 1993-01-26 Wayne K. Craig Production d'hydrocarbures a indice de cetane relativement eleve
WO2008066950A2 (fr) * 2006-05-15 2008-06-05 University Of Georgia Research Foundation Carburants diesel multicomposants miscibles et procédés de transformation d'huile bio
WO2008119525A1 (fr) * 2007-04-03 2008-10-09 Lignosol Gmbh & Co. Kg Installation et procédé pour produire des combustibles à partir de matières premières biogènes

Family Cites Families (2)

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US1960951A (en) * 1932-01-22 1934-05-29 Le Carbone Sa Method of converting by catalysis mineral and vegetable oils
DE10327059B4 (de) * 2003-06-16 2005-12-22 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verfahren zum Konvertieren von fett- oder ölhaltigen Roh- und Abfallstoffen in Gemische mit hohem Kohlenwasserstoffanteil, mit diesem Verfahren hergestellte Produkte und deren Verwendung

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4102938A (en) * 1977-03-02 1978-07-25 Kalur Vijaya Chandra Rao Production of hydrocarbons by thermolysis of vegetable oils
US4992605A (en) 1988-02-16 1991-02-12 Craig Wayne K Production of hydrocarbons with a relatively high cetane rating
CA1313200C (fr) 1988-02-16 1993-01-26 Wayne K. Craig Production d'hydrocarbures a indice de cetane relativement eleve
EP0414384A2 (fr) * 1989-08-08 1991-02-27 Nabisco Brands, Inc. Procédé de préparation de triesters de neoalkyletriols
WO2008066950A2 (fr) * 2006-05-15 2008-06-05 University Of Georgia Research Foundation Carburants diesel multicomposants miscibles et procédés de transformation d'huile bio
WO2008119525A1 (fr) * 2007-04-03 2008-10-09 Lignosol Gmbh & Co. Kg Installation et procédé pour produire des combustibles à partir de matières premières biogènes

Non-Patent Citations (1)

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Title
HUBER GEORGE W ET AL: "Synthesis of transportation fuels from biomass: Chemistry, catalysts, and engineering", CHEMICAL REVIEWS, ACS,WASHINGTON, DC, US, vol. 106, no. 9, 1 September 2006 (2006-09-01), pages 4044 - 4098, XP002490759, ISSN: 0009-2665, [retrieved on 20060627] *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10184085B2 (en) 2014-06-09 2019-01-22 W. R. Grace & Co.-Conn Method for catalytic deoxygenation of natural oils and greases
WO2021230987A1 (fr) 2020-05-13 2021-11-18 Voyager Therapeutics, Inc. Redirection de tropisme de capsides de vaa

Also Published As

Publication number Publication date
SK287982B6 (sk) 2012-08-06
SK500042009A3 (sk) 2010-12-07
DE102008060558A1 (de) 2010-06-10
DE102008060558B4 (de) 2013-09-26

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