JP5600268B2 - ポリカーボネートの製造方法 - Google Patents
ポリカーボネートの製造方法 Download PDFInfo
- Publication number
- JP5600268B2 JP5600268B2 JP2010128452A JP2010128452A JP5600268B2 JP 5600268 B2 JP5600268 B2 JP 5600268B2 JP 2010128452 A JP2010128452 A JP 2010128452A JP 2010128452 A JP2010128452 A JP 2010128452A JP 5600268 B2 JP5600268 B2 JP 5600268B2
- Authority
- JP
- Japan
- Prior art keywords
- alkali metal
- solution
- metal chloride
- polycarbonate
- hydroxide solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000004417 polycarbonate Substances 0.000 title claims description 90
- 229920000515 polycarbonate Polymers 0.000 title claims description 90
- 238000004519 manufacturing process Methods 0.000 title description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 225
- 239000000243 solution Substances 0.000 claims description 199
- 238000000034 method Methods 0.000 claims description 105
- 238000006243 chemical reaction Methods 0.000 claims description 68
- 239000012528 membrane Substances 0.000 claims description 65
- 238000005868 electrolysis reaction Methods 0.000 claims description 62
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- 230000008569 process Effects 0.000 claims description 57
- 238000004821 distillation Methods 0.000 claims description 53
- 230000003204 osmotic effect Effects 0.000 claims description 50
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 39
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 27
- 229930185605 Bisphenol Natural products 0.000 claims description 26
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 25
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 239000002699 waste material Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 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 14
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 239000003463 adsorbent Substances 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000012267 brine Substances 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 275
- 239000011780 sodium chloride Substances 0.000 description 137
- 239000002351 wastewater Substances 0.000 description 82
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 239000003014 ion exchange membrane Substances 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- 238000005406 washing Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 238000009792 diffusion process Methods 0.000 description 11
- 238000004064 recycling Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000006056 electrooxidation reaction Methods 0.000 description 7
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 5
- 229910001902 chlorine oxide Inorganic materials 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- -1 polypropylene Polymers 0.000 description 5
- 238000005086 pumping Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 5
- 238000011144 upstream manufacturing Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000005949 ozonolysis reaction Methods 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000010865 sewage Substances 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 2
