BE551542A - - Google Patents

Info

Publication number

BE551542A

BE551542A BE551542DA BE551542A BE 551542 A BE551542 A BE 551542A BE 551542D A BE551542D A BE 551542DA BE 551542 A BE551542 A BE 551542A

Authority

BE

Belgium

Prior art keywords

nitro

formaldehyde

ammonia

bis

temperature

Prior art date

Links

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• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 49
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 33
• 229910021529 ammonia Inorganic materials 0.000 claims description 15
• 238000000034 method Methods 0.000 claims description 14
• 239000000203 mixture Substances 0.000 claims description 13
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 239000007864 aqueous solution Substances 0.000 claims description 7
• NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 claims description 7
• 238000010992 reflux Methods 0.000 claims description 7
• ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• YQPAPBOZYOLZRW-UHFFFAOYSA-N 1-(1-nitrocyclohexyl)-N-[(1-nitrocyclohexyl)methyl]methanamine Chemical compound [N+](=O)([O-])C1(CCCCC1)CNCC1(CCCCC1)[N+](=O)[O-] YQPAPBOZYOLZRW-UHFFFAOYSA-N 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 239000002904 solvent Substances 0.000 claims description 5
• -1 1-nitrocyclohexylmethyl Chemical group 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 239000000243 solution Substances 0.000 description 7
• 150000002828 nitro derivatives Chemical class 0.000 description 5
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 239000000908 ammonium hydroxide Substances 0.000 description 4
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• RVUZKNAWVGDTBZ-UHFFFAOYSA-N Cl.[N+](=O)([O-])C1(CCCCC1)CNCC1(CCCCC1)[N+](=O)[O-] Chemical compound Cl.[N+](=O)([O-])C1(CCCCC1)CNCC1(CCCCC1)[N+](=O)[O-] RVUZKNAWVGDTBZ-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 239000003822 epoxy resin Substances 0.000 description 2
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
• 229920000647 polyepoxide Polymers 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 238000013019 agitation Methods 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 238000010923 batch production Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000008098 formaldehyde solution Substances 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• LACLQAUWSKAKQJ-UHFFFAOYSA-N nitrocycloheptane Chemical compound [O-][N+](=O)C1CCCCCC1 LACLQAUWSKAKQJ-UHFFFAOYSA-N 0.000 description 1
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000005057 refrigeration Methods 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000001256 steam distillation Methods 0.000 description 1
• 238000013517 stratification Methods 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1