CA1166653A - N-denitration of n,2,6-trinitroanilines with phase transfer catalysts - Google Patents
N-denitration of n,2,6-trinitroanilines with phase transfer catalystsInfo
- Publication number
- CA1166653A CA1166653A CA000386401A CA386401A CA1166653A CA 1166653 A CA1166653 A CA 1166653A CA 000386401 A CA000386401 A CA 000386401A CA 386401 A CA386401 A CA 386401A CA 1166653 A CA1166653 A CA 1166653A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- salt
- benzyl
- phase transfer
- process according
- 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.)
- Expired
Links
- 239000003444 phase transfer catalyst Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical group [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 13
- RCNILBAHFOUGPC-UHFFFAOYSA-N n-(3,4-dimethyl-2,6-dinitrophenyl)-n-pentan-3-ylnitramide Chemical group CCC(CC)N([N+]([O-])=O)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O RCNILBAHFOUGPC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006682 monohaloalkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical group CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical class CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229950005499 carbon tetrachloride Drugs 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- PBRZUOOAYZFGNW-UHFFFAOYSA-N n-(2,6-dinitrophenyl)nitramide Chemical group [O-][N+](=O)NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O PBRZUOOAYZFGNW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 17
- 238000006396 nitration reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical group CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 229940083608 sodium hydroxide Drugs 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- -1 dinitroaniline com-pounds Chemical class 0.000 description 7
- MIHBNYMMGYGFGX-UHFFFAOYSA-N n-(3,4-dimethyl-2,6-dinitrophenyl)-n-pentan-3-ylnitrous amide Chemical group CCC(CC)N(N=O)C1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O MIHBNYMMGYGFGX-UHFFFAOYSA-N 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical group CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical class CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 description 1
- IVOMCIOXYNVSEW-UHFFFAOYSA-N 2,3,4-trinitroaniline Chemical group NC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O IVOMCIOXYNVSEW-UHFFFAOYSA-N 0.000 description 1
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
- ZOTRFGNOTDLOAU-UHFFFAOYSA-N 3,4-dimethyl-n-pentan-3-ylaniline Chemical group CCC(CC)NC1=CC=C(C)C(C)=C1 ZOTRFGNOTDLOAU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical class C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000004008 N-nitroso compounds Chemical class 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- JZIYHVVZFKELIP-UHFFFAOYSA-N n-(2-nitrophenyl)-n-nitrosonitramide Chemical class [O-][N+](=O)N(N=O)C1=CC=CC=C1[N+]([O-])=O JZIYHVVZFKELIP-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- KOOMFXGDLMRWSN-UHFFFAOYSA-N n-phenylnitrous amide Chemical class O=NNC1=CC=CC=C1 KOOMFXGDLMRWSN-UHFFFAOYSA-N 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical group N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- BINSXQFBKIIQJI-UHFFFAOYSA-N tris(4-hydroxyphenyl)sulfanium;chloride Chemical compound [Cl-].C1=CC(O)=CC=C1[S+](C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BINSXQFBKIIQJI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/42—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitrogen-to-nitrogen bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US195,264 | 1980-10-08 | ||
| US06/195,264 US4391992A (en) | 1979-08-24 | 1980-10-08 | N-Denitration of N,2,6-trinitroanilines with phase transfer catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1166653A true CA1166653A (en) | 1984-05-01 |
Family
