DE2248562A1 - Verfahren zur herstellung von dicarbonsaeurediestern durch elektrochemische kondensation von dicarbonsaeuremonoestern - Google Patents
Verfahren zur herstellung von dicarbonsaeurediestern durch elektrochemische kondensation von dicarbonsaeuremonoesternInfo
- Publication number
- DE2248562A1 DE2248562A1 DE19722248562 DE2248562A DE2248562A1 DE 2248562 A1 DE2248562 A1 DE 2248562A1 DE 19722248562 DE19722248562 DE 19722248562 DE 2248562 A DE2248562 A DE 2248562A DE 2248562 A1 DE2248562 A1 DE 2248562A1
- Authority
- DE
- Germany
- Prior art keywords
- monoesters
- dicarbonic
- water
- production
- electrochemical
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000009833 condensation Methods 0.000 title claims description 7
- 230000005494 condensation Effects 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 DICARBONIC ACID DIESTERS Chemical class 0.000 title description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000005868 electrolysis reaction Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000003792 electrolyte Substances 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000006612 Kolbe reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910002835 Pt–Ir Inorganic materials 0.000 description 1
- 229910018885 Pt—Au Inorganic materials 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N Suberic acid Natural products OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229940014772 dimethyl sebacate Drugs 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C25B3/20—Processes
- C25B3/29—Coupling reactions
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 (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722248562 DE2248562A1 (de) | 1972-10-04 | 1972-10-04 | Verfahren zur herstellung von dicarbonsaeurediestern durch elektrochemische kondensation von dicarbonsaeuremonoestern |
| NL7312464A NL7312464A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-04 | 1973-09-10 | |
| IT29130/73A IT998637B (it) | 1972-10-04 | 1973-09-19 | Processo per la preparazione di diesteri di acidi dicarbossilici mediante condensazione elettrochi mica di monoesteri di acidi dicarbossilici |
| BE135987A BE805251A (fr) | 1972-10-04 | 1973-09-25 | Procede de preparation de diesters d'acides dicarboxyliques par condensation electrochimique de monoesters d'acides dicarboxyliques |
| FR7335135A FR2202059B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-04 | 1973-10-02 | |
| CA182,490A CA1029329A (en) | 1972-10-04 | 1973-10-02 | Production of diesters of dicarboxylic acids |
| GB4620173A GB1438335A (en) | 1972-10-04 | 1973-10-03 | Production of diesters of dicarboxylic acids by electrochemical condensation of 'onoesters of dicarboxylic acids |
| JP48110606A JPS4975518A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-04 | 1973-10-03 | |
| US403614A US3879271A (en) | 1972-10-04 | 1973-10-04 | Production of diesters of dicarboxylic acids by electrochemical condensation of monoesters of dicarboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722248562 DE2248562A1 (de) | 1972-10-04 | 1972-10-04 | Verfahren zur herstellung von dicarbonsaeurediestern durch elektrochemische kondensation von dicarbonsaeuremonoestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2248562A1 true DE2248562A1 (de) | 1974-04-11 |
Family
ID=5858111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722248562 Pending DE2248562A1 (de) | 1972-10-04 | 1972-10-04 | Verfahren zur herstellung von dicarbonsaeurediestern durch elektrochemische kondensation von dicarbonsaeuremonoestern |
Country Status (9)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1081830B (it) * | 1976-06-10 | 1985-05-21 | Battelle Memorial Institute | Procedimento di trasferimento di idrogeno in continuo mediante un idruro metallico fra un mezzo liquido acquoso e un composto organico da idrogenare o da deidrogenare |
| US4097344A (en) * | 1976-06-29 | 1978-06-27 | E. I. Du Pont De Nemours And Company | Electrochemical coupling of perfluoroalkyl iodides |
| JPS5422317A (en) * | 1977-07-20 | 1979-02-20 | Asahi Chem Ind Co Ltd | Electrolitic preparation of sebacic acid dimethyl ester |
| EP0097719B1 (en) * | 1982-01-12 | 1987-06-03 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing higher dibasic acid dimethyl ester |
| ATA134894A (de) * | 1994-07-08 | 1997-12-15 | Hafslund Nycomed Pharma | Verfahren zur herstellung substituierter diaminodicarbonsäurederivate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB313717I5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-09-17 | |||
| DE1643693B2 (de) * | 1967-11-11 | 1976-09-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von sebacinsaeuredimethylester durch elektrolytische kondensation von adipinsaeuremonomethylester |
| US3589990A (en) * | 1968-02-29 | 1971-06-29 | Vnii Pi Monomerov | Process for the production of sebacic acid |
| DE2014985C3 (de) * | 1970-03-28 | 1978-06-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur elektrolytischen Kondensation von Carbonsäuren |
-
1972
- 1972-10-04 DE DE19722248562 patent/DE2248562A1/de active Pending
-
1973
- 1973-09-10 NL NL7312464A patent/NL7312464A/xx unknown
- 1973-09-19 IT IT29130/73A patent/IT998637B/it active
- 1973-09-25 BE BE135987A patent/BE805251A/xx unknown
- 1973-10-02 CA CA182,490A patent/CA1029329A/en not_active Expired
- 1973-10-02 FR FR7335135A patent/FR2202059B1/fr not_active Expired
- 1973-10-03 GB GB4620173A patent/GB1438335A/en not_active Expired
- 1973-10-03 JP JP48110606A patent/JPS4975518A/ja active Pending
- 1973-10-04 US US403614A patent/US3879271A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2202059A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-03 |
| NL7312464A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-08 |
| CA1029329A (en) | 1978-04-11 |
| GB1438335A (en) | 1976-06-03 |
| BE805251A (fr) | 1974-03-25 |
| US3879271A (en) | 1975-04-22 |
| FR2202059B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-12 |
| JPS4975518A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-20 |
| IT998637B (it) | 1976-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |