CA1048546A - Process for preparing 4-chloro-2,5-dimethoxy aniline - Google Patents
Process for preparing 4-chloro-2,5-dimethoxy anilineInfo
- Publication number
- CA1048546A CA1048546A CA75240271A CA240271A CA1048546A CA 1048546 A CA1048546 A CA 1048546A CA 75240271 A CA75240271 A CA 75240271A CA 240271 A CA240271 A CA 240271A CA 1048546 A CA1048546 A CA 1048546A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- phosphate
- disodium
- nitro compound
- promotor
- 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
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002245 particle Substances 0.000 claims abstract description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 19
- 150000002828 nitro derivatives Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910021538 borax Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 2
- GOBGCUAZYIPRTM-UHFFFAOYSA-N [Na+].[Na+].OB(O)OB([O-])[O-] Chemical compound [Na+].[Na+].OB(O)OB([O-])[O-] GOBGCUAZYIPRTM-UHFFFAOYSA-N 0.000 claims description 2
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 5
- 239000010452 phosphate Substances 0.000 claims 5
- 239000012429 reaction media Substances 0.000 claims 1
- ORLPGMKKCAEWOW-UHFFFAOYSA-N 1-chloro-2,5-dimethoxy-4-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=C(OC)C=C1Cl ORLPGMKKCAEWOW-UHFFFAOYSA-N 0.000 abstract description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008878 coupling Effects 0.000 abstract description 2
- 238000010168 coupling process Methods 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- DWVNLBRNGAANPI-UHFFFAOYSA-N 1,2-dimethoxy-3-nitrobenzene Chemical compound COC1=CC=CC([N+]([O-])=O)=C1OC DWVNLBRNGAANPI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy 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 |
|---|---|---|---|
| DE2455704A DE2455704C3 (de) | 1974-11-25 | 1974-11-25 | Verfahren zur Herstellung von 4-Chlor-23-dimethoxy anilin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048546A true CA1048546A (en) | 1979-02-13 |
Family
ID=5931670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75240271A Expired CA1048546A (en) | 1974-11-25 | 1975-11-24 | Process for preparing 4-chloro-2,5-dimethoxy aniline |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2521303B2 (de) * | 1975-05-13 | 1977-09-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,5-dimethoxy-4-chloranilin |
| DE3821013A1 (de) * | 1988-06-22 | 1989-12-28 | Hoechst Ag | Verfahren zur herstellung von 4-chlor-2,5-dimethoxyanilin |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186722A (en) * | 1940-01-09 | Diazonium compounds and process of | ||
| US1679211A (en) * | 1921-07-02 | 1928-07-31 | Nat Aniline & Chem Co Inc | Method of sulfonation |
| BE791300A (fr) * | 1971-11-11 | 1973-05-14 | Hoechst Ag | Procede de preparation de la chloro-4 dimethoxy-2,5 aniline |
| DE2240849C3 (de) * | 1972-08-19 | 1975-03-20 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von Aminobenzolen |
-
1974
- 1974-11-25 DE DE2455704A patent/DE2455704C3/de not_active Expired
-
1975
- 1975-11-21 CH CH1513475A patent/CH594600A5/xx not_active IP Right Cessation
- 1975-11-21 IT IT29554/75A patent/IT1049861B/it active
- 1975-11-22 JP JP50139782A patent/JPS5913497B2/ja not_active Expired
- 1975-11-24 BR BR7507755*A patent/BR7507755A/pt unknown
- 1975-11-24 US US05/634,634 patent/US4082803A/en not_active Expired - Lifetime
- 1975-11-24 CA CA75240271A patent/CA1048546A/en not_active Expired
- 1975-11-25 FR FR7535918A patent/FR2291969A1/fr active Granted
- 1975-11-25 GB GB48445/75A patent/GB1527892A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2291969B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-01-05 |
| DE2455704B2 (de) | 1977-10-20 |
| JPS5913497B2 (ja) | 1984-03-30 |
| DE2455704A1 (de) | 1976-08-12 |
| CH594600A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-13 |
| GB1527892A (en) | 1978-10-11 |
| US4082803A (en) | 1978-04-04 |
| DE2455704C3 (de) | 1978-06-08 |
| FR2291969A1 (fr) | 1976-06-18 |
| IT1049861B (it) | 1981-02-10 |
| BR7507755A (pt) | 1976-08-10 |
| JPS5175033A (en) | 1976-06-29 |
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