WO2014015861A1 - Procédé de liquefaction directe du charbon - Google Patents

Procédé de liquefaction directe du charbon Download PDF

Info

Publication number
WO2014015861A1
WO2014015861A1 PCT/DE2013/100274 DE2013100274W WO2014015861A1 WO 2014015861 A1 WO2014015861 A1 WO 2014015861A1 DE 2013100274 W DE2013100274 W DE 2013100274W WO 2014015861 A1 WO2014015861 A1 WO 2014015861A1
Authority
WO
WIPO (PCT)
Prior art keywords
macromolecular
fossil
hydrogen
oxygen
mixture
Prior art date
Application number
PCT/DE2013/100274
Other languages
German (de)
English (en)
Inventor
Roberto Rinaldi
Nadine BRAUN
Original Assignee
Studiengesellschaft Kohle Mbh
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 Studiengesellschaft Kohle Mbh filed Critical Studiengesellschaft Kohle Mbh
Publication of WO2014015861A1 publication Critical patent/WO2014015861A1/fr

Links

Classifications

    • 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
    • C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/002—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes
    • 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
    • C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/06—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation
    • C10G1/065—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation in the presence of a solvent

Definitions

  • the present invention relates to a process for direct coal liquefaction as well as the generally liquid to viscous reaction mixture obtainable by this process.
  • the organic carbon substance consists for the most part of insoluble three-dimensional, partially crosslinked macromolecular aggregates of aromatic and aliphatic structural units which contain a specific content of heteroatoms (O, N, S) depending on the type of carbon. For liquefaction it therefore requires a comprehensive chemical degradation by bond cleavage to smaller structural units.
  • the production of liquid products (gasoline to heavy oil) from coal is essentially two process routes possible: direct hydrogenation of coal and coal gasification with subsequent (indirect) hydrogenation of the synthesis gas.
  • Coal hydrogenation developed by Friedrich Bergius in 1913, converts the coal with hydrogen to form a coal oil, which can then be further processed to petrol in refineries, similar to crude oil.
  • lignite and geologically young coal can be liquefied directly.
  • the Fischer-Tropsch process describes the preparation of liquid hydrocarbons from the gases carbon monoxide and hydrogen with the aid of metal catalysts.
  • the hydrocarbons synthesized here consist mainly of liquid alkanes (paraffin oils).
  • By-products are olefins, alcohols and solid paraffins (waxes).
  • the Fischer-Tropsch process is applicable to all types of coal as well as other carbonaceous raw materials.
  • a microbial coal liquefaction is described in DE 199 45 975 A1 (Fakoussa RM, Lammerich RM) with the "treatment of lignite constituents for the purpose of finishing".
  • the invention relates to a process for the modification of humic substances from brown coal by changing the solubility and precipitation properties as a result of a microbial or enzymatic decarboxylation.
  • the mechanisms of coal liquefaction by means of enzymes have not been fully explored.
  • microbial coal liquefaction is not a consistent process and strongly dependent on the coal type due to the specificity and substrate specificity of the enzymes involved.
  • WO2002 / 02719 a process for the hydrogenation / hydrogenolysis of hard coal with borane catalysts is disclosed, in which the hard coal and the catalyst are suspended or dispersed in a solvent and then hydrogenated under hydrogen pressure.
  • DE 10 2006 041 870 A1 describes a process in which largely insoluble, highly-charged (low-volatile) hard coal as powdered solids in the presence of molecular (homogeneous) borane and iodine catalysts reacted with hydrogen under pressure to form coal hydrogenation products become.
  • the solid hydrogenation products can then be converted into liquid hydrocarbons in conventional coal liquefaction processes according to Bergius and used in coking processes for the production of blast furnace coke and the production of high-grade coal tar.
  • a hydrocarbon-containing reaction product usually a liquid of a macromolecular fossil Raw material is obtainable by reacting a macromolecular fossil raw material with an ether in the presence of a peroxide compound and a metal salt and the resulting reaction mixture is washed after the reaction with a washing solution.
