SG192423A1 - Process for preparing diaryl carbonates from dialkyl carbonates - Google Patents
Process for preparing diaryl carbonates from dialkyl carbonates Download PDFInfo
- Publication number
- SG192423A1 SG192423A1 SG2013048012A SG2013048012A SG192423A1 SG 192423 A1 SG192423 A1 SG 192423A1 SG 2013048012 A SG2013048012 A SG 2013048012A SG 2013048012 A SG2013048012 A SG 2013048012A SG 192423 A1 SG192423 A1 SG 192423A1
- Authority
- SG
- Singapore
- Prior art keywords
- column
- reaction
- carbonate
- condensation
- condenser
- Prior art date
Links
- -1 diaryl carbonates Chemical class 0.000 title claims abstract description 365
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 150000004649 carbonic acid derivatives Chemical class 0.000 title abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 504
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 223
- 238000000034 method Methods 0.000 claims abstract description 218
- 230000008569 process Effects 0.000 claims abstract description 167
- 238000009835 boiling Methods 0.000 claims abstract description 84
- 238000002360 preparation method Methods 0.000 claims abstract description 29
- 238000000746 purification Methods 0.000 claims abstract description 26
- 239000006227 byproduct Substances 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims description 207
- 238000009833 condensation Methods 0.000 claims description 139
- 230000005494 condensation Effects 0.000 claims description 139
- 239000000047 product Substances 0.000 claims description 93
- 239000003054 catalyst Substances 0.000 claims description 43
- 238000005809 transesterification reaction Methods 0.000 claims description 37
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000012535 impurity Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 97
- 239000000543 intermediate Substances 0.000 description 121
- 239000000203 mixture Substances 0.000 description 86
- 239000007788 liquid Substances 0.000 description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 238000010992 reflux Methods 0.000 description 48
- 229930000044 secondary metabolite Natural products 0.000 description 40
- 238000000926 separation method Methods 0.000 description 39
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 38
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 35
- 238000001704 evaporation Methods 0.000 description 28
- 230000008020 evaporation Effects 0.000 description 27
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 25
- 238000012856 packing Methods 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 19
- 238000010626 work up procedure Methods 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 17
- 239000012528 membrane Substances 0.000 description 14
- 239000000376 reactant Substances 0.000 description 13
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 12
- 230000010354 integration Effects 0.000 description 11
- 239000012466 permeate Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000007323 disproportionation reaction Methods 0.000 description 10
- XTBFPVLHGVYOQH-UHFFFAOYSA-N methyl phenyl carbonate Chemical compound COC(=O)OC1=CC=CC=C1 XTBFPVLHGVYOQH-UHFFFAOYSA-N 0.000 description 10
- 239000012465 retentate Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000013461 design Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 230000001174 ascending effect Effects 0.000 description 6
- 150000002736 metal compounds Chemical class 0.000 description 6
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 6
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 6
- 238000005373 pervaporation Methods 0.000 description 5
- 238000004094 preconcentration Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000005587 carbonate group Chemical group 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- 239000002918 waste heat Substances 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 3
- 229960000969 phenyl salicylate Drugs 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229960001860 salicylate Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- MHFGNKMUCULCRW-UHFFFAOYSA-N bis(4-phenylphenyl) carbonate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OC(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 MHFGNKMUCULCRW-UHFFFAOYSA-N 0.000 description 2
- WMEZDESZXBGWCU-UHFFFAOYSA-N bis(4-tert-butylphenyl) carbonate Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(=O)OC1=CC=C(C(C)(C)C)C=C1 WMEZDESZXBGWCU-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 235000020030 perry Nutrition 0.000 description 2
- XYBIRSPHZKSOJB-UHFFFAOYSA-N phenyl [4-(2-phenylpropan-2-yl)phenyl] carbonate Chemical compound C=1C=C(OC(=O)OC=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 XYBIRSPHZKSOJB-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- VNZHRDGEQMGDEZ-UHFFFAOYSA-N (2,3-dimethylphenyl) phenyl carbonate Chemical class CC1=CC=CC(OC(=O)OC=2C=CC=CC=2)=C1C VNZHRDGEQMGDEZ-UHFFFAOYSA-N 0.000 description 1
- RHAHBJPEAVBNMC-UHFFFAOYSA-N (2-methylphenyl) phenyl carbonate Chemical class CC1=CC=CC=C1OC(=O)OC1=CC=CC=C1 RHAHBJPEAVBNMC-UHFFFAOYSA-N 0.000 description 1
- MXTIGIDKHNHSED-UHFFFAOYSA-N (3-pentadecylphenyl) phenyl carbonate Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(OC(=O)OC=2C=CC=CC=2)=C1 MXTIGIDKHNHSED-UHFFFAOYSA-N 0.000 description 1
- HTZJDCCKHCMKHB-UHFFFAOYSA-N (4-butylphenyl) phenyl carbonate Chemical compound C1=CC(CCCC)=CC=C1OC(=O)OC1=CC=CC=C1 HTZJDCCKHCMKHB-UHFFFAOYSA-N 0.000 description 1
- YVZRSAKDPDOUPK-UHFFFAOYSA-N (4-chlorophenyl) ethyl carbonate Chemical compound CCOC(=O)OC1=CC=C(Cl)C=C1 YVZRSAKDPDOUPK-UHFFFAOYSA-N 0.000 description 1
- BDEKOUFEKGUQNV-UHFFFAOYSA-N (4-cyclohexylphenyl) phenyl carbonate Chemical compound C=1C=C(C2CCCCC2)C=CC=1OC(=O)OC1=CC=CC=C1 BDEKOUFEKGUQNV-UHFFFAOYSA-N 0.000 description 1
- KQWWPFLBEQBEFN-UHFFFAOYSA-N (4-ethylphenyl) phenyl carbonate Chemical compound C1=CC(CC)=CC=C1OC(=O)OC1=CC=CC=C1 KQWWPFLBEQBEFN-UHFFFAOYSA-N 0.000 description 1
- ASEOUYVSVADLDF-UHFFFAOYSA-N (4-hexylphenyl) phenyl carbonate Chemical compound C1=CC(CCCCCC)=CC=C1OC(=O)OC1=CC=CC=C1 ASEOUYVSVADLDF-UHFFFAOYSA-N 0.000 description 1
- CFVDTINNSVGGFC-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl) phenyl carbonate Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1OC(=O)OC1=CC=CC=C1 CFVDTINNSVGGFC-UHFFFAOYSA-N 0.000 description 1
- SNRIJTKVARYJOU-UHFFFAOYSA-N (4-naphthalen-2-ylphenyl) phenyl carbonate Chemical compound C=1C=C(C=2C=C3C=CC=CC3=CC=2)C=CC=1OC(=O)OC1=CC=CC=C1 SNRIJTKVARYJOU-UHFFFAOYSA-N 0.000 description 1
- DMHGSUYGDDZSAC-UHFFFAOYSA-N (4-nonylphenyl) phenyl carbonate Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC(=O)OC1=CC=CC=C1 DMHGSUYGDDZSAC-UHFFFAOYSA-N 0.000 description 1
- WNHXMQFSRNROAJ-UHFFFAOYSA-N (4-phenoxyphenyl) phenyl carbonate Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OC(=O)OC1=CC=CC=C1 WNHXMQFSRNROAJ-UHFFFAOYSA-N 0.000 description 1
- AYVUVANBHSZJDU-UHFFFAOYSA-N (4-tert-butylphenyl) phenyl carbonate Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(=O)OC1=CC=CC=C1 AYVUVANBHSZJDU-UHFFFAOYSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- SUSANQWSCSKXPF-UHFFFAOYSA-N 2-(2-methylpropoxy)benzoic acid Chemical compound CC(C)COC1=CC=CC=C1C(O)=O SUSANQWSCSKXPF-UHFFFAOYSA-N 0.000 description 1
- MHQOYFOLCFUDCH-UHFFFAOYSA-N 2-(2-methylpropoxy)benzoic acid;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.CC(C)COC1=CC=CC=C1C(O)=O MHQOYFOLCFUDCH-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- MQFDMZNZEHTLND-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]benzoic acid Chemical compound CC(C)(C)OC1=CC=CC=C1C(O)=O MQFDMZNZEHTLND-UHFFFAOYSA-N 0.000 description 1
- JOHLKFUFRHLGQD-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]benzoic acid;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.CC(C)(C)OC1=CC=CC=C1C(O)=O JOHLKFUFRHLGQD-UHFFFAOYSA-N 0.000 description 1
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- RDLBRIMYNHHTSE-UHFFFAOYSA-N 2-butoxybenzoic acid;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.CCCCOC1=CC=CC=C1C(O)=O RDLBRIMYNHHTSE-UHFFFAOYSA-N 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- OLMQAFUQSHSVLF-UHFFFAOYSA-N 2-ethoxybenzoic acid;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.CCOC1=CC=CC=C1C(O)=O OLMQAFUQSHSVLF-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- DVLQAYXHSPHFLF-UHFFFAOYSA-N 2-methoxybenzoic acid;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.COC1=CC=CC=C1C(O)=O DVLQAYXHSPHFLF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- GMOYUTKNPLBTMT-UHFFFAOYSA-N 2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 GMOYUTKNPLBTMT-UHFFFAOYSA-N 0.000 description 1
- WWPLDSOFBMZGIJ-UHFFFAOYSA-N 2-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=CC=C1C(O)=O WWPLDSOFBMZGIJ-UHFFFAOYSA-N 0.000 description 1
- OXOWWPXTTOCKKU-UHFFFAOYSA-N 2-propoxybenzoic acid Chemical compound CCCOC1=CC=CC=C1C(O)=O OXOWWPXTTOCKKU-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- MPWGZBWDLMDIHO-UHFFFAOYSA-N 3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1 MPWGZBWDLMDIHO-UHFFFAOYSA-N 0.000 description 1
- GDEHXPCZWFXRKC-UHFFFAOYSA-N 4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C=C1 GDEHXPCZWFXRKC-UHFFFAOYSA-N 0.000 description 1
- HVXRCAWUNAOCTA-UHFFFAOYSA-N 4-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=C(O)C=C1 HVXRCAWUNAOCTA-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- SZWBRVPZWJYIHI-UHFFFAOYSA-N 4-n-Hexylphenol Chemical compound CCCCCCC1=CC=C(O)C=C1 SZWBRVPZWJYIHI-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- UEULEVKFYSYUCZ-UHFFFAOYSA-N 4-naphthalen-1-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CC2=CC=CC=C12 UEULEVKFYSYUCZ-UHFFFAOYSA-N 0.000 description 1
- NIRHUNSXEDESLN-UHFFFAOYSA-N 4-naphthalen-2-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(C=CC=C2)C2=C1 NIRHUNSXEDESLN-UHFFFAOYSA-N 0.000 description 1
- NIPKXTKKYSKEON-UHFFFAOYSA-N 4-tritylphenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NIPKXTKKYSKEON-UHFFFAOYSA-N 0.000 description 1
- HCJMNOSIAGSZBM-UHFFFAOYSA-N 6-methylsalicylic acid Chemical compound CC1=CC=CC(O)=C1C(O)=O HCJMNOSIAGSZBM-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YFDUWSBGVPBWKF-UHFFFAOYSA-N Butyl salicylate Chemical compound CCCCOC(=O)C1=CC=CC=C1O YFDUWSBGVPBWKF-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910020282 Pb(OH) Inorganic materials 0.000 description 1
- 229910020997 Sn-Y Inorganic materials 0.000 description 1
- 229910008859 Sn—Y Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JIJHEVYJIGWWCN-UHFFFAOYSA-L [(2-hydroxyacetyl)oxy-dimethylstannyl] 2-hydroxyacetate Chemical compound C[Sn+2]C.OCC([O-])=O.OCC([O-])=O JIJHEVYJIGWWCN-UHFFFAOYSA-L 0.000 description 1
