DE3142626A1 - Elektrochemisches verfahren zur herstellung von 2,5-dialkoxy-2,5-dihydrofuranen - Google Patents
Elektrochemisches verfahren zur herstellung von 2,5-dialkoxy-2,5-dihydrofuranenInfo
- Publication number
- DE3142626A1 DE3142626A1 DE19813142626 DE3142626A DE3142626A1 DE 3142626 A1 DE3142626 A1 DE 3142626A1 DE 19813142626 DE19813142626 DE 19813142626 DE 3142626 A DE3142626 A DE 3142626A DE 3142626 A1 DE3142626 A1 DE 3142626A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydrofuran
- dialkoxy
- graphite
- process according
- electrolysis
- 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- Withdrawn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
- 238000002848 electrochemical method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229910002804 graphite Inorganic materials 0.000 claims description 12
- 239000010439 graphite Substances 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 238000006056 electrooxidation reaction Methods 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 22
- 238000005868 electrolysis reaction Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 8
- 239000003792 electrolyte Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- -1 KF and NaBr Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- LLZQUQVYWCUSAS-UHFFFAOYSA-N 2-methoxy-2,3-dihydrofuran Chemical compound COC1CC=CO1 LLZQUQVYWCUSAS-UHFFFAOYSA-N 0.000 description 2
- SWKVSFPUHCMFJY-UHFFFAOYSA-N 6-methyl-2-oxo-5-pyridin-4-yl-1h-pyridine-3-carboxamide Chemical compound N1C(=O)C(C(N)=O)=CC(C=2C=CN=CC=2)=C1C SWKVSFPUHCMFJY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- PMUKCZSQELAXHR-UHFFFAOYSA-N 4,5-dimethoxy-2,3-dihydrofuran Chemical compound COC1=C(CCO1)OC PMUKCZSQELAXHR-UHFFFAOYSA-N 0.000 description 1
- QKFFSWPNFCXGIQ-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 QKFFSWPNFCXGIQ-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
-
- 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
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)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813142626 DE3142626A1 (de) | 1981-10-28 | 1981-10-28 | Elektrochemisches verfahren zur herstellung von 2,5-dialkoxy-2,5-dihydrofuranen |
| US06/435,037 US4441970A (en) | 1981-10-28 | 1982-10-18 | Electrochemical preparation of 2,5-dialkoxy-2,5-dihydrofurans |
| EP82109666A EP0078004B1 (de) | 1981-10-28 | 1982-10-20 | Elektrochemisches Verfahren zur Herstellung von 2,5-Dialkoxy-2,5-dihydrofuranen |
| DE8282109666T DE3262163D1 (en) | 1981-10-28 | 1982-10-20 | Electrochemical process for the production of 2,5-dialcoxy-2,5-dihydrofurans |
| JP57183800A JPS5877584A (ja) | 1981-10-28 | 1982-10-21 | ２，５−ジアルコキシ−２，５−ジヒドロフランの電気化学的製法 |
| DK475482A DK159330C (da) | 1981-10-28 | 1982-10-27 | Fremgangsmaade til fremstilling af 2,5-dialkoxy-2,5-dihydrofuraner ved elektrokemisk oxidation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813142626 DE3142626A1 (de) | 1981-10-28 | 1981-10-28 | Elektrochemisches verfahren zur herstellung von 2,5-dialkoxy-2,5-dihydrofuranen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3142626A1 true DE3142626A1 (de) | 1983-05-05 |
Family
ID=6144955
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813142626 Withdrawn DE3142626A1 (de) | 1981-10-28 | 1981-10-28 | Elektrochemisches verfahren zur herstellung von 2,5-dialkoxy-2,5-dihydrofuranen |
| DE8282109666T Expired DE3262163D1 (en) | 1981-10-28 | 1982-10-20 | Electrochemical process for the production of 2,5-dialcoxy-2,5-dihydrofurans |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282109666T Expired DE3262163D1 (en) | 1981-10-28 | 1982-10-20 | Electrochemical process for the production of 2,5-dialcoxy-2,5-dihydrofurans |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4441970A (en, 2012) |
| EP (1) | EP0078004B1 (en, 2012) |
| JP (1) | JPS5877584A (en, 2012) |
| DE (2) | DE3142626A1 (en, 2012) |
| DK (1) | DK159330C (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10313169A1 (de) * | 2003-03-25 | 2004-10-14 | Degussa Ag | Verfahren zur anodischen Alkoxylierung von organischen Substraten |
| DE10324192A1 (de) * | 2003-05-28 | 2004-12-23 | Basf Ag | Verfahren zur Herstellung von alkoxylierten 2,5-Dihydrofuran-oder tetra-1,1,4,4-alkoxylierten But-2-enderivaten |
| DE102005013631A1 (de) * | 2005-03-24 | 2006-09-28 | Basf Ag | Verfahren zur Herstellung von alkoxylierten 2,5-Dihydrofuran- oder tetra-1,1,4,4-alkoxylierten But-2-enderivaten |
| KR20150023709A (ko) * | 2012-06-15 | 2015-03-05 | 바스프 에스이 | 친핵체 존재 하의 유기 기판의 애노드 산화 |
| KR102484696B1 (ko) * | 2020-03-25 | 2023-01-05 | 울산과학기술원 | 전기 분해 반응에 의한 디히드로퓨란 유도체의 합성 방법 및 이에 의해 합성된 디히드로퓨란 유도체 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2710420C2 (de) * | 1977-03-10 | 1983-12-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur elektrolytischen Herstellung von 2,5-Dialkoxy-2,5-dihydrofuranen |
-
1981
- 1981-10-28 DE DE19813142626 patent/DE3142626A1/de not_active Withdrawn
-
1982
- 1982-10-18 US US06/435,037 patent/US4441970A/en not_active Expired - Lifetime
- 1982-10-20 DE DE8282109666T patent/DE3262163D1/de not_active Expired
- 1982-10-20 EP EP82109666A patent/EP0078004B1/de not_active Expired
- 1982-10-21 JP JP57183800A patent/JPS5877584A/ja active Granted
- 1982-10-27 DK DK475482A patent/DK159330C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0078004B1 (de) | 1985-01-30 |
| EP0078004A1 (de) | 1983-05-04 |
| DK159330C (da) | 1991-02-25 |
| DK475482A (da) | 1983-04-29 |
| JPS5877584A (ja) | 1983-05-10 |
| DE3262163D1 (en) | 1985-03-14 |
| DK159330B (da) | 1990-10-01 |
| JPH0219195B2 (en, 2012) | 1990-04-27 |
| US4441970A (en) | 1984-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |