DE1793109A1 - Verfahren zur Herstellung von 3,6-Diaminopseudocumol und seiner Salze mit Saeuren - Google Patents
Verfahren zur Herstellung von 3,6-Diaminopseudocumol und seiner Salze mit SaeurenInfo
- Publication number
- DE1793109A1 DE1793109A1 DE19681793109 DE1793109A DE1793109A1 DE 1793109 A1 DE1793109 A1 DE 1793109A1 DE 19681793109 DE19681793109 DE 19681793109 DE 1793109 A DE1793109 A DE 1793109A DE 1793109 A1 DE1793109 A1 DE 1793109A1
- Authority
- DE
- Germany
- Prior art keywords
- aqueous medium
- catalyst
- salts
- acids
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 239000002253 acid Substances 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 7
- 150000007513 acids Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- IFUXXUAAJBKDGO-UHFFFAOYSA-N 2,3,5-trimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=C(C)C(C)=C1N IFUXXUAAJBKDGO-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000003610 charcoal Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- 241001122767 Theaceae Species 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- BEKMUYHMJNEHDQ-UHFFFAOYSA-N 1,3,4-trimethyl-2,5-dinitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=C(C)C(C)=C1[N+]([O-])=O BEKMUYHMJNEHDQ-UHFFFAOYSA-N 0.000 description 1
- KYKZZQUNWDJVDN-UHFFFAOYSA-N 1-(dinitromethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(C([N+]([O-])=O)[N+]([O-])=O)C(C)=C1 KYKZZQUNWDJVDN-UHFFFAOYSA-N 0.000 description 1
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08296/68A GB1168305A (en) | 1967-08-02 | 1967-08-02 | Preparation of 3,6-Diamino-Pseudocumene |
| GB3554667 | 1967-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793109A1 true DE1793109A1 (de) | 1972-02-03 |
Family
ID=26253296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681793109 Pending DE1793109A1 (de) | 1967-08-02 | 1968-08-02 | Verfahren zur Herstellung von 3,6-Diaminopseudocumol und seiner Salze mit Saeuren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3654366A (enExample) |
| BE (1) | BE718614A (enExample) |
| CH (1) | CH502299A (enExample) |
| DE (1) | DE1793109A1 (enExample) |
| FR (1) | FR1576766A (enExample) |
| GB (1) | GB1168305A (enExample) |
| NL (1) | NL6810224A (enExample) |
-
1967
- 1967-08-02 GB GB08296/68A patent/GB1168305A/en not_active Expired
-
1968
- 1968-07-17 US US745367A patent/US3654366A/en not_active Expired - Lifetime
- 1968-07-19 NL NL6810224A patent/NL6810224A/xx unknown
- 1968-07-26 BE BE718614D patent/BE718614A/xx unknown
- 1968-08-01 FR FR1576766D patent/FR1576766A/fr not_active Expired
- 1968-08-02 DE DE19681793109 patent/DE1793109A1/de active Pending
- 1968-08-02 CH CH1167468A patent/CH502299A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1576766A (enExample) | 1969-08-01 |
| US3654366A (en) | 1972-04-04 |
| BE718614A (enExample) | 1969-01-27 |
| NL6810224A (enExample) | 1969-02-04 |
| GB1168305A (en) | 1969-10-22 |
| CH502299A (de) | 1971-01-31 |
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