DE1965384B2 - - Google Patents
Info
- Publication number
- DE1965384B2 DE1965384B2 DE19691965384 DE1965384A DE1965384B2 DE 1965384 B2 DE1965384 B2 DE 1965384B2 DE 19691965384 DE19691965384 DE 19691965384 DE 1965384 A DE1965384 A DE 1965384A DE 1965384 B2 DE1965384 B2 DE 1965384B2
- Authority
- DE
- Germany
- Prior art keywords
- aqueous
- solution
- sodium
- alkali metal
- aqueous solution
- 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.)
- Granted
Links
- 239000000243 solution Substances 0.000 claims description 28
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 21
- 229910017604 nitric acid Inorganic materials 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical class OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 16
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 16
- 230000003647 oxidation Effects 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- -1 alkali metal phenolates Chemical class 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 229940031826 phenolate Drugs 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 26
- 230000009935 nitrosation Effects 0.000 description 21
- 238000007034 nitrosation reaction Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 235000010288 sodium nitrite Nutrition 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- XGCZABZDVJOWTL-UHFFFAOYSA-N 3-methyl-4-nitrosophenol Chemical compound CC1=CC(O)=CC=C1N=O XGCZABZDVJOWTL-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 150000002832 nitroso derivatives Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- DVHCUTKQUSEJRY-UHFFFAOYSA-N 2-methyl-3-nitrosophenol Chemical compound CC1=C(O)C=CC=C1N=O DVHCUTKQUSEJRY-UHFFFAOYSA-N 0.000 description 2
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 2
- WDMVCCFXKFPDJG-UHFFFAOYSA-N CC1(C=CC(C)=CC1)[O-].[Na+] Chemical compound CC1(C=CC(C)=CC1)[O-].[Na+] WDMVCCFXKFPDJG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FKDPHYNQLRYLRN-UHFFFAOYSA-N N(=O)C1=CC(C(C=C1)(C)O)C Chemical compound N(=O)C1=CC(C(C=C1)(C)O)C FKDPHYNQLRYLRN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- WHQZPTTYEYXMIZ-UHFFFAOYSA-M sodium;3-hydroxy-2-methylbenzoate Chemical compound [Na+].CC1=C(O)C=CC=C1C([O-])=O WHQZPTTYEYXMIZ-UHFFFAOYSA-M 0.000 description 2
- QOINKMNRLBCJOP-UHFFFAOYSA-M sodium;3-methylphenolate Chemical compound [Na+].CC1=CC=CC([O-])=C1 QOINKMNRLBCJOP-UHFFFAOYSA-M 0.000 description 2
- NAGJRPZQLWHEHH-UHFFFAOYSA-M sodium;4-nitrosophenolate Chemical compound [Na+].[O-]C1=CC=C(N=O)C=C1 NAGJRPZQLWHEHH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JZSQQJQUQTUIBB-UHFFFAOYSA-N 1,6-dimethyl-4-nitrocyclohexa-2,4-dien-1-ol Chemical compound [N+](=O)([O-])C1=CC(C(C=C1)(C)O)C JZSQQJQUQTUIBB-UHFFFAOYSA-N 0.000 description 1
- CKGDFIYUWVYPDN-UHFFFAOYSA-N 1,6-dimethyl-5-nitrosocyclohexa-2,4-dien-1-ol Chemical compound N(=O)C=1C(C(C=CC1)(C)O)C CKGDFIYUWVYPDN-UHFFFAOYSA-N 0.000 description 1
- FVVBEMKXRUJJFF-UHFFFAOYSA-N 2-methyl-4-nitrophenol;3-methyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC=C1O.CC1=CC(O)=CC=C1[N+]([O-])=O FVVBEMKXRUJJFF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- SEEZWGFVHCMHJF-UHFFFAOYSA-N 2-nitrosophenol Chemical class OC1=CC=CC=C1N=O SEEZWGFVHCMHJF-UHFFFAOYSA-N 0.000 description 1
- SDBMJFLEJPLYFS-UHFFFAOYSA-N 3-methyl-2-nitrosophenol Chemical compound CC1=CC=CC(O)=C1N=O SDBMJFLEJPLYFS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- TVEVWAJRUGFBFE-UHFFFAOYSA-M CC(C(C([O-])=O)=C(C=C1)N=O)=C1O.[Na+] Chemical compound CC(C(C([O-])=O)=C(C=C1)N=O)=C1O.[Na+] TVEVWAJRUGFBFE-UHFFFAOYSA-M 0.000 description 1
