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WO2009015663A2 - Drying method within acid hydrolysis of plant biomasses - Google Patents

Drying method within acid hydrolysis of plant biomasses Download PDF

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Publication number
WO2009015663A2
WO2009015663A2 PCT/DE2008/001284 DE2008001284W WO2009015663A2 WO 2009015663 A2 WO2009015663 A2 WO 2009015663A2 DE 2008001284 W DE2008001284 W DE 2008001284W WO 2009015663 A2 WO2009015663 A2 WO 2009015663A2
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WIPO (PCT)
Prior art keywords
biomass
hydrolysis
hydrochloric acid
acid
drying method
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Ceased
Application number
PCT/DE2008/001284
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German (de)
French (fr)
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WO2009015663A3 (en
Inventor
Matthias Schmidt
Frank Kose
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Green Sugar GmbH
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Green Sugar GmbH
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Publication of WO2009015663A3 publication Critical patent/WO2009015663A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H8/00—Macromolecular compounds derived from lignocellulosic materials
    • 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
    • C13K1/06—Glucose; Glucose-containing syrups obtained by saccharification of starch or raw materials containing starch
    • 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 hydrolysis of biomass is increasingly becoming a focus of economic interest as fossil fuels become scarcer.
  • the aim is to unravel all carbohydrates that can be used in plant biomass in an economically technical process.
  • the totality of all carbohydrates of a plant is called green sugar for the sake of simplicity, since the targeted carbohydrates are not only cellulose, but also hemicelluloses, starch, sucrose, pectins and the like. is.
  • the hydrolysis can be carried out in principle by the biological / enzymatic and chemical routes.
  • the latter variant exploits the hydrolytic action of acids of different concentrations.
  • we distinguish between two approaches One uses diluted acids at elevated pressure (eg 5bar) and elevated temperature (eg 150 0 C).
  • Saccharification with highly concentrated acids had economic importance in Germany until the end of the 1950s and until the late 1980s in the former Soviet Union. Saccharified wood in the form of wood chips or sawdust. Other substrates were agricultural waste products, such as grain husks. All have in common a high degree of dryness. This was ensured, inter alia, that the hydrolysis apparatus was preceded by drying. The reason for this is the strong heat development that results from supplying the highly concentrated acid. This can lead to the charring of the biomass. Of the Green sugar can be obtained only with losses and by taking along degradation products such as furan derivatives, which in turn can interfere in the further process (eg in the fermentation of ethanol). A variety of patent solutions attest to the economic importance. To meet the warming process, various efforts have been made.
  • the degree of dryness will be of particular importance in the future in the technical process, since in a bio-based economy it will not only depend on the utilization of wood, but on the utilization of all vegetable biomass. This has economic significance, in particular, since many biomass, such as green waste or sea algae, are moist and must be taken into account with the water content as quickly as possible. Conversely, it is economically advantageous if an operator of a hydrolysis plant can utilize biomass regardless of the degree of drying.
  • This invention describes a procedure that allows the economical use of different degrees of drying biomass for acid hydrolysis with highly concentrated acids, primarily hydrochloric acid. Description of the invention
  • the invention is based on the idea that highly concentrated acids are water-attracting. Therefore, all vegetable biomasses are subjected to pretreatment with a 15-25% hydrochloric acid solution. In this concentration range, the hydrochloric acid has a sufficient dehydrating effect with a moderate heat development. This pretreatment has many different consequences and advantages.
  • the dehydration can be carried out in the existing hydrolysis reactors.
  • the removal of the water takes place during the workup of the Grünzuckerhydrolysate by evaporation of hydrochloric acid and water.
  • the energy required for downstream water removal corresponds to the energy that is generated when the biomass is dried, e.g. in drum dryers, is needed. Net results by eliminating the drying equipment, a reduction in investment costs for the installation of a hydrochloric acid hydrolysis system.
  • hydrochloric acid is already used for gentle prehydrolysis, with C5 sugars (eg xylose), proteins and salts being dissolved.
  • C5 sugars eg xylose
  • proteins and salts being dissolved.
  • sugar solutions containing almost no crystallization-inhibiting substances are obtained.
  • inexpensive plastics such as PVC-C, for the construction of hydrolysis reactors, which would otherwise not withstand exposure to heat and aggressive media such as highly concentrated acids.
  • step A 1 kg of miscanthus straw with a dry matter content of 75% is treated successively in an extraction apparatus with 2 kg of 20% (A), 1.5 kg of 32% (B) and 1 kg of 41% (C) hydrochloric acid.
  • step A all proteins, salts and part of the hemicelluloses are solubilized.
  • the proportion of water in the biomass contributes to the dilution of the hydrolysis acid.
  • the temperature in the reactor rises from 2O 0 C to 26 ° C.
  • step B all portions of the hemicellulose and a portion of the cellulose are solubilized. This gives 1.5 kg of 32% hydrochloric acid, in which 156 g of C5 sugar (especially xylose), 81 g of glucose and 14 g of acetic acid are dissolved (by deacetylation of lignin).
  • step C the remaining carbohydrates are split hydrolytically. One obtains lkg of 41% hydrochloric acid in which 255 g of glucose, 8 g of Cellotetrose, 7 g of cellodiose and 18 g of acetic acid are dissolved. 150 g of hydrochloric acid-free lignin remain in the reactor.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Processing Of Solid Wastes (AREA)
  • Saccharide Compounds (AREA)

Abstract

Disclosed is a method for hydrolyzing plant biomasses regardless of the type and origin by means of highly concentrated acids, primarily hydrogen chloride. Said method is characterized in that the actual hydrolysis is preceded by a preliminary treatment of the biomass with hydrogen chloride at a concentration ranging from 15 to 25 percent such that the biomass does not have to be dried.

Description

Trocknungsverfahren innerhalb der sauren Hydrolyse von pflanzlichen BiomassenDrying process within the acid hydrolysis of plant biomass

Stand der TechnikState of the art

Die Hydrolyse von Biomassen tritt mit Verknappung der fossilen Rohstoffe zunehmend in den Fokus des wirtschaftlichen Interesses. Ziel ist der AufSchluss aller in der pflanzlichen Biomasse nutzbaren Kohlenhydrate in einem wirtschaftlich technischen Prozess. Die Gesamtheit aller Kohlenhydrate einer Pflanze wird zur Vereinfachung des weiteren Grünzucker genannt, da es sich bei den anvisierten Kohlenhydraten nicht nur um Zellulose, sondern auch Hemicellulosen, Stärke, Sucrose, Pectine u.a. handelt.The hydrolysis of biomass is increasingly becoming a focus of economic interest as fossil fuels become scarcer. The aim is to unravel all carbohydrates that can be used in plant biomass in an economically technical process. The totality of all carbohydrates of a plant is called green sugar for the sake of simplicity, since the targeted carbohydrates are not only cellulose, but also hemicelluloses, starch, sucrose, pectins and the like. is.

Die Hydrolyse kann prinzipiell auf dem biologisch/ enzymatischen und dem chemischen Wege erfolgen. Letztere Variante nutzt die hydrolytische Wirkung von Säuren unterschiedlicher Konzentration aus. Vereinfachend unterscheidet man zwei Vorgehensweisen. Eine verwendet verdünnte Säuren bei erhöhtem Druck (z.B. 5bar) und erhöhter Temperatur (z.B. 1500C). Die zweite verwendet hochkonzentrierte Säuren bei annähernd Raumtemperatur bzw. -druck. Verwendete Säuren sind vor allem Halogensäuren und Schwefelsäure .The hydrolysis can be carried out in principle by the biological / enzymatic and chemical routes. The latter variant exploits the hydrolytic action of acids of different concentrations. To simplify, we distinguish between two approaches. One uses diluted acids at elevated pressure (eg 5bar) and elevated temperature (eg 150 0 C). The second uses highly concentrated acids at near room temperature or pressure. Acids used are mainly halogen acids and sulfuric acid.

Die Verzuckerung mit hochkonzentrierten Säuren hatte bis zum Ende der 50-iger Jahre in Deutschland und bis Ende der 80-iger Jahre in der ehemaligen Sowjetunion wirtschaftliche Bedeutung. Verzuckert wurde Holz in Form von Holzspänen oder Sägemehl. Weitere Substrate waren landwirtschaftliche Abfallprodukte, wie Getreidespelzen. Allen gemeinsam ist ein hoher Grad an Trockenheit. Dieser wurde unter anderem dadurch gewährleistet, dass der Hydrolyseapparatur eine Trocknung vorgeschaltet wurde. Hintergrund dafür ist die starke Wärmeentwicklung, die sich durch Zuführung der hochkonzentrierten Säure ergibt. Diese kann bis zur Verkohlung der Biomasse führen. Der Grünzucker kann nur mit Verlusten und unter Mitnahme von Abbauprodukten wie z.B Furanderivaten gewonnen werden, welche wiederum im weiteren Prozess (z.B. bei der Vergärung zu Ethanol) störend wirken können. Eine Vielzahl von Patentlösungen bezeugen die wirtschaftliche Bedeutung. Um dem Erwärmungsprozess zu begegnen, wurden verschiedene Anstrengungen unternommen. So wurde beispielsweise eine organisch indifferente Flüssigkeit verwendet, in welcher das Reaktionsgut in der Schwebe gehalten wurde, um die Wärme abzuführen. Es ergaben sich jedoch umfangreiche technische Probleme bei der Umsetzung des Konzeptes. Ein anderer Ansatz sah die Vorkühlung des zu hydrolysierenden Gutes als auch der Säure vor. Andere Verfahren führten den Wärmestrom mittels der Hydrolyselösung durch spezielle Öffnungen aus der Apparatur ab, wobei die verwendete Säure, bezüglich der Hydrolyse, an Wirkungsgrad verlor.Saccharification with highly concentrated acids had economic importance in Germany until the end of the 1950s and until the late 1980s in the former Soviet Union. Saccharified wood in the form of wood chips or sawdust. Other substrates were agricultural waste products, such as grain husks. All have in common a high degree of dryness. This was ensured, inter alia, that the hydrolysis apparatus was preceded by drying. The reason for this is the strong heat development that results from supplying the highly concentrated acid. This can lead to the charring of the biomass. Of the Green sugar can be obtained only with losses and by taking along degradation products such as furan derivatives, which in turn can interfere in the further process (eg in the fermentation of ethanol). A variety of patent solutions attest to the economic importance. To meet the warming process, various efforts have been made. For example, an organic inert liquid was used in which the reaction mixture was kept in suspension to remove the heat. However, there were extensive technical problems in the implementation of the concept. Another approach was to pre-cool the material to be hydrolyzed as well as the acid. Other processes carried the heat flow through the hydrolysis solution through special openings in the apparatus, whereby the acid used, with respect to the hydrolysis, lost in efficiency.

Der Trocknungsgrad wird in Zukunft im technischen Prozess von besonderer Bedeutung sein, da es bei einer biobasierten Wirtschaft nicht nur auf die Nutzbarmachung von Holz sondern auf die Nutzbarmachung von sämtlichen pflanzlichen Biomassen ankommen wird. Dies hat insbesondere deshalb wirtschaftliche Bedeutung, da viele Biomassen, wie Grünschnitt oder Meeresalgen feucht anfallen und bei möglichst schneller Verarbeitung dem Wassergehalt Rechnung getragen werden muss. Umgekehrt ist es wirtschaftlich vorteilhaft, wenn ein Betreiber einer Hydrolyseanlage unabhängig vom Trocknungsgrad Biomassen verwerten kann.The degree of dryness will be of particular importance in the future in the technical process, since in a bio-based economy it will not only depend on the utilization of wood, but on the utilization of all vegetable biomass. This has economic significance, in particular, since many biomass, such as green waste or sea algae, are moist and must be taken into account with the water content as quickly as possible. Conversely, it is economically advantageous if an operator of a hydrolysis plant can utilize biomass regardless of the degree of drying.

Die ErfindungThe invention

Diese Erfindung beschreibt eine Vorgehensweise, welche die wirtschaftliche Verwendung von Biomassen mit unterschiedlichem Trocknungsgrad für die saure Hydrolyse mit hochkonzentrierten Säuren, vornehmlich Salzsäure, ermöglicht. Beschreibung der ErfindungThis invention describes a procedure that allows the economical use of different degrees of drying biomass for acid hydrolysis with highly concentrated acids, primarily hydrochloric acid. Description of the invention

Die Erfindung basiert auf dem Gedanken, dass hochkonzentrierte Säuren wasseranziehend wirken. Deshalb werden alle pflanzlichen Biomassen einer Vorbehandlung mit einer 15-25%- igen Salzsäurelösung unterworfen. In diesem Konzentrationsbereich besitzt die Salzsäure eine genügend entwässernde Wirkung bei einer gleichzeitig moderaten Wärmeentwicklung. Diese Vorbehandlung hat unterschiedlichste Konsequenzen und Vorteile.The invention is based on the idea that highly concentrated acids are water-attracting. Therefore, all vegetable biomasses are subjected to pretreatment with a 15-25% hydrochloric acid solution. In this concentration range, the hydrochloric acid has a sufficient dehydrating effect with a moderate heat development. This pretreatment has many different consequences and advantages.

