DE3020236A1 - Verfahren zur herstellung von o- beziehungsweise p-nitrophenylalkoholen - Google Patents
Verfahren zur herstellung von o- beziehungsweise p-nitrophenylalkoholenInfo
- Publication number
- DE3020236A1 DE3020236A1 DE19803020236 DE3020236A DE3020236A1 DE 3020236 A1 DE3020236 A1 DE 3020236A1 DE 19803020236 DE19803020236 DE 19803020236 DE 3020236 A DE3020236 A DE 3020236A DE 3020236 A1 DE3020236 A1 DE 3020236A1
- Authority
- DE
- Germany
- Prior art keywords
- mol
- general formula
- derivatives
- nitrotoluene
- methylol
- 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.)
- Withdrawn
Links
- -1 P-NITROPHENYL ALCOHOLS Chemical class 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 55
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical class CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 27
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical class CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- 238000007031 hydroxymethylation reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- SLRIOXRBAPBGEI-UHFFFAOYSA-N 2-(2-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC=C1[N+]([O-])=O SLRIOXRBAPBGEI-UHFFFAOYSA-N 0.000 description 22
- 239000002585 base Substances 0.000 description 17
- 229960004279 formaldehyde Drugs 0.000 description 14
- 235000019256 formaldehyde Nutrition 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229930040373 Paraformaldehyde Natural products 0.000 description 9
- 229920002866 paraformaldehyde Polymers 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000007858 starting material Substances 0.000 description 7
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 6
- 238000010183 spectrum analysis Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 5
- QJANIQCEDPJNLO-UHFFFAOYSA-N (2-methyl-3-nitrophenyl)methanol Chemical class CC1=C(CO)C=CC=C1[N+]([O-])=O QJANIQCEDPJNLO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 3
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 3
- KZJIJJUXIGOECZ-UHFFFAOYSA-N 2-(2-nitrophenyl)propane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=C1[N+]([O-])=O KZJIJJUXIGOECZ-UHFFFAOYSA-N 0.000 description 3
- RTZOGYCMIMOVHU-UHFFFAOYSA-N 4-methoxy-2-methyl-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(C)=C1 RTZOGYCMIMOVHU-UHFFFAOYSA-N 0.000 description 3
- 238000005705 Cannizzaro reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ORYNFHRBOIYIPE-UHFFFAOYSA-N 2-(4-fluoro-2-nitrophenyl)ethanol Chemical compound OCCC1=CC=C(F)C=C1[N+]([O-])=O ORYNFHRBOIYIPE-UHFFFAOYSA-N 0.000 description 2
- IKMXRUOZUUKSON-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanol Chemical compound OCCC1=CC=C([N+]([O-])=O)C=C1 IKMXRUOZUUKSON-UHFFFAOYSA-N 0.000 description 2
- SKWTUNAAJNDEIK-UHFFFAOYSA-N 4-fluoro-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(F)C=C1[N+]([O-])=O SKWTUNAAJNDEIK-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
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004999 nitroaryl group Chemical group 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- DSDBYQDNNWCLHL-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1[N+]([O-])=O DSDBYQDNNWCLHL-UHFFFAOYSA-N 0.000 description 1
- PECHLROPLSUPDA-UHFFFAOYSA-N 2-(3-methoxy-2-nitrophenyl)ethanol Chemical compound COC1=CC=CC(CCO)=C1[N+]([O-])=O PECHLROPLSUPDA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79RE648A HU177886B (en) | 1979-05-29 | 1979-05-29 | Process for the selective hydroxymethylation of nitro-toluenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3020236A1 true DE3020236A1 (de) | 1980-12-11 |
Family
ID=11000777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803020236 Withdrawn DE3020236A1 (de) | 1979-05-29 | 1980-05-28 | Verfahren zur herstellung von o- beziehungsweise p-nitrophenylalkoholen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4299992A (OSRAM) |
| JP (1) | JPS5677245A (OSRAM) |
| DE (1) | DE3020236A1 (OSRAM) |
| GB (1) | GB2051064B (OSRAM) |
| HU (1) | HU177886B (OSRAM) |
| SE (1) | SE8003929L (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4497966A (en) * | 1982-09-14 | 1985-02-05 | Shell Oil Company | Process for the preparation of nitrophenylalkanols |
| WO2006002712A1 (de) * | 2004-06-30 | 2006-01-12 | Henkel Kommanditgesellschaft Auf Aktien | Phenylpropandiol-farbstoffvorprodukte |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258296A (en) * | 1988-04-29 | 1993-11-02 | The Trustees Of The University Of Pennsylvania | Non-steroid and non-prostanoid inhibitors of steroid and prostaglandin transfroming enzymes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3405183A (en) * | 1964-05-07 | 1968-10-08 | Upjohn Co | Aralkanols and process for their preparation |
| SE375759B (OSRAM) | 1967-06-14 | 1975-04-28 | Bofors Ab | |
| JPS5852981B2 (ja) * | 1976-04-05 | 1983-11-26 | 三井化学株式会社 | ２−（ｏ−ニトロフエニル）エタノ−ル類の製造方法 |
| JPS52139035A (en) * | 1976-05-17 | 1977-11-19 | Mitsui Petrochem Ind Ltd | Synthesis of 2-(nitroaryl)ethanols |
-
1979
- 1979-05-29 HU HU79RE648A patent/HU177886B/hu not_active IP Right Cessation
-
1980
- 1980-05-20 US US06/151,597 patent/US4299992A/en not_active Expired - Lifetime
- 1980-05-27 SE SE8003929A patent/SE8003929L/xx not_active Application Discontinuation
- 1980-05-28 JP JP7129780A patent/JPS5677245A/ja active Granted
- 1980-05-28 DE DE19803020236 patent/DE3020236A1/de not_active Withdrawn
- 1980-05-29 GB GB8017660A patent/GB2051064B/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4497966A (en) * | 1982-09-14 | 1985-02-05 | Shell Oil Company | Process for the preparation of nitrophenylalkanols |
| WO2006002712A1 (de) * | 2004-06-30 | 2006-01-12 | Henkel Kommanditgesellschaft Auf Aktien | Phenylpropandiol-farbstoffvorprodukte |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0147456B2 (OSRAM) | 1989-10-13 |
| US4299992A (en) | 1981-11-10 |
| SE8003929L (sv) | 1980-11-30 |
| JPS5677245A (en) | 1981-06-25 |
| GB2051064A (en) | 1981-01-14 |
| HU177886B (en) | 1982-01-28 |
| GB2051064B (en) | 1983-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |