WO2015123714A1 - Procédé de liquéfaction d'une matière carbonée - Google Patents

Procédé de liquéfaction d'une matière carbonée Download PDF

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Publication number
WO2015123714A1
WO2015123714A1 PCT/AT2015/050050 AT2015050050W WO2015123714A1 WO 2015123714 A1 WO2015123714 A1 WO 2015123714A1 AT 2015050050 W AT2015050050 W AT 2015050050W WO 2015123714 A1 WO2015123714 A1 WO 2015123714A1
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Prior art keywords
catalyst
mixture
feo
carbonaceous material
hydrogen donor
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Ceased
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PCT/AT2015/050050
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German (de)
English (en)
Inventor
Nikolaus Schwaiger
Roland FEINER
Hannes PUCHER
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Technische Universitaet Graz
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Technische Universitaet Graz
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Publication of WO2015123714A1 publication Critical patent/WO2015123714A1/fr
Anticipated expiration legal-status Critical
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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
    • C10G1/06—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
    • 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
    • C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
    • 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
    • C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
    • C10G1/086—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
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/42—Hydrogen of special source or of special composition

Definitions

  • the present invention relates to a process for liquefying a carbonaceous material.
  • the liquefaction of carbonaceous materials has a long tradition and has been used on an industrial scale for over 100 years.
  • the carbon compounds present in these materials are hydrogenated at high temperatures and pressures, and ideally with the aid of a catalyst, forming gaseous and liquid hydrocarbons.
  • These can be obtained similarly as from liquid petroleum fractions and e.g. be used as fuels and fuels. In the course of liquefaction also heavy residues arise.
  • DE 3611340 relates to a process in which lignin and cellulosic biomass / oil slurry is treated with a metallic catalyst and hydrogenated at a temperature of 300 to 400 ° C and a hydrogen partial pressure of 35 to 250 bar.
  • the starting material used in this process is slurried in an oil prior to the process. In this process, no hydrogen donor is used.
  • Sugimoto Y et al. (Sekitan Kagaku Kaigi Happyo Ronbunshu 31 (1994): 60-62) describe a process with the pyrolysis residues be hydrogenated from cellulosic starting materials at 350 ° C in the presence of tetralin and a catalyst.
  • CN 1376766 relates to a process for the hydrogenation of pyrolysis oil, in which the oil is treated with a catalyst and a hydrogen donor and hydrogenated at a hydrogen pressure of 20 to 150 bar and a temperature of 340 to 550 ° C for 10 to 240 minutes ,
  • the object of the present invention is to provide a process for the liquefaction of carbonaceous organic materials which overcomes the disadvantages of the prior art and also makes it possible to liquefy oxygen-rich materials.
  • the present invention relates to a process for liquefying a carbonaceous material which is a product or intermediate from a wood pulping process, which preferably comprises a carbon content of less than 60% by weight, based on atro material, comprising
  • step b) heating the mixture from step a) to a temperature in the range of 300 ° C to 600 ° C at a total pressure of 10 to 800 bar over a period of 5 minutes to 12 hours.
  • the process according to the invention is particularly suitable for liquefying carbon in products or intermediates from wood pulping processes.
  • the entire liquefaction process can be carried out in conventional plants and reactors, which are also suitable for the liquefaction of coal.
  • the process according to the invention is preferably carried out in the presence of hydrogen, which is preferably introduced into the reactor before the hydrogenation.
  • the reactor is pressurized, preferably using hydrogen.
  • the carbonaceous material is added to the hydrogenation (step b)) with a hydrogen donor.
  • Hydrogen for example, provided by the donor reduces the compounds present in the material and is therefore important to the entire process. In order to optimize the liquefaction of the material, this is additionally mixed with a catalyst.
  • non-fossil material having a carbon content of less than 60% by weight includes all carbonaceous materials which are not of fossil origin such as lignite, coal or coal Such materials are preferably of vegetable origin and preferably comprise wood or parts thereof This term also covers products and intermediates from wood digestion processes.
  • Carbon-containing materials also include “non-fossil materials having a carbon content of less than 60% by weight” in connection with the present invention.
  • wood pulping wood is mechanically and / or chemically digested to recover cellulose.
  • the lignin matrix of the wood is dissolved or broken up and the lignin-embedded cellulose is exposed accordingly.
  • mechanical wood pulping processes the wood can be pressed against a rotating grindstone.
  • woodchips can be defibered under heat and pressure between two rotating discs of a refiner.
  • Chemical pulping processes include the sulphate, sulphite and soda processes, with cellulose being used for papermaking primarily by the sulphate process.
  • Other wood pulping processes include the Organocell, ASAM, Formacell, Milox and Organosolv methods.
  • Carbonaceous material that is a product or intermediate of a wood pulping process also includes dried or partially dried products or intermediates from a pulping process.
  • the carbon content in the material used in the invention is preferably at least 5 wt%, more preferably at least 10 wt%, even more preferably at least 15 wt%, even more preferably at least 20 wt%, based on atro material.
  • Atro means “absolutely dry”.
  • Atro refers to a material which has been dried for 24 hours at 105 ° C.
  • “Based on atro material” thus means that a value or measured value refers to “absolutely dry material”.
  • the process of the invention is particularly well suited for liquefying carbonaceous materials which have a relatively high inorganic content (e.g., salts and oxides expressed as ash content).
  • the carbonaceous material that can be liquefied by the process of the present invention has an ash content of from 2% to 40%, preferably from 3% to 35%, more preferably from 5 to 30%, even more preferably from From 5 to 25%, more preferably from 10 to 25%, even more preferably from 10 to 20%, based on atro material.
  • Ash content is determined by the carbonaceous material at a temperature in the range between 400 ° C and
  • 600 ° C preferably to a temperature of 500 ° C or 550 ° C, is heated. The temperature is maintained until no weight loss is observed. During this process all organic material burns out and inorganic material (especially salts and oxides) remain in the incineration residue.
  • At least one hydrogen donor is added to the carbonaceous material.
  • the amount of the at least one hydrogen donor in the mixture is from 1 wt% to 1000 wt%, preferably from 2 wt% to 800 wt%, more preferably from 5 wt% to 600 wt%. -%, more preferably from 10 wt .-% to 500 wt .-%, based on the total mixture.
  • Step b) of the process of the present invention is carried out at a temperature in the range of 300 ° C to 600 ° C.
  • this step takes place at a temperature in the range of 350 ° C to 550 ° C, preferably from 400 ° C to 500 ° C, instead.
  • the total pressure at which the hydrogenation of the carbon-containing compounds is carried out is 10 to 800 bar, preferably 20 to 700 bar, preferably 30 to 600 bar, preferably 40 to 500 bar, preferably 50 to 500 bar, preferably 50 to 400 bar, preferably 60 to 350 bar, preferably 70 to 350 bar, preferably 80 to 300 bar, preferably 80 to 280 bar, preferably 80 to 250 bar, preferably 80 to 200 bar.
  • the pressure during the hydrogenation should be at least 10 bar, preferably at least 20 bar, even more preferably at least 50 bar.
  • the duration of hydrogenation of the carbonaceous material is 5 minutes to 12 hours, preferably 10 minutes to 10 hours, more preferably 15 minutes to 8 hours, even more preferably 20 minutes to 7 hours, even more preferably 30 minutes to 6 hours.
  • the at least one catalyst is selected from the group consisting of ferric ion hydroxide (FeO (OH)), cobalt molybdenum sulfide, Fe2O3, red mud, and combinations thereof.
  • FeO ferric ion hydroxide
  • cobalt molybdenum sulfide Fe2O3, red mud, and combinations thereof.
  • the catalyst used in the process may preferably have any shape, and it is particularly preferred to add particulate form catalysts (e.g., rod-shaped, circular) to the mixture.
  • the size (length or diameter) of the particles is preferably 10 nm to 1 mm, preferably 10 nm to 500 pm, preferably 10 nm to 200 pm, preferably 10 nm to 100 pm, preferably 10 nm to 50 pm, preferably 10 nm to 10 pm, preferably 10 nm to 5 pm, preferably 10 nm to 1 pm , preferably 10 nm to 500 nm, preferably 20 nm to 1 mm, preferably 20 nm to
  • 500pm preferably 20nm to 200pm, preferably 20nm to 100pm, preferably 20nm to 50pm, preferably 20nm to 10pm, preferably 20nm to 5pm, preferably 20nm to lpm, preferably 20nm to 500nm, preferably 30nm to 1mm, preferably 30nm to
  • 500pm preferably 30nm to 200pm, preferably 30nm to 100pm, preferably 30nm to 50pm, preferably 30nm to 10pm, preferably 30nm to 5pm, preferably 30nm to lpm, preferably 30nm to 500nm.
  • iron (I I) -oxidhydroxid (FeO (OH)) catalysts It is particularly preferred to use iron (I I) -oxidhydroxid (FeO (OH)) catalysts.
  • the iron (III) oxide hydroxide is catalyst ⁇ - FeO (OH) (gamma-FeO (OH)), -FeO (OH) (alpha-FeO (OH)), or a combination thereof.
  • Y-FeO (OH) gamma-FeO (OH)
  • OH gamma-FeO
  • the catalyst in the mixture is preferably in an amount of from 0.1 to 20% by weight, preferably from 0.5 to 17% by weight, more preferably from 1 to 15% by weight, based on the total mixture, contain.
  • a catalyst is used in the process according to the invention.
  • This catalyst is added in the aforementioned amount to the mixture comprising carbonaceous material and hydrogen donor.
  • the catalyst in the mixture in an amount of preferably 0.1 31S 19 wt. - o,
  • 0 preferably 0.1 to 10 wt. o, preferably 0.1 to 5 wt. - o,
  • 0 preferably 0.5 to 19 wt. o, preferably 0.5 to 18 wt. - o,
  • 0 preferably 0.5 to 16 wt. o, preferably 0.5 to 15 wt. - o,
  • 0 preferably 0.5 to 14 wt. o, preferably 0.5 to 13 wt. - o,
  • 0 preferably 0.5 to 12 wt. o, preferably 0.5 to 11 wt. - o, preferably o,
  • 0 preferably 0.5 to 2 wt. -o, preferably 1 to 20 wt .-%, preferably 1 to 19 wt .-%, preferably 1 to 18 wt .-%, preferably 1 to 16 wt .-%, preferably 1 to 14 wt .-%, preferably 1 to 13 wt.%, preferably 1 to 12 wt.%, preferably 1 to 11 wt.%, preferably 1 to 10 wt.%, preferably 1 to 5 wt.%, preferably 1 to 2 wt.
  • % preferably 2 to 20 wt .-%, preferably 2 to 19 wt .-%, preferably 2 to 18 wt .-%, preferably 2 to 17 wt .-%, preferably 2 to 16 wt .-%, preferably 2 to 15 wt .-%, preferably 2 to 14 wt .-%, preferably 2 to 13 wt .-%, preferably 2 to 12 wt .-%, preferably 2 to 11 wt .-%, preferably 2 to 10 wt .-% , preferably 5 to 20 wt .-%, preferably 5 to 19 wt .-%, preferably 5 to 18 wt .-%, preferably 5 to 17 wt .-%, preferably 5 to 16 wt .-%, preferably 5 to 15 Wt .-%, preferably 5 to 14 wt .-%, preferably 5 to 13 wt .-%, preferably 5 to 12
  • the carbonaceous material is additionally mixed with sulfur or H2S.
  • sulfur or H 2 S is preferably present in an amount of from 0.1 to 20% by weight, preferably from 0.5 to 15% by weight, based on the total mixture.
  • the above amount refers to the elemental sulfur occurring in the compound.
  • the mixture according to the invention comprising the carbonaceous material, the hydrogen donor and the catalyst
  • Sulfur or H2S in an amount of preferably 0.1 to 20 wt .-%, preferably from 0.1 to 18 wt .-%, preferably from 0.1 to 15 wt .-%, preferably from 0.1 to 12 wt .-%, preferably from 0.1 to 10 wt .-%, preferably from 0.1 to 5 wt .-%, preferably from 0.5 to 12 wt .-%, preferably from 0.5 to 10 parts by weight. %, preferably from 0.5 to 5 wt .-%, based on the total mixture.
  • Non-fossil carbonaceous materials can be liquefied with the process of the invention.
  • the carbonaceous material is preferably selected from the group consisting of a by-product of alkaline cellulose production, acid cellulose production, the Organosolv process, the steam explosion process, and combinations thereof.
  • carbonaceous intermediates, waste products or end products which comprise less than 60% by weight of carbon, based on the atro material accumulate and accumulate suitable for liquefaction.
  • carbonaceous products or materials can be used in the process according to the invention.
  • Particularly preferred lignin and / or hemi-cellulose-containing materials are liquefied by the process according to the invention, which are obtained in the production of cellulose.
  • Such methods are i.a. the sulphate process or the
  • Kraft pulping alkaline cellulose production
  • sulfite process acid cellulose production
  • Organosolv process as well as the organocell process, the Asam process, the Formacell process and the Milox Processes
  • Carbon and especially lignin-containing materials derived from the sulphate process are particularly preferred.
  • the by-product of the cellulose production in particular the alkaline cellulose production, which is used in the process according to the invention, black liquor.
  • Black liquor is an energy and lignin-rich by-product of cellulose production and, after pulp separation, contains residual lignin, hemicellulose, water and chemicals used in wood pulping.
  • Black liquor usually has a solids content of 14-18%, with about 60 to 70% of the solids content being organic wood components.
  • black liquor has a relatively high inorganic content (expressed as ash content, see above).
  • the ash content in the black liquor is from 2% to 40%, preferably from 3% to 35%, more preferably from 5 to 30%, even more preferably from 5 to 25%, even more preferably from 10 to 25%, even more preferably from 10 to 20 %, based on atro material.
  • thermal methods are used to determine the ash content (e.g., calcination of the material at 550 ° C in accordance with DIN 51719).
  • the water content of the black liquor is preferably reduced before or during mixing with the at least one hydrogen donor and with at least one catalyst.
  • the water content may be at least 10%, preferably at least 20%, preferably at least 30%, preferably at least 40%, preferably at least 50%, preferably at least 60%, preferably at least 70%, preferably at least 80%, preferably at least 90%, preferably at least 95%, be reduced.
  • the black liquor after reduction of the water content is at most 90%, preferably at most 80%, even more preferably at most 70%, even more preferably at most 60%, even more preferably at most 50%, even more preferably at most 40%, even more preferably at most 30%, more preferably at most 20%, even more preferably at most 10%, even more preferably at most 5%, of water in comparison to the solids weight of the dried black liquor.
  • the solids weight can be determined, for example, by drying the black liquor at 105 ° C. over a period of up to 24 hours.
  • Methods for reducing the water content in black liquor are known in the art and preferably include thermal methods (eg evaporation plants, distillation, vacuum distillation).
  • the at least one hydrogen donor is selected from the group consisting of 1, 2, 3, 4-tetrahydronaphthalene (tetra-lin), formic acid, salts of formic acid, 4, 5-dihydropyrene, 9, 1 O- Dihydrophenanthrene and combinations thereof.
  • tetralin 1,2,3,4-tetrahydronaphthalene
  • naphthalene is recovered from the mixture and rehydrated to 1,2,3,4-tetrahydronaphthalene (tetralin).
  • a high inorganic content (including salts and ashes) of a carbonaceous starting material such as e.g. the black liquor
  • a carbonaceous starting material such as e.g. the black liquor
  • tetralin is added to the carbonaceous material as hydrogen donor and Y-FeO (OH) (gamma-FeO (OH)) as catalyst.
  • OH gamma-FeO
  • sulfur, H 2 S or another sulfur source is particularly preferred.
  • Another aspect of the present invention relates to a composition obtainable by the process according to the invention.
  • Example 1 shows the molecular size distribution of liquefied kraft lignin according to Example 1.
  • FIG. 2 shows the molecular size distribution of liquefied kraft lignin according to Example 2.
  • Figures 1 and 2 show that larger pieces of the carbonaceous material can be liquefied by the liquefaction method according to the invention ( Figure 1, Example 1) and not - as in the alternative variant without Catalyst ( Figure 2, Example 2) - char.
  • Fig. 3 shows the influence of the catalyst on the liquefaction rates of a carbonaceous material according to the invention from a pulping process.
  • Red mud (“red mud”) and gamma-FeOOH (“g-FeOOH”) were used as catalyst.
  • g-FeOOH gamma-FeOOH
  • the reactor was cooled and weighed, and the gas formed was vented, thereby determining the amount of gas formed Thereafter, the solids were separated by filtration and the content thereof was determined, and the liquid-wetted residue was extracted to determine the absolute solid content, and the carbon content of the solid after hydrogenation was 10% (before hydrogenation 35.39%). Thus, 78% of the carbon was liquefied and hydrogenated into the hydrocarbon fraction.
  • the mixtures were transferred to a stainless steel autoclave which was closed and charged with 50 bar of hydrogen. After reaching the target temperature of 425 ° C was hydrogenated with continuous hydrogen flow at 180 bar for 30 min. After 30 minutes, the reactor was cooled and the gas formed was vented. Thereafter, the solids were separated by filtration and its content determined. The liquid-wetted residue was extracted, whereby the absolute solids content could be determined. The liquefaction rate of the individual test series was finally determined by comparing the weight of starting material and the weight of the solid at the end of the reaction.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

L'invention concerne un procédé de liquéfaction d'une matière carbonée qui est un produit ou un produit intermédiaire d'une opération de délignification du bois. Ledit procédé comprend les étapes suivantes : a) le mélange de la matière carbonée avec au moins un donneur d'hydrogène et avec au moins un catalyseur ; et b) le chauffage du mélange provenant de l'étape a) à une température située dans la plage allant de 300°C à 600°C à une pression totale allant de 10 à 800 bar pendant une durée allant de 5 minutes à 12 heures.
PCT/AT2015/050050 2014-02-24 2015-02-24 Procédé de liquéfaction d'une matière carbonée Ceased WO2015123714A1 (fr)

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ATA50139/2014A AT515486B1 (de) 2014-02-24 2014-02-24 Verfahren
ATA50139/2014 2014-02-24

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4409089A (en) * 1980-08-14 1983-10-11 Mobil Oil Corporation Coal liquefaction and resid processing with lignin
US4534848A (en) * 1983-01-26 1985-08-13 Hokkaido University Coal liquefaction with a selenium catalyst
DE3611340A1 (de) 1986-04-04 1987-10-08 Faix Oskar Dipl Holzw Dr Verfahren zur erzeugung von niedrigviskosen, niedermolekularen, hexanloeslichen leicht- und mitteloelen durch katalytische druckhydrierung von lignocellulosischer biomasse
CN1376766A (zh) 2002-03-29 2002-10-30 华东理工大学 生物质快速裂解油的加氢处理方法
US20110167713A1 (en) * 2010-01-12 2011-07-14 IFP Energies Nouvelles Process for direct hydorliquefaction of biomass comprising two stages of ebullating bed hydroconversion

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4409089A (en) * 1980-08-14 1983-10-11 Mobil Oil Corporation Coal liquefaction and resid processing with lignin
US4534848A (en) * 1983-01-26 1985-08-13 Hokkaido University Coal liquefaction with a selenium catalyst
DE3611340A1 (de) 1986-04-04 1987-10-08 Faix Oskar Dipl Holzw Dr Verfahren zur erzeugung von niedrigviskosen, niedermolekularen, hexanloeslichen leicht- und mitteloelen durch katalytische druckhydrierung von lignocellulosischer biomasse
CN1376766A (zh) 2002-03-29 2002-10-30 华东理工大学 生物质快速裂解油的加氢处理方法
US20110167713A1 (en) * 2010-01-12 2011-07-14 IFP Energies Nouvelles Process for direct hydorliquefaction of biomass comprising two stages of ebullating bed hydroconversion

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BERL ET AL., IND ENG CHEM, vol. 33, 1941, pages 672 - 674
DOUGLAS C ELLIOTT ET AL: "Catalytic hydrotreating of black liquor oils", ENERGY & FUELS, VOL. 5, 1 January 1991 (1991-01-01), pages 102 - 109, XP055188061, Retrieved from the Internet <URL:http://pubs.acs.org/doi/pdf/10.1021/ef00025a018> [retrieved on 20150507], DOI: 10.1021/ef00025a018 *
SUGIMOTO Y ET AL., SEKITAN KAGAKU KAIGI HAPPYO RONBUNSHU, vol. 31, 1994, pages 60 - 62

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AT515486B1 (de) 2017-05-15

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