  • the inventors have attributed the formation of the hydrocarbon-containing liquid to the fact that addition of a radical ether compound to the carbon polymer of the macromolecular fossil raw material results in a liquefied product which can then be subjected to further upgrade procedures. Surprisingly, the macromolecular fossil raw material can be almost completely liquefied in this way.
  • the invention therefore relates to a process for the preparation of a hydrocarbon-containing liquid from a macromolecular fossil raw material, in which reacting a macromolecular fossil raw material with an ether in the presence of a peroxide compound and optionally adding a metal salt and the resulting reaction mixture optionally with after a washing solution is washed.
  • the washing step is necessary in particular if peroxides are still present in the reaction mixture, which complicate work-up.
  • compounds or materials for removing peroxides which then allow the peroxides to react. Examples include Deperox, manganese dioxide, cobalt compounds called.
  • lignite hard coal, charcoal, bitumen, asphalt, tar, peat, xylitol heavy oils, petroleum distillation residues, tar sands or oil shale, especially lignite, peat, xylitol or biomass or mixtures of the aforementioned substances may be used as the macromolecular fossil resource be used.
  • the ethers used may be in particular a straight-chain, branched-chain or cyclic ether having 4 to 10 carbon atoms, preferably 4 to 8 carbon atoms, preferably having one or two tertiary hydrogen atoms - - be used in ⁇ -position to the ether oxygen.
  • the ether may contain one to three oxygen atoms, preferably one or two oxygen atoms. Examples are tetrahydrofuran and ⁇ -alkyl derivatives thereof, such as ⁇ -methyl-THF, ⁇ -methyl-tetrahydropyran, ⁇ -methyl-dioxane, for example as such ethers, which in the presence of oxygen or peroxides form particularly stable ⁇ -radicals.
  • a peroxide compound an inorganic or organic oxygen or peroxide compound or a mixture thereof may be used according to the invention, a reactive oxygen-containing species such as a superoxide radical O2 "-, a hydroxyl radical OH, a peroxide radical OOH , an alkoxy radical RO, a peroxyl alkyl radical ROO form, such as hydrogen peroxide or other peroxyl compounds such as alkyl or dialkyl peroxyl, peroxy-mono or dicarboxylic acids, or oxygen in the presence of a metal salt such as Al (III), or a transition metal cation of a metal of the 3 to 12 group of the periodic table, preferably Co, Ni, Cu, Cr, Fe, Cu, V or Pt.
  • a reactive oxygen-containing species such as a superoxide radical O2 "-, a hydroxyl radical OH, a peroxide radical OOH , an alkoxy radical RO, a peroxyl alkyl radical ROO form, such as hydrogen peroxide or
  • an aluminum salt such as aluminum nitrate, aluminum chloride can be used.
  • Other possible metal salts are the salts of transition metal cations, especially Ni, Co, Cu, Cr or Fe as mentioned above which, with the free radical generator such as hydrogen peroxide, produce the reactive oxygen species as defined above.
  • the free radical generator such as hydrogen peroxide
  • the inventors have used the combination of Al (III) + and hydrogen peroxide and achieved good results.
  • the macromolecular fossil solid is suspended in the ether.
  • 200 to 3000 percent by weight of ethers, based on the macromolecular fossil solid are generally used.
  • 10 to 500 percent by weight of hydrogen peroxide based on the macromolecular fossil solid are generally used.
  • the catalyst is usually used 10 to 200 percent by weight based on the macromolecular fossil solid.
  • the process of the invention can be carried out at atmospheric pressure up to an overpressure of 10 bar and a temperature in the range of 20-120 ° C, especially from 40 to 80 ° C.
  • the reaction product obtained can already be used as a raw material in the petrochemical or chemical industry, the resulting reaction mixture can be subjected to a hydrogen transfer reaction in the presence of a metallic catalyst, generally in a temperature range from 100 ° to 300 ° C., especially 120 ° to 240 ° C, subject to make the product even more versatile.
  • a metallic catalyst generally in a temperature range from 100 ° to 300 ° C., especially 120 ° to 240 ° C, subject to make the product even more versatile.
  • the resulting reaction mixture in the presence of an H donor / donor compound such as a lower secondary aliphatic alcohol selected from 2-propanol, 2-butanol, 2-pentanol, 3-pentanol, sugar alcohols, sugar, cellulose, hemicellulose, lignin or Mixtures thereof, optionally a carboxylic acid such as an aliphatic carboxylic acid having one to twelve carbon atoms, such as Formic acid, and a metallic catalyst are subjected to an H-transfer reaction in which the alcohol or carboxylic acid is oxidized and the resulting reaction mixture is hydrogenated.
  • an H donor / donor compound such as a lower secondary aliphatic alcohol selected from 2-propanol, 2-butanol, 2-pentanol, 3-pentanol, sugar alcohols, sugar, cellulose, hemicellulose, lignin or Mixtures thereof
  • a carboxylic acid such as an aliphatic carboxylic acid having one to twelve carbon atoms, such as Formic acid
  • reaction product is widely used in the petrochemical and chemical industries, and can then be further processed into crude oil in refineries to gasoline. It is of particular advantage that the reaction product obtained is due to the treatment particularly low sulfur and nitrogen available, since the present in the fossil source sulfur and nitrogen compounds are oxidized under the reaction conditions and can be washed out via the wash water.
  • a mixture of 0.5 g of brown coal (Fortuna Garsdorf mining, short analyzes: 5% ash content (anhydrous, wf), 64.4% of volatiles (water and ash free, waf)); ultimate analysis (waf), 67.0% carbon, 5.2% hydrogen, 0.8% nitrogen, 1.4% sulfur and 28.1% oxygen by difference), 0.69 g aluminum nitrate, 2.4 g hydrogen peroxide and 15 mL of 2-methyl-tetrahydrofuran was kept at 70 ° C with stirring for four hours.
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the mixture was refiltered and the solvent removed using a rotary evaporator.
  • the remaining residue was taken up in 3 ml of acetone, the resulting precipitate was removed by centrifuging and the solvent was removed again.
  • the yield of liquid products was 1.0 g.
  • the amount of solid residues was 0.13 g.
  • the short analyzes "Ash” and "Volatile constituents” were based on the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.1% and a content of volatile components (waf) of a total of 98.9%.
  • the ultimate analysis of the liquid product showed (waf) 58.3% carbon, 9.7% hydrogen, 0.2% nitrogen, 0.08% sulfur, and 31.7% oxygen (difference).
  • the mixture was refiltered and the solvent removed using a rotary evaporator.
  • the remaining residue was taken up in 3 ml of acetone, the resulting precipitate was removed by centrifuging and the solvent was removed again.
  • the yield of liquid products was 1.0 g.
  • the amount of solid residues was 0.1 1 g.
  • the short analyzes "Ash” and "Volatile constituents” were made in accordance with the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.01% and a content of volatile components (waf) of a total of 99.9%.
  • the ultimate analysis of the liquid product showed (waf) 57.7% carbon, 7.4% hydrogen, 0.3% nitrogen, 0.09% sulfur and 34.5% oxygen (difference).
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the mixture was refiltered and the solvent removed using a rotary evaporator.
  • the remaining residue was taken up in 3 ml of acetone, the resulting precipitate was removed by centrifuging and the solvent was removed again.
  • the yield of liquid products was 0.91 g.
  • the amount of solid residues was 0.15 g.
  • the short analyzes "Ash” and "Volatile constituents” were carried out in accordance with the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.27% and a content of volatile components (waf) of a total of 98.1%.
  • the ultimate analysis of the liquid product showed (waf) 57.5% carbon, - -
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the mixture was refiltered and the solvent removed using a rotary evaporator.
  • the remaining residue was taken up in 3 ml of acetone, the resulting precipitate was removed by centrifuging and the solvent was removed again.
  • the yield of liquid products was 0.85 g.
  • the amount of solid residues was 0.24 g.
  • the short analyzes "Ash” and "Volatile constituents” were carried out in accordance with the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.07% and a content of volatile components (waf) of a total of 99.2%.
  • the ultimate analysis of the liquid product yielded (waf) 59.3% carbon, 8.3% hydrogen, 0.2% nitrogen, 0.05% sulfur and 32.3% oxygen (difference).
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the yield of liquid products was 0.75 g.
  • the amount of solid residues was 0.46 g.
  • the short analyzes "Ash” and "Volatile constituents” were based on the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0% and a total volatile matter (waf) of 99% ,8th %.
  • the ultimate analysis of the liquid product yielded (waf) 59.3% carbon, 8.4% hydrogen, 0.1% nitrogen, 0.06% sulfur and 32.2% oxygen (difference).
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the mixture was refiltered and the solvent removed using a rotary evaporator.
  • the remaining residue was taken up in 3 ml of acetone, the resulting precipitate was removed by centrifuging and the solvent was removed again.
  • the yield of liquid products was 0.47 g.
  • the amount of solid residues was 0.31 g.
  • the short analyzes "Ash” and "Volatile constituents” were carried out following the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.41% and a content of volatile components (waf) of a total of 99.9%.
  • the ultimate analysis of the liquid product showed (waf) 57.7% carbon, 8.2% hydrogen, 0.2% nitrogen, 0.02% sulfur and 33.9% oxygen (difference).
  • the resulting reaction mixture was filtered, washed twice with 5 mL of distilled water and then refluxed for 1.5 hours with 5 grams of Deperox molecular sieve.
  • the yield of liquid products was 0.15 g.
  • the amount of solid residues was 0.50 g.
  • the short analyzes "Ash” and "Volatile constituents” were based on the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.08% and a content of volatile components (waf) of 100% in total.
  • the ultimate analysis of the liquid product showed (waf) 58.8% carbon, 8.5% hydrogen, 0.3% nitrogen, 0.3% sulfur and 32.5% oxygen (difference).
  • the resulting reaction mixture was filtered, washed twice with 5 ml of distilled water and then refluxed for 1.5 hours with 5 g of Deperox molecular sieve.
  • the mixture was refiltered and the solvent removed using a rotary evaporator.
  • the remaining residue was taken up in 3 ml of acetone, the resulting precipitate was removed by centrifuging and the solvent was removed again.
  • the yield of liquid products is 0.16 g.
  • the amount of solid residue was 0.32 g.
  • the yield of liquid products was 0.16 g.
  • the amount of solid residue was 0.32 g.
  • the short analyzes "Ash” and "Volatile constituents” were based on the methods ASTM D 3174 and ASTM D 3175.
  • the short analyzes of the liquid product gave an ash content (wf) of 0.08% and a content of volatile components (waf) of 100% in total.
  • the ultimate analysis of the liquid product showed (waf) 57.8% carbon, 8.5% hydrogen, 0.3% nitrogen, 0.3% sulfur and 32.5% oxygen (difference).
  • a mixture of 0.5 g of gas-flame coal (Prosper mining, short analyzes: 4.3% ash content (wf), 36.1% of volatiles (waf)); Ultimate Analysis (waf) 79.0% carbon, 4.7% hydrogen, 1.6% nitrogen, 1.9% sulfur and 12.8% oxygen by difference), 0.69 g aluminum nitrate, 2.4 g hydrogen peroxide and 1 5 ml of 2-methyl-tetrahydrofuran was kept at 55 ° C. with stirring for four hours.
  • the yield of liquid products was 0.53 g.
  • the amount of solid residues was 0.96 g.
  • the ultimate analysis of the liquid product showed (waf) 65.2% carbon, 7.3% hydrogen, less than 0.01% sulfur and 27.5% oxygen / nitrogen (difference).
  • a mixture of 0.5 g of charcoal Robott Westerholt-Bergbau, short analyzes: 3.9% ash content (wf), 23.3% of volatiles (waf)); Ultimate analysis (waf) 87.5% carbon, 4.6% hydrogen, 1.6% nitrogen, 1.6% sulfur and 4.6% oxygen by difference), 0.69 g aluminum nitrate, 2.4 g hydrogen peroxide and 1 5 ml of 2-methyl-tetrahydrofuran was kept at 55 ° C. with stirring for four hours.
  • the yield of liquid products was 0.43 g.
  • the amount of solid residues was 1.0 g.
  • the ultimate analysis of the liquid product showed (waf) 61, 4% carbon, 6.5% hydrogen, less than 0.05% sulfur and 32.1% oxygen / nitrogen (difference).
  • a mixture of 0.5 g of charcoal (Niederberg mining, short analyzes: 7.8% ash content (wf), 1 1, 0% of volatiles (waf)); Ultimate analysis (waf) 90.9% carbon, 3.9% hydrogen, 1.7% nitrogen, 0.9% sulfur and 2.5% oxygen by difference), 0.69 g aluminum nitrate, 2.4 g hydrogen peroxide and 1 5 mL of 2-methyl-tetrahydrofuran was kept at 55 ° C with stirring for four hours.
  • the yield of liquid products was 0.46 g.
  • the amount of solid residues was 1, 1 g.
  • the ultimate analysis of the liquid product showed (waf) 65.3% carbon, 7.3% hydrogen, less than 0.01% sulfur and 27.3% oxygen / nitrogen (difference).
  • the yield of liquid products was 0.54 g.
  • the amount of solid residues was 1, 1 g.
  • the ultimate analysis of the liquid product yielded (waf) 66.2% carbon, 7.3% hydrogen, less than 0.01% sulfur and 26.5% oxygen / nitrogen (difference).

