WO2002002826A1 - Procede de preparation de sucre fermentable a partir de matieres premieres contenant de la cellulose - Google Patents

Procede de preparation de sucre fermentable a partir de matieres premieres contenant de la cellulose Download PDF

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Publication number
WO2002002826A1
WO2002002826A1 PCT/NO2001/000280 NO0100280W WO0202826A1 WO 2002002826 A1 WO2002002826 A1 WO 2002002826A1 NO 0100280 W NO0100280 W NO 0100280W WO 0202826 A1 WO0202826 A1 WO 0202826A1
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WIPO (PCT)
Prior art keywords
acid
sugar
extraction agent
ketone
mixture
Prior art date
Application number
PCT/NO2001/000280
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English (en)
Inventor
Knut Helland
Karl Weydahl
Original Assignee
Knut Helland
Karl Weydahl
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 Knut Helland, Karl Weydahl filed Critical Knut Helland
Priority to AU2001266434A priority Critical patent/AU2001266434A1/en
Publication of WO2002002826A1 publication Critical patent/WO2002002826A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups
    • C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class
    • C13K13/002—Xylose
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the present invention relates to a method of hydrolysis of cellulose in raw materials, such as paper, for further 5 production of fermentable sugars. Furthermore, the invention applies to methods which are described in the introduction to the claims 1 and 8.
  • the invention concerns some of the introductory steps which are used in the production of ethanol during anaerobic 0 fermentation of sugar from raw materials containing cellulose.
  • a flow diagram for the complete process is shown in the enclosed figure.
  • a first step in such a process is that the cellulose is hydrolysed (a first hydrolysis step) with mineral acid to 5 form soluble sugars. (Smaller amounts of organic acids are also formed, these must be neutralised after the subsequent post-hydrolysis step) .
  • the mineral acid is removed by extraction (dissolution) with an organic solvent, while cleaved cellulose (the sugar) is precipi- 0 tated out as a solid phase with the insoluble lignin from the cellulose.
  • a residual sugar follows the acid over into the extraction agent, and is interesting to recover by recycling the acid.
  • a third step the organic solvent is evaporated, the acid is enriched up by evaporation, and acid containing a part of the mentioned dissolved sugar is recycled to the first step for hydrolysis of the cellulose.
  • the evaporation 5 takes place at low pressure and low temperature so that as little sugar in the acid as possible shall be converted to non-fermentable compounds.
  • the solution is neutralised by addition of 15 dolomite or lime and precipitated solid matter, such as gypsum (calcium sulphate) and the lignin, is separated by filtration or centrifugation.
  • precipitated solid matter such as gypsum (calcium sulphate) and the lignin
  • step 6 The further steps in the process up to ethanol consist of glucose/mannose being fermented in step 6 by immobilised 35 yeast, and ethanol being removed continuously from the bioreactor by means of a suitable extraction agent (for example tall oil-fatty acid) .
  • a suitable extraction agent for example tall oil-fatty acid
  • step 7 The regeneration of the extraction agent takes place in step 7 in which ethanol (35% by vol) is evaporated by gentle heating at reduced pressure.
  • the condensate from the column is distilled continuously to 96% ethanol.
  • step 8 is shown in which xylose and xylulose are fermented.
  • the raw materials for industrial processes for ethanol production are mainly sugar juices from sugar cane, different species of grain and the mentioned cellulose which can originate from cellulose-containing waste and wood materials. Using such wastes, the cellulose is broken down into fermentable sugar either enzymatically or by acid catalysis.
  • the present invention concerns the latter type in which the catalysis is carried out with a mineral acid, in particular sulphuric acid and phosphoric acid.
  • Cellulose-containing material means wood materials which contain cellulose, hemi-cellulose and lignin. Besides, cellulose-containing waste can include paper waste, recyclable paper or cartons, or saw dust, saw mill waste and other wood materials.
  • Cellulose is a polysaccharide built up of glucose units and forms a polymer chain approximately without branches. Cellulose is soluble in strong sulphuric acid, fuming hydrochloric acid and concentrated phosphoric acid. When the cellulose is hydrolysed in strong mineral acid, the cellulose is initially dissolved, and is subsequently broken down into smaller sugar molecules .
  • Hemi-cellulose is a polysaccharide which is built up of different sugar monomers, such as glucose, mannose and galactose, as well as pentose sugars such as xylose and arabinose. Hemi-cellulose is soluble in dilute mineral paths.,., .acid.
  • the lignin in the cellulose, the cellulose and the hemi- cellulose account for more than 90% of the dry matter in wooden materials. Lignin is built up of aromatic monomers and is insoluble in the mineral acid which is used in the hydrolysis .
  • HYDROLYSIS OF CELLULOSE, PREVIOUSLY KNOWN METHODS In industrial production of ethanol, the processes in which the wood pulp is hydrolysed with mineral acid dominate. The cellulose will, dependent on the acid concentration, either be dissolved or swell up. The sugar formed is fermented to ethanol in a separate process step, and is concentrated by " distillation. Examples of processes for hydrolysis are:
  • the Scholler process in which dilute sulphuric acid (less that 1% by weight sulphuric acid) is used to cleave cellulose.
  • the hydrolysis is carried out at high temperature, 140-180 °C. To prevent decomposition of sugar the hydrolysis time is short.
  • the sulphuric acid is neutralised with lime or dolomite after the hydrolysis.
  • the ,. process gives a significantly lower yield of fermentable sugar than the Klason process.
  • the Bexg ⁇ s process in which concentrated hydrochloric acid is used for the hydrolysis of cellulose.
  • the hydrolysis of cellulose is carried out at low temperature 20-130 °C . Hydrochloric acid is recycled by evaporation of the hydrolysate.
  • the yield of fermentable sugar is high, above 90% of theoretical yield.
  • hydrochloric acid is used for the hydrolysis, and the hydrochloric acid is evaporated under vacuum, and recycled in the process.
  • the hydrolysate (mineral acid plus cleaved cellulose) is brought into contact with a suitable organic
  • acetophenone is used as the extraction agent for concentrated hydrochloric acid.
  • concentrated hydrochloric acid for the 35 depolymerisation of cellulose
  • hydrochloric acid is recovered by evaporation of the hydrolysate.
  • the purpose of the extraction of hydrochloric acid with acetophenone as the extraction agent is to avoid the hydrochloric acid- water azeotrop by recovery of the hydrochloric acid by distillation.
  • Hydrochloric acid in the organic phase is separated from the organic extraction agent by standard distillation or evaporation.
  • isobutanol which is a C 4 alcohol has a boiling point of 108 °C at 1 atm, while the boiling point for N-heptanol, which is a C alcohol, is 175.8 °C at 1 atm.
  • acetone is used as the extraction agent for methanesulphonic acid and zinc chloride. Additionally, the corresponding use of acetone as the extraction agent for sulphuric acid, sulphuric acid/phosphoric acid and sulphuric acid/benzenesulphonic acid is described in a 10 report from HiB (University College Bergen) dated
  • a mixture of a lower alcohol (C ⁇ -C 4 alcohol) and a lower ketone (C 3 -C 6 ketone) is used as the extraction agent.
  • Acid solution from previous experiments was recycled by: 1) 5 Evaporation of methylethyl ketone, 2) Evaporation of acid solution under vacuum.
  • the volume of the acid solution after the evaporation under vacuum was 155 ml.
  • the fraction of mineral acids recycled 0 from the previous experiments was about 96%.
  • the composition of the acid solution after evaporation was ' • -" ⁇ about 50% (by weight) sulphuric acid, about 20% (by weight) phosphoric acid and the rest water/sugar.
  • the filter cake consisted of precipitated sugar, insoluble lignin and mineral acid. Mineral acid in the filter cake was partially removed by washing the filter cake three times with 100 ml dry methylethyl ketone, 150 ml dry 0 methylethyl ketone and 150 ml dry acetone, respectively.
  • the filter cake was then suspended in 300 ml water and the residual extraction agent from the last wash was evaporated under reduced pressure. The suspension was then heated to 5 120 °C and held for 2.25 hours in a pressure cooker.
  • lignin was separated from dissolved sugar by filtration.
  • the amount of lignin after drying of the filter cake was 14.57 g.
  • the filtrate was neutralised with lime to pH ⁇ 5 and thereafter filtered. Consumption of lime for the neutralisation was 7.48 g.
  • dissolved sugar was converted to ethanol by fermentation with ordinary baker' s yeast ⁇ Saccharomyces cerevisiae) .
  • the yield of ethanol after fermentation was determined by gas chromatography analysis of the solution. The yield of ethanol was 14.21 ml (76.4% of the theoretical yield) .
  • the acid solution from Example 1 was recycled by 1) evaporation of methylethyl ketone, 2) evaporation of acid solution under vacuum.
  • the fraction of mineral acid recycled from the previous experiment was about 96%.
  • the hydrolysate (mineral acid plus broken down newspaper) was suspended in 1050 ml recycled methylethyl ketone (from the previous experiment) . After cooling of the suspension to about -12 °C, the suspension was filtered. The filter cake consisted of precipitated sugar, insoluble lignin and mineral acid. The mineral acid in the filter cake was partially removed by washing the filter cake three times with 100 ml methylethyl ketone (2- butanone) , 150 ml dry methylethyl ketone and 150 ml dry acetone, respectively.
  • the filter cake was then suspended in 300 ml water and the remaining extraction agent from the last wash evaporated under reduced pressure. The suspension was then heated to 120 °C and held for 2.25 hours in a pressure cooker, and the lignin separated from the dissolved sugar by filtration. The amount of lignin after drying of the filter cake was 16.15 g.
  • the dissolved sugar was converted to ethanol by fermentation with ordinary baker's yeast ( Saccharomyces cerevisiae) .
  • the yield of ethanol after fermentation was determined by gas chromatography analysis of the solution. The yield of ethanol was 12.90 ml (69.4% of the theoretical yield).
  • the volume of acid solution after evaporation under vacuum was 166 ml.
  • the fraction of mineral acid recycled from the previous experiment was about 98%.
  • the composition of the acid solution after evaporation was about 50% by weight sulphuric acid, about 20% by weight phosphoric acid and the rest water/sugar.
  • To the acid solution was added 3 ml concentrated sulphuric acid and 1 ml water so that the total volume of the acid solution was 170 ml.
  • the acid solution was thereafter mixed with 50.0 g newspaper and heated to 55 °C and held for 3.5 hours. After being held at 55 °C for 1.25 hours, 20 ml water was added and a further 20 ml water after 2.5 hours. After 3.5 hours, the hydrolysate (mineral acid plus broken down newspaper) was suspended in 800 ml recycled methylethyl ketone (from previous experiments) . After cooling of the suspension to about -10 °C, the suspension was filtered. The filter cake consisted of precipitated sugar, insoluble lignin and mineral acid.
  • the mineral acid in the filter cake was partially removed by washing 3 times with 250 ml cold methylethyl ketone, a solution of 50 ml methanol and 100 ml methylethyl ketone, and a solution of 10 ml water, 50 ml methanol and 100 ml methylethyl ketone, respectively.
  • the filter cake was then suspended in 450 ml water and the residual extraction agent from the last wash was evaporated under reduced pressure.
  • the suspension was thereafter heated to 120 °C and held for 5 hours in a pressure cooker.
  • the lignin was separated from the dissolved sugar by filtration.
  • the amount of lignin after drying of the filter cake was 16.07 g.
  • the dissolved sugar was converted to ethanol by fermentation with ordinary baker's yeast ⁇ Saccharomyces cerevisiae) .
  • the yield of ethanol after fermentation was determined by gas chromatography analysis of the solution. The yield of ethanol was 10.90 ml (58.6% of theoretical yield).
  • Example 4 The acid solution from previous experiments was recycled by: 1) Evaporation of the organic extraction agent.
  • the extraction agent was recycled by freezing out dissolved water in a freezer and filtration in the freezer. Analysis of recycled extraction agent by gas chromatography showed that the composition was 0.8% by volume water, 21.0% (by volume) propanol, 44.5% by volume methylethyl ketone and 33.7% by volume methylisobutyl ketone.
  • the filter cake consisted of precipitated sugar, insoluble lignin and mineral acid.
  • the mineral acid in the filter cake was partially removed by suspending the filter cake in the extraction agent and filtering the suspension after cooling.
  • the washing process was carried out twice with 350 ml extraction agent for each washing.
  • the filter cake was then suspended in 300 ml water and the residual extraction agent from the last wash was evaporated under reduced pressure. The suspension was thereafter heated at 130 °C and held for 1,5 hours in a bench autoclave. The lignin was separated from dissolved sugar by filtration, and the amount of lignin after drying of the filter cake was 15,64 g. The filtrate was then neutralised with lime to pH ⁇ 5 and thereafter filtered. Consumption of lime at neutralisation was 4.10 g. After filtration of the neutral suspension and washing of the filter cake, the dissolved sugar was converted to ethanol by fermentation with ordinary baker' s yeast ⁇ Saccharomyces cerevisiae) . The yield of ethanol after fermentation was determined by gas chromatography analysis of the solution. The yield of ethanol was 13.10 ml (70.4% of theoretical yield).
  • the acid solution from Example 4 was recycled by:
  • the hydrolysate (mineral acid plus decomposed newspaper) was suspended in 1050 ml recycled extraction agent. After cooling of the suspension to about -10 °C, the suspension was filtered. The filter cake consisted of precipitated sugar, insoluble lignin and mineral acid. The mineral acid of the filter cake was partially removed by suspending the filter cake in the extraction agent and filtering the suspension after cooling. The washing process was carried out twice with 350 ml extraction agent for each washing.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne un procédé de production de sucre fermentable à partir de matières premières contenant de la cellulose qui consiste à effectuer une hydrolyse desdites matières premières avec une solution contenant de l'acide, notamment de l'acide sulfurique, ensuite à extraire l'acide du mélange, qui suite à l'hydrolyse comprend de l'acide, de l'eau, du sucre et une fraction de lignine insoluble, à l'aide d'un agent d'extraction, et éventuellement une séparation subséquente de l'acide à partir de l'agent d'extraction et sa recirculation. Le procédé est caractérisé en ce qu'on utilise un mélange d'un alcool inférieur (alcool en C1-C4) et un cétone inférieur en tant qu'agent d'extraction.
PCT/NO2001/000280 2000-07-04 2001-07-03 Procede de preparation de sucre fermentable a partir de matieres premieres contenant de la cellulose WO2002002826A1 (fr)

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Application Number Priority Date Filing Date Title
AU2001266434A AU2001266434A1 (en) 2000-07-04 2001-07-03 Methods for preparing fermentable sugar from cellulose containing raw materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NO20003448 2000-07-04
NO20003448A NO312070B1 (no) 2000-07-04 2000-07-04 Fremgangsmåte ved en prosess for fremstilling av gj¶rbart sukker fra celluloseholdige råstoffer

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009036674A1 (fr) * 2007-09-18 2009-03-26 Peihao Chen Procédé de récupération d'acide sulfurique à partir d'hydrolysat d'acide concentré de matériau de cellulose végétal
WO2010014503A1 (fr) * 2008-07-31 2010-02-04 E.I. Du Pont De Nemours And Company Décristallisation de biomasse cellulosique avec un mélange d'acides comprenant des acides phosphorique et sulfurique
WO2010038021A2 (fr) * 2008-10-02 2010-04-08 Weyland As Procédé de production d’alcool
WO2010046619A1 (fr) * 2008-10-22 2010-04-29 Weyland As Procédé pour la production d’alcool
WO2010069583A1 (fr) 2008-12-18 2010-06-24 Eni S.P.A. Procede de production de sucres a partir de biomasse
WO2010128272A1 (fr) * 2009-05-07 2010-11-11 Weylands As Procédé pour la production d'alcools
WO2010146331A2 (fr) 2009-06-19 2010-12-23 Weyland As Procédé de production d'alcool
WO2012061596A1 (fr) * 2010-11-05 2012-05-10 Shell Oil Company Traitement de biomasse pour produire des matières utiles pour des biocarburants
US8304535B2 (en) 2008-11-20 2012-11-06 E I Du Pont De Nemours And Company Sugar production by decrystallization and hydrolysis of polysaccharide enriched biomass
EP2862890A1 (fr) * 2012-05-03 2015-04-22 Virdia Ltd. Procédés d'extraction de la lignin de la biomasse
WO2015097445A1 (fr) * 2013-12-24 2015-07-02 Weyland As Procédé de traitement de matériau cellulosique
US9115467B2 (en) 2010-08-01 2015-08-25 Virdia, Inc. Methods and systems for solvent purification
US9234413B2 (en) 2009-06-25 2016-01-12 Shell Oil Company Water injection systems and methods
US9382593B2 (en) 2012-05-07 2016-07-05 Shell Oil Company Continuous or semi-continuous process for treating biomass to produce materials useful for biofuels
US9410216B2 (en) 2010-06-26 2016-08-09 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US9476106B2 (en) 2010-06-28 2016-10-25 Virdia, Inc. Methods and systems for processing a sucrose crop and sugar mixtures
US9493851B2 (en) 2012-05-03 2016-11-15 Virdia, Inc. Methods for treating lignocellulosic materials
US9512495B2 (en) 2011-04-07 2016-12-06 Virdia, Inc. Lignocellulose conversion processes and products
US9617608B2 (en) 2011-10-10 2017-04-11 Virdia, Inc. Sugar compositions
US9657146B2 (en) 2013-03-14 2017-05-23 Virdia, Inc. Methods for treating lignocellulosic materials
US9663836B2 (en) 2010-09-02 2017-05-30 Virdia, Inc. Methods and systems for processing sugar mixtures and resultant compositions
US9683005B2 (en) 2013-05-03 2017-06-20 Virdia, Inc. Methods for preparing thermally stable lignin fractions
US9822420B2 (en) 2013-03-18 2017-11-21 Industrial Technology Research Institute Method of separating carbohydrate
US10138332B2 (en) 2013-05-03 2018-11-27 Virdia, Inc. Methods for treating lignocellulosic materials
US10767308B2 (en) 2014-07-09 2020-09-08 Virdia, Inc. Methods for separating and refining lignin from black liquor and compositions thereof
US11078548B2 (en) 2015-01-07 2021-08-03 Virdia, Llc Method for producing xylitol by fermentation
US11091815B2 (en) 2015-05-27 2021-08-17 Virdia, Llc Integrated methods for treating lignocellulosic material

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US8052953B2 (en) 2007-09-18 2011-11-08 Peihao Chen Method for recovering sulfuric acid from concentrated acid hydrolysate of plant cellulose material
WO2009036674A1 (fr) * 2007-09-18 2009-03-26 Peihao Chen Procédé de récupération d'acide sulfurique à partir d'hydrolysat d'acide concentré de matériau de cellulose végétal
CN102112633A (zh) * 2008-07-31 2011-06-29 纳幕尔杜邦公司 包含磷酸和硫酸的酸混合物对纤维质生物质的消晶作用
WO2010014503A1 (fr) * 2008-07-31 2010-02-04 E.I. Du Pont De Nemours And Company Décristallisation de biomasse cellulosique avec un mélange d'acides comprenant des acides phosphorique et sulfurique
JP2011529685A (ja) * 2008-07-31 2011-12-15 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー リン酸と硫酸とを含む酸混合物を用いたセルロース系バイオマスの脱結晶化
WO2010038021A2 (fr) * 2008-10-02 2010-04-08 Weyland As Procédé de production d’alcool
WO2010038021A3 (fr) * 2008-10-02 2010-08-26 Weyland As Procédé de production d’alcool
WO2010046619A1 (fr) * 2008-10-22 2010-04-29 Weyland As Procédé pour la production d’alcool
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US8304535B2 (en) 2008-11-20 2012-11-06 E I Du Pont De Nemours And Company Sugar production by decrystallization and hydrolysis of polysaccharide enriched biomass
WO2010069583A1 (fr) 2008-12-18 2010-06-24 Eni S.P.A. Procede de production de sucres a partir de biomasse
JP2012525835A (ja) * 2009-05-07 2012-10-25 ウェイランド エーエス アルコールの製造方法
US9217184B2 (en) 2009-05-07 2015-12-22 Weyland As Process for the production of alcohols
WO2010128272A1 (fr) * 2009-05-07 2010-11-11 Weylands As Procédé pour la production d'alcools
AU2010244264B2 (en) * 2009-05-07 2014-03-20 Weyland As Process for the production of alcohols
CN102421921A (zh) * 2009-05-07 2012-04-18 韦兰公司 生产醇的方法
CN102421921B (zh) * 2009-05-07 2013-07-10 韦兰公司 生产醇的方法
JP2012529903A (ja) * 2009-06-19 2012-11-29 ウェイランド エーエス アルコール製造方法
EA018962B1 (ru) * 2009-06-19 2013-12-30 Вейлэнд Ас Способ получения сахаров и спиртов из целлюлозного материала
CN102459619A (zh) * 2009-06-19 2012-05-16 韦兰公司 从纤维素材料生产糖和醇的方法
WO2010146331A3 (fr) * 2009-06-19 2011-10-06 Weyland As Procédé de production d'alcool
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US9410216B2 (en) 2010-06-26 2016-08-09 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US10760138B2 (en) 2010-06-28 2020-09-01 Virdia, Inc. Methods and systems for processing a sucrose crop and sugar mixtures
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US10240217B2 (en) 2010-09-02 2019-03-26 Virdia, Inc. Methods and systems for processing sugar mixtures and resultant compositions
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US9290821B2 (en) 2010-11-05 2016-03-22 Shell Oil Company Treating biomass to produce materials useful for biofuels
US9212401B2 (en) 2010-11-05 2015-12-15 Shell Oil Company Treating biomass to produce materials useful for biofuels
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US10961595B2 (en) 2010-11-05 2021-03-30 Shell Oil Company Treating biomass to produce materials useful for biofuels
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US9512495B2 (en) 2011-04-07 2016-12-06 Virdia, Inc. Lignocellulose conversion processes and products
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NO312070B1 (no) 2002-03-11

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