EP0718392B1 - Verfahren zur Aufarbeitung von Pyrolyseölen zur Anwendung als Brennstoffe und als Ausgangsprodukt für chemische Produkte durch Reaktion mit Alkoholen - Google Patents
Verfahren zur Aufarbeitung von Pyrolyseölen zur Anwendung als Brennstoffe und als Ausgangsprodukt für chemische Produkte durch Reaktion mit Alkoholen Download PDFInfo
- Publication number
- EP0718392B1 EP0718392B1 EP95309400A EP95309400A EP0718392B1 EP 0718392 B1 EP0718392 B1 EP 0718392B1 EP 95309400 A EP95309400 A EP 95309400A EP 95309400 A EP95309400 A EP 95309400A EP 0718392 B1 EP0718392 B1 EP 0718392B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pyrolysis
- alcohol
- ethanol
- liquid products
- steps
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
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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
- C10G1/002—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
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C5/00—Production of pyroligneous acid distillation of wood, dry distillation of organic waste
Definitions
- This invention relates to a method of upgrading liquid products freshly obtained from the pyrolysis of biomass to chemically and thermally stabilize said products.
- a method is provided for modifying the liquid products from the pyrolysis of biomass by removing water therefrom and for converting aldehydic, ketonic and carboxylic compounds present therein to acetals, ketals and esters, respectively.
- the said liquid product is referred to variously as the pyrolysate, pyrolytic oil or pyrolytic tar.
- An object of this invention is to provide an economical method for improving the liquid products from the pyrolysis of lignocellulosic materials and other biomass for the purposes of their use as liquid fuels in boilers, turbines and internal combustion engines.
- Another object of this invention is to provide a method for reducing the corrosivity of the said biomass pyrolysis oils to minimize problems with their storage and handling.
- Yet another object of this invention is to provide a method for enhancing the chemical and thermal stability of the said pyrolysis oils so as to prevent aging and thus to avoid the consequent problems of viscosity increases with time and deposition in fuel lines.
- a further object of this invention is to provide a method for enhancing the specific heating value of the said pyrolysis oils by chemical combination of these oils with a suitable alcohol and further by reducing the water content of the oils.
- a method of upgrading liquid products freshly obtained from the pyrolysis of biomass to chemically and thermally stabilize said products comprising:
- Figure 1 is a graph comparing the overall material balance initially after the ethanol is added and after the completion of the reaction.
- the viscosity of the said pyrolysis oils are substantially reduced which facilitates the pumping and atomization of these oils in combustion apparatus and improves their filterability which could be relevant for removing cation contaminants.
- This invention is based on the discovery that, under appropriate conditions, pyrolysis oils obtained in the manner described will chemically combine with substantial quantities of various alcohols and that compared with the original pyrolysis oil, this modified product is of lower acidity, contains reduced amounts of aldehydic groups, is of lower viscosity, contains less water and has a higher specific heating value. These enhancements are expected to minimize most of the problems associated with the use of these oils as fuels.
- the alcohol combined is ethanol.
- a hardwood pyrolysis oil was mixed at room temperature with an excess of ethanol, a small quantity of a mineral acid and a suitable dehydrating agent (for example, Molecular Sieve 3A), astonishingly up to 40 wt% of the alcohol on the basis of the organic fraction of the oil became chemically combined with the oil.
- the resulting mixture had the desirable properties previously outlined.
- Molecular Sieve 3A was used as a desiccant to remove water of reaction and thereby to drive any reversible reactions to completion.
- This sieve has a sufficiently small pore size that only water should be absorbed within the pores though adsorption of organic species may be expected to occur on the external surfaces.
- Fifteen grams of the activated molecular sieve were added to 40.6 g of the solution and the mixture was allowed to stand at room temperature. Within a few minutes, ester and acetal peaks began to appear in the gas chromatographic trace of the solution. After two hours, the solution was again analyzed quantitatively. In addition, the ethanol content was determined to be 35.9 wt% and the water content was 0.28 wt%.
- the hardwood pyrolysis tars typically contain 52 wt% carbon and 6 wt% hydrogen on a moisture-free basis so the initial heating value is estimated to be 25.7 MJ/kg.
- the calorific value of the tar after chemical combination with ethanol by making use of the same assumptions made in calculating the mass balance. The result is that the final elemental composition on an ethanol and water-free basis is 57 wt% carbon and 7.7 wt% hydrogen giving an estimated calorific value of 29.7 MJ/kg, an increase of about 16%.
- Example 1 The extent of chemical combination of methanol with the organic fraction of the pyrolysate can be estimated using the calculational scheme outlined in Example 1. The result is that the uptake was only 0.0533 kg of methanol/kg of organic material originally present in the pyrolysis tar. This is much less than that obtained with ethanol in Example 1.
- Example 3 a mixture of two alcohols was tested.
- the hardwood pyrolysate used in Example 3 was dissolved in a mixture of methanol and n-propanol so that the initial concentrations of the alcohols were 18.72 and 28.01 wt% respectively.
- the initial water content of this mixture was 4.31 wt% and the mass fraction of organics from the pyrolytic tar amounted to 48.96 wt% of it.
- To this solution was added 3.34 wt% sulfuric acid as catalyst and the whole mixture placed over an amount of Molecular Sieve 3A equivalent to 80 wt% of it.
- Example 1 After five hours on standing at room temperature, the mixture was analyzed and found to contain 12.32 wt% and 17.76 wt% of methanol and n-propanol respectively. The final water concentration was small (less than 0.2 wt%).
- a pyrolytic tar obtained by flash pyrolysis of Eucalyptus wood.
- This tar contained a high proportion of pyrolytic lignin (36.4 wt% of the organic fraction of the liquid) with a correspondingly low concentration of low molecular weight carbonyl compounds.
- hydroxyacetaldehyde was only 7.1 wt% of the organic fraction of the tar.
- hydrochloric acid was used as an alternative catalyst for the reaction.
- esters of acetic and formic acids are known commercial chemicals, while the acetals of hydroxyacetaldehyde and glyoxal may have value as solvents, fuel additives or as flavour chemicals.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Processing Of Solid Wastes (AREA)
- Fats And Perfumes (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Claims (16)
- Verfahren zumAufarbeiten von flüssigen Produkten, die aus der Pyrolyse von Biomasse erhalten werden, zur Verwendung als zumindest ein Stoff für chemische Ausgangsstoffe und als Brennstoff, wobei das Verfahren umfaßt:(a) das Zusetzen eines Alkohols zu den flüssigen Produkten, die aus einem Pyrolyseverfahren erhalten werden;(b) das chemische Reagieren des Alkohols mit den flüssigen Produkten unter Verwendung eines sauren Katalysators;(c) das Entfernen von Wasser, wodurch die Reaktion zum Abschluß gebracht wird.
- Verfahren nach Anspruch 1, wobei es den Schritt des Zusetzens von Alkohol in einer Menge umfaßt, die aus der Gruppe ausgewählt ist, die stöchiometrisch, unterstöchiometrisch und überschüssig zusammengesetzt ist.
- Verfahren nach Anspruch 1 oder 2, wobei das Verfahren unter Verwendung von Ethanol als Alkohol ausgeführt wird.
- Verfahren nach Anspruch 1, wobei das Verfahren die Schritte des Zusetzens eines Überschusses an Ethanol, einer kleinen Menge Mineralsäure als Katalysator und eines geeigneten Dehydrationsmittels zu den flüssigen Produkten der Pyrolyse umfaßt.
- Verfahren nach Anspruch 4, wobei das Dehydrationsmittel ein Molekularsieb ist, das zur Abtrennung von Wasser aus den flüssigen Produkten verwendet wird.
- Verfahren nach Anspruch 5, wobei es den Schritt des Verwendens des Molekularsiebes 3A als Molekularsieb umfaßt.
- Verfahren nach einem der Ansprüche 4, 5 oder 6, wobei die Mineralsäure Schwefelsäure ist.
- Verfahren nach einem der Ansprüche 1, 2 oder 3, wobei es den Schritt der Umwandlung jeglicher vorhandener Aldehyd-, Keton- und Carbonsäureverbindungen entsprechend zu Acetalen, Ketalen und Ester umfaßt.
- Verfahren nach einem der Ansprüche 1, 2 oder 3, wobei es den Schritt der kontinuierlichen Ausführung des Verfahrens umfaßt.
- Verfahren nach einem der Ansprüche 1, 2 oder 3, wobei es den Schritt der kontinuierlichen Ausführung des Verfahren durch Pumpen einer Mischung der flüssigen Produkte und Alkohol durch eine Säule mit einem Molekularsieb umfaßt.
- Verfahren nach einem der Ansprüche 1, 2 oder 3, wobei es die Schritte umfaßt, die flüssigen Produkte mit ausreichend Ethanol zu mischen, um eine geringe Anfangskonzentration mit Wasser sicherzustellen, das überschüssige Ethanol abzudestillieren und das Ethanol anschließend zu trocknen.
- Verfahren nach einem der Ansprüche 1, 2 oder 3, wobei es den Schritt des kontinuierlichen Entfernens von Wasser während der Reaktion durch azeotrope Destillation mit einem nicht mischbaren Lösemittel umfaßt.
- Verfahren nach einem der Ansprüche 3, 4 oder 5, wobei es die Schritte des Entfernens der Mineralsäure aus der letztlich vorliegenden Mischung durch Zugeben von Kalk und des Abfiltrierens des ausgefallenen Kalziumsalzes umfaßt.
