JPH0522697B2 - - Google Patents
Info
- Publication number
- JPH0522697B2 JPH0522697B2 JP18817184A JP18817184A JPH0522697B2 JP H0522697 B2 JPH0522697 B2 JP H0522697B2 JP 18817184 A JP18817184 A JP 18817184A JP 18817184 A JP18817184 A JP 18817184A JP H0522697 B2 JPH0522697 B2 JP H0522697B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- methylbenzylidene
- phenylpropionitrile
- amino
- water
- 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 - Fee Related
Links
- -1 2-(α-methylbenzylidene)amino-3-phenylpropionitrile Chemical compound 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
- 229940073608 benzyl chloride Drugs 0.000 description 5
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SCLCDBISIMXAPM-UHFFFAOYSA-N 2-(benzylideneamino)propanenitrile Chemical compound N#CC(C)N=CC1=CC=CC=C1 SCLCDBISIMXAPM-UHFFFAOYSA-N 0.000 description 4
- ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DDOYWSXVQGNRIK-UHFFFAOYSA-N 2-(benzhydrylideneamino)-3-phenylpropanenitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=NC(C#N)CC1=CC=CC=C1 DDOYWSXVQGNRIK-UHFFFAOYSA-N 0.000 description 1
- YVDSUPOAMPCYSC-UHFFFAOYSA-N 2-amino-3,3-diphenylprop-2-enenitrile Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)=C(C#N)N YVDSUPOAMPCYSC-UHFFFAOYSA-N 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- VBEKGXAPCZTFJW-UHFFFAOYSA-N benzene;octane Chemical compound C1=CC=CC=C1.CCCCCCCC VBEKGXAPCZTFJW-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18817184A JPS6165857A (ja) | 1984-09-10 | 1984-09-10 | ２−（α−メチルベンジリデン）アミノ−３−フエニルプロピオニトリルおよびその製造法 |
| DE19853531084 DE3531084A1 (de) | 1984-08-30 | 1985-08-30 | Verfahren zur herstellung von phenylalanin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18817184A JPS6165857A (ja) | 1984-09-10 | 1984-09-10 | ２−（α−メチルベンジリデン）アミノ−３−フエニルプロピオニトリルおよびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6165857A JPS6165857A (ja) | 1986-04-04 |
| JPH0522697B2 true JPH0522697B2 (zh) | 1993-03-30 |
Family
ID=16218997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18817184A Granted JPS6165857A (ja) | 1984-08-30 | 1984-09-10 | ２−（α−メチルベンジリデン）アミノ−３−フエニルプロピオニトリルおよびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6165857A (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015072567A1 (ja) | 2013-11-18 | 2015-05-21 | 日立造船株式会社 | 脱硝触媒、およびその製造方法 |
-
1984
- 1984-09-10 JP JP18817184A patent/JPS6165857A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015072567A1 (ja) | 2013-11-18 | 2015-05-21 | 日立造船株式会社 | 脱硝触媒、およびその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6165857A (ja) | 1986-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |