TWI333485B - - Google Patents
Download PDFInfo
- Publication number
- TWI333485B TWI333485B TW095105596A TW95105596A TWI333485B TW I333485 B TWI333485 B TW I333485B TW 095105596 A TW095105596 A TW 095105596A TW 95105596 A TW95105596 A TW 95105596A TW I333485 B TWI333485 B TW I333485B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- phenol
- acid
- metal oxide
- compound
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 46
- 239000000047 product Substances 0.000 claims description 45
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 41
- 238000000354 decomposition reaction Methods 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229910044991 metal oxide Inorganic materials 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 claims description 30
- 150000004706 metal oxides Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- -1 aromatic carbonyl compound Chemical class 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 claims description 2
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims 2
- 239000010955 niobium Substances 0.000 claims 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000011572 manganese Substances 0.000 claims 1
- 238000001256 steam distillation Methods 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- 239000013589 supplement Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000010025 steaming Methods 0.000 description 5
- LENBTPHYHQHCSR-UHFFFAOYSA-N 1-phenylethenethiol Chemical compound SC(=C)C1=CC=CC=C1 LENBTPHYHQHCSR-UHFFFAOYSA-N 0.000 description 4
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
- 235000010234 sodium benzoate Nutrition 0.000 description 4
- 239000004299 sodium benzoate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 206010036790 Productive cough Diseases 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 210000003802 sputum Anatomy 0.000 description 3
- 208000024794 sputum Diseases 0.000 description 3
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910000410 antimony oxide Inorganic materials 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- UFRQQBZAYHXOKS-UHFFFAOYSA-N cumene;phenol Chemical compound OC1=CC=CC=C1.CC(C)C1=CC=CC=C1 UFRQQBZAYHXOKS-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- GEYXPJBPASPPLI-UHFFFAOYSA-N manganese(iii) oxide Chemical compound O=[Mn]O[Mn]=O GEYXPJBPASPPLI-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 2
- VASIZKWUTCETSD-UHFFFAOYSA-N oxomanganese Chemical compound [Mn]=O VASIZKWUTCETSD-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- 239000004291 sulphur dioxide Substances 0.000 description 2
- WAPNOHKVXSQRPX-SSDOTTSWSA-N (R)-1-phenylethanol Chemical compound C[C@@H](O)C1=CC=CC=C1 WAPNOHKVXSQRPX-SSDOTTSWSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- ZNZJQJLLXWDANB-UHFFFAOYSA-N 1-benzofuran-2-thiol Chemical compound C1=CC=C2OC(S)=CC2=C1 ZNZJQJLLXWDANB-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- SGJUFIMCHSLMRJ-UHFFFAOYSA-N 2-hydroperoxypropane Chemical group CC(C)OO SGJUFIMCHSLMRJ-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
- BPUBMURFUMRSSA-UHFFFAOYSA-N 4-(3-methylbutyl)cyclohexan-1-one Chemical compound CC(C)CCC1CCC(=O)CC1 BPUBMURFUMRSSA-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- HRGJOARRRQBPHM-UHFFFAOYSA-N C12C(C=CC=C1)O2.[Na] Chemical compound C12C(C=CC=C1)O2.[Na] HRGJOARRRQBPHM-UHFFFAOYSA-N 0.000 description 1
- BEKDQHZAFVNOLG-UHFFFAOYSA-N ClOOCl.C1(=CC=CC=C1)C(C)C Chemical compound ClOOCl.C1(=CC=CC=C1)C(C)C BEKDQHZAFVNOLG-UHFFFAOYSA-N 0.000 description 1
- 244000163122 Curcuma domestica Species 0.000 description 1
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000061 acid fraction Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- KLWWVZYLMNXWLI-UHFFFAOYSA-N benzene cumene Chemical compound C1=CC=CC=C1.C1(=CC=CC=C1)C(C)C.C1=CC=CC=C1 KLWWVZYLMNXWLI-UHFFFAOYSA-N 0.000 description 1
- MLFRJNDWWVGFKR-UHFFFAOYSA-N benzene;cumene Chemical compound C1=CC=CC=C1.CC(C)C1=CC=CC=C1 MLFRJNDWWVGFKR-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- VJYHZDGQCJNYKG-UHFFFAOYSA-N bis(sulfanyl)methanol Chemical compound OC(S)S VJYHZDGQCJNYKG-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000003373 curcuma longa Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- KVIPHDKUOLVVQN-UHFFFAOYSA-N ethene;hydrate Chemical compound O.C=C KVIPHDKUOLVVQN-UHFFFAOYSA-N 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 1
- VAGZBIIFQQBXOU-UHFFFAOYSA-N manganese(2+) oxygen(2-) Chemical compound [O--].[O--].[O--].[Mn++].[Mn++].[Mn++] VAGZBIIFQQBXOU-UHFFFAOYSA-N 0.000 description 1
- KVGMATYUUPJFQL-UHFFFAOYSA-N manganese(2+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Mn++].[Mn++].[Mn++] KVGMATYUUPJFQL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- WHFPBRFQBDIHDA-UHFFFAOYSA-N styrene;thiophene Chemical compound C=1C=CSC=1.C=CC1=CC=CC=C1 WHFPBRFQBDIHDA-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C37/76—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation by steam distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C37/80—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005043986 | 2005-02-21 | ||
| JP2005305478 | 2005-10-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200640844A TW200640844A (en) | 2006-12-01 |
| TWI333485B true TWI333485B (enrdf_load_stackoverflow) | 2010-11-21 |
Family
ID=36916351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095105596A TW200640844A (en) | 2005-02-21 | 2006-02-20 | Methods of purifying phenol compound |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4949226B2 (enrdf_load_stackoverflow) |
| CN (1) | CN101128411B (enrdf_load_stackoverflow) |
| TW (1) | TW200640844A (enrdf_load_stackoverflow) |
| WO (1) | WO2006087943A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI549936B (zh) * | 2012-04-13 | 2016-09-21 | 三井化學股份有限公司 | 酚之精製方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6294798B2 (ja) * | 2014-09-17 | 2018-03-14 | 三井化学株式会社 | 粗フェノール中のヒドロキシアセトンを低減させる方法、ヒドロキシアセトンが少ない粗フェノールの製造方法および高純度フェノールの製造方法 |
| KR102011715B1 (ko) * | 2015-10-22 | 2019-08-19 | 주식회사 엘지화학 | 페놀 정제 방법 |
| CN106810424A (zh) * | 2017-02-16 | 2017-06-09 | 重庆西南制药二厂有限责任公司 | 一种医药级苯酚的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1183331B (it) * | 1985-02-08 | 1987-10-22 | Anic Spa | Procedimento per la purificazione di fenolo |
| JP2543074B2 (ja) * | 1987-04-09 | 1996-10-16 | 三井石油化学工業株式会社 | フェノ−ル蒸留残渣からの有用物質の回収方法 |
| JPS63252547A (ja) * | 1987-04-09 | 1988-10-19 | Mitsui Petrochem Ind Ltd | フエノ−ル蒸留残渣分解用触媒 |
| DE3863958D1 (de) * | 1987-04-09 | 1991-09-05 | Mitsui Petrochemical Ind | Katalysatoren fuer die katalytische pyrolyse von phenoldestillationsrueckstaenden und verfahren fuer die wiedergewinnung der nuetzlichen stoffe durch die pyrolyse derselben. |
| JPH05286879A (ja) * | 1992-04-03 | 1993-11-02 | Mitsui Petrochem Ind Ltd | 高純度フェノールの製造方法 |
| RU2111203C1 (ru) * | 1993-12-01 | 1998-05-20 | Закошанский Владимир Михайлович | Способ очистки фенола от органических примесей |
| JP3948845B2 (ja) * | 1998-12-09 | 2007-07-25 | 三井化学株式会社 | 粗フェノール液の処理方法 |
-
2006
- 2006-02-07 JP JP2007503621A patent/JP4949226B2/ja active Active
- 2006-02-07 CN CN2006800056000A patent/CN101128411B/zh not_active Expired - Fee Related
- 2006-02-07 WO PCT/JP2006/302083 patent/WO2006087943A1/ja not_active Application Discontinuation
- 2006-02-20 TW TW095105596A patent/TW200640844A/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI549936B (zh) * | 2012-04-13 | 2016-09-21 | 三井化學股份有限公司 | 酚之精製方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4949226B2 (ja) | 2012-06-06 |
| JPWO2006087943A1 (ja) | 2008-07-03 |
| WO2006087943A1 (ja) | 2006-08-24 |
| CN101128411A (zh) | 2008-02-20 |
| TW200640844A (en) | 2006-12-01 |
| CN101128411B (zh) | 2010-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE1000439A3 (fr) | Procede et catalyseur perfectionnes pour l'hydrogenation d'aldehydes. | |
| JP5470277B2 (ja) | アルコールの酸化的脱水素化によるオレフィン系不飽和カルボニル化合物の製造方法 | |
| TWI333485B (enrdf_load_stackoverflow) | ||
| Vocanson et al. | Dioxygen oxidation of alcohols and aldehydes over a cerium dioxide-ruthenium system | |
| Das et al. | Transition metal-and photoredox-catalyzed valorisation of lignin subunits | |
| CN101479226B (zh) | 制备环酮的方法 | |
| FR2660651A1 (fr) | Procede d'obtention d'au moins une olefine tertiaire par decomposition de l'ether correspondant. | |
| Llopis et al. | Oxidation of electron-rich arenes using HFIP-UHP system | |
| EP3628655B1 (en) | Method for decomposing byproduct of phenol production process | |
| JP2021510727A (ja) | グリセリン製アリルアルコールのヒドロホルミル化によるｂｄｏの製造 | |
| Kleoff et al. | Synthesis of odorants in flow and their applications in perfumery | |
| CS277195B6 (en) | Cyclohexanol and/or cyclohexanone production method | |
| CN102336694A (zh) | 双(叔丁基过氧基)缩酮的合成方法 | |
| CS220799B2 (en) | Method of preparation of the cyclohexanole or cyclohexanone | |
| JP2004508345A (ja) | フッ化および塩化ベンズアルデヒドの製造方法およびそれによって得られるフッ化および塩化ベンズアルデヒドを含有する組成物 | |
| WO2002026680A1 (en) | Hydrogenation of cleavage effluents in phenol production | |
| Letsinger et al. | The Reactions of Some Organometallic Compounds with Cyclohexene Oxide1 | |
| Akamanchi et al. | Diisopropoxyaluminium trifluoroacetate/4-nitrobenzaldehyde—a new oppenauer oxidation system for accelerated oxidation of secondary alcohols to the corresponding ketones | |
| RU2568645C1 (ru) | Способ получения замещенных хинонов | |
| Dapurkar et al. | Highly selective oxidation of tetralin to 1-tetralone over mesoporous CrMCM-41 molecular sieve catalyst using supercritical carbon dioxide | |
| US3987101A (en) | Process for preparing cycloalkanones and cycloalkanols | |
| El Amrani et al. | Efficient and selective oxidation of aldehydes with dioxygen catalysed by vanadium-containing heteropolyanions | |
| EP1440050B1 (fr) | Procede de decomposition catalytique des hydroperoxydes organiques | |
| TW201134801A (en) | Process for the production of an alkyl hydroperoxide | |
| US20100256421A1 (en) | Propanal Production Methods |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |