NL8403885A - Werkwijze voor de bereiding van 3,4,5-trimethoxy-benzonitril. - Google Patents
Werkwijze voor de bereiding van 3,4,5-trimethoxy-benzonitril. Download PDFInfo
- Publication number
- NL8403885A NL8403885A NL8403885A NL8403885A NL8403885A NL 8403885 A NL8403885 A NL 8403885A NL 8403885 A NL8403885 A NL 8403885A NL 8403885 A NL8403885 A NL 8403885A NL 8403885 A NL8403885 A NL 8403885A
- Authority
- NL
- Netherlands
- Prior art keywords
- trimethoxy
- benzonitrile
- mol
- acid
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 41
- OSBQUSPVORCDCU-UHFFFAOYSA-N 3,4,5-trimethoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(OC)=C1OC OSBQUSPVORCDCU-UHFFFAOYSA-N 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title claims description 16
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims description 70
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 15
- 239000004202 carbamide Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- YCSGHMDKBZNXJC-UHFFFAOYSA-N 2,3,4-trimethoxybenzonitrile Chemical compound COC1=CC=C(C#N)C(OC)=C1OC YCSGHMDKBZNXJC-UHFFFAOYSA-N 0.000 claims 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- GGNMTJKRHHLJHH-UHFFFAOYSA-N Trimethylaethergallussaeure-amid Natural products COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QVZGKUBQTJBLKI-WDZFZDKYSA-N (nz)-n-[(3,4,5-trimethoxyphenyl)methylidene]hydroxylamine Chemical compound COC1=CC(\C=N/O)=CC(OC)=C1OC QVZGKUBQTJBLKI-WDZFZDKYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000013056 hazardous product Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU443883 | 1983-12-23 | ||
| HU834438A HU191909B (en) | 1983-12-23 | 1983-12-23 | Process for production of 3,4,5-trimetoxi-benzonitril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8403885A true NL8403885A (nl) | 1985-07-16 |
Family
ID=10967960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8403885A NL8403885A (nl) | 1983-12-23 | 1984-12-21 | Werkwijze voor de bereiding van 3,4,5-trimethoxy-benzonitril. |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS60214767A (it) |
| CN (1) | CN85101310A (it) |
| BE (1) | BE901284A (it) |
| CH (1) | CH660730A5 (it) |
| CS (1) | CS1024484A2 (it) |
| DE (1) | DE3446871A1 (it) |
| ES (1) | ES8600735A1 (it) |
| FI (1) | FI845107L (it) |
| FR (1) | FR2557106A1 (it) |
| GB (1) | GB2151626B (it) |
| HU (1) | HU191909B (it) |
| IT (1) | IT1178793B (it) |
| NL (1) | NL8403885A (it) |
| PL (1) | PL251144A1 (it) |
| RO (1) | RO92934B (it) |
| SE (1) | SE8406578L (it) |
| SU (1) | SU1452477A3 (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103772236B (zh) * | 2014-01-15 | 2016-04-13 | 华侨大学 | 一种苯甲腈衍生物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH494210A (de) * | 1968-03-27 | 1970-07-31 | Sandoz Ag | Verfahren zur Herstellung von Nitrilen |
| JPS5476544A (en) * | 1977-11-26 | 1979-06-19 | Sumitomo Chem Co Ltd | Preparation of p-cyanophenol |
| JPS5495541A (en) * | 1978-01-06 | 1979-07-28 | Sumitomo Chem Co Ltd | Production of cyanophenol |
-
1983
- 1983-12-23 HU HU834438A patent/HU191909B/hu not_active IP Right Cessation
-
1984
- 1984-12-17 BE BE1/11154A patent/BE901284A/fr not_active IP Right Cessation
- 1984-12-20 CH CH6072/84A patent/CH660730A5/de not_active IP Right Cessation
- 1984-12-21 NL NL8403885A patent/NL8403885A/nl not_active Application Discontinuation
- 1984-12-21 ES ES538924A patent/ES8600735A1/es not_active Expired
- 1984-12-21 CS CS8410244A patent/CS1024484A2/cs unknown
- 1984-12-21 IT IT24230/84A patent/IT1178793B/it active
- 1984-12-21 PL PL25114484A patent/PL251144A1/xx unknown
- 1984-12-21 SU SU847773698A patent/SU1452477A3/ru active
- 1984-12-21 RO RO116816A patent/RO92934B/ro unknown
- 1984-12-21 SE SE8406578A patent/SE8406578L/xx not_active Application Discontinuation
- 1984-12-21 DE DE19843446871 patent/DE3446871A1/de not_active Withdrawn
- 1984-12-21 FR FR8419641A patent/FR2557106A1/fr active Pending
- 1984-12-21 FI FI845107A patent/FI845107L/fi not_active Application Discontinuation
- 1984-12-21 JP JP59268716A patent/JPS60214767A/ja active Pending
- 1984-12-21 GB GB08432498A patent/GB2151626B/en not_active Expired
-
1985
- 1985-04-01 CN CN85101310A patent/CN85101310A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| RO92934A (ro) | 1987-12-31 |
| FI845107A0 (fi) | 1984-12-21 |
| BE901284A (fr) | 1985-06-17 |
| CS1024484A2 (en) | 1988-07-15 |
| GB8432498D0 (en) | 1985-02-06 |
| CN85101310A (zh) | 1987-01-24 |
| IT1178793B (it) | 1987-09-16 |
| GB2151626A (en) | 1985-07-24 |
| FR2557106A1 (fr) | 1985-06-28 |
| ES538924A0 (es) | 1985-11-01 |
| FI845107L (fi) | 1985-06-24 |
| ES8600735A1 (es) | 1985-11-01 |
| HUT36085A (en) | 1985-08-28 |
| SE8406578D0 (sv) | 1984-12-21 |
| SU1452477A3 (ru) | 1989-01-15 |
| DE3446871A1 (de) | 1985-07-11 |
| CH660730A5 (de) | 1987-06-15 |
| RO92934B (ro) | 1988-01-01 |
| GB2151626B (en) | 1987-04-29 |
| PL251144A1 (en) | 1985-10-08 |
| HU191909B (en) | 1987-04-28 |
| SE8406578L (sv) | 1985-06-24 |
| IT8424230A0 (it) | 1984-12-21 |
| JPS60214767A (ja) | 1985-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BI | The patent application has been withdrawn |