BE524653A - - Google Patents
Info
- Publication number
- BE524653A BE524653A BE524653DA BE524653A BE 524653 A BE524653 A BE 524653A BE 524653D A BE524653D A BE 524653DA BE 524653 A BE524653 A BE 524653A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- preparation according
- bis
- alcohol
- melting point
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 24
- -1 di-substituted benzene Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 7
- 230000002829 reduced Effects 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 238000007792 addition Methods 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000005466 alkylenyl group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims description 3
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000006722 reduction reaction Methods 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 230000001681 protective Effects 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- 238000002844 melting Methods 0.000 description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- 238000009835 boiling Methods 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000005903 acid hydrolysis reaction Methods 0.000 description 7
- 239000008079 hexane Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 229960000583 Acetic Acid Drugs 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000005712 crystallization Effects 0.000 description 5
- 230000017858 demethylation Effects 0.000 description 5
- 238000010520 demethylation reaction Methods 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QZLNSNIHXKQIIS-UHFFFAOYSA-N 4-pentoxyaniline Chemical compound CCCCCOC1=CC=C(N)C=C1 QZLNSNIHXKQIIS-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NOAADQGAIOTYSP-UHFFFAOYSA-N heptane;dihydrochloride Chemical compound Cl.Cl.CCCCCCC NOAADQGAIOTYSP-UHFFFAOYSA-N 0.000 description 4
- TWRQCVNFACGORI-UHFFFAOYSA-N hexane;dihydrochloride Chemical compound Cl.Cl.CCCCCC TWRQCVNFACGORI-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- BOTPCHFEHFGMIO-UHFFFAOYSA-N N-methyl-4-pentoxyaniline Chemical compound CCCCCOC1=CC=C(NC)C=C1 BOTPCHFEHFGMIO-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229940095076 benzaldehyde Drugs 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- KIMVTSGNCBGHES-UHFFFAOYSA-N octane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCC KIMVTSGNCBGHES-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-Bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- OCHQKGUFUAHVIV-UHFFFAOYSA-N N-methyl-2-pentoxyaniline Chemical compound CCCCCOC1=CC=CC=C1NC OCHQKGUFUAHVIV-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- ITRUYYFRYGZFBF-UHFFFAOYSA-N 1-nitro-4-pentoxybenzene Chemical compound CCCCCOC1=CC=C([N+]([O-])=O)C=C1 ITRUYYFRYGZFBF-UHFFFAOYSA-N 0.000 description 1
- BCESCHGDVIYYPC-UHFFFAOYSA-N 2-(ethylamino)phenol Chemical compound CCNC1=CC=CC=C1O BCESCHGDVIYYPC-UHFFFAOYSA-N 0.000 description 1
- HPOGUOCKUDJHBK-UHFFFAOYSA-N 2-(propylamino)phenol Chemical compound CCCNC1=CC=CC=C1O HPOGUOCKUDJHBK-UHFFFAOYSA-N 0.000 description 1
- UJWHLERCFNIFNJ-UHFFFAOYSA-N 4-(ethylamino)phenol Chemical compound CCNC1=CC=C(O)C=C1 UJWHLERCFNIFNJ-UHFFFAOYSA-N 0.000 description 1
- SKIPLXRVFOGWPD-UHFFFAOYSA-N 4-hexoxy-N-methylaniline Chemical compound CCCCCCOC1=CC=C(NC)C=C1 SKIPLXRVFOGWPD-UHFFFAOYSA-N 0.000 description 1
- FYGQPDOYMGONFR-UHFFFAOYSA-N 4-methoxy-N-(2-methylpropyl)aniline Chemical compound COC1=CC=C(NCC(C)C)C=C1 FYGQPDOYMGONFR-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- NFCXHMSCFDTGOY-UHFFFAOYSA-N C(C)NC1=CC=C(OC(CC)(CC)OC2=CC=C(C=C2)NCC)C=C1 Chemical compound C(C)NC1=CC=C(OC(CC)(CC)OC2=CC=C(C=C2)NCC)C=C1 NFCXHMSCFDTGOY-UHFFFAOYSA-N 0.000 description 1
- OCEZVOYUZFPIJF-UHFFFAOYSA-N C(C1=CC=CC=C1)C1=CC(=C(OCCCCC)C=C1)NCCC Chemical compound C(C1=CC=CC=C1)C1=CC(=C(OCCCCC)C=C1)NCCC OCEZVOYUZFPIJF-UHFFFAOYSA-N 0.000 description 1
- ZYEGOGQFMBZMGN-UHFFFAOYSA-N C(CCCC)OC1=C(N=CC2=CC=CC=C2)C=CC=C1 Chemical compound C(CCCC)OC1=C(N=CC2=CC=CC=C2)C=CC=C1 ZYEGOGQFMBZMGN-UHFFFAOYSA-N 0.000 description 1
- NSCMJBQGGOLWEW-UHFFFAOYSA-N C(CCCC)OC1=CC=C(C=C1)NCC(=O)OCC Chemical compound C(CCCC)OC1=CC=C(C=C1)NCC(=O)OCC NSCMJBQGGOLWEW-UHFFFAOYSA-N 0.000 description 1
- JEIISWJGCFWIOH-UHFFFAOYSA-N CNC1=CC=C(OC(CC)(CC)OC2=CC=C(C=C2)NC)C=C1 Chemical compound CNC1=CC=C(OC(CC)(CC)OC2=CC=C(C=C2)NC)C=C1 JEIISWJGCFWIOH-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N Ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 210000004185 Liver Anatomy 0.000 description 1
- 210000001758 Mesenteric Veins Anatomy 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000004080 Milk Anatomy 0.000 description 1
- KIKFXBHNPBRMEH-UHFFFAOYSA-N N(=O)NC1=C(C=CC(=C1)C)O Chemical compound N(=O)NC1=C(C=CC(=C1)C)O KIKFXBHNPBRMEH-UHFFFAOYSA-N 0.000 description 1
- ZQRDWUAMUJOAHJ-UHFFFAOYSA-N N-(2-pentoxyphenyl)acetamide Chemical compound CCCCCOC1=CC=CC=C1NC(C)=O ZQRDWUAMUJOAHJ-UHFFFAOYSA-N 0.000 description 1
- XADSXVABHSQCOV-UHFFFAOYSA-N N-(4-hexoxyphenyl)acetamide Chemical compound CCCCCCOC1=CC=C(NC(C)=O)C=C1 XADSXVABHSQCOV-UHFFFAOYSA-N 0.000 description 1
- OZUFCRAEDISSPP-UHFFFAOYSA-N N-(4-hydroxyphenyl)-N-methylnitrous amide Chemical compound O=NN(C)C1=CC=C(O)C=C1 OZUFCRAEDISSPP-UHFFFAOYSA-N 0.000 description 1
- BUQPVHRYORPSHH-UHFFFAOYSA-N N-(4-pentoxyphenyl)formamide Chemical compound CCCCCOC1=CC=C(NC=O)C=C1 BUQPVHRYORPSHH-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N N-Propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- QGDCKRMSVSTJKP-UHFFFAOYSA-N N-benzyl-4-pentoxyaniline Chemical compound C1=CC(OCCCCC)=CC=C1NCC1=CC=CC=C1 QGDCKRMSVSTJKP-UHFFFAOYSA-N 0.000 description 1
- QVDJNIZMXWCGQF-UHFFFAOYSA-N N-ethyl-4-hexoxyaniline Chemical compound CCCCCCOC1=CC=C(NCC)C=C1 QVDJNIZMXWCGQF-UHFFFAOYSA-N 0.000 description 1
- MCPNIYHJPMRCQU-UHFFFAOYSA-N N-ethyl-4-methoxyaniline Chemical compound CCNC1=CC=C(OC)C=C1 MCPNIYHJPMRCQU-UHFFFAOYSA-N 0.000 description 1
- AAYDNJSTPQFOLZ-UHFFFAOYSA-N N-ethyl-4-propoxyaniline Chemical compound CCCOC1=CC=C(NCC)C=C1 AAYDNJSTPQFOLZ-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N Nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 210000003240 Portal Vein Anatomy 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- VXVXRJJWYPVNLM-UHFFFAOYSA-N [2-(methylamino)phenyl] hydrogen sulfate Chemical compound CNC1=CC=CC=C1OS(O)(=O)=O VXVXRJJWYPVNLM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- SZDZEUWZYMEIGB-UHFFFAOYSA-N decane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCCCC SZDZEUWZYMEIGB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- DZVVLBSDPBGJEM-UHFFFAOYSA-N heptane;hydrate Chemical compound O.CCCCCCC DZVVLBSDPBGJEM-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- ABOWRJQOEJPPFS-UHFFFAOYSA-N nonane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCCC ABOWRJQOEJPPFS-UHFFFAOYSA-N 0.000 description 1
- SHTYJBQEEQBWSX-UHFFFAOYSA-N pentane;dihydrochloride Chemical compound Cl.Cl.CCCCC SHTYJBQEEQBWSX-UHFFFAOYSA-N 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE524653A true BE524653A (cs) |
Family
ID=159207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE524653D BE524653A (cs) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE524653A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2422625A1 (fr) * | 1977-11-25 | 1979-11-09 | Monsanto Co | Bis-alkylaminophenoxyalcanes en tant que produits antidegradants pour le caoutchouc |
-
0
- BE BE524653D patent/BE524653A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2422625A1 (fr) * | 1977-11-25 | 1979-11-09 | Monsanto Co | Bis-alkylaminophenoxyalcanes en tant que produits antidegradants pour le caoutchouc |
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