US1816848A - Process for the production of thiocyano derivatives - Google Patents

Process for the production of thiocyano derivatives Download PDF

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Publication number
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
production
parts
mixture
derivatives
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US397163A
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Helwig Edward Leslie
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Priority to US397163A priority Critical patent/US1816848A/en
Priority to GB29274/30A priority patent/GB364060A/en
Priority to FR702829D priority patent/FR702829A/fr
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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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US397163A 1929-10-03 1929-10-03 Process for the production of thiocyano derivatives Expired - Lifetime US1816848A (en)

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
GB29274/30A GB364060A (en) 1929-10-03 1930-09-30 Electrolytic production of thiocyanide derivatives
FR702829D FR702829A (fr) 1929-10-03 1930-09-30 Production électrolytique de dérivés du thiocyanure

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

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US (1) US1816848A (fr)
FR (1) FR702829A (fr)
GB (1) GB364060A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
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
CN117038890A (zh) * 2023-08-09 2023-11-10 浙江华宇钠电新能源科技有限公司 一种过渡金属氧化物修饰的高首效、高容量硬碳负极材料

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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 (zh) * 2019-08-14 2021-08-10 华南理工大学 一种炔基硫氰酸酯的电化学制备方法

Cited By (4)

* Cited by examiner, † Cited by third party
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
CN117038890A (zh) * 2023-08-09 2023-11-10 浙江华宇钠电新能源科技有限公司 一种过渡金属氧化物修饰的高首效、高容量硬碳负极材料

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Publication number Publication date
FR702829A (fr) 1931-04-17
GB364060A (en) 1931-12-30

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