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 2
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 2
- XSVZEASGNTZBRQ-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfinylphenol Chemical compound OC1=CC=CC=C1S(=O)C1=CC=CC=C1O XSVZEASGNTZBRQ-UHFFFAOYSA-N 0.000 description 2
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 2
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical compound CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 description 2
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 2
- UYSNUYNDKXZDQJ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-1-methylindol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UYSNUYNDKXZDQJ-UHFFFAOYSA-N 0.000 description 2
- OEAKXHPGAATPBS-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-1-phenylindol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2N(C=2C=CC=CC=2)C1=O OEAKXHPGAATPBS-UHFFFAOYSA-N 0.000 description 2
- XHASMJXNUHCHBL-UHFFFAOYSA-N 4-(1-phenylethyl)phenol Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=CC=C1 XHASMJXNUHCHBL-UHFFFAOYSA-N 0.000 description 2
- SUCTVKDVODFXFX-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)sulfonyl-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(S(=O)(=O)C=2C=C(C)C(O)=C(C)C=2)=C1 SUCTVKDVODFXFX-UHFFFAOYSA-N 0.000 description 2
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 2
- DUKMWXLEZOCRSO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)-1-phenylpropan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)CC1=CC=CC=C1 DUKMWXLEZOCRSO-UHFFFAOYSA-N 0.000 description 2
- YICHMIMRBUIUJT-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]phenyl]propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C=CC=2)C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 YICHMIMRBUIUJT-UHFFFAOYSA-N 0.000 description 2
- NIRYBKWMEWFDPM-UHFFFAOYSA-N 4-[3-(4-hydroxyphenyl)-3-methylbutyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)CCC1=CC=C(O)C=C1 NIRYBKWMEWFDPM-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
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 2
- UHHCGGHXJMNXHF-UHFFFAOYSA-N OC1=CC=C(C=C1)C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O Chemical compound OC1=CC=C(C=C1)C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O UHHCGGHXJMNXHF-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
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- ZEKCYPANSOJWDH-UHFFFAOYSA-N 3,3-bis(4-hydroxy-3-methylphenyl)-1H-indol-2-one Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3NC2=O)C=2C=C(C)C(O)=CC=2)=C1 ZEKCYPANSOJWDH-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(C(C=C)C=C)[C@@]1C=C[C@@](C)(C[*+])CC1 Chemical compound CC(C)(C(C=C)C=C)[C@@]1C=C[C@@](C)(C[*+])CC1 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004262 Ethyl gallate Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- KCSFGDIFODLKDB-UHFFFAOYSA-N OC1=CC=C(C=C1)C1C(N(C2=CC=CC=C12)C)=O Chemical compound OC1=CC=C(C=C1)C1C(N(C2=CC=CC=C12)C)=O KCSFGDIFODLKDB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 210000001601 blood-air barrier Anatomy 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
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- 238000007872 degassing Methods 0.000 description 1
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- 230000001419 dependent effect Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- 239000013557 residual solvent Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 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
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- WEQHQGJDZLDFID-UHFFFAOYSA-J thorium(iv) chloride Chemical compound Cl[Th](Cl)(Cl)Cl WEQHQGJDZLDFID-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/364—Membrane distillation
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- C01D3/04—Chlorides
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- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
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Description
(a) 塩素を一酸化炭素と反応させることによってホスゲンを製造する工程;
(b) 工程(a)において生じられるホスゲンを水性アルカリ金属含有塩基の存在下において少なくとも1種類のビスフェノールと反応させてポリカーボネートおよびアルカリ金属塩化物含有反応廃水溶液を生じる工程;
(c) 工程(b)において生じられるポリカーボネートをアルカリ金属塩化物含有反応廃水溶液から分離し、ワークアップ(working up)する工程;
(e) 工程(c)の後に残るアルカリ金属塩化物含有反応廃水溶液の少なくとも一部を浸透膜蒸留によって蒸留して濃縮アルカリ金属塩化物含有溶液を得る工程;
(f) 工程(e)からのアルカリ金属塩化物含有溶液の少なくとも一部を電気化学的に酸化して塩素、アルカリ金属水酸化物溶液および、任意に水素を得る工程;
を包含する、ポリカーボネートの製造方法である。
HO−Z−OH
〔式中、Zは、炭素原子を6〜45個有する芳香族部分であり、前記芳香族部分が任意に1以上の芳香環を含み、任意に置換されていてもよく、任意に脂肪族部分または脂環式部分またはヘテロ原子をブリッジユニットとして含んでいてもよい。〕
のビスフェノールである、上記方法である。
(aa) 工程(b)において生成されるポリカーボネートを含有する有機相をアルカリ金属塩化物含有反応廃水溶液から分離する工程;および
(bb) 工程(aa)において得られる有機相を少なくとも1回洗浄する工程
を包含し、工程(bb)の洗浄相の少なくとも一部を、要すれば触媒残留物および/または有機溶媒残留物の分離後に、工程(b)における使用用のアルカリ金属水酸化物水溶液製造用の水の部分代用品として使用する、上記方法である。
(a) 塩素を一酸化炭素と反応させることによってホスゲンを生成する工程、
(b) 工程(a)において生じられるホスゲンを、水性アルカリ金属含有塩基、特にナトリウム含有塩基、適切な場合窒素触媒、および適切な場合有機溶媒の存在下において少なくとも1種類のビスフェノールと反応させてポリカーボネートおよびアルカリ金属塩化物含有反応廃水溶液、特に塩化ナトリウム含有反応廃水溶液、を生じる工程、
(c) 工程(b)において生じられるポリカーボネートを分離し、ワークアップする工程、
(d) 適切な場合、工程(c)で残る溶媒残留物および、適切な場合、触媒残留物のアルカリ金属塩化物含有溶液からの、特に抽出または溶液をスチームでストリップすることによる、分離(d1)、および次の吸着剤、特に活性炭、を用いる処理(d2)、
(e) 工程(c)または(d)から残るアルカリ金属塩化物含有溶液の少なくともいくつかの浸透膜蒸留、
(f) 塩素、アルカリ金属水酸化物溶液および、適切な場合水素を生じる、工程(e)からのアルカリ金属塩化物含有溶液の少なくともいくつかの電気化学的酸化
を包含する。
HO−Z−OH
〔式中、Zは、炭素原子を6〜45個有する芳香族部分であり、1個以上の芳香環を含んでいてもよく、置換されていてもよく、脂肪族部分または脂環式部分またはヘテロ原子をブリッジユニットとして含んでいてもよい。〕
のビスフェノールである。
Na、K、Li水酸化物
の水酸化物を有するアルカリ金属水酸化物溶液であり、適切な場合、アルカリ土類金属水酸化物を使用してもよい。水酸化ナトリウム溶液が好ましく、この新規の方法では、好ましくは10〜55重量%溶液として使用される。
(aa) ポリカーボネート含有有機相と水性アルカリ金属塩化物含有反応廃水溶液とを分離する工程
(bb) 少なくとも1回、好ましくは少なくとも2回、特に好ましくは5回、工程(aa)において得られるポリカーボネート含有有機相を洗浄し、それぞれの洗液を分離する工程
を包含する。
(a)ポリカーボネートの製造およびワークアップ
YI =1.35(ASTM E 313の記載に準拠して測定)
ηrel =1.195(ISO 1628/4の記載に準拠して測定)
フェノール性OH =85ppm(フェノール性末端基をTiCl4で染色した後に紫外線分光法によって546nmにおいて測定)
(a)ポリカーボネートの製造およびワークアップ
(a)ポリカーボネートの製造およびワークアップ
(a)ポリカーボネートの製造およびワークアップ
(a)ポリカーボネートの製造およびワークアップ
Claims (12)
- (a) 塩素を一酸化炭素と反応させることによってホスゲンを生成する工程;
(b) 工程(a)において生成されるホスゲンを、塩基を含むアルカリ金属水溶液の存在下で少なくとも1種類のビスフェノールと反応させてポリカーボネートおよびアルカリ金属塩化物含有反応廃水溶液を生成する工程;
(c) 工程(b)において生成されるポリカーボネートをアルカリ金属塩化物含有反応廃水溶液から分離し、ワークアップする工程;