Abstract

L'invention concerne un procédé de production d'un liquide contenant des hydrocarbures à partir d'une matière première fossile macromoléculaire, selon lequel on met à réagir une matière première fossile macromoléculaire avec un éther en présence d'un composé peroxyde et d'un sel métallique, le mélange réactionnel obtenu étant ensuite éventuellement lavé dans une solution de lavage. L'invention concerne également le mélange réactionnel ainsi obtenu et son utilisation dans l'industrie pétrochimique.
PCT/DE2013/100274 2012-07-26 2013-07-23 Procédé de liquefaction directe du charbon WO2014015861A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012106811 2012-07-26
DE102012106811.9 2012-07-26

Publications (1)

Publication Number Publication Date
WO2014015861A1 true WO2014015861A1 (fr) 2014-01-30

Family

ID=49212537

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE2013/100274 WO2014015861A1 (fr) 2012-07-26 2013-07-23 Procédé de liquefaction directe du charbon

Country Status (2)

Country Link
DE (1) DE102013107865A1 (fr)
WO (1) WO2014015861A1 (fr)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4085033A (en) * 1976-05-17 1978-04-18 Exxon Research & Engineering Co. Hydrogen donor solvent coal liquefaction process
EP0057577A2 (fr) * 1981-01-29 1982-08-11 The Standard Oil Company Méthode pour l'amélioration, la liquéfaction et la récupération de charbon et d'autres matières carbonées solides, ainsi que les produits améliorés de charbon
DE19945975A1 (de) 1999-09-24 2001-03-29 Rene M Fakoussa Behandlung von Braunkohlebestandteilen zum Zwecke der Veredelung
WO2002002719A1 (fr) 2000-07-04 2002-01-10 Studiengesellschaft Kohle Mbh Hydratation/hydrogenolyse de charbon au moyen de catalyseurs au borane
DE102006041870A1 (de) 2006-09-06 2008-03-27 Studiengesellschaft Kohle Mbh Lösungsmittelfreie Hydrierung / Hydrogenolyse von hochinkohlten Steinkohlen mit Boran- und Iod-Katalysatoren
WO2011021081A1 (fr) 2009-08-19 2011-02-24 IFP Energies Nouvelles Liquéfaction directe du charbon avec hydrotraitement intégré du produit et recyclage en cascade du catalyseur
EP2340295A2 (fr) 2008-10-27 2011-07-06 KiOR, Inc. Procédé de transformation de biomasse
US20110180262A1 (en) * 2008-07-28 2011-07-28 Forbes Oil And Gas Pty. Ltd. Method of liquefaction of carbonaceous material to liquid hydrocarbon
US20110262987A1 (en) * 2010-04-21 2011-10-27 Downey Robert A Solubilization of Carbonaceous Materials and Conversion to Hydrocarbons and Other Useful Products
US20120175114A1 (en) * 2010-12-22 2012-07-12 Chevron U.S.A. Inc. In-situ kerogen conversion and product isolation

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4085033A (en) * 1976-05-17 1978-04-18 Exxon Research & Engineering Co. Hydrogen donor solvent coal liquefaction process
EP0057577A2 (fr) * 1981-01-29 1982-08-11 The Standard Oil Company Méthode pour l'amélioration, la liquéfaction et la récupération de charbon et d'autres matières carbonées solides, ainsi que les produits améliorés de charbon
DE19945975A1 (de) 1999-09-24 2001-03-29 Rene M Fakoussa Behandlung von Braunkohlebestandteilen zum Zwecke der Veredelung
WO2002002719A1 (fr) 2000-07-04 2002-01-10 Studiengesellschaft Kohle Mbh Hydratation/hydrogenolyse de charbon au moyen de catalyseurs au borane
DE102006041870A1 (de) 2006-09-06 2008-03-27 Studiengesellschaft Kohle Mbh Lösungsmittelfreie Hydrierung / Hydrogenolyse von hochinkohlten Steinkohlen mit Boran- und Iod-Katalysatoren
US20110180262A1 (en) * 2008-07-28 2011-07-28 Forbes Oil And Gas Pty. Ltd. Method of liquefaction of carbonaceous material to liquid hydrocarbon
EP2340295A2 (fr) 2008-10-27 2011-07-06 KiOR, Inc. Procédé de transformation de biomasse
WO2011021081A1 (fr) 2009-08-19 2011-02-24 IFP Energies Nouvelles Liquéfaction directe du charbon avec hydrotraitement intégré du produit et recyclage en cascade du catalyseur
US20110262987A1 (en) * 2010-04-21 2011-10-27 Downey Robert A Solubilization of Carbonaceous Materials and Conversion to Hydrocarbons and Other Useful Products
US20120175114A1 (en) * 2010-12-22 2012-07-12 Chevron U.S.A. Inc. In-situ kerogen conversion and product isolation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
D. G. B. BOOCOCK ET AL: "Wood liquefaction: Extended batch reactions using raney nickel catalyst", THE CANADIAN JOURNAL OF CHEMICAL ENGINEERING, vol. 60, no. 6, 1 October 1982 (1982-10-01), pages 802 - 808, XP055086633, ISSN: 0008-4034, DOI: 10.1002/cjce.5450600612 *
JENS RUDAT, ENZYMATISCHE DECARBOXYLIERUNG VON BENZENPOLYCARBONSÄUREN, 2006, pages 129,169, Retrieved from the Internet <URL:urn:nbn:de:hbz:5N- 08738>

Also Published As

Publication number Publication date
DE102013107865A1 (de) 2014-01-30

Similar Documents

Publication Publication Date Title
US4125455A (en) Hydrotreating heavy residual oils
EP2550344B1 (fr) Procédé pour la conversion de lignine en hydrocarbures liquides
Given et al. Dependence of coal liquefaction behaviour on coal characteristics. 1. Vitrinite-rich samples
US4298454A (en) Hydroconversion of an oil-coal mixture
JPS6215599B2 (fr)
US20120152801A1 (en) Biofuel compositions and methods based on co-processing aromatic-rich and aromatic-lean components
CN111566190A (zh) 一种获得稳定的木质素的方法：通过温和溶剂改性得到极性有机溶剂组合物
AU2011251966A1 (en) Process for liquefying a cellulosic material
DE2739078A1 (de) Verfahren zur umwandlung von kohlenwasserstoffen
Li et al. Hydro-liquefaction of rice stalk in supercritical ethanol with in situ generated hydrogen
US2119647A (en) Production of valuable hydrocarbons
US4121995A (en) Surfactant-assisted liquefaction of particulate carbonaceous substances
US4762529A (en) Novel fuel for use in energy generating processes
US4427526A (en) Process for the production of hydrogenated aromatic compounds and their use
WO2014015861A1 (fr) Procédé de liquefaction directe du charbon
DE977520C (de) Verfahren zur kontinuierlichen spaltenden Hydrierung von schwer hydrierbaren hartasphaltreichen Kohlenwasserstoffoelen
US4313821A (en) Processing of coal liquefaction products
DE3107712C2 (de) Verwendung eines vorwiegend auf kohlestämmiger Basis hergestellten Kohleöls als Brennstoff
Luik et al. Parallels between slow pyrolysis of Estonian oil shale and forest biomass residues
EP3575383A1 (fr) Procédé catalytique à solvant biphasique pour la production de molécules mono-oxygénées à partir d&#39;une matière première biologique comprenant des hydrates de carbone
DE580828C (de) Verfahren zur UEberfuehrung von Kohlearten, Teeren, Mineraloelen u. dgl., in insbesondere niedrigsiedende Brennstoffe von der Art der Benzine, Mitteloele, Leuchtoele usw.
Polyakov Conversion of Low-Rank Wyoming Coals into Gasoline by Direct Liquefaction
EP3575384A1 (fr) Procédé catalytique de solvants à deux phases pour la production de molécules mono-oxygénées à partir de matières premières biologiques comprenant des glucides et utilisation desdites molécules mono-oxygénées dans un processus de craquage catalytique fluide
US4760803A (en) Process for generating energy in a furnace or combustion engine
Tymchyshyn Hydrotreatment of lignin into green fuels and chemicals

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13763179

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 1120130036835

Country of ref document: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13763179

Country of ref document: EP

Kind code of ref document: A1