BE627205A - - Google Patents
Info
- Publication number
- BE627205A BE627205A BE627205DA BE627205A BE 627205 A BE627205 A BE 627205A BE 627205D A BE627205D A BE 627205DA BE 627205 A BE627205 A BE 627205A
- Authority
- BE
- Belgium
- Prior art keywords
- zone
- ether
- etherification
- nitrosophenol
- acid
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 264
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 150
- 238000006266 etherification reaction Methods 0.000 claims description 141
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 127
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 104
- 238000006243 chemical reaction Methods 0.000 claims description 102
- 239000000047 product Substances 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 75
- 239000002904 solvent Substances 0.000 claims description 68
- 239000011541 reaction mixture Substances 0.000 claims description 66
- -1 phenyl primary amine Chemical class 0.000 claims description 57
- 239000012071 phase Substances 0.000 claims description 54
- 150000001412 amines Chemical class 0.000 claims description 44
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 44
- 238000000926 separation method Methods 0.000 claims description 43
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 38
- 238000004821 distillation Methods 0.000 claims description 37
- 239000008346 aqueous phase Substances 0.000 claims description 28
- 230000005591 charge neutralization Effects 0.000 claims description 27
- 230000001264 neutralization Effects 0.000 claims description 27
- 238000006386 neutralization reaction Methods 0.000 claims description 27
- 239000012074 organic phase Substances 0.000 claims description 25
- 238000004064 recycling Methods 0.000 claims description 25
- 239000007921 spray Substances 0.000 claims description 25
- 239000003377 acid catalyst Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 239000011780 sodium chloride Substances 0.000 claims description 20
- OIJHFHYPXWSVPF-UHFFFAOYSA-N para-Nitrosodiphenylamine Chemical group C1=CC(N=O)=CC=C1NC1=CC=CC=C1 OIJHFHYPXWSVPF-UHFFFAOYSA-N 0.000 claims description 19
- OPULQEZIIFLBMV-UHFFFAOYSA-N 1-nitroso-4-(4-nitrosophenoxy)benzene Chemical compound C1=CC(N=O)=CC=C1OC1=CC=C(N=O)C=C1 OPULQEZIIFLBMV-UHFFFAOYSA-N 0.000 claims description 16
- 238000005507 spraying Methods 0.000 claims description 16
- 230000020477 pH reduction Effects 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000005712 crystallization Effects 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000005755 formation reaction Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 8
- 230000002829 reduced Effects 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 238000004508 fractional distillation Methods 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- SEEZWGFVHCMHJF-UHFFFAOYSA-M [O-]c1ccccc1N=O Chemical compound [O-]c1ccccc1N=O SEEZWGFVHCMHJF-UHFFFAOYSA-M 0.000 claims description 4
- 150000003333 secondary alcohols Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000075 primary alcohol group Chemical group 0.000 claims description 3
- JSTCPNFNKICNNO-UHFFFAOYSA-M 4-nitrosophenolate Chemical compound [O-]C1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-M 0.000 claims description 2
- 230000002152 alkylating Effects 0.000 claims description 2
- 230000002045 lasting Effects 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 3
- 230000003197 catalytic Effects 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 230000002441 reversible Effects 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 90
- 239000000376 reactant Substances 0.000 description 82
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 70
- 239000003054 catalyst Substances 0.000 description 57
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 44
- 229940039407 Aniline Drugs 0.000 description 41
- 239000007788 liquid Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
- 238000005576 amination reaction Methods 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 230000000875 corresponding Effects 0.000 description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 230000001476 alcoholic Effects 0.000 description 22
- 238000001914 filtration Methods 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000011084 recovery Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000007086 side reaction Methods 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 239000000470 constituent Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- 238000005292 vacuum distillation Methods 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 8
- 229940031826 phenolate Drugs 0.000 description 8
- 230000001603 reducing Effects 0.000 description 8
- MMCPOSDMTGQNKG-UHFFFAOYSA-N Anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 7
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atoms Chemical group C* 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-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
- 230000002378 acidificating Effects 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 6
- ZGWJGKWXNVDMII-UHFFFAOYSA-N 1-ethoxy-4-nitrosobenzene Chemical compound CCOC1=CC=C(N=O)C=C1 ZGWJGKWXNVDMII-UHFFFAOYSA-N 0.000 description 5
- PVFSQAKROPVPEW-UHFFFAOYSA-N O=NC1=CC=C(CCOCCC2=CC=C(C=C2)N=O)C=C1 Chemical compound O=NC1=CC=C(CCOCCC2=CC=C(C=C2)N=O)C=C1 PVFSQAKROPVPEW-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000005932 reductive alkylation reaction Methods 0.000 description 5
- RIOSDPIZGIWNMS-UHFFFAOYSA-N 1-methoxy-4-nitrosobenzene Chemical compound COC1=CC=C(N=O)C=C1 RIOSDPIZGIWNMS-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 230000003472 neutralizing Effects 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000009834 vaporization Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 235000012970 cakes Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000004682 monohydrates Chemical class 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 238000007034 nitrosation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 229960002666 1-octacosanol Drugs 0.000 description 2
- SALQMMXSINGXMI-UHFFFAOYSA-N 4-nitrosoaniline Chemical compound NC1=CC=C(N=O)C=C1 SALQMMXSINGXMI-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N Boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 240000003598 Fraxinus ornus Species 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- QQFCIHNYWMDGGE-UHFFFAOYSA-N N(=O)C1=CC=C(C=C1)COCC1=CC=C(C=C1)N=O Chemical compound N(=O)C1=CC=C(C=C1)COCC1=CC=C(C=C1)N=O QQFCIHNYWMDGGE-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N Prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 241001106462 Ulmus Species 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 230000000295 complement Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000010980 drying distillation Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical compound CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000011068 load Methods 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000001590 oxidative Effects 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic Effects 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- NAGJRPZQLWHEHH-UHFFFAOYSA-M sodium;4-nitrosophenolate Chemical compound [Na+].[O-]C1=CC=C(N=O)C=C1 NAGJRPZQLWHEHH-UHFFFAOYSA-M 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-Trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N 1,4-Butanediol, dimethanesulfonate Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-Decanol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- IRHTZOCLLONTOC-UHFFFAOYSA-N 1-Hexacosanol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 description 1
- CNNRPFQICPFDPO-UHFFFAOYSA-N 1-Octacosanol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BLMFNYXTSPNJSB-UHFFFAOYSA-N 1-chloro-4-[2-[3-(4-chlorophenyl)prop-1-en-2-ylsulfonyl]prop-2-enyl]benzene Chemical compound C1=CC(Cl)=CC=C1CC(=C)S(=O)(=O)C(=C)CC1=CC=C(Cl)C=C1 BLMFNYXTSPNJSB-UHFFFAOYSA-N 0.000 description 1
- MWAGUKZCDDRDCS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 MWAGUKZCDDRDCS-UHFFFAOYSA-N 0.000 description 1
- KPRPNESWNQSZDE-UHFFFAOYSA-N 1-nitro-4-[2-[2-(4-nitrophenyl)ethoxy]ethyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCOCCC1=CC=C([N+]([O-])=O)C=C1 KPRPNESWNQSZDE-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N 2-Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DCBCSMXGLXAXDM-UHFFFAOYSA-N 3-aminophenol;hydrochloride Chemical compound [Cl-].[NH3+]C1=CC=CC(O)=C1 DCBCSMXGLXAXDM-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
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| BE627205A true BE627205A (ja) |
Family
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Family Applications (1)
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