DE1222904B - Verfahren zur Reinigung von nitrophenolhaltigen rohen aromatischen Nitroverbindungen - Google Patents
Verfahren zur Reinigung von nitrophenolhaltigen rohen aromatischen NitroverbindungenInfo
- Publication number
- DE1222904B DE1222904B DEF41132A DEF0041132A DE1222904B DE 1222904 B DE1222904 B DE 1222904B DE F41132 A DEF41132 A DE F41132A DE F0041132 A DEF0041132 A DE F0041132A DE 1222904 B DE1222904 B DE 1222904B
- Authority
- DE
- Germany
- Prior art keywords
- aromatic nitro
- nitrophenol
- acid
- nitro compounds
- purification
- 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.)
- Pending
Links
- -1 aromatic nitro compounds Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000746 purification Methods 0.000 title claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 150000002828 nitro derivatives Chemical class 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 3
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
- B01J41/05—Processes using organic exchangers in the strongly basic form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41132A DE1222904B (de) | 1963-10-29 | 1963-10-29 | Verfahren zur Reinigung von nitrophenolhaltigen rohen aromatischen Nitroverbindungen |
| CH1246064A CH443247A (de) | 1963-10-29 | 1964-09-25 | Verfahren zur Reinigung von nitrophenolhaltigen aromatischen Nitroverbindungen |
| GB41934/64A GB1031450A (en) | 1963-10-29 | 1964-10-14 | Process for the separation of nitro derivatives of aromatic hydrocarbons from nitrophenols |
| FR992414A FR1425320A (fr) | 1963-10-29 | 1964-10-23 | Procédé de purification de dérivés nitrés d'hydrocarbures aromatiques |
| BE654746D BE654746A (enrdf_load_stackoverflow) | 1963-10-29 | 1964-10-23 | |
| NL6412608A NL6412608A (enrdf_load_stackoverflow) | 1963-10-29 | 1964-10-29 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41132A DE1222904B (de) | 1963-10-29 | 1963-10-29 | Verfahren zur Reinigung von nitrophenolhaltigen rohen aromatischen Nitroverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1222904B true DE1222904B (de) | 1966-08-18 |
Family
ID=7098536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF41132A Pending DE1222904B (de) | 1963-10-29 | 1963-10-29 | Verfahren zur Reinigung von nitrophenolhaltigen rohen aromatischen Nitroverbindungen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE654746A (enrdf_load_stackoverflow) |
| CH (1) | CH443247A (enrdf_load_stackoverflow) |
| DE (1) | DE1222904B (enrdf_load_stackoverflow) |
| FR (1) | FR1425320A (enrdf_load_stackoverflow) |
| GB (1) | GB1031450A (enrdf_load_stackoverflow) |
| NL (1) | NL6412608A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012156095A1 (de) * | 2011-05-19 | 2012-11-22 | Josef Meissner Gmbh & Co. Kg | Verfahren und vorrichtung zur aufreinigung von nitrierprodukten |
| WO2013160367A1 (de) | 2012-04-25 | 2013-10-31 | Basf Se | Verfahren zur wäsche von dinitrotoluol |
| US9249083B2 (en) | 2012-04-25 | 2016-02-02 | Basf Se | Process for scrubbing dinitrotoluene |
| RU2712699C1 (ru) * | 2019-02-20 | 2020-01-30 | Федеральное Казенное Предприятие "Бийский Олеумный Завод" | Способ получения смеси динитротолуола с тринитротолуолом (варианты) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482769A (en) * | 1983-09-16 | 1984-11-13 | Air Products And Chemicals, Inc. | Reducing 2,4-dinitroortho-cresol in effluent stream from dinitrotoluene process |
| US4597875A (en) * | 1985-05-07 | 1986-07-01 | Air Products And Chemicals, Inc. | Precipitative removal of nitrocresols from dinitrotoluene waste streams |
| US4604214A (en) * | 1985-08-16 | 1986-08-05 | Air Products And Chemicals, Inc. | Removal of nitrocresols from dinitrotoluene waste streams using fentons reagent |
| EP2670729B1 (de) * | 2011-01-31 | 2015-07-22 | Basf Se | Verhinderung von ausfällungen aus nitrierten aromatischen rohprodukten |
| US8637712B2 (en) * | 2011-01-31 | 2014-01-28 | Basf Se | Prevention of precipitation from nitrated aromatic crude products |
-
1963
- 1963-10-29 DE DEF41132A patent/DE1222904B/de active Pending
-
1964
- 1964-09-25 CH CH1246064A patent/CH443247A/de unknown
- 1964-10-14 GB GB41934/64A patent/GB1031450A/en not_active Expired
- 1964-10-23 FR FR992414A patent/FR1425320A/fr not_active Expired
- 1964-10-23 BE BE654746D patent/BE654746A/xx unknown
- 1964-10-29 NL NL6412608A patent/NL6412608A/xx unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012156095A1 (de) * | 2011-05-19 | 2012-11-22 | Josef Meissner Gmbh & Co. Kg | Verfahren und vorrichtung zur aufreinigung von nitrierprodukten |
| EP2772304A3 (de) * | 2011-05-19 | 2014-11-05 | Josef Meissner GmbH & Co. KG | Vorrichtungen zur Aufreinigung von Nitrierprodukten |
| EP2705020B1 (de) | 2011-05-19 | 2015-04-08 | Josef Meissner GmbH & Co. KG | Verfahren und vorrichtung zur aufreinigung von nitrierprodukten |
| US9115048B2 (en) | 2011-05-19 | 2015-08-25 | Josef Meissner Gmbh & Co. Kg | Method and apparatus for purifying nitration products |
| EA024988B1 (ru) * | 2011-05-19 | 2016-11-30 | Йозеф Майсснер Гмбх Унд Ко. Кг | Способ и устройство для очистки продуктов нитрования |
| WO2013160367A1 (de) | 2012-04-25 | 2013-10-31 | Basf Se | Verfahren zur wäsche von dinitrotoluol |
| US9249083B2 (en) | 2012-04-25 | 2016-02-02 | Basf Se | Process for scrubbing dinitrotoluene |
| RU2712699C1 (ru) * | 2019-02-20 | 2020-01-30 | Федеральное Казенное Предприятие "Бийский Олеумный Завод" | Способ получения смеси динитротолуола с тринитротолуолом (варианты) |
Also Published As
| Publication number | Publication date |
|---|---|
| BE654746A (enrdf_load_stackoverflow) | 1965-02-15 |
| GB1031450A (en) | 1966-06-02 |
| CH443247A (de) | 1967-09-15 |
| NL6412608A (enrdf_load_stackoverflow) | 1965-05-03 |
| FR1425320A (fr) | 1966-01-24 |
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