DE2001570B2 - Verfahren zur Herstellung aromatischer Dinitrohalogenverbindungen - Google Patents
Verfahren zur Herstellung aromatischer DinitrohalogenverbindungenInfo
- Publication number
- DE2001570B2 DE2001570B2 DE2001570A DE2001570A DE2001570B2 DE 2001570 B2 DE2001570 B2 DE 2001570B2 DE 2001570 A DE2001570 A DE 2001570A DE 2001570 A DE2001570 A DE 2001570A DE 2001570 B2 DE2001570 B2 DE 2001570B2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- compounds
- aromatic
- radicals
- acid
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 title claims description 10
- 125000003118 aryl group Chemical group 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KESYALTWUAFAAC-UHFFFAOYSA-N 2,6-dinitro-4-chlorophenol Chemical compound OC1=C([N+]([O-])=O)C=C(Cl)C=C1[N+]([O-])=O KESYALTWUAFAAC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- -1 hydrogen halogen Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- AGGUKALRPKAKSM-UHFFFAOYSA-N 2,5-dichloro-1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1Cl AGGUKALRPKAKSM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 description 1
- JCRIDWXIBSEOEG-UHFFFAOYSA-N 2,6-dinitrophenol Chemical class OC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O JCRIDWXIBSEOEG-UHFFFAOYSA-N 0.000 description 1
- FXMUNKFQIKDUBF-UHFFFAOYSA-N 2-chloro-1-methyl-3,5-dinitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1Cl FXMUNKFQIKDUBF-UHFFFAOYSA-N 0.000 description 1
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CGHCHDJWHQFUGW-UHFFFAOYSA-N C(=O)(Cl)Cl.CN(C(N(C)C)=O)C Chemical compound C(=O)(Cl)Cl.CN(C(N(C)C)=O)C CGHCHDJWHQFUGW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2001570A DE2001570B2 (de) | 1970-01-15 | 1970-01-15 | Verfahren zur Herstellung aromatischer Dinitrohalogenverbindungen |
| CH1922670A CH553744A (de) | 1970-01-15 | 1970-12-28 | Verfahren zur herstellung aromatischer dinitrohalogenverbindungen. |
| US00104144A US3719717A (en) | 1970-01-15 | 1971-01-05 | Process for the production of aromatic dinitrohalogen compounds |
| GB116771A GB1330104A (en) | 1970-01-15 | 1971-01-11 | Process for the production of aromatic dinitrohalogen compounds |
| AT21971A AT312579B (de) | 1970-01-15 | 1971-01-13 | Verfahren zur Herstellung aromatischer Polynitrohalogenverbindungen, insbesondere Dinitrohalogenverbindungen |
| NL7100462A NL7100462A (enExample) | 1970-01-15 | 1971-01-13 | |
| SE7100408A SE379754B (enExample) | 1970-01-15 | 1971-01-14 | |
| FR7101370A FR2075613A5 (enExample) | 1970-01-15 | 1971-01-15 | |
| BE761627A BE761627A (fr) | 1970-01-15 | 1971-01-15 | Procede de preparation de composes dinitrohalogenes aromatiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2001570A DE2001570B2 (de) | 1970-01-15 | 1970-01-15 | Verfahren zur Herstellung aromatischer Dinitrohalogenverbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2001570A1 DE2001570A1 (de) | 1971-07-22 |
| DE2001570B2 true DE2001570B2 (de) | 1978-07-20 |
Family
ID=5759645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2001570A Withdrawn DE2001570B2 (de) | 1970-01-15 | 1970-01-15 | Verfahren zur Herstellung aromatischer Dinitrohalogenverbindungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3719717A (enExample) |
| AT (1) | AT312579B (enExample) |
| BE (1) | BE761627A (enExample) |
| CH (1) | CH553744A (enExample) |
| DE (1) | DE2001570B2 (enExample) |
| FR (1) | FR2075613A5 (enExample) |
| GB (1) | GB1330104A (enExample) |
| NL (1) | NL7100462A (enExample) |
| SE (1) | SE379754B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007488A1 (fr) * | 1988-12-30 | 1990-07-12 | Andrievsky Alexandr M | Procede d'obtention de 2-brome-4,6-dinitrochlorobenzene |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4596893A (en) * | 1984-01-31 | 1986-06-24 | Budapesti Vegyimuvek | 2-trifluoromethyl-4,6-dinitro-phenol and derivatives thereof, process for the preparation thereof and herbicidal, acaricidal and crop regulation compositions containing same |
| DE3731527A1 (de) * | 1987-09-18 | 1989-03-30 | Bayer Ag | Neue 2-methyl-4-fluor-phenole und deren herstellung |
-
1970
- 1970-01-15 DE DE2001570A patent/DE2001570B2/de not_active Withdrawn
- 1970-12-28 CH CH1922670A patent/CH553744A/xx not_active IP Right Cessation
-
1971
- 1971-01-05 US US00104144A patent/US3719717A/en not_active Expired - Lifetime
- 1971-01-11 GB GB116771A patent/GB1330104A/en not_active Expired
- 1971-01-13 AT AT21971A patent/AT312579B/de active
- 1971-01-13 NL NL7100462A patent/NL7100462A/xx unknown
- 1971-01-14 SE SE7100408A patent/SE379754B/xx unknown
- 1971-01-15 BE BE761627A patent/BE761627A/xx unknown
- 1971-01-15 FR FR7101370A patent/FR2075613A5/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007488A1 (fr) * | 1988-12-30 | 1990-07-12 | Andrievsky Alexandr M | Procede d'obtention de 2-brome-4,6-dinitrochlorobenzene |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2075613A5 (enExample) | 1971-10-08 |
| GB1330104A (en) | 1973-09-12 |
| SE379754B (enExample) | 1975-10-20 |
| US3719717A (en) | 1973-03-06 |
| AT312579B (de) | 1974-01-10 |
| BE761627A (fr) | 1971-07-15 |
| NL7100462A (enExample) | 1971-07-19 |
| DE2001570A1 (de) | 1971-07-22 |
| CH553744A (de) | 1974-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHN | Withdrawal |