JPH0568555B2 - - Google Patents
Info
- Publication number
- JPH0568555B2 JPH0568555B2 JP59112151A JP11215184A JPH0568555B2 JP H0568555 B2 JPH0568555 B2 JP H0568555B2 JP 59112151 A JP59112151 A JP 59112151A JP 11215184 A JP11215184 A JP 11215184A JP H0568555 B2 JPH0568555 B2 JP H0568555B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- squaric acid
- electrolytic
- products
- catholyte
- 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.)
- Expired - Lifetime
Links
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000003792 electrolyte Substances 0.000 claims description 17
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 15
- -1 aliphatic nitrile Chemical class 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 238000005119 centrifugation Methods 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000010349 cathodic reaction Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 4
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000009972 noncorrosive effect Effects 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 239000000956 alloy Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 238000002048 anodisation reaction Methods 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000004020 conductor Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PWEBUXCTKOWPCW-UHFFFAOYSA-L squarate Chemical compound [O-]C1=C([O-])C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-L 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000001047 cyclobutenyl group Chemical class C1(=CCC1)* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/499,575 US4461681A (en) | 1983-05-31 | 1983-05-31 | Process for the preparation of squaric acid by the electrolysis of carbon monoxide in anhydrous aliphatic nitrile solvent media |
| US499575 | 1995-07-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS605889A JPS605889A (ja) | 1985-01-12 |
| JPH0568555B2 true JPH0568555B2 (US20030199744A1-20031023-C00003.png) | 1993-09-29 |
Family
ID=23985794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59112151A Granted JPS605889A (ja) | 1983-05-31 | 1984-05-31 | スクアリン酸の製造方法 |
Country Status (9)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4523980A (en) * | 1984-08-31 | 1985-06-18 | The Halcon Sd Group, Inc. | Process for the recovery of high purity squaric acid |
| IE65907B1 (en) * | 1990-02-26 | 1995-11-29 | Lonza Ag | New 3-hydroxy-2-cyclobuten-1-one salts their preparation and use |
| US7164507B2 (en) * | 2002-10-25 | 2007-01-16 | Xerox Corporation | Image input terminal |
| US7445884B2 (en) * | 2004-06-09 | 2008-11-04 | Konica Minolta Medical & Graphic, Inc. | Photothermographic material, development method and thermal development device thereof |
| JP4433918B2 (ja) * | 2004-07-15 | 2010-03-17 | コニカミノルタエムジー株式会社 | 画像形成方法 |
| US7220536B2 (en) * | 2004-10-22 | 2007-05-22 | Konica Minolta Medical & Graphic, Inc. | Silver salt photothermographic dry imaging material, thermal development method of the same, and thermal development apparatus for the same |
| EP1906235A4 (en) | 2005-07-20 | 2008-07-30 | Konica Minolta Med & Graphic | IMAGE FORMING METHOD |
| US7504200B2 (en) | 2007-02-02 | 2009-03-17 | Konica Minolta Medical & Graphic, Inc. | Photothermographic material |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290350A (en) * | 1960-05-16 | 1966-12-06 | Du Pont | Alpha, alpha, alpha', alpha'-tetramethyl-xylylene diisocyanates and alpha, alpha-dimethylisopropenylbenzyl isocyanates and the preparation thereof from isocyanic acid and olefins |
| US3502475A (en) * | 1967-07-13 | 1970-03-24 | Du Pont | Highly adherent coated films and method of producing same |
| US3833489A (en) * | 1971-07-24 | 1974-09-03 | R Ercoli | Process for the preparation of squaric acid by reductive cyclotetramerization of carbon monoxide |
| JPS5239612A (en) * | 1975-09-22 | 1977-03-28 | Asahi Chem Ind Co Ltd | Process for preparation of unsaturated glycol diesters |
| JPS5579883A (en) * | 1978-12-13 | 1980-06-16 | Mitsui Petrochem Ind Ltd | Preparation of 3,4-dialkoxyphenol |
| JPS5579882A (en) * | 1978-12-13 | 1980-06-16 | Mitsui Petrochem Ind Ltd | Electrolytic acyloxylation method |
| JPS57212152A (en) * | 1981-06-05 | 1982-12-27 | Shell Int Research | Manufacture of isocyanate and/or derivative |
-
1983
- 1983-05-31 US US06/499,575 patent/US4461681A/en not_active Expired - Lifetime
-
1984
- 1984-05-25 IT IT48259/84A patent/IT1177750B/it active
- 1984-05-30 BE BE0/213038A patent/BE899792A/fr not_active IP Right Cessation
- 1984-05-30 CA CA000455434A patent/CA1241290A/en not_active Expired
- 1984-05-30 DE DE19843420333 patent/DE3420333A1/de active Granted
- 1984-05-30 FR FR8408588A patent/FR2546910B1/fr not_active Expired
- 1984-05-30 NL NL8401733A patent/NL192457C/nl not_active IP Right Cessation
- 1984-05-31 GB GB08413890A patent/GB2141708B/en not_active Expired
- 1984-05-31 JP JP59112151A patent/JPS605889A/ja active Granted
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290350A (en) * | 1960-05-16 | 1966-12-06 | Du Pont | Alpha, alpha, alpha', alpha'-tetramethyl-xylylene diisocyanates and alpha, alpha-dimethylisopropenylbenzyl isocyanates and the preparation thereof from isocyanic acid and olefins |
| US3502475A (en) * | 1967-07-13 | 1970-03-24 | Du Pont | Highly adherent coated films and method of producing same |
| US3833489A (en) * | 1971-07-24 | 1974-09-03 | R Ercoli | Process for the preparation of squaric acid by reductive cyclotetramerization of carbon monoxide |
| JPS5239612A (en) * | 1975-09-22 | 1977-03-28 | Asahi Chem Ind Co Ltd | Process for preparation of unsaturated glycol diesters |
| JPS5579883A (en) * | 1978-12-13 | 1980-06-16 | Mitsui Petrochem Ind Ltd | Preparation of 3,4-dialkoxyphenol |
| JPS5579882A (en) * | 1978-12-13 | 1980-06-16 | Mitsui Petrochem Ind Ltd | Electrolytic acyloxylation method |
| JPS57212152A (en) * | 1981-06-05 | 1982-12-27 | Shell Int Research | Manufacture of isocyanate and/or derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2141708A (en) | 1985-01-03 |
| CA1241290A (en) | 1988-08-30 |
| US4461681A (en) | 1984-07-24 |
| NL192457C (nl) | 1997-08-04 |
| FR2546910A1 (fr) | 1984-12-07 |
| JPS605889A (ja) | 1985-01-12 |
| NL8401733A (nl) | 1984-12-17 |
| FR2546910B1 (fr) | 1988-10-14 |
| IT8448259A0 (it) | 1984-05-25 |
| GB2141708B (en) | 1986-12-10 |
| IT1177750B (it) | 1987-08-26 |
| NL192457B (nl) | 1997-04-01 |
| DE3420333C2 (US20030199744A1-20031023-C00003.png) | 1993-02-04 |
| DE3420333A1 (de) | 1984-12-06 |
| GB8413890D0 (en) | 1984-07-04 |
| BE899792A (fr) | 1984-11-30 |
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