- Verfahren nach einem der Ansprüche 1, 2 oder 3, wobei es den Schritt des Verwendens eines festen sauren Katalysators als Mineralsäure umfaßt.
- Brennstoff, der durch chemische Reaktion von Pyrolyseöl und Alkohol erhalten wird.
- Chemischer Ausgangsstoff, der durch chemische Reaktion von Pyrolyseöl und Alkohol erhalten wird.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9426066 | 1994-12-22 | ||
GBGB9426066.8A GB9426066D0 (en) | 1994-12-22 | 1994-12-22 | Method of upgrading biomass pyrolysis liquids for use as fuels and as a source of chemicals by reaction with alcohols |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0718392A1 EP0718392A1 (de) | 1996-06-26 |
EP0718392B1 true EP0718392B1 (de) | 1999-09-01 |
Family
ID=10766483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95309400A Expired - Lifetime EP0718392B1 (de) | 1994-12-22 | 1995-12-22 | Verfahren zur Aufarbeitung von Pyrolyseölen zur Anwendung als Brennstoffe und als Ausgangsprodukt für chemische Produkte durch Reaktion mit Alkoholen |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0718392B1 (de) |
AT (1) | ATE184045T1 (de) |
DE (1) | DE69511832D1 (de) |
GB (1) | GB9426066D0 (de) |
Cited By (12)
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US8524087B2 (en) | 2009-12-23 | 2013-09-03 | Uop Llc | Low metal, low water biomass-derived pyrolysis oils and methods for producing the same |
US8864999B2 (en) | 2009-12-23 | 2014-10-21 | Uop Llc | Methods for regenerating acidic ion-exchange resins and reusing regenerants in such methods |
US8961743B2 (en) | 2007-11-20 | 2015-02-24 | Ensyn Renewables, Inc. | Rapid thermal conversion of biomass |
US9044727B2 (en) | 2011-09-22 | 2015-06-02 | Ensyn Renewables, Inc. | Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material |
US9102888B2 (en) | 2011-12-12 | 2015-08-11 | Ensyn Renewables, Inc. | Methods for renewable fuels with reduced waste streams |
US9127208B2 (en) | 2006-04-03 | 2015-09-08 | Pharmatherm Chemicals, Inc. | Thermal extraction method and product |
US9315739B2 (en) | 2011-08-18 | 2016-04-19 | Kior, Llc | Process for upgrading biomass derived products |
US9347005B2 (en) | 2011-09-13 | 2016-05-24 | Ensyn Renewables, Inc. | Methods and apparatuses for rapid thermal processing of carbonaceous material |
US9382489B2 (en) | 2010-10-29 | 2016-07-05 | Inaeris Technologies, Llc | Renewable heating fuel oil |
US9422478B2 (en) | 2010-07-15 | 2016-08-23 | Ensyn Renewables, Inc. | Char-handling processes in a pyrolysis system |
US9441887B2 (en) | 2011-02-22 | 2016-09-13 | Ensyn Renewables, Inc. | Heat removal and recovery in biomass pyrolysis |
US9447350B2 (en) | 2010-10-29 | 2016-09-20 | Inaeris Technologies, Llc | Production of renewable bio-distillate |
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WO2001094498A1 (en) * | 2000-06-08 | 2001-12-13 | Valtion Teknillinen Tutkimuskeskus | Method and apparatus for producing pyrolysis oil |
GB0616298D0 (en) | 2006-08-16 | 2006-09-27 | Univ Aston | Biomass pyrolysis |
CN101531922B (zh) * | 2009-04-10 | 2012-05-23 | 中国林业科学研究院林产化学工业研究所 | 反应萃取提质生物质热解油的方法 |
CN101812376B (zh) * | 2010-04-20 | 2012-08-22 | 浙江大学 | 一种微波条件下酯化生物油催化提质的方法 |
US20110284359A1 (en) | 2010-05-20 | 2011-11-24 | Uop Llc | Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas |
US8323456B2 (en) | 2010-08-26 | 2012-12-04 | Kior, Inc. | Removal of bound water from bio-oil |
EP2638129A2 (de) | 2010-09-14 | 2013-09-18 | IFP Energies nouvelles | Verfahren zur aufwertung von bioöl auf kohlenwassertoff-brennstoffe für den transport |
US9062264B2 (en) | 2010-10-29 | 2015-06-23 | Kior, Inc. | Production of renewable bio-gasoline |
US8377152B2 (en) | 2010-10-29 | 2013-02-19 | Kior, Inc. | Production of renewable bio-distillate |
US8628589B2 (en) | 2011-02-11 | 2014-01-14 | Kior, Inc. | Renewable heating oil |
US9193926B2 (en) | 2010-12-15 | 2015-11-24 | Uop Llc | Fuel compositions and methods based on biomass pyrolysis |
US9039790B2 (en) | 2010-12-15 | 2015-05-26 | Uop Llc | Hydroprocessing of fats, oils, and waxes to produce low carbon footprint distillate fuels |
US9617489B2 (en) | 2011-02-11 | 2017-04-11 | Inaeris Technologies, Llc | Liquid bio-fuels |
US8669405B2 (en) | 2011-02-11 | 2014-03-11 | Kior, Inc. | Stable bio-oil |
US9387415B2 (en) | 2011-08-18 | 2016-07-12 | Inaeris Technologies, Llc | Process for upgrading biomass derived products using liquid-liquid extraction |
US10427069B2 (en) | 2011-08-18 | 2019-10-01 | Inaeris Technologies, Llc | Process for upgrading biomass derived products using liquid-liquid extraction |
US8636888B2 (en) | 2011-08-18 | 2014-01-28 | Kior, Inc. | Process for improving the separation of oil/water mixtures |
US10041667B2 (en) | 2011-09-22 | 2018-08-07 | Ensyn Renewables, Inc. | Apparatuses for controlling heat for rapid thermal processing of carbonaceous material and methods for the same |
US10400175B2 (en) | 2011-09-22 | 2019-09-03 | Ensyn Renewables, Inc. | Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material |
FR2987842B1 (fr) | 2012-03-12 | 2015-02-27 | IFP Energies Nouvelles | Procede optimise pour la valorisation de bio-huiles en carburants hydrocarbones |
US10633606B2 (en) | 2012-12-10 | 2020-04-28 | Ensyn Renewables, Inc. | Systems and methods for renewable fuel |
FI126782B (en) | 2013-03-08 | 2017-05-31 | Upm Kymmene Corp | Process for conversion of bio-oil |
DK3337966T3 (da) | 2015-08-21 | 2022-02-28 | Ensyn Renewables Inc | Opvarmningssystem med flydende biomasse |
EP3565664A4 (de) | 2016-12-29 | 2020-08-05 | Ensyn Renewables, Inc. | Entmetallisierung von flüssiger biomasse |
-
1994
- 1994-12-22 GB GBGB9426066.8A patent/GB9426066D0/en active Pending
-
1995
- 1995-12-22 AT AT95309400T patent/ATE184045T1/de not_active IP Right Cessation
- 1995-12-22 DE DE69511832T patent/DE69511832D1/de not_active Expired - Lifetime
- 1995-12-22 EP EP95309400A patent/EP0718392B1/de not_active Expired - Lifetime
Cited By (22)
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US9127208B2 (en) | 2006-04-03 | 2015-09-08 | Pharmatherm Chemicals, Inc. | Thermal extraction method and product |
US8961743B2 (en) | 2007-11-20 | 2015-02-24 | Ensyn Renewables, Inc. | Rapid thermal conversion of biomass |
US8864999B2 (en) | 2009-12-23 | 2014-10-21 | Uop Llc | Methods for regenerating acidic ion-exchange resins and reusing regenerants in such methods |
US8524087B2 (en) | 2009-12-23 | 2013-09-03 | Uop Llc | Low metal, low water biomass-derived pyrolysis oils and methods for producing the same |
US9422478B2 (en) | 2010-07-15 | 2016-08-23 | Ensyn Renewables, Inc. | Char-handling processes in a pyrolysis system |
US9447350B2 (en) | 2010-10-29 | 2016-09-20 | Inaeris Technologies, Llc | Production of renewable bio-distillate |
US9382489B2 (en) | 2010-10-29 | 2016-07-05 | Inaeris Technologies, Llc | Renewable heating fuel oil |
US9441887B2 (en) | 2011-02-22 | 2016-09-13 | Ensyn Renewables, Inc. | Heat removal and recovery in biomass pyrolysis |
US9315739B2 (en) | 2011-08-18 | 2016-04-19 | Kior, Llc | Process for upgrading biomass derived products |
US9347005B2 (en) | 2011-09-13 | 2016-05-24 | Ensyn Renewables, Inc. | Methods and apparatuses for rapid thermal processing of carbonaceous material |
US9044727B2 (en) | 2011-09-22 | 2015-06-02 | Ensyn Renewables, Inc. | Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material |
US9102889B2 (en) | 2011-12-12 | 2015-08-11 | Ensyn Renewables, Inc. | Fluidized catalytic cracker riser quench system |
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Also Published As
Publication number | Publication date |
---|---|
EP0718392A1 (de) | 1996-06-26 |
DE69511832D1 (de) | 1999-10-07 |
ATE184045T1 (de) | 1999-09-15 |
GB9426066D0 (en) | 1995-02-22 |
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