Erstens wird der Biomasse durch diese Vorbehandlung Wasser entzogen. In einem Experiment mit nasser Biomasse (60% Trockensubstanz) und hochkonzentrierter Säure (32%ige Salzsäure) , wie sie üblich zur sauren Vor-Hydrolyse verwendet wird, wurde festgestellt, dass die Temperatur auf über 800C stieg. Bei sukzessiver Verwendung von 20%iger und 32%iger Salzsäure stieg die Temperatur nicht über 400C. Damit werden Grünzuckerverluste vermieden.First, the biomass is deprived of water by this pretreatment. In an experiment with wet biomass (60% dry substance) and highly concentrated acid (32% hydrochloric acid) commonly used for acid pre-hydrolysis, it was found that the temperature rose above 80 ° C. With successive use of 20% and 32% hydrochloric acid, the temperature did not rise above 40 0 C. This green sugar losses are avoided.

Zweitens entfällt eine Vortrocknungsapparatur. Der Wasserentzug kann in den bereits vorhandenen Hydrolysereaktoren durchgeführt werden. Die Entfernung des Wassers erfolgt bei der Aufarbeitung der Grünzuckerhydrolysate durch Verdampfung der Salzsäure und des Wassers. Die dafür benötigte Energie für eine nachgeschaltete Wasserentfernung entspricht der Energie, die bei einer Trocknung der Biomasse, z.B. in Trommeltrocknern, benötigt wird. Netto ergibt sich durch Wegfall der Trockenapparatur eine Verringerung der Investkosten für die Installation einer Hydrolyseanlage auf Salzsäurebasis .Second, eliminates a predrying apparatus. The dehydration can be carried out in the existing hydrolysis reactors. The removal of the water takes place during the workup of the Grünzuckerhydrolysate by evaporation of hydrochloric acid and water. The energy required for downstream water removal corresponds to the energy that is generated when the biomass is dried, e.g. in drum dryers, is needed. Net results by eliminating the drying equipment, a reduction in investment costs for the installation of a hydrochloric acid hydrolysis system.

Drittens wird mit der 15%-25%igen Salzsäure bereits eine sanfte Vorhydrolyse durchgeführt, wobei sich vor allem C5- Zucker (z.B. Xylose) , Proteine und Salze lösen. In den folgenden Hydrolyseschritten erhält man Zuckerlösungen, die fast keine die Kristallisation hemmende Stoffe enthalten. Viertens ist es durch die Begrenzung der bei der Hydrolyse entstehenden Wärme möglich, preiswerte Kunststoffe, wie PVC-C für die Konstruktion von Hydrolyse-Reaktoren zu verwenden, die anderenfalls der Belastung durch Wärme und aggressive Medien, wie hochkonzentrierte Säuren nicht standhalten würden.Third, the 15% -25% hydrochloric acid is already used for gentle prehydrolysis, with C5 sugars (eg xylose), proteins and salts being dissolved. In the following hydrolysis steps, sugar solutions containing almost no crystallization-inhibiting substances are obtained. Fourth, by limiting the heat generated during the hydrolysis, it is possible to use inexpensive plastics, such as PVC-C, for the construction of hydrolysis reactors, which would otherwise not withstand exposure to heat and aggressive media such as highly concentrated acids.

Ausführungsbeispielembodiment

Beispiel:Example:

1 kg Miscanthus-Stroh mit einem Trockensubstanzgehalt von 75 % wird in einer Extraktionsapparatur sukzessive mit 2kg 20 %iger (A), 1,5kg 32 %iger (B) und 1 kg 41%iger (C) Salzsäure behandelt. Im Schritt A werden alle Proteine, Salze und ein Teil der Hemicellulosen in Lösung gebracht. Der Anteil von Wasser in der Biomasse trägt zur Verdünnung der Hydrolyse- Säure bei. Man erhält 2,25 kg 17,7%iger Salzsäure, in welcher 17g Salze (in Form ihrer Chloride) , 20g Aminosäuren und 91g monomere Zucker, vor allem in Form von Xylose, gelöst sind. Die Temperatur im Reaktor steigt von 2O0C auf 26°C. Im Schritt B werden alle Anteile der Hemicellulose und ein Teil der Cellulose in Lösung gebracht. Man erhält 1,5kg 32%ige Salzsäure, in welcher 156 g C5-Zucker (vor allem Xylose) , 81 g Glucose und 14g Essigsäure (durch Deacetylierung aus Lignin) gelöst sind. Im Schritt C werden die restlichen Kohlenhydrate hydrolytisch gespalten. Man erhält lkg 41%ige Salzsäure, in welcher 255g Glucose, 8g Cellotetrose, 7g Cellodiose und 18g Essigsäure gelöst sind. Im Reaktor verbleiben 150g salzsäurefreies Lignin. 1 kg of miscanthus straw with a dry matter content of 75% is treated successively in an extraction apparatus with 2 kg of 20% (A), 1.5 kg of 32% (B) and 1 kg of 41% (C) hydrochloric acid. In step A, all proteins, salts and part of the hemicelluloses are solubilized. The proportion of water in the biomass contributes to the dilution of the hydrolysis acid. This gives 2.25 kg of 17.7% hydrochloric acid, in which 17g salts (in the form of their chlorides), 20g amino acids and 91g monomeric sugars, especially in the form of xylose, are dissolved. The temperature in the reactor rises from 2O 0 C to 26 ° C. In step B, all portions of the hemicellulose and a portion of the cellulose are solubilized. This gives 1.5 kg of 32% hydrochloric acid, in which 156 g of C5 sugar (especially xylose), 81 g of glucose and 14 g of acetic acid are dissolved (by deacetylation of lignin). In step C, the remaining carbohydrates are split hydrolytically. One obtains lkg of 41% hydrochloric acid in which 255 g of glucose, 8 g of Cellotetrose, 7 g of cellodiose and 18 g of acetic acid are dissolved. 150 g of hydrochloric acid-free lignin remain in the reactor.

Claims

Ansprüche claims Verfahren zur Hydrolyse von pflanzlichen Biomassen unabhängig von der Art und Herkunft mit hochkonzentrierten Säuren, vornehmlich Salzsäure ausgezeichnet dadurch,Process for the hydrolysis of vegetable biomass, regardless of the type and origin, with highly concentrated acids, primarily hydrochloric acid, characterized • dass der eigentlichen Hydrolyse eine Vorbehandlung der Biomasse mit Salzsäure im Konzentrationsbereich von 15- 25% vorgeschaltet ist und dadurch eine Trocknung der Biomasse entfällt • that the actual hydrolysis is preceded by pretreatment of the biomass with hydrochloric acid in the concentration range of 15-25%, thereby eliminating drying of the biomass
PCT/DE2008/001284 2007-08-01 2008-07-29 Drying method within acid hydrolysis of plant biomasses Ceased WO2009015663A2 (en)

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DE102007037341.6 2007-08-01
DE102007037341A DE102007037341A1 (en) 2007-08-01 2007-08-01 Drying process within the acid hydrolysis of plant biomass

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WO2009015663A2 true WO2009015663A2 (en) 2009-02-05
WO2009015663A3 WO2009015663A3 (en) 2009-12-17

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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
US9631246B2 (en) 2012-05-03 2017-04-25 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
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US9410216B2 (en) 2010-06-26 2016-08-09 Virdia, Inc. Sugar mixtures and methods for production and use thereof
US10752878B2 (en) 2010-06-26 2020-08-25 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
US10760138B2 (en) 2010-06-28 2020-09-01 Virdia, Inc. Methods and systems for processing a sucrose crop and sugar mixtures
US9115467B2 (en) 2010-08-01 2015-08-25 Virdia, Inc. Methods and systems for solvent purification
US11242650B2 (en) 2010-08-01 2022-02-08 Virdia, Llc Methods and systems for solvent purification
US10240217B2 (en) 2010-09-02 2019-03-26 Virdia, Inc. Methods and systems for processing sugar mixtures and resultant compositions
US9663836B2 (en) 2010-09-02 2017-05-30 Virdia, Inc. Methods and systems for processing sugar mixtures and resultant compositions
US9512495B2 (en) 2011-04-07 2016-12-06 Virdia, Inc. Lignocellulose conversion processes and products
US10876178B2 (en) 2011-04-07 2020-12-29 Virdia, Inc. Lignocellulosic conversion processes and products
US11667981B2 (en) 2011-04-07 2023-06-06 Virdia, Llc Lignocellulosic conversion processes and products
US9845514B2 (en) 2011-10-10 2017-12-19 Virdia, Inc. Sugar compositions
US9976194B2 (en) 2011-10-10 2018-05-22 Virdia, Inc. Sugar compositions
US10041138B1 (en) 2011-10-10 2018-08-07 Virdia, Inc. Sugar compositions
US9617608B2 (en) 2011-10-10 2017-04-11 Virdia, Inc. Sugar compositions
US9631246B2 (en) 2012-05-03 2017-04-25 Virdia, Inc. Methods for treating lignocellulosic materials
US9783861B2 (en) 2012-05-03 2017-10-10 Virdia, Inc. Methods for treating lignocellulosic materials
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