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WO2019039705A1 - Procédé pour la séparation de 5-hydroxyméthyl-2-furfural et de diméthylsulfoxyde dans un processus de préparation de 5-hydroxyméthyl-2-furfural - Google Patents

Procédé pour la séparation de 5-hydroxyméthyl-2-furfural et de diméthylsulfoxyde dans un processus de préparation de 5-hydroxyméthyl-2-furfural Download PDF

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Publication number
WO2019039705A1
WO2019039705A1 PCT/KR2018/005976 KR2018005976W WO2019039705A1 WO 2019039705 A1 WO2019039705 A1 WO 2019039705A1 KR 2018005976 W KR2018005976 W KR 2018005976W WO 2019039705 A1 WO2019039705 A1 WO 2019039705A1
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Prior art keywords
organic solvent
hmf
hydrocarbon compound
dmso
layer
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PCT/KR2018/005976
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English (en)
Korean (ko)
Inventor
조진구
김용진
박석규
이용진
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SK Chemicals Co Ltd
Korea Institute of Industrial Technology KITECH
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SK Chemicals Co Ltd
Korea Institute of Industrial Technology KITECH
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Publication of WO2019039705A1 publication Critical patent/WO2019039705A1/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
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/06—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/04—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to a process for the separation of 5-hydroxymethyl-2-furfural and dimethylsulfoxide in the process for the production of 5-hydroxymethyl-2-furfural.
  • 2,5-furan dicarboxylic acid which is a biomass-derived compound
  • TPA terephthalic acid
  • PET polyethylene terephthalate
  • the biggest obstacle to the use of 2,5-furan dicarboxylic acid in PET production is the formation of 5-Hydroxymethyl-2-furfural, a precursor of 2,5-furan dicarboxylic acid , HMF).
  • the 2,5-furan dicarboxylic acid can be converted via an oxidation process of 5-hydroxymethyl-2-furfural.
  • an effective and economical method is to convert fructose obtained from carbohydrate-based biomass into ion exchange resin catalysts in a dimethylsulfoxide (DMSO) To obtain 5-hydroxymethyl-2-furfural.
  • DMSO dimethylsulfoxide
  • dimethylsulfoxide has a high boiling point, it is difficult to separate through distillation, and it is difficult to recover 5-hydroxymethyl-2-furfural in a dimethylsulfoxide solvent because it is mixed with most of the solvents.
  • An object of the present invention to solve the above problems is to provide a separation method for efficiently separating dimethylsulfoxide and 5-hydroxymethyl-2-furfural from a mixture of 5-hydroxymethyl-2-furfural and dimethylsulfoxide .
  • Another object of the present invention is to provide a process for the production of 5-hydroxymethyl-2-furfural using a dimethylsulfoxide solvent, which can effectively separate the dimethylsulfoxide solvent and 5-hydroxymethyl-2-furfural To provide a separation method.
  • a pharmaceutical composition comprising (a) 5-hydroxymethyl-2-furfural (HMF) and dimethyl sulfoxide (DMSO) Preparing a mixed solution;
  • the organic solvent comprises a first organic solvent comprising an aprotic nonpolar organic solvent and a second organic solvent comprising an aprotic polar organic solvent
  • the separation method may further include (c) after step (b), separating the aqueous solution layer from the layer separation solution to obtain the organic layer.
  • the separation method may further include (d) after step (c), removing the organic solvent from the organic layer to obtain the HMF.
  • the first organic solvent may have a dipole moment D of 0 or more and less than 1.0D (0 ⁇ dipole moment < 1.0).
  • the first organic solvent may have a dipole moment D of 0.05 to 0.5D (0.05 dipole moment? 0.5).
  • the first organic solvent may have a solubility in H 2 O (g / 100 g) of 0 to 0.2.
  • the first organic solvent may be at least one selected from the group consisting of an aliphatic hydrocarbon compound, an alicyclic hydrocarbon compound, and an aromatic hydrocarbon compound.
  • the aliphatic hydrocarbon compound may be at least one selected from the group consisting of pentane, hexane (HX) and heptane,
  • alicyclic hydrocarbon compound is at least one selected from the group consisting of cyclopentane and cyclohexane
  • the aromatic hydrocarbon compound may be at least one selected from the group consisting of benzene, toluene (TOL) and xylene.
  • the second organic solvent may have a dipole moment (D) of 1 to 3 D.
  • the second organic solvent may have a dipole moment (D) of 1.5 to 3 D.
  • the second organic solvent may have a solubility in H 2 O (g / 100 g) of 0 to 10.0.
  • the second organic solvent may be at least one selected from the group consisting of a halogen-based hydrocarbon compound, an ester-based hydrocarbon compound, a ketone-based hydrocarbon compound, and an ether-based hydrocarbon compound.
  • the halogen-based hydrocarbon compound is at least one selected from the group consisting of chloroform (CF), dichloromethane (DCM) and 1,2-dichloroethane (DCE)
  • ester-based hydrocarbon compound is at least one selected from the group consisting of ethyl acetate (EA), methyl acetate and ethyl benzoate,
  • ketone-based hydrocarbon compound is at least one selected from the group consisting of methyl isobutyl ketone (MIBK) and 3-pentanone,
  • the ether-based hydrocarbon compound may be at least one selected from the group consisting of diethyl ether (DEE) and methyltit-butyl ether (MTBE).
  • DEE diethyl ether
  • MTBE methyltit-butyl ether
  • the organic solvent may have a volume ratio of the first organic solvent to the second organic solvent of 0.1: 9.9 to 5.0: 5.0 (v: v).
  • the organic solvent may have a volume ratio of the first organic solvent and the second organic solvent of 0.3: 9.7 to 3.0: 7.0 (v: v).
  • the organic solvent may have a volume ratio of the first organic solvent to the second organic solvent of 0.5: 9.5 to 1.5: 8.5 (v: v).
  • the organic solvent and water may also have a volume ratio of 5: 5 to 9: 1 (v: v).
  • the volume ratio of the mixed solution and the organic solvent may be 1: 1 to 1:10 (v: v).
  • step (a) may be a step of preparing the mixed solution by preparing the HMF by using an anion exchange resin and a cation exchange resin in the DMSO solvent.
  • step (a) may be a step of preparing the mixed solution by preparing the HMF using a cation exchange resin in the DMSO solvent.
  • the present invention can provide a separation method that effectively separates dimethylsulfoxide and 5-hydroxymethyl-2-furfural in a mixture of 5-hydroxymethyl-2-furfural and dimethylsulfoxide.
  • the present invention also relates to a process for the production of 5-hydroxymethyl-2-furfural using a dimethylsulfoxide solvent. After completion of the reaction, a step of separating the dimethylsulfoxide solvent and 5-hydroxymethyl-2-furfural Method can be provided.
  • FIG. 1 is a diagram showing a process of separating HMF prepared from a hexane-containing compound under DMSO solvent from DMSO using a mixed extraction vessel solvent as a schematic diagram of the present invention.
  • FIG. 2 is a correction graph showing the correlation between the HMF / DMSO region ratio and the HMF / DMSO molar ratio, which are used to obtain HMF and DMSO present in the water layer and the organic layer, respectively.
  • first, second, etc. can be used to describe various elements, but the constituent elements are not limited by the terms. The terms are used only for the purpose of distinguishing one component from another.
  • first component may be referred to as a second component, and similarly, the second component may also be referred to as a first component.
  • a process for preparing a mixed solution comprising (a) 5-hydroxymethyl-2-furfural (HMF) and dimethyl sulfoxide (DMSO) ; And (b) mixing an organic solvent and water with the mixed solution to prepare a layer separation solution layered with an aqueous solution layer containing DMSO and an organic layer containing HMF;
  • the organic solvent comprises a first organic solvent comprising an aprotic nonpolar organic solvent and a second organic solvent comprising an aprotic polar organic solvent
  • step (a) may be a step of preparing the mixed solution by preparing the HMF by using an anion exchange resin and a cation exchange resin in the DMSO solvent.
  • step (a) may be a step of preparing the mixed solution by preparing the HMF using a cation exchange resin in the DMSO solvent.
  • aldose-type hexadecane compound &quot means aldose, a monosaccharide containing one aldehyde per mole, and means a sugar having six carbons.
  • the aldose-type hexacarbonyl compound may be an aldose-type glucose, an aldose-type galactose, a sugar compound including an aldose-type glucose or an aldose-type galactose.
  • &quot 5-hydroxymethyl-2-furfural (HMF) " used in the present invention means a monosaccharide containing one ketone per mole of the ketose-type hexacosaccharide compound.
  • ketose and aldose can be classified according to the position of the carbonyl group as shown in the following Chemical Formula 1, wherein ketose is a ketone compound in which a carbonyl group exists at the C2 position, and aldose is an aldehyde compound in which a carbonyl group exists at the C1 position.
  • the hexacyano compound exists in an equilibrium relationship between the linear structure and the ring structure according to the pH condition.
  • the ketose has a pentagonal ring structure as shown in Formula 1, and aldose is a hexagonal ring Structure.
  • the anion exchange resin is a polystyrene-based bead-like resin having a quaternary ammonium or tertiary amine functional group at the terminal thereof, and the counter ion is substituted with bicarbonate or aluminate, .
  • the anion exchange resin should be thoroughly washed with saturated sodium bicarbonate or saturated sodium aluminate before use.
  • the cation exchange resin is a polystyrene-based bead-like resin having a sulfonic acid functional group at the terminal, and the counter ion is substituted with a proton to have strong acidity.
  • the cation exchange resin should be thoroughly washed with aqueous hydrochloric acid solution before use.
  • the separation method may further include (c) after step (b), separating the aqueous solution layer from the layer separation solution to obtain the organic layer.
  • the separation method may further include (d) after step (c), removing the organic solvent from the organic layer to obtain the HMF.
  • the first organic solvent may have a dipole moment D of 0 or more and less than 1.0 D (0 dipole moment ⁇ 1.0), preferably 0.05 to 0.5 D (0.5 dipole moment? 0.5) .
  • the dipole moment of the first organic solvent is 1.0D or more, DMSO can not migrate to the organic solvent layer, which is not preferable.
  • the first organic solvent may have a solubility in H 2 O (g / 100 g) of 0 to 0.2. If the solubility of the first organic solvent in water is more than 0.2, it is not preferable because DMSO can migrate to the organic solvent layer.
  • the first organic solvent may be a hydrocarbon-based aliphatic compound such as pentane, hexane (HX) or heptane, a hydrocarbon-based alicyclic compound such as cyclopentane or cyclohexane, a hydrocarbon such as benzene, toluene (TOL) And aromatic compounds of the above-mentioned type.
  • a hydrocarbon-based aliphatic compound such as pentane, hexane (HX) or heptane
  • a hydrocarbon-based alicyclic compound such as cyclopentane or cyclohexane
  • a hydrocarbon such as benzene, toluene (TOL)
  • aromatic compounds of the above-mentioned type such as benzene, toluene (TOL)
  • the second organic solvent may have a dipole moment (D) of 1 to 3, preferably 1.5 to 3. If the dipole moment of the second organic solvent is less than 1.0D, HMF can not be efficiently extracted into the organic layer, which is undesirable. If the molecular weight exceeds 3 D, DMSO can not be transferred to the organic layer.
  • D dipole moment
  • the second organic solvent may have a solubility in H 2 O (g / 100 g) of 0 to 10.0.
  • solubility of the second organic solvent in water is more than 10.0, it is not preferable because the effective phase separation is not performed and the extraction efficiency for HMF is lowered.
  • the second organic solvent may be a halogen-based compound such as chloroform (CF), dichloromethane (DCM) or 1,2-dichloroethane (DCE), an ester such as ethyl acetate (EA), methyl acetate, ethyl benzoate Based compounds such as methyl isobutyl ketone (MIBK) and 3-pentanone, and ether compounds such as diethyl ether (DEE) and methyl tert-butyl ether (MTBE) .
  • CF chloroform
  • DCM dichloromethane
  • DCE 1,2-dichloroethane
  • EA ethyl acetate
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • ether compounds such as diethyl ether (DEE) and methyl tert-butyl ether (MTBE) .
  • the organic solvent may have a volume ratio of the first organic solvent to the second organic solvent of 0.1: 9.9 to 5.0: 5.0 (v: v), preferably 0.3: 9.7 to 3.0: 7.0 (v: v) And preferably 0.5: 9.5 to 1.5: 8.5 (v: v). If the volume ratio is less than 0.1: 9.9, DMSO can not be transferred to the organic layer, and if it is more than 5.0: 5.0, HMF can not be efficiently extracted.
  • the organic solvent and water may also have a volume ratio of 5: 5 to 9: 1 (v: v). If the volume ratio is less than 5: 5, HMF can not be efficiently extracted, which is undesirable. When the volume ratio is more than 9: 1, DMSO can not migrate to the organic layer.
  • the volume ratio of the mixed solution and the organic solvent may be 1: 1 to 1:10 (v: v). If the volume ratio is less than 1: 1, it is not preferable because effective phase separation can not be achieved. If the volume ratio is more than 1:10, it is not preferable because of an increase in the cost of the extraction process.
  • a screening operation was performed to compare the performance of the extraction vessel solvent for separating HMF and DMSO.
  • a standard solution having a molar ratio of DMSO: HMF of 80:20 was prepared and used for screening.
  • the organic layer and water layer were used in a volume ratio of 5 times the standard solution.
  • the molar ratios of HMF and DMSO present in the organic layer and the water layer were obtained by converting the ratio of the area represented by HPLC to the molar ratio using the ratio of HMF and DMSO in FIG. 2.
  • Example 1 The procedure of Example 1 was repeated except that ethyl acetate (EA) was added instead of dichloromethane (DCM).
  • EA ethyl acetate
  • DCM dichloromethane
  • MIBK methyl isobutyl ketone
  • Example 1 The procedure of Example 1 was repeated except that toluene (TOL) was added instead of dichloromethane (DCM).
  • TOL toluene
  • DCM dichloromethane
  • MIBK methyl isobutyl ketone
  • HX hexane
  • the organic layer (upper layer) containing 5-hydroxymethyl-2-furfural was separated to obtain a water layer (lower layer) containing dimethylsulfoxide.
  • the water layer was separated from the organic layer, and the amounts of DMSO and HMF present in each layer were measured by HPLC analysis.
  • the water layer was further extracted with 5 ml of fresh extraction solvent (2.5 ml each of ethyl acetate and hexane), and the amount of DMSO and HMF present in each layer was measured by HPLC analysis for each extraction. The results are shown in Table 3.
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • MIBK Methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • MIBK methyl isobutyl ketone
  • HMF As shown in Table 1, the extraction performance of HMF was good, but MMSK, DEE, EA, DCM, and DCE were extracted with a considerable amount of DMSO, and HX was not extracted into the organic layer of DXO, I did not. In addition, MTBE does not have excellent extraction performance, but DMSO is not extracted into organic layer. HMF extraction was repeated three times using MTBE as an extraction solvent in the screening solvent. HMF with 94% purity was obtained at 80% recovery after three times of repeated extraction.
  • the present invention can provide a separation method that effectively separates dimethylsulfoxide and 5-hydroxymethyl-2-furfural in a mixture of 5-hydroxymethyl-2-furfural and dimethylsulfoxide.
  • the present invention also relates to a process for the production of 5-hydroxymethyl-2-furfural using a dimethylsulfoxide solvent. After completion of the reaction, a step of separating the dimethylsulfoxide solvent and 5-hydroxymethyl-2-furfural Method can be provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé pour la séparation de 5-hydroxyméthyl-2-furfural (HMF) et de diméthylsulfoxyde (DMSO), le procédé comprenant les étapes consistant à : (a) préparer une solution de mélange comprenant du HMF et du DMSO ; et (b) mélanger un solvant organique et de l'eau avec la solution de mélange pour préparer une solution de séparation de couches dans laquelle une couche aqueuse comprenant le DMSO et une couche organique comprenant le HMF sont séparées par séparation de couches, le solvant organique comprenant un premier solvant organique comprenant un solvant organique non polaire aprotique et un second solvant organique comprenant un solvant organique polaire aprotique. Selon la présente invention, un solvant diméthylsulfoxyde et du 5-hydroxyméthyl-2-furfural peuvent être efficacement séparés une fois terminée une réaction de préparation de 5-hydroxyméthyl-2-furfural utilisant un solvant diméthylsulfoxyde .
PCT/KR2018/005976 2017-08-21 2018-05-25 Procédé pour la séparation de 5-hydroxyméthyl-2-furfural et de diméthylsulfoxyde dans un processus de préparation de 5-hydroxyméthyl-2-furfural Ceased WO2019039705A1 (fr)

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KR1020170105619A KR101919311B1 (ko) 2017-08-21 2017-08-21 5-히드록시메틸-2-푸르푸랄의 제조공정에서 5-히드록시메틸-2-푸르푸랄과 다이메틸설폭사이드의 분리방법
KR10-2017-0105619 2017-08-21

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025044363A1 (fr) * 2023-08-30 2025-03-06 乔璞科技股份有限公司 Agent d'extraction pour séparer du 5-hydroxyméthylfurfural et des humines d'une solution de produit de réaction de déshydratation de glucides à six carbones (c6)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101141675B1 (ko) * 2009-08-12 2012-05-04 한국생산기술연구원 해조류 유래 갈락탄을 이용한 5-히드록시메틸-2-푸르푸랄의 제조방법
KR101146336B1 (ko) * 2009-10-01 2012-05-21 부경대학교 산학협력단 항산화 활성을 갖는 라우렌시아 운둘레이트 유래 5-하이드록시메틸-2-푸르푸랄
KR101217137B1 (ko) * 2012-03-05 2012-12-31 한국생산기술연구원 프록토오스를 포함하는 옥수수시럽으로부터 5-히드록시메틸-2-푸르푸랄을 제조하는 방법
KR20130035167A (ko) * 2011-09-29 2013-04-08 한국생산기술연구원 유기용매 하에서 이온교환수지를 이용한 5-히드록시메틸-2-푸르푸랄 또는 그의 알킬 에테르 유도체의 제조방법

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101141675B1 (ko) * 2009-08-12 2012-05-04 한국생산기술연구원 해조류 유래 갈락탄을 이용한 5-히드록시메틸-2-푸르푸랄의 제조방법
KR101146336B1 (ko) * 2009-10-01 2012-05-21 부경대학교 산학협력단 항산화 활성을 갖는 라우렌시아 운둘레이트 유래 5-하이드록시메틸-2-푸르푸랄
KR20130035167A (ko) * 2011-09-29 2013-04-08 한국생산기술연구원 유기용매 하에서 이온교환수지를 이용한 5-히드록시메틸-2-푸르푸랄 또는 그의 알킬 에테르 유도체의 제조방법
KR101217137B1 (ko) * 2012-03-05 2012-12-31 한국생산기술연구원 프록토오스를 포함하는 옥수수시럽으로부터 5-히드록시메틸-2-푸르푸랄을 제조하는 방법

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SAHA, B. ET AL.: "Advances in 5-hydroxymethylfurfural production from biomass in biphasic solvents", GREEN CHEMISTRY, vol. 16, no. 1, 2014, pages 24 - 38, XP055578359 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025044363A1 (fr) * 2023-08-30 2025-03-06 乔璞科技股份有限公司 Agent d'extraction pour séparer du 5-hydroxyméthylfurfural et des humines d'une solution de produit de réaction de déshydratation de glucides à six carbones (c6)
WO2025043536A1 (fr) * 2023-08-30 2025-03-06 乔璞科技股份有限公司 Procédé de purification de 5-hydroxyméthylfurfural

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