CH641442A5 - Verfahren zur herstellung von substituiertem malonsaeuredinitril. - Google Patents
Verfahren zur herstellung von substituiertem malonsaeuredinitril. Download PDFInfo
- Publication number
- CH641442A5 CH641442A5 CH1111979A CH1111979A CH641442A5 CH 641442 A5 CH641442 A5 CH 641442A5 CH 1111979 A CH1111979 A CH 1111979A CH 1111979 A CH1111979 A CH 1111979A CH 641442 A5 CH641442 A5 CH 641442A5
- Authority
- CH
- Switzerland
- Prior art keywords
- cyanogen chloride
- acetonitrile
- substituted
- reactor
- mol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical class N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 title description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 150000007960 acetonitrile Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- OFCTVAYVCDCQDA-UHFFFAOYSA-N 2-phenylpropanedinitrile Chemical compound N#CC(C#N)C1=CC=CC=C1 OFCTVAYVCDCQDA-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JHQBLYITVCBGTO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1 JHQBLYITVCBGTO-UHFFFAOYSA-N 0.000 description 1
- ZBVHRCUREGZYMH-UHFFFAOYSA-N 2-(4-fluorophenyl)propanedinitrile Chemical compound FC1=CC=C(C(C#N)C#N)C=C1 ZBVHRCUREGZYMH-UHFFFAOYSA-N 0.000 description 1
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- -1 alkali metal hydrogen carbonate Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/04—Preparation of carboxylic acid nitriles by reaction of cyanogen halides, e.g. ClCN, with organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782854197 DE2854197A1 (de) | 1978-12-15 | 1978-12-15 | Verfahren zur herstellung von substituierten malonsaeuredinitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641442A5 true CH641442A5 (de) | 1984-02-29 |
Family
ID=6057290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1111979A CH641442A5 (de) | 1978-12-15 | 1979-12-14 | Verfahren zur herstellung von substituiertem malonsaeuredinitril. |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5583742A (ja) |
| AT (1) | AT362774B (ja) |
| BE (1) | BE880557A (ja) |
| CH (1) | CH641442A5 (ja) |
| DE (1) | DE2854197A1 (ja) |
| FR (1) | FR2444027A1 (ja) |
| GB (1) | GB2037286B (ja) |
| IT (1) | IT7951079A0 (ja) |
| NL (1) | NL7907361A (ja) |
| SU (1) | SU1048982A3 (ja) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1173479A (en) * | 1966-11-28 | 1969-12-10 | Little Inc A | Improvements in method for Synthesizing Malononitrile |
-
1978
- 1978-12-15 DE DE19782854197 patent/DE2854197A1/de not_active Withdrawn
-
1979
- 1979-10-03 NL NL7907361A patent/NL7907361A/nl not_active Application Discontinuation
- 1979-11-19 FR FR7928483A patent/FR2444027A1/fr active Granted
- 1979-12-06 SU SU792847575A patent/SU1048982A3/ru active
- 1979-12-07 GB GB7942396A patent/GB2037286B/en not_active Expired
- 1979-12-11 BE BE6/47031A patent/BE880557A/fr not_active IP Right Cessation
- 1979-12-13 IT IT7951079A patent/IT7951079A0/it unknown
- 1979-12-14 CH CH1111979A patent/CH641442A5/de not_active IP Right Cessation
- 1979-12-14 AT AT0789479A patent/AT362774B/de active
- 1979-12-15 JP JP16220279A patent/JPS5583742A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2854197A1 (de) | 1980-07-03 |
| FR2444027A1 (fr) | 1980-07-11 |
| NL7907361A (nl) | 1980-06-17 |
| FR2444027B1 (ja) | 1984-01-27 |
| ATA789479A (de) | 1980-11-15 |
| SU1048982A3 (ru) | 1983-10-15 |
| AT362774B (de) | 1981-06-10 |
| IT7951079A0 (it) | 1979-12-13 |
| GB2037286A (en) | 1980-07-09 |
| GB2037286B (en) | 1983-04-13 |
| JPS5583742A (en) | 1980-06-24 |
| BE880557A (fr) | 1980-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |