SE511791C2 - Ny kemisk förening lämplig för användning som explosivämne samt mellanprodukt och framställningssätt för föreningen - Google Patents
Ny kemisk förening lämplig för användning som explosivämne samt mellanprodukt och framställningssätt för föreningenInfo
- Publication number
- SE511791C2 SE511791C2 SE9800900A SE9800900A SE511791C2 SE 511791 C2 SE511791 C2 SE 511791C2 SE 9800900 A SE9800900 A SE 9800900A SE 9800900 A SE9800900 A SE 9800900A SE 511791 C2 SE511791 C2 SE 511791C2
- Authority
- SE
- Sweden
- Prior art keywords
- nitric acid
- group
- heterocyclic
- diamino
- dinitroethylene
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 239000002360 explosive Substances 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000013067 intermediate product Substances 0.000 title description 2
- 239000000047 product Substances 0.000 claims abstract description 29
- FUHQFAMVYDIUKL-UHFFFAOYSA-N fox-7 Chemical group NC(N)=C([N+]([O-])=O)[N+]([O-])=O FUHQFAMVYDIUKL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002244 precipitate Substances 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 239000012736 aqueous medium Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 38
- 229910017604 nitric acid Inorganic materials 0.000 claims description 37
- 238000006396 nitration reaction Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 17
- 238000006386 neutralization reaction Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 7
- LGIBLFRXBLZDCO-UHFFFAOYSA-N 2-methyl-1h-imidazole-4,5-dione Chemical compound CC1=NC(=O)C(=O)N1 LGIBLFRXBLZDCO-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- NESRMACYJSUTIP-UHFFFAOYSA-N 2-methoxy-2-methylimidazolidine-4,5-dione Chemical compound COC1(C)NC(=O)C(=O)N1 NESRMACYJSUTIP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- GNVCKXIBBIIFPE-UHFFFAOYSA-N 2-methyl-1h-pyrimidine-4,6-dione Chemical compound CC1=NC(=O)CC(=O)N1 GNVCKXIBBIIFPE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 7
- ODZYMSKQIROSOC-UHFFFAOYSA-N 1h-imidazole-4,5-dione Chemical compound O=C1NC=NC1=O ODZYMSKQIROSOC-UHFFFAOYSA-N 0.000 description 7
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical class CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- -1 methoxy- Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- JAEMWNGTMVISQW-UHFFFAOYSA-N 1,1-dinitroethene Chemical group [O-][N+](=O)C(=C)[N+]([O-])=O JAEMWNGTMVISQW-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- AXXMYDWITMGCTE-UHFFFAOYSA-N 2-(dinitromethylidene)-5,5-dinitroimidazolidin-4-one Chemical compound [O-][N+](=O)C([N+]([O-])=O)=C1NC(=O)C([N+]([O-])=O)([N+]([O-])=O)N1 AXXMYDWITMGCTE-UHFFFAOYSA-N 0.000 description 2
- ZLWBOELZHFCUMQ-UHFFFAOYSA-N 2-(dinitromethylidene)imidazolidine-4,5-dione Chemical compound [O-][N+](=O)C([N+]([O-])=O)=C1NC(=O)C(=O)N1 ZLWBOELZHFCUMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005474 detonation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical class CC1=NC=CC=N1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 1
- FWUZMARGARSTOG-UHFFFAOYSA-N 2-methylpyrimidine-4,5-dione Chemical compound CC1=NC(=O)C(=O)C=N1 FWUZMARGARSTOG-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- PZKFSRWSQOQYNR-UHFFFAOYSA-N 5-methyl-1h-1,2,4-triazole Chemical class CC1=NC=NN1 PZKFSRWSQOQYNR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000012866 crystallographic experiment Methods 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 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
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical group [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/24—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9800900A SE511791C2 (sv) | 1997-07-16 | 1998-03-18 | Ny kemisk förening lämplig för användning som explosivämne samt mellanprodukt och framställningssätt för föreningen |
| DE1998621625 DE69821625T2 (de) | 1997-07-16 | 1998-07-02 | Als sprengstoff geeignete chemische verbindung, zwischenprodukt und verahren zur herstellung der verbindung |
| EP98934028A EP1007503B1 (de) | 1997-07-16 | 1998-07-02 | Als sprengstoff geeignete chemische verbindung, zwischenprodukt und verahren zur herstellung der verbindung |
| DK98934028T DK1007503T3 (da) | 1997-07-16 | 1998-07-02 | Ny kemisk forbindelse egnet til anvendelse som et sprængstof, et mellemprodukt og fremgangsmåde til fremstilling af forbindelsen |
| PCT/SE1998/001304 WO1999003818A1 (en) | 1997-07-16 | 1998-07-02 | New chemical compound suitable for use as an explosive, intermediate and method for preparing the compound |
| US09/462,479 US6312538B1 (en) | 1997-07-16 | 1998-07-02 | Chemical compound suitable for use as an explosive, intermediate and method for preparing the compound |
| AU83636/98A AU8363698A (en) | 1997-07-16 | 1998-07-02 | New chemical compound suitable for use as an explosive, intermediate and method for preparing the compound |
| AT98934028T ATE259344T1 (de) | 1997-07-16 | 1998-07-02 | Als sprengstoff geeignete chemische verbindung, zwischenprodukt und verahren zur herstellung der verbindung |
| NO20000205A NO314397B1 (no) | 1997-07-16 | 2000-01-14 | Kjemisk forbindelse egnet til anvendelse som et eksplosiv, mellomprodukt ogfremgangsmåte for fremstilling av forbindelsen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9702735A SE9702735D0 (sv) | 1997-07-16 | 1997-07-16 | Ny kemisk förening lämplig för användning som explosivämne samt mellanprodukt och framställningssätt för föreningen |
| SE9800900A SE511791C2 (sv) | 1997-07-16 | 1998-03-18 | Ny kemisk förening lämplig för användning som explosivämne samt mellanprodukt och framställningssätt för föreningen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9800900D0 SE9800900D0 (sv) | 1998-03-18 |
| SE9800900L SE9800900L (sv) | 1999-01-17 |
| SE511791C2 true SE511791C2 (sv) | 1999-11-29 |
Family
ID=26663040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9800900A SE511791C2 (sv) | 1997-07-16 | 1998-03-18 | Ny kemisk förening lämplig för användning som explosivämne samt mellanprodukt och framställningssätt för föreningen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6312538B1 (de) |
| EP (1) | EP1007503B1 (de) |
| AT (1) | ATE259344T1 (de) |
| AU (1) | AU8363698A (de) |
| DE (1) | DE69821625T2 (de) |
| DK (1) | DK1007503T3 (de) |
| NO (1) | NO314397B1 (de) |
| SE (1) | SE511791C2 (de) |
| WO (1) | WO1999003818A1 (de) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6113713A (en) * | 1999-07-22 | 2000-09-05 | Trw Inc. | Reduced smoke gas generant with improved mechanical stability |
| KR100377321B1 (ko) * | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
| US7743606B2 (en) | 2004-11-18 | 2010-06-29 | Honeywell International Inc. | Exhaust catalyst system |
| US7182075B2 (en) | 2004-12-07 | 2007-02-27 | Honeywell International Inc. | EGR system |
| US7275374B2 (en) | 2004-12-29 | 2007-10-02 | Honeywell International Inc. | Coordinated multivariable control of fuel and air in engines |
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| US6113713A (en) * | 1999-07-22 | 2000-09-05 | Trw Inc. | Reduced smoke gas generant with improved mechanical stability |
-
1998
- 1998-03-18 SE SE9800900A patent/SE511791C2/sv not_active IP Right Cessation
- 1998-07-02 AT AT98934028T patent/ATE259344T1/de not_active IP Right Cessation
- 1998-07-02 DE DE1998621625 patent/DE69821625T2/de not_active Expired - Lifetime
- 1998-07-02 WO PCT/SE1998/001304 patent/WO1999003818A1/en not_active Ceased
- 1998-07-02 DK DK98934028T patent/DK1007503T3/da active
- 1998-07-02 US US09/462,479 patent/US6312538B1/en not_active Expired - Lifetime
- 1998-07-02 AU AU83636/98A patent/AU8363698A/en not_active Abandoned
- 1998-07-02 EP EP98934028A patent/EP1007503B1/de not_active Expired - Lifetime
-
2000
- 2000-01-14 NO NO20000205A patent/NO314397B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1007503A1 (de) | 2000-06-14 |
| DE69821625D1 (de) | 2004-03-18 |
| EP1007503B1 (de) | 2004-02-11 |
| WO1999003818A1 (en) | 1999-01-28 |
| AU8363698A (en) | 1999-02-10 |
| SE9800900D0 (sv) | 1998-03-18 |
| NO20000205L (no) | 2000-03-15 |
| NO314397B1 (no) | 2003-03-17 |
| DE69821625T2 (de) | 2005-01-13 |
| SE9800900L (sv) | 1999-01-17 |
| DK1007503T3 (da) | 2004-06-21 |
| NO20000205D0 (no) | 2000-01-14 |
| US6312538B1 (en) | 2001-11-06 |
| ATE259344T1 (de) | 2004-02-15 |
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| NUG | Patent has lapsed |