- WJDBTECFDYOXRN-UHFFFAOYSA-M CC(C(C([O-])=O)=C(C=C1)O)=C1N=O.[Na+] Chemical compound CC(C(C([O-])=O)=C(C=C1)O)=C1N=O.[Na+] WJDBTECFDYOXRN-UHFFFAOYSA-M 0.000 description 1
- BLPJJRCJESZTCC-UHFFFAOYSA-N CC=1C=C(C=CC1[N+](=O)[O-])O.CC=1C=C(C=CC1[N+](=O)[O-])O Chemical compound CC=1C=C(C=CC1[N+](=O)[O-])O.CC=1C=C(C=CC1[N+](=O)[O-])O BLPJJRCJESZTCC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Inorganic materials [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010850 salt effect Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003739 xylenols Chemical class 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 |
|---|---|---|---|
| FR182308 | 1968-12-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1965384A1 DE1965384A1 (de) | 1970-07-23 |
| DE1965384B2 true DE1965384B2 (en:Method) | 1980-11-20 |
| DE1965384C3 DE1965384C3 (de) | 1981-09-24 |
Family
ID=8659569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691965384 Expired DE1965384C3 (de) | 1968-12-31 | 1969-12-30 | Verfahren zur Herstellung von p-Nitropheonlen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE743851A (en:Method) |
| CH (1) | CH525854A (en:Method) |
| DE (1) | DE1965384C3 (en:Method) |
| ES (1) | ES375108A1 (en:Method) |
| FR (1) | FR1602746A (en:Method) |
| GB (1) | GB1296370A (en:Method) |
| NL (1) | NL169871C (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3903157C2 (de) * | 1989-02-02 | 2000-11-09 | Scheffler Gmbh & Co Kg | Lüfterkappe zur Hinterlüftung von Dächern |
| FR2705672B1 (fr) * | 1993-05-26 | 1995-07-21 | Rhone Poulenc Chimie | Procédé de préparation de nitrophénols. |
| JP2951600B2 (ja) * | 1996-08-23 | 1999-09-20 | 純正化學株式会社 | フェノール誘導体の選択的ニトロ化方法 |
| FR3109580B1 (fr) * | 2020-04-27 | 2023-03-10 | Ipsomedic | Procédé de synthèse du paracétamol en continu |
| CN113603533A (zh) * | 2021-08-13 | 2021-11-05 | 辽宁拓展农业发展有限公司 | 一种尿素增效剂用螯合液及应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2234692A (en) * | 1939-10-31 | 1941-03-11 | Eastman Kodak Co | Process of making p-nitrosophenol |
| US3320324A (en) * | 1964-01-08 | 1967-05-16 | Hercules Inc | Process for the manufacture of p-nitrosophenol |
| US3519693A (en) * | 1965-11-24 | 1970-07-07 | American Cyanamid Co | Nitration process for phenolic compounds |
-
1968
- 1968-12-31 FR FR1602746D patent/FR1602746A/fr not_active Expired
-
1969
- 1969-12-26 CH CH1923069A patent/CH525854A/fr not_active IP Right Cessation
- 1969-12-29 NL NL6919521A patent/NL169871C/xx not_active IP Right Cessation
- 1969-12-30 DE DE19691965384 patent/DE1965384C3/de not_active Expired
- 1969-12-30 GB GB1296370D patent/GB1296370A/en not_active Expired
- 1969-12-30 BE BE743851D patent/BE743851A/xx not_active IP Right Cessation
- 1969-12-31 ES ES375108A patent/ES375108A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH525854A (fr) | 1972-07-31 |
| GB1296370A (en:Method) | 1972-11-15 |
| ES375108A1 (es) | 1972-03-16 |
| BE743851A (en:Method) | 1970-06-30 |
| DE1965384C3 (de) | 1981-09-24 |
| NL6919521A (en:Method) | 1970-07-02 |
| NL169871C (nl) | 1982-09-01 |
| FR1602746A (en:Method) | 1971-01-18 |
| NL169871B (nl) | 1982-04-01 |
| DE1965384A1 (de) | 1970-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8380 | Miscellaneous part iii |
Free format text: DIE BEZEICHNUNG LAUTET RICHTIG: VERFAHREN ZUR HERSTELLUNG VON P-NITROPHENOLEN |
|
| XX | Miscellaneous: |
Free format text: DIE BEZEICHNUNG LAUTET RICHTIG:VERFAHREN ZUR HERSTELLUNG VON P-NITROPHENOLEN |