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WO2020174078A1 - Procédé de production de propane-1,2-diol - Google Patents

Procédé de production de propane-1,2-diol Download PDF

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Publication number
WO2020174078A1
WO2020174078A1 PCT/EP2020/055242 EP2020055242W WO2020174078A1 WO 2020174078 A1 WO2020174078 A1 WO 2020174078A1 EP 2020055242 W EP2020055242 W EP 2020055242W WO 2020174078 A1 WO2020174078 A1 WO 2020174078A1
Authority
WO
WIPO (PCT)
Prior art keywords
lactic acid
reaction
conversion
mpa
propanediol
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2020/055242
Other languages
German (de)
English (en)
Inventor
Regina Palkovits
Peter HAUSOUL
Xinde WANG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rheinisch Westlische Technische Hochschuke RWTH
Original Assignee
Rheinisch Westlische Technische Hochschuke RWTH
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 Rheinisch Westlische Technische Hochschuke RWTH filed Critical Rheinisch Westlische Technische Hochschuke RWTH
Publication of WO2020174078A1 publication Critical patent/WO2020174078A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/10—Magnesium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/83—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with rare earths or actinides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
    • B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
    • B01J29/0316—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41 containing iron group metals, noble metals or copper
    • B01J29/0333—Iron group metals or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0236—Drying, e.g. preparing a suspension, adding a soluble salt and drying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation
    • B01J37/031—Precipitation
    • B01J37/033—Using Hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases

Definitions

  • DE 10 2008 013 474 A1 describes a process for producing lactic acid from primary alcohols or aldehydes in the presence of a transition metal catalyst.
  • the process allows the formation of lactic acid with high selectivity, 1,2-propanediol being formed as a by-product when glycerol is used as the starting material.
  • the transition metal catalysts can be used as such, for example in the form of powders, granules, particles or else in extrudate form.
  • the catalyst is in supported form, i. used as a so-called supported catalyst, on a suitable support material.
  • suitable support materials are, for example, conventional support materials such as silica, aluminum oxide, lanthanum oxide, zirconium oxide, aluminosilicates, synthetic porous materials or clay.
  • the catalyst is used in supported form on a support material selected from silica,
  • FIG. 3 shows the catalytic activity in the presence of various hydroxides.
  • FIG. 1 shows the catalytic performance of the individual catalysts under the following reaction conditions: 0.1 g catalyst, 25% loading, 0.5 g lactic acid, 0.1 g Mg (OH) 2 ,
  • Calcium lactate (Ca (LA) 2) over Cu / SiCE was carried out in a 50 ml autoclave with a Teflon inlet. An appropriate amount of the alkaline salt dissolved in 20 ml of deionized water was added along with 0.1 g of Cu / SiCE. In each case, 5.6 mmol of lactate were used. The closed autoclave was flushed five times and brought to 5 MPa with H2. The reaction was carried out at 513 K with 750 rpm stirring carried out. Samples were taken at 0.5, 1, 2, 4 and 8 hours after the temperature reached 513K.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production de propane-1,2-diol à partir d'acide lactique par hydrogénation catalytique en solution aqueuse, par réaction en présence d'une base et/ou d'un sel basique d'un métal alcalin et/ou d'un métal alcalino-terreux.
PCT/EP2020/055242 2019-02-28 2020-02-28 Procédé de production de propane-1,2-diol Ceased WO2020174078A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102019105105.3 2019-02-28
DE102019105105.3A DE102019105105A1 (de) 2019-02-28 2019-02-28 Verfahren zur Herstellung von 1,2-Propandiol

Publications (1)

Publication Number Publication Date
WO2020174078A1 true WO2020174078A1 (fr) 2020-09-03

Family

ID=69740344

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2020/055242 Ceased WO2020174078A1 (fr) 2019-02-28 2020-02-28 Procédé de production de propane-1,2-diol

Country Status (2)

Country Link
DE (1) DE102019105105A1 (fr)
WO (1) WO2020174078A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19756171A1 (de) * 1997-12-17 1999-07-01 Basf Ag Verfahren zur Hydrierung von Carbonsäuren oder deren Anhydriden oder Estern zu Alkoholen
WO2000030744A1 (fr) * 1998-11-24 2000-06-02 Michigan State University Hydrogenation catalytique en phase condensee servant a transformer l'acide lactique en propylene glycol
WO2001016063A1 (fr) 1999-09-02 2001-03-08 Wisconsin Alumni Research Foundation Technique de reduction catalytique de groupes acide carboxylique en groupes hydroxyles dans des acides hydroxycarboxyliques
DE102008013474A1 (de) 2008-03-10 2009-09-24 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Katalytisches Verfahren zur Gewinnung von chemischen Grundstoffen aus nachwachsenden Rohstoffen

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19756171A1 (de) * 1997-12-17 1999-07-01 Basf Ag Verfahren zur Hydrierung von Carbonsäuren oder deren Anhydriden oder Estern zu Alkoholen
WO2000030744A1 (fr) * 1998-11-24 2000-06-02 Michigan State University Hydrogenation catalytique en phase condensee servant a transformer l'acide lactique en propylene glycol
US6403844B1 (en) 1998-11-24 2002-06-11 Board Of Trustees Of Michigan State University Condensed phase catalytic hydrogenation of lactic acid to propylene glycol
WO2001016063A1 (fr) 1999-09-02 2001-03-08 Wisconsin Alumni Research Foundation Technique de reduction catalytique de groupes acide carboxylique en groupes hydroxyles dans des acides hydroxycarboxyliques
DE102008013474A1 (de) 2008-03-10 2009-09-24 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Katalytisches Verfahren zur Gewinnung von chemischen Grundstoffen aus nachwachsenden Rohstoffen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ANNA KATHARINA BEINE ET AL: "Selective production of glycols from xylitol over Ru on covalent triazine frameworks - suppressing decarbonylation reactions", GREEN CHEMISTRY, vol. 20, no. 6, 1 January 2018 (2018-01-01), GB, pages 1316 - 1322, XP055691253, ISSN: 1463-9262, DOI: 10.1039/C8GC00208H *

Also Published As

Publication number Publication date
DE102019105105A1 (de) 2020-09-03

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