WO2014087013A1 - Procédé d'isolement d'acide lévulinique - Google Patents

Procédé d'isolement d'acide lévulinique Download PDF

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Publication number
WO2014087013A1
WO2014087013A1 PCT/EP2013/075959 EP2013075959W WO2014087013A1 WO 2014087013 A1 WO2014087013 A1 WO 2014087013A1 EP 2013075959 W EP2013075959 W EP 2013075959W WO 2014087013 A1 WO2014087013 A1 WO 2014087013A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
levulinic acid
distillation
optionally
composition
Prior art date
Application number
PCT/EP2013/075959
Other languages
English (en)
Inventor
DE Arie RIJKE
Gerardus Wilhelmus Adrianus Hangx
Rudy Francois Maria Jozef Parton
Barthel ENGENDAHL
Original Assignee
Dsm Ip Assets B.V.
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
Application filed by Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Publication of WO2014087013A1 publication Critical patent/WO2014087013A1/fr

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Classifications

    • 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
    • C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
    • 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
    • Y02P20/10—Process efficiency

Definitions

  • the composition may comprise formic acid, acetic acid, furfural, and/or propionic acid. That is, the compound having a boiling point of less than 245°C may comprise formic acid, acetic acid, furfural, and/or propionic acid (i.e. may comprise each one of these compounds or a combination of two or more of these compounds).
  • the composition may comprise a biomass hydrolysate or C6 sugars acid hydrolysate.
  • Acid hydrolysis of biomass may not only result in formation of levulinic acid, but usually also results in the formation of formic acid, boiling temperature 100°C. Often a range of other low boiling compounds are produced such as acetic acid, furfural, and proprionic acid, all having a boiling temperature of 90°C or higher, but lower than the boiling temperature of levulinic acid.
  • the composition may also comprise an organic liquid, such as e.g. an organic phase obtained by solvent-solvent extraction.
  • Liquid-liquid extraction is a process for separating components (the solutes) of a liquid (the feed) by contact with a second liquid phase (the solvent). The two liquids must not be completely mutually miscible.
  • the process takes advantage of differences in the chemical properties of the feed components, such as differences in polarity and hydrophobic/hydrophilic character to separate them (T.C. Frank, L.Dahuron, B.S. Holden, W.D. Prince, A.F. Seibert, L.C. Wilson, Liquid-liquid extraction and other liquid- liquid operations and equipment in Perry's Chemical Engineering Handbook, 8th Edition, Section 15).
  • a flashing step may combine cooling of a biomass hydrolysate after acid hydrolysis and concentration of such biomass.
  • the recovered distillation residue may undergo one or more additional steps, preferably non-chemical steps.
  • additional steps include concentration, e.g. by flashing, solvent-solvent extraction, solid/liquid separation, and/or distillation. A combination of two or more of these steps is also possible.
  • the invention includes a process for the isolation of levulinic acid from a composition comprising levulinic acid and optionally a compound having a boiling temperature of less than 245°C, said process comprising;
  • the invention further provides the use of reactive distillation step for the isolation of levulinic acid from a composition comprising levulinic acid and optionally a compound having a boiling temperature of less than 245°C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé d'isolement d'acide lévulinique à partir d'une composition comprenant de l'acide lévulinique et facultativement un composé ayant une température d'ébullition inférieure à 245 °C. Ledit procédé consiste à : soumettre ladite composition à une distillation et récupérer un résidu de distillation comprenant au moins 1 % en poids de lactone angélique ; soumettre ledit résidu de distillation à une réaction d'hydratation dans certaines conditions de température et de temps et en présence d'eau et, facultativement, d'un catalyseur acide pour produire l'acide lévulinique ou pour augmenter la quantité d'acide lévulinique dans ledit résidu de distillation ; et facultativement récupérer ledit acide lévulinique. Le procédé est approprié pour isoler et préparer l'acide lévulinique à partir de compositions préparées par une hydrolyse acide d'une biomasse lignocellulosique, ainsi qu'à partir de compositions préparées par une hydrolyse acide de sucre, tel que le glucose et le fructose. L'invention concerne également l'utilisation d'une distillation réactive pour l'isolement d'acide lévulinique à partir d'une composition comprenant de l'acide lévulinique et facultativement un composé possédant une température d'ébullition inférieure à 245 °C.
PCT/EP2013/075959 2012-12-07 2013-12-09 Procédé d'isolement d'acide lévulinique WO2014087013A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201261734512P 2012-12-07 2012-12-07
EP12196075.1 2012-12-07
US61/734,512 2012-12-07
EP12196075 2012-12-07

Publications (1)

Publication Number Publication Date
WO2014087013A1 true WO2014087013A1 (fr) 2014-06-12

Family

ID=47290820

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/075959 WO2014087013A1 (fr) 2012-12-07 2013-12-09 Procédé d'isolement d'acide lévulinique

Country Status (1)

Country Link
WO (1) WO2014087013A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3156389A1 (fr) 2015-10-12 2017-04-19 GFBiochemicals Ltd Procédé de purification de l'acide lévulinique
IT201700068744A1 (it) * 2017-06-21 2018-12-21 Bio On Spa Processo per la produzione di acido levulinico.
US10550067B2 (en) 2015-07-10 2020-02-04 Gfbiochemicals Ip Assets B.V. Levulinic acid compositions

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE745313C (de) 1941-12-17 1944-03-02 Dr Johannes Heinrich Helberger Verfahren zur Darstellung von Angelicalacton
GB1596651A (en) * 1978-01-06 1981-08-26 Bp Chem Int Ltd Process for the recovery of laevulinic acid in the form of its internal ester alphaangelica lactone from mixtures of compounds of similar boiling-point
WO1998019986A1 (fr) * 1996-11-08 1998-05-14 Arkenol, Inc. Technique de production d'acide levulinique et de ses derives
US20050171374A1 (en) * 2004-01-30 2005-08-04 Manzer Leo E. Preparation of levulinic acid esters from alpha-angelica lactone and olefins; use of ester compositions as fuel additives
US7896944B2 (en) 2004-06-23 2011-03-01 Lone Knight Limited Method for extracting fulvic acid molecules
US20120302766A1 (en) * 2011-05-25 2012-11-29 Dumesic James A Solute-enhanced production of gamma-valerolactone (gvl) from aqueous solutions of levulinic acid
WO2013078391A1 (fr) * 2011-11-23 2013-05-30 Segetis, Inc. Procédé de préparation d'acide lévulinique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE745313C (de) 1941-12-17 1944-03-02 Dr Johannes Heinrich Helberger Verfahren zur Darstellung von Angelicalacton
GB1596651A (en) * 1978-01-06 1981-08-26 Bp Chem Int Ltd Process for the recovery of laevulinic acid in the form of its internal ester alphaangelica lactone from mixtures of compounds of similar boiling-point
WO1998019986A1 (fr) * 1996-11-08 1998-05-14 Arkenol, Inc. Technique de production d'acide levulinique et de ses derives
US20050171374A1 (en) * 2004-01-30 2005-08-04 Manzer Leo E. Preparation of levulinic acid esters from alpha-angelica lactone and olefins; use of ester compositions as fuel additives
US7896944B2 (en) 2004-06-23 2011-03-01 Lone Knight Limited Method for extracting fulvic acid molecules
US20120302766A1 (en) * 2011-05-25 2012-11-29 Dumesic James A Solute-enhanced production of gamma-valerolactone (gvl) from aqueous solutions of levulinic acid
WO2013078391A1 (fr) * 2011-11-23 2013-05-30 Segetis, Inc. Procédé de préparation d'acide lévulinique

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
T.C. FRANK; L.DAHURON; B.S. HOLDEN; W.D. PRINCE; A.F. SEIBERT; L.C. WILSON: "Perry's Chemical Engineering Handbook", article "Liquid-liquid extraction and other liquid-liquid operations and equipment"
Y.MARCUS: "Solvent Extraction Principles and Practice", MARCEL DEKKER INC., article "Principles of Solubility and Solutions"
YANG; SEN, CHEM. SUS. CHEM., vol. 3, 2010, pages 597 - 603

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10550067B2 (en) 2015-07-10 2020-02-04 Gfbiochemicals Ip Assets B.V. Levulinic acid compositions
EP3156389A1 (fr) 2015-10-12 2017-04-19 GFBiochemicals Ltd Procédé de purification de l'acide lévulinique
WO2017064069A1 (fr) 2015-10-12 2017-04-20 Gfbiochemicals Ltd Procédé pour la purification de l'acide lévulinique
US10239814B2 (en) 2015-10-12 2019-03-26 Gfbiochemicals Ip Assets B.V. Process for the purification of levulinic acid
IT201700068744A1 (it) * 2017-06-21 2018-12-21 Bio On Spa Processo per la produzione di acido levulinico.
WO2018235012A1 (fr) * 2017-06-21 2018-12-27 Bio-On S.P.A. Procédé de production d'acide lévulinique

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