AU2014228755B2 - High purity lignin, lignin compositions, and higher structured lignin - Google Patents
High purity lignin, lignin compositions, and higher structured lignin Download PDFInfo
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- AU2014228755B2 AU2014228755B2 AU2014228755A AU2014228755A AU2014228755B2 AU 2014228755 B2 AU2014228755 B2 AU 2014228755B2 AU 2014228755 A AU2014228755 A AU 2014228755A AU 2014228755 A AU2014228755 A AU 2014228755A AU 2014228755 B2 AU2014228755 B2 AU 2014228755B2
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- 229920005610 lignin Polymers 0.000 title claims abstract description 397
- 239000000203 mixture Substances 0.000 title abstract description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 238000005570 heteronuclear single quantum coherence Methods 0.000 claims description 29
- 239000002028 Biomass Substances 0.000 claims description 26
- 238000004458 analytical method Methods 0.000 claims description 24
- 238000009833 condensation Methods 0.000 claims description 19
- 230000005494 condensation Effects 0.000 claims description 19
- 238000000045 pyrolysis gas chromatography Methods 0.000 claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 16
- QHJGZUSJKGVMTF-UHFFFAOYSA-N canolol Chemical compound COC1=CC(C=C)=CC(OC)=C1O QHJGZUSJKGVMTF-UHFFFAOYSA-N 0.000 claims description 16
- 238000005481 NMR spectroscopy Methods 0.000 claims description 14
- 239000011121 hardwood Substances 0.000 claims description 12
- ZFBNNSOJNZBLLS-UHFFFAOYSA-N 2,6-Dimethoxy-4-methylphenol Chemical compound COC1=CC(C)=CC(OC)=C1O ZFBNNSOJNZBLLS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000011122 softwood Substances 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 5
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 5
- 239000010813 municipal solid waste Substances 0.000 claims description 2
- 239000002699 waste material Substances 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 abstract description 13
- 238000006731 degradation reaction Methods 0.000 abstract description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
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- PHOPGVYKZWPIGA-UHFFFAOYSA-N 4-(3-hydroxypropyl)-2,6-dimethoxyphenol Chemical compound COC1=CC(CCCO)=CC(OC)=C1O PHOPGVYKZWPIGA-UHFFFAOYSA-N 0.000 description 14
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- MWAJWEFMQKZRKK-UHFFFAOYSA-N 1-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=CC(C(=O)C=C)=CC(OC)=C1O MWAJWEFMQKZRKK-UHFFFAOYSA-N 0.000 description 8
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- VCUJKQLQRUJWCJ-YWEYNIOJSA-N 1,3-dimethoxy-2-[(z)-prop-1-enoxy]benzene Chemical compound COC1=CC=CC(OC)=C1O\C=C/C VCUJKQLQRUJWCJ-YWEYNIOJSA-N 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- FWMPKHMKIJDEMJ-UHFFFAOYSA-N 4-allyl-2,6-dimethoxyphenol Chemical compound COC1=CC(CC=C)=CC(OC)=C1O FWMPKHMKIJDEMJ-UHFFFAOYSA-N 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
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- 239000002023 wood Substances 0.000 description 7
- CDICDSOGTRCHMG-ONEGZZNKSA-N (E)-sinapaldehyde Chemical compound COC1=CC(\C=C\C=O)=CC(OC)=C1O CDICDSOGTRCHMG-ONEGZZNKSA-N 0.000 description 6
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- 241000183024 Populus tremula Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- 239000010905 bagasse Substances 0.000 description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical group O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
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- QMPOHKDJNKTEHF-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1-benzofuran Chemical compound O1C2=CC=CC=C2CC1C1=CC=CC=C1 QMPOHKDJNKTEHF-UHFFFAOYSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
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- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005143 pyrolysis gas chromatography mass spectroscopy Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
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- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compounds Of Unknown Constitution (AREA)
- Paper (AREA)
- Processing Of Solid Wastes (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361802087P | 2013-03-15 | 2013-03-15 | |
| US61/802,087 | 2013-03-15 | ||
| PCT/US2014/029284 WO2014144746A1 (en) | 2013-03-15 | 2014-03-14 | High purity lignin, lignin compositions, and higher structured lignin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014228755A1 AU2014228755A1 (en) | 2015-10-29 |
| AU2014228755B2 true AU2014228755B2 (en) | 2017-10-26 |
Family
ID=51530126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| CN105189616A (zh) | 2015-12-23 |
| JP6883080B2 (ja) | 2021-06-09 |
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| JP2020023711A (ja) | 2020-02-13 |
| KR20150128986A (ko) | 2015-11-18 |
| PH12015502077A1 (en) | 2016-01-18 |
| NZ731063A (en) | 2018-09-28 |
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