TWI444363B - 製造二芳基碳酸酯之方法 - Google Patents
製造二芳基碳酸酯之方法 Download PDFInfo
- Publication number
- TWI444363B TWI444363B TW097147229A TW97147229A TWI444363B TW I444363 B TWI444363 B TW I444363B TW 097147229 A TW097147229 A TW 097147229A TW 97147229 A TW97147229 A TW 97147229A TW I444363 B TWI444363 B TW I444363B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkali metal
- metal chloride
- solution
- containing solution
- sodium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 122
- -1 diaryl carbonate Chemical compound 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 52
- 230000008569 process Effects 0.000 title abstract description 54
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims abstract description 123
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 70
- 239000000243 solution Substances 0.000 claims description 179
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 144
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 37
- 239000002585 base Substances 0.000 claims description 36
- 239000000460 chlorine Substances 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 24
- 229910052708 sodium Inorganic materials 0.000 claims description 24
- 239000011734 sodium Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 21
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 20
- 239000003513 alkali Substances 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 150000001340 alkali metals Chemical class 0.000 claims description 15
- 230000005012 migration Effects 0.000 claims description 15
- 238000013508 migration Methods 0.000 claims description 15
- 238000004064 recycling Methods 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000012528 membrane Substances 0.000 claims description 14
- 239000003463 adsorbent Substances 0.000 claims description 13
- 239000003014 ion exchange membrane Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 10
- 238000006056 electrooxidation reaction Methods 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012267 brine Substances 0.000 claims description 5
- 238000009792 diffusion process Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 5
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 3
- XZHPXGYRYNDJOD-UHFFFAOYSA-N 4-(8-methylnonyl)phenol Chemical compound CC(C)CCCCCCCC1=CC=C(O)C=C1 XZHPXGYRYNDJOD-UHFFFAOYSA-N 0.000 claims description 3
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 claims description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 3
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 229910001902 chlorine oxide Inorganic materials 0.000 claims description 3
- 150000001896 cresols Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 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 claims description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 3
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 claims description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 claims 1
- 239000002351 wastewater Substances 0.000 abstract description 79
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 227
- 239000011780 sodium chloride Substances 0.000 description 113
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000012670 alkaline solution Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 230000008520 organization Effects 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 238000005201 scrubbing Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- HVXRCAWUNAOCTA-UHFFFAOYSA-N 4-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=C(O)C=C1 HVXRCAWUNAOCTA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012544 monitoring process 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
- 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
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/03—Preparation from chlorides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/80—Phosgene
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D3/00—Halides of sodium, potassium or alkali metals in general
- C01D3/04—Chlorides
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D3/00—Halides of sodium, potassium or alkali metals in general
- C01D3/04—Chlorides
- C01D3/06—Preparation by working up brines; seawater or spent lyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B1/00—Electrolytic production of inorganic compounds or non-metals
- C25B1/01—Products
- C25B1/34—Simultaneous production of alkali metal hydroxides and chlorine, oxyacids or salts of chlorine, e.g. by chlor-alkali electrolysis
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B1/00—Electrolytic production of inorganic compounds or non-metals
- C25B1/01—Products
- C25B1/34—Simultaneous production of alkali metal hydroxides and chlorine, oxyacids or salts of chlorine, e.g. by chlor-alkali electrolysis
- C25B1/46—Simultaneous production of alkali metal hydroxides and chlorine, oxyacids or salts of chlorine, e.g. by chlor-alkali electrolysis in diaphragm cells
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B15/00—Operating or servicing cells
- C25B15/08—Supplying or removing reactants or electrolytes; Regeneration of electrolytes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Metallurgy (AREA)
- Electrochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Removal Of Specific Substances (AREA)
- Water Treatment By Electricity Or Magnetism (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007058701A DE102007058701A1 (de) | 2007-12-06 | 2007-12-06 | Verfahren zur Herstellung von Diarylcarbonat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200938525A TW200938525A (en) | 2009-09-16 |
| TWI444363B true TWI444363B (zh) | 2014-07-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097147229A TWI444363B (zh) | 2007-12-06 | 2008-12-05 | 製造二芳基碳酸酯之方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20090173636A1 (https=) |
| EP (1) | EP2229343B1 (https=) |
| JP (1) | JP5508278B2 (https=) |
| KR (1) | KR20100106331A (https=) |
| CN (1) | CN101888971B (https=) |
| AT (1) | ATE525328T1 (https=) |
| DE (1) | DE102007058701A1 (https=) |
| ES (1) | ES2373196T3 (https=) |
| RU (1) | RU2496765C2 (https=) |
| TW (1) | TWI444363B (https=) |
| WO (1) | WO2009071211A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE501997T1 (de) * | 2003-11-20 | 2011-04-15 | Solvay | Verfahren zur herstellung von dichlorpropanol |
| CA2608722A1 (en) * | 2005-05-20 | 2006-09-28 | Solvay (Societe Anonyme) | Method for making an epoxide starting with a polyhydroxylated aliphatic hydrocarbon and a chlorinating agent |
| KR20080037613A (ko) | 2005-05-20 | 2008-04-30 | 솔베이(소시에떼아노님) | 폴리히드록실화 지방족 탄화수소의 클로로히드린으로의전환 방법 |
| KR100979372B1 (ko) | 2006-06-14 | 2010-08-31 | 솔베이(소시에떼아노님) | 조 글리세롤계 생성물, 그 정제방법 및 디클로로프로판올의제조에의 그 용도 |
| US20100032617A1 (en) * | 2007-02-20 | 2010-02-11 | Solvay (Societe Anonyme) | Process for manufacturing epichlorohydrin |
| FR2913684B1 (fr) * | 2007-03-14 | 2012-09-14 | Solvay | Procede de fabrication de dichloropropanol |
| TW200911693A (en) * | 2007-06-12 | 2009-03-16 | Solvay | Aqueous composition containing a salt, manufacturing process and use |
| TW200911773A (en) | 2007-06-12 | 2009-03-16 | Solvay | Epichlorohydrin, manufacturing process and use |
| FR2918058A1 (fr) * | 2007-06-28 | 2009-01-02 | Solvay | Produit a base de glycerol, procede pour sa purification et son utilisation dans la fabrication de dichloropropanol |
| JP2011502032A (ja) * | 2007-10-02 | 2011-01-20 | ソルヴェイ（ソシエテ アノニム） | 容器の耐腐食性を向上させるためのケイ素を含有する組成物の使用 |
| FR2925045B1 (fr) * | 2007-12-17 | 2012-02-24 | Solvay | Produit a base de glycerol, procede pour son obtention et son utilisation dans la fabrication de dichloropropanol |
| TWI478875B (zh) * | 2008-01-31 | 2015-04-01 | Solvay | 使水性組成物中之有機物質降解之方法 |
| WO2009121853A1 (en) * | 2008-04-03 | 2009-10-08 | Solvay (Société Anonyme) | Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol |
| FR2935968B1 (fr) * | 2008-09-12 | 2010-09-10 | Solvay | Procede pour la purification de chlorure d'hydrogene |
| FR2939434B1 (fr) * | 2008-12-08 | 2012-05-18 | Solvay | Procede de traitement de glycerol. |
| ES2643234T3 (es) | 2010-03-30 | 2017-11-21 | Covestro Deutschland Ag | Procedimiento para la preparación de carbonatos de diarilo y policarbonatos |
| SG174715A1 (en) * | 2010-03-30 | 2011-10-28 | Bayer Materialscience Ag | Process for preparing diaryl carbonates and polycarbonates |
| US9169131B1 (en) * | 2010-04-21 | 2015-10-27 | Trinity Manufacturing, Inc. | System and process for removing total organic carbons from a brine waste stream |
| FR2964096A1 (fr) * | 2010-08-27 | 2012-03-02 | Solvay | Procede d'epuration d'une saumure |
| JP6049087B2 (ja) | 2010-09-30 | 2016-12-21 | ソルヴェイ（ソシエテ アノニム） | 天然起源のエピクロロヒドリンの誘導体 |
| CN102719845A (zh) * | 2012-07-13 | 2012-10-10 | 宜兴方晶科技有限公司 | 一种无氢电解制备甲基磺酸亚锡的方法及其装置 |
| WO2015013655A1 (en) | 2013-07-26 | 2015-01-29 | Sabic Innovative Plastics Ip B.V. | Method and apparatus for producing high purity phosgene |
| CN105408249A (zh) | 2013-07-26 | 2016-03-16 | 沙特基础全球技术有限公司 | 用于生产高纯光气的方法和装置 |
| JP6286057B2 (ja) | 2014-02-04 | 2018-02-28 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | カーボネートを生成する方法 |
| JP6316446B2 (ja) | 2014-02-04 | 2018-04-25 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | カーボネートの製造方法 |
| TW201920769A (zh) * | 2017-07-03 | 2019-06-01 | 德商科思創德意志股份有限公司 | 製備二芳基碳酸酯之電化學法 |
| EP3527696A1 (de) | 2018-02-14 | 2019-08-21 | Covestro Deutschland AG | Verfahren zur aufarbeitung und wiederverwendung von salzhaltigem prozesswasser |
| EP3708698A1 (de) | 2019-03-13 | 2020-09-16 | Covestro Deutschland AG | Verfahren zur aufarbeitung und wiederverwendung von salzhaltigem prozesswasser |
| EP3851478A1 (de) | 2020-01-17 | 2021-07-21 | Covestro Deutschland AG | Verfahren zur herstellung eines polycarbonats mit verbesserter rückgewinnung von nicht umgesetzten diarylcarbonat |
| WO2022096390A1 (de) | 2020-11-06 | 2022-05-12 | Covestro Deutschland Ag | Verfahren zur herstellung eines polyol-gemisches |
| EP4011861A1 (de) | 2020-12-11 | 2022-06-15 | Covestro Deutschland AG | Verfahren zur herstellung von diarylcarbonaten mit geringem phenolgehalt im abwasser |
| KR102578411B1 (ko) * | 2021-04-06 | 2023-09-15 | 서울대학교산학협력단 | 이산화탄소로부터 유기 카보네이트를 합성하기 위한 전기 화학 시스템 및 유기 카보네이트의 합성 방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1056141B (de) * | 1957-04-08 | 1959-04-30 | Bayer Ag | Verfahren zur Herstellung von Diarylcarbonaten |
| BE790369A (fr) | 1971-10-21 | 1973-04-20 | Diamond Shamrock Corp | Procede et appareil pour la preparation d'hydroxydes de metaux alcalins de haute purete dans une cuve electrolytique. |
| US3773634A (en) | 1972-03-09 | 1973-11-20 | Diamond Shamrock Corp | Control of an olyte-catholyte concentrations in membrane cells |
| GB1500288A (en) | 1974-05-21 | 1978-02-08 | Canadian Ind | Purification of brine |
| DE2509036C2 (de) | 1975-03-01 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von symmetrischen Diarylcarbonaten |
| US4578159A (en) * | 1985-04-25 | 1986-03-25 | Olin Corporation | Electrolysis of alkali metal chloride brine in catholyteless membrane cells employing an oxygen consuming cathode |
| DE69009992T2 (de) * | 1989-12-28 | 1995-01-12 | Asahi Kasei Kogyo K.K., Osaka | Kontinuierliches verfahren zur herstellung aromatischer karbonate. |
| GB2260975B (en) | 1991-10-28 | 1995-07-12 | Chang Shih Chang | The process to recover salt from brine waste water |
| DE4238123C2 (de) | 1992-11-12 | 2000-03-09 | Bayer Ag | Verfahren zur Herstellung von thermoplastischen Polycarbonaten |
| DE19600631A1 (de) | 1996-01-10 | 1997-07-17 | Bayer Ag | Verfahren zur Reinigung von Kohlensäurediarylestern |
| CA2261697C (en) * | 1996-07-30 | 2006-11-21 | The Governors Of The University Of Alberta | Process for the production of a polymerized material and the product produced thereby |
| JPH1081986A (ja) | 1996-09-03 | 1998-03-31 | Permelec Electrode Ltd | 水平型複極式電解槽 |
| TW429246B (en) * | 1996-10-04 | 2001-04-11 | Ube Industries | Preparation of diaryl carbonate |
| ES2215682T3 (es) * | 1999-06-18 | 2004-10-16 | Bayer Materialscience Ag | Procedimiento para la degradacion de compuestos organicos en agua. |
| US6340736B1 (en) | 1999-11-29 | 2002-01-22 | General Electric Company | Method and apparatus for the production of polycarbonates with brine recycling |
| EP1112997B1 (en) * | 1999-12-28 | 2009-05-13 | Mitsubishi Chemical Corporation | Process for producing diaryl carbonate |
| DE10063297A1 (de) * | 2000-12-19 | 2002-06-20 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Kohlensäurediarylester |
| DE10063296A1 (de) * | 2000-12-19 | 2002-06-20 | Bayer Ag | Verfahren zur Herstellung von Kohlensäurediarylester |
| DE10063869A1 (de) | 2000-12-21 | 2002-06-27 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Kohlensäurediarylester |
| US20030155301A1 (en) * | 2002-01-04 | 2003-08-21 | General Electric Company | Method of purifying brine |
| DE10207442A1 (de) * | 2002-02-22 | 2003-09-11 | Bayer Ag | Aufbereitung von Kochsalz enthaltenden Abwässern zum Einsatz in der Chlor-Alkali-Elektrolyse |
| DE102004041777A1 (de) * | 2004-08-28 | 2006-03-02 | Bayer Materialscience Ag | Verfahren und Vorrichtung zur Herstellung von Phosgen |
| DE102006041465A1 (de) | 2006-09-02 | 2008-03-06 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diarylcarbonat |
-
2007
- 2007-12-06 DE DE102007058701A patent/DE102007058701A1/de not_active Withdrawn
-
2008
- 2008-11-22 EP EP08856513A patent/EP2229343B1/de not_active Not-in-force
- 2008-11-22 WO PCT/EP2008/009910 patent/WO2009071211A1/de not_active Ceased
- 2008-11-22 KR KR1020107012313A patent/KR20100106331A/ko not_active Ceased
- 2008-11-22 JP JP2010536348A patent/JP5508278B2/ja active Active
- 2008-11-22 ES ES08856513T patent/ES2373196T3/es active Active
- 2008-11-22 CN CN2008801192459A patent/CN101888971B/zh active Active
- 2008-11-22 AT AT08856513T patent/ATE525328T1/de active
- 2008-11-22 RU RU2010127421/04A patent/RU2496765C2/ru not_active IP Right Cessation
- 2008-12-04 US US12/328,434 patent/US20090173636A1/en not_active Abandoned
- 2008-12-05 TW TW097147229A patent/TWI444363B/zh not_active IP Right Cessation
-
2011
- 2011-03-01 US US13/037,909 patent/US8518231B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101888971A (zh) | 2010-11-17 |
| CN101888971B (zh) | 2013-08-21 |
| EP2229343B1 (de) | 2011-09-21 |
| DE102007058701A1 (de) | 2009-06-10 |
| RU2010127421A (ru) | 2012-01-20 |
| RU2496765C2 (ru) | 2013-10-27 |
| US8518231B2 (en) | 2013-08-27 |
| JP2011506278A (ja) | 2011-03-03 |
| EP2229343A1 (de) | 2010-09-22 |
| US20090173636A1 (en) | 2009-07-09 |
| WO2009071211A8 (de) | 2010-06-10 |
| US20110147229A1 (en) | 2011-06-23 |
| TW200938525A (en) | 2009-09-16 |
| JP5508278B2 (ja) | 2014-05-28 |
| ATE525328T1 (de) | 2011-10-15 |
| ES2373196T3 (es) | 2012-02-01 |
| WO2009071211A1 (de) | 2009-06-11 |
| KR20100106331A (ko) | 2010-10-01 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |