DE2004561A1 - - Google Patents
Info
- Publication number
- DE2004561A1 DE2004561A1 DE19702004561 DE2004561A DE2004561A1 DE 2004561 A1 DE2004561 A1 DE 2004561A1 DE 19702004561 DE19702004561 DE 19702004561 DE 2004561 A DE2004561 A DE 2004561A DE 2004561 A1 DE2004561 A1 DE 2004561A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst system
- oxide
- compound
- phenyl
- noble metal
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 52
- -1 nitro- Chemical class 0.000 claims description 44
- 150000002828 nitro derivatives Chemical class 0.000 claims description 31
- 239000012948 isocyanate Substances 0.000 claims description 28
- 150000002513 isocyanates Chemical class 0.000 claims description 26
- 229910000510 noble metal Inorganic materials 0.000 claims description 24
- 150000005309 metal halides Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 11
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 10
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- KLHMRBYLBVCGDT-UHFFFAOYSA-N 1-methyl-4-(sulfinylamino)benzene Chemical compound CC1=CC=C(N=S=O)C=C1 KLHMRBYLBVCGDT-UHFFFAOYSA-N 0.000 claims description 5
- 150000005840 aryl radicals Chemical group 0.000 claims description 5
- 239000010970 precious metal Substances 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 3
- 229910001507 metal halide Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229940117953 phenylisothiocyanate Drugs 0.000 claims description 3
- ABQKHKWXTUVKGF-UHFFFAOYSA-N 1-isothiocyanato-4-methylbenzene Chemical compound CC1=CC=C(N=C=S)C=C1 ABQKHKWXTUVKGF-UHFFFAOYSA-N 0.000 claims description 2
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 2
- OEYQBKYISMRWQB-UHFFFAOYSA-N Santal Chemical compound C=1C(OC)=CC(O)=C(C2=O)C=1OC=C2C1=CC=C(O)C(O)=C1 OEYQBKYISMRWQB-UHFFFAOYSA-N 0.000 claims 2
- FIOJWGRGPONADF-UHFFFAOYSA-N (sulfinylamino)benzene Chemical compound O=S=NC1=CC=CC=C1 FIOJWGRGPONADF-UHFFFAOYSA-N 0.000 claims 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 claims 1
- 229910021634 Rhenium(III) chloride Inorganic materials 0.000 claims 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 1
- 229910000423 chromium oxide Inorganic materials 0.000 claims 1
- HBEFVZMJESQFJR-UHFFFAOYSA-N isocyanatosulfanylbenzene Chemical compound O=C=NSC1=CC=CC=C1 HBEFVZMJESQFJR-UHFFFAOYSA-N 0.000 claims 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims 1
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 claims 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims 1
- LOIHSHVELSAXQN-UHFFFAOYSA-K trirhenium nonachloride Chemical compound Cl[Re](Cl)Cl LOIHSHVELSAXQN-UHFFFAOYSA-K 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 101150003085 Pdcl gene Proteins 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- PQFOUIMVTGBFRN-UHFFFAOYSA-N 2-isocyanato-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N=C=O PQFOUIMVTGBFRN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004971 nitroalkyl group Chemical group 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- PJKVZPKOIDQHBD-UHFFFAOYSA-K tribromorhenium Chemical compound Br[Re](Br)Br PJKVZPKOIDQHBD-UHFFFAOYSA-K 0.000 description 2
- UAIHPMFLFVHDIN-UHFFFAOYSA-K trichloroosmium Chemical compound Cl[Os](Cl)Cl UAIHPMFLFVHDIN-UHFFFAOYSA-K 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- OWJVEZJJRYZWNI-UHFFFAOYSA-N 1,1-dinitrocyclohexane Chemical class [O-][N+](=O)C1([N+]([O-])=O)CCCCC1 OWJVEZJJRYZWNI-UHFFFAOYSA-N 0.000 description 1
- SXIFBSOJAOXBRP-UHFFFAOYSA-N 1,1-dinitrodecane Chemical class CCCCCCCCCC([N+]([O-])=O)[N+]([O-])=O SXIFBSOJAOXBRP-UHFFFAOYSA-N 0.000 description 1
- LKKHEZBRRGJBGH-UHFFFAOYSA-N 1,1-dinitroethane Chemical compound [O-][N+](=O)C(C)[N+]([O-])=O LKKHEZBRRGJBGH-UHFFFAOYSA-N 0.000 description 1
- HLUAPIYZVLAARK-UHFFFAOYSA-N 1,1-dinitrohexane Chemical class CCCCCC([N+]([O-])=O)[N+]([O-])=O HLUAPIYZVLAARK-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OFMLQCPPVSVIDD-UHFFFAOYSA-N 1,3,5-trimethyl-2,4-dinitrobenzene Chemical group CC1=CC(C)=C([N+]([O-])=O)C(C)=C1[N+]([O-])=O OFMLQCPPVSVIDD-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- XJOPSLUZODPZTE-UHFFFAOYSA-N 1,4-bis(nitromethyl)cyclohexane Chemical compound [N+](=O)([O-])CC1CCC(CC1)C[N+](=O)[O-] XJOPSLUZODPZTE-UHFFFAOYSA-N 0.000 description 1
- BSFHJMGROOFSRA-UHFFFAOYSA-N 1,4-dimethyl-2-nitrobenzene Chemical group CC1=CC=C(C)C([N+]([O-])=O)=C1 BSFHJMGROOFSRA-UHFFFAOYSA-N 0.000 description 1
- FYFDQJRXFWGIBS-UHFFFAOYSA-N 1,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1 FYFDQJRXFWGIBS-UHFFFAOYSA-N 0.000 description 1
- LMQLKJIYYGOAGC-UHFFFAOYSA-N 1,4-dinitrocyclohexane Chemical compound [O-][N+](=O)C1CCC([N+]([O-])=O)CC1 LMQLKJIYYGOAGC-UHFFFAOYSA-N 0.000 description 1
- WGAXJEXVOSVLFY-UHFFFAOYSA-N 1-(2,4-dinitrophenoxy)-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O WGAXJEXVOSVLFY-UHFFFAOYSA-N 0.000 description 1
- MTDLIOADHKERAQ-UHFFFAOYSA-N 1-[(2,4-dinitrophenyl)methyl]-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O MTDLIOADHKERAQ-UHFFFAOYSA-N 0.000 description 1
- NWESJZZPAJGHRZ-UHFFFAOYSA-N 1-chloro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C([N+]([O-])=O)=C1 NWESJZZPAJGHRZ-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- XGLGESCVNJSAQY-UHFFFAOYSA-N 1-ethoxy-2-nitrobenzene Chemical compound CCOC1=CC=CC=C1[N+]([O-])=O XGLGESCVNJSAQY-UHFFFAOYSA-N 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- GTKGJLVDCJPMAE-UHFFFAOYSA-N 1-hexyl-2-isocyanatobenzene Chemical compound CCCCCCC1=CC=CC=C1N=C=O GTKGJLVDCJPMAE-UHFFFAOYSA-N 0.000 description 1
- UYZREAQIFNECFH-UHFFFAOYSA-N 1-isocyanato-3-(2-methylphenyl)benzene Chemical compound CC1=CC=CC=C1C1=CC=CC(N=C=O)=C1 UYZREAQIFNECFH-UHFFFAOYSA-N 0.000 description 1
- GFFGYTMCNVMFAJ-UHFFFAOYSA-N 1-isocyanato-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(N=C=O)=C1 GFFGYTMCNVMFAJ-UHFFFAOYSA-N 0.000 description 1
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
- HOHSBFCSOARUBF-UHFFFAOYSA-N 1-isothiocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=S)C(C)=C1 HOHSBFCSOARUBF-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- BKCTVUNGRBZYRR-UHFFFAOYSA-N 1-nitro-1-[(1-nitrocyclohexyl)methyl]cyclohexane Chemical class C1CCCCC1([N+]([O-])=O)CC1([N+](=O)[O-])CCCCC1 BKCTVUNGRBZYRR-UHFFFAOYSA-N 0.000 description 1
- XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 description 1
- MXWVNAOIXKIIJK-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenyl)sulfanylbenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1SC1=CC=CC=C1[N+]([O-])=O MXWVNAOIXKIIJK-UHFFFAOYSA-N 0.000 description 1
- IHZVFZOUXUNSPQ-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenyl)sulfonylbenzene Chemical class [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1[N+]([O-])=O IHZVFZOUXUNSPQ-UHFFFAOYSA-N 0.000 description 1
- NABSHCGXYOFMDL-UHFFFAOYSA-N 1-nitro-2-[(2-nitrophenyl)methyl]benzene Chemical class [O-][N+](=O)C1=CC=CC=C1CC1=CC=CC=C1[N+]([O-])=O NABSHCGXYOFMDL-UHFFFAOYSA-N 0.000 description 1
- MWAGUKZCDDRDCS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 MWAGUKZCDDRDCS-UHFFFAOYSA-N 0.000 description 1
- BDLNCFCZHNKBGI-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)benzene Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=C([N+]([O-])=O)C=C1 BDLNCFCZHNKBGI-UHFFFAOYSA-N 0.000 description 1
- ZZTJMQPRKBNGNX-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)sulfanylbenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC1=CC=C([N+]([O-])=O)C=C1 ZZTJMQPRKBNGNX-UHFFFAOYSA-N 0.000 description 1
- BVHNGWRPAFKGFP-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)sulfonylbenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 BVHNGWRPAFKGFP-UHFFFAOYSA-N 0.000 description 1
- XJQIIGJBBLINHD-UHFFFAOYSA-N 1-nitro-4-[(4-nitrocyclohexyl)methyl]cyclohexane Chemical compound C1CC([N+](=O)[O-])CCC1CC1CCC([N+]([O-])=O)CC1 XJQIIGJBBLINHD-UHFFFAOYSA-N 0.000 description 1
- GLBZQZXDUTUCGK-UHFFFAOYSA-N 1-nitro-4-[(4-nitrophenyl)methyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 GLBZQZXDUTUCGK-UHFFFAOYSA-N 0.000 description 1
- HHWHTVACNZRNTA-UHFFFAOYSA-N 1-nitro-4-[1-(4-nitrophenoxy)ethoxy]benzene Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OC(C)OC1=CC=C([N+]([O-])=O)C=C1 HHWHTVACNZRNTA-UHFFFAOYSA-N 0.000 description 1
- JBDYKGMNMDIHFL-UHFFFAOYSA-N 1-nitroanthracene Chemical class C1=CC=C2C=C3C([N+](=O)[O-])=CC=CC3=CC2=C1 JBDYKGMNMDIHFL-UHFFFAOYSA-N 0.000 description 1
- NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical class CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 1
- FEYJIFXFOHFGCC-UHFFFAOYSA-N 1-nitrohexane Chemical class CCCCCC[N+]([O-])=O FEYJIFXFOHFGCC-UHFFFAOYSA-N 0.000 description 1
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
- GSYMYSYDHKNXFU-UHFFFAOYSA-N 1-nitrooctadecane Chemical class CCCCCCCCCCCCCCCCCC[N+]([O-])=O GSYMYSYDHKNXFU-UHFFFAOYSA-N 0.000 description 1
- KLGHUFNKRIWCDQ-UHFFFAOYSA-N 1-nitrooctane Chemical class CCCCCCCC[N+]([O-])=O KLGHUFNKRIWCDQ-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BJNROHKGPXDHBO-UHFFFAOYSA-N 2,2-dimethyl-1-nitrobutane Chemical compound CCC(C)(C)C[N+]([O-])=O BJNROHKGPXDHBO-UHFFFAOYSA-N 0.000 description 1
- DHPRWWYQIUXCQM-UHFFFAOYSA-N 2,2-dinitropropane Chemical compound [O-][N+](=O)C(C)(C)[N+]([O-])=O DHPRWWYQIUXCQM-UHFFFAOYSA-N 0.000 description 1
- HFPWDSFSCLYXAZ-UHFFFAOYSA-N 2,3-dinitrobutane Chemical class [O-][N+](=O)C(C)C(C)[N+]([O-])=O HFPWDSFSCLYXAZ-UHFFFAOYSA-N 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- YAMGDMPGBVQUBQ-UHFFFAOYSA-N 2,4-diisocyanato-1-phenylbenzene Chemical compound O=C=NC1=CC(N=C=O)=CC=C1C1=CC=CC=C1 YAMGDMPGBVQUBQ-UHFFFAOYSA-N 0.000 description 1
- DBTRHJMMJLOORC-UHFFFAOYSA-N 2,4-dinitro-1-phenylbenzene Chemical group [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 DBTRHJMMJLOORC-UHFFFAOYSA-N 0.000 description 1
- CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 description 1
- SSFSNKZUKDBPIT-UHFFFAOYSA-N 2,4-dinitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C([N+]([O-])=O)=C1 SSFSNKZUKDBPIT-UHFFFAOYSA-N 0.000 description 1
- PBOPJYORIDJAFE-UHFFFAOYSA-N 2,4-dinitrobromobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C([N+]([O-])=O)=C1 PBOPJYORIDJAFE-UHFFFAOYSA-N 0.000 description 1
- YSOKMOXAGMIZFZ-UHFFFAOYSA-N 2,4-dinitrophenetole Chemical compound CCOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YSOKMOXAGMIZFZ-UHFFFAOYSA-N 0.000 description 1
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XCSNRORTQRKCHB-UHFFFAOYSA-N 2-chloro-6-nitrotoluene Chemical compound CC1=C(Cl)C=CC=C1[N+]([O-])=O XCSNRORTQRKCHB-UHFFFAOYSA-N 0.000 description 1
- WIYDOZQPANZDMW-UHFFFAOYSA-N 2-isocyanato-1-methyl-3-nitrobenzene Chemical class CC1=CC=CC([N+]([O-])=O)=C1N=C=O WIYDOZQPANZDMW-UHFFFAOYSA-N 0.000 description 1
- IZNWACYOILBFEG-UHFFFAOYSA-N 2-methyl-1-nitronaphthalene Chemical compound C1=CC=CC2=C([N+]([O-])=O)C(C)=CC=C21 IZNWACYOILBFEG-UHFFFAOYSA-N 0.000 description 1
- ZILXPAGTRNWSID-UHFFFAOYSA-N 2-methyl-4-(3-methyl-4-nitrophenyl)-1-nitrobenzene Chemical group C1=C([N+]([O-])=O)C(C)=CC(C=2C=C(C)C(=CC=2)[N+]([O-])=O)=C1 ZILXPAGTRNWSID-UHFFFAOYSA-N 0.000 description 1
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- RUSAWEHOGCWOPG-UHFFFAOYSA-N 3-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C#N)=C1 RUSAWEHOGCWOPG-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 1
- OIORBBLUSMONPW-UHFFFAOYSA-N 4-isocyanato-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(N=C=O)C=C1[N+]([O-])=O OIORBBLUSMONPW-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000272168 Laridae Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- FUMLKAFCVQJVEZ-UHFFFAOYSA-N [bromo(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Br)C1=CC=CC=C1 FUMLKAFCVQJVEZ-UHFFFAOYSA-N 0.000 description 1
- TVSZNNAFHLPZLF-UHFFFAOYSA-N [methoxy(nitro)methyl]benzene Chemical compound COC([N+]([O-])=O)C1=CC=CC=C1 TVSZNNAFHLPZLF-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004074 biphenyls Chemical class 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
- 239000006227 byproduct Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BWOVZCWSJFYBRM-UHFFFAOYSA-N carbononitridic isocyanate Chemical group O=C=NC#N BWOVZCWSJFYBRM-UHFFFAOYSA-N 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- VMMLSJNPNVTYMN-UHFFFAOYSA-N dinitromethylbenzene Chemical compound [O-][N+](=O)C([N+]([O-])=O)C1=CC=CC=C1 VMMLSJNPNVTYMN-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- CPNMAYYYYSWTIV-UHFFFAOYSA-N ethyl 2-nitrobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1[N+]([O-])=O CPNMAYYYYSWTIV-UHFFFAOYSA-N 0.000 description 1
- PHWSCBWNPZDYRI-UHFFFAOYSA-N ethyl 4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C=C1 PHWSCBWNPZDYRI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- HOOANQZZUGPTRH-UHFFFAOYSA-N molybdenum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Mo+3].[Mo+3] HOOANQZZUGPTRH-UHFFFAOYSA-N 0.000 description 1
- HEYRRRCRGGOAJP-UHFFFAOYSA-N n'-(2-methylphenyl)-n-phenylmethanediimine Chemical compound CC1=CC=CC=C1N=C=NC1=CC=CC=C1 HEYRRRCRGGOAJP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- IPVBXZMWDWJWHR-UHFFFAOYSA-N nitrocyclobutane Chemical compound [O-][N+](=O)C1CCC1 IPVBXZMWDWJWHR-UHFFFAOYSA-N 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
- CJSZWOGCKKDSJG-UHFFFAOYSA-N nitrocyclopentane Chemical compound [O-][N+](=O)C1CCCC1 CJSZWOGCKKDSJG-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- IHUHXSNGMLUYES-UHFFFAOYSA-J osmium(iv) chloride Chemical compound Cl[Os](Cl)(Cl)Cl IHUHXSNGMLUYES-UHFFFAOYSA-J 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical class [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- BHZSLLSDZFAPFH-UHFFFAOYSA-L palladium(2+);difluoride Chemical compound F[Pd]F BHZSLLSDZFAPFH-UHFFFAOYSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- HNNUTDROYPGBMR-UHFFFAOYSA-L palladium(ii) iodide Chemical compound [Pd+2].[I-].[I-] HNNUTDROYPGBMR-UHFFFAOYSA-L 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- MMRXYMKDBFSWJR-UHFFFAOYSA-K rhodium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Rh+3] MMRXYMKDBFSWJR-UHFFFAOYSA-K 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- UXMRNSHDSCDMLG-UHFFFAOYSA-J tetrachlororhenium Chemical compound Cl[Re](Cl)(Cl)Cl UXMRNSHDSCDMLG-UHFFFAOYSA-J 0.000 description 1
- VFKKSKGQZDULMV-UHFFFAOYSA-J tetrafluoroplatinum Chemical compound F[Pt](F)(F)F VFKKSKGQZDULMV-UHFFFAOYSA-J 0.000 description 1
- BUUWLOZTIYBNKB-UHFFFAOYSA-J tetraiodoiridium Chemical compound I[Ir](I)(I)I BUUWLOZTIYBNKB-UHFFFAOYSA-J 0.000 description 1
- PIZNQHDTOZMVBH-UHFFFAOYSA-N thionylimide Chemical compound N=S=O PIZNQHDTOZMVBH-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/34—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of chromium, molybdenum or tungsten
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/36—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of vanadium, niobium or tantalum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/14—Preparation of derivatives of isocyanic acid by catalytic reaction of nitro compounds with carbon monoxide
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79620869A | 1969-02-03 | 1969-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2004561A1 true DE2004561A1 (enExample) | 1970-08-06 |
Family
ID=25167616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702004561 Pending DE2004561A1 (enExample) | 1969-02-03 | 1970-02-02 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3689520A (enExample) |
| JP (1) | JPS4933954B1 (enExample) |
| DE (1) | DE2004561A1 (enExample) |
| FR (1) | FR2033855A5 (enExample) |
| GB (1) | GB1301521A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953488A (en) * | 1971-08-02 | 1976-04-27 | Olin Corporation | Method for preparing aliphatic and cycloaliphatic isothiocyanates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3461149A (en) * | 1964-12-28 | 1969-08-12 | American Cyanamid Co | Isocyanate process |
-
1969
- 1969-02-03 US US796208A patent/US3689520A/en not_active Expired - Lifetime
-
1970
- 1970-02-02 GB GB1301521D patent/GB1301521A/en not_active Expired
- 1970-02-02 DE DE19702004561 patent/DE2004561A1/de active Pending
- 1970-02-02 FR FR7003601A patent/FR2033855A5/fr not_active Expired
- 1970-02-03 JP JP45009051A patent/JPS4933954B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2033855A5 (enExample) | 1970-12-04 |
| JPS4933954B1 (enExample) | 1974-09-11 |
| GB1301521A (enExample) | 1972-12-29 |
| US3689520A (en) | 1972-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1768181C3 (de) | Verfahren zur Herstellung von aromatischen Isocyanaten | |
| DE1944747A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE1237103B (de) | Verfahren zur Herstellung von Isocyanaten | |
| DE2555557C3 (de) | Verfahren zur Herstellung eines aromatischen Carbaminsäurealkyiesters | |
| DE2005810A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| US3597466A (en) | Preparation of aromatic isocyanates | |
| DE2011809A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE1931211A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten und Katalysatoren hierfuer | |
| DE1907595C3 (de) | Verfahren zur Herstellung von aromatischen Isocyanaten | |
| DE1910303C3 (enExample) | ||
| DE1768184C3 (de) | Verfahren zur Herstellung aromatischer Isocyanate | |
| DE1668529B1 (de) | Verfahren zur Herstellung von aromatischen Isocyanaten | |
| US3719699A (en) | Process for the production of polyisocyanates | |
| DE1957965A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE1568044C3 (de) | Verfahren zur Herstellung von Urethanen | |
| DE1768183B1 (de) | Verfahren zur Herstellung von Isocyanatverbindungen | |
| DE2005811A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE1668529C (enExample) | ||
| US3689520A (en) | Catalytic preparation of aromatic isocyanates | |
| DE2005812A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE3044156C2 (de) | Verfahren zur Herstellung von aromatischen Mono- und Diisocyanaten | |
| US3743664A (en) | Process for preparing organic isocyanates | |
| DE1768043C (enExample) | ||
| DE2018299A1 (de) | Verfahren zur Herstellung von organischen Isocyanaten | |
| DE1768182A1 (de) | Verfahren zur Herstellung aromatischer Isothiocyanate |