DE2753634C3 - Verfahren zur Herstellung von Methylformiat - Google Patents
Verfahren zur Herstellung von MethylformiatInfo
- Publication number
- DE2753634C3 DE2753634C3 DE2753634A DE2753634A DE2753634C3 DE 2753634 C3 DE2753634 C3 DE 2753634C3 DE 2753634 A DE2753634 A DE 2753634A DE 2753634 A DE2753634 A DE 2753634A DE 2753634 C3 DE2753634 C3 DE 2753634C3
- Authority
- DE
- Germany
- Prior art keywords
- copper
- zinc
- zirconium
- catalyst
- methyl formate
- 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
Links
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 39
- 239000011701 zinc Substances 0.000 claims description 28
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 26
- 239000010949 copper Substances 0.000 claims description 26
- 229910052725 zinc Inorganic materials 0.000 claims description 26
- 229910052802 copper Inorganic materials 0.000 claims description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 22
- 229910052726 zirconium Inorganic materials 0.000 claims description 17
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 16
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229940116318 copper carbonate Drugs 0.000 claims description 8
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- -1 aluminum compound Chemical class 0.000 claims description 3
- 239000012808 vapor phase Substances 0.000 claims description 3
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 claims description 2
- 229910052845 zircon Inorganic materials 0.000 claims description 2
- 238000010304 firing Methods 0.000 claims 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- CTHCNINEXYPGQP-UHFFFAOYSA-N [Zn].[Cu].[Zr] Chemical compound [Zn].[Cu].[Zr] CTHCNINEXYPGQP-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- JRBRVDCKNXZZGH-UHFFFAOYSA-N alumane;copper Chemical compound [AlH3].[Cu] JRBRVDCKNXZZGH-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/40—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of primary alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14489976A JPS5371008A (en) | 1976-12-02 | 1976-12-02 | Preparation of methyl formate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2753634A1 DE2753634A1 (de) | 1978-06-08 |
| DE2753634B2 DE2753634B2 (de) | 1979-10-18 |
| DE2753634C3 true DE2753634C3 (de) | 1980-06-26 |
Family
ID=15372900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2753634A Expired DE2753634C3 (de) | 1976-12-02 | 1977-12-01 | Verfahren zur Herstellung von Methylformiat |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4149009A (enExample) |
| JP (1) | JPS5371008A (enExample) |
| BE (1) | BE879915Q (enExample) |
| DE (1) | DE2753634C3 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4480122A (en) * | 1982-09-27 | 1984-10-30 | Celanese Corporation | Process for producing methyl formate |
| JPS60106534A (ja) * | 1983-11-14 | 1985-06-12 | Mitsubishi Gas Chem Co Inc | メタノ−ル合成用流動触媒 |
| JPS6165840A (ja) * | 1984-09-07 | 1986-04-04 | Nippon Shokubai Kagaku Kogyo Co Ltd | ジグリコ−ル酸塩の製造方法 |
| GB8501319D0 (en) * | 1985-01-18 | 1985-02-20 | Bp Chem Int Ltd | Production of methyl formate |
| US4939292A (en) * | 1985-08-01 | 1990-07-03 | Phillips Petroleum Company | Synthesis of esters from alcohols containing carbon monoxide as an impurity |
| DE3936854A1 (de) * | 1989-11-06 | 1991-05-08 | Basf Ag | Verfahren zur herstellung von methylformiat |
| US5395989A (en) * | 1990-11-06 | 1995-03-07 | Mitsubishi Gas Chemical Company, Inc. | Process for producing neopentyl glycol |
| DE4309731A1 (de) * | 1993-03-25 | 1994-09-29 | Basf Ag | Verfahren zur Herstellung von Methylformiat |
| JP3358631B2 (ja) * | 1993-05-17 | 2002-12-24 | 三菱瓦斯化学株式会社 | メタノ−ルの脱水素方法 |
| WO1997003937A1 (de) * | 1995-07-21 | 1997-02-06 | Lonza A.G. | Verfahren zur herstellung von methanol und katalysator dafür |
| AU2938700A (en) * | 1999-03-08 | 2000-09-28 | Chisso Corporation | Catalyst for ester production and process for producing ester |
| RU2185370C1 (ru) * | 2000-12-04 | 2002-07-20 | Институт катализа им.Г.К.Борескова СО РАН | Способ получения метилформиата, катализатор для его осуществления и способ получения катализатора |
| US20050027195A1 (en) * | 2003-08-01 | 2005-02-03 | Assaf Govari | Calibration data compression |
| US20050059839A1 (en) * | 2003-09-15 | 2005-03-17 | The Regents Of The University Of California | Process and catalysts for the oxidation of methanol and/or ethanol |
| US6956134B2 (en) * | 2004-01-08 | 2005-10-18 | The Regents Of The University Of California | Oxidation of methanol and/or dimethyl ether using supported molybdenum-containing heteropolyacid catalysts |
| US20100130758A1 (en) * | 2007-03-09 | 2010-05-27 | Kiyotomi Kaneda | Method for producing carbonyl compound |
| JP5376114B2 (ja) | 2008-09-26 | 2013-12-25 | 三菱瓦斯化学株式会社 | 蟻酸メチル製造用メタノール脱水素触媒および蟻酸メチル製造方法 |
| CN104066506B (zh) * | 2011-11-21 | 2016-09-07 | 巴斯夫公司 | 铜-氧化锆催化剂及使用和制造方法 |
| CN105859555B (zh) * | 2016-04-14 | 2019-05-31 | 江苏大学 | 一种甲醇常压下脱氢制备甲酸甲酯的方法 |
| CN107159217A (zh) * | 2017-04-25 | 2017-09-15 | 江苏大学 | 一种Cu‑ZnO/SiO2气凝胶双金属催化剂及其制备方法和用途 |
| US10544077B2 (en) | 2017-08-02 | 2020-01-28 | Eastman Chemical Company | Process for making formic acid utilizing higher-boiling formate esters |
| US10570081B2 (en) | 2017-08-02 | 2020-02-25 | Eastman Chemical Company | Process for making formic acid utilizing lower-boiling formate esters |
| US10266466B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Iron-catalyzed transfer hydrogenation of esters to alcohols |
| US10435349B2 (en) | 2017-08-02 | 2019-10-08 | Eastman Chemical Company | Iron-catalyzed cross-coupling of methanol with secondary or tertiary alcohols to produce formate esters |
| US10266467B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Synthesis of glycols via transfer hydrogenation of alpha-functional esters with alcohols |
| CN111774070B9 (zh) * | 2020-07-13 | 2023-09-29 | 陕西延长石油（集团）有限责任公司 | 一种催化甲醇脱氢制备甲酸甲酯的催化剂及其制备方法与应用 |
| CN116899582B (zh) * | 2023-09-04 | 2024-11-01 | 中国石油大学(华东) | 一种用于混合醇脱氢的铜负载二氧化硅催化剂的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2522676A (en) * | 1947-06-19 | 1950-09-19 | Socony Vacuum Oil Co Inc | Dehydrogenation of alcohols with sulfur |
| US3188330A (en) * | 1961-07-12 | 1965-06-08 | Argus Chem | Process for preparing esters and ketones from alcohols |
-
1976
- 1976-12-02 JP JP14489976A patent/JPS5371008A/ja active Granted
-
1977
- 1977-11-21 US US05/853,234 patent/US4149009A/en not_active Expired - Lifetime
- 1977-12-01 DE DE2753634A patent/DE2753634C3/de not_active Expired
-
1979
- 1979-11-08 BE BE0/198036A patent/BE879915Q/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5346821B2 (enExample) | 1978-12-16 |
| JPS5371008A (en) | 1978-06-24 |
| US4149009A (en) | 1979-04-10 |
| DE2753634A1 (de) | 1978-06-08 |
| DE2753634B2 (de) | 1979-10-18 |
| BE879915Q (fr) | 1980-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. KERN, R., DIPL.-ING. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |