EP2712936A1 - Produits de sucre et son procédé de fabrication - Google Patents

Produits de sucre et son procédé de fabrication Download PDF

Info

Publication number
EP2712936A1
EP2712936A1 EP20130186469 EP13186469A EP2712936A1 EP 2712936 A1 EP2712936 A1 EP 2712936A1 EP 20130186469 EP20130186469 EP 20130186469 EP 13186469 A EP13186469 A EP 13186469A EP 2712936 A1 EP2712936 A1 EP 2712936A1
Authority
EP
European Patent Office
Prior art keywords
chloride
mixing solution
bromide
sugar product
fabricating
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.)
Granted
Application number
EP20130186469
Other languages
German (de)
English (en)
Other versions
EP2712936B1 (fr
Inventor
Ruey-Fu Shih
Jia-Yuan Chen
Hui-Tsung Lin
Hom-Ti Lee
Hou-Peng Wan
Wei-Chun Hung
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Industrial Technology Research Institute ITRI
Original Assignee
Industrial Technology Research Institute ITRI
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
Priority claimed from US13/973,072 external-priority patent/US20140090641A1/en
Priority claimed from CN201310435004.8A external-priority patent/CN103710472B/zh
Application filed by Industrial Technology Research Institute ITRI filed Critical Industrial Technology Research Institute ITRI
Publication of EP2712936A1 publication Critical patent/EP2712936A1/fr
Application granted granted Critical
Publication of EP2712936B1 publication Critical patent/EP2712936B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C13SUGAR INDUSTRY
    • C13KSACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00Glucose; Glucose-containing syrups
    • C13K1/02Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials

Definitions

  • the technical field relates to a sugar product and fabricating method thereof.
  • the world is facing problems such as the gradual extraction and depletion of petroleum reserves, and changes to the earth's atmosphere due to the greenhouse effect. In order to ensure the sustainability of human life, it has become a world trend to gradually decrease the use of petrochemical energy and petroleum feedstock and to develop new sources of renewable energy and materials.
  • Lignocellulose is the main ingredient of biomass, which is the most abundant organic substance in the world. Lignocellulose mainly consists of 38-50% cellulose, 23-32% hemicellulose and 15-25% lignin. Cellulose generates glucose through hydrolysis. However, it is difficult for chemicals to enter the interior of cellulose molecules for depolymerization due to strong intermolecular and intramolecular hydrogen bonding and Van de Waal forces and the complex aggregate structure of cellulose with high-degree crystallinity. The main methods of hydrolyzing cellulose are enzyme hydrolysis and acid hydrolysis. However, there is significant imperfection in these two technologies, therefore, it is difficult to apply widely.
  • enzyme hydrolysis can be carried out at room temperature, which is an environmentally friendly method due to the rarity of byproducts, no production of anti-sugar fermentation substances, and integration with the fermentation process.
  • a complicated pretreatment process is required, hydrolytic activity is low, the reaction rate is slow, and cellulose hydrolysis enzyme is expensive.
  • Dilute acid hydrolysis generally uses comparatively cheap sulfuric acid as a catalyst, but it must operate in a corrosion-resistant pressure vessel at more than 200°C, requiring high-level equipment; simultaneously, the temperature of the dilute acid hydrolysis is high, the byproduct thereof is plentiful, and the sugar yield is low. Concentrated acid hydrolysis can operate at lower temperature and normal pressure. However, there are problems of strong corrosivity of concentrated acid, complications in the post-treatment process of the hydrolyzed solution, large consumption of acid, and difficulties with recycling, among other drawbacks.
  • One embodiment of the disclosure provides a sugar product, comprising: a sugar mixture comprising glucose, xylose, mannose, arabinose and oligosaccharides thereof with a weight ratio of 2-15wt%; an acid compound with a weight ratio of 48-97wt%; and a salt compound with a weight ratio of 1-50wt%.
  • One embodiment of the disclosure provides a method for fabricating a sugar product, comprising: mixing formic acid or acetic acid and lithium chloride, magnesium chloride, calcium chloride, zinc chloride, iron chloride, lithium bromide, magnesium bromide, calcium bromide, zinc bromide, iron bromide, or heteropoly acid to form a mixing solution; adding a cellulosic biomass to the mixing solution for a dissolution reaction; and adding water to the mixing solution for a hydrolysis reaction to obtain a sugar product.
  • a method for fabricating a sugar product comprising the following steps. First, formic acid or acetic acid and lithium chloride, magnesium chloride, calcium chloride, zinc chloride, iron chloride, lithium bromide, magnesium bromide, calcium bromide, zinc bromide, iron bromide, or heteropoly acid are mixed to form a mixing solution. A cellulosic biomass is added to the mixing solution for a dissolution reaction. Water is added to the mixing solution for a hydrolysis reaction to obtain a sugar product.
  • the lithium chloride or lithium bromide has a weight ratio of about 5-20wt% or 10-20wt% in the mixing solution.
  • the calcium chloride or calcium bromide has a weight ratio of about 12-40wt% or 12-30wt% in the mixing solution.
  • the amount of water added is larger than the total molar equivalent of monosaccharides hydrolyzed from the cellulosic biomass.
  • the hydrolysis reaction has a reaction temperature of about 50-150°C or 60-105 °C and a reaction time of about 30-180 minutes or 30-120 minutes.
  • the sugar product fabricated by the method may comprise a sugar mixture, an acid compound, and a salt compound.
  • the sugar mixture may comprise glucose, xylose, mannose, arabinose and oligosaccharides thereof with a weight ratio of about 2-15wt% in the sugar product.
  • the acid compound may comprise formic acid or acetic acid with a weight ratio of about 48-97wt% in the sugar product.
  • the salt compound may comprise lithium chloride, magnesium chloride, calcium chloride, zinc chloride, iron chloride, lithium bromide, magnesium bromide, calcium bromide, zinc bromide, or iron bromide with a weight ratio of about 1-50wt% in the sugar product.
  • the method further comprises adding inorganic acid to the mixing solution before, during or after the dissolution reaction.
  • the inorganic acid may comprise sulfuric acid or hydrochloric acid.
  • the inorganic acid has a weight ratio of about 1-2wt% in the mixing solution.
  • the adding amount of the chloride salt or the bromide salt may be reduced, for example, the weight ratio of the magnesium chloride, the magnesium bromide, the calcium chloride or the calcium bromide in the mixing solution may be reduced to about 1-10wt%, and the weight ratio of the lithium chloride, the lithium bromide, the zinc chloride, the zinc bromide, the iron chloride or the iron bromide in the mixing solution may be reduced to about 1-5wt%.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (75wt% of formic acid, 25wt% of calcium chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (6wt% of Avicel ® cellulose) for a dissolution reaction (65 °C , 90 minutes) to form a yellow, homogeneous, and transparent liquid, as recorded in Table 1.
  • Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of magnesium chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65 °C , 120 minutes) to form an amber, homogeneous, and transparent liquid, as recorded in Table 1.
  • Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of magnesium chloride).
  • ⁇ -cellulose Sigma Corporation, C8002 was added to the mixing solution (5wt% of ⁇ -cellulose) for a dissolution reaction (65°C, 120 minutes) to form an amber, homogeneous, and transparent liquid, as recorded in Table 1.
  • Table 1 Examples Salt (wt%) Cellulose (wt%) Dissolution temp.
  • Formic acid and lithium chloride (LiCl) were mixed and heated to form a mixing solution (90wt% of formic acid, 10wt% of lithium chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and lithium bromide (LiBr) were mixed and heated to form a mixing solution (90wt% of formic acid, 10wt% of lithium bromide).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 0.5 hour). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and sodium bromide (NaBr) were mixed and heated to form a mixing solution (82wt% of formic acid, 18wt% of sodium bromide).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 9 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and calcium bromide (CaBr 2 ) were mixed and heated to form a mixing solution (88wt% of formic acid, 12wt% of calcium bromide).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and barium bromide (BaBr 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of barium bromide).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of magnesium chloride (saturated solution)).