CN113668002B - Method for preparing acetone by using formic acid - Google Patents
Method for preparing acetone by using formic acid Download PDFInfo
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- CN113668002B CN113668002B CN202110930397.4A CN202110930397A CN113668002B CN 113668002 B CN113668002 B CN 113668002B CN 202110930397 A CN202110930397 A CN 202110930397A CN 113668002 B CN113668002 B CN 113668002B
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- formic acid
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 75
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 235000019253 formic acid Nutrition 0.000 title claims abstract description 29
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 11
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical group Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 239000003792 electrolyte Substances 0.000 claims abstract description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 22
- 239000000047 product Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 238000002848 electrochemical method Methods 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
The invention discloses a method for preparing acetone by formic acid, which is 0.1-0.7 mol.L ‑1 Formic acid solution as electrolyte, metal lead sheet as cathode, inert material as anode, inThe cathode electrolytic voltage relative to the saturated calomel electrode is-1.4 to-1.7V vs.SCE Carrying out electrolysis; the method electrochemically reduces formic acid into acetone and ethanol, has the characteristics of simple equipment, small occupied area, simple process, convenient operation and the like, and has better theoretical and practical significance in preparing C3 organic matters from C1 organic matters.
Description
Technical Field
The invention relates to the technical field of organic chemical preparation, in particular to an electrochemical method for preparing acetone by formic acid.
Background
Formic acid, also known as formic acid, has the molecular formula HCOOH. Formic acid is colorless and smelly liquid, is an important basic chemical raw material, is an intermediate of chemical reaction and a renewable energy carrier, and is widely applied to industries such as pesticides, leather, dyes, medicines, rubber and the like. Formic acid is a C1 organic substance, the preparation method is relatively simple and easy, and the industrial preparation mainly comprises a sodium formate method, a methanol oxo synthesis method (also called a methyl formate method), a formamide method and the like.
Acetone, also known as dimethyl ketone, of the formula CH 3 COCH 3 The simplest saturated ketone is a colorless transparent liquid with a special pungent smell. It is easily dissolved in water and organic solvents such as methanol, ethanol, ether, chloroform, pyridine, etc., and is flammable, volatile and active in chemical property. Acetone is a C3 organic matter, is an important organic synthetic raw material, is used for producing epoxy resin, polycarbonate, organic glass, medicines, pesticides and the like, is an important raw material for producing acetic anhydride, diacetone alcohol, chloroform, iodoform, epoxy resin, polyisoprene rubber, methyl methacrylate and the like, and is also an excellent solvent, a diluent, a cleaning agent, an extracting agent and the like. The production method of acetone mainly comprises a cumene method, an isopropanol method, a fermentation method, an acetylene hydration method, a propylene direct oxidation method and the like, and at present, the industrial production of acetone mainly comprises the cumene method.
The electrochemical method has the advantages of simple equipment, small occupied area, normal operation at room temperature, convenient operation, changeable production scale, few byproducts, high product selectivity and the like, and is widely applied to organic chemical industry, but at present, no method for preparing acetone by the electrochemical method by taking formic acid as a substrate reactant exists.
Disclosure of Invention
In order to solve the defects in the prior art, the inventor provides an electrochemical method for preparing acetone by formic acid, and the electrochemical method has the characteristics of simple process, convenient operation and high selectivity of acetone and ethanol products.
Specifically, the invention provides a method for preparing acetone by using formic acid, which takes the formic acid as a substrate reactant and prepares the acetone by an electrochemical method, the formic acid is electrochemically reduced into acetone and/or ethanol, and the reaction generated by a cathode is as follows:
3HCOOH+10H + +10e - →CH 3 COCH 3 +5H 2 O。
in the range of 0.1 to 0.7 mol.L -1 The formic acid solution is taken as electrolyte, the metal lead sheet is taken as cathode, the inert material is taken as anode, and the cathode electrolysis voltage relative to the saturated calomel electrode is-1.4 to-1.7V vs.SCE Electrolysis is carried out. Wherein, the sizes of the cathode and the anode are determined according to actual requirements.
Further, the inert material is a metal platinum sheet or a graphite plate.
The invention provides a method for preparing acetone by an electrochemical method by taking formic acid as a substrate reactant, which electrochemically reduces the formic acid into acetone and ethanol, and every 3mol of formic acid can react to generate 1mol of acetone, so that the method has the advantages of simple process, convenient operation and small occupied area, and has better theoretical and practical significance in the aspect of preparing C3 organic matters from C1 organic matters.
Detailed Description
The present invention will be described in further detail by way of examples.
