JP2011505360A - ジアミノジニトロピリジンおよびジアミノジニトロベンゼンの合成 - Google Patents
ジアミノジニトロピリジンおよびジアミノジニトロベンゼンの合成 Download PDFInfo
- Publication number
- JP2011505360A JP2011505360A JP2010536085A JP2010536085A JP2011505360A JP 2011505360 A JP2011505360 A JP 2011505360A JP 2010536085 A JP2010536085 A JP 2010536085A JP 2010536085 A JP2010536085 A JP 2010536085A JP 2011505360 A JP2011505360 A JP 2011505360A
- Authority
- JP
- Japan
- Prior art keywords
- sulfonic acid
- diamino
- diaminodinitropyridine
- dihydroxyterephthalate
- dadnp
- 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.)
- Withdrawn
Links
- TXVNGKMUDSTDOD-UHFFFAOYSA-N 5,6-dinitropyridine-3,4-diamine Chemical compound NC1=CN=C([N+]([O-])=O)C([N+]([O-])=O)=C1N TXVNGKMUDSTDOD-UHFFFAOYSA-N 0.000 title claims abstract description 131
- YAXKSOWCKFOWDQ-UHFFFAOYSA-N 3,4-dinitrobenzene-1,2-diamine Chemical compound NC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1N YAXKSOWCKFOWDQ-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 title description 8
- 238000003786 synthesis reaction Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 78
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003927 aminopyridines Chemical class 0.000 claims abstract description 7
- 229920000642 polymer Polymers 0.000 claims description 62
- XVDKITJPWVCWDA-UHFFFAOYSA-N 2,6-diamino-5-nitropyridine-3-sulfonic acid Chemical compound NC1=NC(N)=C(S(O)(=O)=O)C=C1[N+]([O-])=O XVDKITJPWVCWDA-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- KJIPNHZXGLADPG-UHFFFAOYSA-L dipotassium;3,6-dicarboxybenzene-1,2-diolate Chemical compound [K+].[K+].OC(=O)C1=CC=C(C(O)=O)C([O-])=C1[O-] KJIPNHZXGLADPG-UHFFFAOYSA-L 0.000 claims description 9
- HOWDQPJMFFMJSR-UHFFFAOYSA-N pyridine-2,3,4,5-tetramine Chemical compound NC1=CN=C(N)C(N)=C1N HOWDQPJMFFMJSR-UHFFFAOYSA-N 0.000 claims description 9
- ICTCBBIYOXTFLI-UHFFFAOYSA-N 2,4-diamino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1[N+]([O-])=O ICTCBBIYOXTFLI-UHFFFAOYSA-N 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- KAMGOKSXKBHPHL-UHFFFAOYSA-N benzene-1,2,3,4-tetramine Chemical compound NC1=CC=C(N)C(N)=C1N KAMGOKSXKBHPHL-UHFFFAOYSA-N 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- RRDBXTBGGXLZHD-UHFFFAOYSA-N benzene-1,4-dicarboperoxoic acid Chemical compound OOC(=O)C1=CC=C(C(=O)OO)C=C1 RRDBXTBGGXLZHD-UHFFFAOYSA-N 0.000 claims description 4
- -1 dipotassium tetraaminopyridinium dihydroxyterephthalate Chemical compound 0.000 claims description 4
- FXNSAHVFCAEFGU-UHFFFAOYSA-L [K+].[K+].NC1=CC=C(N)C(N)=C1N.OC(=O)C1=CC=C(C(O)=O)C([O-])=C1[O-] Chemical compound [K+].[K+].NC1=CC=C(N)C(N)=C1N.OC(=O)C1=CC=C(C(O)=O)C([O-])=C1[O-] FXNSAHVFCAEFGU-UHFFFAOYSA-L 0.000 claims description 3
- UVSUQUOUHQHYGW-UHFFFAOYSA-N 3-amino-2-nitrobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1[N+]([O-])=O UVSUQUOUHQHYGW-UHFFFAOYSA-N 0.000 claims description 2
- FHVMNJDMDQKUFK-UHFFFAOYSA-N 4-amino-3-nitropyridine-2-sulfonic acid Chemical compound NC1=CC=NC(S(O)(=O)=O)=C1[N+]([O-])=O FHVMNJDMDQKUFK-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 claims 3
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 claims 1
- ZBQONSWZWURUDA-UHFFFAOYSA-N 3,4-diaminopyridine-2-sulfonic acid Chemical compound NC1=CC=NC(S(O)(=O)=O)=C1N ZBQONSWZWURUDA-UHFFFAOYSA-N 0.000 claims 1
- QNZDCKBBTJYQDT-UHFFFAOYSA-N 3,5-dinitropyridin-2-amine Chemical compound NC1=NC=C([N+]([O-])=O)C=C1[N+]([O-])=O QNZDCKBBTJYQDT-UHFFFAOYSA-N 0.000 claims 1
- ZKBGGGWJGOHLDS-UHFFFAOYSA-N 4,5-diamino-3-nitropyridine-2-sulfonic acid Chemical compound NC1=CN=C(S(O)(=O)=O)C([N+]([O-])=O)=C1N ZKBGGGWJGOHLDS-UHFFFAOYSA-N 0.000 claims 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 claims 1
- 238000013019 agitation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 16
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 229920003252 rigid-rod polymer Polymers 0.000 abstract description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 46
- 239000000047 product Substances 0.000 description 38
- 238000006396 nitration reaction Methods 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 29
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 24
- 239000008367 deionised water Substances 0.000 description 22
- 229910021641 deionized water Inorganic materials 0.000 description 22
- AAALVYBICLMAMA-UHFFFAOYSA-N 4,5-dianilinophthalimide Chemical compound C=1C=CC=CC=1NC=1C=C2C(=O)NC(=O)C2=CC=1NC1=CC=CC=C1 AAALVYBICLMAMA-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 20
- ZLJZDCVHRYAHAW-UHFFFAOYSA-N 3,5-dinitropyridine-2,6-diamine Chemical compound NC1=NC(N)=C([N+]([O-])=O)C=C1[N+]([O-])=O ZLJZDCVHRYAHAW-UHFFFAOYSA-N 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 18
- 239000002002 slurry Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 239000012535 impurity Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- ULVWQWVFLUTPHF-UHFFFAOYSA-N pyridine-2,6-diamine;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC=CC(N)=N1.NC1=CC=CC(N)=N1 ULVWQWVFLUTPHF-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000004448 titration Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- KKFHUIKNEKOUIT-UHFFFAOYSA-L dipotassium;2,5-dicarboxybenzene-1,4-diolate Chemical compound [K+].[K+].OC1=CC(C([O-])=O)=C(O)C=C1C([O-])=O KKFHUIKNEKOUIT-UHFFFAOYSA-L 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- IAYUQKZZQKUOFL-UHFFFAOYSA-N pyridine-2,3,5,6-tetramine Chemical compound NC1=CC(N)=C(N)N=C1N IAYUQKZZQKUOFL-UHFFFAOYSA-N 0.000 description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000012456 homogeneous solution Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- CNQMGYRFDSCXTL-UHFFFAOYSA-N 2,6-diaminopyridine-3-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=N1 CNQMGYRFDSCXTL-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- RUPDGJAVWKTTJW-UHFFFAOYSA-N 2,3-dinitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1[N+]([O-])=O RUPDGJAVWKTTJW-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- GZBKVUGZEAJYHH-UHFFFAOYSA-N 2-nitropyridin-3-amine Chemical compound NC1=CC=CN=C1[N+]([O-])=O GZBKVUGZEAJYHH-UHFFFAOYSA-N 0.000 description 1
- RFSIFTKIXZLPHR-UHFFFAOYSA-N 3,5-dinitropyridine Chemical compound [O-][N+](=O)C1=CN=CC([N+]([O-])=O)=C1 RFSIFTKIXZLPHR-UHFFFAOYSA-N 0.000 description 1
- DFBUFGZWPXQRJV-UHFFFAOYSA-N 4,6-dinitrobenzene-1,3-diamine Chemical compound NC1=CC(N)=C([N+]([O-])=O)C=C1[N+]([O-])=O DFBUFGZWPXQRJV-UHFFFAOYSA-N 0.000 description 1
- HQVSYFIMWNCOEY-UHFFFAOYSA-N 6-amino-3,5-dinitro-1h-pyridin-2-one Chemical compound NC1=NC(O)=C([N+]([O-])=O)C=C1[N+]([O-])=O HQVSYFIMWNCOEY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- ANUAIBBBDSEVKN-UHFFFAOYSA-N benzene-1,2,4,5-tetramine Chemical compound NC1=CC(N)=C(N)C=C1N ANUAIBBBDSEVKN-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- SNIXMJYDLAFFIA-UHFFFAOYSA-J tetrapotassium 2,5-dicarboxybenzene-1,4-diolate Chemical compound C1=C(C(=CC(=C1[O-])C(=O)O)[O-])C(=O)O.C1=C(C(=CC(=C1[O-])C(=O)O)[O-])C(=O)O.[K+].[K+].[K+].[K+] SNIXMJYDLAFFIA-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/76—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by nitration
