EP1348043A2 - Procede de production de liaisons carbonyle alcoxylees par oxydation anodique et reaction de couplage cathodique pour realiser une synthese organique - Google Patents

Procede de production de liaisons carbonyle alcoxylees par oxydation anodique et reaction de couplage cathodique pour realiser une synthese organique

Info

Publication number: EP1348043A2
Authority: EP; European Patent Office
Prior art keywords: compounds; derivatives; alkyl; acid; substituted
Prior art date: 2000-11-24
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.): Granted

Application number

EP01994702A

Other languages

German (de)

English (en)

Other versions

EP1348043B1 (fr

Inventor

Hermann Pütter

Andreas Fischer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

2000-11-24

Filing date

2001-11-22

Publication date

2003-10-01

2001-11-22 Application filed by BASF SE filed Critical BASF SE

2003-10-01 Publication of EP1348043A2 publication Critical patent/EP1348043A2/fr

2005-03-09 Application granted granted Critical

2005-03-09 Publication of EP1348043B1 publication Critical patent/EP1348043B1/fr

2021-11-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000003647 oxidation Effects 0.000 title claims abstract description 11
238000007254 oxidation reaction Methods 0.000 title claims abstract description 11
150000001728 carbonyl compounds Chemical class 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title abstract description 7
238000005859 coupling reaction Methods 0.000 title description 3
238000003786 synthesis reaction Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 38
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims abstract 3
238000005868 electrolysis reaction Methods 0.000 claims description 14
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 9
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000005907 alkyl ester group Chemical group 0.000 claims description 6
-1 aromatic carboxylic acids Chemical class 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 claims description 6
150000002894 organic compounds Chemical class 0.000 claims description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
150000001241 acetals Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
150000002790 naphthalenes Chemical class 0.000 claims description 4
150000003021 phthalic acid derivatives Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Chemical class OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 3
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 3
GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 claims description 2
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
HULHOBUIBFPLGZ-UHFFFAOYSA-N benzene-1,2,3-tricarbaldehyde Chemical class O=CC1=CC=CC(C=O)=C1C=O HULHOBUIBFPLGZ-UHFFFAOYSA-N 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
150000003628 tricarboxylic acids Chemical class 0.000 claims description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 2
238000007080 aromatic substitution reaction Methods 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
150000002466 imines Chemical class 0.000 claims 1
150000002689 maleic acids Chemical class 0.000 claims 1
230000028161 membrane depolarization Effects 0.000 claims 1
239000003792 electrolyte Substances 0.000 abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
238000006056 electrooxidation reaction Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 9
239000000243 solution Substances 0.000 description 8
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
229910002804 graphite Inorganic materials 0.000 description 6
FIMHASWLGDDANN-UHFFFAOYSA-M methyl sulfate;tributyl(methyl)azanium Chemical compound COS([O-])(=O)=O.CCCC[N+](C)(CCCC)CCCC FIMHASWLGDDANN-UHFFFAOYSA-M 0.000 description 6
239000007858 starting material Substances 0.000 description 6
239000010439 graphite Substances 0.000 description 5
VPZFYLQMPOIPKH-UHFFFAOYSA-N 1,1,1,2-tetramethoxyethane Chemical compound COCC(OC)(OC)OC VPZFYLQMPOIPKH-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
150000002905 orthoesters Chemical class 0.000 description 3
ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 3
AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 description 3
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
239000001294 propane Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
RIDZNWMRIHBVLI-UHFFFAOYSA-N 2-methylbutane-1,1,1,2-tetracarboxylic acid Chemical compound CCC(C(C(=O)O)(C(=O)O)C(=O)O)(C(=O)O)C RIDZNWMRIHBVLI-UHFFFAOYSA-N 0.000 description 1
VQVAYZOYBHCXFS-UHFFFAOYSA-N 3-methoxypentanenitrile Chemical compound CCC(OC)CC#N VQVAYZOYBHCXFS-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
239000004805 Cyclohexane-1,2-dicarboxylic acid Chemical class 0.000 description 1
MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000010405 anode material Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003575 carbonaceous material Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000010406 cathode material Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical class OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
CZGCYHISZCRQFR-UHFFFAOYSA-N dimethyl 2-methoxybutanedioate Chemical compound COC(=O)C(OC)CC(=O)OC CZGCYHISZCRQFR-UHFFFAOYSA-N 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
230000005611 electricity Effects 0.000 description 1
230000005518 electrochemistry Effects 0.000 description 1
239000007772 electrode material Substances 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
DKHSSRCQXGHSTM-UHFFFAOYSA-M ethyl(tripropyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCC[N+](CC)(CCC)CCC DKHSSRCQXGHSTM-UHFFFAOYSA-M 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007770 graphite material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 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
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003014 ion exchange membrane Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
LNYJYVGUHXQWLO-UHFFFAOYSA-M methyl sulfate;triethyl(methyl)azanium Chemical compound COS([O-])(=O)=O.CC[N+](C)(CC)CC LNYJYVGUHXQWLO-UHFFFAOYSA-M 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000005486 organic electrolyte Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910001925 ruthenium oxide Inorganic materials 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction 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