ID=22720722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000386401A Expired CA1166653A (en) | 1980-10-08 | 1981-09-22 | N-denitration of n,2,6-trinitroanilines with phase transfer catalysts |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4391992A (enExample) |
| EP (1) | EP0049384B1 (enExample) |
| JP (1) | JPS5793935A (enExample) |
| AR (1) | AR230044A1 (enExample) |
| BE (1) | BE891200A (enExample) |
| BR (1) | BR8106310A (enExample) |
| CA (1) | CA1166653A (enExample) |
| DE (1) | DE3169401D1 (enExample) |
| IN (1) | IN155095B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL106118A (en) * | 1993-06-24 | 1997-08-14 | Agan Chemical Manufacturers | Process for preparing n-alkyl-3,4-dialkyl- 2,6-dinitro- anilines and intermediates thereof |
| IT1293450B1 (it) * | 1997-07-14 | 1999-03-01 | Finchimica Srl | Procedimento per la purificazione di dinitroaniline. |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3403180A (en) * | 1963-10-07 | 1968-09-24 | Lilly Co Eli | 4-trifluoromethyl-2, 6-dinitroanilines |
| US3332769A (en) * | 1963-10-07 | 1967-07-25 | Lilly Co Eli | Method of eliminating germinating and seedling weed grasses and broadleaf weeds |
| US3992432A (en) * | 1967-04-05 | 1976-11-16 | Continental Oil Company | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
| US3764624A (en) * | 1970-08-05 | 1973-10-09 | United States Borax Chem | N-substituted-2,6-dinitro-3-(alkoxy or alkylthio)-4-substituted-aniline compounds |
| US3920742A (en) * | 1971-08-25 | 1975-11-18 | American Cyanamid Co | N-sec-alkyl-2,6-dinitro-3,4-xylidine herbicides |
| US3991116A (en) * | 1972-06-16 | 1976-11-09 | Amchem Products, Inc. | 4-Tert-butyl-N-sec-butyl-2,6-dinitroaniline |
| US4134917A (en) * | 1977-04-25 | 1979-01-16 | American Cyanamid Company | Method for the denitrosation of organic nitrosamines |
| US4185035A (en) * | 1977-09-02 | 1980-01-22 | Eli Lilly And Company | Dinitroaniline purification with inorganic acid halides |
| US4120905A (en) * | 1977-09-21 | 1978-10-17 | Eli Lilly And Company | Removal of nitrosating agents |
| US4155936A (en) * | 1978-03-08 | 1979-05-22 | The Goodyear Tire & Rubber Company | Para-nitrodiphenylamines synthesis using Polyethers and macrocyclic esters as solubilizing agents |
| DE2814860A1 (de) * | 1978-04-06 | 1979-10-11 | Bayer Ag | Verfahren zur herstellung von aromatischen aminen |
| US4180679A (en) * | 1978-08-22 | 1979-12-25 | American Cyanamid Company | Novel substituted dinitrotoluenes and methods for preparing the same |
| JPS55113558A (en) * | 1979-02-27 | 1980-09-02 | Fujitsu Ltd | Method of molding laminated board |
| DE2919741A1 (de) * | 1979-05-16 | 1980-11-27 | Basf Ag | Verfahren zur herstellung von m-substituierten n-methylanilinen |
| EP0024503B1 (en) * | 1979-08-24 | 1983-06-15 | American Cyanamid Company | N-denitration of n,2,6-trinitroanilines with phase transfer catalysts |
-
1980
- 1980-10-08 US US06/195,264 patent/US4391992A/en not_active Expired - Lifetime
-
1981
- 1981-09-07 IN IN1000/CAL/81A patent/IN155095B/en unknown
- 1981-09-15 DE DE8181107260T patent/DE3169401D1/de not_active Expired
- 1981-09-15 EP EP81107260A patent/EP0049384B1/en not_active Expired
- 1981-09-22 CA CA000386401A patent/CA1166653A/en not_active Expired
- 1981-09-30 BR BR8106310A patent/BR8106310A/pt unknown
- 1981-10-06 AR AR287001A patent/AR230044A1/es active
- 1981-10-07 JP JP56158896A patent/JPS5793935A/ja active Pending
- 1981-11-20 BE BE0/206611A patent/BE891200A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3169401D1 (en) | 1985-04-25 |
| US4391992A (en) | 1983-07-05 |
| EP0049384B1 (en) | 1985-03-20 |
| AR230044A1 (es) | 1984-02-29 |
| BE891200A (fr) | 1982-05-21 |
| JPS5793935A (en) | 1982-06-11 |
| BR8106310A (pt) | 1982-06-22 |
| EP0049384A1 (en) | 1982-04-14 |
| IN155095B (enExample) | 1984-12-29 |
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