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/18—Polybenzimidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/986,877 US8115007B2 (en) | 2007-11-27 | 2007-11-27 | Synthesis of diaminodinitropyridine |
| PCT/US2008/084459 WO2009070515A2 (en) | 2007-11-27 | 2008-11-24 | Synthesis of diaminodinitropyridine and diaminodinitrobenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011505360A true JP2011505360A (ja) | 2011-02-24 |
| JP2011505360A5 JP2011505360A5 (https=) | 2012-01-19 |
Family
ID=40336707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010536085A Withdrawn JP2011505360A (ja) | 2007-11-27 | 2008-11-24 | ジアミノジニトロピリジンおよびジアミノジニトロベンゼンの合成 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8115007B2 (https=) |
| EP (1) | EP2217570B1 (https=) |
| JP (1) | JP2011505360A (https=) |
| KR (1) | KR20100092963A (https=) |
| WO (1) | WO2009070515A2 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102964596B (zh) * | 2012-11-14 | 2014-11-12 | 常州大学 | 聚2,6-二氨基吡啶及其合成方法 |
| CN113574701A (zh) | 2018-10-29 | 2021-10-29 | 株式会社Lg新能源 | 负极活性材料和包含其的锂二次电池 |
| HUE072593T2 (hu) | 2018-11-19 | 2025-11-28 | Lg Energy Solution Ltd | Anód aktív anyag és az azt tartalmazó lítium szekunder akkumulátor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3740410A (en) | 1970-11-23 | 1973-06-19 | Horizons Inc | Acid addition salts of 2,3,5,6-tetraaminopyridine and a process for their preparation |
| US3838154A (en) | 1970-11-23 | 1974-09-24 | Horizons Inc | 2,6-diamino-3,5-dinitropyridines and derivatives thereof |
| US4022793A (en) | 1974-01-31 | 1977-05-10 | Horizons Research Incorporated | Triamino pyridine compounds |
| SU1066992A1 (ru) | 1982-10-05 | 1984-01-15 | Казанский Ордена Трудового Красного Знамени Химико-Технологический Институт Им.С.М.Кирова | Способ получени 2-нитрамино-3,5-динитропиридина |
| DE3727297A1 (de) | 1987-08-17 | 1989-03-02 | Wella Ag | Herstellungsverfahren fuer 2,5-diamino-6-nitro-pyridinderivate, ihre verwendung in haarfaerbemitteln sowie neue 2,5-diamino-6-nitro-pyridinderivate |
| DE3920336C2 (de) | 1989-06-21 | 1997-01-09 | Deutsch Franz Forsch Inst | Sprengstoffmasse mit geringer Empfindlichkeit |
| DE69412250T2 (de) | 1993-04-28 | 1999-02-11 | Akzo Nobel N.V., Arnheim/Arnhem | Pyridobismidazole enthaltendes rigid-rod-Polymer |
| US5945537A (en) | 1995-09-19 | 1999-08-31 | Akzo Nobel N.V. | Nitration of pyridine-2, 6-diamines |
| WO2006105227A1 (en) | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | Thermal processes for increasing polyareneazole inherent viscosities |
| WO2006105080A1 (en) | 2005-03-28 | 2006-10-05 | E.I. Du Pont De Nemours And Company | Processes for increasing polymer inherent viscosity |
-
2007
- 2007-11-27 US US11/986,877 patent/US8115007B2/en not_active Expired - Fee Related
-
2008
- 2008-11-24 WO PCT/US2008/084459 patent/WO2009070515A2/en not_active Ceased
- 2008-11-24 JP JP2010536085A patent/JP2011505360A/ja not_active Withdrawn
- 2008-11-24 EP EP08853164A patent/EP2217570B1/en not_active Not-in-force
- 2008-11-24 KR KR1020107014061A patent/KR20100092963A/ko not_active Withdrawn
-
2012
- 2012-01-09 US US13/345,996 patent/US20120116046A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100092963A (ko) | 2010-08-23 |
| WO2009070515A3 (en) | 2009-07-16 |
| US8115007B2 (en) | 2012-02-14 |
| WO2009070515A2 (en) | 2009-06-04 |
| US20090137814A1 (en) | 2009-05-28 |
| US20120116046A1 (en) | 2012-05-10 |
| EP2217570B1 (en) | 2012-12-26 |
| EP2217570A2 (en) | 2010-08-18 |
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