WO2012038967A1 - Procédé de conversion du saccharose en 5-hmf à l'aide d'un catalyseur de silice poreux contenant un lanthane - Google Patents

Procédé de conversion du saccharose en 5-hmf à l'aide d'un catalyseur de silice poreux contenant un lanthane Download PDF

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Publication number
WO2012038967A1
WO2012038967A1 PCT/IN2010/000834 IN2010000834W WO2012038967A1 WO 2012038967 A1 WO2012038967 A1 WO 2012038967A1 IN 2010000834 W IN2010000834 W IN 2010000834W WO 2012038967 A1 WO2012038967 A1 WO 2012038967A1
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Prior art keywords
sucrose
hydroxymethylfurfural
catalyst
production
mixture
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Application number
PCT/IN2010/000834
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English (en)
Inventor
Ganapati Dadasaheb Yadav
Rajesh Vishnudev Sharma
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Ganapati Dadasaheb Yadav
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Application filed by Ganapati Dadasaheb Yadav filed Critical Ganapati Dadasaheb Yadav
Priority claimed from IN2442MU2010 external-priority patent/IN268182B/en
Publication of WO2012038967A1 publication Critical patent/WO2012038967A1/fr

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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
    • C07D307/42—Singly bound oxygen atoms
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • This invention related to method for producing 5-hydroxymethyl furfural consisting of reacting sucrose solution with the heterogeneous solid acid ICaT-2 catalyst. All the operations are carried out in batch reactor. In this method mixture of solvents are used to produce 5-hydroxymethyl furfural. The kinetic parameter study revealed that sucrose conversion and 5-hydroxymethyl furfural yield are increased with increasing temperature and amount of catalyst. Catalyst is recycled many times without ' loss of its activity. Isolation procedure for 5-hydroxymethyl furfural is also discussed. BACKGROUND OF THE INVENTION
  • HMF 5-hydroxymethyl furfural
  • renewable resources act as key intermediate compound that bridge the gap between industrial chemistry because of the wide range of the chemical intermediates and end products is produced from these compounds which used in the polymer industry, fuel and pharmaceutical industries.
  • HMF possesses a high potential industrial demand, and is reviewed as a sleeping giant to produce intermediate chemical from bio based renewable resources.
  • HMF is versatile chemical compound; however, no technical process has been constructed through sugar route till now. The reasons are low selectivity to HMF, requirement of strong acids, which require neutralization and lead to large amount of acid waste.
  • the high boiling polar solvents like dimethylsulfoxide, dimethylformamide, acetonitrile, poly(glycol ether) etc. give good selectivity to HMF but makes separation process more expensive.
  • US 4590283A disclose the process for manufacturing 5 -hydroxymethy furfural from hexose by heterogeneous catalyst comprising of strong acid cation exchange resin. This process is carried out continuously, particularly by the countercurrent principle. Strongly polar aprotic solvent such as dimethylsulfoxide, dimethylformamide, N- methylpyrrolidone, are used, this makes poduct isolation tedious and costly.
  • US 142599A1 disclose the process for preparation and purification of 5- hydroxymethy furfural.
  • high fructose corn syrup is used as convenient fructose source and 5 -hydroxymethylfurfural is prepared by using ion exchange resin in presence of l-methyl-2-pyrrolidinone, dimethylacetamide, dimethylformamide and combinations.
  • US 033187A1 disclose the process for converting carbohydrate to 5- hydroxymethylfurfural in the presence of metal halide and acid catalyst. In this process ionic liquids are used as solvent to dissolve carbohydrates.
  • US 033188 A 1 disclose the process for converting sugars to furan derivatives by using a biphasic reactor containing reactive aqueous phase and an organic extracting phase.
  • the aqueous reaction solution contains an acid catalyst.
  • Both aqueous solution and organic extraction solution contain at least one modifier such as dimethylsulfoxide, dimethylformamide, N-methylpyrrolidinone, acetonitrile, butyrolactone, dioxane and pyrrolidinone.
  • US 156841 Al disclose a method of producing substantially pure HMF, HMF esters and other derivatives from carbohydrate source.
  • Carbohydrate solution containing organic acid is heated and continuously flowed through a solid phase catalyst to form HMF or/and HMF ester.
  • HMF ester is isolated from the product mixture by the process selected from the group consisting of filtration, evaporation, extraction and distillation.
  • US 313889A1 disclose the process for making hydroxymethylfurfural from saccharide.
  • a metal complex of an N-heterocyclic carbene and ionic liquid is used.
  • Reaction mixture contains solvent immiscible with ionic liquid to extract 5 -hydroxymethylfurfural from ionic liquid.
  • WO 012445A1 disclose a method of producing HMF by mixing or agitating an aqueous solution of fructose and inorganic acid catalyst with water immiscible organic solvent to form an emulsion. The mixture is heated to 240 °C to 270 °C in a flow reactor at high pressure and then separated into aqueous and organic phase to obtain HMF.
  • HMF 5- hydroxymethylfurfural
  • 5-hydroxymethylfurfural is produce by dehydration of fructose and glucose using a biphasic reactor system, comprised of reactive aqueous phase modified with DMSO, combined with an organic extracting phase consisting of a 7:3 (w/w) MIBK-2-butanol mixture or dichloromethane by using mineral acid catalyst such as HC1, H 2 S0 4 , H 3 P0 4 .
  • mineral acid catalyst such as HC1, H 2 S0 4 , H 3 P0 4 .
  • the dehydration of sucrose to HMF was carried out by using mineral acids (such as HC1, H 3 P0 4 , H 2 S0 4 ), ion exchange resins, zeolites, transition metal ions and solid metal phosphates.
  • Mineral acid catalysts are give high sucrose conversion with low selectivity to HMF yield and major disadvantage is corrosion of reactor, separation of the product and large amount of acid waste.
  • Solid acid catalysts such as H-zeolite and metal phosphates (niobium phosphate) give low conversion and low selectivity.
  • niobium phosphate metal phosphates
  • This invention deals with to replace the mineral acid catalysts by stable, recyclable, nontoxic solid acid catalyst.
  • This invention discloses a method for producing 5- hydroxymethylfurfural from sucrose by using reusable ICaT-2 catalyst. Reactions are carried out in batch reactor by using mixture of solvents.
  • This invention is directed to a method for the production of 5-hydroxymethylfurfural from sucrose in the highest possible concentration and with minimum production cost.
  • Another objective of the present invention is to develop method for production of 5- hydroxymethylfurfural which utilizes batch mode reactor.
  • Another objective of the present invention is dehydrating the feedstock solution comprising of sucrose in the presence ICaT-2 catalyst by using mixed solvent system to yield 5-hydroxymethylfurfural in good yield.
  • Another objective of the present invention is to utilize minimum quantity of heterogeneous reusable solid acid catalyst to produce 5-hydroxymethylfurfural from sucrose.
  • Yet another objective of the present invention is to develop method for production of 5- hydroxymethylfurfural which utilizes mixture of various solvents to increase the product selectivity and reduces production cost.
  • Another objective of the present invention is to develop method for preparation of 5- hydroxymethylfurfural from sucrose, which utilizes minimum energy and gives minimum waste.
  • ICaT-2 catalyst is heterogeneous solid acid catalyst. It comprises of rare earth metals in the form of trifluromethane sulfonate anchored with organic-inorganic porous silica as base metal through organic linkage. This method has been developed for batch mode ⁇ reactor system. 5-hydroxymethylfurfural is isolated from reaction mass by extraction followed by distillation.
  • the method for production of 5-hydroxymethylfurfural from sucrose are performed in batch mode operation.
  • heterogeneous solid acid catalyst ICaT-2 is comprises of metal sulfonate anchored with hexagonal organic-inorganic mesoporous silica through organic linkage are used.
  • the method for production of 5-hydroxymethylfurfural from sucrose has 0.1% to 50% wt/wt percentage of ICaT-2 catalyst based on reaction mass.
  • solvent used is selected from the group of solvents such as water, methanol, ethanol, propanol, butanol, acetone, acetonitrile, dimethyl formamide, dimethyl sulfoxide, N-methyl pyrrolidone and/or mixture thereof.
  • solvent used are more preferably the mixture of water: methanol, water: ethanol, water: propanol, water: acetone and water :acetonitrile and/or mixture thereof.
  • the method for production of 5-hydroxymethylfurfural from sucrose has been carried out in the temperature range 10 °C to 300 °C, more preferably in the range of 100 °C to 250
  • the method for production of 5-hydroxymethylfurfural from sucrose wherein autogeneous pressure or external pressure of the reaction are in the range of 2 bar to 30 bar.
  • the method for production of 5-hydroxymethylfurfural from sucrose, wherein separation of the pure 5-hydroxymethylfurfural from final reaction mixture is carried out by extraction with organic solvent such ethyl acetate, ethers, dichloromethane or methyl- tertiary-butyl ether and/or mixture thereof followed by vacuum distillation.
  • organic solvent such ethyl acetate, ethers, dichloromethane or methyl- tertiary-butyl ether and/or mixture thereof followed by vacuum distillation.
  • ICaT-2 Institute of Chemical Technology
  • ICaT-2 catalyst is comprises of rare earth metals in the form of trifluromethane sulfonate anchored with organic- inorganic porous silica as base metal through organic linkage.
  • the present invention utilizes ICaT-2 which is easily generable and shows excellent reusability for 5-hyroxymethylfurfural process.
  • the ICaT-2 catalyst composition has specific surface area in the range of 50 m 2 /g to 1000 m 2 /g and pore diameter in the range of 20-100 A.
  • sucrose is dehydrated under mild conditions by using ICaT-2 as catalyst and mixture of solvents.
  • 5 -Hydroxymethy furfural is the bio- based renewable chemical and act as key intermediate compound that bridge the gap between industrial chemistry because of the wide range of the chemical intermediates and end products that can be produced from these compounds for use in the polymer industry, fuel and pharmaceutical industries.
  • the reaction mechanism is as follows:
  • sucrose dehydration is carried out in the presence of solvent selected from the group of solvent such as water, methanol, ethandl, propanol, butanol, acetone, acetonitrile, dimethyl formamide, dimethyl sulfoxide and/or mixture thereof.
  • solvent selected from the group of solvent such as water, methanol, ethandl, propanol, butanol, acetone, acetonitrile, dimethyl formamide, dimethyl sulfoxide and/or mixture thereof.
  • solvent used for reaction is the mixture of aqueous and organic solvent.
  • Organic solvents used are such as methanol, ethanol, propanol, acetonitrile, dimethyl formamide, dimethyl sulfoxide and acetone in the range of 10 to 99 %.
  • the amount of catalyst employed is typically about 0.1 to 50% based on weight of the sucrose in the reaction mixture.
  • the used catalyst is recycled several times to check process feasibility for industrial utilization.
  • One of the embodiments of the present invention for 5-hydroxymethylfurfural production wherein sucrose is charged in the range of 0.1%) to 50 % wt/wt of the reaction mass.
  • One of the embodiments of the present invention for method of 5-hydroxymethylfurfural production wherein reaction is carried out in the temperature range of 50 °C to 300 °C, preferably in the range of 100 to 250 °C.
  • Another aspect of the present invention for method of manufacturing 5- hydroxymethylfurfural is that dehydration of sucrose to 5-hydroxymethylfurfural is carried out for the time 1 min to 10 hours, preferably for 30 min to 5 hours depending upon the type of solvent and amount of catalyst used.
  • reaction is monitor on HPLC by using RI detector and ultraviolet (UV) detector both.
  • Another aspect of the present invention is the product 5-hydroxymethylfurfural is separated from reaction mixture by extraction and simple distillation technique. Therefore, the foregoing examples are considered as illustrative in terms of principles of the invention.
  • ICaT-2 was prepared by a co-condensation sol-gel route. Hexadecyl amine was dissolved in ethanol and water mixture. Mixture of tetraethyl orthosilicate and 3- (mercaptopropyl)trimethoxysilane were added to the above solution. Resulting material is oxidized. Further it is treated with lanthanum chloride (400 mg) in acetonitrile for 2 h. The slurry was filtered and treated with trifluromethanesulfonic acid (5.4 mmol) at 30 °C for 2 h. The slurry was filtered and washed with water and dried under vacuum to get the active ICaT-2 catalyst.
  • Autoclave reactor is purged with nitrogen and loaded with sucrose (0.0125 mol), 100 ml mixture of solvents (acetone : water 7:3) and reaction temperature is 160 °C.
  • sucrose 0.0125 mol
  • 100 ml mixture of solvents acetone : water 7:3
  • reaction temperature 160 °C.
  • the experiments are carried out in a 300 cm 3 stainless steel Parr autoclave. A four bladed pitch turbine impeller was used for agitation. The temperature + 1 °C of the desired value is maintained at by PID controller.
  • UV and RI detector are utilized for quantitative analysis of the samples after specific time intervals. Calibration curve method is adopted for calculation of percentage conversion and percentage yield. The reusability of the catalyst is tested by conducting four runs. After completion of the reaction, the catalyst is filtered and washed with acetone.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)

Abstract

Cette invention concerne un procédé de production de 5-hydroxyméthylfurfural à partir de saccharose à l'aide d'un catalyseur acide solide hétérogène, ICaT-2, en présence d'un mélange de solvants. L'étude des paramètres cinétiques a révélé que la conversion du saccharose et le rendement de 5-hydroxyméthylfurfural sont augmentés avec une température et une quantité de catalyseur croissantes. Une conversion de saccharose de 73 % et un rendement de 5-hydroxyméthylfurfural de 58 % sont obtenus après 60 min à 180°C. Les réactions sont mises en œuvre en mode discontinu. Le catalyseur est recyclé de nombreuses fois sans perte de son activité. Un procédé d'isolation du 5-hydroxyméthylfurfural est également décrit. L'ICaT-2 est préparé par une voie de co-condensation sol-gel. Une hexadécylamine est dissoute dans un mélange d'éthanol et d'eau. Un mélange d'orthosilicate de tétraéthyle et de 3-(mercaptopropyl)triméthoxysilane est ajouté à la solution ci-dessus. Le mélange obtenu est traité avec du chlorure de lanthane (400 mg) pendant 2 h. La suspension épaisse est filtrée et traitée avec de l'acide trifluorométhanesulfonique (5,4 mmol) à 30°C pendant 2 h. Elle est ensuite filtrée et lavée à l'eau, puis séchée sous vide pour obtenir le catalyseur ICaT-2 actif.
PCT/IN2010/000834 2010-09-03 2010-12-21 Procédé de conversion du saccharose en 5-hmf à l'aide d'un catalyseur de silice poreux contenant un lanthane WO2012038967A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN2442/MUM/2010 2010-09-03
IN2950/MUM/2010 2010-10-25
IN2950MU2010 2010-10-25
IN2442MU2010 IN268182B (fr) 2010-09-03 2011-02-18

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2703395A1 (fr) * 2012-09-03 2014-03-05 Annikki GmbH Procédé de production de dérivés de furanne
CN106632164A (zh) * 2016-12-29 2017-05-10 江南大学 一种磁性金属氧化物交联酸性聚离子液体的制备及其应用
CN114957173A (zh) * 2022-05-12 2022-08-30 浙江恒逸石化研究院有限公司 一种固体酸催化高浓度生物质糖连续转化与分离5-羟甲基糠醛的方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4590283A (en) 1983-09-14 1986-05-20 Roquette Freres Process for manufacturing 5-hydroxymethylfurfural
US20060142599A1 (en) 2004-12-10 2006-06-29 Sanborn Alexandra J Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives
US20080033187A1 (en) 2006-08-07 2008-02-07 Haibo Zhao Methods for conversion of carbohydrates in ionic liquids to value-added chemicals
US20080033188A1 (en) 2006-06-06 2008-02-07 Dumesic James A Catalytic process for producing furan derivatives in a biphasic reactor
WO2009010244A1 (fr) 2007-07-14 2009-01-22 Schepers Gmbh + Co. Kg Procédé de fonctionnement d'un dispositif de gravure laser
US20090156841A1 (en) 2007-12-12 2009-06-18 Sanborn Alexandra J Conversion of carbohydrates to hydroxymethylfurfural (hmf) and derivatives
DE102008009933A1 (de) * 2008-02-18 2009-08-20 Friedrich-Schiller-Universität Jena Verfahren zur Herstellung von 5-Hydroxymethylfurfural mit Hilfe von ionischen Flüssigkeiten
US20090313889A1 (en) 2008-06-18 2009-12-24 Agency For Science, Technology And Research Production of hydroxymethylfurfural
IN2010MU02442A (fr) * 2010-09-03 2010-10-22 Ganapati Dadasaheb Yadav

