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WO2018130450A1 - Plasma basse température pour décomposition de lignine - Google Patents

Plasma basse température pour décomposition de lignine Download PDF

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Publication number
WO2018130450A1
WO2018130450A1 PCT/EP2018/050167 EP2018050167W WO2018130450A1 WO 2018130450 A1 WO2018130450 A1 WO 2018130450A1 EP 2018050167 W EP2018050167 W EP 2018050167W WO 2018130450 A1 WO2018130450 A1 WO 2018130450A1
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WO
WIPO (PCT)
Prior art keywords
lignin
low temperature
stream
temperature plasma
aromatic compounds
Prior art date
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Application number
PCT/EP2018/050167
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English (en)
Inventor
Martin ØSTBERG
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.)
Topsoe AS
Original Assignee
Haldor Topsoe AS
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 Haldor Topsoe AS filed Critical Haldor Topsoe AS
Publication of WO2018130450A1 publication Critical patent/WO2018130450A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
    • C07C37/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes by hydrolysis of lignin or sulfite waste liquor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms

Definitions

  • Embodiments of the invention generally relate to a process for converting a biomass feed into valuable chemicals, wherein the biomass feed comprises lignin.
  • Lignin is a waste material from wood processes when cellulose and hemi-cellulose have been extracted. Lignin comprises very large molecules that contains interesting chemical structures, i.a. aromatic compounds.
  • lignin is used as a resource for production of some chemicals but the majority of lignin is used as fuel with a rather low value.
  • Biomass is a feedstock that is available in large quantities in many countries, and at a low cost.
  • biomass includes lignin containing plants. Examples of sources of plant biomass are numerous types of plants, including all tree species. Often lignin is a residue when cellulose and hemi-cellulose is extracted from wood.
  • Embodiments of the invention generally relate to a process for converting a biomass feed into valuable chemicals, wherein the biomass feed comprises lignin, said lignin comprising aromatic species having aromatic bonded carbon and/or bonds to functional groups, said process comprising the steps of:
  • the separation process of step b) is a phase separation combined with e.g. a distillation process.
  • the phase separation may take place using a phase separation paper sep- arating the solvent phase from the aqueous phase.
  • the distillation process may take place in a distillation column separating the species based on their boiling points.
  • low temperature plasma is meant to denote non-thermal plasma generated by electrons using an electric discharge. This may take place at temperatures as low as between 10 and 100 ° C.
  • Low temperature plasma may be generated by a high frequency electric field. Using the high frequency generation of a low temperature plasma causes only a very moderate temperature increase.
  • the low temperature plasma comprises an ionization field lead- ing to excitation, dissociation and ionization of molecules.
  • the term "using low temperature plasma to decompose lignin molecules” is meant to denote the break of aliphatic bonds in the lignin polymer leading to smaller molecules.
  • the term “valuable chemicals” is meant to denote chemicals that are attractive feedstocks for chemical productions like benzene, phenol, toluene, styrene and other aro- matics.
  • the stream comprising other products is used as a feed stream for syngas production.
  • a syngas production is e.g. a second low temperature plasma process resulting in a synthesis gas stream and an aqueous waste stream.
  • the low temperature plasma is submerged into the aqueous phase. This means, that the generation of the electrons providing the plasma by the electric discharge is submerged into the aqueous phase.
  • the temperature of the low temperature plasma is between about 10°C and about 90°C.
  • the temperature of the low temperature plasma is e.g. between about 40°C and about 75°C.
  • step a) of the process is a continuous process.
  • Step b) of the process may be a continuous process or a batch process.
  • the biomass feed is a black liquor feed stream.
  • Black liquor is a waste product from the kraft process when digesting pulpwood into paper pulp removing lignin, hemicelluloses and other extractives from the wood to free the cellulose fibres.
  • step a) of the process takes place within a low tem- perature plasma reactor, said low temperature plasma reactor comprising catalyst for catalysing the reaction.
  • the catalyst is e.g. a hydrogenation catalyst or an oxidation catalyst that enable bond breaking by hydrogenation or oxidation of the carbon-carbon or carbon-oxygen bonds in the lignin molecule, respectively.
  • the low temperature plasma reactor may e.g. be a batch process in a stirred tank or a continuous process in a fixed bed reactor.
  • FIG. 1 is a diagram of the process according to the invention.
  • Figure 2 shows an example of a possible lignin structure.
  • FIG. 1 is a diagram of the process 10 according to the invention.
  • a biomass feed stream 1 comprising lignin is fed to a low temperature plasma reactor 20.
  • the biomass feed stream 1 is a stream of aqueous lignin.
  • Lignin is very large molecules that contain i.a. aromatic compounds.
  • the low temperature plasma is used to decompose lignin molecules in the stream of aqueous lignin into smaller molecules, where the functionality of the smaller molecules is preserved.
  • the temperature of the low temperature plasma is between about 10°C and about 90°C.
  • the temperature of the low temperature plasma is between about 40°C and about 75°C.
  • the raw product stream 2 comprising a mixture of aromatic compounds and other products is separated into at least two streams, viz. a stream 3 com- prising aromatic compounds and a stream 4 comprising other products.
  • the stream 4 comprising other products may be fed to a second low temperature plasma generator 40 resulting in a synthesis gas stream 5 and an aqueous waste stream 6.
  • the synthesis gas stream 5 may undergo further purification or other processes downstream the second low temperature plasma generator 40.
  • the synthesis gas comprises mainly hydrogen and carbon monoxide, and is a valuable feedstock for production of chemicals.
  • the low temperature plasma will be capable of breaking the lignin structure into smaller molecules in a way that the interesting chemical structures, e.g. the aromatic compounds, are maintained. This is possible as a low temperature plasma may be tuned only to energize certain chemical bonds, meaning it is possible to selectively separate the lignin into smaller molecules in a controlled matter.
  • These low tempera- ture plasmas may be designed in many forms and phases.
  • a plasma that will be submerged in a slurry phase containing the lignin e.g. black liquor is used. This eases the handling and reduces overall cost.
  • FIG. 2 shows an example of a possible lignin structure.
  • Lignin is a huge molecule con- sisting of aromatic (benzene) structures cross linked with aliphatic bonds (C-C or C-O- C). The energy levels of a low temperature plasma are able to energize the aliphatic bond without significant effect on the aromatic bonds. This leads to the cleavage of the lignin molecule into small molecules of benzene with functional groups like phenol, toluene, etc.
  • one or more heat exchange means or other means for heating or cooling the streams may be included to ensure the proper temperatures, e.g. for the separation phase.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Processing Of Solid Wastes (AREA)

Abstract

L'invention concerne un procédé de conversion d'une charge d'alimentation de biomasse en produits chimiques valorisables, la charge d'alimentation de biomasse comprenant de la lignine, ladite lignine comprenant des composés aromatiques ayant un carbone aromatique lié et/ou des liaisons à des groupes fonctionnels. Le procédé de l'invention comprend les étapes consistant à : a) utiliser un plasma à basse température pour décomposer des molécules de lignine dans la lignine en molécules plus petites, les liaisons chimiques réticulant les molécules de lignine étant brisées tandis qu'une partie importante du carbone aromatique lié et/ou des liaisons avec des groupes fonctionnels des composés aromatiques est maintenue, ce qui permet d'obtenir un flux de produit brut comprenant des composés aromatiques et d'autres produits, b) séparer le flux du produit brut en un flux comprenant des composés aromatiques et un flux comprenant d'autres produits.
PCT/EP2018/050167 2017-01-13 2018-01-04 Plasma basse température pour décomposition de lignine Ceased WO2018130450A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DKPA201700034 2017-01-13
DKPA201700034 2017-01-13

Publications (1)

Publication Number Publication Date
WO2018130450A1 true WO2018130450A1 (fr) 2018-07-19

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2018/050167 Ceased WO2018130450A1 (fr) 2017-01-13 2018-01-04 Plasma basse température pour décomposition de lignine

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Country Link
WO (1) WO2018130450A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621409A (zh) * 2020-12-08 2022-06-14 西南林业大学 一种增强增韧三聚氰胺树脂的改性方法
CN116920754A (zh) * 2023-05-26 2023-10-24 重庆科技学院 一种碱木质素分解反应器及分解方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120202260A1 (en) * 2009-09-04 2012-08-09 Lignol Innovations Ltd. Hybrid biorefining and gasification of lignocellulosic feedstocks

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120202260A1 (en) * 2009-09-04 2012-08-09 Lignol Innovations Ltd. Hybrid biorefining and gasification of lignocellulosic feedstocks

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HAMED TAGHVAEI ET AL: "Upgrading of anisole using in situ generated hydrogen in pin to plate pulsed corona discharge", RSC ADVANCES: AN INTERNATIONAL JOURNAL TO FURTHER THE CHEMICAL SCIENCES, vol. 6, no. 100, 10 October 2016 (2016-10-10), GB, pages 98369 - 98380, XP055463887, ISSN: 2046-2069, DOI: 10.1039/C6RA21417G *
JI-YOUNG KWON ET AL: "Removal of Residual COD in Biologically Treated Paper-Mill Effluent and Degradation of Lignin Using Nonthermal Plasma Unit", JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH. PART A: TOXIC HAZARDOUS SUBSTANCES AND ENVIRONMENTAL ENGINEERING, vol. 39, no. 7, 27 December 2004 (2004-12-27), US, pages 1853 - 1865, XP055463867, ISSN: 1093-4529, DOI: 10.1081/ESE-120037883 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621409A (zh) * 2020-12-08 2022-06-14 西南林业大学 一种增强增韧三聚氰胺树脂的改性方法
CN116920754A (zh) * 2023-05-26 2023-10-24 重庆科技学院 一种碱木质素分解反应器及分解方法

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