TWI508955B - 以高效率催化劑隨其老化時製備環氧烷之簡化方法 - Google Patents
以高效率催化劑隨其老化時製備環氧烷之簡化方法 Download PDFInfo
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- TWI508955B TWI508955B TW099112280A TW99112280A TWI508955B TW I508955 B TWI508955 B TW I508955B TW 099112280 A TW099112280 A TW 099112280A TW 99112280 A TW99112280 A TW 99112280A TW I508955 B TWI508955 B TW I508955B
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- Prior art keywords
- catalyst
- concentration
- reaction temperature
- alkylene oxide
- effectiveness
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- 238000000034 method Methods 0.000 claims description 80
- 238000005660 chlorination reaction Methods 0.000 claims description 63
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- VODGJKZAAVKBAL-UHFFFAOYSA-L diazanium;manganese(2+);disulfate Chemical compound [NH4+].[NH4+].[Mn+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VODGJKZAAVKBAL-UHFFFAOYSA-L 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LGPMBEHDKBYMNU-UHFFFAOYSA-N ethane;ethene Chemical compound CC.C=C LGPMBEHDKBYMNU-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000003837 high-temperature calcination Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical compound [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 239000011564 manganese citrate Substances 0.000 description 1
- 235000014872 manganese citrate Nutrition 0.000 description 1
- 229940097206 manganese citrate Drugs 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- OUJBVIMYCAJFDN-UHFFFAOYSA-L manganese(2+) sulfonato sulfate Chemical compound S(=O)(=O)([O-])OS(=O)(=O)[O-].[Mn+2] OUJBVIMYCAJFDN-UHFFFAOYSA-L 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- RGVLTEMOWXGQOS-UHFFFAOYSA-L manganese(2+);oxalate Chemical compound [Mn+2].[O-]C(=O)C([O-])=O RGVLTEMOWXGQOS-UHFFFAOYSA-L 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ALTWGIIQPLQAAM-UHFFFAOYSA-N metavanadate Chemical compound [O-][V](=O)=O ALTWGIIQPLQAAM-UHFFFAOYSA-N 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- NFFIWVVINABMKP-UHFFFAOYSA-N methylidynetantalum Chemical compound [Ta]#C NFFIWVVINABMKP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002843 nonmetals Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/22—Synthesis of the oxirane ring by oxidation of saturated compounds with air or molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17124809P | 2009-04-21 | 2009-04-21 |
Publications (2)
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|---|---|
| TW201100394A TW201100394A (en) | 2011-01-01 |
| TWI508955B true TWI508955B (zh) | 2015-11-21 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099112280A TWI508955B (zh) | 2009-04-21 | 2010-04-20 | 以高效率催化劑隨其老化時製備環氧烷之簡化方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8389751B2 (https=) |
| EP (1) | EP2421840B1 (https=) |
| JP (1) | JP2012524785A (https=) |
| KR (1) | KR101745737B1 (https=) |
| CN (1) | CN102414187B (https=) |
| CA (1) | CA2758818C (https=) |
| SG (1) | SG175770A1 (https=) |
| TW (1) | TWI508955B (https=) |
| WO (1) | WO2010123842A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2759397C (en) * | 2009-04-21 | 2019-01-29 | Dow Technology Investments Llc | Improved method of achieving and maintaining a specified alkylene oxide production parameter with a high efficiency catalyst |
| US8742147B2 (en) | 2010-12-08 | 2014-06-03 | Shell Oil Company | Process for improving the selectivity of an EO catalyst |
| US8884037B2 (en) | 2010-12-10 | 2014-11-11 | Dow Technology Investments Llc | Method of reducing the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst |
| SG190901A1 (en) | 2010-12-15 | 2013-07-31 | Dow Technology Investments Llc | Method of starting-up a process of producing an alkylene oxide using a high-efficiency catalyst |
| BR112013027585B1 (pt) | 2011-04-29 | 2020-09-29 | Shell Internationale Research Maatschappij B.V | Método para melhorar a seletividade de um catalisador de alta seletividade suportado usado na epoxidação de etileno e método para preparar um 1,2-diol, um 1,2-diol éter, um 1,2-carbonato ou uma alcanolamina |
| IN2014DN03028A (https=) * | 2011-10-18 | 2015-05-08 | AHMADI Hassan Eisa AL | |
| CA2858551C (en) * | 2011-12-09 | 2021-10-26 | Dow Technology Investments Llc | Method of maintaining the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst |
| CA2904972C (en) | 2013-03-15 | 2017-10-17 | Dow Technology Investments Llc | Method for the production of ethylene oxide |
| JP6340895B2 (ja) * | 2014-04-24 | 2018-06-13 | 東ソー株式会社 | 触媒性能の経時変化解析方法および触媒性能の経時変化解析装置 |
| CN105330617B (zh) * | 2014-07-18 | 2018-12-28 | 中国石油化工股份有限公司 | 一种生产环氧乙烷的方法 |
| SG11201705409WA (en) * | 2014-12-30 | 2017-07-28 | Dow Technology Investments Llc | Process for manufacturing ethylene oxide using scaled selectivity values |
| EP3495445B1 (en) * | 2016-08-05 | 2023-11-15 | Konoshima Chemical Co., Ltd. | Method for producing al-doped gadolinium oxysulfide cold storage medium |
| CN111450778B (zh) * | 2019-01-22 | 2023-04-07 | 中国石化工程建设有限公司 | 一种用于制备聚α-烯烃的聚合反应系统和方法 |
| CN111939846B (zh) * | 2019-05-17 | 2023-01-03 | 中国石化工程建设有限公司 | 一种合成聚α-烯烃的装置及方法 |
| US11249446B2 (en) | 2019-10-25 | 2022-02-15 | Dow Global Technologies Llc | Nonlinear model predictive control of a process |
| CA3204704A1 (en) | 2020-12-29 | 2022-07-07 | Shell Internationale Research Maatschappij B.V. | Process for the production of ethylene oxide |
| EP4320621A1 (en) | 2021-04-08 | 2024-02-14 | Shell Internationale Research Maatschappij B.V. | Moderator and catalyst performance optimization for epoxidation of ethylene |
| CA3232520A1 (en) * | 2021-09-23 | 2023-03-30 | Wen -Sheng LEE | Process for reducing the aging-related deactivation of high selectivity ethylene oxide catalysts |
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| US20070032670A1 (en) * | 2003-09-29 | 2007-02-08 | Liping Zhang | Process for the production of alkylene oxide using a gas-phase promoter system |
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-
2010
- 2010-04-20 JP JP2012507296A patent/JP2012524785A/ja active Pending
- 2010-04-20 TW TW099112280A patent/TWI508955B/zh active
- 2010-04-20 CA CA2758818A patent/CA2758818C/en not_active Expired - Fee Related
- 2010-04-20 EP EP10718767.6A patent/EP2421840B1/en not_active Revoked
- 2010-04-20 WO PCT/US2010/031668 patent/WO2010123842A1/en not_active Ceased
- 2010-04-20 KR KR1020117027498A patent/KR101745737B1/ko not_active Expired - Fee Related
- 2010-04-20 US US12/763,276 patent/US8389751B2/en not_active Expired - Fee Related
- 2010-04-20 SG SG2011077575A patent/SG175770A1/en unknown
- 2010-04-20 CN CN201080017744.4A patent/CN102414187B/zh active Active
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| US20040198993A1 (en) * | 2003-04-01 | 2004-10-07 | Marek Matusz | Olefin epoxidation process and a catalyst for use in the process |
| US20070032670A1 (en) * | 2003-09-29 | 2007-02-08 | Liping Zhang | Process for the production of alkylene oxide using a gas-phase promoter system |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2758818A1 (en) | 2010-10-28 |
| SG175770A1 (en) | 2011-12-29 |
| US8389751B2 (en) | 2013-03-05 |
| CN102414187B (zh) | 2016-06-01 |
| JP2012524785A (ja) | 2012-10-18 |
| CA2758818C (en) | 2018-05-29 |
| EP2421840B1 (en) | 2015-12-16 |
| EP2421840A1 (en) | 2012-02-29 |
| WO2010123842A1 (en) | 2010-10-28 |
| KR20120014159A (ko) | 2012-02-16 |
| US20100267974A1 (en) | 2010-10-21 |
| KR101745737B1 (ko) | 2017-06-09 |
| CN102414187A (zh) | 2012-04-11 |
| TW201100394A (en) | 2011-01-01 |
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