CH622499A5 - - Google Patents
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- Publication number
- CH622499A5 CH622499A5 CH1018177A CH1018177A CH622499A5 CH 622499 A5 CH622499 A5 CH 622499A5 CH 1018177 A CH1018177 A CH 1018177A CH 1018177 A CH1018177 A CH 1018177A CH 622499 A5 CH622499 A5 CH 622499A5
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropyl
- chloride
- weight
- bromide
- halophenylacetonitrile
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- -1 isopropyl halide Chemical class 0.000 claims description 18
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical group ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 12
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 10
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical group CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- QUXGMICRFKKOES-UHFFFAOYSA-M (4-chlorophenyl)methyl-triethylazanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=C(Cl)C=C1 QUXGMICRFKKOES-UHFFFAOYSA-M 0.000 claims description 2
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 claims description 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 2
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 10
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 7
- RBGSZIRWNWQDOK-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanenitrile Chemical compound CC(C)C(C#N)C1=CC=C(Cl)C=C1 RBGSZIRWNWQDOK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- IFYAJVCCCYPHHN-UHFFFAOYSA-M (4-chlorophenyl)methyl-triethylazanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=C(Cl)C=C1 IFYAJVCCCYPHHN-UHFFFAOYSA-M 0.000 description 1
- FXXLSLVDZPRCNA-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)acetonitrile Chemical compound CC1=CC(CC#N)=CC=C1Cl FXXLSLVDZPRCNA-UHFFFAOYSA-N 0.000 description 1
- ZGJPBXVBZQACAL-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C#N)(C(C)C)C1=CC=C(Cl)C=C1 ZGJPBXVBZQACAL-UHFFFAOYSA-N 0.000 description 1
- WZSOEUAQKKEHFE-UHFFFAOYSA-N 2-chloro-2-phenylacetonitrile Chemical compound N#CC(Cl)C1=CC=CC=C1 WZSOEUAQKKEHFE-UHFFFAOYSA-N 0.000 description 1
- YWFGCYQKXLSDKT-UHFFFAOYSA-N 3-(2,3-diethylphenyl)pentan-3-ylazanium;chloride Chemical compound [Cl-].CCC1=CC=CC(C([NH3+])(CC)CC)=C1CC YWFGCYQKXLSDKT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000007962 benzene acetonitriles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10091676A JPS5325538A (en) | 1976-08-23 | 1976-08-23 | Preparation of 3-methyl-2-(4-halogenophenyl)butyronitril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622499A5 true CH622499A5 (es) | 1981-04-15 |
Family
ID=14286652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1018177A CH622499A5 (es) | 1976-08-23 | 1977-08-19 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4144264A (es) |
| JP (1) | JPS5325538A (es) |
| BE (1) | BE857989A (es) |
| BR (1) | BR7705485A (es) |
| CH (1) | CH622499A5 (es) |
| DE (1) | DE2737945A1 (es) |
| DK (1) | DK372577A (es) |
| FR (1) | FR2362826A1 (es) |
| GB (1) | GB1573686A (es) |
| IT (1) | IT1079923B (es) |
| NL (1) | NL7709237A (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1591214A (en) * | 1977-05-23 | 1981-06-17 | Sumitomo Chemical Co | Recovery of a tertiary amine or quaternary ammonium catalyst used in the production of a-substituted benzyl nitriles |
| JPS56292A (en) * | 1979-06-18 | 1981-01-06 | Shimizu Shoji Kk | Improving soldering property of nickel plating |
| DK301981A (da) * | 1980-07-28 | 1982-01-29 | Stauffer Chemical Co | Fremgangsmaade til fremstilling af 3-alkyl-2-p-chlorphenylbutyrylnitril |
| JPS60162199U (ja) * | 1984-04-05 | 1985-10-28 | 株式会社北光社 | 止水シ−ト |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5163145A (en) * | 1974-11-26 | 1976-06-01 | Sumitomo Chemical Co | 33 mechiru 22 * 44 harogenofueniru * buchironitoriruno seizoho |
-
1976
- 1976-08-23 JP JP10091676A patent/JPS5325538A/ja active Granted
-
1977
- 1977-08-12 GB GB33875/77A patent/GB1573686A/en not_active Expired
- 1977-08-18 BR BR7705485A patent/BR7705485A/pt unknown
- 1977-08-19 US US05/826,088 patent/US4144264A/en not_active Expired - Lifetime
- 1977-08-19 IT IT50723/77A patent/IT1079923B/it active
- 1977-08-19 CH CH1018177A patent/CH622499A5/fr not_active IP Right Cessation
- 1977-08-22 NL NL7709237A patent/NL7709237A/xx not_active Application Discontinuation
- 1977-08-22 BE BE180331A patent/BE857989A/xx not_active IP Right Cessation
- 1977-08-22 DK DK372577A patent/DK372577A/da not_active Application Discontinuation
- 1977-08-23 FR FR7725739A patent/FR2362826A1/fr active Granted
- 1977-08-23 DE DE19772737945 patent/DE2737945A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BE857989A (fr) | 1977-12-16 |
| JPS5325538A (en) | 1978-03-09 |
| GB1573686A (en) | 1980-08-28 |
| US4144264A (en) | 1979-03-13 |
| DK372577A (da) | 1978-02-24 |
| IT1079923B (it) | 1985-05-13 |
| FR2362826B1 (es) | 1980-02-08 |
| DE2737945A1 (de) | 1978-03-02 |
| JPS5756909B2 (es) | 1982-12-02 |
| FR2362826A1 (fr) | 1978-03-24 |
| NL7709237A (nl) | 1978-02-27 |
| BR7705485A (pt) | 1978-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |