DE2231157C2 - 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
- DE2231157C2 DE2231157C2 DE19722231157 DE2231157A DE2231157C2 DE 2231157 C2 DE2231157 C2 DE 2231157C2 DE 19722231157 DE19722231157 DE 19722231157 DE 2231157 A DE2231157 A DE 2231157A DE 2231157 C2 DE2231157 C2 DE 2231157C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- phenol
- hno
- product
- cresol
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 16
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims description 25
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 20
- 229910017604 nitric acid Inorganic materials 0.000 claims description 20
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 10
- 239000011260 aqueous acid Substances 0.000 claims description 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000000711 cancerogenic effect Effects 0.000 claims 1
- 231100000357 carcinogen Toxicity 0.000 claims 1
- 239000003183 carcinogenic agent Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000000047 product Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 11
- 238000006396 nitration reaction Methods 0.000 description 11
- 229940100630 metacresol Drugs 0.000 description 10
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004880 explosion Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- JCRIDWXIBSEOEG-UHFFFAOYSA-N 2,6-dinitrophenol Chemical compound OC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O JCRIDWXIBSEOEG-UHFFFAOYSA-N 0.000 description 1
- QIORDSKCCHRSSD-UHFFFAOYSA-N 3-methyl-2-nitrophenol Chemical compound CC1=CC=CC(O)=C1[N+]([O-])=O QIORDSKCCHRSSD-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 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
-
- 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
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 |
|---|---|---|---|
| US15859371A | 1971-06-30 | 1971-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2231157A1 DE2231157A1 (de) | 1973-01-11 |
| DE2231157C2 true DE2231157C2 (de) | 1982-12-23 |
Family
ID=22568849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722231157 Expired DE2231157C2 (de) | 1971-06-30 | 1972-06-26 | Verfahren zur Herstellung von vorwiegend P-nitriertem Phenol oder M-Kresol |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5637215B1 (enExample) |
| CA (1) | CA964674A (enExample) |
| DE (1) | DE2231157C2 (enExample) |
| FR (1) | FR2144395A5 (enExample) |
| GB (1) | GB1345469A (enExample) |
| IT (1) | IT965860B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2357508A1 (fr) * | 1976-07-09 | 1978-02-03 | Hercules Inc | Procede pour la preparation de para-nitro-metacresol a partir d'un melange de meta-cresol et de para-cresol |
| FR2638741B1 (fr) * | 1988-11-07 | 1990-12-28 | Rhone Poulenc Chimie | Procede de preparation de nitrophenols |
| CN108164422A (zh) * | 2017-12-28 | 2018-06-15 | 大连泰瑞海铭化工集团有限公司 | 邻仲丁基-4,6-二硝基苯酚的生产方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3519693A (en) * | 1965-11-24 | 1970-07-07 | American Cyanamid Co | Nitration process for phenolic compounds |
| CH504403A (de) * | 1966-11-24 | 1971-03-15 | American Cyanamid Co | Verfahren zur Herstellung von p-Nitrophenol und p-Nitro-m-cresol |
| US3510527A (en) * | 1967-05-18 | 1970-05-05 | Hercules Inc | Preparation of p-nitrophenols |
-
1972
- 1972-05-26 CA CA143,114A patent/CA964674A/en not_active Expired
- 1972-06-13 GB GB2768772A patent/GB1345469A/en not_active Expired
- 1972-06-26 DE DE19722231157 patent/DE2231157C2/de not_active Expired
- 1972-06-28 IT IT5121472A patent/IT965860B/it active
- 1972-06-29 JP JP6453472A patent/JPS5637215B1/ja active Pending
- 1972-06-30 FR FR7223670A patent/FR2144395A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT965860B (it) | 1974-02-11 |
| CA964674A (en) | 1975-03-18 |
| JPS5637215B1 (enExample) | 1981-08-29 |
| FR2144395A5 (enExample) | 1973-02-09 |
| DE2231157A1 (de) | 1973-01-11 |
| GB1345469A (en) | 1974-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |