WO2000063488A1 - Process for the production of furfural from lignosulphonate waste liquor - Google Patents

Process for the production of furfural from lignosulphonate waste liquor Download PDF

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Publication number
WO2000063488A1
WO2000063488A1 PCT/ZA2000/000072 ZA0000072W WO0063488A1 WO 2000063488 A1 WO2000063488 A1 WO 2000063488A1 ZA 0000072 W ZA0000072 W ZA 0000072W WO 0063488 A1 WO0063488 A1 WO 0063488A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquor
reactor
furfural
process according
pentose
Prior art date
Application number
PCT/ZA2000/000072
Other languages
French (fr)
Inventor
Karl J. Zeitsch
Original Assignee
International Furan Technology (Pty) Limited
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 International Furan Technology (Pty) Limited filed Critical International Furan Technology (Pty) Limited
Priority to AU54999/00A priority Critical patent/AU5499900A/en
Priority to US09/958,936 priority patent/US6642396B1/en
Priority to CA002370561A priority patent/CA2370561C/en
Priority to DE60039860T priority patent/DE60039860D1/en
Priority to EP00940001A priority patent/EP1171665B1/en
Priority to DK00940001T priority patent/DK1171665T3/en
Priority to BRPI0009815-9A priority patent/BR0009815B1/en
Publication of WO2000063488A1 publication Critical patent/WO2000063488A1/en
Priority to NO20015031A priority patent/NO329326B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural

Definitions

  • This invention relates to the production of furfural from hgnosulphonate waste liquor
  • the sulphite pulping process results in a waste liquor which may contain from 0 9 to 5 6 percent of pentose which makes it a candidate for the production of furfural
  • the waste liquor is thickened to a solids content of 50 percent or totally dried, the liquor or solid being sold as hgnosulphonate Pentose is an undesirable constituent of this liquor
  • the waste liquor from the process is saturated with calcium sulphate, so that the high temperature required for furfural production (preferably above 200 degrees Centigrade) results in the rapid and severe deposition of calcium sulphate on the heated surfaces, which renders extended continuous operation impossible
  • a process for the production of furfural from hgnosulphonate waste liquor containing pentose is characterised by maintaining the liquor at boiling point by controlled decompression for a time sufficient for the pentose to be converted to furfural and to be removed in the vapour substantially without reacting with pentose, hgnosulphonate or itself
  • the reactor may be a batch or continuous reactor
  • a hgnosulphonate liquor is heated by steam in a reactor which is continuously depressu ⁇ sed to pressures which are sufficient to maintain boiling of the liquor, the furfural formed migrating to the vapour phase and is discharged with the condensate and recovered
  • the liquor is boiled in a continuous reactor by means of an auxiliary heat source, the liquor being discharged while the furfural formed is substantially instantaneously and completely transferred into the gas phase leaving the reactor and from which it is separated
  • the liquor is heated in the reactor by means of an auxiliary heat source, the liquor being discharged while the furfural formed is substantially instantaneously and completely transferred into the gas phase from which it separated
  • the auxiliary heat source is preferably heated air under pressure and this may be introduced at a low level in the reactor
  • the air percolates through the liquor in the reactor, and by giving up its heat it maintains the liquor in a state of boiling before leaving the reactor
  • the liquor is preferably introduced into the reactor at a temperature of between 180 and 280 degrees Centigrade
  • a control circuit may be provided to maintain the pressure in the head of the reactor at a value slightly below the pressure of the entering liquor In this way the resulting liberating steam causes the liquor to undergo a minor depression to a lower temperature which forces the furfural to the vapour phase, while the heated air maintains a state of boiling of the liquor throughout the entire reactor
  • the furfural produced from the pentose is immediately and completely vapou ⁇ sed as it is formed, and joins the air and some vapou ⁇ sed water to form a gaseous mixture with minimum yield loss of furfural, because reactions between furfural and pentose on the one hand, and with the lignosulphonates on the other hand cannot take place because the pentose and lignosulphonates remain in solution
  • the reaction of furfural with itself is prevented by the absence of hydrogen ions in the vapour phase
  • heated air instead of using heated air as the auxiliary heat source, other suitable heated gases or gas mixtures (such as hot combustion gas) or hot mercury may be used , all of which are readily separated from the liquor at the end of the reaction
  • the heat required by the auxiliary heat agent is relatively small, as in essence all that is required of it is to vapou ⁇ se the furfural produced
  • the low heat of vapourisation of furfural, especially at high temperatures, ensures a low auxiliary heat requirement
  • the yield of furfural increases with the increasing temperature in the reactor as the losses due to reactions with pentose and lignosulphonates as well as bisulphites are suppressed at higher temperatures on account of the entropy effect on all aggregation reactions
  • a pump 1 feeds a hgnosulphonate waste liquor through an in-line mixer 2, where steam injection heats it to a temperature of between 180 and 280 degrees Centigrade, thus raising the pressure accordingly
  • the liquor is submitted to a minor pressure reduction in the head of a thermally insulated columnar reactor 4 and then flows downwardly to leave at the bottom via a cyclone 5 which results in decompression, cooling and thickening
  • Compressed air is heated electrically in a heat exchanger and this is fed via control circuit 7 into the bottom of the reactor
  • the hot air percolates upwardly, giving up its heat to the liquor and thereby maintaining the liquor in a state of ebullition before leaving the head of the reactor via a control circuit 8, a condenser 9, and an atmospheric absorption column 10 equipped with a circulation pump 1 1
  • the control circuit maintains the pressure in the head of the reactor at a value slightly below the pressure of the entering liquor, so that in liberating steam the liquor undergoes a minor depression to a somewhat lower temperature while the hot air introduced at the bottom ensures continuous boiling of the liquor throughout the reactor
  • the furfural formed is instantaneously and completely vapourised and joins the air and vapour to form a gaseous mixture which is condensed in 9 then collected in tank 12
  • Small quantities of furfural entrained by air are recovered in the absorption column and collected in tank 12
  • the input rate of the liquor and the dimensions of the reactor are chosen to match a predetermined residence time of the liquor in the reactor

