RU2014101649A - METHOD FOR DEHYDRATING CARBOHYDRATE-CONTAINING COMPOSITIONS - Google Patents

METHOD FOR DEHYDRATING CARBOHYDRATE-CONTAINING COMPOSITIONS Download PDF

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RU2014101649A
RU2014101649A RU2014101649/04A RU2014101649A RU2014101649A RU 2014101649 A RU2014101649 A RU 2014101649A RU 2014101649/04 A RU2014101649/04 A RU 2014101649/04A RU 2014101649 A RU2014101649 A RU 2014101649A RU 2014101649 A RU2014101649 A RU 2014101649A
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carbohydrate
evaporator
ionic liquid
solvent
stage
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RU2014101649/04A
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RU2608609C2 (en
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Алоис КИНДЛЕР
Клеменс Массонне
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Басф Се
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    • 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
    • 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
    • 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
    • C07D307/50—Preparation from natural products

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
  • Saccharide Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

1. Непрерывный способ дегидратации углеводсодержащей композиции, который состоит из:i) образования композиции, состоящей из- как минимум одного углеводсодержащего исходного материала,- как минимум одной ионной жидкости (ИЖ), и- как минимум одного растворителя (HP) с температурой кипения не превышающей 120°С при стандартном давлении (1013 мБар),ii) загрузки композиции согласно стадии i) в испаритель, где она подвергается реакции и выпариванию при температуре в промежутке от 100 до 300°С и давлении, которое не превышает 500 мБар,iii) извлечения из испарителя отработанных газов, которые включают продукты дегидратации, а также извлечения отработанных жидкостей, которые включают как минимум одну ионную жидкость,iv) конденсации отработанных газов с последующим разделением и выделением продуктов дегидратации.2. Способ по п. 1, в котором композиция согласно стадии i) включает в себя углеводсодержащий исходный материал в количестве от 1 до 20 мас.%, особенно предпочтительным является количество от 2 до 15 мас.%, исходя из общей массы композиции.3. Способ по п. 1, в котором углеводсодержащий исходный материал выбирают из моно- и/или олигосахаридов, в частности из моно- и/или дисахаридов.4. Способ по п. 3, в котором моно- и/или олигосахариды выбирают из:- альдопентозы- альдогексозы,- кетогексозы,- дисахаридов, которые являются производными альдопентозы, альдогексозы, кетогексозы и их смесей,- смеси вышеприведенных соединений.5. Способ по п. 3, в котором моно- и/или олигосахариды выбирают из фруктозы, глюкозы, сахарозы, ксилозы и их смесей.6. Способ по п. 1, в котором углеводсодержащий исходный материал выбирают из целлюлозных исходных материалов и лигноц1. A continuous method for the dehydration of a carbohydrate-containing composition, which consists of: i) the formation of a composition consisting of at least one carbohydrate-containing starting material, at least one ionic liquid (IL), and at least one solvent (HP) with a boiling point not exceeding 120 ° C at a standard pressure (1013 mbar), ii) loading the composition according to stage i) into the evaporator, where it is subjected to reaction and evaporation at a temperature in the range from 100 to 300 ° C and a pressure that does not exceed 500 mbar, iii) extract from evaporate I exhaust gases which include dehydration products as well as recovery of waste liquids which comprise at least one ionic liquid, iv) exhaust gas condensation followed by separation and isolation degidratatsii.2 products. The method according to claim 1, wherein the composition according to step i) comprises a carbohydrate-containing starting material in an amount of from 1 to 20 wt.%, Particularly preferred is an amount of from 2 to 15 wt.%, Based on the total weight of the composition. The method according to claim 1, wherein the carbohydrate-containing starting material is selected from mono- and / or oligosaccharides, in particular from mono- and / or disaccharides. The method according to claim 3, in which the mono- and / or oligosaccharides are selected from: - aldopentoses-aldohexoses, - ketohexoses, - disaccharides, which are derivatives of aldopentoses, aldohexoses, ketohexoses and mixtures thereof, - mixtures of the above compounds. The method of claim 3, wherein the mono- and / or oligosaccharides are selected from fructose, glucose, sucrose, xylose, and mixtures thereof. The method of claim 1, wherein the carbohydrate-containing starting material is selected from cellulosic starting materials and ligno

Claims (21)

1. Непрерывный способ дегидратации углеводсодержащей композиции, который состоит из:1. A continuous method for the dehydration of a carbohydrate-containing composition, which consists of: i) образования композиции, состоящей изi) the formation of a composition consisting of - как минимум одного углеводсодержащего исходного материала,- at least one carbohydrate-containing starting material, - как минимум одной ионной жидкости (ИЖ), и- at least one ionic liquid (IL), and - как минимум одного растворителя (HP) с температурой кипения не превышающей 120°С при стандартном давлении (1013 мБар),- at least one solvent (HP) with a boiling point not exceeding 120 ° C at standard pressure (1013 mbar), ii) загрузки композиции согласно стадии i) в испаритель, где она подвергается реакции и выпариванию при температуре в промежутке от 100 до 300°С и давлении, которое не превышает 500 мБар,ii) loading the composition according to step i) into the evaporator, where it is subjected to reaction and evaporation at a temperature in the range from 100 to 300 ° C and a pressure that does not exceed 500 mbar, iii) извлечения из испарителя отработанных газов, которые включают продукты дегидратации, а также извлечения отработанных жидкостей, которые включают как минимум одну ионную жидкость,iii) recovering from the evaporator exhaust gases that include dehydration products, as well as extracting exhaust liquids that include at least one ionic liquid, iv) конденсации отработанных газов с последующим разделением и выделением продуктов дегидратации.iv) condensation of exhaust gases followed by separation and isolation of dehydration products. 2. Способ по п. 1, в котором композиция согласно стадии i) включает в себя углеводсодержащий исходный материал в количестве от 1 до 20 мас.%, особенно предпочтительным является количество от 2 до 15 мас.%, исходя из общей массы композиции.2. The method according to p. 1, in which the composition according to stage i) includes a carbohydrate-containing starting material in an amount of from 1 to 20 wt.%, Particularly preferred is an amount of from 2 to 15 wt.%, Based on the total weight of the composition. 3. Способ по п. 1, в котором углеводсодержащий исходный материал выбирают из моно- и/или олигосахаридов, в частности из моно- и/или дисахаридов.3. The method according to claim 1, wherein the carbohydrate-containing starting material is selected from mono- and / or oligosaccharides, in particular from mono- and / or disaccharides. 4. Способ по п. 3, в котором моно- и/или олигосахариды выбирают из:4. The method according to p. 3, in which mono - and / or oligosaccharides are selected from: - альдопентозы- aldopentoses - альдогексозы,- aldohexoses, - кетогексозы,- ketohexoses, - дисахаридов, которые являются производными альдопентозы, альдогексозы, кетогексозы и их смесей,- disaccharides, which are derivatives of aldopentose, aldohexose, ketohexose and mixtures thereof, - смеси вышеприведенных соединений.- mixtures of the above compounds. 5. Способ по п. 3, в котором моно- и/или олигосахариды выбирают из фруктозы, глюкозы, сахарозы, ксилозы и их смесей.5. The method according to p. 3, in which the mono- and / or oligosaccharides are selected from fructose, glucose, sucrose, xylose and mixtures thereof. 6. Способ по п. 1, в котором углеводсодержащий исходный материал выбирают из целлюлозных исходных материалов и лигноцеллюлозных исходных материалов.6. The method of claim 1, wherein the carbohydrate-containing starting material is selected from cellulosic starting materials and lignocellulosic starting materials. 7. Способ по п. 1, в котором растворитель (HP) выбирают из воды и смеси воды и как минимум одного растворимого в воде органического растворителя.7. The method of claim 1, wherein the solvent (HP) is selected from water and a mixture of water and at least one water soluble organic solvent. 8. Способ по п. 7, в котором в качестве растворителя (HP) используют смесь вода-спирт, предпочтительно смесь вода-метанол.8. The method of claim 7, wherein the solvent (HP) is a water-alcohol mixture, preferably a water-methanol mixture. 9. Способ по п. 1, в котором на стадии i), в качестве растворителя (HP), используют смесь воды и как минимум одного растворимого в воде органического растворителя в массовом соотношении от 10:90 до 90:10, предпочтительно от 25:75 до 75:25, в частности от 40:60 до 60:40.9. The method according to claim 1, wherein in step i), as a solvent (HP), a mixture of water and at least one water-soluble organic solvent is used in a mass ratio of from 10:90 to 90:10, preferably from 25: 75 to 75:25, in particular from 40:60 to 60:40. 10. Способ по п. 1, в котором массовое соотношение ионной жидкости (ИЖ) и растворителя (HP) в углеводсодержащей композиции согласно стадии i) составляет от 99,5:0.5 до 50:50, особенно предпочтительно от 99:1 до 75:25.10. The method according to p. 1, in which the mass ratio of ionic liquid (IL) and solvent (HP) in the carbohydrate-containing composition according to stage i) is from 99.5: 0.5 to 50:50, particularly preferably from 99: 1 to 75: 25. 11. Способ по п. 1, в котором для получения углеводсодержащей композиции согласно стадии i), как минимум одна ионная жидкость (ИЖ) и как минимум один растворитель (HP) вступают в взаимодействие друг с другом сразу после загрузки в испаритель.11. The method according to p. 1, in which to obtain a carbohydrate-containing composition according to stage i), at least one ionic liquid (IL) and at least one solvent (HP) interact with each other immediately after loading into the evaporator. 12. Способ по п. 1, в котором для получения углеводсодержащей композиции согласно стадии i) температура ионной жидкости (ИЖ) составляет как минимум 50°C, предпочтительно как минимум 75°C.12. The method according to p. 1, in which to obtain a carbohydrate-containing composition according to stage i) the temperature of the ionic liquid (IL) is at least 50 ° C, preferably at least 75 ° C. 13. Способ по п. 1, в котором на стадии i):13. The method according to p. 1, in which stage i): i1) как минимум один моносахарид и/или как минимум один олигосахарид растворяют в смеси вода-спирт,i1) at least one monosaccharide and / or at least one oligosaccharide is dissolved in a water-alcohol mixture, i2) раствор, полученный на стадии i1), растворяют в как минимум одной ионной жидкости (ИЖ),i2) the solution obtained in stage i1) is dissolved in at least one ionic liquid (IL), i3) смесь, полученную на стадии i2), затем немедленно загружают в испаритель на стадию ii).i3) the mixture obtained in step i2) is then immediately charged to the evaporator in step ii). 14. Способ по п. 1, в котором на стадии ii), в качестве испарителя, используют испаритель, оперирующий кратковременным пребыванием в нем композиции, предпочтительно используются тонкопленочные испарители, в частности пленочные испарители, оборудованные ракелями.14. The method according to claim 1, in which, in step ii), an evaporator is used as the evaporator, which operates with the composition being in it for a short time, thin-film evaporators are used, in particular film evaporators equipped with squeegees. 15. Способ по п. 1, в котором время нахождения в испарителе, в зависимости от ионной жидкости (ИЖ) составляет от 0,1 с до 2 мин, предпочтительно от 1 с до 1 мин.15. The method according to p. 1, in which the residence time in the evaporator, depending on the ionic liquid (IL) is from 0.1 s to 2 minutes, preferably from 1 s to 1 min. 16. Способ по п. 1, в котором на стадии ii), температура в испарителе составляет от 150°C до 250°C.16. The method according to p. 1, in which in stage ii), the temperature in the evaporator is from 150 ° C to 250 ° C. 17. Способ по п. 1, в котором на стадии ii), давление в испарителе составляет от 250 мБар до 0,1 мБар, предпочтительно от 100 мБар до 1 мБар.17. The method according to claim 1, wherein in step ii), the pressure in the evaporator is from 250 mbar to 0.1 mbar, preferably from 100 mbar to 1 mbar. 18. Способ по п. 1, в котором отработанные газы, выгруженные из испарителя на стадии iii) включают как минимум 75 мас.%, предпочтительно как минимум 90 мас.%, и в частности как минимум 95 мас.% в особенности как минимум 99 мас.% и вплоть до как минимум 99,5 мас.% растворителя (HP), исходя из общего количества растворителя (HP) использованного согласно стадии i).18. The method according to claim 1, wherein the exhaust gases discharged from the evaporator in step iii) comprise at least 75 wt.%, Preferably at least 90 wt.%, And in particular at least 95 wt.%, In particular at least 99 wt.% and up to at least 99.5 wt.% solvent (HP), based on the total amount of solvent (HP) used according to stage i). 19. Способ по п. 1, в котором отработанные жидкости, выгруженные из испарителя на стадии iii), включают как минимум 90 мас.%, предпочтительно как минимум 95 мас.%, и в частности как минимум 99 мас.%, и вплоть до как минимум 99,5 мас.% ионной жидкости (ИЖ), исходя из общего количества ионной жидкости использованной согласно стадии i).19. The method according to claim 1, wherein the spent liquids discharged from the evaporator in step iii) comprise at least 90 wt.%, Preferably at least 95 wt.%, And in particular at least 99 wt.%, And up to at least 99.5 wt.% ionic liquid (IL), based on the total amount of ionic liquid used according to stage i). 20. Способ по п. 1, в котором отработанные жидкости, выгруженные из испарителя на стадии iii), включают не более 5 мас.% воды, предпочтительно не больше 1 мас.% и в частности не более 0,5 мас.% воды, исходя из общей массы отработанных жидкостей.20. The method according to claim 1, in which the spent liquids discharged from the evaporator in step iii) comprise not more than 5 wt.% Water, preferably not more than 1 wt.% And in particular not more than 0.5 wt.% Water, based on the total mass of waste fluids. 21. Способ по любому из пп. 1-20, в котором получают21. The method according to any one of paragraphs. 1-20, in which - 5-гидроксиметилфурфурол из фруктозы или,- 5-hydroxymethylfurfural from fructose or, - 5-гидроксиметилфурфурол из сахарозы или,- 5-hydroxymethylfurfural from sucrose or, - фурфурол из ксилозы. - furfural from xylose.
RU2014101649A 2011-06-22 2012-06-21 Method of dehydrating carbohydrate-containing compositions RU2608609C2 (en)

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