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4590283A (en) 1983-09-14 1986-05-20 Roquette Freres Process for manufacturing 5-hydroxymethylfurfural
US20060142599A1 (en) 2004-12-10 2006-06-29 Sanborn Alexandra J Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives
US20080033188A1 (en) 2006-06-06 2008-02-07 Dumesic James A Catalytic process for producing furan derivatives in a biphasic reactor
US20080033187A1 (en) 2006-08-07 2008-02-07 Haibo Zhao Methods for conversion of carbohydrates in ionic liquids to value-added chemicals
WO2009010244A1 (fr) 2007-07-14 2009-01-22 Schepers Gmbh + Co. Kg Procédé de fonctionnement d'un dispositif de gravure laser
US20090156841A1 (en) 2007-12-12 2009-06-18 Sanborn Alexandra J Conversion of carbohydrates to hydroxymethylfurfural (hmf) and derivatives
DE102008009933A1 (de) * 2008-02-18 2009-08-20 Friedrich-Schiller-Universität Jena Verfahren zur Herstellung von 5-Hydroxymethylfurfural mit Hilfe von ionischen Flüssigkeiten
US20090313889A1 (en) 2008-06-18 2009-12-24 Agency For Science, Technology And Research Production of hydroxymethylfurfural
IN2010MU02442A (fr) * 2010-09-03 2010-10-22 Ganapati Dadasaheb Yadav

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
APPLIED CATALYSIS A: GENERAL, vol. 183, 1999, pages 295 - 302
CHHEDA ET AL: "An overview of dehydration, aldol-condensation and hydrogenation processes for production of liquid alkanes from biomass-derived carbohydrates", CATALYSIS TODAY, vol. 123, no. 1-4, 19 May 2007 (2007-05-19), ELSEVIER, NL, pages 59 - 70, XP022085575, ISSN: 0920-5861, DOI: 10.1016/J.CATTOD.2006.12.006 *
GREEN CHEMISTRY, vol. 9, 2007, pages 342 - 350
JOURNAL OF CHEMICAL SOCIETY (RESUMED), 1960, pages 787 - 791
JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 253, 2006, pages 165 - 169
SPECIALITY PETROCHEMICALS, vol. 25, 2008, pages 19 - 22

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2703395A1 (fr) * 2012-09-03 2014-03-05 Annikki GmbH Procédé de production de dérivés de furanne
WO2014033289A1 (fr) * 2012-09-03 2014-03-06 Annikki Gmbh Procédé pour la production de dérivés de furane
JP2015526494A (ja) * 2012-09-03 2015-09-10 アニッキ ゲーエムベーハーＡｎｎｉｋｋｉ Ｇｍｂｈ フラン誘導体の製造方法
AU2013310894B2 (en) * 2012-09-03 2017-09-07 Annikki Gmbh Process for the production of furan derivatives
CN106632164A (zh) * 2016-12-29 2017-05-10 江南大学 一种磁性金属氧化物交联酸性聚离子液体的制备及其应用
CN114957173A (zh) * 2022-05-12 2022-08-30 浙江恒逸石化研究院有限公司 一种固体酸催化高浓度生物质糖连续转化与分离5-羟甲基糠醛的方法
CN114957173B (zh) * 2022-05-12 2024-04-05 浙江恒逸石化研究院有限公司 一种固体酸催化高浓度生物质糖连续转化与分离5-羟甲基糠醛的方法

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