BE476170A - - Google Patents

Info

Publication number

BE476170A

BE476170A BE476170DA BE476170A BE 476170 A BE476170 A BE 476170A BE 476170D A BE476170D A BE 476170DA BE 476170 A BE476170 A BE 476170A

Authority

BE

Belgium

Prior art keywords

parts

bis

weight

hydrochloric acid

ether

Prior art date

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• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 238000009835 boiling Methods 0.000 description 9
• 239000000203 mixture Substances 0.000 description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 150000001875 compounds Chemical class 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• -1 hydrogen halides Chemical class 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 238000009833 condensation Methods 0.000 description 3
• 230000005494 condensation Effects 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
• 150000002825 nitriles Chemical class 0.000 description 3
• 229960000834 vinyl ether Drugs 0.000 description 3
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 239000012445 acidic reagent Substances 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 125000003118 aryl group Chemical group 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 230000002140 halogenating effect Effects 0.000 description 2
• 150000002367 halogens Chemical class 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• 239000000155 melt Substances 0.000 description 2
• 125000002560 nitrile group Chemical group 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 150000003141 primary amines Chemical class 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 125000001424 substituent group Chemical group 0.000 description 2
• WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 1
• DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
• SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
• BXEASFYXQCYZTR-UHFFFAOYSA-N 2-methylpiperidine-1-carbonitrile Chemical compound CC1CCCCN1C#N BXEASFYXQCYZTR-UHFFFAOYSA-N 0.000 description 1
• ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-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
• 230000001476 alcoholic effect Effects 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 150000003053 piperidines Chemical class 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 239000012485 toluene extract Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1