DE102014108841B3 - Verfahren zur Desodorierung von Lignin - Google Patents
Verfahren zur Desodorierung von Lignin Download PDFInfo
- Publication number
- DE102014108841B3 DE102014108841B3 DE102014108841.7A DE102014108841A DE102014108841B3 DE 102014108841 B3 DE102014108841 B3 DE 102014108841B3 DE 102014108841 A DE102014108841 A DE 102014108841A DE 102014108841 B3 DE102014108841 B3 DE 102014108841B3
- Authority
- DE
- Germany
- Prior art keywords
- lignin
- bar
- supercritical fluid
- temperature
- pressure
- 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.)
- Active
Links
- 229920005610 lignin Polymers 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 51
- 239000000758 substrate Substances 0.000 claims abstract description 45
- 239000012530 fluid Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 32
- 239000012855 volatile organic compound Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 19
- 238000003809 water extraction Methods 0.000 claims description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 16
- 239000001569 carbon dioxide Substances 0.000 claims description 16
- 230000007071 enzymatic hydrolysis Effects 0.000 claims description 8
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 8
- 108010059892 Cellulase Proteins 0.000 claims description 6
- 229940106157 cellulase Drugs 0.000 claims description 6
- 230000002255 enzymatic effect Effects 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- 230000001877 deodorizing effect Effects 0.000 claims description 2
- 238000004332 deodorization Methods 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 108010084185 Cellulases Proteins 0.000 description 5
- 102000005575 Cellulases Human genes 0.000 description 5
- 229920002488 Hemicellulose Polymers 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 229920005611 kraft lignin Polymers 0.000 description 3
- 229930014251 monolignol Natural products 0.000 description 3
- 125000002293 monolignol group Chemical group 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- YWHLKYXPLRWGSE-UHFFFAOYSA-N Dimethyl trisulfide Chemical compound CSSSC YWHLKYXPLRWGSE-UHFFFAOYSA-N 0.000 description 2
- 108010029541 Laccase Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- -1 aromatic alcohols Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- JMFRWRFFLBVWSI-NSCUHMNNSA-N coniferol Chemical compound COC1=CC(\C=C\CO)=CC=C1O JMFRWRFFLBVWSI-NSCUHMNNSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000012978 lignocellulosic material Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- LZFOPEXOUVTGJS-ONEGZZNKSA-N trans-sinapyl alcohol Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O LZFOPEXOUVTGJS-ONEGZZNKSA-N 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LZFOPEXOUVTGJS-UHFFFAOYSA-N cis-sinapyl alcohol Natural products COC1=CC(C=CCO)=CC(OC)=C1O LZFOPEXOUVTGJS-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229940119526 coniferyl alcohol Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000009144 enzymatic modification Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229930015763 p-coumaryl alcohol Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229930015704 phenylpropanoid Natural products 0.000 description 1
- 125000001474 phenylpropanoid group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000009283 thermal hydrolysis Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- PTNLHDGQWUGONS-UHFFFAOYSA-N trans-p-coumaric alcohol Natural products OCC=CC1=CC=C(O)C=C1 PTNLHDGQWUGONS-UHFFFAOYSA-N 0.000 description 1
- PTNLHDGQWUGONS-OWOJBTEDSA-N trans-p-coumaryl alcohol Chemical compound OC\C=C\C1=CC=C(O)C=C1 PTNLHDGQWUGONS-OWOJBTEDSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0215—Solid material in other stationary receptacles
- B01D11/0219—Fixed bed of solid material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/028—Flow sheets
- B01D11/0284—Multistage extraction
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H8/00—Macromolecular compounds derived from lignocellulosic materials
-
- 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Extraction Or Liquid Replacement (AREA)
- Compounds Of Unknown Constitution (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102014108841.7A DE102014108841B3 (de) | 2014-06-24 | 2014-06-24 | Verfahren zur Desodorierung von Lignin |
PCT/DE2015/100137 WO2015197048A1 (de) | 2014-06-24 | 2015-03-31 | Verfahren zur desodorierung von lignin |
DE112015002989.3T DE112015002989A5 (de) | 2014-06-24 | 2015-03-31 | Verfahren zur Desodorierung von Lignin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102014108841.7A DE102014108841B3 (de) | 2014-06-24 | 2014-06-24 | Verfahren zur Desodorierung von Lignin |
Publications (1)
Publication Number | Publication Date |
---|---|
DE102014108841B3 true DE102014108841B3 (de) | 2015-05-28 |
Family
ID=53045746
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE102014108841.7A Active DE102014108841B3 (de) | 2014-06-24 | 2014-06-24 | Verfahren zur Desodorierung von Lignin |
DE112015002989.3T Withdrawn DE112015002989A5 (de) | 2014-06-24 | 2015-03-31 | Verfahren zur Desodorierung von Lignin |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE112015002989.3T Withdrawn DE112015002989A5 (de) | 2014-06-24 | 2015-03-31 | Verfahren zur Desodorierung von Lignin |
Country Status (2)
Country | Link |
---|---|
DE (2) | DE102014108841B3 (sv) |
WO (1) | WO2015197048A1 (sv) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017222455A1 (en) * | 2016-06-22 | 2017-12-28 | Valmet Ab | Method of producing lignin with reduced amount of odorous substances |
WO2018004427A1 (en) * | 2016-06-22 | 2018-01-04 | Valmet Ab | Method of producing lignin with reduced amount of odorous substances |
WO2020192929A1 (de) | 2019-03-28 | 2020-10-01 | Technische Universität Hamburg | Verfahren zur herstellung ultrafeiner lignin-partikel |
WO2021123507A1 (en) * | 2019-12-20 | 2021-06-24 | Andritz Oy | A method of removing volatile compounds from a lignin-containing material, use of a distillation method, and a lignin-containing material |
CN113082760A (zh) * | 2021-03-10 | 2021-07-09 | 广州中国科学院先进技术研究所 | 一种固体粉末除臭方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109438724A (zh) * | 2018-11-27 | 2019-03-08 | 浙江华康药业股份有限公司 | 一种提取木质纤维素中木质素的方法及其应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0750068A1 (fr) * | 1995-06-22 | 1996-12-27 | Elf Atochem S.A. | Procédé de traitement des rejets gazeux issus du procédé Kraft à l'aide de dérivés de l'acide undécylénique et/ou undécynoique |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5846787A (en) * | 1994-07-11 | 1998-12-08 | Purdue Research Foundation Office Of Technology Transfer | Processes for treating cellulosic material |
FR2798879B1 (fr) * | 1999-09-27 | 2001-10-19 | Commissariat Energie Atomique | Procede de traitement, et d'extraction de composes organiques du liege, par un fluide dense sous pression |
PT103006A (pt) * | 2003-08-07 | 2005-02-28 | Juvenal | Processo para a eliminacao/reducao de compostos com gosto/odor a mofo em materiais para contacto com alimentos e bebidas, e em alimentos e bebidas |
DE102006057566B4 (de) | 2006-11-30 | 2011-02-24 | Sächsisches Institut für Angewandte Biotechnologie e.V. (SIAB) | Verfahren zur Herstellung eines emissionsreduzierten lignozellulosen Rohstoffes bzw. Werkstoffs, Bauteils oder Produkts |
US8759498B2 (en) * | 2011-12-30 | 2014-06-24 | Renmatix, Inc. | Compositions comprising lignin |
-
2014
- 2014-06-24 DE DE102014108841.7A patent/DE102014108841B3/de active Active
-
2015
- 2015-03-31 DE DE112015002989.3T patent/DE112015002989A5/de not_active Withdrawn
- 2015-03-31 WO PCT/DE2015/100137 patent/WO2015197048A1/de active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0750068A1 (fr) * | 1995-06-22 | 1996-12-27 | Elf Atochem S.A. | Procédé de traitement des rejets gazeux issus du procédé Kraft à l'aide de dérivés de l'acide undécylénique et/ou undécynoique |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017222455A1 (en) * | 2016-06-22 | 2017-12-28 | Valmet Ab | Method of producing lignin with reduced amount of odorous substances |
WO2018004427A1 (en) * | 2016-06-22 | 2018-01-04 | Valmet Ab | Method of producing lignin with reduced amount of odorous substances |
US10882879B2 (en) | 2016-06-22 | 2021-01-05 | Valmet Ab | Method of producing lignin with reduced amount of odorous substances |
WO2020192929A1 (de) | 2019-03-28 | 2020-10-01 | Technische Universität Hamburg | Verfahren zur herstellung ultrafeiner lignin-partikel |
WO2021123507A1 (en) * | 2019-12-20 | 2021-06-24 | Andritz Oy | A method of removing volatile compounds from a lignin-containing material, use of a distillation method, and a lignin-containing material |
CN113082760A (zh) * | 2021-03-10 | 2021-07-09 | 广州中国科学院先进技术研究所 | 一种固体粉末除臭方法 |
Also Published As
Publication number | Publication date |
---|---|
DE112015002989A5 (de) | 2017-04-06 |
WO2015197048A1 (de) | 2015-12-30 |
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R081 | Change of applicant/patentee |
Owner name: LIGNOPURE GMBH, DE Free format text: FORMER OWNERS: TECHNISCHE UNIVERSITAET HAMBURG-HARBURG, 21073 HAMBURG, DE; TUTECH INNOVATION GMBH, 21079 HAMBURG, DE |
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