EP4151774A1 - Procédé de fabrication d'acide sulfonique de méthane - Google Patents
Procédé de fabrication d'acide sulfonique de méthane Download PDFInfo
- Publication number
- EP4151774A1 EP4151774A1 EP21198115.4A EP21198115A EP4151774A1 EP 4151774 A1 EP4151774 A1 EP 4151774A1 EP 21198115 A EP21198115 A EP 21198115A EP 4151774 A1 EP4151774 A1 EP 4151774A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- msa
- methane
- reaction
- mbs
- current density
- 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.)
- Withdrawn
Links
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title claims abstract description 130
- 229940098779 methanesulfonic acid Drugs 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000008569 process Effects 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 6
- 230000035484 reaction time Effects 0.000 claims description 9
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 8
- 229910003460 diamond Inorganic materials 0.000 claims description 4
- 239000010432 diamond Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract description 24
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 40
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 6
- -1 alkane sulfonic acids Chemical class 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000006277 sulfonation reaction Methods 0.000 description 5
- 238000007306 functionalization reaction Methods 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910002567 K2S2O8 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Images
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
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/042—Electrodes formed of a single material
- C25B11/043—Carbon, e.g. diamond or graphene
-
- 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
- C25B3/23—Oxidation
-
- 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
- C25B3/29—Coupling reactions
Definitions
- the present invention relates to a process for the production of methane sulfonic acid from methane and sulfur trioxide in oleum.
- MSA Due to its unique properties, MSA is already used in some processes and demand is expected to increase further in the near future.
- the numerous advantages of MSA are: strongly acidic without being oxidizing, low vapor pressure and odorless, low toxicological risk, high solubility of its salts, high chemical stability and additionally it is biodegradable. All these characteristics make MSA attractive for use in e.g. the electronics industry for electroplating, for cleaning processes, for metal recycling, or in ionic liquids for a number of other processes.
- methane derivatives are used and then converted in multi-step redox reactions. This is not only unfavorable due to the number of reaction steps but also because side products are generated.
- a more attractive pathway is the direct sulfonation of methane, which is known for more than twenty years.
- the sulfonation usually takes place in oleum and is initiated by a metal peroxo- or peroxosulfate species.
- Methane sulfonic acid in contrast to methyl bisulfate (MBS), is considered a high value-added product and a green acid (for example, non-oxidant, low vapor pressure, bio-degradable, and so on) with uses in the pharma, electronic and cleaning industry.
- Basickes et al. ( Basickes, Hogan, Sen, J. Am . Chem. Soc. 1996, 11, 13111- 13112 ) describe the radical-initiated functionalization of methane and ethane in fuming sulfuric acid. Temperatures of 90°C and above are necessary and the yield of MSA is low.
- Mukhopadhyay and Bell report the direct sulfonation of methane at low pressure to methanesulfonic acid in the presence of potassium peroxydisphosphate as the initiator.
- a temperature of 95°C is chosen and the conversion rate of SO 3 is below 30%.
- WO 2004/041399 A2 and US 7,119,226 B2 both suggest a radical pathway and chain reaction for the production of methane sulfonic acid.
- radical chain reactions usually result in undesirable side products, which even manifest themselves as disturbing inhibitors in the production of alkane sulfonic acids, which may lead to termination of the actual reaction for preparing the alkane sulfonic acid and further to impurities, formation of side products and poor yields based on sulfur trioxide and methane.
- WO 2018/146153 describes a method for the production of alkane sulfonic acids, especially methane sulfonic acid, from alkane, especially methane, in which a carbocation is assumingly formed as intermediate.
- alkane sulfonic acids especially methane sulfonic acid
- the problem is solved by an electrochemical process for the production of methane sulfonic acid (MSA) from methane and sulfur trioxide, wherein methane and fuming sulfuric acid are electrolyzed with at least one electrode as anode, preferably at least one BDD electrode or a resistant electrode made from another anode material such as FTO or Pt/lr, ITO, ATO, lead, stainless steel, gold, and alloys thereof, in a pressurized reactor under a methane pressure in the range of at least 30 bar and at most 200 bar in a temperature range of 50°C to 120°C, preferably for a reaction time range which is adjusted depending on the current density and is preferably more than 2 hours, and the MSA is separated from obtained reaction mixture, for instance by distillation or other suitable separation methods such as column chromatography, fractional freezing, ion chromatography, membrane separation.
- MSA methane sulfonic acid
- the current density at the anode is usually kept between 0.5 mA/cm 2 to 20 mA/cm 2 during current flow and can be varied in the progress of the reaction or even paused for a determined amount of time during the reaction so that times of current flow and current-less times may be changed in intervalls.
- the pressure in the pressurized reactor is preferably kept in the range of 50 to 120 bar.
- the reaction can be carried out at temperatures, where unselective and uncontrolled radical chain reactions do not take place as observed in the prior art where high temperatures are required.
- the inventive process can, for example, efficiently be carried out already at about 50°C or slightly higher.
- substances promoting the decomposition of any initiators to radicals or stabilizing said radicals, as used in the prior art is not required in the inventive process as such initiators are not used in the inventive process.
- no such substances are added in the invention.
- Such substances include metal salts ⁇ e.g., Pt, Hg, Rh). They show detrimental side effects of triggering side reactions, which can be avoided by the present invention.
- the temperature in the pressurized reactor is preferably kept in a temperature range of 50°C to 100°C, and the reaction time in the pressurized reactor is usually kept between 3 and 24 hours, depending on the strength of the current density.
- the reaction mixture in the pressurized reaction vessel is preferably agitated, advantageously with a high-speed stirrer in order to safeguard an intimate contact between the anode, the fuming sulfuric acid and the methane.
- the stirring speed should be in the range of 600 rpm to 1800 rpm.
- any electrode fulfilling these properties such as FTO or Pt/lr, ITO, ATO, lead, stainless steel, gold, and alloys thereof, depending on the actual conditions might also be used
- the electrolyte is fuming sulfuric acid having a concentration of 20 to 30 wt.%. SO 3 .
- concentrations of concentrated sulfuric acid with SO 3 in a concentration up to 45 wt.%, or even higher up to 60 wt.% are also possible.
- MSA concentration increases over time at all the current densities applied in shorter reaction times up to three hours. At reaction times longer than 3 hours, however, the current density will influence the yield significantly. At higher current density, the product as well as intermediate species can be decomposed faster which will lead to a decreased concentration compared to lower current densities. As the current density can also be adapted over the time this is actually an advantage as it gives room to find and tune an optimum setting between reaction kinetics and product or intermediate stability.
- the reaction can also take place if electrolysis and pressurization of the reactor are done in separate steps. After one hour of electrolysis of Oleum the reactor can be pressurized with methane immediately or after stirring without current for a time between 0 and 60 min in between. With increasing pause-time as intermediate stirring the concentration of MSA decreases. This shows that an active species is formed during electrolysis which decomposes slowly.
- the reactor was heated to 70 °C under stirring at 1200 rpm where a pressure of 90 bar was reached, then a current density of 3.125 mA/cm 2 was kept for 18000 seconds. Afterwards the autoclave was placed in an ice bath and cooled down to 25 °C before the pressure was released. The liquid sample was then analyzed by 1 H-NMR using sodium methyl sulfate as an internal standard for quantification. The concentration of MSA was 1.5 M, which is a yield of 24% based on SO 3 . Per every electron passed, 4.7 molecules of MSA were generated. The concentration of by-product methyl bisulfate was 1.4 mM, resulting in a selectivity towards MSA of 99.9%.
- the reactor was heated to 70 °C under stirring at 1200 rpm where a pressure of 90 bar was reached, then a current density of 1.25 mA/cm 2 was kept for 16 hours. Afterwards the autoclave was placed in an ice bath and cooled down to 25 °C before the pressure was released. The liquid sample was then analyzed by 1 H-NMR using sodium methyl sulfate as an internal standard for quantification. The concentration of MSA was 1.9 M, which is a yield of 32% based on SO 3 . Per every electron passed, 4.9 molecules of MSA were generated. The concentration of by-product methyl bisulfate was 55 mM, resulting in a selectivity towards MSA of more than 97%.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21198115.4A EP4151774A1 (fr) | 2021-09-21 | 2021-09-21 | Procédé de fabrication d'acide sulfonique de méthane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21198115.4A EP4151774A1 (fr) | 2021-09-21 | 2021-09-21 | Procédé de fabrication d'acide sulfonique de méthane |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4151774A1 true EP4151774A1 (fr) | 2023-03-22 |
Family
ID=77897505
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP21198115.4A Withdrawn EP4151774A1 (fr) | 2021-09-21 | 2021-09-21 | Procédé de fabrication d'acide sulfonique de méthane |
Country Status (1)
Country | Link |
---|---|
EP (1) | EP4151774A1 (fr) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2493038A (en) | 1946-05-31 | 1950-01-03 | Houdry Process Corp | Reaction of methane with sulfur trioxide |
WO2004041399A2 (fr) | 2002-11-05 | 2004-05-21 | Richards Alan K | Conversion anhydre de methane et d'autres alcanes legers en methanol et d'autres derives au moyen de trajets de radicaux et de reactions en chaine produisant un minimum de dechets |
US20050070614A1 (en) | 2003-06-21 | 2005-03-31 | Richards Alan K. | Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds |
US7119226B2 (en) | 2004-04-20 | 2006-10-10 | The Penn State Research Foundation | Process for the conversion of methane |
US10047020B2 (en) | 2013-11-27 | 2018-08-14 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
WO2018146153A1 (fr) | 2017-02-07 | 2018-08-16 | Grillo-Werke Ag | Procédé de production d'acides alcanesulfoniques |
US20190186026A1 (en) * | 2016-08-11 | 2019-06-20 | Massachusetts Institute Of Technology | Electrochemical oxidation of aliphatic and aromatic compounds |
WO2019212835A2 (fr) * | 2018-03-10 | 2019-11-07 | Richards Alan K | Composés, procédés et équipement pour convertir du gaz méthane en acide méthanesulfonique |
-
2021
- 2021-09-21 EP EP21198115.4A patent/EP4151774A1/fr not_active Withdrawn
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2493038A (en) | 1946-05-31 | 1950-01-03 | Houdry Process Corp | Reaction of methane with sulfur trioxide |
WO2004041399A2 (fr) | 2002-11-05 | 2004-05-21 | Richards Alan K | Conversion anhydre de methane et d'autres alcanes legers en methanol et d'autres derives au moyen de trajets de radicaux et de reactions en chaine produisant un minimum de dechets |
US20050070614A1 (en) | 2003-06-21 | 2005-03-31 | Richards Alan K. | Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds |
US7119226B2 (en) | 2004-04-20 | 2006-10-10 | The Penn State Research Foundation | Process for the conversion of methane |
US10047020B2 (en) | 2013-11-27 | 2018-08-14 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
US20190186026A1 (en) * | 2016-08-11 | 2019-06-20 | Massachusetts Institute Of Technology | Electrochemical oxidation of aliphatic and aromatic compounds |
WO2018146153A1 (fr) | 2017-02-07 | 2018-08-16 | Grillo-Werke Ag | Procédé de production d'acides alcanesulfoniques |
WO2019212835A2 (fr) * | 2018-03-10 | 2019-11-07 | Richards Alan K | Composés, procédés et équipement pour convertir du gaz méthane en acide méthanesulfonique |
Non-Patent Citations (3)
Title |
---|
BASICKESHOGANSEN, J. AM . CHEM. SOC., vol. 11, 1996, pages 13111 - 13112 |
LOBREEBELL, IND. ENG. CHEM . RES., vol. 40, 2001, pages 736 - 742 |
MUKHOPADHYAYBELL, ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 7, 2003, pages 161 - 163 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20200115332A1 (en) | Method for the production of alkane sulfonic acids | |
JP2755327B2 (ja) | α−飽和ケトンの電気化学的合成方法 | |
JP5752237B2 (ja) | アリールアルキル界面活性剤前駆体の電気化学合成 | |
DK152591B (da) | Elektrolytisk reduktion af polychlorpicolinsyre | |
WO2015071371A1 (fr) | Procédé de préparation de peroxyde de bis(alcanesulfonyle) par oxydation | |
US3147203A (en) | Process for the production of carbonyl compounds | |
EP4151774A1 (fr) | Procédé de fabrication d'acide sulfonique de méthane | |
GB2358195A (en) | Electrolytic synthesis of tetramethylammonium hydroxide | |
Babu et al. | A homogeneous redox catalytic process for the paired synthesis of l-cysteine and l-cysteic acid from l-cystine | |
Harwood et al. | Electrochemical reduction of nitrobenzene at controlled potentials | |
Kusakabe et al. | Direct formation of hydrogen peroxide over a palladium catalyst based on water electrolysis | |
US2204476A (en) | Production of hyposulphites | |
Kosheleva et al. | Nonanol-1 oxidation on nickel oxide electrode with the involvement of active oxygen forms | |
Kennedy et al. | Thermally coated Ti/TiO 2 as cathode material for the synthesis of succinic and dihydrophthalic acids | |
US1354451A (en) | Manufacture of reducing alkaline melts | |
Loyson et al. | Kinetic aspects of the direct electrochemical oxidation of p-xylene in methanol using graphite electrodes | |
SU1685907A1 (ru) | Способ получени аминопропанонов | |
Folgueiras Amador | Design and manufacture of an electrochemical flow reactor, and its application in organic electrosynthesis | |
US10590546B2 (en) | Catalytic or electrocatalytic generation of chlorine dioxide | |
US3419483A (en) | Two stage electrolytic and chemical process for alpha-olefin conversion to aliphaticacids | |
US4014762A (en) | Process for the preparation of hexafluoropropene epoxide | |
Neverov et al. | Electrosynthesis of cyclopropanes at the electrolysis of solutions of methyl esters of Di-and trichloroacetatic acids in aprotic media in the presence of acrylonitrile | |
CN117051414A (zh) | 一种电化学合成芳香基磺酰氟化合物的方法 | |
KR20220032589A (ko) | 메탄 술폰산 및 so3 를 포함하는 반응 혼합물 중의 so3 농도 감소 방법 | |
RU2361966C2 (ru) | Способ проведения электролиза водного раствора соли |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN PUBLISHED |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20230923 |