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A process for the production of furfural from lignosulphonate waste liquor which contains pentose is described, the process essentially comprising the maintenance of a boiling condition of the liquor at predetermined pressures for a sufficient time to convert the pentose to furfural and for the furfural produced to be removed without reacting with pentose, lignosulphonate or itself. Hot air or some other gas under pressure or hot mercury may be used to maintain the boiling of the liquor to ensure that the furfural produced transfers from the liquid to the gas phase and is transported from the reactor in the gas stream. Apparatus for carrying out the process includes a columnar reactor (4) with means (8) to control the pressure, an inlet for preheated liquor, an inlet for hot air under pressure at a low level, an outlet for spent liquor and an outlet for the gaseous phase, from which the furfural is recovered.

Description

WO 00/63488 PCTtZAOO/00072
PROCESS FOR THE PRODUCTION OF FURFURAL FROM LIGNOSULPHONATE WASTE LIQUOR
TECHNICAL FIELD OF THE INVENTION
This invention relates to the production of furfural from hgnosulphonate waste liquor
BACKGROUND OF THE INVENTION
Depending on the particular wood processed, the sulphite pulping process results in a waste liquor which may contain from 0 9 to 5 6 percent of pentose which makes it a candidate for the production of furfural
Conventionally, the waste liquor is thickened to a solids content of 50 percent or totally dried, the liquor or solid being sold as hgnosulphonate Pentose is an undesirable constituent of this liquor
The waste liquor from the process is saturated with calcium sulphate, so that the high temperature required for furfural production (preferably above 200 degrees Centigrade) results in the rapid and severe deposition of calcium sulphate on the heated surfaces, which renders extended continuous operation impossible
If heat exchangers are avoided by substitution of direct steam injection, it is not possible thermodynamically to keep the liquor in a state of boiling during its residence time because the substances in solution elevate the boiling point Thus, at any pressure , the boiling point of the liquor is higher than the condensation point of steam Consequently, the furfural produced from the pentose remains temporarily dissolved in the liquid phase where, under the catalytic effect of the liquor's innate acidity , the furfural can react with pentose, or the hgnosulphonate, and with itself, thus incurring great losses and consequent poor yields It is an object of the present invention to provide a process for the efficient production of furfural from hgnosulphonate liquors as well as apparatus for carrying out the process
DISCLOSURE OF THE INVENTION
According to the invention a process for the production of furfural from hgnosulphonate waste liquor containing pentose is characterised by maintaining the liquor at boiling point by controlled decompression for a time sufficient for the pentose to be converted to furfural and to be removed in the vapour substantially without reacting with pentose, hgnosulphonate or itself
The reactor may be a batch or continuous reactor
In a preferred form batch process, a hgnosulphonate liquor is heated by steam in a reactor which is continuously depressuπsed to pressures which are sufficient to maintain boiling of the liquor, the furfural formed migrating to the vapour phase and is discharged with the condensate and recovered
In a continuous process according to the invention, the liquor is boiled in a continuous reactor by means of an auxiliary heat source, the liquor being discharged while the furfural formed is substantially instantaneously and completely transferred into the gas phase leaving the reactor and from which it is separated
In a form of the invention the liquor is heated in the reactor by means of an auxiliary heat source, the liquor being discharged while the furfural formed is substantially instantaneously and completely transferred into the gas phase from which it separated
The auxiliary heat source is preferably heated air under pressure and this may be introduced at a low level in the reactor The air percolates through the liquor in the reactor, and by giving up its heat it maintains the liquor in a state of boiling before leaving the reactor The liquor is preferably introduced into the reactor at a temperature of between 180 and 280 degrees Centigrade
A control circuit may be provided to maintain the pressure in the head of the reactor at a value slightly below the pressure of the entering liquor In this way the resulting liberating steam causes the liquor to undergo a minor depression to a lower temperature which forces the furfural to the vapour phase, while the heated air maintains a state of boiling of the liquor throughout the entire reactor Thus, the furfural produced from the pentose is immediately and completely vapouπsed as it is formed, and joins the air and some vapouπsed water to form a gaseous mixture with minimum yield loss of furfural, because reactions between furfural and pentose on the one hand, and with the lignosulphonates on the other hand cannot take place because the pentose and lignosulphonates remain in solution The reaction of furfural with itself is prevented by the absence of hydrogen ions in the vapour phase
The residence time in the reactor is chosen for there to be complete conversion of the pentose No addition of acid is required because of the innate acidity of the liquor which effects a sufficiently strong catalysis
No heat exchangers are required, thereby avoiding the problems associated with calcium sulphate as discussed above
Instead of using heated air as the auxiliary heat source, other suitable heated gases or gas mixtures (such as hot combustion gas) or hot mercury may be used , all of which are readily separated from the liquor at the end of the reaction
It will be appreciated that the heat required by the auxiliary heat agent is relatively small, as in essence all that is required of it is to vapouπse the furfural produced The low heat of vapourisation of furfural, especially at high temperatures, ensures a low auxiliary heat requirement The yield of furfural increases with the increasing temperature in the reactor as the losses due to reactions with pentose and lignosulphonates as well as bisulphites are suppressed at higher temperatures on account of the entropy effect on all aggregation reactions
It will be appreciated that it is not necessary to add any acid to the liquor for catalysis, as the innate acidity of the liquor effects a sufficiently strong catalysis
DESCRIPTION OF THE INVENTION
The process of the invention is described below with reference to the accompanying flow diagram
A pump 1 feeds a hgnosulphonate waste liquor through an in-line mixer 2, where steam injection heats it to a temperature of between 180 and 280 degrees Centigrade, thus raising the pressure accordingly By means of a throttle valve 3, the liquor is submitted to a minor pressure reduction in the head of a thermally insulated columnar reactor 4 and then flows downwardly to leave at the bottom via a cyclone 5 which results in decompression, cooling and thickening
Compressed air is heated electrically in a heat exchanger and this is fed via control circuit 7 into the bottom of the reactor The hot air percolates upwardly, giving up its heat to the liquor and thereby maintaining the liquor in a state of ebullition before leaving the head of the reactor via a control circuit 8, a condenser 9, and an atmospheric absorption column 10 equipped with a circulation pump 1 1
The control circuit maintains the pressure in the head of the reactor at a value slightly below the pressure of the entering liquor, so that in liberating steam the liquor undergoes a minor depression to a somewhat lower temperature while the hot air introduced at the bottom ensures continuous boiling of the liquor throughout the reactor The furfural formed is instantaneously and completely vapourised and joins the air and vapour to form a gaseous mixture which is condensed in 9 then collected in tank 12 Small quantities of furfural entrained by air are recovered in the absorption column and collected in tank 12
The input rate of the liquor and the dimensions of the reactor are chosen to match a predetermined residence time of the liquor in the reactor

Claims

1 A process for the production of furfural from hgnosulphonate waste liquor containing pentose characterised in that the liquor is maintained at its boiling point by controlled decompression for a time sufficient for the pentose to be converted to furfural and to be removed in the vapour phase substantially without reacting with pentose, hgnosulphonate or itself
2 A process according to claim 1 characterised in that the hgnosulphonate liquor is heated by steam in a batch reactor which is adapted to be continuously depressuπsed to pressures which are sufficient to maintain boiling of the liquor, the furfural formed migiating to the vapour phase and being discharged with the condensate
3 A process according to claim 1 characterised in that the liquor is boiled in a continuous reactor by means of an auxiliary heat source, the liquor being discharged while the furfural produced is instantaneously and completely transferred into the gas phase from which it is separated
4 A process according to claim 3 characterised in that the auxiliary heat source is heated air under pressure which is introduced at a low level in the reactor, the rate of introduction and the temperature being predetermined for it to give up its heat during percolation through the liquor to maintain the liquor in a state of boiling before leaving the reactor
5 A reactor for carrying out the process according to claims 3 or 4 characterised in that it comprises a columnar cylinder having an inlet for preheated hgnosulphonate waste liquor, means to control the pressure at least in the head of the reactor, an outlet for furfural-stripped liquor at a low level, an inlet for heated auxiliary matter which is readily separable from the liquor, such inlet being at a low level in the reactor, and an outlet at a high level for the gas phase 6 A reactor according to claim 5 characterised in that the outlet for the gas phase includes a condenser
7 A reactor according to claim 5 or 6 characterised in that the heated auxiliary matter is preheated air under pressure
8 A reactor according to any of claims 5 to 7 characterised in that a control circuit is provided which is adapted to maintain the pressure in the head of the reactor at a value slightly below the pressure of the liquor so that in liberating steam the liquor undergoes a minor depression in temperature while the hot auxiliary matter ensures maintenance of continuous boiling of the liquor throughout the reactor
9 A process according to claim 3 characterised in that the partial decompression in the reactor leads to a temperature between 170 and 270 degrees Centigrade
10 A process according to claim 3 characterised in that the auxiliary agent is hot combustion gas
11 A process according to claim 3 characterised in that the auxiliary agent is an advantageous gas mixture
12 A process according to claim 3 characterised in that the auxiliary agent is hot liquid mercury
13 A process according to any of claims 3, 4 or 9 to 1 1 characterised in that the gas used as auxiliary gas is used at a temperature between 400 and 2 000 degrees Centigrade and preferably between 600 and 2 000 degrees Centigrade
PCT/ZA2000/000072 1999-04-16 2000-04-14 Process for the production of furfural from lignosulphonate waste liquor WO2000063488A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AU54999/00A AU5499900A (en) 1999-04-16 2000-04-14 Process for the production of furfural from lignosulphonate waste liquor
US09/958,936 US6642396B1 (en) 1999-04-16 2000-04-14 Process for the production of furfural from lignosulphonate waste liquor
CA002370561A CA2370561C (en) 1999-04-16 2000-04-14 Process for the production of furfural from lignosulphonate waste liquor
DE60039860T DE60039860D1 (en) 1999-04-16 2000-04-14 PROCESS FOR PREPARING FURFURAL FROM LIGNOSULFONATE DEPARTURE
EP00940001A EP1171665B1 (en) 1999-04-16 2000-04-14 Process for the production of furfural from lignosulphonate waste liquor
DK00940001T DK1171665T3 (en) 1999-04-16 2000-04-14 Process for producing furfural from lignosulfonate residue solution
BRPI0009815-9A BR0009815B1 (en) 1999-04-16 2000-04-14 process for the production of furfural from pentose-containing lignosulfonate residual liquor, and reactor to perform the process.
NO20015031A NO329326B1 (en) 1999-04-16 2001-10-16 Process for the preparation of furfural from lignosulfonate waste liquid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19917178.5 1999-04-16
DE19917178A DE19917178A1 (en) 1999-04-16 1999-04-16 Production of furfural from sulfite waste liquor involves heating by direct injection of steam, reaction by boiling under pressure, using easily separated ancillary, and complete vaporization by cooling and depressurization

Publications (1)

Publication Number Publication Date
WO2000063488A1 true WO2000063488A1 (en) 2000-10-26

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PCT/ZA2000/000072 WO2000063488A1 (en) 1999-04-16 2000-04-14 Process for the production of furfural from lignosulphonate waste liquor

Country Status (13)

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US (1) US6642396B1 (en)
EP (1) EP1171665B1 (en)
AT (1) ATE404728T1 (en)
AU (1) AU5499900A (en)
BR (1) BR0009815B1 (en)
CA (1) CA2370561C (en)
DE (2) DE19917178A1 (en)
DK (1) DK1171665T3 (en)
ES (1) ES2307516T3 (en)
NO (1) NO329326B1 (en)
PT (1) PT1171665E (en)
WO (1) WO2000063488A1 (en)
ZA (1) ZA200108552B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103619827A (en) * 2011-06-22 2014-03-05 巴斯夫欧洲公司 Method for dehydrating a carbohydrate-comprising composition
EP3626711A1 (en) * 2018-09-24 2020-03-25 Arbaflame Technology AS Process for the production of furfural

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US8119823B2 (en) * 2008-07-16 2012-02-21 Renmatix, Inc. Solvo-thermal hydrolysis of xylose
US8546560B2 (en) 2008-07-16 2013-10-01 Renmatix, Inc. Solvo-thermal hydrolysis of cellulose
US8282738B2 (en) * 2008-07-16 2012-10-09 Renmatix, Inc. Solvo-thermal fractionation of biomass
US8546561B2 (en) 2008-07-16 2013-10-01 Renmatix, Inc. Nano-catalytic-solvo-thermal technology platform bio-refineries
CN112159869B (en) 2010-01-19 2024-04-19 瑞恩麦特克斯股份有限公司 Use of supercritical fluid to produce fermentable sugars and lignin from biomass
KR101192576B1 (en) 2010-11-30 2012-10-17 코오롱인더스트리 주식회사 Continuous Preparation Method for Furfural from Xylose
CN102228896B (en) * 2011-04-01 2013-05-22 山东万盛环保科技发展有限公司 Furfural slag recycling device
US8801859B2 (en) 2011-05-04 2014-08-12 Renmatix, Inc. Self-cleaning apparatus and method for thick slurry pressure control
US8663800B2 (en) 2011-05-04 2014-03-04 Renmatix, Inc. Lignin production from lignocellulosic biomass
US8759498B2 (en) 2011-12-30 2014-06-24 Renmatix, Inc. Compositions comprising lignin
US9174909B2 (en) 2012-02-02 2015-11-03 Wisconsin Alumni Research Foundation Two-stage, acid-catalyzed conversion of carbohydrates into levulinic acid
CN103193737B (en) * 2013-03-29 2015-01-28 山东龙力生物科技股份有限公司 Method for preparing furfural and co-producing lignin and cellulosic ethanol via plant material
CN107074981A (en) 2014-09-26 2017-08-18 瑞恩麦特克斯股份有限公司 The composition of containing cellulose and its manufacture method
CN116144038B (en) * 2022-11-02 2024-05-07 华南理工大学 Method for preparing furfural, lignin sulfonate and high degradable cellulose by integrated multi-process coupling

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US1838109A (en) * 1930-06-06 1931-12-29 Brown Co Production of furfural
FR1129139A (en) * 1955-07-15 1957-01-16 Paper mill waste liquor treatment process
US2845441A (en) * 1955-11-16 1958-07-29 Brown Co Processes for production of furfural
US4401514A (en) * 1980-04-10 1983-08-30 Vereinigte Edelstahlwerke Ag (Vew) Method for the recovery of furfural, acetic acid and formic acid
EP0124507A1 (en) * 1983-05-02 1984-11-07 Lenzing Aktiengesellschaft Process for obtaining furfural from spent acid liquors in the production of cellulose, and apparatus for carrying out said process
US4533743A (en) * 1983-12-16 1985-08-06 Atlantic Richfield Company Furfural process

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1838109A (en) * 1930-06-06 1931-12-29 Brown Co Production of furfural
FR1129139A (en) * 1955-07-15 1957-01-16 Paper mill waste liquor treatment process
US2845441A (en) * 1955-11-16 1958-07-29 Brown Co Processes for production of furfural
US4401514A (en) * 1980-04-10 1983-08-30 Vereinigte Edelstahlwerke Ag (Vew) Method for the recovery of furfural, acetic acid and formic acid
EP0124507A1 (en) * 1983-05-02 1984-11-07 Lenzing Aktiengesellschaft Process for obtaining furfural from spent acid liquors in the production of cellulose, and apparatus for carrying out said process
US4533743A (en) * 1983-12-16 1985-08-06 Atlantic Richfield Company Furfural process

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103619827A (en) * 2011-06-22 2014-03-05 巴斯夫欧洲公司 Method for dehydrating a carbohydrate-comprising composition
TWI548644B (en) * 2011-06-22 2016-09-11 巴地斯顏料化工廠 Method for dehydrating a carbohydrate-comprising composition
EP3626711A1 (en) * 2018-09-24 2020-03-25 Arbaflame Technology AS Process for the production of furfural
WO2020064641A1 (en) * 2018-09-24 2020-04-02 Arbaflame Technology As Process for the production of furfural
CN112823155A (en) * 2018-09-24 2021-05-18 拉巴弗拉默技术公司 Method for producing furfural
JP2022502382A (en) * 2018-09-24 2022-01-11 アーバフレイム テクノロジー エイ・エスArbaflame Technology AS Furfural manufacturing method
JP7534288B2 (en) 2018-09-24 2024-08-14 アーバフレイム テクノロジー エイ・エス Method for producing furfural

Also Published As

Publication number Publication date
ES2307516T3 (en) 2008-12-01
ZA200108552B (en) 2002-08-22
NO20015031L (en) 2001-12-11
EP1171665B1 (en) 2008-08-13
AU5499900A (en) 2000-11-02
PT1171665E (en) 2008-10-07
BR0009815A (en) 2002-01-08
NO329326B1 (en) 2010-09-27
EP1171665A1 (en) 2002-01-16
ATE404728T1 (en) 2008-08-15
NO20015031D0 (en) 2001-10-16
BR0009815B1 (en) 2011-03-22
DK1171665T3 (en) 2008-12-15
DE19917178A1 (en) 2000-10-19
CA2370561C (en) 2009-06-16
CA2370561A1 (en) 2000-10-26
DE60039860D1 (en) 2008-09-25
US6642396B1 (en) 2003-11-04

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