JPS61165358A - ２−アリ−ルプロピオニトリルの製造方法 - Google Patents
２−アリ−ルプロピオニトリルの製造方法Info
- Publication number
- JPS61165358A JPS61165358A JP60005259A JP525985A JPS61165358A JP S61165358 A JPS61165358 A JP S61165358A JP 60005259 A JP60005259 A JP 60005259A JP 525985 A JP525985 A JP 525985A JP S61165358 A JPS61165358 A JP S61165358A
- Authority
- JP
- Japan
- Prior art keywords
- arylacetonitrile
- amount
- arylpropionitrile
- formaldehyde
- carbon monoxide
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 22
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 7
- 150000003284 rhodium compounds Chemical class 0.000 claims abstract description 7
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- -1 triethylamine) Chemical class 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- 230000001035 methylating effect Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 abstract 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- NVAOLENBKNECGF-UHFFFAOYSA-N 2-phenylpropanenitrile Chemical compound N#CC(C)C1=CC=CC=C1 NVAOLENBKNECGF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical class O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical class [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- MMRXYMKDBFSWJR-UHFFFAOYSA-K rhodium(3+);tribromide Chemical class [Br-].[Br-].[Br-].[Rh+3] MMRXYMKDBFSWJR-UHFFFAOYSA-K 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60005259A JPS61165358A (ja) | 1985-01-16 | 1985-01-16 | ２−アリ−ルプロピオニトリルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60005259A JPS61165358A (ja) | 1985-01-16 | 1985-01-16 | ２−アリ−ルプロピオニトリルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61165358A true JPS61165358A (ja) | 1986-07-26 |
| JPH0149347B2 JPH0149347B2 (enrdf_load_stackoverflow) | 1989-10-24 |
Family
ID=11606228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60005259A Granted JPS61165358A (ja) | 1985-01-16 | 1985-01-16 | ２−アリ−ルプロピオニトリルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61165358A (enrdf_load_stackoverflow) |
-
1985
- 1985-01-16 JP JP60005259A patent/JPS61165358A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0149347B2 (enrdf_load_stackoverflow) | 1989-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2021195751A1 (en) | Catalytic cannabigerol processes and precursors | |
| JPS6145611B2 (enrdf_load_stackoverflow) | ||
| JPH05506668A (ja) | アルブテロール、およびその中間体であるアセタール、ヘミアセタールおよびアリールグリオキサール水化物の製造方法 | |
| JPH059158A (ja) | 光学活性アミン類の製法 | |
| JPS5840932B2 (ja) | アリ−ルエ−テルの製造法 | |
| JPS61165358A (ja) | ２−アリ−ルプロピオニトリルの製造方法 | |
| JPH02290851A (ja) | ２―クロロ―５―アミノメチルーピリジンの製造方法 | |
| JP2002179622A (ja) | ４−アセトキシスチレンの製造方法 | |
| US6545166B2 (en) | Process for producing spiro acetal derivative | |
| CN112047816B (zh) | 三甲基卤硅烷催化醇合成醚的方法 | |
| US2541747A (en) | Production of hydroxyl compounds by hydrolysis of tetrahydropyryl ethers | |
| JPS62185032A (ja) | １−（１−ヒドロキシエチル）−アルキルシクロヘキサンの製造方法 | |
| Shi et al. | A new method for synthesizing terminal olefins from esters using the Corey–Chaykovsky reagent | |
| CN100509722C (zh) | 3,5-二氟联苯衍生物的制备方法 | |
| KR102712847B1 (ko) | 신규 구조의 유기인계 촉매 및 이를 이용한 선형 디니트릴의 제조방법 | |
| JPS6225655B2 (enrdf_load_stackoverflow) | ||
| JPS632958A (ja) | アリル型アミンの製造法 | |
| JP3691235B2 (ja) | 光学活性ピペリジン類の製造方法 | |
| JP4240239B2 (ja) | 脂環式化合物の製造方法 | |
| KR100935016B1 (ko) | 1-(2-하이드록시페닐)부타-2-엔-1-온 또는 크로만-4-온 유도체의 제조방법 | |
| JPH11217362A (ja) | β−ヒドラジノエステル類並びにピラゾリジノン類、 ピラゾロン類およびβ−アミノ酸誘導体の製造方法 | |
| JP4243397B2 (ja) | 新規な不飽和２級アルコールおよびその製造法 | |
| JP3569428B2 (ja) | ホモアリルアミン類の製造方法 | |
| JPS6023355A (ja) | ３−フエニル−２−アミノ−２−メチルプロピオン酸アミド類の製造法 | |
| JPH05990A (ja) | α−アルキルアクロレインの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |