US1709297A - Process of preparing maleic and succinic acid from furfural by electrolysis - Google Patents
Process of preparing maleic and succinic acid from furfural by electrolysis Download PDFInfo
- Publication number
- US1709297A US1709297A US98917A US9891726A US1709297A US 1709297 A US1709297 A US 1709297A US 98917 A US98917 A US 98917A US 9891726 A US9891726 A US 9891726A US 1709297 A US1709297 A US 1709297A
- Authority
- US
- United States
- Prior art keywords
- acid
- furfural
- electrolysis
- succinic acid
- maleic
- 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
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
- C25B3/23—Oxidation
Definitions
- This invention relates to. the of maleic and succinic acid from furfural by electrolysis and the ob'ect of the invention is to preparethese acids y far better efliciency 5 than any other process hitherto known.
- furfural dissolvedor suspended'in an acid or a salt solution is oxidized by electrolysis.
- Maleic and succinic acid may be isolated from the resulting oxidation product which consists of their mixture.
- Maleic acid can fumaric acid by the usual methods. By the reduction of maleic as well as fumaric acid,
- succinic acid can also be produced.
- a two-compartment cell the compartments being separated from each other by a porous diaphragm is employed.
- the anodic compartment contains 5 per cent sulphuric acid 'inwhich 'furfural is dissolved or suspended, whilst the cathodic compartment contains 10 per cent sulphuric acid.
- the electrodes are advantageously made of lead pipe coils which serve also as cooling means by passingwatcr through them.
- a relatively low current density, for example,”say,0.02 amps. per sq. cm. is employed and the temperature kept at C.- The electrolysis is "continued, until the anolyte no longer gives the characteristic reaction of furfural with aniline acetate, and
- succinic-acid alone is desired, the current is reversed in the same apparatus after the furfural is perfectly oxidized.
- the maleic acid mixed with converted into succinic acid.
- the cathodic solution is moderately concentrated and cooled.
- the crystals of succinic acid which separate are collected and purified by recrystallization from hot water.
- the electrolysis is carried out as in the Example 1, except a lead peroxide anode is used instead of-a lead one, and a relatively high current density, peres per sq. cm. 1s employed.
- a lead peroxide anode is used instead of-a lead one, and a relatively high current density, peres per sq. cm. 1s employed.
- chiefly maleic acid is produced and theyield reaches 7 5 per cent'of the theory.
- anodic solution obtained in this case for the preparation of fumaric acid.
- the fuma-ric acid converted from maleic acid by the catalytic action of hydrochloric acid crystallizes out. It is collected and recrystallized from hot water.
- the process of preparing maleic and succinic acids which comprises electrolyzing an acid solution of furfural.
- succinic acid is reduced and for example, say, 0.06 ame solution, is
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)
Description
' Patented Apr. 16, 1929.'
I'OFFICE. A
TEIJIRO .YABUTA, OF SETAGAYA-MACHI, EBABA-GORI, JAPAN, ASSIGNOR TO Z AIDAN H OJIN RIKAGAKU KENKYUJ'O,
' PROCESS OI PREPARING HALEIC AND S'U'COINIC ELECTROLYSIS.
1T0 Drawing. Application filed larch 31,1926,
This invention relates to. the of maleic and succinic acid from furfural by electrolysis and the ob'ect of the invention is to preparethese acids y far better efliciency 5 than any other process hitherto known.
-In carrying out my invention, furfural dissolvedor suspended'in an acid or a salt solution, is oxidized by electrolysis. Maleic and succinic acid may be isolated from the resulting oxidation product which consists of their mixture.
Moreover, b usin the proper materials for the electro es an also by employing the proper current density, either Ihaleic or suceinic acid can be obtained as the main product.
Maleic acid can fumaric acid by the usual methods. By the reduction of maleic as well as fumaric acid,
succinic acid can also be produced.
Example 1.
A two-compartment cell, the compartments being separated from each other by a porous diaphragm is employed. The anodic compartment contains 5 per cent sulphuric acid 'inwhich 'furfural is dissolved or suspended, whilst the cathodic compartment contains 10 per cent sulphuric acid. The electrodes are advantageously made of lead pipe coils which serve also as cooling means by passingwatcr through them. A relatively low current density, for example,"say,0.02 amps. per sq. cm. is employed and the temperature kept at C.- The electrolysis is "continued, until the anolyte no longer gives the characteristic reaction of furfural with aniline acetate, and
it is then moderately concentrated. On cool- 1 ing mixed crystals. of succinic and maleic acid (80 per cent and 20 per cent respectively) separate. a They are collected an isolated from each preparation easily be converted into other by fractional crystallization.
01 'roxyo, JAPAN.
ACID FROM FUBFURAL BY Serial No.98,917, and in-Iapan June 22, 1825.
Some more crystals are obtained from the mother hquor on further evaporization, but
If succinic-acid alone is desired, the current is reversed in the same apparatus after the furfural is perfectly oxidized. The maleic acid mixed with converted into succinic acid. The cathodic solution is moderately concentrated and cooled. The crystals of succinic acid which separate are collected and purified by recrystallization from hot water.
Example 52.-
The electrolysis is carried out as in the Example 1, except a lead peroxide anode is used instead of-a lead one, and a relatively high current density, peres per sq. cm. 1s employed. In this case, chiefly maleic acid is produced and theyield reaches 7 5 per cent'of the theory.
It is advantageous to use the anodic solution obtained in this case for the preparation of fumaric acid. For this purpose, an amount of sodium chloride corresponding to the sulphuric acid contained in th added and boiled for about half an hour. On cooling, the fuma-ric acid converted from maleic acid by the catalytic action of hydrochloric acid, crystallizes out. It is collected and recrystallized from hot water.
In these operations described above, increased-yield is obtained by the addition of vanadium, cerium or manganese compounds as catalysis in the anolyte.
I claim: y
The process of preparing maleic and succinic acids which comprises electrolyzing an acid solution of furfural.
In testimony whereof I aflix TEIJIRO my signature. YABUTA.
succinic acid, is reduced and for example, say, 0.06 ame solution, is
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1709297X | 1925-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1709297A true US1709297A (en) | 1929-04-16 |
Family
ID=15913971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US98917A Expired - Lifetime US1709297A (en) | 1925-06-22 | 1926-03-31 | Process of preparing maleic and succinic acid from furfural by electrolysis |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1709297A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2420954A (en) * | 1941-06-12 | 1947-05-20 | Danciger Oil & Refineries Inc | Electrolytic production of succinic acid from butyrolactone |
| US20190106796A1 (en) * | 2017-10-09 | 2019-04-11 | Wisconsin Alumni Research Foundation | Electrochemical oxidation of aromatic aldehydes in acidic media |
| WO2020256556A1 (en) | 2019-06-21 | 2020-12-24 | Stichting Wageningen Research | Method for preparing maleic acid |
| US11912656B2 (en) | 2018-12-21 | 2024-02-27 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Oxidation of 5-hydroxy-2-furanone to maleates |
-
1926
- 1926-03-31 US US98917A patent/US1709297A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2420954A (en) * | 1941-06-12 | 1947-05-20 | Danciger Oil & Refineries Inc | Electrolytic production of succinic acid from butyrolactone |
| US20190106796A1 (en) * | 2017-10-09 | 2019-04-11 | Wisconsin Alumni Research Foundation | Electrochemical oxidation of aromatic aldehydes in acidic media |
| US11142833B2 (en) * | 2017-10-09 | 2021-10-12 | Wisconsin Alumni Research Foundation | Electrochemical oxidation of aromatic aldehydes in acidic media |
| US11912656B2 (en) | 2018-12-21 | 2024-02-27 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Oxidation of 5-hydroxy-2-furanone to maleates |
| WO2020256556A1 (en) | 2019-06-21 | 2020-12-24 | Stichting Wageningen Research | Method for preparing maleic acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3720591A (en) | Preparation of oxalic acid | |
| US1709297A (en) | Process of preparing maleic and succinic acid from furfural by electrolysis | |
| McKee et al. | A New Method for Electro‐Organic Reductions | |
| US2830941A (en) | mehltretter | |
| US2813825A (en) | Method of producing perchlorates | |
| DE2630927A1 (en) | METHOD FOR PRODUCING PHTHALIDOCARBONIC ACID- (5) | |
| GB253877A (en) | A process of preparing maleic and succinic acid from furfural | |
| US2130151A (en) | Production of quinone and hydroquinone | |
| Sakurai | ELECTROLYTIC REDUCTION OF ALKYL-PHTHALIMIDES. IV. COMPLETE REDUCTION | |
| US2024242A (en) | Apparatus for producing anhydrous magnesium chloride | |
| JPS60114585A (en) | Manufacture of glycol | |
| DE2642496C2 (en) | Process for the preparation of p-hydroxymethylbenzoic acid | |
| DE469234C (en) | Process for the production of maleic and succinic acid | |
| US2285858A (en) | Electrolytic process for the production of quinone and hydroquinone | |
| US2846383A (en) | Process of manufacturing perchloric acid by anodic oxidation of chlorine | |
| US2453701A (en) | Process for electrolytic oxidation of quinoline to quinolinic acid | |
| US1378939A (en) | Process of making thymol from nitrocymene | |
| US4387245A (en) | Preparation of diacetoneketogulonic acid by oxidation of diacetonesorbose | |
| JPS60237041A (en) | Preparation of 3-propionylsalicylic acid derivative | |
| US3169913A (en) | Preparation of gem-dinitroparaffins by electrolysis | |
| US1544357A (en) | Electrolytic process | |
| US2223929A (en) | Process for electrolytically producing arsenates | |
| US1842535A (en) | Production of hydrated chromic chloride | |
| SU93680A1 (en) | The method of obtaining omega-hydroxypentadecanoic acid | |
| US1492636A (en) | Process for the manufacture of chromates and bichromates |