NO308725B1 - Endotermt reaksjonsapparat - Google Patents
Endotermt reaksjonsapparat Download PDFInfo
- Publication number
- NO308725B1 NO308725B1 NO955113A NO955113A NO308725B1 NO 308725 B1 NO308725 B1 NO 308725B1 NO 955113 A NO955113 A NO 955113A NO 955113 A NO955113 A NO 955113A NO 308725 B1 NO308725 B1 NO 308725B1
- Authority
- NO
- Norway
- Prior art keywords
- trifluoromethyl
- benzopyran
- carboxylic acid
- acid
- chloro
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 title claims description 30
- -1 trifluoromethoxy, trifluoromethylthio, amino Chemical group 0.000 claims description 449
- 150000001875 compounds Chemical class 0.000 claims description 240
- 238000000034 method Methods 0.000 claims description 152
- 239000002253 acid Substances 0.000 claims description 151
- 150000003254 radicals Chemical class 0.000 claims description 97
- 239000000460 chlorine Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- 150000002148 esters Chemical class 0.000 claims description 67
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
- 150000002431 hydrogen Chemical class 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 42
- SMQUZDBALVYZAC-UHFFFAOYSA-N ortho-hydroxybenzaldehyde Natural products OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 42
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- 239000002585 base Substances 0.000 claims description 37
- 125000001544 thienyl group Chemical group 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 29
- DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical class C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 230000004054 inflammatory process Effects 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 15
- 206010061218 Inflammation Diseases 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical class C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- QGCKNIAMHUUUDI-UHFFFAOYSA-N 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(C(C)(C)C)C(Cl)=C2 QGCKNIAMHUUUDI-UHFFFAOYSA-N 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 11
- NDCFBPDNHOZORS-UHFFFAOYSA-N 1,2-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2NCC(C(=O)O)=CC2=C1 NDCFBPDNHOZORS-UHFFFAOYSA-N 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- QSLSQLYQCKEGMS-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 QSLSQLYQCKEGMS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- VEENGDJNDWZTOU-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 VEENGDJNDWZTOU-UHFFFAOYSA-N 0.000 claims description 7
- UNQDVTXJGNPKAY-UHFFFAOYSA-N 8-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=CC=C2CC UNQDVTXJGNPKAY-UHFFFAOYSA-N 0.000 claims description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- IWTSTYWGRNOWJQ-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzo[f]chromene-3-carboxylic acid Chemical compound C1=CC=CC2=C(C=C(C(C(=O)O)O3)C(F)(F)F)C3=CC=C21 IWTSTYWGRNOWJQ-UHFFFAOYSA-N 0.000 claims description 6
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical class NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 claims description 6
- KSDMMCFWQWBVBW-UHFFFAOYSA-N 2-sulfanylbenzaldehyde Chemical class SC1=CC=CC=C1C=O KSDMMCFWQWBVBW-UHFFFAOYSA-N 0.000 claims description 6
- ZFKBWSREWJOSSJ-UHFFFAOYSA-N 6,8-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 ZFKBWSREWJOSSJ-UHFFFAOYSA-N 0.000 claims description 6
- CSOISVJKLBMNCK-UHFFFAOYSA-N 6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)OC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 CSOISVJKLBMNCK-UHFFFAOYSA-N 0.000 claims description 6
- XCTHXVRBSIHBAC-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound ClC1=CC=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 XCTHXVRBSIHBAC-UHFFFAOYSA-N 0.000 claims description 6
- DEIAIXWIMOETNX-UHFFFAOYSA-N 6-formyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O=CC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 DEIAIXWIMOETNX-UHFFFAOYSA-N 0.000 claims description 6
- ABNPGORLVYQTCX-UHFFFAOYSA-N 7-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1C1=CC=CC=C1 ABNPGORLVYQTCX-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- JDAUSBADDDDUKJ-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)C1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 JDAUSBADDDDUKJ-UHFFFAOYSA-N 0.000 claims description 5
- ICNSSUXDLAOCAM-UHFFFAOYSA-N 2-(trifluoromethyl)-6-(trifluoromethylsulfanyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)SC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 ICNSSUXDLAOCAM-UHFFFAOYSA-N 0.000 claims description 5
- XSKBUYZVRRYHKJ-UHFFFAOYSA-N 6-(4-methoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(OC(C(=C2)C(O)=O)C(F)(F)F)C2=C1 XSKBUYZVRRYHKJ-UHFFFAOYSA-N 0.000 claims description 5
- YHQKTWYBVAMUJX-UHFFFAOYSA-N 6-(benzylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)NCC1=CC=CC=C1 YHQKTWYBVAMUJX-UHFFFAOYSA-N 0.000 claims description 5
- NENVFGXZTXDKIF-UHFFFAOYSA-N 6-chloro-8-(4-chlorophenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=C(Cl)C=C1 NENVFGXZTXDKIF-UHFFFAOYSA-N 0.000 claims description 5
- CBMIVBLNFVXYHN-UHFFFAOYSA-N 6-chloro-8-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C(C)C CBMIVBLNFVXYHN-UHFFFAOYSA-N 0.000 claims description 5
- YSZVXNMIWQLFDC-UHFFFAOYSA-N 6-chloro-8-thiophen-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=CS1 YSZVXNMIWQLFDC-UHFFFAOYSA-N 0.000 claims description 5
- YKJCXFQLAGEPJU-UHFFFAOYSA-N 6-iodo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound IC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 YKJCXFQLAGEPJU-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- PCPVDBRLCKJFCI-UHFFFAOYSA-N ethyl 6-amino-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound NC1=CC=C2OC(C(F)(F)F)C(C(=O)OCC)=CC2=C1 PCPVDBRLCKJFCI-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- AKYBWCBXYSTSIR-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-benzo[h]chromene-3-carboxylic acid Chemical compound C1=CC=CC2=C(OC(C(C(=O)O)=C3)C(F)(F)F)C3=CC=C21 AKYBWCBXYSTSIR-UHFFFAOYSA-N 0.000 claims description 4
- ASSYTOFEDCYDMO-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound C1=CC=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 ASSYTOFEDCYDMO-UHFFFAOYSA-N 0.000 claims description 4
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical class CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 claims description 4
- YWZLKGBSKMLBMS-UHFFFAOYSA-N 3-(trifluoromethyl)-3h-[1]benzofuro[3,2-f]chromene-2-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC1=C2C=C(C(=O)O)C(C(F)(F)F)O1 YWZLKGBSKMLBMS-UHFFFAOYSA-N 0.000 claims description 4
- KJOSDRUNXOPTEP-UHFFFAOYSA-N 5,7-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(Cl)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1Cl KJOSDRUNXOPTEP-UHFFFAOYSA-N 0.000 claims description 4
- HMBUMPBGRPVQME-UHFFFAOYSA-N 6,7-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(Cl)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 HMBUMPBGRPVQME-UHFFFAOYSA-N 0.000 claims description 4
- QOQKUIZOHDRLNJ-UHFFFAOYSA-N 6,8-dibromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC(Br)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 QOQKUIZOHDRLNJ-UHFFFAOYSA-N 0.000 claims description 4
- XUSRBZSQUXSUFO-UHFFFAOYSA-N 6-(3-chloro-4-methoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1OC1=CC=C(OC(C(=C2)C(O)=O)C(F)(F)F)C2=C1 XUSRBZSQUXSUFO-UHFFFAOYSA-N 0.000 claims description 4
- XRCIFEVLZNDSDG-UHFFFAOYSA-N 6-(4-hydroxybenzoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(O)C=C1 XRCIFEVLZNDSDG-UHFFFAOYSA-N 0.000 claims description 4
- LJAIXLITIWWLMU-UHFFFAOYSA-N 6-(benzylsulfamoyl)-8-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)NCC1=CC=CC=C1 LJAIXLITIWWLMU-UHFFFAOYSA-N 0.000 claims description 4
- WRWBASOXAVOXNF-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)N(C)C)=CC=C21 WRWBASOXAVOXNF-UHFFFAOYSA-N 0.000 claims description 4
- DBRFBZFRUCUHKM-UHFFFAOYSA-N 6-(furan-2-ylmethylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)NCC1=CC=CO1 DBRFBZFRUCUHKM-UHFFFAOYSA-N 0.000 claims description 4
- MQSZXCIMIPOLLQ-UHFFFAOYSA-N 6-(tert-butylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)NC(C)(C)C)=CC=C21 MQSZXCIMIPOLLQ-UHFFFAOYSA-N 0.000 claims description 4
- NFSQSAYXIRPZAG-UHFFFAOYSA-N 6-(trifluoromethyl)-6h-[1,3]dioxolo[4,5-g]chromene-7-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC2=C1OCO2 NFSQSAYXIRPZAG-UHFFFAOYSA-N 0.000 claims description 4
- OODLETPYKNYFPC-UHFFFAOYSA-N 6-bromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 OODLETPYKNYFPC-UHFFFAOYSA-N 0.000 claims description 4
- OPSPKIBCFWXEJT-UHFFFAOYSA-N 6-chloro-8-(2-phenylethynyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C#CC1=CC=CC=C1 OPSPKIBCFWXEJT-UHFFFAOYSA-N 0.000 claims description 4
- UURZIRMVOPZSTF-UHFFFAOYSA-N 6-chloro-8-(3-methoxyphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=CC=CC(C=2C=3OC(C(=CC=3C=C(Cl)C=2)C(O)=O)C(F)(F)F)=C1 UURZIRMVOPZSTF-UHFFFAOYSA-N 0.000 claims description 4
- QJXCLFOKEYXFMB-UHFFFAOYSA-N 6-chloro-8-(methoxymethyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2COC QJXCLFOKEYXFMB-UHFFFAOYSA-N 0.000 claims description 4
- INQHKYYPGHLJSA-UHFFFAOYSA-N 6-cyano-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound N#CC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 INQHKYYPGHLJSA-UHFFFAOYSA-N 0.000 claims description 4
- UGQHPBVUJSRYTD-UHFFFAOYSA-N 7-tert-butyl-2-(1,1,2,2,2-pentafluoroethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)C(F)(F)F)OC2=CC(C(C)(C)C)=CC=C21 UGQHPBVUJSRYTD-UHFFFAOYSA-N 0.000 claims description 4
- YXUOMNYUFVPXPV-UHFFFAOYSA-N 8-(1h-benzimidazol-2-yl)-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2NC(C=3C=C(Cl)C=C4C=C(C(OC4=3)C(F)(F)F)C(=O)O)=NC2=C1 YXUOMNYUFVPXPV-UHFFFAOYSA-N 0.000 claims description 4
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US08/078,748 US5567398A (en) | 1990-04-03 | 1993-06-16 | Endothermic reaction apparatus and method |
PCT/US1994/006686 WO1994029013A1 (en) | 1993-06-16 | 1994-06-14 | Endothermic reaction apparatus and method |
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NO955113D0 NO955113D0 (no) | 1995-12-15 |
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US6153152A (en) * | 1990-04-03 | 2000-11-28 | The Standard Oil Company | Endothermic reaction apparatus and method |
US6096106A (en) * | 1990-04-03 | 2000-08-01 | The Standard Oil Company | Endothermic reaction apparatus |
NL1000146C2 (nl) * | 1995-04-13 | 1996-10-15 | Gastec Nv | Werkwijze voor het uitvoeren van een chemische reactie. |
US6793899B2 (en) * | 1998-10-29 | 2004-09-21 | Massachusetts Institute Of Technology | Plasmatron-catalyst system |
EP0849245A1 (en) | 1996-12-20 | 1998-06-24 | Kvaerner Process Technology Limited | Process and plant for the production of methanol |
US6139810A (en) * | 1998-06-03 | 2000-10-31 | Praxair Technology, Inc. | Tube and shell reactor with oxygen selective ion transport ceramic reaction tubes |
US6296686B1 (en) | 1998-06-03 | 2001-10-02 | Praxair Technology, Inc. | Ceramic membrane for endothermic reactions |
CZ302007B6 (cs) * | 1998-07-08 | 2010-09-01 | Toyota Jidosha Kabushiki Kaisha | Zarízení pro reformování paliva a zpusob výroby vodíkem obohaceného plynného paliva provádený v tomto zarízení |
US6296814B1 (en) * | 1998-11-10 | 2001-10-02 | International Fuel Cells, L.L.C. | Hydrocarbon fuel gas reformer assembly for a fuel cell power plant |
JP2001009264A (ja) * | 1999-04-26 | 2001-01-16 | Toyo Eng Corp | 熱交換器様式反応器 |
US6641625B1 (en) | 1999-05-03 | 2003-11-04 | Nuvera Fuel Cells, Inc. | Integrated hydrocarbon reforming system and controls |
US6415972B1 (en) | 1999-06-02 | 2002-07-09 | Speedline Technologies, Inc. | Closed loop solder wave height control system |
DE19939731A1 (de) * | 1999-08-21 | 2001-02-22 | Degussa | Bodenbrenner für Kammerofen mit Reaktionsrohren, diesen Brenner enthaltender Kammerofen und seine Verwendung |
GB2359764A (en) * | 2000-03-01 | 2001-09-05 | Geoffrey Gerald Weedon | An endothermic tube reactor |
US7125540B1 (en) * | 2000-06-06 | 2006-10-24 | Battelle Memorial Institute | Microsystem process networks |
US6497856B1 (en) * | 2000-08-21 | 2002-12-24 | H2Gen Innovations, Inc. | System for hydrogen generation through steam reforming of hydrocarbons and integrated chemical reactor for hydrogen production from hydrocarbons |
US6394043B1 (en) | 2000-12-19 | 2002-05-28 | Praxair Technology, Inc. | Oxygen separation and combustion apparatus and method |
US6793698B1 (en) | 2001-03-09 | 2004-09-21 | Uop Llc | Fuel processor reactor with integrated pre-reforming zone |
GB0113788D0 (en) * | 2001-06-06 | 2001-07-25 | Kvaerner Process Tech Ltd | Furnace and process |
US20030039601A1 (en) * | 2001-08-10 | 2003-02-27 | Halvorson Thomas Gilbert | Oxygen ion transport membrane apparatus and process for use in syngas production |
DE112005000391T5 (de) * | 2004-02-17 | 2007-12-27 | Modine Manufacturing Co., Racine | Integrierte Brennstoffverarbeitungsanlage für eine dezentrale Wasserstoffproduktion |
JP4477432B2 (ja) | 2004-06-29 | 2010-06-09 | 東洋エンジニアリング株式会社 | 改質器 |
DE102004059014B4 (de) * | 2004-12-08 | 2009-02-05 | Lurgi Gmbh | Reaktionsbehälter zur Herstellung von H2 und CO enthaltendem Synthesegas |
EP1856443B1 (en) | 2005-03-10 | 2015-08-12 | Shell Internationale Research Maatschappij B.V. | A multi-tube heat transfer system for the combustion of a fuel and heating of a process fluid and the use thereof |
WO2007035802A1 (en) | 2005-09-20 | 2007-03-29 | Honeywell International Inc. | Filter and method of making |
KR101364280B1 (ko) | 2005-12-21 | 2014-02-18 | 바이렌트, 아이엔씨. | 산소화 화합물의 개질을 위한 촉매 및 방법 |
EP1806176A1 (en) * | 2006-01-10 | 2007-07-11 | Casale Chemicals S.A. | Apparatus for the production of synthesis gas |
US7740671B2 (en) * | 2006-12-18 | 2010-06-22 | Pratt & Whitney Rocketdyne, Inc. | Dump cooled gasifier |
AU2007353527B2 (en) | 2006-12-20 | 2012-12-20 | Virent, Inc. | Reactor system for producing gaseous products |
RU2472840C2 (ru) | 2007-03-08 | 2013-01-20 | Вайрент, Инк. | Синтез жидкого топлива и химических реактивов из кислородсодержащих углеводородов |
FR2914395B1 (fr) | 2007-03-30 | 2009-11-20 | Inst Francais Du Petrole | Nouveau reacteur echangeur compact utilisant un bruleur poreux |
RU2481887C2 (ru) * | 2008-01-25 | 2013-05-20 | Басф Се | Реактор для осуществления реакций под высоким давлением, способ пуска реактора и способ осуществления реакции |
DE102008023042A1 (de) * | 2008-05-09 | 2009-11-12 | Süd-Chemie AG | Verfahren zur semi-adiabatischen, semi-isothermen Durchführung einer endothermen Reaktion unter Einsatz eines katalytischen Reaktors und Ausbildung dieses Reaktors |
CA2736800A1 (en) | 2008-08-27 | 2010-03-04 | Randy D. Cortright | Synthesis of liquid fuels from biomass |
US8597385B2 (en) | 2009-04-16 | 2013-12-03 | General Electric Company | Method and apparatus for shielding cooling tubes in a radiant syngas cooler |
US20110056216A1 (en) * | 2010-01-22 | 2011-03-10 | Edwards Randall O | Pulsed Propane Refrigeration Device and Method |
EP2635714B1 (en) * | 2010-11-05 | 2017-10-18 | Midrex Technologies, Inc. | Reformer tube apparatus having variable wall thickness and associated method of manufacture |
EP3290794A1 (en) * | 2016-09-05 | 2018-03-07 | Technip France | Method for reducing nox emission |
CN109798508B (zh) * | 2017-11-17 | 2020-11-03 | 韩国能量技术研究院 | 原料预热部一体型水蒸气改质器及含其的氢制备系统 |
IT201900008280A1 (it) * | 2019-06-06 | 2020-12-06 | Amec Foster Wheeler Italiana S R L | Reattore, in particolare reattore di reforming con vapore, e suo uso in un processo di reforming con vapore |
CN111517391A (zh) * | 2020-04-30 | 2020-08-11 | 杭州碳明科技有限公司 | 一种含高cod废水的高温处理装置和工艺 |
CN112387218B (zh) * | 2020-11-04 | 2022-09-13 | 大连海事大学 | 一种自热型列管式重整制氢反应器 |
CN114146663B (zh) * | 2021-11-26 | 2022-10-21 | 中国科学技术大学 | 基于气相催化的流动管反应器 |
WO2023217591A1 (en) * | 2022-05-09 | 2023-11-16 | Refractory Intellectual Property Gmbh & Co. Kg | Insulating lining, use of an alumina-based part, reactor for hydrocarbon reforming and process for hydrocarbon reforming |
EP4420770A1 (en) * | 2023-02-23 | 2024-08-28 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Bearing arrangement for a steam reformer tube |
Family Cites Families (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2569846A (en) * | 1951-10-02 | Method of starting a unit for high | ||
US1934836A (en) * | 1926-11-26 | 1933-11-14 | Ig Farbenindustrie Ag | Process for the catalytic conversion of hydrocarbons |
US2018619A (en) * | 1930-05-22 | 1935-10-22 | Ig Farbenindustrie Ag | Apparatus for pyrogenic conversion of hydrocarbons |
DE572614C (de) * | 1930-09-25 | 1933-03-18 | Hans Elfeldt | Verfahren zur Durchfuehrung katalytischer Gasreaktionen |
US1959151A (en) * | 1930-09-30 | 1934-05-15 | Du Pont | Method of effecting chemical reactions at elevated temperatures |
US2039603A (en) * | 1932-05-07 | 1936-05-05 | Mountain Copper Company Ltd | Method for the production of hot reducing gases |
US2291762A (en) * | 1939-09-21 | 1942-08-04 | Sun Oil Co | Catalytic apparatus |
US2294430A (en) * | 1940-08-03 | 1942-09-01 | Sun Oil Co | Catalytic converter |
US2336879A (en) * | 1942-07-10 | 1943-12-14 | Universal Oil Prod Co | Reactor |
US2483132A (en) * | 1946-02-21 | 1949-09-27 | Texas Co | Conversion of hydrocarbon gas into carbon monoxide and hydrogen |
US2491518A (en) * | 1947-04-11 | 1949-12-20 | Hydrocarbon Research Inc | Generation of synthesis gas |
US2683152A (en) * | 1951-11-28 | 1954-07-06 | Kellogg M W Co | Preparation of hydrocarbon synthesis gas |
NL202236A (es) * | 1954-09-18 | 1900-01-01 | ||
US2862984A (en) * | 1954-09-22 | 1958-12-02 | Basf Ag | Process of interacting hydrocarbons with oxygen |
DE1043291B (de) * | 1957-02-28 | 1958-11-13 | Degussa | Verfahren und Vorrichtung zur Durchfuehrung von endothermen Reaktionen |
US2933291A (en) * | 1958-03-14 | 1960-04-19 | Modine Mfg Co | Heat exchanger with an expansion joint |
US3264066A (en) * | 1962-05-01 | 1966-08-02 | Pullman Inc | Production of hydrogen |
