US1816848A - Process for the production of thiocyano derivatives - Google Patents
Process for the production of thiocyano derivatives Download PDFInfo
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- US1816848A US1816848A US397163A US39716329A US1816848A US 1816848 A US1816848 A US 1816848A US 397163 A US397163 A US 397163A US 39716329 A US39716329 A US 39716329A US 1816848 A US1816848 A US 1816848A
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- thiocyano
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- mixture
- derivatives
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- 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 roduction -of the thiocyano derlvatives aromatlc compounds.
- thiocyano derivatives by the action of a halogen on a mixture of an alkali thiocyanate and the compoundwhose thiocyano I derivative was tobe prepared.
- This method 4 of free halogen tends to accelerate the polyl I by. the action of thiocyanogen on the commerization of thiocyanogen.
- the yield is considerablyjbetter but the recovery of the halogens is not easy and thus the process becomes quite expensive.
- thiocyano derivatives can be very conveniently prepared in good yields electrolytically.
- the compound whose thiocyano derivative is to be prepared sometimes known as the depolarizer, is mixed with a soluble thiocyanate or thiocyanic acid and electrolyzed, using an insoluble anode.
- alcohol has been added to the electrolyte to increase the solubility of theconipound whose thiocyano derivative is to be prepared, and in some cases to prevent freezing at the low temperatures.
- the proportions are by weight.
- Emample J The preparation of gram-thiocyano-ortho-toluidine The following electrolyte is made up:
- Example 3 The ,preparation of .Z-amino 5-thz'ocyano beneoz'e aeil- The following electrolyte is made up:
- the electrolyte is cooled to 0 C. and electrolyzed between a rotating graphite anode and an aluminum cathode; a' current density, of 1.5 amperes per square decimeter being maintained.
- Example 5 The preparation of I parathioeyano-ortho-eresol The following electrolyte is made up: 20' parts sodium thiocyanate, 27 parts water, 25 parts hydrochloric acid (35%), 36 parts methyl alcohol, 11 parts ortho cresol. This is electrolyzed between a. ro-
- Thz'ocyano resorcinol 25 parts calcium thiocyanate solution are treated with 63 parts sulphuric acid "20% and the calcium sulphate filtered oil.
- Example 8 Thz'oayano phenol 14 parts of 88% phenol and 20 parts sodium thiocyanate are dissolved in 15 parts of ethyl alcohol and 35 parts water, This solution is placed in the anode compartment of a divided cell. 10% sodium hydroxide solution is placed in the cathode compartment. A rotating graphite anode and copper cathode are used. An anode current density of 1 ampere per square decimeter is maintained until the theoretical amount of current has been used. The temperature is kept between 0 C. and 13" C, At the end of the electrolysis, the anolyte is found to contain 25% of the theoretical amount of thiocyano phenol.
- a process for the productionof thiocyano derivatives of organic compounds which comprises mixing the compound whose derivative is desired with a substance capable of yieldingthiocyanogen ions and pounds which comprises mixing the compound whose derivative is desired w1th a substance capable of yielding thiocyanoggn ions and electrolyzing the mixture.
- a process for the production of the thiocyanoderivatives of an aromatic compound of the roup consisting of amines "and phenols 'w ich comprises mixing the rivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
- a process for the production of thiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
- a process for the production of parathiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
- a process for the production of thiocyano derivatives of an aromatic compound of the group consisting ofamines and phenols which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance.
- a process for the production of parathiocyano derivatives of a compound of the group consisting of amines and phenols which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
- a process for the production of thiocyano derivatives of organic compounds which comprises mixing the compound whose derivative is desired with a substance capable ofyielding thiocyanogen ions and below about 5 C.
- a process for the production of thiocyano derivatives of organic compounds which comprises mixing the compound Whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture at a temperature below about 5 C.
- a process for the production of thiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a temperature below about 5 C.
- a process for the production of parathiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with -a substance capable of yielding thiocyanogen I ions and electrolyzing the mixture at a temperature below about 5 C.
- a process for the production of the thiocyano derivative of an aromatic compound of the group consisting of amines and phenols which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a tem perature below about 5 C.
- a process for the production of the para-thiocyano derivative of a compound of the group consisting of amines and phenols which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a temperature below about 5 C.
- a process for the production of thiocyano derivatives of organic compounds which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and an alcohol and electrolyzingthe mixture at a temperature below about 5 C 18.
- pounds which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen lons and an alcohol and electrolyzing the mixture at a temperature belowabout 5 C.
- a process for the production of thiocyano derivatives of organic compounds WhlCh comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture while maintaining an anode current density between about 1 amp. and 3 amps. per square decimeter of anode surface and while cooling the electrolyte.
- a process for the production ofthiocyano derivatives of aromatic compounds which comprises mixing the compound,
- anode current density capable of yielding thiocyanogen ions and electrolyzing the mixture while maintaining an anode current density of between 1 about 1 amp. and 3 amps. per square decimeter of anode surface and while cooling the electrolyte.
- a process -for the production of thiocyano derivatives of. organic compounds which comprises mixing the compound whose derivative is desired with a substance selected. from the group consisting of thiocyanates, thiocyanic; acid, and a substance capable of producing'thiocyanic acid and electrolyzing the mixture while maintaining an anode current density of between about 1 amp. and 3 amps. per square decimeter of anode surface and while cooling the electrolyte.
- a process for the production of thiocyano derivatives of organic compounds which comprises mixing the com- 0 C. while maintaining an anode current density ofabout '1.5 amp. per square decimeter of anode surface.
- a processforvthe production of 2- amino, fi-thiocya'no benzoic acid which comprises mixing anthranilic acid with a substance capable of yielding thiocyanogen I ions and electrolyzing the mixture.
- a process for the production of 2- I amino, 5-thiocyano benzoic acid which comprises mixing anthranilic acidwith a thiocyanate and electrolyzing the mixture at a temperature of about 5C. while maintaining an anode-current'density of between 1 and 1.5 amps; per square decimeter of anode surface.
- a pro ess for the production of para--' thiocyano-dimethylaniline which comprises mixing adimethylaniline salt with :a substance capable of yielding thiocyanogen ions ,.”mixing the hydrochloride of dimethylaniline 4 cyano-resorcinol which and electrolyzing the mixture.
- a process for the production of para thiocyano-dimethylaniline which comprises with ammonium thiocyanate and electrolyzing the mixture at a temperature of about 0 C. while maintaining an anode current density of from 2 to 3 am s. r uare decimeter of anode surface.
- p pe 26 A process for the production of thiocyano-resorcinol which comprises resorcinol with a substance capable of yieldmg thiocyanogen ions and electrolyzing the mixture.
Description
Patented Aug. 4, 1931 UNITED STATES PATENT OFF-ICE EDWARD LESLIE HELWIG, OF BRISTOL TOWNSHIP, BUCKS COUNTY, PENNSYLVANIA PROCESS THE PRODUCTION OF THIOGYANO DERIVATIVES No Drawing.
This invention relates to the roduction -of the thiocyano derlvatives aromatlc compounds. In the past it has been customary to prepare thiocyano derivatives by the action of a halogen on a mixture of an alkali thiocyanate and the compoundwhose thiocyano I derivative was tobe prepared. This method 4 of free halogen tends to accelerate the polyl I by. the action of thiocyanogen on the commerization of thiocyanogen. With the more expensive halogens, bromine and iodine, the yield is considerablyjbetter but the recovery of the halogens is not easy and thus the process becomes quite expensive.
These derivatives have also been prepared pound in an inert solvent. This is also not very satisfactory due to the rapid polymerizatlon of the thiocyanogen.
I have found that these thiocyano derivatives can be very conveniently prepared in good yields electrolytically. The compound whose thiocyano derivative is to be prepared, sometimes known as the depolarizer, is mixed with a soluble thiocyanate or thiocyanic acid and electrolyzed, using an insoluble anode.
It is usually not necessary to use a diaphragm although it is advisable wherethe compound desired is easily reducible.
Cooling the electrolyte has been found to increase the yield.
In most cases, alcohol has been added to the electrolyte to increase the solubility of theconipound whose thiocyano derivative is to be prepared, and in some cases to prevent freezing at the low temperatures.
employed.
The current densit is so regulated that the thiocyanogen is' iberated only so rap- Application filed October 3, 1929. Serial No. 397,163.
idly as it can be taken up by the compound, whose thiocyano derivative is to be prepared, as otherwise it is wasted either by further oxidation or by polymerization. In the absence of said compound the bulk of the thiocyanogen polymerizes as it is liberated As the concentration of the said compound drops off towards the end of the reaction, it is frequently advisable to reduce the current density somewhat to prevent wasting thiocyanat.
It is not necessary to restrict the work to quali cations being that the electrode must not oxidize the thiocyanogen or the compound used too far nor be attacked itself. Any cathode material may be used which will not reduce the desired thiocyano derivative, and even this restriction is removed if a diaphragm is employed.
I have obtained the best results when applying my invention to the production of para-thiocyano derivatives, although it may be adapted to the production of meta and ortho derivatives.
articular anode material, the only" The following examples will serve to illustrate the nature of the invention but the invention is not restricted to the examples.
The proportions are by weight.
Emample J. The preparation of gram-thiocyano-ortho-toluidine The following electrolyte is made up:
20 parts sodium thiocyanate, 35 parts water, 25 parts hydrochloric acid (35%), 25 parts ethyl alcohol (95%), 12 parts ortho-toluidine. This is electrolyzed between a rotating graphite anode and a copper cathode. The cell is cooled to 0 C.+ 5 C. The anode current density is maintained at about 2 amperes per square decimeter. When 1.25 times the theoretical amount of current, measured as ampere hours or any other units, has passed through the cell, the current is interrupted. The electrolyte is found to contain a yield of 75% of the product, based on the toluidine taken, showing a" current efiiciency of 60%.
'- H. Kersteln & R. Hofimaim-Ber.. 57pages 491-196.
Wan- 2. The preparation of para-thiocyano-dimethg lam'line The following electrolyte is made up:
37 parts ammonium thiocyanate, 95 parts water, 50 parts ethyl alcohol (95% partsdimethylaniline .38 parts hydrochloric acid (35%). The e ectrolyte 1s cooled to C. and, while being circulated by means m of a centrifugal pum is electrolyzed between stationary grap ite'anodes and copper cathodes. An anode current densltypf 2 to 3 amperes per square decimeter 1s ma1n-.
tained and 1.2 to 1.4 times the theoretical amount of current is passed through the cell.- 75% of the dimethylaniline 1S converted the thiocyano derivative.
Example 3.- The ,preparation of .Z-amino 5-thz'ocyano beneoz'e aeil- The following electrolyte is made up:
parts sodium thiocyanate, 17 parts water, 21 parts hydrochloric acid (-35%), 35 parts methyl alcohol, 14 parts anthranilic acid. This is electrolyzed between a ro- 25 tating graphite anode and a stationary aluminum cathode, using an anode current density of 1.0,to 1.5 amperes per square decimeter, the. temperature being maintained around +5 C. 1.5 times the theoretical amount of current is used. 60% of the anthranilic acid is converted to the thiocyano derivative. Example 4. The preparation of J-amino .l-thz'oeyano naphthalene 34 parts of a 76% solution of calcium thiocyanate are treated with 60 parts -of 20% sulphuric acid in the cold. The calcium sulphate so formed is filtered off and Ewample .4 washed with 35 parts methyl alcohol. To
the filtrate and washings, 15 parts alphanaphthylamine are added. The electrolyte is cooled to 0 C. and electrolyzed between a rotating graphite anode and an aluminum cathode; a' current density, of 1.5 amperes per square decimeter being maintained.
1 Twice the theoretical current is passed throughthe cell. A yield of %55% is obtained, based on the alpha-naphthylamine 50 taken.
Example 5. The preparation of I parathioeyano-ortho-eresol The following electrolyte is made up: 20' parts sodium thiocyanate, 27 parts water, 25 parts hydrochloric acid (35%), 36 parts methyl alcohol, 11 parts ortho cresol. This is electrolyzed between a. ro-
tating graphite anode and an aluminum cathode, using a current density of 2 amperes per square decimeter, until 1.5 times the theoretical current is passed. The.temperature is maintained at -5 C. A yield of approximately 40% is obtained, based on the cresol taken.
Emample 6. Thz'ocyano resorcinol 25 parts calcium thiocyanate solution are treated with 63 parts sulphuric acid "20% and the calcium sulphate filtered oil.
current density of 1.5 amperes per square decimeter at. 0 C. until the theoretical amount of current has passed through the.
cell. ,A yield of 60% thiocyano-resorcinol is obtained, based on .the resorcinol taken.
I Eat-ample "7. Thioeyano resorcinol '12 parts resorcinol and 20 parts sodium thiocyanate are dissolved in 60 parts water.
- This solution is placed in the anode compartment of a divided cell. 5% sodium hydroxide solution is placed in the cathode compartment.' A rotating graphite anode and copper cathode are used. An anode current density of 1 to 2 amperes per square decimeter is maintained until the theoretical amount ofcurrent has been used. The anolyte then contains 50-60% of the theoretical amount of thiocyano-resorcinol.
Example 8. Thz'oayano phenol 14 parts of 88% phenol and 20 parts sodium thiocyanate are dissolved in 15 parts of ethyl alcohol and 35 parts water, This solution is placed in the anode compartment of a divided cell. 10% sodium hydroxide solution is placed in the cathode compartment. A rotating graphite anode and copper cathode are used. An anode current density of 1 ampere per square decimeter is maintained until the theoretical amount of current has been used. The temperature is kept between 0 C. and 13" C, At the end of the electrolysis, the anolyte is found to contain 25% of the theoretical amount of thiocyano phenol.
Having thus described the nature and objects of my invention and illustrated specific embodiments of the same, what I claim as new and desire to secure by Letters Patent is 1. A process for the productionof thiocyano derivatives of organic compounds which comprises mixing the compound whose derivative is desired with a substance capable of yieldingthiocyanogen ions and pounds which comprises mixing the compound whose derivative is desired w1th a substance capable of yielding thiocyanoggn ions and electrolyzing the mixture.
4. A process for the production of the thiocyanoderivatives of an aromatic compound of the roup consisting of amines "and phenols 'w ich comprises mixing the rivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
7. A process for the production of thiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
8. A process for the production of parathiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
9. A process for the production of thiocyano derivatives of an aromatic compound of the group consisting ofamines and phenols which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance.
capable of producing thiocyanic acid and electrolyzing the mixture.
10. A process for the production of parathiocyano derivatives of a compound of the group consisting of amines and phenols which comprises mixing the compound whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture.
11. A process for the production of thiocyano derivatives of organic compounds which comprises mixing the compound whose derivative is desired with a substance capable ofyielding thiocyanogen ions and below about 5 C.
12. A process for the production of thiocyano derivatives of organic compounds vwhich comprises mixing the compound Whose derivative is desired with a substance selected from the group consisting of thiocyanates, thiocyanic acid and a substance capable of producing thiocyanic acid and electrolyzing the mixture at a temperature below about 5 C.
13. A process for the production of thiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a temperature below about 5 C.
14. A process for the production of parathiocyano derivatives of aromatic compounds which comprises mixing the compound whose derivative is desired with -a substance capable of yielding thiocyanogen I ions and electrolyzing the mixture at a temperature below about 5 C.
15. A process for the production of the thiocyano derivative of an aromatic compound of the group consisting of amines and phenols which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a tem perature below about 5 C. 16. A process for the production of the para-thiocyano derivative of a compound of the group consisting of amines and phenols which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a temperature below about 5 C.
17. A process for the production of thiocyano derivatives of organic compounds which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and an alcohol and electrolyzingthe mixture at a temperature below about 5 C 18. A process for the production of parathlocyano derivatives of aromatic com-,
pounds which comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen lons and an alcohol and electrolyzing the mixture at a temperature belowabout 5 C.
19. A process for the production of thiocyano derivatives of organic compounds WhlCh comprises mixing the compound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture while maintaining an anode current density between about 1 amp. and 3 amps. per square decimeter of anode surface and while cooling the electrolyte. 1
electrolyzing the mixture at a temperature 20. A process for the production ofthiocyano derivatives of aromatic compounds which comprises mixing the compound,
capable of yielding thiocyanogen ions and electrolyzing the mixture while maintaining an anode current density of between 1 about 1 amp. and 3 amps. per square decimeter of anode surface and while cooling the electrolyte.
22. A process -for the production of thiocyano derivatives of. organic compounds which comprises mixing the compound whose derivative is desired with a substance selected. from the group consisting of thiocyanates, thiocyanic; acid, and a substance capable of producing'thiocyanic acid and electrolyzing the mixture while maintaining an anode current density of between about 1 amp. and 3 amps. per square decimeter of anode surface and while cooling the electrolyte.
23. A process for the production of thiocyano derivatives of organic compounds. which comprises mixing the com- 0 C. while maintaining an anode current density ofabout '1.5 amp. per square decimeter of anode surface.
28. A processforvthe production of 2- amino, fi-thiocya'no benzoic acid which comprises mixing anthranilic acid with a substance capable of yielding thiocyanogen I ions and electrolyzing the mixture.
29. A process for the production of 2- I amino, 5-thiocyano benzoic acid which comprises mixing anthranilic acidwith a thiocyanate and electrolyzing the mixture at a temperature of about 5C. while maintaining an anode-current'density of between 1 and 1.5 amps; per square decimeter of anode surface.
' In testimonywhereof l have hereunto set my hand. 1
- =EDWARDLESLIE HELWIG.
pound whose derivative is desired with a substance capable of yielding thiocyanogen ions and electrolyzing the mixture at a temperature below about 5 C. .while maintaining an anode current density of between about 1 amp; and 3 'amps. per square decimeter of anode surface.
24:. A pro ess for the production of para--' thiocyano-dimethylaniline which comprises mixing adimethylaniline salt with :a substance capable of yielding thiocyanogen ions ,."mixing the hydrochloride of dimethylaniline 4 cyano-resorcinol which and electrolyzing the mixture.
25. A process for the production of para thiocyano-dimethylaniline which comprises with ammonium thiocyanate and electrolyzing the mixture at a temperature of about 0 C. while maintaining an anode current density of from 2 to 3 am s. r uare decimeter of anode surface. p pe 26. A process for the production of thiocyano-resorcinol which comprises resorcinol with a substance capable of yieldmg thiocyanogen ions and electrolyzing the mixture. y
27. A process for the production of thiocomprises mixing resorcinol with thiocyanate and electrolyzmg the mixture at a temperature of about
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US397163A US1816848A (en) | 1929-10-03 | 1929-10-03 | Process for the production of thiocyano derivatives |
| FR702829D FR702829A (en) | 1929-10-03 | 1930-09-30 | Electrolytic production of thiocyanide derivatives |
| GB29274/30A GB364060A (en) | 1929-10-03 | 1930-09-30 | Electrolytic production of thiocyanide derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US397163A US1816848A (en) | 1929-10-03 | 1929-10-03 | Process for the production of thiocyano derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1816848A true US1816848A (en) | 1931-08-04 |
Family
ID=23570080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US397163A Expired - Lifetime US1816848A (en) | 1929-10-03 | 1929-10-03 | Process for the production of thiocyano derivatives |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US1816848A (en) |
| FR (1) | FR702829A (en) |
| GB (1) | GB364060A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3202690A (en) * | 1962-10-08 | 1965-08-24 | Consolidation Coal Co | Preparation of thiocyanophenols |
| US3214437A (en) * | 1960-04-28 | 1965-10-26 | Eastman Kodak Co | 2-equivalent thiocyano couplers of 5-pyrazolones |
| US3472747A (en) * | 1965-08-13 | 1969-10-14 | Shell Oil Co | Electrolytic process of making organic dithionates |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5573653A (en) * | 1994-07-11 | 1996-11-12 | Sandoz Ltd. | Electrochemical process for thiocyanating aminobenzene compounds |
| CN110453241B (en) * | 2019-08-14 | 2021-08-10 | 华南理工大学 | Electrochemical preparation method of alkynyl thiocyanate |
-
1929
- 1929-10-03 US US397163A patent/US1816848A/en not_active Expired - Lifetime
-
1930
- 1930-09-30 FR FR702829D patent/FR702829A/en not_active Expired
- 1930-09-30 GB GB29274/30A patent/GB364060A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3214437A (en) * | 1960-04-28 | 1965-10-26 | Eastman Kodak Co | 2-equivalent thiocyano couplers of 5-pyrazolones |
| US3202690A (en) * | 1962-10-08 | 1965-08-24 | Consolidation Coal Co | Preparation of thiocyanophenols |
| US3472747A (en) * | 1965-08-13 | 1969-10-14 | Shell Oil Co | Electrolytic process of making organic dithionates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR702829A (en) | 1931-04-17 |
| GB364060A (en) | 1931-12-30 |
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