CN104736245A - 高分子催化剂和固载化催化剂、以及使用该催化剂消化纤维素材料的方法 - Google Patents
高分子催化剂和固载化催化剂、以及使用该催化剂消化纤维素材料的方法 Download PDFInfo
- Publication number
- CN104736245A CN104736245A CN201380055050.3A CN201380055050A CN104736245A CN 104736245 A CN104736245 A CN 104736245A CN 201380055050 A CN201380055050 A CN 201380055050A CN 104736245 A CN104736245 A CN 104736245A
- Authority
- CN
- China
- Prior art keywords
- carbon load
- sulfonic acid
- phosphonic acids
- acid
- catalyst
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 626
- 238000000034 method Methods 0.000 title claims abstract description 157
- 239000000463 material Substances 0.000 title claims abstract description 87
- 230000002378 acidificating effect Effects 0.000 claims abstract description 86
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 657
- -1 pyrans chloride phosphonic acids Chemical class 0.000 claims description 322
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 317
- 229910052799 carbon Inorganic materials 0.000 claims description 260
- 229910003481 amorphous carbon Inorganic materials 0.000 claims description 206
- 239000002253 acid Substances 0.000 claims description 159
- 235000000346 sugar Nutrition 0.000 claims description 113
- 150000002500 ions Chemical class 0.000 claims description 106
- 125000003118 aryl group Chemical group 0.000 claims description 95
- 125000001072 heteroaryl group Chemical group 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 150000007516 brønsted-lowry acids Chemical class 0.000 claims description 77
- 239000007791 liquid phase Substances 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 65
- 150000001768 cations Chemical group 0.000 claims description 61
- 239000007790 solid phase Substances 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 41
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 32
- 229910052698 phosphorus Inorganic materials 0.000 claims description 31
- 239000011574 phosphorus Substances 0.000 claims description 31
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 claims description 30
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 22
- 150000002460 imidazoles Chemical class 0.000 claims description 22
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 21
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 20
- 150000003009 phosphonic acids Chemical class 0.000 claims description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006731 degradation reaction Methods 0.000 claims description 17
- 239000002028 Biomass Substances 0.000 claims description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 15
- 150000003217 pyrazoles Chemical class 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 13
- 150000003235 pyrrolidines Chemical class 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 230000002209 hydrophobic effect Effects 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
- 150000003053 piperidines Chemical class 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 7
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 claims description 6
- DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 5
- 229910003460 diamond Inorganic materials 0.000 claims description 5
- 239000010432 diamond Substances 0.000 claims description 5
- 239000000428 dust Substances 0.000 claims description 5
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 claims description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 5
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 claims description 5
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- AZFSRJWWAXEWED-UHFFFAOYSA-N 1,3-oxazol-2-yl acetate Chemical compound CC(=O)OC1=NC=CO1 AZFSRJWWAXEWED-UHFFFAOYSA-N 0.000 claims description 3
- GIQQAQFTVJTULV-UHFFFAOYSA-N 1,3-oxazol-3-ium;chloride Chemical compound Cl.C1=COC=N1 GIQQAQFTVJTULV-UHFFFAOYSA-N 0.000 claims description 3
- IVODAIGHBCWWFM-UHFFFAOYSA-N 1,3-oxazole;hydrobromide Chemical compound Br.C1=COC=N1 IVODAIGHBCWWFM-UHFFFAOYSA-N 0.000 claims description 3
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical class OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 3
- VWUCIBOKNZGWLX-UHFFFAOYSA-N 1h-imidazol-1-ium;bromide Chemical compound [Br-].C1=C[NH+]=CN1 VWUCIBOKNZGWLX-UHFFFAOYSA-N 0.000 claims description 3
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 claims description 3
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 3
- NTVKSUPEUFXUGS-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)acetic acid Chemical class OC(=O)CC=1C=CNN=1 NTVKSUPEUFXUGS-UHFFFAOYSA-N 0.000 claims description 3
- VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical class OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 claims description 3
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical class OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- UQAUZQARLQGLIX-UHFFFAOYSA-N C(=O)O.C(C)P(CC)CC Chemical class C(=O)O.C(C)P(CC)CC UQAUZQARLQGLIX-UHFFFAOYSA-N 0.000 claims description 3
- SZNLMSIMTYKFMH-UHFFFAOYSA-N C(=O)O.N1=NC=CC=C1 Chemical class C(=O)O.N1=NC=CC=C1 SZNLMSIMTYKFMH-UHFFFAOYSA-N 0.000 claims description 3
- ZHLOSCVNGHUGLZ-UHFFFAOYSA-M C(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical class C(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)C1=CC=CC=C1 ZHLOSCVNGHUGLZ-UHFFFAOYSA-M 0.000 claims description 3
- LTVPBZZJQJFFNW-UHFFFAOYSA-N C(C)(=O)O.P(O)(O)=O.N1=CN=CC=C1 Chemical class C(C)(=O)O.P(O)(O)=O.N1=CN=CC=C1 LTVPBZZJQJFFNW-UHFFFAOYSA-N 0.000 claims description 3
- GATLNDAQZPJBPG-UHFFFAOYSA-M C(C)(=O)[O-].C(CC)[P+](CCC)CCC Chemical compound C(C)(=O)[O-].C(CC)[P+](CCC)CCC GATLNDAQZPJBPG-UHFFFAOYSA-M 0.000 claims description 3
- NAQGOTSGKVUHBV-UHFFFAOYSA-M C(C)(=O)[O-].C(CCC)[P+](CCCC)CCCC Chemical compound C(C)(=O)[O-].C(CCC)[P+](CCCC)CCCC NAQGOTSGKVUHBV-UHFFFAOYSA-M 0.000 claims description 3
- RDXDRLXWCWNLSD-UHFFFAOYSA-M C(C)(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)C1=CC=CC=C1 RDXDRLXWCWNLSD-UHFFFAOYSA-M 0.000 claims description 3
- QTFCFKGUHJXJAY-UHFFFAOYSA-M C(C)(=O)[O-].C[P+](C)C Chemical compound C(C)(=O)[O-].C[P+](C)C QTFCFKGUHJXJAY-UHFFFAOYSA-M 0.000 claims description 3
- BABFWNSMLQWNLV-UHFFFAOYSA-M C(C)(=O)[O-].F[P+](F)F Chemical compound C(C)(=O)[O-].F[P+](F)F BABFWNSMLQWNLV-UHFFFAOYSA-M 0.000 claims description 3
- NVSTVRPHWVQNQZ-UHFFFAOYSA-N C(CC)[P](CCC)(CCC)Br Chemical compound C(CC)[P](CCC)(CCC)Br NVSTVRPHWVQNQZ-UHFFFAOYSA-N 0.000 claims description 3
- CTJXEWYAMXLGCH-UHFFFAOYSA-N C(CC)[P](CCC)(CCC)Cl Chemical compound C(CC)[P](CCC)(CCC)Cl CTJXEWYAMXLGCH-UHFFFAOYSA-N 0.000 claims description 3
- INYDGENFCROFLO-UHFFFAOYSA-N C(CCC)[P](CCCC)(CCCC)Br Chemical compound C(CCC)[P](CCCC)(CCCC)Br INYDGENFCROFLO-UHFFFAOYSA-N 0.000 claims description 3
- MLWFBWIFQSUPAW-UHFFFAOYSA-N C(CCC)[P](CCCC)(CCCC)Cl Chemical compound C(CCC)[P](CCCC)(CCCC)Cl MLWFBWIFQSUPAW-UHFFFAOYSA-N 0.000 claims description 3
- WFSAYLLJLHVNFM-UHFFFAOYSA-N C[P](C)(C)Br Chemical compound C[P](C)(C)Br WFSAYLLJLHVNFM-UHFFFAOYSA-N 0.000 claims description 3
- FQTLIQPLPGERTB-UHFFFAOYSA-N C[P](C)(C)Cl Chemical compound C[P](C)(C)Cl FQTLIQPLPGERTB-UHFFFAOYSA-N 0.000 claims description 3
- WYGVRVDZSPABJU-UHFFFAOYSA-N Cl[P](c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound Cl[P](c1ccccc1)(c1ccccc1)c1ccccc1 WYGVRVDZSPABJU-UHFFFAOYSA-N 0.000 claims description 3
- ZBOYXHKQAOMBEM-UHFFFAOYSA-N OP(O)=O.OC(=O)C1=CC=CC=N1 Chemical class OP(O)=O.OC(=O)C1=CC=CC=N1 ZBOYXHKQAOMBEM-UHFFFAOYSA-N 0.000 claims description 3
- IBJKYZKIUJRBCA-UHFFFAOYSA-N P(O)(O)=O.C(=O)[O-].[NH2+]1C=NC=C1 Chemical class P(O)(O)=O.C(=O)[O-].[NH2+]1C=NC=C1 IBJKYZKIUJRBCA-UHFFFAOYSA-N 0.000 claims description 3
- LTGAFSUCOWTLKW-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)O.N1=NC=CC=C1 Chemical class P(O)(O)=O.C(C)(=O)O.N1=NC=CC=C1 LTGAFSUCOWTLKW-UHFFFAOYSA-N 0.000 claims description 3
- SUBNFXGKKIUIJM-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)O.N1CCCC1 Chemical class P(O)(O)=O.C(C)(=O)O.N1CCCC1 SUBNFXGKKIUIJM-UHFFFAOYSA-N 0.000 claims description 3
- NISRCYJHMOTDSM-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].C(C)[PH+](CC)CC Chemical class P(O)(O)=O.C(C)(=O)[O-].C(C)[PH+](CC)CC NISRCYJHMOTDSM-UHFFFAOYSA-N 0.000 claims description 3
- UPZKNPWKAKSKHA-UHFFFAOYSA-M P(O)(O)=O.C(C)(=O)[O-].C(CC)[P+](CCC)CCC Chemical class P(O)(O)=O.C(C)(=O)[O-].C(CC)[P+](CCC)CCC UPZKNPWKAKSKHA-UHFFFAOYSA-M 0.000 claims description 3
- JIUZJMSEPMZQKH-UHFFFAOYSA-M P(O)(O)=O.C(C)(=O)[O-].C(CCC)[P+](CCCC)CCCC Chemical class P(O)(O)=O.C(C)(=O)[O-].C(CCC)[P+](CCCC)CCCC JIUZJMSEPMZQKH-UHFFFAOYSA-M 0.000 claims description 3
- YJQUZWCODQZOOH-UHFFFAOYSA-M P(O)(O)=O.C(C)(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical class P(O)(O)=O.C(C)(=O)[O-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)C1=CC=CC=C1 YJQUZWCODQZOOH-UHFFFAOYSA-M 0.000 claims description 3
- SUZHBOFUCXEVSF-UHFFFAOYSA-M P(O)(O)=O.C(C)(=O)[O-].C[P+](C)C Chemical class P(O)(O)=O.C(C)(=O)[O-].C[P+](C)C SUZHBOFUCXEVSF-UHFFFAOYSA-M 0.000 claims description 3
- OYJMLIJZTPBUFB-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].O1C=[NH+]C=C1 Chemical class P(O)(O)=O.C(C)(=O)[O-].O1C=[NH+]C=C1 OYJMLIJZTPBUFB-UHFFFAOYSA-N 0.000 claims description 3
- ZOJBZHPORYPIMY-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH+]1=CC=NC=C1 Chemical class P(O)(O)=O.C(C)(=O)[O-].[NH+]1=CC=NC=C1 ZOJBZHPORYPIMY-UHFFFAOYSA-N 0.000 claims description 3
- HGNOFEQOLPEEAI-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCNCC1 Chemical class P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCNCC1 HGNOFEQOLPEEAI-UHFFFAOYSA-N 0.000 claims description 3
- PEYJXYPXWNXPCO-UHFFFAOYSA-N P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCOCC1 Chemical class P(O)(O)=O.C(C)(=O)[O-].[NH2+]1CCOCC1 PEYJXYPXWNXPCO-UHFFFAOYSA-N 0.000 claims description 3
- NVDPBYPCYNXUIL-UHFFFAOYSA-N P(O)(O)=O.C(CC)[P](CCC)(CCC)Br Chemical class P(O)(O)=O.C(CC)[P](CCC)(CCC)Br NVDPBYPCYNXUIL-UHFFFAOYSA-N 0.000 claims description 3
- OEBRHVVLSISFKE-UHFFFAOYSA-N P(O)(O)=O.C(CCC)[P](CCCC)(CCCC)Br Chemical class P(O)(O)=O.C(CCC)[P](CCCC)(CCCC)Br OEBRHVVLSISFKE-UHFFFAOYSA-N 0.000 claims description 3
- PWVOPGGKLRCVJD-UHFFFAOYSA-N P(O)(O)=O.C[P](C)(C)Br Chemical class P(O)(O)=O.C[P](C)(C)Br PWVOPGGKLRCVJD-UHFFFAOYSA-N 0.000 claims description 3
- SRIODAXQYDOJTH-UHFFFAOYSA-N P(O)(O)=O.N1(CCCC1)C(=O)O Chemical class P(O)(O)=O.N1(CCCC1)C(=O)O SRIODAXQYDOJTH-UHFFFAOYSA-N 0.000 claims description 3
- UDBKJFHDHXENKB-UHFFFAOYSA-N P(O)(O)=O.N1(CCCCC1)C(=O)O Chemical class P(O)(O)=O.N1(CCCCC1)C(=O)O UDBKJFHDHXENKB-UHFFFAOYSA-N 0.000 claims description 3
- LGRWABOBZRGUMQ-UHFFFAOYSA-N P(O)(O)=O.N1(CCCCC1)CC(=O)O Chemical class P(O)(O)=O.N1(CCCCC1)CC(=O)O LGRWABOBZRGUMQ-UHFFFAOYSA-N 0.000 claims description 3
- LOOARSKCXMPOQY-UHFFFAOYSA-N P(O)(O)=O.N1(CCNCC1)C(=O)O Chemical class P(O)(O)=O.N1(CCNCC1)C(=O)O LOOARSKCXMPOQY-UHFFFAOYSA-N 0.000 claims description 3
- BMLITVPFBMEPNI-UHFFFAOYSA-N P(O)(O)=O.N1=C(C=NC=C1)C(=O)O Chemical class P(O)(O)=O.N1=C(C=NC=C1)C(=O)O BMLITVPFBMEPNI-UHFFFAOYSA-N 0.000 claims description 3
- CUQVLASSBWFCQY-UHFFFAOYSA-N P(O)(O)=O.N1=C(N=CC=C1)C(=O)O Chemical class P(O)(O)=O.N1=C(N=CC=C1)C(=O)O CUQVLASSBWFCQY-UHFFFAOYSA-N 0.000 claims description 3
- JUGRWPUMVMEPIM-UHFFFAOYSA-N P(O)(O)=O.N1C(=NC=C1)CC(=O)O Chemical class P(O)(O)=O.N1C(=NC=C1)CC(=O)O JUGRWPUMVMEPIM-UHFFFAOYSA-N 0.000 claims description 3
- JBBDOUXTQSOVJU-UHFFFAOYSA-N P(O)(O)=O.N1N=C(C=C1)C(=O)O Chemical class P(O)(O)=O.N1N=C(C=C1)C(=O)O JBBDOUXTQSOVJU-UHFFFAOYSA-N 0.000 claims description 3
- GFJLKDVDKUWICX-UHFFFAOYSA-N P(O)(O)=O.N1N=C(C=C1)CC(=O)O Chemical class P(O)(O)=O.N1N=C(C=C1)CC(=O)O GFJLKDVDKUWICX-UHFFFAOYSA-N 0.000 claims description 3
- JQKOJQKMBJBFJZ-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.C(C)P(CC)CC Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.C(C)P(CC)CC JQKOJQKMBJBFJZ-UHFFFAOYSA-N 0.000 claims description 3
- GECWHDSNPSYRSZ-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=CC=CC=C1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=CC=CC=C1 GECWHDSNPSYRSZ-UHFFFAOYSA-N 0.000 claims description 3
- LUVYTLIATCFYTA-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=CC=NC=C1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=CC=NC=C1 LUVYTLIATCFYTA-UHFFFAOYSA-N 0.000 claims description 3
- HSQORIJEVITJTM-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=CN=CC=C1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=CN=CC=C1 HSQORIJEVITJTM-UHFFFAOYSA-N 0.000 claims description 3
- XNWPOCVEPKIEJP-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=NC=CC=C1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1=NC=CC=C1 XNWPOCVEPKIEJP-UHFFFAOYSA-N 0.000 claims description 3
- FQJNZWFSDYEFCP-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1CCNCC1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1CCNCC1 FQJNZWFSDYEFCP-UHFFFAOYSA-N 0.000 claims description 3
- OOQNGVYZSGKDCZ-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1CCOCC1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.N1CCOCC1 OOQNGVYZSGKDCZ-UHFFFAOYSA-N 0.000 claims description 3
- WAZJDXKKWXPRIS-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.O1C=NC=C1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.O1C=NC=C1 WAZJDXKKWXPRIS-UHFFFAOYSA-N 0.000 claims description 3
- MILONQLEQUCXNI-UHFFFAOYSA-N P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.S1C=NC=C1 Chemical class P(O)(O)=O.S(=O)(=O)(O)OS(=O)(=O)O.S1C=NC=C1 MILONQLEQUCXNI-UHFFFAOYSA-N 0.000 claims description 3
- FFEXEEDRBKOZNV-UHFFFAOYSA-N P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1C=NC=C1 Chemical class P(O)(O)=O.S([O-])(O)(=O)=O.[NH2+]1C=NC=C1 FFEXEEDRBKOZNV-UHFFFAOYSA-N 0.000 claims description 3
- FOTIAQAXDQHWMT-UHFFFAOYSA-N P(O)(O)=O.[Br-].C(C)[PH+](CC)CC Chemical class P(O)(O)=O.[Br-].C(C)[PH+](CC)CC FOTIAQAXDQHWMT-UHFFFAOYSA-N 0.000 claims description 3
- TYWCHXFNAMLGGW-UHFFFAOYSA-N P(O)(O)=O.[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical class P(O)(O)=O.[Br-].C1(=CC=CC=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 TYWCHXFNAMLGGW-UHFFFAOYSA-N 0.000 claims description 3
- GPJKGESVQXXVLJ-UHFFFAOYSA-N P(O)(O)=O.[Br-].O1C=[NH+]C=C1 Chemical class P(O)(O)=O.[Br-].O1C=[NH+]C=C1 GPJKGESVQXXVLJ-UHFFFAOYSA-N 0.000 claims description 3
- SGDDQOUURAJPTM-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=CC=CC=C1 Chemical class P(O)(O)=O.[Br-].[NH+]1=CC=CC=C1 SGDDQOUURAJPTM-UHFFFAOYSA-N 0.000 claims description 3
- JMAVPDOTVKBPBP-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=CC=NC=C1 Chemical class P(O)(O)=O.[Br-].[NH+]1=CC=NC=C1 JMAVPDOTVKBPBP-UHFFFAOYSA-N 0.000 claims description 3
- ZIEIZZGRJQZSCC-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=CN=CC=C1 Chemical class P(O)(O)=O.[Br-].[NH+]1=CN=CC=C1 ZIEIZZGRJQZSCC-UHFFFAOYSA-N 0.000 claims description 3
- YTUQPUVGVWYQSD-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH+]1=NC=CC=C1 Chemical class P(O)(O)=O.[Br-].[NH+]1=NC=CC=C1 YTUQPUVGVWYQSD-UHFFFAOYSA-N 0.000 claims description 3
- XLDPXPLIIJHHNV-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1C=NC=C1 Chemical class P(O)(O)=O.[Br-].[NH2+]1C=NC=C1 XLDPXPLIIJHHNV-UHFFFAOYSA-N 0.000 claims description 3
- JNRZXYRADQMFCB-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1CCCCC1 Chemical class P(O)(O)=O.[Br-].[NH2+]1CCCCC1 JNRZXYRADQMFCB-UHFFFAOYSA-N 0.000 claims description 3
- GITSKEDWLCKCBS-UHFFFAOYSA-N P(O)(O)=O.[Br-].[NH2+]1CCOCC1 Chemical class P(O)(O)=O.[Br-].[NH2+]1CCOCC1 GITSKEDWLCKCBS-UHFFFAOYSA-N 0.000 claims description 3
- KOQKCMLVEPJDSA-UHFFFAOYSA-N P(O)(O)=O.[Cl-].C(C)[PH+](CC)CC Chemical class P(O)(O)=O.[Cl-].C(C)[PH+](CC)CC KOQKCMLVEPJDSA-UHFFFAOYSA-N 0.000 claims description 3
- ARTCSXGROPSDFG-UHFFFAOYSA-N P(O)(O)=O.[Cl-].O1C=[NH+]C=C1 Chemical class P(O)(O)=O.[Cl-].O1C=[NH+]C=C1 ARTCSXGROPSDFG-UHFFFAOYSA-N 0.000 claims description 3
- LKONHSOPBBGJGT-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=CC=CC=C1 Chemical class P(O)(O)=O.[Cl-].[NH+]1=CC=CC=C1 LKONHSOPBBGJGT-UHFFFAOYSA-N 0.000 claims description 3
- KWPNKJNMRVWXAS-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=CC=NC=C1 Chemical class P(O)(O)=O.[Cl-].[NH+]1=CC=NC=C1 KWPNKJNMRVWXAS-UHFFFAOYSA-N 0.000 claims description 3
- XTIVYCZPBBFVBF-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=CN=CC=C1 Chemical class P(O)(O)=O.[Cl-].[NH+]1=CN=CC=C1 XTIVYCZPBBFVBF-UHFFFAOYSA-N 0.000 claims description 3
- PXLXFQGGMCROFJ-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH+]1=NC=CC=C1 Chemical class P(O)(O)=O.[Cl-].[NH+]1=NC=CC=C1 PXLXFQGGMCROFJ-UHFFFAOYSA-N 0.000 claims description 3
- PCUPYNIYTUXSDN-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1C=NC=C1 Chemical class P(O)(O)=O.[Cl-].[NH2+]1C=NC=C1 PCUPYNIYTUXSDN-UHFFFAOYSA-N 0.000 claims description 3
- WWHDBDGILBIABS-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1CCCCC1 Chemical class P(O)(O)=O.[Cl-].[NH2+]1CCCCC1 WWHDBDGILBIABS-UHFFFAOYSA-N 0.000 claims description 3
- ACXUNMQXAWXTON-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1CCNCC1 Chemical class P(O)(O)=O.[Cl-].[NH2+]1CCNCC1 ACXUNMQXAWXTON-UHFFFAOYSA-N 0.000 claims description 3
- WVBJCDMWBKMKPU-UHFFFAOYSA-N P(O)(O)=O.[Cl-].[NH2+]1CCOCC1 Chemical class P(O)(O)=O.[Cl-].[NH2+]1CCOCC1 WVBJCDMWBKMKPU-UHFFFAOYSA-N 0.000 claims description 3
- QBNGTJAHSSTMDC-UHFFFAOYSA-N S(=O)(=O)(O)OS(=O)(=O)O.C(C)P(CC)CC Chemical compound S(=O)(=O)(O)OS(=O)(=O)O.C(C)P(CC)CC QBNGTJAHSSTMDC-UHFFFAOYSA-N 0.000 claims description 3
- MIUUJVQQMVSCLH-UHFFFAOYSA-N S(=O)(=O)(O)OS(=O)(=O)O.N1=CC=NC=C1 Chemical compound S(=O)(=O)(O)OS(=O)(=O)O.N1=CC=NC=C1 MIUUJVQQMVSCLH-UHFFFAOYSA-N 0.000 claims description 3
- GFYRTXXJOOPEKU-UHFFFAOYSA-N S(=O)(=O)(O)OS(=O)(=O)O.N1=NC=CC=C1 Chemical compound S(=O)(=O)(O)OS(=O)(=O)O.N1=NC=CC=C1 GFYRTXXJOOPEKU-UHFFFAOYSA-N 0.000 claims description 3
- GOOBJMUEOLKIBD-UHFFFAOYSA-N S(=O)(=O)(O)OS(=O)(=O)O.N1CCOCC1 Chemical compound S(=O)(=O)(O)OS(=O)(=O)O.N1CCOCC1 GOOBJMUEOLKIBD-UHFFFAOYSA-N 0.000 claims description 3
- RDFBOEWAEXZQGE-UHFFFAOYSA-N S(=O)(=O)(O)OS(=O)(=O)O.S1C=NC=C1 Chemical compound S(=O)(=O)(O)OS(=O)(=O)O.S1C=NC=C1 RDFBOEWAEXZQGE-UHFFFAOYSA-N 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- UXADJJRNJRDFHA-UHFFFAOYSA-N [P](Br)(F)(F)F Chemical compound [P](Br)(F)(F)F UXADJJRNJRDFHA-UHFFFAOYSA-N 0.000 claims description 3
- APFCBJSBVZAXQZ-UHFFFAOYSA-N [P](Cl)(F)(F)F Chemical compound [P](Cl)(F)(F)F APFCBJSBVZAXQZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 3
- MIJRUQYZDSEMBD-UHFFFAOYSA-N acetic acid;morpholine Chemical compound CC(O)=O.C1COCCN1 MIJRUQYZDSEMBD-UHFFFAOYSA-N 0.000 claims description 3
- LKWQRFNQTSFWHS-UHFFFAOYSA-N acetic acid;pyrazine Chemical compound CC(O)=O.C1=CN=CC=N1 LKWQRFNQTSFWHS-UHFFFAOYSA-N 0.000 claims description 3
- MCZPFWGNNYZODF-UHFFFAOYSA-N acetic acid;pyridazine Chemical compound CC(O)=O.C1=CC=NN=C1 MCZPFWGNNYZODF-UHFFFAOYSA-N 0.000 claims description 3
- YAXGXEOYWAIEER-UHFFFAOYSA-N acetic acid;triethylphosphane Chemical compound CC([O-])=O.CC[PH+](CC)CC YAXGXEOYWAIEER-UHFFFAOYSA-N 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 150000001649 bromium compounds Chemical class 0.000 claims description 3
- CMDZOENGSXWINU-UHFFFAOYSA-N c1cncnc1.OS(=O)(=O)OS(O)(=O)=O Chemical compound c1cncnc1.OS(=O)(=O)OS(O)(=O)=O CMDZOENGSXWINU-UHFFFAOYSA-N 0.000 claims description 3
- FPLYVOGUMSEZCO-UHFFFAOYSA-N c1cocn1.OS(=O)(=O)OS(O)(=O)=O Chemical compound c1cocn1.OS(=O)(=O)OS(O)(=O)=O FPLYVOGUMSEZCO-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 229910052570 clay Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- PQWGEGZUHVGSKG-UHFFFAOYSA-N formic acid;1,3-oxazole Chemical class OC=O.C1=COC=N1 PQWGEGZUHVGSKG-UHFFFAOYSA-N 0.000 claims description 3
- BJFIGCBESRQZMQ-UHFFFAOYSA-N formic acid;1h-imidazole Chemical compound OC=O.C1=CNC=N1 BJFIGCBESRQZMQ-UHFFFAOYSA-N 0.000 claims description 3
- BDHPJXPOQGPUNI-UHFFFAOYSA-N formic acid;morpholine Chemical class [O-]C=O.C1COCC[NH2+]1 BDHPJXPOQGPUNI-UHFFFAOYSA-N 0.000 claims description 3
- GEMITLJMEMBDKW-UHFFFAOYSA-N hydrogen sulfate;1h-imidazol-3-ium Chemical compound C1=CNC=N1.OS(O)(=O)=O GEMITLJMEMBDKW-UHFFFAOYSA-N 0.000 claims description 3
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 claims description 3
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 claims description 3
- VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical compound [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 claims description 3
- WUJUYHMGDPTLMG-UHFFFAOYSA-N imidazol-2-ylacetic acid Chemical class OC(=O)CC1=NC=CN1 WUJUYHMGDPTLMG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- 239000000391 magnesium silicate Substances 0.000 claims description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 3
- 235000019792 magnesium silicate Nutrition 0.000 claims description 3
- BVJOXYJFOYNQRB-UHFFFAOYSA-N morpholine;hydrobromide Chemical compound Br.C1COCCN1 BVJOXYJFOYNQRB-UHFFFAOYSA-N 0.000 claims description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 3
- OSHVGUAPPIYWIS-UHFFFAOYSA-N piperazin-1-ium;acetate Chemical compound CC(O)=O.C1CNCCN1 OSHVGUAPPIYWIS-UHFFFAOYSA-N 0.000 claims description 3
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical class OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 3
- CQRIRCHDGWOACT-UHFFFAOYSA-N piperazine;sulfo hydrogen sulfate Chemical compound C1CNCCN1.OS(=O)(=O)OS(O)(=O)=O CQRIRCHDGWOACT-UHFFFAOYSA-N 0.000 claims description 3
- ROFVJSWBDQUQGW-UHFFFAOYSA-N piperidin-1-ium;bromide Chemical compound Br.C1CCNCC1 ROFVJSWBDQUQGW-UHFFFAOYSA-N 0.000 claims description 3
- HYHBKLWDTGTBME-UHFFFAOYSA-N pyrazin-1-ium;chloride Chemical compound Cl.C1=CN=CC=N1 HYHBKLWDTGTBME-UHFFFAOYSA-N 0.000 claims description 3
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical class OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 3
- KNBMYMNEEGYSMP-UHFFFAOYSA-N pyrazine;hydrobromide Chemical compound [Br-].C1=C[NH+]=CC=N1 KNBMYMNEEGYSMP-UHFFFAOYSA-N 0.000 claims description 3
- HATXXVNYNPECAD-UHFFFAOYSA-N pyridazin-1-ium;bromide Chemical compound [Br-].C1=CC=[NH+]N=C1 HATXXVNYNPECAD-UHFFFAOYSA-N 0.000 claims description 3
- WFJZBOIOPMOUCB-UHFFFAOYSA-N pyridazine;hydrochloride Chemical compound Cl.C1=CC=NN=C1 WFJZBOIOPMOUCB-UHFFFAOYSA-N 0.000 claims description 3
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims description 3
- AJTWAFXXIGBVRF-UHFFFAOYSA-N pyridine;sulfo hydrogen sulfate Chemical compound C1=CC=NC=C1.OS(=O)(=O)OS(O)(=O)=O AJTWAFXXIGBVRF-UHFFFAOYSA-N 0.000 claims description 3
- WRMCZHYLTVSDQU-UHFFFAOYSA-N pyrimidin-1-ium;acetate Chemical compound CC(O)=O.C1=CN=CN=C1 WRMCZHYLTVSDQU-UHFFFAOYSA-N 0.000 claims description 3
- BATMYWDOUUWCJE-UHFFFAOYSA-N pyrimidin-1-ium;bromide Chemical compound Br.C1=CN=CN=C1 BATMYWDOUUWCJE-UHFFFAOYSA-N 0.000 claims description 3
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 claims description 3
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 claims description 3
- NCHPDGCQTUJYKK-UHFFFAOYSA-N pyrrolidin-1-ium;acetate Chemical compound CC(O)=O.C1CCNC1 NCHPDGCQTUJYKK-UHFFFAOYSA-N 0.000 claims description 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- PRYDGNPXVINHFJ-UHFFFAOYSA-N triethylphosphane;hydrobromide Chemical compound [Br-].CC[PH+](CC)CC PRYDGNPXVINHFJ-UHFFFAOYSA-N 0.000 claims description 3
- NXPYHCCOHHNZNF-UHFFFAOYSA-N triethylphosphane;hydrochloride Chemical compound [Cl-].CC[PH+](CC)CC NXPYHCCOHHNZNF-UHFFFAOYSA-N 0.000 claims description 3
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- LYLDIIUFTYRPPK-UHFFFAOYSA-N 1h-imidazole-2-sulfonic acid Chemical compound OS(=O)(=O)C1=NC=CN1 LYLDIIUFTYRPPK-UHFFFAOYSA-N 0.000 claims description 2
- 150000004880 oxines Chemical class 0.000 claims 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 239000000376 reactant Substances 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 44
- 229920001542 oligosaccharide Polymers 0.000 abstract description 19
- 150000002482 oligosaccharides Chemical class 0.000 abstract description 18
- 230000002255 enzymatic effect Effects 0.000 abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 150000002772 monosaccharides Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 354
- 239000000178 monomer Substances 0.000 description 281
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 142
- 229920002554 vinyl polymer Polymers 0.000 description 81
- 239000002585 base Substances 0.000 description 56
- 239000010902 straw Substances 0.000 description 50
- 229910052739 hydrogen Inorganic materials 0.000 description 48
- 229920002678 cellulose Polymers 0.000 description 46
- 239000001913 cellulose Substances 0.000 description 46
- 235000010980 cellulose Nutrition 0.000 description 46
- 239000001257 hydrogen Substances 0.000 description 45
- 239000007787 solid Substances 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 36
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 36
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 36
- 229920002488 Hemicellulose Polymers 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 33
- 239000000126 substance Substances 0.000 description 32
- 125000004429 atom Chemical group 0.000 description 31
- 125000005842 heteroatom Chemical group 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 125000000304 alkynyl group Chemical group 0.000 description 29
- 235000001950 Elaeis guineensis Nutrition 0.000 description 28
- 240000008042 Zea mays Species 0.000 description 28
- 239000011121 hardwood Substances 0.000 description 28
- 241000609240 Ambelania acida Species 0.000 description 27
- 240000003183 Manihot esculenta Species 0.000 description 27
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 27
- 239000010905 bagasse Substances 0.000 description 27
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 27
- 238000006460 hydrolysis reaction Methods 0.000 description 27
- 239000011122 softwood Substances 0.000 description 27
- 244000127993 Elaeis melanococca Species 0.000 description 26
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 26
- 235000009973 maize Nutrition 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 230000007062 hydrolysis Effects 0.000 description 25
- 235000013405 beer Nutrition 0.000 description 23
- 238000001976 enzyme digestion Methods 0.000 description 23
- 125000005843 halogen group Chemical group 0.000 description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 22
- 239000001301 oxygen Substances 0.000 description 22
- 229910052760 oxygen Inorganic materials 0.000 description 22
- 239000013049 sediment Substances 0.000 description 22
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 21
- 125000004043 oxo group Chemical group O=* 0.000 description 21
- 239000000123 paper Substances 0.000 description 21
- 238000002203 pretreatment Methods 0.000 description 21
- 125000002947 alkylene group Chemical group 0.000 description 20
- 125000001188 haloalkyl group Chemical group 0.000 description 20
- 239000002245 particle Substances 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 239000010802 sludge Substances 0.000 description 20
- 235000013305 food Nutrition 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 229910021529 ammonia Inorganic materials 0.000 description 18
- 239000000835 fiber Substances 0.000 description 18
- 239000002023 wood Substances 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 239000011162 core material Substances 0.000 description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 description 15
- 238000004880 explosion Methods 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- 239000001273 butane Substances 0.000 description 12
- 125000001165 hydrophobic group Chemical group 0.000 description 12
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 12
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 238000009279 wet oxidation reaction Methods 0.000 description 11
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 10
- 241000018646 Pinus brutia Species 0.000 description 10
- 235000011613 Pinus brutia Nutrition 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 229920005610 lignin Polymers 0.000 description 9
- 239000005864 Sulphur Substances 0.000 description 8
- 240000006909 Tilia x europaea Species 0.000 description 8
- 230000029087 digestion Effects 0.000 description 8
- 125000006574 non-aromatic ring group Chemical group 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 7
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 7
- 235000011941 Tilia x europaea Nutrition 0.000 description 7
- SRBFZHDQGSBBOR-LECHCGJUSA-N alpha-D-xylose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-LECHCGJUSA-N 0.000 description 7
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 7
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 7
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 7
- 239000004571 lime Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 229960003487 xylose Drugs 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- 229930091371 Fructose Natural products 0.000 description 6
- 239000005715 Fructose Substances 0.000 description 6
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000006213 oxygenation reaction Methods 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 235000018185 Betula X alpestris Nutrition 0.000 description 5
- 235000018212 Betula X uliginosa Nutrition 0.000 description 5
- 244000301850 Cupressus sempervirens Species 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 240000007049 Juglans regia Species 0.000 description 5
- 235000009496 Juglans regia Nutrition 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 241000219000 Populus Species 0.000 description 5
- 241000219492 Quercus Species 0.000 description 5
- 235000016976 Quercus macrolepis Nutrition 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 238000010923 batch production Methods 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 239000000446 fuel Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000012978 lignocellulosic material Substances 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 235000007173 Abies balsamea Nutrition 0.000 description 4
- 241000208140 Acer Species 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000183024 Populus tremula Species 0.000 description 4
- 240000000111 Saccharum officinarum Species 0.000 description 4
- 241001106462 Ulmus Species 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000002551 biofuel Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 238000004520 electroporation Methods 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229920000140 heteropolymer Polymers 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- 229920000554 ionomer Polymers 0.000 description 4
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000009996 mechanical pre-treatment Methods 0.000 description 4
- 125000005981 pentynyl group Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000012552 review Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 241000723418 Carya Species 0.000 description 3
- 241000370738 Chlorion Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 235000003385 Diospyros ebenum Nutrition 0.000 description 3
- 241000792913 Ebenaceae Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000017339 Pinus palustris Nutrition 0.000 description 3
- 241000168036 Populus alba Species 0.000 description 3
- 229920001131 Pulp (paper) Polymers 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 244000004774 Sabina virginiana Species 0.000 description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 3
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 3
- 239000004914 cyclooctane Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000007071 enzymatic hydrolysis Effects 0.000 description 3
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 3
- 230000036252 glycation Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000005956 isoquinolyl group Chemical group 0.000 description 3
- 239000002029 lignocellulosic biomass Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000000696 magnetic material Substances 0.000 description 3
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 3
- 238000007781 pre-processing Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003214 pyranose derivatives Chemical class 0.000 description 3
- 150000003233 pyrroles Chemical class 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 235000001520 savin Nutrition 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 235000020234 walnut Nutrition 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- 244000283070 Abies balsamea Species 0.000 description 2
- 235000004422 Acer negundo Nutrition 0.000 description 2
- 244000046151 Acer negundo Species 0.000 description 2
- 235000010328 Acer nigrum Nutrition 0.000 description 2
- 235000002629 Acer saccharinum Nutrition 0.000 description 2
- 244000046139 Acer saccharum Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000014036 Castanea Nutrition 0.000 description 2
- 241001070941 Castanea Species 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- 241001480079 Corymbia calophylla Species 0.000 description 2
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 2
- 235000018783 Dacrycarpus dacrydioides Nutrition 0.000 description 2
- 235000014466 Douglas bleu Nutrition 0.000 description 2
- 240000003133 Elaeis guineensis Species 0.000 description 2
- 235000004692 Eucalyptus globulus Nutrition 0.000 description 2
- 235000019134 Eucalyptus tereticornis Nutrition 0.000 description 2
- 241000221017 Euphorbiaceae Species 0.000 description 2
- 240000000731 Fagus sylvatica Species 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 235000005590 Larix decidua Nutrition 0.000 description 2
- 235000006552 Liquidambar styraciflua Nutrition 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 241000878006 Miscanthus sinensis Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 241001520808 Panicum virgatum Species 0.000 description 2
- 235000008124 Picea excelsa Nutrition 0.000 description 2
- 240000007320 Pinus strobus Species 0.000 description 2
- 235000008578 Pinus strobus Nutrition 0.000 description 2
- 235000008566 Pinus taeda Nutrition 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 240000001987 Pyrus communis Species 0.000 description 2
- 235000014443 Pyrus communis Nutrition 0.000 description 2
- 241000124033 Salix Species 0.000 description 2
- 102400000830 Saposin-B Human genes 0.000 description 2
- 101800001697 Saposin-B Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000332824 Tsuga chinensis Species 0.000 description 2
- 235000010183 Tsuga mertensiana Nutrition 0.000 description 2
- 244000078534 Vaccinium myrtillus Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001298 alcohols Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001538 azepines Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000010364 biochemical engineering Methods 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 230000007073 chemical hydrolysis Effects 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 239000006063 cullet Substances 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000005672 electromagnetic field Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 125000000232 haloalkynyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052680 mordenite Inorganic materials 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 239000011295 pitch Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 150000004804 polysaccharides Chemical class 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229920001221 xylan Polymers 0.000 description 2
- 150000004823 xylans Chemical class 0.000 description 2
- TWNIBLMWSKIRAT-RWOPYEJCSA-N (1r,2s,3s,4s,5r)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol Chemical compound O1[C@@]2([H])OC[C@]1([H])[C@@H](O)[C@H](O)[C@@H]2O TWNIBLMWSKIRAT-RWOPYEJCSA-N 0.000 description 1
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- CZWSZZHGSNZRMW-UHFFFAOYSA-N 1,2-dibromobutane Chemical compound CCC(Br)CBr CZWSZZHGSNZRMW-UHFFFAOYSA-N 0.000 description 1
- CITMYAPULDSOHG-UHFFFAOYSA-N 1,2-dibromopentane Chemical compound CCCC(Br)CBr CITMYAPULDSOHG-UHFFFAOYSA-N 0.000 description 1
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- PPLBPDUKNRCHGG-UHFFFAOYSA-N 1,2-dichloropentane Chemical compound CCCC(Cl)CCl PPLBPDUKNRCHGG-UHFFFAOYSA-N 0.000 description 1
- MIAAQPQIWLWRSI-UHFFFAOYSA-N 1,2-diiodobutane Chemical compound CCC(I)CI MIAAQPQIWLWRSI-UHFFFAOYSA-N 0.000 description 1
- RJJBMBXTBVCMND-UHFFFAOYSA-N 1,2-diiodopentane Chemical compound CCCC(I)CI RJJBMBXTBVCMND-UHFFFAOYSA-N 0.000 description 1
- ISXPOEJSKALLKA-UHFFFAOYSA-N 1,2-diiodopropane Chemical compound CC(I)CI ISXPOEJSKALLKA-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- XZNGUVQDFJHPLU-UHFFFAOYSA-N 1,3-dibromobutane Chemical compound CC(Br)CCBr XZNGUVQDFJHPLU-UHFFFAOYSA-N 0.000 description 1
- SOZLNIPBRVQUOG-UHFFFAOYSA-N 1,3-dibromopentane Chemical compound CCC(Br)CCBr SOZLNIPBRVQUOG-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- QMLLRWZQACTYAX-UHFFFAOYSA-N 1,3-dichloropentane Chemical compound CCC(Cl)CCCl QMLLRWZQACTYAX-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- ZFMSVHPAOMPMMF-UHFFFAOYSA-N 1,3-diiodobutane Chemical compound CC(I)CCI ZFMSVHPAOMPMMF-UHFFFAOYSA-N 0.000 description 1
- GHRIWTBUXMUHJM-UHFFFAOYSA-N 1,3-diiodopentane Chemical compound CCC(I)CCI GHRIWTBUXMUHJM-UHFFFAOYSA-N 0.000 description 1
- AAAXMNYUNVCMCJ-UHFFFAOYSA-N 1,3-diiodopropane Chemical compound ICCCI AAAXMNYUNVCMCJ-UHFFFAOYSA-N 0.000 description 1
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- CNBFRBXEGGRSPL-UHFFFAOYSA-N 1,4-dibromopentane Chemical compound CC(Br)CCCBr CNBFRBXEGGRSPL-UHFFFAOYSA-N 0.000 description 1
- IJZUPZAYWWVHIO-UHFFFAOYSA-N 1,4-dichloropentane Chemical compound CC(Cl)CCCCl IJZUPZAYWWVHIO-UHFFFAOYSA-N 0.000 description 1
- ROUYUBHVBIKMQO-UHFFFAOYSA-N 1,4-diiodobutane Chemical compound ICCCCI ROUYUBHVBIKMQO-UHFFFAOYSA-N 0.000 description 1
- CKTWXVLPFHHXEW-UHFFFAOYSA-N 1,4-diiodopentane Chemical compound CC(I)CCCI CKTWXVLPFHHXEW-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- LBKDGROORAKTLC-UHFFFAOYSA-N 1,5-dichloropentane Chemical compound ClCCCCCCl LBKDGROORAKTLC-UHFFFAOYSA-N 0.000 description 1
- IAEOYUUPFYJXHN-UHFFFAOYSA-N 1,5-diiodopentane Chemical compound ICCCCCI IAEOYUUPFYJXHN-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- LTFBFZBWUKWXID-UHFFFAOYSA-N 1h-cyclopenta[d]pyrimidine Chemical compound N1=CNC2=CC=CC2=C1 LTFBFZBWUKWXID-UHFFFAOYSA-N 0.000 description 1
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 1
- PHIMVUDMARQXAQ-UHFFFAOYSA-N 1h-pyrrole-2,3-diamine Chemical class NC=1C=CNC=1N PHIMVUDMARQXAQ-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003504 2-oxazolinyl group Polymers O1C(=NCC1)* 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical class C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 1
- BHZUNHXTRRNKST-UHFFFAOYSA-N 3,3-dimethylpenta-1,4-diene Chemical compound C=CC(C)(C)C=C BHZUNHXTRRNKST-UHFFFAOYSA-N 0.000 description 1
- BKVALJGAKNDDJJ-UHFFFAOYSA-N 3,4-dimethylhexa-1,5-diene Chemical compound C=CC(C)C(C)C=C BKVALJGAKNDDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- IKQUUYYDRTYXAP-UHFFFAOYSA-N 3-methylpenta-1,4-diene Chemical compound C=CC(C)C=C IKQUUYYDRTYXAP-UHFFFAOYSA-N 0.000 description 1
- DIIKLBOLDNKFBV-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine Chemical compound S1C2=NC=NC=C2C2=C1CCCC2 DIIKLBOLDNKFBV-UHFFFAOYSA-N 0.000 description 1
- SMSHIXOEBWOYJS-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinazoline Chemical compound C1=NC=C2CCCCC2=N1 SMSHIXOEBWOYJS-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QLINOSPZDHPWIV-UHFFFAOYSA-N 6h-benzo[b][1,4]benzodioxepine Chemical compound C1OC2=CC=CC=C2OC2=CC=CC=C12 QLINOSPZDHPWIV-UHFFFAOYSA-N 0.000 description 1
- ZDONPXIOHABCEA-UHFFFAOYSA-N 7,8-dihydro-6h-cyclopenta[4,5]thieno[1,2-b]pyrimidine Chemical compound S1C2=NC=NC=C2C2=C1CCC2 ZDONPXIOHABCEA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000004507 Abies alba Nutrition 0.000 description 1
- 244000178606 Abies grandis Species 0.000 description 1
- 235000017894 Abies grandis Nutrition 0.000 description 1
- 235000004710 Abies lasiocarpa Nutrition 0.000 description 1
- 241000379225 Abies procera Species 0.000 description 1
- 240000005020 Acaciella glauca Species 0.000 description 1
- 235000010319 Acer grandidentatum Nutrition 0.000 description 1
- 244000205124 Acer nigrum Species 0.000 description 1
- 240000004144 Acer rubrum Species 0.000 description 1
- 235000011772 Acer rubrum var tomentosum Nutrition 0.000 description 1
- 235000009057 Acer rubrum var tridens Nutrition 0.000 description 1
- 235000004421 Acer saccharum Nutrition 0.000 description 1
- 235000010157 Acer saccharum subsp saccharum Nutrition 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000157280 Aesculus hippocastanum Species 0.000 description 1
- 241001564395 Alnus rubra Species 0.000 description 1
- 235000018719 Araucaria angustifolia Nutrition 0.000 description 1
- 240000000940 Araucaria angustifolia Species 0.000 description 1
- 240000007414 Araucaria araucana Species 0.000 description 1
- 244000178400 Araucaria cunninghamii Species 0.000 description 1
- 241000870566 Astronium fraxinifolium Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000189108 Betula alleghaniensis Species 0.000 description 1
- 235000018199 Betula alleghaniensis var. alleghaniensis Nutrition 0.000 description 1
- 235000018198 Betula alleghaniensis var. macrolepis Nutrition 0.000 description 1
- 235000009131 Betula nigra Nutrition 0.000 description 1
- 244000276440 Betula nigra Species 0.000 description 1
- 235000018720 Betula occidentalis Nutrition 0.000 description 1
- 235000009109 Betula pendula Nutrition 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- 241001333452 Bridelia insulana Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001656898 Buxus microphylla Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000012254 Canarium album Species 0.000 description 1
- 235000009103 Canarium album Nutrition 0.000 description 1
- 241001600425 Carpinus turczaninovii Species 0.000 description 1
- 235000005662 Carya cordiformis Nutrition 0.000 description 1
- 240000002112 Carya glabra Species 0.000 description 1
- 235000007890 Carya glabra var. glabra Nutrition 0.000 description 1
- 235000014669 Carya glabra var. hirsuta Nutrition 0.000 description 1
- 235000014667 Carya glabra var. megacarpa Nutrition 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- 241001264786 Ceanothus spinosus Species 0.000 description 1
- 235000001808 Ceanothus spinosus Nutrition 0.000 description 1
- 240000008444 Celtis occidentalis Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 244000117493 Colubrina ferruginosa Species 0.000 description 1
- 235000008542 Colubrina ferruginosa Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000005109 Cryptomeria japonica Species 0.000 description 1
- 244000050510 Cunninghamia lanceolata Species 0.000 description 1
- 241000218916 Cycas Species 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 description 1
- 244000288671 Dacrycarpus dacrydioides Species 0.000 description 1
- 235000018782 Dacrydium cupressinum Nutrition 0.000 description 1
- 240000006055 Dacrydium cupressinum Species 0.000 description 1
- 241000196359 Dalbergia melanoxylon Species 0.000 description 1
- 241000746418 Dalbergia nigra Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 244000279080 Douglas bleu Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 241000006109 Eucalyptus delegatensis Species 0.000 description 1
- 240000006934 Eucalyptus pilularis Species 0.000 description 1
- 235000018241 Fagus americana Nutrition 0.000 description 1
- 244000222296 Fagus americana Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 235000004994 Fagus sylvatica subsp sylvatica Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241000931143 Gleditsia sinensis Species 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 229910001060 Gray iron Inorganic materials 0.000 description 1
- 244000021988 Grevillea robusta Species 0.000 description 1
- 235000019027 Grevillea robusta Nutrition 0.000 description 1
- 241000190019 Guaiacum Species 0.000 description 1
- 235000004440 Guaiacum sanctum Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 240000000797 Hibiscus cannabinus Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000003325 Ilex Nutrition 0.000 description 1
- 241000209035 Ilex Species 0.000 description 1
- 235000003338 Ilex verticillata Nutrition 0.000 description 1
- 244000188413 Ilex verticillata Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000014056 Juglans cinerea Nutrition 0.000 description 1
- 240000004929 Juglans cinerea Species 0.000 description 1
- 244000264601 Juglans mandschurica Species 0.000 description 1
- 235000014075 Juglans mandschurica Nutrition 0.000 description 1
- 235000013740 Juglans nigra Nutrition 0.000 description 1
- 244000184861 Juglans nigra Species 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 241001235216 Larix decidua Species 0.000 description 1
- 235000008119 Larix laricina Nutrition 0.000 description 1
- 241000218653 Larix laricina Species 0.000 description 1
- 235000008122 Larix occidentalis Nutrition 0.000 description 1
- 244000193510 Larix occidentalis Species 0.000 description 1
- 241001675026 Larix potaninii Species 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000893545 Liquidambar formosana Species 0.000 description 1
- 235000008512 Magnolia grandiflora Nutrition 0.000 description 1
- 240000003293 Magnolia grandiflora Species 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 235000004456 Manihot esculenta Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 235000000380 Nyssa aquatica Nutrition 0.000 description 1
- 240000005295 Nyssa aquatica Species 0.000 description 1
- 241000392928 Parachromis friedrichsthalii Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241001364904 Phyllocladus toatoa Species 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 241000351396 Picea asperata Species 0.000 description 1
- 244000193463 Picea excelsa Species 0.000 description 1
- 235000008127 Picea glauca Nutrition 0.000 description 1
- 240000009002 Picea mariana Species 0.000 description 1
- 235000008145 Picea mariana Nutrition 0.000 description 1
- 241000218596 Picea rubens Species 0.000 description 1
- 241000218595 Picea sitchensis Species 0.000 description 1
- 241001555133 Picrodendron baccatum Species 0.000 description 1
- 235000008565 Pinus banksiana Nutrition 0.000 description 1
- 241000218680 Pinus banksiana Species 0.000 description 1
- 235000009324 Pinus caribaea Nutrition 0.000 description 1
- 244000083281 Pinus coulteri Species 0.000 description 1
- 235000008568 Pinus coulteri Nutrition 0.000 description 1
- 235000000405 Pinus densiflora Nutrition 0.000 description 1
- 240000008670 Pinus densiflora Species 0.000 description 1
- 235000005018 Pinus echinata Nutrition 0.000 description 1
- 241001236219 Pinus echinata Species 0.000 description 1
- 235000011334 Pinus elliottii Nutrition 0.000 description 1
- 244000019397 Pinus jeffreyi Species 0.000 description 1
- 235000008595 Pinus lambertiana Nutrition 0.000 description 1
- 240000008299 Pinus lambertiana Species 0.000 description 1
- 241000204936 Pinus palustris Species 0.000 description 1
- 235000013267 Pinus ponderosa Nutrition 0.000 description 1
- 235000013269 Pinus ponderosa var ponderosa Nutrition 0.000 description 1
- 235000013268 Pinus ponderosa var scopulorum Nutrition 0.000 description 1
- 235000007738 Pinus rigida Nutrition 0.000 description 1
- 241000218679 Pinus taeda Species 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 241000218982 Populus nigra Species 0.000 description 1
- 235000011263 Populus tremuloides Nutrition 0.000 description 1
- 240000004923 Populus tremuloides Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000001416 Pseudotsuga menziesii Species 0.000 description 1
- 235000005386 Pseudotsuga menziesii var menziesii Nutrition 0.000 description 1
- 235000009984 Pterocarpus indicus Nutrition 0.000 description 1
- 244000086363 Pterocarpus indicus Species 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 235000009137 Quercus alba Nutrition 0.000 description 1
- 235000015762 Quercus bicolor Nutrition 0.000 description 1
- 244000143671 Quercus bicolor Species 0.000 description 1
- 241000395651 Quercus kelloggii Species 0.000 description 1
- 241000050849 Quercus laurifolia Species 0.000 description 1
- 241001346207 Quercus lyrata Species 0.000 description 1
- 241000050850 Quercus nigra Species 0.000 description 1
- 235000007748 Quercus prinus Nutrition 0.000 description 1
- 244000025767 Quercus prinus Species 0.000 description 1
- 241001531312 Quercus pubescens Species 0.000 description 1
- 235000009135 Quercus rubra Nutrition 0.000 description 1
- 240000004885 Quercus rubra Species 0.000 description 1
- 241001473774 Quercus stellata Species 0.000 description 1
- 241000883644 Quercus texana Species 0.000 description 1
- 235000017848 Rubus fruticosus Nutrition 0.000 description 1
- 241000235342 Saccharomycetes Species 0.000 description 1
- 241000899950 Salix glauca Species 0.000 description 1
- 241000119565 Salix gooddingii Species 0.000 description 1
- CGMDPTNRMYIZTM-UHFFFAOYSA-N Sarohornene Natural products CC=CC=CC=CC CGMDPTNRMYIZTM-UHFFFAOYSA-N 0.000 description 1
- 240000003829 Sorghum propinquum Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 244000186561 Swietenia macrophylla Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241001116498 Taxus baccata Species 0.000 description 1
- 240000002871 Tectona grandis Species 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 235000008109 Thuja occidentalis Nutrition 0.000 description 1
- 240000003243 Thuja occidentalis Species 0.000 description 1
- 241000218638 Thuja plicata Species 0.000 description 1
- 240000007591 Tilia tomentosa Species 0.000 description 1
- 240000003021 Tsuga heterophylla Species 0.000 description 1
- 235000008554 Tsuga heterophylla Nutrition 0.000 description 1
- 241000707822 Ulmus glabra Species 0.000 description 1
- 241001473768 Ulmus rubra Species 0.000 description 1
- 244000025271 Umbellularia californica Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 235000006801 Ximenia americana Nutrition 0.000 description 1
- 244000112726 Ximenia americana Species 0.000 description 1
- 229920002000 Xyloglucan Polymers 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- UGXQOOQUZRUVSS-ZZXKWVIFSA-N [5-[3,5-dihydroxy-2-(1,3,4-trihydroxy-5-oxopentan-2-yl)oxyoxan-4-yl]oxy-3,4-dihydroxyoxolan-2-yl]methyl (e)-3-(4-hydroxyphenyl)prop-2-enoate Chemical compound OC1C(OC(CO)C(O)C(O)C=O)OCC(O)C1OC1C(O)C(O)C(COC(=O)\C=C\C=2C=CC(O)=CC=2)O1 UGXQOOQUZRUVSS-ZZXKWVIFSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N aldehydo-N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229920000617 arabinoxylan Polymers 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical class O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical group C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 235000021029 blackberry Nutrition 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 210000003464 cuspid Anatomy 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 125000004982 dihaloalkyl group Chemical group 0.000 description 1
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 1
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003844 furanonyl group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000010181 horse chestnut Nutrition 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002065 inelastic X-ray scattering Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000013178 mathematical model Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000005882 oxadiazolinyl group Chemical group 0.000 description 1
- 150000002918 oxazolines Polymers 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920006260 polyaryletherketone Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- PAQYIEZTLSDLQO-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine Chemical compound N1=CN=C2C=NC=CC2=C1 PAQYIEZTLSDLQO-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 235000003499 redwood Nutrition 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000012069 sugar maple Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 244000239645 swamp mahogany Species 0.000 description 1
- 235000005221 swamp mahogany Nutrition 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- BPJYAXCTOHRFDQ-UHFFFAOYSA-L tetracopper;2,4,6-trioxido-1,3,5,2,4,6-trioxatriarsinane;diacetate Chemical compound [Cu+2].[Cu+2].[Cu+2].[Cu+2].CC([O-])=O.CC([O-])=O.[O-][As]1O[As]([O-])O[As]([O-])O1.[O-][As]1O[As]([O-])O[As]([O-])O1 BPJYAXCTOHRFDQ-UHFFFAOYSA-L 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000005886 tetrahydrobenzothienyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
- JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
- 125000005881 triazolinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000011850 water-based material Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 240000004494 yellow birch Species 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
- B01J31/0294—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate by polar or ionic interaction with the substrate, e.g. glass
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
- B01J31/0295—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate by covalent attachment to the substrate, e.g. silica
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Catalysts (AREA)
- Processing Of Solid Wastes (AREA)
Abstract
Description
Claims (19)
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261693200P | 2012-08-24 | 2012-08-24 | |
US201261693210P | 2012-08-24 | 2012-08-24 | |
US201261693213P | 2012-08-24 | 2012-08-24 | |
US61/693,213 | 2012-08-24 | ||
US61/693,200 | 2012-08-24 | ||
US61/693,210 | 2012-08-24 | ||
US13/831,495 | 2013-03-14 | ||
US13/831,495 US9238845B2 (en) | 2012-08-24 | 2013-03-14 | Methods of producing sugars from biomass feedstocks |
PCT/US2013/056389 WO2014031956A1 (en) | 2012-08-24 | 2013-08-23 | Polymeric and solid-supported catalysts, and methods of digesting cellulosic materials using such catalysts |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104736245A true CN104736245A (zh) | 2015-06-24 |
CN104736245B CN104736245B (zh) | 2017-04-12 |
Family
ID=53181377
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201380055050.3A Active CN104736245B (zh) | 2012-08-24 | 2013-08-23 | 高分子催化剂和固载化催化剂、以及使用该催化剂消化纤维素材料的方法 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2888044A4 (zh) |
KR (1) | KR20150047583A (zh) |
CN (1) | CN104736245B (zh) |
CA (1) | CA2922254A1 (zh) |
WO (1) | WO2014031956A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106914258A (zh) * | 2017-01-11 | 2017-07-04 | 湖南师范大学 | 一种硅胶柱撑介孔生物质碳固体磺酸的制备方法 |
CN108339540A (zh) * | 2018-03-29 | 2018-07-31 | 洛阳理工学院 | 一种功能性核壳型磁性固相萃取剂的制备方法及应用 |
CN108624974A (zh) * | 2017-12-31 | 2018-10-09 | 龙丝(上海)新材料科技有限公司 | 一种珍珠纤维的制备方法 |
CN109314250A (zh) * | 2016-08-02 | 2019-02-05 | 百拉得动力系统公司 | 具有改进的电极的膜电极组件 |
CN111122429A (zh) * | 2019-12-31 | 2020-05-08 | 华南理工大学 | 纳米纤维素纤化程度的快速检测方法 |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2015287703A1 (en) * | 2014-07-09 | 2017-02-16 | Cadena Bio, Inc. | Oligosaccharide compositions and methods for producing thereof |
WO2016095207A1 (en) * | 2014-12-19 | 2016-06-23 | Rhodia Operations | Carbon/fluoropolymer composite and manufacturing methods thereof |
CN107427042A (zh) * | 2015-01-26 | 2017-12-01 | 卡德纳生物股份有限公司 | 用作食品成分的寡糖组合物和其制造方法 |
ES2755042T3 (es) | 2015-01-26 | 2020-04-21 | Cadena Bio Inc | Composiciones de oligosacáridos para el uso como alimento para animales y sus métodos para producirlas |
WO2016122885A1 (en) * | 2015-01-26 | 2016-08-04 | Midori Usa, Inc. | Oligosaccharide compositions for use in nutritional compositions, and methods of producing thereof |
AU2016212030B2 (en) | 2015-01-26 | 2021-06-17 | Kaleido Biosciences, Inc. | Glycan therapeutics and related methods thereof |
AU2016253010B2 (en) | 2015-04-23 | 2021-06-10 | Kaleido Biosciences, Inc. | Glycan therapeutics and methods of treatment |
RU2017134547A (ru) | 2015-04-23 | 2019-04-09 | Калейдо Байосайенсиз, Инк. | Регуляторы микробиома и соответствующие варианты их применения |
CN109689067A (zh) | 2016-07-13 | 2019-04-26 | 卡莱多生物科技有限公司 | 聚糖组合物和使用方法 |
EP3551194B1 (en) | 2016-12-06 | 2023-10-18 | DSM Nutritional Products, LLC | Glycan polymers and related methods thereof |
EP3651776A1 (en) | 2017-07-13 | 2020-05-20 | Kaleido Biosciences, Inc. | Glycan compositions and methods of use |
CN111417398A (zh) | 2017-11-03 | 2020-07-14 | 卡莱多生物科技有限公司 | 用于治疗感染的聚糖制剂 |
EP3703705B1 (en) | 2017-11-03 | 2024-05-15 | DSM Nutritional Products, LLC | Glucose-containing glycan preparations for use in the treatment of hyperammonaemia |
EP3704161A1 (en) | 2017-11-03 | 2020-09-09 | Kaleido Biosciences, Inc. | Methods of producing glycan polymers |
WO2020041531A2 (en) | 2018-08-21 | 2020-02-27 | Kaleido Biosciences, Inc. | Oligosaccharide compositions and methods of use thereof for reducing ammonia levels |
AU2019375992A1 (en) | 2018-11-08 | 2021-05-13 | Dsm Ip Assets, B.V. | Methods of modulating gastrointestinal metabolites |
EP3877424A2 (en) | 2018-11-08 | 2021-09-15 | Kaleido Biosciences, Inc. | Oligosaccharide compositions and methods of use thereof |
EP3876749B1 (en) | 2018-11-08 | 2024-02-14 | DSM IP Assets B.V. | Methods of selectively modulating gastrointestinal microbial growth |
MX2021005374A (es) | 2018-11-08 | 2021-09-14 | Dsm Ip Assets Bv | Metodos para dar soporte a homeostasis gastrointestinal. |
CN111500658B (zh) * | 2020-04-10 | 2023-10-03 | 大连海洋大学 | 生物质多途径增值利用的方法 |
CN111686695A (zh) * | 2020-04-22 | 2020-09-22 | 杭州嘉澍环境监测有限公司 | 一种改性甲壳素材料的制备方法和作为贵金属金吸附材料的应用 |
CN114433228A (zh) * | 2022-02-10 | 2022-05-06 | 惠州市绿色能源与新材料研究院 | 一种核壳型聚合离子液体催化合成环状碳酸酯的方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW548283B (en) * | 2000-01-11 | 2003-08-21 | Dow Chemical Co | Chemically-modified supports and supported catalyst systems prepared therefrom |
JP2003299949A (ja) * | 2002-04-10 | 2003-10-21 | Toyobo Co Ltd | 吸着剤およびその製造方法 |
EP2050755A1 (en) * | 2007-10-19 | 2009-04-22 | Total Petrochemicals Research Feluy | Supported ionic liquids or activating supports |
CA2864086C (en) * | 2011-02-28 | 2018-07-10 | Midori Renewables, Inc. | Polymeric acid catalysts and uses thereof |
-
2013
- 2013-08-23 EP EP13831228.5A patent/EP2888044A4/en not_active Withdrawn
- 2013-08-23 CN CN201380055050.3A patent/CN104736245B/zh active Active
- 2013-08-23 WO PCT/US2013/056389 patent/WO2014031956A1/en active Application Filing
- 2013-08-23 KR KR1020157007481A patent/KR20150047583A/ko unknown
- 2013-08-23 CA CA2922254A patent/CA2922254A1/en not_active Abandoned
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109314250A (zh) * | 2016-08-02 | 2019-02-05 | 百拉得动力系统公司 | 具有改进的电极的膜电极组件 |
CN109314250B (zh) * | 2016-08-02 | 2022-02-18 | 百拉得动力系统公司 | 具有改进的电极的膜电极组件 |
CN106914258A (zh) * | 2017-01-11 | 2017-07-04 | 湖南师范大学 | 一种硅胶柱撑介孔生物质碳固体磺酸的制备方法 |
CN108624974A (zh) * | 2017-12-31 | 2018-10-09 | 龙丝(上海)新材料科技有限公司 | 一种珍珠纤维的制备方法 |
CN108624974B (zh) * | 2017-12-31 | 2020-02-14 | 龙丝(上海)新材料科技有限公司 | 一种珍珠纤维的制备方法 |
CN108339540A (zh) * | 2018-03-29 | 2018-07-31 | 洛阳理工学院 | 一种功能性核壳型磁性固相萃取剂的制备方法及应用 |
CN108339540B (zh) * | 2018-03-29 | 2020-10-30 | 洛阳理工学院 | 一种功能性核壳型磁性固相萃取剂的制备方法及应用 |
CN111122429A (zh) * | 2019-12-31 | 2020-05-08 | 华南理工大学 | 纳米纤维素纤化程度的快速检测方法 |
CN111122429B (zh) * | 2019-12-31 | 2022-04-22 | 华南理工大学 | 纳米纤维素纤化程度的快速检测方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104736245B (zh) | 2017-04-12 |
EP2888044A4 (en) | 2016-05-04 |
KR20150047583A (ko) | 2015-05-04 |
EP2888044A1 (en) | 2015-07-01 |
WO2014031956A1 (en) | 2014-02-27 |
CA2922254A1 (en) | 2014-02-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104736245B (zh) | 高分子催化剂和固载化催化剂、以及使用该催化剂消化纤维素材料的方法 | |
CN103619885B (zh) | 高分子酸催化剂及其用途 | |
Ashokkumar et al. | Recent advances in lignocellulosic biomass for biofuels and value-added bioproducts-A critical review | |
CN105209510A (zh) | 聚合离子盐催化剂及其制造方法 | |
Mamman et al. | Furfural: Hemicellulose/xylosederived biochemical | |
US9238845B2 (en) | Methods of producing sugars from biomass feedstocks | |
Kumar et al. | Physical and chemical features of pretreated biomass that influence macro‐/micro‐accessibility and biological processing | |
Cannella et al. | PEI detoxification of pretreated spruce for high solids ethanol fermentation | |
US20150202607A1 (en) | Polymeric and solid-supported catalysts, and methods of digesting cellulosic materials using such catalysts | |
Chen et al. | Improved enzymatic saccharification of bulrush via an efficient combination pretreatment | |
Chen | Hot water extraction and acid hydrolysis of dried distiller's grain | |
NZ616047B2 (en) | Polymeric acid catalysts and uses thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C53 | Correction of patent of invention or patent application | ||
CB02 | Change of applicant information |
Address after: Massachusetts, USA Applicant after: Midley (USA) Co.,Ltd. Address before: Massachusetts, USA Applicant before: MIDORI RENEWABLES, Inc. |
|
COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: MIDORI RENEWABLES INC. TO: MIDORI (AMERICA) CORPORATION Free format text: CORRECT: ADDRESS; FROM: |
|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20181012 Address after: Massachusetts, USA Patentee after: Cardner Biological Co.,Ltd. Address before: Massachusetts, USA Patentee before: Midley (USA) Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20231008 Address after: new jersey Patentee after: DSM Nutritional Products Co.,Ltd. Address before: Massachusetts Patentee before: Cardner Biological Co.,Ltd. |