CN102206158A - 制备碳酸二芳基酯和聚碳酸酯的方法 - Google Patents
制备碳酸二芳基酯和聚碳酸酯的方法 Download PDFInfo
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- CN102206158A CN102206158A CN2011100782753A CN201110078275A CN102206158A CN 102206158 A CN102206158 A CN 102206158A CN 2011100782753 A CN2011100782753 A CN 2011100782753A CN 201110078275 A CN201110078275 A CN 201110078275A CN 102206158 A CN102206158 A CN 102206158A
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- Prior art keywords
- phenol
- hydrogenchloride
- chlorine
- phosgene
- hydrochloric acid
- 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.)
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- -1 diaryl carbonates Chemical class 0.000 title claims abstract description 86
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 39
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title abstract description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 284
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 146
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 146
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 137
- 238000000034 method Methods 0.000 claims abstract description 134
- 239000000460 chlorine Substances 0.000 claims abstract description 80
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 79
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 76
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 74
- 238000006243 chemical reaction Methods 0.000 claims abstract description 67
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000002360 preparation method Methods 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 26
- 230000003647 oxidation Effects 0.000 claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 14
- 239000007789 gas Substances 0.000 claims description 81
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 57
- 239000001301 oxygen Substances 0.000 claims description 57
- 229910052760 oxygen Inorganic materials 0.000 claims description 57
- 238000005868 electrolysis reaction Methods 0.000 claims description 35
- 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 31
- 238000009792 diffusion process Methods 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 229930185605 Bisphenol Natural products 0.000 claims description 26
- 239000008246 gaseous mixture Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- 239000007864 aqueous solution Substances 0.000 claims description 19
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- 239000000470 constituent Substances 0.000 claims description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
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- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 7
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- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 6
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- BVJAAVMKGRODCT-UHFFFAOYSA-N sulfanylidenerhodium Chemical compound [Rh]=S BVJAAVMKGRODCT-UHFFFAOYSA-N 0.000 claims description 6
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- 239000006227 byproduct Substances 0.000 description 16
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 15
- 239000010936 titanium Substances 0.000 description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000000066 reactive distillation Methods 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- 239000010408 film Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 229910052719 titanium Inorganic materials 0.000 description 11
- 239000002912 waste gas Substances 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
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- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 7
- 230000004927 fusion Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000557 Nafion® Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
- 239000010970 precious metal Substances 0.000 description 6
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- 150000002431 hydrogen Chemical group 0.000 description 5
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- 238000007725 thermal activation Methods 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 description 4
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- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 3
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- 238000004438 BET method Methods 0.000 description 3
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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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
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- 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
- C01B7/04—Preparation of chlorine from hydrogen chloride
-
- 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
- C01B7/07—Purification ; Separation
- C01B7/0706—Purification ; Separation of hydrogen chloride
- C01B7/0731—Purification ; Separation of hydrogen chloride by extraction
-
- 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
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- 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
- 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
-
- 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
Abstract
Description
Claims (21)
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EP10158446 | 2010-03-30 | ||
EP10158446.4 | 2010-03-30 |
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CN102206158A true CN102206158A (zh) | 2011-10-05 |
CN102206158B CN102206158B (zh) | 2015-07-22 |
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US (1) | US9175135B2 (zh) |
EP (1) | EP2371807B1 (zh) |
JP (2) | JP6122570B2 (zh) |
KR (1) | KR101834011B1 (zh) |
CN (1) | CN102206158B (zh) |
ES (1) | ES2644525T3 (zh) |
RU (1) | RU2011111758A (zh) |
SG (1) | SG174715A1 (zh) |
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CN103664628A (zh) * | 2013-12-12 | 2014-03-26 | 武汉工程大学 | 脂肪族氯代物间接光气法制备有机碳酸酯的方法 |
CN110869537A (zh) * | 2017-07-03 | 2020-03-06 | 科思创德国股份有限公司 | 用于制备碳酸芳基烷基酯或碳酸二芳基酯的电化学方法 |
CN111517922A (zh) * | 2020-04-28 | 2020-08-11 | 万华化学集团股份有限公司 | 一种制备4-氯-3,5-二甲基苯酚的方法 |
CN114174256A (zh) * | 2019-08-22 | 2022-03-11 | 富士胶片株式会社 | 羰基化合物的制造方法及制造羰基化合物的流动式反应系统 |
CN114929780A (zh) * | 2020-01-17 | 2022-08-19 | 科思创德国股份有限公司 | 未反应的碳酸二芳基酯的回收改进的生产聚碳酸酯的方法 |
Families Citing this family (16)
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SG174715A1 (en) * | 2010-03-30 | 2011-10-28 | Bayer Materialscience Ag | Process for preparing diaryl carbonates and polycarbonates |
EP2586767A1 (de) | 2011-10-25 | 2013-05-01 | Bayer MaterialScience AG | Verfahren zur Herstellung von Diarylcarbonaten und Polycarbonaten |
WO2013189861A1 (en) | 2012-06-19 | 2013-12-27 | Akzo Nobel Chemicals International B.V. | Process for the preparation of cyclic organic carbonates |
EP2711353B1 (en) | 2012-09-20 | 2018-10-31 | SABIC Global Technologies B.V. | Process for the continuous manufacture of aryl alkyl carbonate and diaryl carbonate using vapor recompression |
WO2014095776A1 (de) * | 2012-12-18 | 2014-06-26 | Bayer Materialscience Ag | Verfahren zur herstellung von diarylcarbonat |
KR102041556B1 (ko) * | 2013-07-26 | 2019-11-06 | 사빅 글로벌 테크놀러지스 비.브이. | 고순도 포스겐의 제조 방법 및 제조 장치 |
WO2015013655A1 (en) | 2013-07-26 | 2015-01-29 | Sabic Innovative Plastics Ip B.V. | Method and apparatus for producing high purity phosgene |
US9695106B2 (en) | 2014-02-04 | 2017-07-04 | Sabic Global Technologies B.V. | Method for producing carbonates |
WO2015119982A2 (en) | 2014-02-04 | 2015-08-13 | Sabic Global Technologies B.V. | Method for producing carbonates |
JP6605588B2 (ja) | 2014-05-09 | 2019-11-13 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | ジアリールカーボネート類の製造方法 |
US9643163B2 (en) | 2014-10-10 | 2017-05-09 | Crystaphase Products, Inc. | Heterogeneous catalyst for transesterification and method of preparing same |
US10144696B2 (en) | 2015-04-17 | 2018-12-04 | Crystaphase Products, Inc. | Heterogeneous catalyst for transesterification and method of preparing same |
CN114206824A (zh) | 2019-08-22 | 2022-03-18 | 富士胶片株式会社 | 羰基化合物的制造方法及制造羰基化合物的流动式反应系统 |
EP4083106B1 (de) * | 2021-04-30 | 2024-04-10 | Covestro Deutschland AG | Verfahren zur herstellung von polycarbonat mit verbesserter nachhaltigkeit |
TW202313172A (zh) * | 2021-07-27 | 2023-04-01 | 美商亞比馬利股份有限公司 | 用於純化含有有機雜質的鹵化氫溶液的方法 |
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2011
- 2011-03-25 SG SG2011021441A patent/SG174715A1/en unknown
- 2011-03-25 US US13/071,944 patent/US9175135B2/en not_active Expired - Fee Related
- 2011-03-28 ES ES11160021.9T patent/ES2644525T3/es active Active
- 2011-03-28 EP EP11160021.9A patent/EP2371807B1/de not_active Not-in-force
- 2011-03-29 RU RU2011111758/04A patent/RU2011111758A/ru not_active Application Discontinuation
- 2011-03-29 KR KR1020110028181A patent/KR101834011B1/ko active IP Right Grant
- 2011-03-30 CN CN201110078275.3A patent/CN102206158B/zh not_active Expired - Fee Related
- 2011-03-30 JP JP2011076061A patent/JP6122570B2/ja not_active Expired - Fee Related
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2016
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CN103635455A (zh) * | 2011-07-08 | 2014-03-12 | 拜耳知识产权有限责任公司 | 制备碳酸二芳基酯的方法 |
CN103635455B (zh) * | 2011-07-08 | 2017-03-01 | 科思创德国股份有限公司 | 制备碳酸二芳基酯的方法 |
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CN114929780A (zh) * | 2020-01-17 | 2022-08-19 | 科思创德国股份有限公司 | 未反应的碳酸二芳基酯的回收改进的生产聚碳酸酯的方法 |
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CN111517922B (zh) * | 2020-04-28 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备4-氯-3,5-二甲基苯酚的方法 |
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SG174715A1 (en) | 2011-10-28 |
JP6313805B2 (ja) | 2018-04-18 |
US9175135B2 (en) | 2015-11-03 |
JP2011207883A (ja) | 2011-10-20 |
CN102206158B (zh) | 2015-07-22 |
JP2016183162A (ja) | 2016-10-20 |
EP2371807A1 (de) | 2011-10-05 |
KR20110109979A (ko) | 2011-10-06 |
JP6122570B2 (ja) | 2017-04-26 |
KR101834011B1 (ko) | 2018-03-02 |
RU2011111758A (ru) | 2012-10-10 |
US20110245527A1 (en) | 2011-10-06 |
EP2371807B1 (de) | 2017-07-26 |
ES2644525T3 (es) | 2017-11-29 |
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