US3215502A (en) * | 1962-07-30 | 1965-11-02 | Chemical Construction Corp | Reformer furnace |
GB1039756A (en) * | 1962-10-29 | 1966-08-24 | Gas Council | Improvements in or relating to methods of treating gases |
US3132010A (en) * | 1962-11-08 | 1964-05-05 | Pullman Inc | Reforming of gaseous hydrocarbons |
US3382044A (en) * | 1965-02-03 | 1968-05-07 | Catalysts & Chemicals Inc | Removal of sulfur compounds in steamgas reforming and shift conversion processes |
US3541729A (en) * | 1968-05-09 | 1970-11-24 | Gen Electric | Compact reactor-boiler combination |
US3531263A (en) * | 1968-08-05 | 1970-09-29 | United Aircraft Corp | Integrated reformer unit |
US3950463A (en) * | 1969-10-22 | 1976-04-13 | The Electricity Council | Production of β-alumina ceramic tubes |
US4161510A (en) * | 1972-04-03 | 1979-07-17 | Chevron Research Company | Reforming furnace having ceramic-coated tubes |
US3850231A (en) * | 1973-05-24 | 1974-11-26 | Combustion Eng | Lmfbr intermediate heat exchanger |
US3909299A (en) * | 1973-10-01 | 1975-09-30 | United Technologies Corp | Fuel cell system including reform reactor |
US4312954A (en) * | 1975-06-05 | 1982-01-26 | Kennecott Corporation | Sintered silicon carbide ceramic body |
DE2550565A1 (de) * | 1975-11-11 | 1977-05-18 | Otto & Co Gmbh Dr C | Roehrenreaktor zur durchfuehrung endothermer gasreaktionen |
US4157241A (en) * | 1976-03-29 | 1979-06-05 | Avion Manufacturing Co. | Furnace heating assembly and method of making the same |
US4071330A (en) * | 1976-12-22 | 1978-01-31 | United Technologies Corporation | Steam reforming process and apparatus therefor |
CA1101194A (en) * | 1976-12-22 | 1981-05-19 | Richard F. Buswell | Multi-tube catalytic reaction apparatus |
GB1579577A (en) * | 1977-04-14 | 1980-11-19 | Robinson L F | Reforming of hydrocarbons |
US4266600A (en) * | 1977-06-28 | 1981-05-12 | Westinghouse Electric Corp. | Heat exchanger with double walled tubes |
US4144207A (en) * | 1977-12-27 | 1979-03-13 | The Carborundum Company | Composition and process for injection molding ceramic materials |
US4203950A (en) * | 1977-12-27 | 1980-05-20 | United Technologies Corporation | Steam reforming reactor designed to reduce catalyst crushing |
US4179299A (en) * | 1978-05-01 | 1979-12-18 | The Carborundum Company | Sintered alpha silicon carbide ceramic body having equiaxed microstructure |
US4346049A (en) * | 1978-05-01 | 1982-08-24 | Kennecott Corporation | Sintered alpha silicon carbide ceramic body having equiaxed microstructure |
US4207226A (en) * | 1978-08-03 | 1980-06-10 | The Carborundum Company | Ceramic composition suited to be injection molded and sintered |
US4221763A (en) * | 1978-08-29 | 1980-09-09 | Cities Service Company | Multi tube high pressure, high temperature reactor |
DE2852410C2 (de) * | 1978-12-04 | 1981-12-03 | Kernforschungsanlage Jülich GmbH, 5170 Jülich | Verfahren und Vorrichtung zur Herstellung von Siliciumcarbid-Formkörpern |
US4233256A (en) * | 1978-12-18 | 1980-11-11 | The Carborundum Company | Process for injection molding sinterable carbide ceramic materials |
JPS55154303A (en) * | 1979-05-18 | 1980-12-01 | Toyo Eng Corp | Method and apparatus for steam-reforming hydrocarbon |
US4337170A (en) * | 1980-01-23 | 1982-06-29 | Union Carbide Corporation | Catalytic steam reforming of hydrocarbons |
JPS5826002A (ja) * | 1981-07-31 | 1983-02-16 | Toshiba Corp | スチ−ムリホ−ミング法及びスチ−ムリホ−ミング用反応管 |
EP0194067B2 (en) * | 1985-03-05 | 1994-05-11 | Imperial Chemical Industries Plc | Steam reforming hydrocarbons |