(e) 工程(c)の後に残るアルカリ金属塩化物含有反応廃水溶液の少なくとも一部を浸透膜蒸留によって蒸留して濃縮アルカリ金属塩化物含有溶液を得る工程;
(f) 工程(e)のアルカリ金属塩化物含有溶液の少なくとも一部を電気化学的に酸化して塩素、アルカリ金属水酸化物溶液、および任意に水素を得る工程;
を包含する、ポリカーボネートの製造方法。 - 更に工程(d)において、工程(c)後に残るアルカリ金属塩化物含有反応廃水溶液から溶媒残留物および、要すれば、触媒残留物を分離し(d1)、次に生じる溶液を工程(e)の浸透膜蒸留に供給することを包含する、請求項1に記載の方法。
- 該アルカリ金属塩化物含有反応廃水溶液をスチームで抽出するかまたはストリップし、および/または次に該アルカリ金属塩化物含有反応廃水溶液を吸着剤で処理する(d2)ことによって工程(d)を達成する、請求項2に記載の方法。
- 工程(e)における浸透膜蒸留がアルカリ金属水酸化物溶液を水アクセプターとして使用する、請求項2に記載の方法。
- 工程(e)における浸透膜蒸留を10〜100℃の範囲の温度において行う、請求項1に記載の方法。
- 工程(e)における浸透膜蒸留を1.0〜1.4barの範囲の絶対圧力において行う、請求項1に記載の方法。
- 工程(e)における浸透膜蒸留を20〜150mbarの範囲の差圧において行う、請求項1に記載の方法。
- 工程(e)における浸透膜蒸留がAccurel PP膜を使用する、請求項1に記載の方法。
- 工程(e)において得られるアルカリ金属塩化物含有溶液の少なくとも一部を、塩素、水酸化ナトリウム溶液および要すれば水素を生成する膜電解のブラインサーキットに添加する、請求項1に記載の方法。
- 工程(f)において電気分解においてアルカリ金属塩化物濃度を増加させるために追加のアルカリ金属塩化物をアルカリ金属塩化物含有溶液に添加する、請求項1に記載の方法。
- 該少なくとも1種類のビスフェノールが一般式
HO−Z−OH
〔式中、Zは、炭素原子を6〜45個有する芳香族部分であり、該芳香族部分が任意に1以上の芳香環を含み、任意に置換されていてもよく、任意に脂肪族部分または脂環式部分またはヘテロ原子をブリッジユニットとして含んでいてもよい。〕
のビスフェノールである、請求項1に記載の方法。 - 該アルカリ金属塩化物含有反応廃水溶液のアルカリ金属塩化物のアルカリ金属がナトリウムである、請求項1に記載の方法。
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DE10063297A1 (de) * | 2000-12-19 | 2002-06-20 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Kohlensäurediarylester |
JP2003063999A (ja) | 2001-08-28 | 2003-03-05 | Mitsubishi Heavy Ind Ltd | 有機ハロゲン化物分解処理システム |
DE10207442A1 (de) | 2002-02-22 | 2003-09-11 | Bayer Ag | Aufbereitung von Kochsalz enthaltenden Abwässern zum Einsatz in der Chlor-Alkali-Elektrolyse |
WO2004078657A1 (en) | 2003-03-05 | 2004-09-16 | Dow Global Technologies Inc. | A method for purifying wastewater |
EP1640357B1 (en) | 2003-06-27 | 2011-08-31 | Asahi Kasei Chemicals Corporation | Method for producing aromatic carbonate |
CA2469769A1 (en) | 2004-06-04 | 2005-12-04 | Aker Kvaerner Canada Inc. | Apparatus and method for spent alkali metal halide solution concentration using osmotic membrane distillation |
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2009
- 2009-06-04 DE DE102009023940A patent/DE102009023940A1/de not_active Withdrawn
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- 2010-05-21 US US12/784,850 patent/US8106144B2/en not_active Expired - Fee Related
- 2010-05-26 EP EP10005449.3A patent/EP2286898B1/de not_active Revoked
- 2010-06-02 SG SG201003849-5A patent/SG166762A1/en unknown
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- 2010-06-03 KR KR1020100052174A patent/KR101752915B1/ko active IP Right Grant
- 2010-06-04 JP JP2010128452A patent/JP5600268B2/ja not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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CN102010505A (zh) | 2011-04-13 |
TW201111412A (en) | 2011-04-01 |
US20100324256A1 (en) | 2010-12-23 |
JP2011012257A (ja) | 2011-01-20 |
CN102010505B (zh) | 2014-07-16 |
DE102009023940A1 (de) | 2010-12-09 |
TWI481642B (zh) | 2015-04-21 |
KR20100130959A (ko) | 2010-12-14 |
US8106144B2 (en) | 2012-01-31 |
SG166762A1 (en) | 2010-12-29 |
EP2286898B1 (de) | 2015-09-23 |
KR101752915B1 (ko) | 2017-07-03 |
EP2286898A1 (de) | 2011-02-23 |
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