TWI455920B - 用於乙酸及／或乙酸甲酯之生產的羰基化方法 - Google Patents
用於乙酸及／或乙酸甲酯之生產的羰基化方法 Download PDFInfo
- Publication number
- TWI455920B TWI455920B TW097147817A TW97147817A TWI455920B TW I455920 B TWI455920 B TW I455920B TW 097147817 A TW097147817 A TW 097147817A TW 97147817 A TW97147817 A TW 97147817A TW I455920 B TWI455920 B TW I455920B
- Authority
- TW
- Taiwan
- Prior art keywords
- microns
- range
- zeolite
- micron
- average particle
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims 6
- 230000006315 carbonylation Effects 0.000 title claims 3
- 238000005810 carbonylation reaction Methods 0.000 title claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 title claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 6
- 239000010457 zeolite Substances 0.000 claims 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 4
- 239000002245 particle Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 229910052680 mordenite Inorganic materials 0.000 claims 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 229910000420 cerium oxide Inorganic materials 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
- B01J29/20—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type containing iron group metals, noble metals or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/37—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by reaction of ethers with carbon monoxide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Claims (13)
- 一種用於製造乙酸及乙酸甲酯中之至少一者之方法，該方法包含在結構類型MOR之沸石的存在下，使用一氧化碳羰基化選自於甲醇、二甲醚及碳酸二甲酯中之至少一種可羰基化反應物的步驟，其中該沸石具有大於50%其晶粒係於0.1微米至3微米之大小範圍。
- 如申請專利範圍第1項之方法，其中大於50%晶粒係於0.1微米至2微米之大小範圍。
- 如申請專利範圍第2項之方法，其中大於50%晶粒係於0.1微米至1.5微米之大小範圍。
- 如申請專利範圍第1項之方法，其中大於80%晶粒係於0.1微米至2微米之大小範圍。
- 如申請專利範圍第1項之方法，其中該沸石具有平均粒徑係不大於6微米。
- 如申請專利範圍第5項之方法，其中平均粒徑係於2微米至3.5微米之範圍。
- 如申請專利範圍第2項之方法，且其中平均粒徑係於2微米至6微米之範圍。
- 如申請專利範圍第3項之方法，且其中平均粒徑係於2微米至3.5微米之範圍。
- 如申請專利範圍第1項之方法，其中該沸石為H-絲光沸石。
- 如申請專利範圍第1項之方法，其中該沸石為已經過離 子交換之絲光沸石，或者是載荷有選自於銅、銀、金、鎳、銥、銠、鉑、鈀及鈷中之一種或多種金屬之絲光沸石。
- 如申請專利範圍第1項之方法，其中該沸石具有於10至40：1之氧化矽：氧化鋁比。
- 如申請專利範圍第1項之方法，其中該羰基化反應物為二甲醚或碳酸二甲酯及該方法的該氣體進料具有低於2.5wt%水。
- 如申請專利範圍第1項之方法，其中該羰基化係於氫存在下進行。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07254975A EP2085375A1 (en) | 2007-12-20 | 2007-12-20 | Process for the production of acetic acid and/or methyl acetate in the presence of a zeolite of structure type MOR |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200936557A TW200936557A (en) | 2009-09-01 |
| TWI455920B true TWI455920B (zh) | 2014-10-11 |
Family
ID=39365837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097147817A TWI455920B (zh) | 2007-12-20 | 2008-12-09 | 用於乙酸及／或乙酸甲酯之生產的羰基化方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8426633B2 (zh) |
| EP (2) | EP2085375A1 (zh) |
| CN (2) | CN105646178B (zh) |
| TW (1) | TWI455920B (zh) |
| WO (1) | WO2009081099A1 (zh) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2199272A1 (en) * | 2008-11-27 | 2010-06-23 | BP Chemicals Limited | Carbonylation process |
| EP2251314A1 (en) * | 2009-05-14 | 2010-11-17 | BP Chemicals Limited | Carbonylation process |
| CA2809440C (en) * | 2010-08-27 | 2018-01-23 | Technical University Of Denmark | Mordenite - type zeolite scr catalysts with iron or copper |
| WO2013012814A2 (en) * | 2011-07-16 | 2013-01-24 | President And Fellows Of Harvard College | Gold-catalyzed synthesis of carbonates and carbamates from carbon monoxide |
| US8927762B2 (en) * | 2011-11-16 | 2015-01-06 | Enerkem, Inc. | Production of oxygenated compounds from carbon monoxide and dimethyl carbonate |
