DE2212848C3 - Verfahren zur Herstellung von Dinitrophenolen durch direkte Nitrierung - Google Patents
Verfahren zur Herstellung von Dinitrophenolen durch direkte NitrierungInfo
- Publication number
- DE2212848C3 DE2212848C3 DE2212848A DE2212848A DE2212848C3 DE 2212848 C3 DE2212848 C3 DE 2212848C3 DE 2212848 A DE2212848 A DE 2212848A DE 2212848 A DE2212848 A DE 2212848A DE 2212848 C3 DE2212848 C3 DE 2212848C3
- Authority
- DE
- Germany
- Prior art keywords
- nitric acid
- dinitrophenols
- aqueous
- cresol
- carbon atoms
- 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
- 238000000034 method Methods 0.000 title claims description 22
- 238000006396 nitration reaction Methods 0.000 title claims description 10
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 37
- 229910017604 nitric acid Inorganic materials 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 29
- -1 alkyl radical Chemical class 0.000 claims description 15
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical class OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 10
- 229940031826 phenolate Drugs 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- 230000000802 nitrating effect Effects 0.000 claims 1
- 230000009935 nitrosation Effects 0.000 claims 1
- 238000007034 nitrosation reaction Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000013049 sediment Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 5
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 4
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HXNGWMWUICJCDR-UHFFFAOYSA-N 2,4-dinitro-6-phenylphenol Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1C1=CC=CC=C1 HXNGWMWUICJCDR-UHFFFAOYSA-N 0.000 description 2
- FFVGMHVIGLEENM-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4,6-dinitrophenol Chemical compound [N+](=O)([O-])C1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=CC=C(C=C1)Cl FFVGMHVIGLEENM-UHFFFAOYSA-N 0.000 description 2
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- ONFAAMBUOAGWSG-UHFFFAOYSA-M sodium;2-methylphenolate Chemical compound [Na+].CC1=CC=CC=C1[O-] ONFAAMBUOAGWSG-UHFFFAOYSA-M 0.000 description 2
- PMOMTYBTEMMKNI-UHFFFAOYSA-M sodium;2-tert-butylphenolate Chemical compound [Na+].CC(C)(C)C1=CC=CC=C1[O-] PMOMTYBTEMMKNI-UHFFFAOYSA-M 0.000 description 2
- HGCUUEHHWFPQDD-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]phenol Chemical compound OC1=CC=CC=C1CC1=CC=C(Cl)C=C1 HGCUUEHHWFPQDD-UHFFFAOYSA-N 0.000 description 1
- QJYHUJAGJUHXJN-UHFFFAOYSA-N Dinex Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C1C1CCCCC1 QJYHUJAGJUHXJN-UHFFFAOYSA-N 0.000 description 1
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-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
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002351 wastewater Substances 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
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7110503A FR2130889A5 (enExample) | 1971-03-25 | 1971-03-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2212848A1 DE2212848A1 (de) | 1972-11-30 |
| DE2212848B2 DE2212848B2 (de) | 1980-10-02 |
| DE2212848C3 true DE2212848C3 (de) | 1981-08-13 |
Family
ID=9074093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2212848A Expired DE2212848C3 (de) | 1971-03-25 | 1972-03-16 | Verfahren zur Herstellung von Dinitrophenolen durch direkte Nitrierung |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE781072A (enExample) |
| CH (1) | CH546213A (enExample) |
| DE (1) | DE2212848C3 (enExample) |
| ES (1) | ES400859A1 (enExample) |
| FR (1) | FR2130889A5 (enExample) |
| GB (1) | GB1330083A (enExample) |
| IT (1) | IT954536B (enExample) |
| NL (1) | NL177592C (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3315798A1 (de) * | 1983-04-30 | 1984-10-31 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 6-chlor-2,4-dinitrophenol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2048168A (en) * | 1935-08-03 | 1936-07-21 | Veader Leonard | Nitrated ortho-alkyl-phenolic compounds |
| US2256195A (en) * | 1939-05-16 | 1941-09-16 | Du Pont | Manufacture of dinitro-orthocresol |
| FR1452911A (fr) * | 1965-08-06 | 1966-04-15 | France Etat | Procédé de préparation de dinitrophénols substitués et produits obtenus |
-
1971
- 1971-03-25 FR FR7110503A patent/FR2130889A5/fr not_active Expired
-
1972
- 1972-03-16 DE DE2212848A patent/DE2212848C3/de not_active Expired
- 1972-03-17 ES ES400859A patent/ES400859A1/es not_active Expired
- 1972-03-20 GB GB1297072A patent/GB1330083A/en not_active Expired
- 1972-03-22 BE BE781072A patent/BE781072A/xx not_active IP Right Cessation
- 1972-03-24 CH CH445672A patent/CH546213A/fr not_active IP Right Cessation
- 1972-03-24 NL NLAANVRAGE7203967,A patent/NL177592C/xx not_active IP Right Cessation
- 1972-03-24 IT IT67931/72A patent/IT954536B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT954536B (it) | 1973-09-15 |
| FR2130889A5 (enExample) | 1972-11-10 |
| GB1330083A (en) | 1973-09-12 |
| NL7203967A (enExample) | 1972-09-27 |
| DE2212848A1 (de) | 1972-11-30 |
| ES400859A1 (es) | 1975-02-01 |
| CH546213A (fr) | 1974-02-28 |
| NL177592B (nl) | 1985-05-17 |
| NL177592C (nl) | 1985-10-16 |
| DE2212848B2 (de) | 1980-10-02 |
| BE781072A (fr) | 1972-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) |