TWI818160B - 雙酚之製造方法及聚碳酸酯樹脂之製造方法 - Google Patents
雙酚之製造方法及聚碳酸酯樹脂之製造方法 Download PDFInfo
- Publication number
- TWI818160B TWI818160B TW109108287A TW109108287A TWI818160B TW I818160 B TWI818160 B TW I818160B TW 109108287 A TW109108287 A TW 109108287A TW 109108287 A TW109108287 A TW 109108287A TW I818160 B TWI818160 B TW I818160B
- Authority
- TW
- Taiwan
- Prior art keywords
- bisphenol
- organic phase
- phase
- aqueous phase
- isocyanate
- Prior art date
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- 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 title claims abstract description 254
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 252
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 85
- 229920005668 polycarbonate resin Polymers 0.000 title claims description 58
- 239000004431 polycarbonate resin Substances 0.000 title claims description 58
- 239000012074 organic phase Substances 0.000 claims abstract description 187
- 239000008346 aqueous phase Substances 0.000 claims abstract description 146
- 239000007788 liquid Substances 0.000 claims abstract description 97
- 239000002738 chelating agent Substances 0.000 claims abstract description 53
- 238000002156 mixing Methods 0.000 claims abstract description 41
- 239000003513 alkali Substances 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- 150000002576 ketones Chemical class 0.000 claims description 42
- 239000012071 phase Substances 0.000 claims description 42
- 150000001299 aldehydes Chemical class 0.000 claims description 41
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 28
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 24
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 24
- 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 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- -1 n-octyl Chemical group 0.000 description 133
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 93
- 239000007864 aqueous solution Substances 0.000 description 88
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
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- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 35
- 238000005979 thermal decomposition reaction Methods 0.000 description 34
- 238000005406 washing Methods 0.000 description 34
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- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 30
- 229910052742 iron Inorganic materials 0.000 description 29
- 230000002378 acidificating effect Effects 0.000 description 27
- 238000006116 polymerization reaction Methods 0.000 description 26
- 239000002994 raw material Substances 0.000 description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- 239000000126 substance Substances 0.000 description 24
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 23
- 239000000155 melt Substances 0.000 description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- HSQLYGWQYALUTJ-UHFFFAOYSA-N 2-methyl-3-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC(O)=C1C HSQLYGWQYALUTJ-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
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- YMZDMPPYBDUSMI-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)dodecyl]phenol Chemical compound C=1C=C(O)C=CC=1C(CCCCCCCCCCC)C1=CC=C(O)C=C1 YMZDMPPYBDUSMI-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
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- 239000000047 product Substances 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 10
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- 238000012360 testing method Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
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- 239000002245 particle Substances 0.000 description 7
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241001550224 Apha Species 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
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- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
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JPS58177928A (ja) * | 1982-03-29 | 1983-10-18 | モンサント・カンパニ− | ビス(ヒドロキシフエニル)メタン類の製法 |
JPH0967287A (ja) * | 1995-08-30 | 1997-03-11 | Dainippon Ink & Chem Inc | ビスフェノールfの製造方法 |
TW200916437A (en) * | 2007-03-30 | 2009-04-16 | Mitsubishi Chem Corp | Method of making bisphenol compounds, and a cation-exchange resin catalyst |
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JPS6052738B2 (ja) * | 1980-02-20 | 1985-11-21 | 宇部興産株式会社 | ジヒドロキシジフェニルメタンの脱色方法 |
JP7021559B2 (ja) * | 2017-03-06 | 2022-02-17 | 三菱ケミカル株式会社 | ビスフェノールの製造方法及びポリカーボネート樹脂の製造方法 |
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JPS58177928A (ja) * | 1982-03-29 | 1983-10-18 | モンサント・カンパニ− | ビス(ヒドロキシフエニル)メタン類の製法 |
JPH0967287A (ja) * | 1995-08-30 | 1997-03-11 | Dainippon Ink & Chem Inc | ビスフェノールfの製造方法 |
TW200916437A (en) * | 2007-03-30 | 2009-04-16 | Mitsubishi Chem Corp | Method of making bisphenol compounds, and a cation-exchange resin catalyst |
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