Example 1
0.1 mol.L is added into a 150mL electrolytic cell -1 100mL of HCOOH solution, a lead sheet with the thickness of 3cm multiplied by 4cm is taken as a cathode, a platinum sheet with the thickness of 3cm multiplied by 4cm is taken as an anode, a saturated calomel electrode is taken as a reference electrode, and the electrolytic voltage at the cathode is minus 1.6V vs.SCE After electrolysis for 10 hours, the faradic efficiency of the product acetone is 5.47 percent, and no byproduct ethanol exists.
Example 2
0.3 mol.L is added into a 150mL electrolytic cell -1 HCOOH solution100mL of the solution, 3cm × 4cm lead sheet as a cathode, 3cm × 4cm platinum sheet as an anode, saturated calomel electrode as a reference electrode, and electrolytic voltage of-1.6V at the cathode vs.SCE After electrolysis for 10 hours, the faradaic efficiency of the acetone product is 9.60 percent, and the faradaic efficiency of the ethanol byproduct is 0.90 percent.
Example 3
0.7 mol.L is added into a 150mL electrolytic cell -1 100mL of HCOOH solution, a lead sheet of 3cm × 4cm as a cathode, a platinum sheet of 3cm × 4cm as an anode, and a saturated calomel electrode as a reference electrode. Electrolytic voltage at cathode is-1.6V vs.SCE After electrolysis for 10 hours, the faradaic efficiency of the acetone product is 2.18 percent, and the faradaic efficiency of the ethanol byproduct is 2.12 percent.
Example 4
0.3 mol.L is added into a 150mL electrolytic cell -1 100mL of HCOOH solution, a lead sheet of 3cm × 4cm as a cathode, a platinum sheet of 3cm × 4cm as an anode, and a saturated calomel electrode as a reference electrode. Electrolytic voltage at cathode-1.4V vs.SCE After 10 hours of electrolysis, the faradaic efficiency of the product acetone is 4.77 percent, and the faradaic efficiency of the byproduct ethanol is 1.80 percent.
Example 5
0.3 mol.L is added into a 150mL electrolytic cell -1 100mL of HCOOH solution, a lead sheet of 3cm × 4cm as a cathode, a platinum sheet of 3cm × 4cm as an anode, and a saturated calomel electrode as a reference electrode. Electrolytic voltage at cathode-1.7V vs.SCE After 10 hours of electrolysis, the faradaic efficiency of the product acetone is 2.55 percent, and the faradaic efficiency of the byproduct ethanol is 0.18 percent.
Example 6
0.3 mol.L is added into a 150mL electrolytic cell -1 100mL of HCOOH solution, a lead sheet of 3cm × 4cm as a cathode, a platinum sheet of 3cm × 4cm as an anode, and a saturated calomel electrode as a reference electrode. Electrolytic voltage at cathode-1.6V vs.SCE After 7 hours of electrolysis, the faradaic efficiency of the product acetone is 7.36 percent, and the faradaic efficiency of the byproduct ethanol is 2.74 percent.
Claims (2)
1. A process for preparing acetone from formic acid features that the solution is prepared from 0.1-0.7 mol of 8729L -1 The formic acid solution is taken as electrolyte, the metal lead sheet is taken as cathode, the inert material is taken as anode, and the cathode electrolysis voltage relative to the saturated calomel electrode is-1.4 to-1.7V vs.SCE The electrolysis is carried out to electrochemically reduce formic acid to acetone, and the reaction at the cathode is as follows:
3HCOOH+10H + +10e - →CH 3 COCH 3 +5H 2 O。
2. the method of claim 1, wherein the inert material is a metallic platinum sheet or a graphite plate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110930397.4A CN113668002B (en) | 2021-08-13 | 2021-08-13 | Method for preparing acetone by using formic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110930397.4A CN113668002B (en) | 2021-08-13 | 2021-08-13 | Method for preparing acetone by using formic acid |
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| Publication Number | Publication Date |
|---|---|
| CN113668002A CN113668002A (en) | 2021-11-19 |
| CN113668002B true CN113668002B (en) | 2023-04-11 |
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Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6332732B2 (en) * | 2014-02-07 | 2018-05-30 | 日立化成株式会社 | Electrode, electrode manufacturing method, electrochemical reduction method, and electrochemical reduction product manufacturing method |
| CN106498437B (en) * | 2015-09-07 | 2019-06-11 | 中国科学院大连化学物理研究所 | A kind of Carbon dioxide electrochemical reduction electrode preparation method |
| CN111254456B (en) * | 2020-03-31 | 2021-04-09 | 青岛科技大学 | Electrochemical synthesis method of 2-nitro-4-methylsulfonylbenzoic acid |
| CN112760674B (en) * | 2020-12-24 | 2022-07-22 | 山东师范大学 | System and method for synthesizing ammonia and acetone in one step by electrochemical reduction at normal temperature and normal pressure |
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| CN113668002A (en) | 2021-11-19 |
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