Definitions

the present invention relates to a process for the preparation of alkoxylated carbonyl compounds (compounds I) of the general formula I
R ⁇ R 2 is hydrogen or Ci to Cökkyl
R 3 independently of one another C ⁇ ⁇ C to ß alkyl a is 0 or 1 b is 2 or 3
R 4 , R 5 , R 6 , R 7 are hydrogen or C 1 -C 6 -alkyl
R 5, R 6 Ci to Cg alkyl or Ci to C alkoxy ß mean in the presence of a C ⁇ ⁇ to C ⁇ 6 alkyl alcohol (compounds III)
a conventional organic compound (compounds IV) is used as the cathodic depolarizer, which is suitable for the electrochemical reduction, and the anodic oxidation and the cathodic reduction are carried out in an undivided electrolysis cell in the presence of Ci-C ⁇ -alkyl alcohols.
formaldehyde dimethyl acetal, trimethyl ortho-formate, acetaldehyde dimethyl acetal or trimethyl orthoacetate can be prepared from the corresponding compounds II and methanol in a particularly simple manner.
preferred compounds I and II are those in which R 4 has the same meaning as R 7 or R 5 has the same meaning as R 6 by the number of to keep the compounds contained in the reaction mixture to be worked up as small as possible.
such alcohols are employed whose alkyl radicals have the same meaning as the radicals R 8, R 9, or the alkyl radicals in R 5, R 6, provided that R 5, R 6 C ⁇ to C ß alkoxy.
Suitable cathodic depolisators are conventional organic compounds which are suitable for anodic reduction, such as aromatic hydrocarbon compounds, activated olefins, carbonyl compounds, aromatic carboxylic acids and their derivatives, and also naphthalene or nucleus-substituted naphthalene derivatives.
the process according to the invention is particularly suitable for producing the following compounds or classes of compounds:
X is an alkoxycarbonyl, nitrile or carbamide group and R 10 is Ci to C 6 alkyl.
phthalic acid phthalic acid alkyl esters or derivatives substituted on the aromatic nucleus of these compounds to give phthalide or nucleus-substituted phthalide derivatives, cyclohexane or cyclohexane-1, 2-dicarboxylic acid or cyclohexane or cyclohexene-1, 2-dicarboxylic acid dialkyl esters or according to the substitution pattern the phthalic acid derivatives substituted on the aromatic nucleus on the cyclohexane or cyclohexene ring substituted derivatives.
naphthalene or nucleus-substituted naphthalene derivatives to 1,2,3,4-tetrahydronaphthalene or the corresponding 1,2,3,4-tetrahydronaphthalene derivatives
Suitable substituents with which the aromatic nuclei in the abovementioned starting compounds can be substituted are inert, difficult-to-reduce groups such as C 1 -C 1 -alkyl, C 1 -C 6 -alkoxy or halogen.
Phthalide itself concerns it is particularly those compounds as described in DE-A-19618854.
the particularly suitable output connections are also detailed there.
the molar ratio of the starting compounds for the cathode and anode reactions and the products formed in these reactions in electrolytes to one another is not critical.
the molar ratio of the sum of the compounds I and II to the alcohols (compounds IV) is chosen from 0.1: 1 to 5: 1, preferably 0.2: 1 to 2: 1 and particularly preferably 0.3: 1 to 1: 1.
the conductive salts contained in the electrolysis solution are generally alkali, tetra- (C 1 -C 6 -alkyl) -ammonium or tri- (C ⁇ -C ⁇ - alkyl) -benzylammonium salts.
Sulfate, hydrogen sulfate, alkyl sulfates, alkyl sulfonates, halides, phosphates, carbonates, alkyl phosphates, alkyl carbonates, nitrate, alcoholates, tetrafluoroborate or perchlorate are suitable as counterions.
acids derived from the above-mentioned anions can be considered as conductive salts.
Methyltributylammonium methyl sulfate MTBS
methyltriethylammonium methyl sulfate methyl tripropylmethylammonium methyl sulfate are preferred.
customary cosolvents are added to the electrolysis solution. These are the inert solvents with a high oxidation potential that are common in organic chemistry. Examples include dimethyl carbonate or propylene carbonate.
the process according to the invention can be carried out in all customary undivided types of electrolysis cells.
One preferably works continuously with undivided flow cells.
Plate stack cells with series-shaped stack electrodes, as described for example in DE-A-19533773, are particularly suitable.
the current densities at which the process is carried out are generally 1 to 1000, preferably 10 to 100 mA / cm 2 .
the temperatures are usually -20 to 60 ° C, preferably 0 to 60 ° C. In general, normal pressure is used. Higher pressures are preferably used if at higher temperatures structures should be worked to avoid boiling of the starting compounds or cosolvents.
noble metals such as platinum or metal oxides such as ruthenium or chromium oxide or mixed oxides of the Ruo x Tio x type are suitable as anode materials.
Graphite or carbon electrodes are preferred.
cathode materials are iron, steel, stainless steel, nickel or precious metals such as platinum and graphite or carbon materials.
the system is preferably graphite as anode and cathode and graphite as anode and nickel, stainless steel or steel as cathode.
the electrolyte solution is worked up using general separation methods.
the electrolysis solution is generally first distilled and the individual compounds are obtained separately in the form of different fractions. Further purification can be carried out, for example, by crystallization, distillation or by chromatography.
annular disk electrodes each with an area of 140 cm 2 and an outer diameter of 14 cm, are arranged so that they form a stack.
the disks are set to a distance of 1 mm using spacers, thus creating 10 gaps between the ring disks.
the electrode material is graphite.
the inner 0.5 cm thick disks are switched bipolar under electrolysis conditions.
the top electrode is anodically contacted by means of a graphite stamp and a cover disk, the bottom electrode is contacted cathodically, the cathodic contact runs over the base plate of the cell.
the electrolyte flows through the central hole in the base plate into the cell, spreads over the gaps and leaves the cell above the top electrode.
the cell is part of a circulation apparatus in which the electrolyte is pumped around, heated or cooled.
975 g of tetramethoxyethane, 936 g of dimethyl maleate, 170 g of a 60% methanolic solution of methyltributylammonium methyl sulfate and 419 g of methanol were electrolyzed at a current of 3 A, the current strength decreased to 2.5 A during the electrolysis, the voltage per gap rose from 5 V to 6 V, electrolysis was continued until 95% of the dimethyl maleate had been converted.
the electrolysis discharge contained 24.4% methyl butanetetracarboxylic acid, 14.2% trimethyl orthoformate, 25.6% tetramethoxyethane and 1.7% dimethyl maleate.
the selectivity of the ortho ester formation was 82%.
the composition of the electrolysis discharge was determined using a gas chromatograph and is shown in% by area (GC area%).
a cell according to Example 1 was used, the number of columns was 7.
a cell according to Example 2 was used.
the cell and the cell circuit are constructed analogously to example 1, 11 electrodes with a diameter of 65 mm and an area of 31.6 cm 2 form 10 gaps.

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Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

EP01994702A 2000-11-24 2001-11-22 Procede de production de liaisons carbonyle alcoxylees par oxydation anodique et reaction de couplage cathodique pour realiser une synthese organique Expired - Lifetime EP1348043B1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10058304		2000-11-24
DE10058304A DE10058304A1 (de)	2000-11-24	2000-11-24	Verfahren zur Herstellung von alkoxylierten Carbonylverbindungen durch ein anodisches Oxidationsverfahren unter Nutzung der kathodischen Koppelreaktion zur organischen Synthese
PCT/EP2001/013587 WO2002042524A2 (fr)	2000-11-24	2001-11-22	Procede de production de liaisons carbonyle alcoxylees par oxydation anodique et reaction de couplage cathodique pour realiser une synthese organique

Publications (2)

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EP1348043A2 true EP1348043A2 (fr)	2003-10-01
EP1348043B1 EP1348043B1 (fr)	2005-03-09

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EP01994702A Expired - Lifetime EP1348043B1 (fr)	2000-11-24	2001-11-22	Procede de production de liaisons carbonyle alcoxylees par oxydation anodique et reaction de couplage cathodique pour realiser une synthese organique

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US (1)	US6822124B2 (fr)
EP (1)	EP1348043B1 (fr)
JP (1)	JP3906153B2 (fr)
CN (1)	CN1329556C (fr)
AT (1)	ATE290616T1 (fr)
AU (1)	AU2002224874A1 (fr)
CA (1)	CA2429450A1 (fr)
DE (2)	DE10058304A1 (fr)
ES (1)	ES2238501T3 (fr)
NO (1)	NO20032335L (fr)
WO (1)	WO2002042524A2 (fr)

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DE10355087A1 (de) *	2003-11-24	2005-06-09	Basf Ag	Verfahren zur elektrochemischen Herstellung eines kristallinen porösen metallorganischen Gerüstmaterials
FR2910784B1 (fr)	2006-12-27	2009-02-20	Arkema France	Utilisation de composes pour la conservation du corps humain ou animal et compositions les comprenant
DE102007008668A1 (de) *	2007-02-20	2008-08-21	Tesa Ag	Verfahren zum Beschriften oder Markieren von Oberflächen
US8889920B2 (en) *	2010-02-12	2014-11-18	Basf Se	Process for preparing 4-isopropylcyclohexylmethanol
WO2011098432A2 (fr) *	2010-02-12	2011-08-18	Basf Se	Procédé de préparation de 4-isopropylcyclohexylméthanol
KR20150023709A (ko) *	2012-06-15	2015-03-05	바스프 에스이	친핵체 존재 하의 유기 기판의 애노드 산화
CN107473945B (zh) *	2016-06-08	2020-09-01	中国科学院大连化学物理研究所	一种催化甲醇直接氧化酯化制四甲氧基甲烷的方法
CN106591877A (zh) *	2016-11-14	2017-04-26	江苏科技大学	一种中心原子可变换的偶联剂及其制备方法
US11060197B2 (en) *	2016-11-24	2021-07-13	Avantium Knowledge Centre B.V.	Process for treating a dicarboxylic acid composition
DE102017113141A1 (de) *	2017-06-14	2018-12-20	Westfälische Wilhelms-Universität Münster	Elektrolyt für Lithium-Ionen-Batterien
DE102017012021A1 (de)	2017-12-22	2019-06-27	Friedrich-Schiller-Universität Jena	Acetalischer Elektrolyt
JP7105418B2 (ja) *	2018-02-08	2022-07-25	Ｅｎｅｏｓ株式会社	シス－二置換非芳香族化合物の製造装置および製造方法
CN108677210B (zh) *	2018-04-17	2019-10-29	大连理工大学	一种酮与羧酸在电化学氢泵反应器中一步加氢酯化的方法
CN112195481B (zh) *	2020-11-02	2021-12-10	上海漫关越水处理有限公司	膜电解合成四甲氧基乙烷的方法

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- 2000-11-24 DE DE10058304A patent/DE10058304A1/de active Pending
2001
- 2001-11-22 AU AU2002224874A patent/AU2002224874A1/en not_active Abandoned
- 2001-11-22 EP EP01994702A patent/EP1348043B1/fr not_active Expired - Lifetime
- 2001-11-22 AT AT01994702T patent/ATE290616T1/de not_active IP Right Cessation
- 2001-11-22 CN CNB018194397A patent/CN1329556C/zh not_active Expired - Fee Related
- 2001-11-22 ES ES01994702T patent/ES2238501T3/es not_active Expired - Lifetime
- 2001-11-22 US US10/432,249 patent/US6822124B2/en not_active Expired - Fee Related
- 2001-11-22 DE DE50105570T patent/DE50105570D1/de not_active Expired - Fee Related
- 2001-11-22 CA CA002429450A patent/CA2429450A1/fr not_active Abandoned
- 2001-11-22 JP JP2002545221A patent/JP3906153B2/ja not_active Expired - Fee Related
- 2001-11-22 WO PCT/EP2001/013587 patent/WO2002042524A2/fr not_active Ceased
2003
- 2003-05-23 NO NO20032335A patent/NO20032335L/no unknown

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NO20032335D0 (no)	2003-05-23
EP1348043B1 (fr)	2005-03-09
US20040026263A1 (en)	2004-02-12
CN1476491A (zh)	2004-02-18
DE50105570D1 (de)	2005-04-14
AU2002224874A1 (en)	2002-06-03
ES2238501T3 (es)	2005-09-01
CN1329556C (zh)	2007-08-01
CA2429450A1 (fr)	2002-05-30
WO2002042524A2 (fr)	2002-05-30
JP2004514791A (ja)	2004-05-20
JP3906153B2 (ja)	2007-04-18
ATE290616T1 (de)	2005-03-15
WO2002042524A3 (fr)	2003-03-13
US6822124B2 (en)	2004-11-23
DE10058304A1 (de)	2002-05-29
NO20032335L (no)	2003-07-14

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Publication	Publication Date	Title
EP1348043B1 (fr)	2005-03-09	Procede de production de liaisons carbonyle alcoxylees par oxydation anodique et reaction de couplage cathodique pour realiser une synthese organique
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DE2855508A1 (de)	1980-07-10	Verfahren zur herstellung von benzaldehyden
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