- GQILWUUWAFPMPA-UHFFFAOYSA-N [4-(2-methylpropyl)phenyl] phenyl carbonate Chemical compound C1=CC(CC(C)C)=CC=C1OC(=O)OC1=CC=CC=C1 GQILWUUWAFPMPA-UHFFFAOYSA-N 0.000 description 1
- CYBNQCAJBVJTJS-UHFFFAOYSA-N [4-(6-methylheptyl)phenyl] phenyl carbonate Chemical compound C1=CC(CCCCCC(C)C)=CC=C1OC(=O)OC1=CC=CC=C1 CYBNQCAJBVJTJS-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- RHATVZBALBUXBY-UHFFFAOYSA-N bis(2,3-dimethylphenyl) carbonate Chemical class CC1=CC=CC(OC(=O)OC=2C(=C(C)C=CC=2)C)=C1C RHATVZBALBUXBY-UHFFFAOYSA-N 0.000 description 1
- DPGAUDBZWZEOJV-UHFFFAOYSA-N bis(3-pentadecylphenyl) carbonate Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(OC(=O)OC=2C=C(CCCCCCCCCCCCCCC)C=CC=2)=C1 DPGAUDBZWZEOJV-UHFFFAOYSA-N 0.000 description 1
- LZZKLIBVSKXSCF-UHFFFAOYSA-N bis(4-cyclohexylphenyl) carbonate Chemical compound C=1C=C(C2CCCCC2)C=CC=1OC(=O)OC(C=C1)=CC=C1C1CCCCC1 LZZKLIBVSKXSCF-UHFFFAOYSA-N 0.000 description 1
- HZCHHQPBFVITLD-UHFFFAOYSA-N bis(4-ethylphenyl) carbonate Chemical compound C1=CC(CC)=CC=C1OC(=O)OC1=CC=C(CC)C=C1 HZCHHQPBFVITLD-UHFFFAOYSA-N 0.000 description 1
- CTZHJMXWJVRWOI-UHFFFAOYSA-N bis(4-hexylphenyl) carbonate Chemical compound C1=CC(CCCCCC)=CC=C1OC(=O)OC1=CC=C(CCCCCC)C=C1 CTZHJMXWJVRWOI-UHFFFAOYSA-N 0.000 description 1
- MRPCLYWGRZLSOE-UHFFFAOYSA-N bis(4-nonylphenyl) carbonate Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC(=O)OC1=CC=C(CCCCCCCCC)C=C1 MRPCLYWGRZLSOE-UHFFFAOYSA-N 0.000 description 1
- JNJOFABSCAHZGH-UHFFFAOYSA-N bis(4-pentylphenyl) carbonate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)OC1=CC=C(CCCCC)C=C1 JNJOFABSCAHZGH-UHFFFAOYSA-N 0.000 description 1
- LGSACZFATCFFPF-UHFFFAOYSA-N bis(4-phenoxyphenyl) carbonate Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OC(=O)OC(C=C1)=CC=C1OC1=CC=CC=C1 LGSACZFATCFFPF-UHFFFAOYSA-N 0.000 description 1
- FAMYXRBOUQOMGA-UHFFFAOYSA-N bis(4-propan-2-ylphenyl) carbonate Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)OC1=CC=C(C(C)C)C=C1 FAMYXRBOUQOMGA-UHFFFAOYSA-N 0.000 description 1
- FTIFDVZEGMYEDJ-UHFFFAOYSA-N bis(4-propylphenyl) carbonate Chemical compound C1=CC(CCC)=CC=C1OC(=O)OC1=CC=C(CCC)C=C1 FTIFDVZEGMYEDJ-UHFFFAOYSA-N 0.000 description 1
- YASPVARLBMZYDN-UHFFFAOYSA-N bis(4-tritylphenyl) carbonate Chemical compound C=1C=C(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1OC(=O)OC(C=C1)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YASPVARLBMZYDN-UHFFFAOYSA-N 0.000 description 1
- HHIKOVJJAYAYAV-UHFFFAOYSA-N bis[4-(2-methylpropyl)phenyl] carbonate Chemical compound C1=CC(CC(C)C)=CC=C1OC(=O)OC1=CC=C(CC(C)C)C=C1 HHIKOVJJAYAYAV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CMIUEWSUNAYXCG-UHFFFAOYSA-N butyl phenyl carbonate Chemical compound CCCCOC(=O)OC1=CC=CC=C1 CMIUEWSUNAYXCG-UHFFFAOYSA-N 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- ZOSNUSDWUQRFEV-UHFFFAOYSA-N carbonic acid;2-(2-methylpropoxy)benzoic acid Chemical compound OC(O)=O.CC(C)COC1=CC=CC=C1C(O)=O.CC(C)COC1=CC=CC=C1C(O)=O ZOSNUSDWUQRFEV-UHFFFAOYSA-N 0.000 description 1
- GEORAFUSHYWVNC-UHFFFAOYSA-N carbonic acid;2-[(2-methylpropan-2-yl)oxy]benzoic acid Chemical compound OC(O)=O.CC(C)(C)OC1=CC=CC=C1C(O)=O.CC(C)(C)OC1=CC=CC=C1C(O)=O GEORAFUSHYWVNC-UHFFFAOYSA-N 0.000 description 1
- GYDIUBRZHJFDFW-UHFFFAOYSA-N carbonic acid;2-ethoxybenzoic acid Chemical compound OC(O)=O.CCOC1=CC=CC=C1C(O)=O.CCOC1=CC=CC=C1C(O)=O GYDIUBRZHJFDFW-UHFFFAOYSA-N 0.000 description 1
- NUIUCBXCQAURNX-UHFFFAOYSA-N carbonic acid;2-phenoxybenzoic acid Chemical compound OC(O)=O.OC(=O)C1=CC=CC=C1OC1=CC=CC=C1.OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 NUIUCBXCQAURNX-UHFFFAOYSA-N 0.000 description 1
- ITTYRUSZRZUFKR-UHFFFAOYSA-N carbonic acid;2-phenylmethoxybenzoic acid Chemical compound OC(O)=O.OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1.OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 ITTYRUSZRZUFKR-UHFFFAOYSA-N 0.000 description 1
- FTOFKHIXIUBMPI-UHFFFAOYSA-N carbonic acid;2-propoxybenzoic acid Chemical compound OC(O)=O.CCCOC1=CC=CC=C1C(O)=O.CCCOC1=CC=CC=C1C(O)=O FTOFKHIXIUBMPI-UHFFFAOYSA-N 0.000 description 1
- LVENVGUTWJYGIK-UHFFFAOYSA-N carbonic acid;phenol Chemical compound OC(O)=O.OC1=CC=CC=C1 LVENVGUTWJYGIK-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- RYRWDTRXCNOMOJ-UHFFFAOYSA-N dibutan-2-yl carbonate Chemical compound CCC(C)OC(=O)OC(C)CC RYRWDTRXCNOMOJ-UHFFFAOYSA-N 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- SGIBEPSSERDAHS-UHFFFAOYSA-L dibutyltin(2+);hexanedioate Chemical compound CCCC[Sn+2]CCCC.[O-]C(=O)CCCCC([O-])=O SGIBEPSSERDAHS-UHFFFAOYSA-L 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- OKQDSOXFNBWWJL-UHFFFAOYSA-N dihexyl carbonate Chemical compound CCCCCCOC(=O)OCCCCCC OKQDSOXFNBWWJL-UHFFFAOYSA-N 0.000 description 1
- ZQUZPFYNEARCQO-UHFFFAOYSA-N dinaphthalen-1-yl carbonate Chemical compound C1=CC=C2C(OC(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ZQUZPFYNEARCQO-UHFFFAOYSA-N 0.000 description 1
- VJJMAHPIEWRZKY-UHFFFAOYSA-N dinaphthalen-2-yl carbonate Chemical compound C1=CC=CC2=CC(OC(OC=3C=C4C=CC=CC4=CC=3)=O)=CC=C21 VJJMAHPIEWRZKY-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- JMPVESVJOFYWTB-UHFFFAOYSA-N dipropan-2-yl carbonate Chemical compound CC(C)OC(=O)OC(C)C JMPVESVJOFYWTB-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JLZDLAVNHPSNOP-UHFFFAOYSA-N ethyl (2-methylphenyl) carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1C JLZDLAVNHPSNOP-UHFFFAOYSA-N 0.000 description 1
- SMZZUTOGLVAUKB-UHFFFAOYSA-N ethyl (4-methylphenyl) carbonate Chemical compound CCOC(=O)OC1=CC=C(C)C=C1 SMZZUTOGLVAUKB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- LNLXSADGXCRMIV-UHFFFAOYSA-N hexyl phenyl carbonate Chemical compound CCCCCCOC(=O)OC1=CC=CC=C1 LNLXSADGXCRMIV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LNOZJRCUHSPCDZ-UHFFFAOYSA-L iron(ii) acetate Chemical compound [Fe+2].CC([O-])=O.CC([O-])=O LNOZJRCUHSPCDZ-UHFFFAOYSA-L 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- LKPHHVAUQVDDPF-UHFFFAOYSA-N methyl (2-methylphenyl) carbonate Chemical compound COC(=O)OC1=CC=CC=C1C LKPHHVAUQVDDPF-UHFFFAOYSA-N 0.000 description 1
- FLSOKBQNISCLMI-UHFFFAOYSA-N methyl (4-methylphenyl) carbonate Chemical compound COC(=O)OC1=CC=C(C)C=C1 FLSOKBQNISCLMI-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YPURHVDOFHBPQV-UHFFFAOYSA-N naphthalen-1-yl phenyl carbonate Chemical compound C=1C=CC2=CC=CC=C2C=1OC(=O)OC1=CC=CC=C1 YPURHVDOFHBPQV-UHFFFAOYSA-N 0.000 description 1
- XYAKPBSZQDLKLE-UHFFFAOYSA-N naphthalen-2-yl phenyl carbonate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=O)OC1=CC=CC=C1 XYAKPBSZQDLKLE-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- DBLKSQITUIDPOE-UHFFFAOYSA-N phenyl (4-phenylphenyl) carbonate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OC(=O)OC1=CC=CC=C1 DBLKSQITUIDPOE-UHFFFAOYSA-N 0.000 description 1
- GKRAYAFHQZLFKC-UHFFFAOYSA-N phenyl (4-propan-2-ylphenyl) carbonate Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)OC1=CC=CC=C1 GKRAYAFHQZLFKC-UHFFFAOYSA-N 0.000 description 1
- KVEVLMQLOIVHJO-UHFFFAOYSA-N phenyl (4-propylphenyl) carbonate Chemical compound C1=CC(CCC)=CC=C1OC(=O)OC1=CC=CC=C1 KVEVLMQLOIVHJO-UHFFFAOYSA-N 0.000 description 1
- WKIQBUSKRIINCP-UHFFFAOYSA-N phenyl (4-tritylphenyl) carbonate Chemical compound C=1C=C(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1OC(=O)OC1=CC=CC=C1 WKIQBUSKRIINCP-UHFFFAOYSA-N 0.000 description 1
- JKRYMCASRVELRG-UHFFFAOYSA-N phenyl hydrogen carbonate;2-propoxybenzoic acid Chemical compound OC(=O)OC1=CC=CC=C1.CCCOC1=CC=CC=C1C(O)=O JKRYMCASRVELRG-UHFFFAOYSA-N 0.000 description 1
- UXLOWURRLHBLIK-UHFFFAOYSA-N phenyl propyl carbonate Chemical compound CCCOC(=O)OC1=CC=CC=C1 UXLOWURRLHBLIK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052572 stoneware Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- KYFSRNRVSILODI-UHFFFAOYSA-M triethylstannyl benzoate Chemical compound CC[Sn+](CC)CC.[O-]C(=O)C1=CC=CC=C1 KYFSRNRVSILODI-UHFFFAOYSA-M 0.000 description 1
- OLBXOAKEHMWSOV-UHFFFAOYSA-N triethyltin;hydrate Chemical compound O.CC[Sn](CC)CC OLBXOAKEHMWSOV-UHFFFAOYSA-N 0.000 description 1
- XZVPFLCTEMAYFI-UHFFFAOYSA-M trimethylstannyl acetate Chemical compound CC(=O)O[Sn](C)(C)C XZVPFLCTEMAYFI-UHFFFAOYSA-M 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008029514A DE102008029514A1 (de) | 2008-06-21 | 2008-06-21 | Verfahren zur Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG192423A1 true SG192423A1 (en) | 2013-08-30 |
Family
ID=41151820
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2013048012A SG192423A1 (en) | 2008-06-21 | 2009-06-19 | Process for preparing diaryl carbonates from dialkyl carbonates |
| SG200904220-1A SG158046A1 (en) | 2008-06-21 | 2009-06-19 | Process for preparing diaryl carbonates from dialkyl carbonates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG200904220-1A SG158046A1 (en) | 2008-06-21 | 2009-06-19 | Process for preparing diaryl carbonates from dialkyl carbonates |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9040732B2 (https=) |
| EP (1) | EP2135857B1 (https=) |
| JP (1) | JP5596307B2 (https=) |
| KR (1) | KR101651673B1 (https=) |
| CN (1) | CN101607908B (https=) |
| DE (1) | DE102008029514A1 (https=) |
| ES (1) | ES2540226T3 (https=) |
| RU (1) | RU2515993C2 (https=) |
| SG (2) | SG192423A1 (https=) |
| TW (1) | TWI455923B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009053370A1 (de) * | 2009-11-14 | 2011-05-19 | Bayer Materialscience Ag | Verfahren zur Reinigung von Dialkylcarbonaten |
| EP2507201B1 (en) * | 2009-12-04 | 2018-05-30 | Shell International Research Maatschappij B.V. | Process for preparing diaryl carbonates |
| DE102010006657A1 (de) * | 2010-02-03 | 2011-08-04 | Bayer MaterialScience AG, 51373 | Verfahren zur Herstellung von Dialkylcarbonaten |
| WO2012076532A1 (en) * | 2010-12-08 | 2012-06-14 | Shell Internationale Research Maatschappij B.V. | Process for purifying aryl group containing carbonates |
| EP2679573B1 (en) * | 2012-06-29 | 2017-12-27 | SABIC Global Technologies B.V. | Method and apparatus for the separation of dialkyl carbonate, water and alkanol |
| EP2679572B1 (en) * | 2012-06-29 | 2017-12-13 | SABIC Global Technologies B.V. | Method and apparatus for the production of diaryl carbonate |
| US9895624B2 (en) | 2013-07-18 | 2018-02-20 | Lg Chem, Ltd. | Distillation device |
| US9458022B2 (en) * | 2014-03-28 | 2016-10-04 | L'Air Liquide Société Anonyme Pour L'Étude Et L'Exploitation Des Procedes Georges Claude | Process and apparatus for separating NO2 from a CO2 and NO2—containing fluid |
| SG11201803481PA (en) | 2015-11-26 | 2018-06-28 | Shell Int Research | Process for preparing a diaryl carbonate |
| DE102016116078B3 (de) * | 2016-08-29 | 2018-01-04 | Epc Engineering Consulting Gmbh | Verfahren zur Herstellung eines Polycarbonats unter Einsatz einer Strippvorrichtung |
| CN113577814B (zh) * | 2021-08-16 | 2022-10-18 | 四川中蓝国塑新材料科技有限公司 | 一种用于聚碳酸酯工业化生产的碳酸二苯酯回收装置及方法 |
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| US3803201A (en) | 1971-02-22 | 1974-04-09 | Dow Chemical Co | Synthesis of dimethyl carbonate |
| DE2736062A1 (de) | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
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| DE2740243A1 (de) | 1977-09-07 | 1979-03-15 | Bayer Ag | Verfahren zur herstellung von dialkylcarbonaten |
| JPS5463023A (en) | 1977-10-26 | 1979-05-21 | Mitsubishi Chem Ind Ltd | Ester exchange of carbonate |
| JPS54125617A (en) | 1978-03-20 | 1979-09-29 | Mitsubishi Chem Ind Ltd | Ester interchange of carbonate |
| DE3017419A1 (de) | 1980-05-07 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung aromatischer polycarbonate |
| JPS57176932A (en) | 1981-04-24 | 1982-10-30 | Asahi Chem Ind Co Ltd | Preparation of carbonic acid ester |
| DE3302525A1 (de) | 1983-01-26 | 1984-07-26 | Basf Ag, 6700 Ludwigshafen | Destillationskolonne zur destillativen zerlegung eines aus mehreren fraktionen bestehenden zulaufproduktes |
| US4552704A (en) | 1983-12-27 | 1985-11-12 | General Electric Company | Process for the production of aromatic carbonates |
| US4554110A (en) | 1983-12-27 | 1985-11-19 | General Electric Company | Process for the preparation of aromatic carbonates |
| JPH06725B2 (ja) | 1985-01-29 | 1994-01-05 | ダイセル化学工業株式会社 | 炭酸ジフエニルの製造方法 |
| DE3809417A1 (de) | 1988-03-21 | 1989-10-12 | Henkel Kgaa | Verfahren zur kontinuierlichen veresterung von fettsaeuren |
| JPH0710314B2 (ja) | 1987-06-26 | 1995-02-08 | ジューキ株式会社 | ミシンの上下送り量制御装置 |
| JPH07100713B2 (ja) | 1987-10-02 | 1995-11-01 | 財団法人相模中央化学研究所 | １４−フルオロアントラサイクリン誘導体 |
| JPH0193560A (ja) | 1987-10-05 | 1989-04-12 | Asahi Chem Ind Co Ltd | ジアリールカーボネートの製造法 |
| CA2013689C (en) | 1987-10-05 | 1997-10-28 | Shinsuke Fukuoka | Process for producing diaryl carbonate |
| US5034557A (en) | 1988-04-16 | 1991-07-23 | Mitsui Petrochemical Industries, Ltd. | Process for production of aromatic carbonate compound |
| KR940005956B1 (ko) * | 1989-12-28 | 1994-06-25 | 아사히가세이고오교 가부시끼가이샤 | 방향족 카르보네이트의 연속 제조방법 |
| DE4006520A1 (de) | 1990-03-02 | 1991-09-05 | Bayer Ag | Verfahren zur herstellung von mindestens eine aromatische estergruppe enthaltenden kohlensaeurediestern |
| DE4036594A1 (de) | 1990-11-16 | 1992-05-21 | Bayer Ag | Verfahren zur herstellung von aromatischen kohlensaeurediestern |
| DE4226755A1 (de) * | 1992-08-13 | 1994-02-17 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Diarylcarbonaten aus Dialkylcarbonaten |
| DE4226756A1 (de) | 1992-08-13 | 1994-02-17 | Bayer Ag | Verfahren zur Herstellung von Dicarbonaten |
| JP3546098B2 (ja) * | 1995-08-23 | 2004-07-21 | 三菱化学株式会社 | ジアリールカーボネートの連続的製造方法 |
| JP3846926B2 (ja) * | 1995-12-27 | 2006-11-15 | 日本ジーイープラスチックス株式会社 | 芳香族カーボネートの連続的製造方法 |
| DE19914966A1 (de) | 1999-04-01 | 2000-10-05 | Basf Ag | Verfahren zur kontinuierlich betriebenen destillativen Abtrennung eines höherschmelzenden Stoffes |
| US6294684B1 (en) | 1999-12-08 | 2001-09-25 | General Electric Company | Method and apparatus for the continuous production of diaryl carbonates |
| JP2002020351A (ja) | 2000-07-05 | 2002-01-23 | Mitsubishi Gas Chem Co Inc | ジアリールカーボネート製造時の熱回収方法 |
| US6515187B1 (en) * | 2001-10-03 | 2003-02-04 | Atofina Chemicals, Inc. | Process for recovering acrolein or propionaldehyde from dilute aqueous streams |
| JP2004075577A (ja) * | 2002-08-13 | 2004-03-11 | Mitsubishi Chemicals Corp | 芳香族カーボネート類の製造方法 |
| WO2004016577A1 (ja) | 2002-08-12 | 2004-02-26 | Mitsubishi Chemical Corporation | 芳香族カーボネート類の製造方法 |
| US7151189B2 (en) | 2003-06-19 | 2006-12-19 | General Electric Company | Method and apparatus for waste stream recovery |
| US7141641B2 (en) | 2003-06-26 | 2006-11-28 | General Electric Company | Method and apparatus for production of alkyl aryl ether and diaryl carbonate |
| RU2329250C2 (ru) * | 2003-06-27 | 2008-07-20 | Асахи Касеи Кемикалз Корпорейшн | Способ получения ароматического карбоната |
| WO2006001256A1 (ja) | 2004-06-25 | 2006-01-05 | Asahi Kasei Chemicals Corporation | 芳香族カーボネートの工業的製造法 |
| EA011128B1 (ru) | 2004-06-25 | 2008-12-30 | Асахи Касеи Кемикалз Корпорейшн | Способ промышленного получения ароматического карбоната |
| BRPI0513251A (pt) | 2004-07-13 | 2008-05-13 | Asahi Kasei Chemicals Corp | processo para a produção de um carbonato aromático, e, carbonato aromático |
| WO2006006566A1 (ja) | 2004-07-13 | 2006-01-19 | Asahi Kasei Chemicals Corporation | 芳香族カーボネート類の工業的製造法 |
| CN100543006C (zh) | 2004-07-14 | 2009-09-23 | 旭化成化学株式会社 | 芳香族碳酸酯类的工业制备方法 |
| CN100532348C (zh) | 2004-07-14 | 2009-08-26 | 旭化成化学株式会社 | 芳香族碳酸酯类的工业制备方法 |
| JP2007326782A (ja) | 2004-09-21 | 2007-12-20 | Asahi Kasei Chemicals Corp | 副生アルコール類の工業的分離装置 |
| BRPI0514936A (pt) | 2004-09-27 | 2008-07-01 | Asahi Kasei Chemicals Corp | aperfeiçoamento em um processo industrial para a produção de um carbonato aromático |
| US7378540B2 (en) * | 2005-10-21 | 2008-05-27 | Catalytic Distillation Technologies | Process for producing organic carbonates |
| JP5344927B2 (ja) * | 2006-11-28 | 2013-11-20 | 旭化成ケミカルズ株式会社 | 高品質芳香族ポリカーボネートを工業的規模で製造する方法 |
| EP1995233A3 (de) * | 2007-05-25 | 2010-06-02 | Bayer MaterialScience AG | Verfahren zur Herstellung von Diaryl- oder Arylalkylcarbonaten aus Dialkylcarbonaten |
| DE102007044033A1 (de) * | 2007-09-14 | 2009-03-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diaryl- oder Alkylarylcarbonaten aus Dialkylcarbonaten |
-
2008
- 2008-06-21 DE DE102008029514A patent/DE102008029514A1/de not_active Withdrawn
-
2009
- 2009-06-06 EP EP20090007511 patent/EP2135857B1/de not_active Not-in-force
- 2009-06-06 ES ES09007511.0T patent/ES2540226T3/es active Active
- 2009-06-12 US US12/483,669 patent/US9040732B2/en not_active Expired - Fee Related
- 2009-06-19 TW TW098120528A patent/TWI455923B/zh not_active IP Right Cessation
- 2009-06-19 SG SG2013048012A patent/SG192423A1/en unknown
- 2009-06-19 JP JP2009146450A patent/JP5596307B2/ja not_active Expired - Fee Related
- 2009-06-19 RU RU2009123374/04A patent/RU2515993C2/ru not_active IP Right Cessation
- 2009-06-19 KR KR1020090055010A patent/KR101651673B1/ko not_active Expired - Fee Related
- 2009-06-19 SG SG200904220-1A patent/SG158046A1/en unknown
- 2009-06-22 CN CN200910146211.5A patent/CN101607908B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101651673B1 (ko) | 2016-08-26 |
| US9040732B2 (en) | 2015-05-26 |
| DE102008029514A1 (de) | 2009-12-24 |
| RU2009123374A (ru) | 2010-12-27 |
| CN101607908B (zh) | 2014-07-23 |
| JP5596307B2 (ja) | 2014-09-24 |
| EP2135857B1 (de) | 2015-05-06 |
| ES2540226T3 (es) | 2015-07-09 |
| EP2135857A2 (de) | 2009-12-23 |
| KR20090132555A (ko) | 2009-12-30 |
| EP2135857A3 (de) | 2010-06-02 |
| CN101607908A (zh) | 2009-12-23 |
| RU2515993C2 (ru) | 2014-05-20 |
| SG158046A1 (en) | 2010-01-29 |
| TW201016660A (en) | 2010-05-01 |
| JP2010006808A (ja) | 2010-01-14 |
| US20100010252A1 (en) | 2010-01-14 |
| TWI455923B (zh) | 2014-10-11 |
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