DE1543329B2 - Verfahren zur Herstellung von vorwiegend p-nitriertem Phenol oder m-Kresol - Google Patents
Verfahren zur Herstellung von vorwiegend p-nitriertem Phenol oder m-KresolInfo
- Publication number
- DE1543329B2 DE1543329B2 DE1543329A DE1543329A DE1543329B2 DE 1543329 B2 DE1543329 B2 DE 1543329B2 DE 1543329 A DE1543329 A DE 1543329A DE 1543329 A DE1543329 A DE 1543329A DE 1543329 B2 DE1543329 B2 DE 1543329B2
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- acid
- nitrophenol
- nitric acid
- phenolic compound
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 43
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 20
- 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 26
- 229910017604 nitric acid Inorganic materials 0.000 claims description 26
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 21
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000002989 phenols Chemical class 0.000 claims description 18
- 238000006396 nitration reaction Methods 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 238000005121 nitriding Methods 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 3
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 5
- 238000007254 oxidation reaction Methods 0.000 claims 5
- 230000009935 nitrosation Effects 0.000 claims 2
- 238000007034 nitrosation reaction Methods 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229930003836 cresol Natural products 0.000 claims 1
- 230000002349 favourable effect Effects 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 8
- -1 Nitrosophenol dinitrophenol o-nitrophenol p-nitrophenol Chemical compound 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QIORDSKCCHRSSD-UHFFFAOYSA-N 3-methyl-2-nitrophenol Chemical compound CC1=CC=CC(O)=C1[N+]([O-])=O QIORDSKCCHRSSD-UHFFFAOYSA-N 0.000 description 1
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance 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 |
|---|---|---|---|
| US50962965A | 1965-11-24 | 1965-11-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1543329A1 DE1543329A1 (de) | 1969-11-27 |
| DE1543329B2 true DE1543329B2 (de) | 1975-07-10 |
Family
ID=24027448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1543329A Pending DE1543329B2 (de) | 1965-11-24 | 1966-11-24 | Verfahren zur Herstellung von vorwiegend p-nitriertem Phenol oder m-Kresol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3519693A (en:Method) |
| BE (1) | BE690080A (en:Method) |
| CH (1) | CH479531A (en:Method) |
| DE (1) | DE1543329B2 (en:Method) |
| FR (1) | FR1499025A (en:Method) |
| GB (1) | GB1098717A (en:Method) |
| NL (1) | NL6615625A (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3668261A (en) * | 1965-11-24 | 1972-06-06 | American Cyanamid Co | Nitration process for phenolic compounds |
| FR1602746A (en:Method) * | 1968-12-31 | 1971-01-18 | ||
| US3917719A (en) * | 1970-06-03 | 1975-11-04 | Kerr Mc Gee Chem Corp | Process for the preparation of 4-nitro-m-cresol |
| US3761527A (en) * | 1970-06-03 | 1973-09-25 | Kerr Mc Gee Corp | Process for oxidation of 4-nitroso-m-cresol |
| CA964674A (en) * | 1971-06-30 | 1975-03-18 | Hercules Incorporated | Manufacture of nitrophenols |
| US4232175A (en) * | 1977-12-08 | 1980-11-04 | The Dow Chemical Company | Nitrosation of aromatic compounds |
| FR2638741B1 (fr) * | 1988-11-07 | 1990-12-28 | Rhone Poulenc Chimie | Procede de preparation de nitrophenols |
| FR2705672B1 (fr) * | 1993-05-26 | 1995-07-21 | Rhone Poulenc Chimie | Procédé de préparation de nitrophénols. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US46888A (en) * | 1865-03-21 | Improvement in producing coloring-matter for dyers | ||
| US2868844A (en) * | 1957-01-22 | 1959-01-13 | Ethyl Corp | Selective nitration process |
-
1965
- 1965-11-24 US US509629A patent/US3519693A/en not_active Expired - Lifetime
-
1966
- 1966-10-31 GB GB48780/66A patent/GB1098717A/en not_active Expired
- 1966-11-04 NL NL6615625A patent/NL6615625A/xx unknown
- 1966-11-14 FR FR83526A patent/FR1499025A/fr not_active Expired
- 1966-11-23 BE BE690080D patent/BE690080A/xx unknown
- 1966-11-24 CH CH1684866A patent/CH479531A/de not_active IP Right Cessation
- 1966-11-24 DE DE1543329A patent/DE1543329B2/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR1499025A (fr) | 1967-10-20 |
| BE690080A (en:Method) | 1967-05-23 |
| US3519693A (en) | 1970-07-07 |
| CH479531A (de) | 1969-10-15 |
| GB1098717A (en) | 1968-01-10 |
| NL6615625A (en:Method) | 1967-05-25 |
| DE1543329A1 (de) | 1969-11-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 |