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65 °C , 2 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and magnesium chloride (MgCl 2 ) were mixed and heated to form a mixing solution (90wt% of formic acid, 10wt% of magnesium chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 12 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (75wt% of formic acid, 25wt% of calcium chloride (saturated solution)).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65°C, 1.5 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (82.5wt% of formic acid, 17.5wt% of calcium chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 2 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed and heated to form a mixing solution (88wt% of formic acid, 12wt% of calcium chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (60wt% of formic acid, 40wt% of zinc chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (50°C, 0.25 hour). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (80wt% of formic acid, 20wt% of zinc chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65°C, 0.25 hour). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (95wt% of formic acid, 5wt% of zinc chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Formic acid and iron chloride (FeCl 3 ) were mixed and heated to form a mixing solution (98wt% of formic acid, 2wt% of iron chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 3 hours). The dissolution of cellulose was observed using a polarizing microscope, as recorded in Table 2.
  • Magnesium carbonate (MgCO 3 ) precipitate was then removed from the mixing solution.
  • the total weight of the reducing sugar was measured using 3,5-dinitro-salicylic acid (DNS) method.
  • DNS 3,5-dinitro-salicylic acid
  • the yield of the reducing sugar was then calculated.
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 3.
  • Formic acid and magnesium chloride (MgCl 2 ) were mixed by stirring and heated to 70°C under 1 atm to form a mixing solution (90wt% of formic acid, 10wt% of magnesium chloride).
  • Avicel ® cellulose (Sigma Corporation, Avicel-pH-105-27NI) was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 6 hours).
  • water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (120 minutes).
  • saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed by stirring and heated to 50°C under 1 atm to form a mixing solution (85wt% of formic acid, 15wt% of calcium chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (50°C, 4 hours).
  • water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (60 minutes).
  • saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 4.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed by stirring and heated to 70°C under 1 atm to form a mixing solution (88wt% of formic acid, 12wt% of calcium chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (70°C, 4 hours).
  • water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (60 minutes).
  • saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 4.
  • Formic acid and calcium chloride (CaCl 2 ) were mixed by stirring and heated to 90°C under 1 atm to form a mixing solution (90wt% of formic acid, 10wt% of calcium chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI
  • was added to the mixing solution 5wt% of Avicel ® cellulose
  • dissolution reaction 90°C, 4 hours.
  • water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (60 minutes).
  • saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
  • Formic acid and zinc chloride (ZnCl 2 ) were mixed by stirring and heated to 50°C under 1 atm to form a mixing solution (60wt% of formic acid, 40wt% of zinc chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (50°C).
  • water was added to the mixing solution (50wt% of water) and the mixing solution was heated to 100°C for a hydrolysis reaction (30 minutes).
  • saturated sodium carbonate (Na 2 CO 3 ) aqueous solution was added to neutralize the mixing solution.
  • Zinc carbonate (ZnCO 3 ) precipitate was then removed from the mixing solution.
  • the total weight of the reducing sugar was measured using 3,5-dinitro-salicylic acid (DNS) method.
  • DNS 3,5-dinitro-salicylic acid
  • the yield of the reducing sugar was then calculated.
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the weight of the cellulose. The result is shown in Table 5.
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • Formic acid and zinc chloride (ZnCl 2 ) were mixed by stirring and heated to 55 °C under 1 atm to form a mixing solution (60wt% of formic acid, 40wt% of zinc chloride).
  • Dried corn stalks (comprising 44.5wt% of glucan, 12.4wt% of xylan, 4.6wt% of acid-soluble lignin, 24.4wt% of acid-insoluble lignin, 2.7wt% of water and 3.8wt% of ash) was added to the mixing solution (5wt% of corn stalks) for a dissolution reaction (55°C).
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the yield of the glucose is the ratio of the moles of the produced glucose and the moles of the glucose monomers contained in the cellulose in the bagasse.
  • the yield of the xylose is the ratio of the moles of the produced xylose and the moles of the xylose monomers contained in the hemicellulose in the bagasse.
  • the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the total weight of the cellulose and hemicellulose in the bagasse. The result is shown in Table 9.
  • 98wt% of H 2 SO 4 , iron chloride (FeCl 3 ) and formic acid were mixed by stirring and heated to 55°C under 1 atm to form a mixing solution (1wt% of H 2 SO 4 , 2wt% of iron chloride, 97wt% of formic acid).
  • Dried bagasse (comprising 40.7wt% of glucan, 20.5wt% of xylan, 2.9wt% of Arab polysaccharides, 27.4wt% of lignin, 3.3wt% of ash and 5.2wt% of other ingredients) was added to the mixing solution (10wt% of bagasse) for a dissolution reaction (65°C).
  • the reducing sugar comprised glucose, xylose, mannose, arabinose and oligosaccharides thereof.
  • the yield of the glucose is the ratio of the moles of the produced glucose and the moles of the glucose monomers contained in the cellulose in the bagasse.
  • the yield of the xylose is the ratio of the moles of the produced xylose and the moles of the xylose monomers contained in the hemicellulose in the bagasse.
  • the yield of the reducing sugar is the ratio of the total weight of the reducing sugar and the total weight of the cellulose and hemicellulose in the bagasse.
  • Formic acid acetic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (54wt% of formic acid, 6wt% of acetic acid and 40wt% of zinc chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (60°C, 60 minutes), forming an amber transparent liquid with an uniform phase. The dissolution of cellulose was observed using a polarizing microscope. The cellulose was completely dissolved.
  • Formic acid acetic acid and zinc chloride (ZnCl 2 ) were mixed and heated to form a mixing solution (50wt% of formic acid, 10wt% of acetic acid and 40wt% of zinc chloride).
  • Avicel ® cellulose Sigma Corporation, Avicel-pH-105-27NI was added to the mixing solution (5wt% of Avicel ® cellulose) for a dissolution reaction (65°C, 60 minutes), forming an amber transparent liquid with an uniform phase. The dissolution of cellulose was observed using a polarizing microscope. The cellulose was completely dissolved.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)
  • Processing Of Solid Wastes (AREA)
EP13186469.6A 2012-09-28 2013-09-27 Produits de sucre et son procédé de fabrication Active EP2712936B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261707576P 2012-09-28 2012-09-28
US13/973,072 US20140090641A1 (en) 2012-09-28 2013-08-22 Sugar products and fabrication method thereof
CN201310435004.8A CN103710472B (zh) 2012-09-28 2013-09-23 糖产物及其制备方法

Publications (2)

Publication Number Publication Date
EP2712936A1 true EP2712936A1 (fr) 2014-04-02
EP2712936B1 EP2712936B1 (fr) 2015-10-07

Family

ID=49237122

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13186469.6A Active EP2712936B1 (fr) 2012-09-28 2013-09-27 Produits de sucre et son procédé de fabrication

Country Status (2)

Country Link
EP (1) EP2712936B1 (fr)
TW (1) TWI467023B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016099273A1 (fr) 2014-12-18 2016-06-23 Avantium Knowledge Centre B.V. Procédé pour la préparation d'une solution contenant un saccharide à partir d'une biomasse cellulosique torréfiée

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI615398B (zh) * 2015-12-10 2018-02-21 財團法人工業技術研究院 醣類之製備方法
CN106938196A (zh) 2015-12-10 2017-07-11 财团法人工业技术研究院 固体催化剂及应用该催化剂的醣类的制备方法
MY186792A (en) 2016-02-04 2021-08-20 Ind Tech Res Inst Method for separating hydrolysis product of biomass
CN107034317A (zh) * 2016-02-04 2017-08-11 财团法人工业技术研究院 生质物水解产物的分离方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4452640A (en) * 1982-05-11 1984-06-05 Purdue Research Foundation Quantitative hydrolysis of cellulose to glucose using zinc chloride
WO2006007691A1 (fr) * 2004-07-16 2006-01-26 Iogen Energy Corporation Procede d'elaboration de flux de produit sucre a partir d'une biomasse cellulosique
US20080102502A1 (en) * 2006-10-25 2008-05-01 Brian Foody Inorganic salt recovery during processing of lignocellulosic feedstocks
WO2010104371A1 (fr) * 2009-03-12 2010-09-16 Universiti Malaya Conversion de matériaux cellulosiques en glucose à utiliser dans la production de bioéthanol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI121885B (fi) * 2007-11-09 2011-05-31 Chempolis Oy Menetelmä sokerituotteen valmistamiseksi

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4452640A (en) * 1982-05-11 1984-06-05 Purdue Research Foundation Quantitative hydrolysis of cellulose to glucose using zinc chloride
WO2006007691A1 (fr) * 2004-07-16 2006-01-26 Iogen Energy Corporation Procede d'elaboration de flux de produit sucre a partir d'une biomasse cellulosique
US20080102502A1 (en) * 2006-10-25 2008-05-01 Brian Foody Inorganic salt recovery during processing of lignocellulosic feedstocks
WO2010104371A1 (fr) * 2009-03-12 2010-09-16 Universiti Malaya Conversion de matériaux cellulosiques en glucose à utiliser dans la production de bioéthanol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016099273A1 (fr) 2014-12-18 2016-06-23 Avantium Knowledge Centre B.V. Procédé pour la préparation d'une solution contenant un saccharide à partir d'une biomasse cellulosique torréfiée

Also Published As

Publication number Publication date
TWI467023B (zh) 2015-01-01
TW201412993A (zh) 2014-04-01
EP2712936B1 (fr) 2015-10-07

Similar Documents

Publication Publication Date Title
EP2712936B1 (fr) Produits de sucre et son procédé de fabrication
JP2006223152A (ja) セルロース溶剤による溶解と加水分解の組合せによるバイオマス処理方法
Kassaye et al. Synergistic effect of ionic liquid and dilute sulphuric acid in the hydrolysis of microcrystalline cellulose
EP2781605B1 (fr) Procédé de séparation d'hydrate de carbone
US20140090641A1 (en) Sugar products and fabrication method thereof
EP3094734B1 (fr) Procédé de fractionnement d'oligosaccharides à partir de déchets d'origine agricole
CA2848752A1 (fr) Traitement d'une biomasse lignocellulosique avec un acide organique en c1-c2 pour produire une pate a papier acylee, de l'hemicellulose, de la lignine et des sucres, et fermentation des sucres
CN102517403B (zh) 一种利用高温液态水制备半纤维素低聚糖的方法
CN101255479A (zh) 一种将木质纤维素高效糖化的预处理方法
CN102311983A (zh) 一种生物质制取糖的方法
US9695484B2 (en) Sugar products and fabrication method thereof
Nahar et al. Effects of reduced severity ammonia pretreatment on pelleted corn stover
US20140216442A1 (en) Method for preparing sugars
CN103710472B (zh) 糖产物及其制备方法
Pérez-Pérez et al. Synergetic effect of hydrothermal and deep eutectic solvents (DES) pretreatments on Robinia wood fractionation for the manufacture of bioethanol and cellulose nanocrystals
Liao et al. Optimizing tri-acid mixture hydrolysis: An improved strategy for efficient xylooligosaccharides production from corncob
CN105385722A (zh) 一种预处理木质纤维生物质提高其产糖率的方法
AU2014201106B2 (en) Sugar Products And Fabrication Method Thereof
CA2844556C (fr) Produits de sucre et leur methode de fabrication
Siccama et al. Steering the formation of cellobiose and oligosaccharides during enzymatic hydrolysis of asparagus fibre
CN102976895A (zh) 利用农作物废料制作木糖醇的方法
CN102381960A (zh) 一种从玉米皮中提取阿魏酸、对-香豆酸及戊聚糖的方法
CN105525044A (zh) 一种在极性非质子体系中超低酸催化水解纤维素、半纤维素原料制备还原糖的方法
CN117385107A (zh) 一种高得率制备木糖水解液的方法
MX2014015014A (es) Metodo de tratamiento enzimatico de un material lignocelulosico solido.

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

17P Request for examination filed

Effective date: 20140514

RBV Designated contracting states (corrected)

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RIC1 Information provided on ipc code assigned before grant

Ipc: C13K 1/02 20060101AFI20150416BHEP

Ipc: C12P 19/02 20060101ALI20150416BHEP

INTG Intention to grant announced

Effective date: 20150504

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 753806

Country of ref document: AT

Kind code of ref document: T

Effective date: 20151015

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602013003357

Country of ref document: DE

REG Reference to a national code

Ref country code: SE

Ref legal event code: TRGR

REG Reference to a national code

Ref country code: NL

Ref legal event code: MP

Effective date: 20151007

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 753806

Country of ref document: AT

Kind code of ref document: T

Effective date: 20151007

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20160107

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20160207

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20160108

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20160208

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602013003357

Country of ref document: DE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

26N No opposition filed

Effective date: 20160708

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20170531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160927

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160930

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160930

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160930

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160927

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20170927

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO

Effective date: 20130927

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20160930

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20170927

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20151007

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20230927

Year of fee payment: 11

Ref country code: DE

Payment date: 20230927

Year of fee payment: 11