US4946667A (en) * | 1985-06-10 | 1990-08-07 | Engelhard Corporation | Method of steam reforming methanol to hydrogen |
JPS62210047A (ja) * | 1986-03-10 | 1987-09-16 | Toyo Eng Corp | 反応用装置 |
US4692306A (en) * | 1986-03-24 | 1987-09-08 | Kinetics Technology International Corporation | Catalytic reaction apparatus |
JPS62260701A (ja) * | 1986-05-02 | 1987-11-13 | Hitachi Ltd | 原料改質装置 |
US4861348A (en) * | 1986-10-08 | 1989-08-29 | Hitachi, Ltd. | Fuel reforming apparatus |
US4746329A (en) * | 1986-11-26 | 1988-05-24 | Energy Research Corporation | Methanol fuel reformer |
US4861347A (en) * | 1986-12-29 | 1989-08-29 | International Fuel Cells Corporation | Compact chemical reaction vessel |
JPH0642940B2 (ja) * | 1987-03-31 | 1994-06-08 | 東洋エンジニアリング株式会社 | 気体吸熱反応用装置 |
US4909808A (en) * | 1987-10-14 | 1990-03-20 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Steam reformer with catalytic combustor |
EP0314408B1 (en) * | 1987-10-23 | 1993-11-18 | C F Braun Inc | Reformer with low fired duty per unit of feedstock |
NO304808B1 (no) * | 1989-05-25 | 1999-02-15 | Standard Oil Co Ohio | Fast multikomponent membran, fremgangsmaate for fresmtilling av en slik membran samt anvendelse av denne |
AU661877B2 (en) * | 1990-04-03 | 1995-08-10 | Standard Oil Company, The | Endothermic reaction apparatus |
ZA911838B (en) * | 1990-04-03 | 1991-12-24 | Standard Oil Co Ohio | Endothermic reaction apparatus |
US5106590A (en) * | 1990-05-11 | 1992-04-21 | Davy Mckee (London) Limited | Gas mixer and distributor with heat exchange between incoming gases |
US5264008A (en) * | 1991-10-07 | 1993-11-23 | United Technologies Corporation | Reformer seal plate |
JPH05147901A (ja) * | 1991-11-29 | 1993-06-15 | Toshiba Corp | 燃料改質器 |
CA2079746C (en) * | 1991-12-19 | 2002-07-30 | Robert C. Ruhl | Endothermic reaction apparatus |
US5283049A (en) * | 1992-06-18 | 1994-02-01 | Quantum Chemical Corporation | Minimizing coking problems in tubular process furnaces |
-
1993
- 1993-06-16 US US08/078,748 patent/US5567398A/en not_active Expired - Lifetime
-
1994
- 1994-06-08 ZA ZA944027A patent/ZA944027B/xx unknown
- 1994-06-14 KR KR1019950705741A patent/KR100323275B1/ko not_active IP Right Cessation
- 1994-06-14 CA CA002165449A patent/CA2165449C/en not_active Expired - Lifetime
- 1994-06-14 NZ NZ267919A patent/NZ267919A/en not_active IP Right Cessation
- 1994-06-14 AU AU70608/94A patent/AU699464B2/en not_active Expired
- 1994-06-14 DE DE69419921T patent/DE69419921T2/de not_active Expired - Lifetime
- 1994-06-14 RU RU96101148A patent/RU2136360C1/ru active
- 1994-06-14 DE DE69432233T patent/DE69432233T2/de not_active Expired - Lifetime
- 1994-06-14 DK DK94919486T patent/DK0703823T3/da active
- 1994-06-14 EP EP98120649A patent/EP0895806B1/en not_active Expired - Lifetime
- 1994-06-14 WO PCT/US1994/006686 patent/WO1994029013A1/en active IP Right Grant
- 1994-06-14 DK DK98120649T patent/DK0895806T3/da active
- 1994-06-14 CN CN94192942A patent/CN1091643C/zh not_active Expired - Lifetime
- 1994-06-14 CZ CZ19953319A patent/CZ292204B6/cs not_active IP Right Cessation
- 1994-06-14 JP JP50217195A patent/JP3583780B2/ja not_active Expired - Lifetime
- 1994-06-14 EP EP94919486A patent/EP0703823B1/en not_active Expired - Lifetime
- 1994-06-15 MX MX9404530A patent/MX9404530A/es not_active IP Right Cessation
- 1994-06-16 MY MYPI94001561A patent/MY138879A/en unknown
- 1994-08-14 SA SA94150129A patent/SA94150129B1/ar unknown
-
1995
- 1995-12-13 FI FI955977A patent/FI119624B/fi active
- 1995-12-15 NO NO955113A patent/NO308725B1/no not_active IP Right Cessation
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