| US20130158290A1 (en) * | 2011-11-22 | 2013-06-20 | Stephane MARIE-ROSE | Production of oxygenated compounds in the presence of a catalyst suspended in an inert liquid |
| CN104725229B (zh) * | 2013-12-23 | 2017-05-31 | 中国科学院大连化学物理研究所 | 制备聚甲氧基二甲醚羰化物及甲氧基乙酸甲酯的方法 |
| CN106365995B (zh) * | 2015-07-20 | 2018-06-05 | 中国科学院大连化学物理研究所 | 一种乙酸甲酯的生产方法 |
| CN106365994B (zh) | 2015-07-20 | 2019-01-01 | 中国科学院大连化学物理研究所 | 一种低级脂肪羧酸烷基酯的生产方法 |
| CN106518657B (zh) | 2015-09-11 | 2019-03-29 | 中国科学院大连化学物理研究所 | 一种通过甲醇羰基化制备乙酸的方法 |
| CN106890669B (zh) * | 2015-12-18 | 2019-04-02 | 中国科学院大连化学物理研究所 | 一种生产乙酸甲酯的催化剂、其制备方法及应用 |
| CN106890665B (zh) * | 2015-12-18 | 2020-06-09 | 中国科学院大连化学物理研究所 | 一种二甲醚羰基化生产乙酸甲酯的催化剂及其应用 |
| CN106316846B (zh) * | 2016-08-26 | 2018-12-25 | 西南化工研究设计院有限公司 | 一种乙酸甲酯的生产方法 |
| CN108579794A (zh) * | 2018-04-02 | 2018-09-28 | 新疆大学 | 负载金的分子筛催化剂用于转化甲醇为乙酸甲酯的方法 |
| CN111822041B (zh) * | 2019-04-15 | 2021-11-09 | 中国科学院大连化学物理研究所 | 一种复合催化剂、其制备方法及其应用 |
| CN114433188B (zh) * | 2020-10-19 | 2024-01-26 | 中国石油化工股份有限公司 | 一种乙酸甲酯催化剂及其制备方法和乙酸甲酯的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007128955A1 (en) * | 2006-04-12 | 2007-11-15 | Bp Chemicals Limited | Process for the preparation of carbonylation products |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3760062A (en) * | 1971-10-26 | 1973-09-18 | Zeochem Corp | Synthetic zeolite |
| US4205052A (en) | 1979-02-01 | 1980-05-27 | Mobil Oil Corporation | Manufacture of synthetic mordenite |
| DE3212106A1 (de) | 1981-11-21 | 1983-06-01 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von grobkoernigem mordenit |
| US4612387A (en) * | 1982-01-04 | 1986-09-16 | Air Products And Chemicals, Inc. | Production of carboxylic acids and esters |
| GB9223170D0 (en) | 1992-11-05 | 1992-12-16 | British Petroleum Co Plc | Process for preparing carboxylic acids |
| US6127432A (en) * | 1998-01-29 | 2000-10-03 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for preparing oxygenates and catalysts therefor |
| GB0409490D0 (en) | 2004-04-28 | 2004-06-02 | Bp Chem Int Ltd | Process |
| US20060252959A1 (en) | 2005-05-05 | 2006-11-09 | The Regents Of The University Of California | Process for carbonylation of alkyl ethers |
| US7465822B2 (en) * | 2005-05-05 | 2008-12-16 | Bp Chemicals Ltd. | Process for carbonylation of alkyl ethers |
-
2007
- 2007-12-20 EP EP07254975A patent/EP2085375A1/en not_active Ceased
-
2008
- 2008-12-09 TW TW097147817A patent/TWI455920B/zh not_active IP Right Cessation
- 2008-12-16 EP EP08864514.8A patent/EP2231579B1/en not_active Not-in-force
- 2008-12-16 CN CN201610084596.7A patent/CN105646178B/zh active Active
- 2008-12-16 WO PCT/GB2008/004136 patent/WO2009081099A1/en active Application Filing
- 2008-12-16 CN CN2008801214814A patent/CN101903325A/zh active Pending
- 2008-12-16 US US12/735,180 patent/US8426633B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007128955A1 (en) * | 2006-04-12 | 2007-11-15 | Bp Chemicals Limited | Process for the preparation of carbonylation products |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101903325A (zh) | 2010-12-01 |
| CN105646178A (zh) | 2016-06-08 |
| US20100267985A1 (en) | 2010-10-21 |
| EP2085375A1 (en) | 2009-08-05 |
| US8426633B2 (en) | 2013-04-23 |
| TW200936557A (en) | 2009-09-01 |
| WO2009081099A1 (en) | 2009-07-02 |
| EP2231579A1 (en) | 2010-09-29 |
| EP2231579B1 (en) | 2015-11-04 |
| CN105646178B (zh) | 2019-07-12 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |