CA1057774A - Dinitroaniline purification with bromine and chlorine - Google Patents
Dinitroaniline purification with bromine and chlorineInfo
- Publication number
- CA1057774A CA1057774A CA309,416A CA309416A CA1057774A CA 1057774 A CA1057774 A CA 1057774A CA 309416 A CA309416 A CA 309416A CA 1057774 A CA1057774 A CA 1057774A
- Authority
- CA
- Canada
- Prior art keywords
- nitrosamine
- bromine
- trifluralin
- dinitro
- ppm
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 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 title claims abstract description 16
- 229910052794 bromium Inorganic materials 0.000 title description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title description 14
- 239000000460 chlorine Substances 0.000 title description 9
- 229910052801 chlorine Inorganic materials 0.000 title description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title description 6
- 238000000746 purification Methods 0.000 title 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 29
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 14
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 claims abstract description 8
- NEKOXWSIMFDGMA-UHFFFAOYSA-N Isopropalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(C)C)C=C1[N+]([O-])=O NEKOXWSIMFDGMA-UHFFFAOYSA-N 0.000 claims abstract description 8
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 claims abstract description 6
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 claims abstract description 5
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 claims abstract description 5
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 claims abstract description 5
- ITVQAKZNYJEWKS-UHFFFAOYSA-N Profluralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 ITVQAKZNYJEWKS-UHFFFAOYSA-N 0.000 claims abstract description 5
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 claims abstract description 5
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 claims abstract description 5
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- USJZRMMIXCKQRV-UHFFFAOYSA-N 3-chloro-n,n-diethyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O USJZRMMIXCKQRV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005587 Oryzalin Substances 0.000 claims abstract description 4
- XKUWFOYPQIVFMM-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-4-methyl-2,6-dinitroaniline Chemical compound CC1=CC([N+]([O-])=O)=C(N(CCCl)CCCl)C([N+]([O-])=O)=C1 XKUWFOYPQIVFMM-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims description 39
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000003556 assay Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 150000004005 nitrosamines Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229960000443 hydrochloric acid Drugs 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XWHTYOOMACVCML-UHFFFAOYSA-N 2,5-dinitro-n,n-dipropyl-4-(trifluoromethyl)aniline Chemical compound CCCN(CCC)C1=CC([N+]([O-])=O)=C(C(F)(F)F)C=C1[N+]([O-])=O XWHTYOOMACVCML-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000004008 N-nitroso compounds Chemical class 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- RZJLAUZAMYYGMS-UHFFFAOYSA-N n,n-dibenzylnitrous amide Chemical compound C=1C=CC=CC=1CN(N=O)CC1=CC=CC=C1 RZJLAUZAMYYGMS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- BMNDJWSIKZECMH-UHFFFAOYSA-N nitrosyl bromide Chemical compound BrN=O BMNDJWSIKZECMH-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 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
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- 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
- C07C209/32—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 nitro groups
- C07C209/36—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 nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
- C07C211/49—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 having at least two amino groups bound to the carbon skeleton
- C07C211/50—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 having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82534577A | 1977-08-17 | 1977-08-17 | |
| US05/878,835 US4127610A (en) | 1977-08-17 | 1978-02-17 | Dinitroaniline purification with bromine and chlorine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057774A true CA1057774A (en) | 1979-07-03 |
Family
ID=27124896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA309,416A Expired CA1057774A (en) | 1977-08-17 | 1978-08-15 | Dinitroaniline purification with bromine and chlorine |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5822101B2 (de) |
| AR (1) | AR221489A1 (de) |
| AU (1) | AU518675B2 (de) |
| BG (1) | BG34332A3 (de) |
| BR (1) | BR7805279A (de) |
| CA (1) | CA1057774A (de) |
| CS (1) | CS222270B2 (de) |
| DD (1) | DD138312A5 (de) |
| DE (1) | DE2835530C2 (de) |
| DK (1) | DK152116C (de) |
| ES (1) | ES472550A1 (de) |
| FR (1) | FR2400503A1 (de) |
| GB (1) | GB2003148B (de) |
| HU (1) | HU179460B (de) |
| IE (1) | IE47178B1 (de) |
| IL (1) | IL55354A (de) |
| IT (1) | IT1098023B (de) |
| MX (1) | MX5204E (de) |
| NL (1) | NL180100C (de) |
| PL (1) | PL120364B1 (de) |
| RO (1) | RO75536A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335260A (en) * | 1980-05-15 | 1982-06-15 | Montedison S.P.A. | Process for the preparation of N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline having a low content of nitrosamines |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2920448C3 (de) * | 1979-05-21 | 1982-02-11 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Entfernung von Nitrosierungsmittel (n) aus nitrierten aromatischen Verbindungen |
| EP0019281B1 (de) * | 1979-05-21 | 1982-12-29 | Hoechst Aktiengesellschaft | Verfahren zur Entfernung von Nitrosierungsmittel(n) aus nitrierten aromatischen Verbindungen |
| DE2926947C2 (de) * | 1979-07-04 | 1982-03-18 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Entfernung von Nitrosierungsmittel (n) aus nitrierten aromatischen Verbindungen |
| IT1195822B (it) * | 1986-08-12 | 1988-10-27 | I Pi Ci Spa | Procedimento per la purificazione della trifluralina |
| US5922915A (en) * | 1998-05-11 | 1999-07-13 | Srm Chemical, Ltd., Co. | Process for removing N-nitroso compounds from organo-amine compositions including dinitroaniline herbicides |
| US10434459B2 (en) * | 2015-01-07 | 2019-10-08 | Mitsubishi Hitachi Power Systems, Ltd. | Method and device for treating nitroso compound |
-
1978
- 1978-08-10 GB GB7832840A patent/GB2003148B/en not_active Expired
- 1978-08-14 PL PL1978209046A patent/PL120364B1/pl unknown
- 1978-08-14 AR AR273298A patent/AR221489A1/es active
- 1978-08-14 IL IL55354A patent/IL55354A/xx unknown
- 1978-08-14 IT IT26768/78A patent/IT1098023B/it active
- 1978-08-14 DE DE2835530A patent/DE2835530C2/de not_active Expired
- 1978-08-14 HU HU78EI804A patent/HU179460B/hu not_active IP Right Cessation
- 1978-08-14 ES ES472550A patent/ES472550A1/es not_active Expired
- 1978-08-14 MX MX787310U patent/MX5204E/es unknown
- 1978-08-14 RO RO7894976A patent/RO75536A/ro unknown
- 1978-08-15 CS CS785322A patent/CS222270B2/cs unknown
- 1978-08-15 CA CA309,416A patent/CA1057774A/en not_active Expired
- 1978-08-16 FR FR7823852A patent/FR2400503A1/fr active Granted
- 1978-08-16 BR BR7805279A patent/BR7805279A/pt unknown
- 1978-08-16 BG BG040680A patent/BG34332A3/xx unknown
- 1978-08-16 DD DD78207319A patent/DD138312A5/de unknown
- 1978-08-16 NL NLAANVRAGE7808479,A patent/NL180100C/xx not_active IP Right Cessation
- 1978-08-16 IE IE1649/78A patent/IE47178B1/en not_active IP Right Cessation
- 1978-08-16 DK DK362578A patent/DK152116C/da not_active IP Right Cessation
- 1978-08-17 JP JP53100850A patent/JPS5822101B2/ja not_active Expired
- 1978-08-17 AU AU39028/78A patent/AU518675B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335260A (en) * | 1980-05-15 | 1982-06-15 | Montedison S.P.A. | Process for the preparation of N-di-n-propyl-2,6-dinitro-4-trifluoromethylaniline having a low content of nitrosamines |
Also Published As
| Publication number | Publication date |
|---|---|
| NL180100B (nl) | 1986-08-01 |
| DD138312A5 (de) | 1979-10-24 |
| IT7826768A0 (it) | 1978-08-14 |
| JPS5441826A (en) | 1979-04-03 |
| AU518675B2 (en) | 1981-10-15 |
| DK152116B (da) | 1988-02-01 |
| AU3902878A (en) | 1980-02-21 |
| IL55354A0 (en) | 1978-10-31 |
| BG34332A3 (en) | 1983-08-15 |
| PL120364B1 (en) | 1982-02-27 |
| DK362578A (da) | 1979-02-18 |
| HU179460B (en) | 1982-10-28 |
| IL55354A (en) | 1981-05-20 |
| GB2003148A (en) | 1979-03-07 |
| DK152116C (da) | 1988-06-20 |
| GB2003148B (en) | 1982-02-10 |
| IE47178B1 (en) | 1984-01-11 |
| DE2835530A1 (de) | 1979-03-01 |
| MX5204E (es) | 1983-04-25 |
| AR221489A1 (es) | 1981-02-13 |
| BR7805279A (pt) | 1979-04-10 |
| CS222270B2 (en) | 1983-06-24 |
| PL209046A1 (pl) | 1979-05-07 |
| NL7808479A (nl) | 1979-02-20 |
| NL180100C (nl) | 1987-01-02 |
| DE2835530C2 (de) | 1982-10-21 |
| ES472550A1 (es) | 1979-10-16 |
| JPS5822101B2 (ja) | 1983-05-06 |
| IE781649L (en) | 1979-02-17 |
| FR2400503B1 (de) | 1980-10-31 |
| FR2400503A1 (fr) | 1979-03-16 |
| RO75536A (ro) | 1980-11-30 |
| IT1098023B (it) | 1985-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4185035A (en) | Dinitroaniline purification with inorganic acid halides | |
| US4226789A (en) | Removal of nitrosamines from denitroanilines by treatment with HCl | |
| US4127610A (en) | Dinitroaniline purification with bromine and chlorine | |
| Rosenberg et al. | Determination of occupational exposure to toluene diisocyanate by biological monitoring | |
| IE47178B1 (en) | Dinitroaniline purification with bromine and chlorine | |
| IE47127B1 (en) | Purification of dinitroanilines by removal of nitrosamine impurities | |
| WO1993020030A1 (en) | Hydrodehalogenation of aromatic compounds | |
| Desai et al. | Rapid and inexpensive method for reduction of nitroarenes to anilines | |
| PL118036B1 (en) | Method of reduction of nitrosating agents concentration in 1-chloro-2,6-dinitro-4-/trifluoromethyl/benzene v 1-khloro-2,6-dinitro-4/triftorometilo/benzole | |
| AU639141B2 (en) | Process for treating dinitroanilines with sulfite to reduce impurities and to reduce the ability to produce nitrosamines | |
| US6018079A (en) | Process for removing N-nitroso compounds from organo-amine compositions including dinitroaniline herbicides | |
| KR820000056B1 (ko) | 브롬과 염소로서 디니트로 아닐린을 정제하는 방법 | |
| KR820000427B1 (ko) | 디니트로아닐린 정제법 | |
| KR890003833B1 (ko) | 부산물 테트라니트로메탄의 분해방법 | |
| KR820000052B1 (ko) | 무기산 할라이드로 디니트로 아닐린을 정제하는 방법 | |
| Eiceman et al. | Presence of nitro-chlorinated dioxins on fly ash from municipal incinerators and from laboratory production through reactions between NO2 and T4CDD on fly ash | |
| CA1304754C (en) | Process for purifying dinitroaniline herbicides | |
| Lewis et al. | Photochemical confirmation of mirex in the presence of polychlorinated biphenyls | |
| Gomez et al. | Identification of thermal degradation products from diuron and iprodione | |
| Oliver | Nitrations of acylamino‐and nitrodibenzo‐p‐dioxins | |
| US4326081A (en) | Conversion of mononitro aromatic compounds to amino compounds by hydrogen sulfide | |
| Smith et al. | Nitration of polycyclic aromatic hydrocarbons using a supported catalyst | |
| US6133448A (en) | Nitration system, and method for nitration of aromatic compounds | |
| Saha et al. | Photolysis of fluchloralin in aqueous methanol | |
| CN110498461A (zh) | 降解卤代对羟基苯胺或邻羟基苯胺的方法 |