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Process for conversion of cyanopyridines to nicotinamides and catalyst therefor, process for preparing said catalyst

a technology of cyanopyridine and nicotinamide, which is applied in the field of process for preparing said catalyst, and process for converting cyanopyridine to nicotinamide, and can solve the problems of low catalytic activity, low nicotinamide yield, and low yield

Inactive Publication Date: 2004-09-23
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0043] 1. Nicotinamide can be produced by catalytic hydration of 3-cyanopyridine without use of alkali or acid as prior art catalyst, which necessitates an extremely complicated and cumbersome separation procedure or the product nicotinamide.
[0044] 2. The catalyst hydrated manganese dioxide has been prepared by the Redox method using potassium permanganate and manganese chloride solution in neutral medium.
[0045] 3. The catalyst used in the present invention eliminates the formation of nicotinic acid which is produced in substantial amount using the prior art catalysts (acid or alkali),
[0046] 4. The yield of nicotinamide is 91.8 mole % and the selectivity is 100% which is much higher than the catalyst report so far.
[0047] 5. The process also provides for easy and economic recovery of nicotinamide from the resulting hydrolysis effluents.

Problems solved by technology

The drawbacks are that the catalytic activity was reported to be low and the yield of nicotinamide was also low.
Further, in this process unconverted 3-cyanopyridine and ammonia were separated from the product nicotinamide by a multi step separation process which is not cost effective and is 8 very difficult procedure to get the pure product.
These are the main drawbacks of the above process.
The use of magnesium oxide catalyst for this reaction are discussed in Chemical Engineering Science, 35, 330, 1975, by C. B. Rossa and G. B. Smith. Alkaline hydrolysis of 3-cyanopyridine to nicotinamide of the Degussa process is one of the most important commercial processes adopted by some firms in India However, this process has some disadvantages i.e., the yield of nicotinamide is not very high and the conversion of 3-cyanopyridine is about 99%.
The main drawbacks of the process are that (a) the yield of isonicotinamide is less (b) it is not eco-friendly and (c) the amount of catalyst per mole of the feed for conversion is quite high.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 2

[0033] 115 ml of 0.649 molar aqueous solution of potassium permanganate was added drop wise to 225 ml of 0.5 molar aqueous solution of manganese chloride at 70.degree. C. temperature with vigorous stirring. Addition was continued for 1 hour and kept standing for 15 hours. The precipitate of manganese dioxide was filtered, washed with distilled water to make chloride ion free. The precipitate was put in an air oven at 110.degree. C. for 3 hours and weight of MnO.sub.2 was 0.189 mole.

[0034] 0.096 mole 3-cyanopyridine was dissolved in 4.55 mole of water and 0.0115 mole of MnO.sub.2 prepared by above method was added to this. The mixture was refluxed at 100.degree. C. for 13.5 hrs. The reaction mixture as cooled and filtered. The filtrate was evaporated to dryness to get solid nicotinamide 0.0879 mole. Yield of nicotinamide was 91.56 mole %.

example 3

[0035] 225 ml of 0.332 molar aqueous solution of potassium permanganate was added to 100 ml of 1.125 mole aqueous solution of manganese chloride with continuous stirring at 30.degree. C. The product manganese dioxide was filtered, washed with distilled water till free from chloride ions. The precipitated manganese dioxide was dried in an air oven at 110.degree. C. for 4 hours. Weight of manganese dioxide was 0.23 mole.

[0036] 0.096 mole of 3-cyanopyridine was dissolved in 5.556 mole water and 0.0115 mole of manganese dioxide, which was prepared by above method, was added to this solution The reaction mixture was stirred and refluxed at 100.degree. C. for 8 hours. Reaction mixture was cooled, filtered and washed with distilled water thoroughly. The filtrate was evaporated on a steam bath to dryness. After drying the weight of nicotinamide was 0.0957 mole equivalent to yield of 99.6 mole %.

example 4

[0037] 300 ml of 0.303 molar aqueous solution of manganese chloride and 60 ml 9.75 molar solution of sodium hydroxide was added simultaneously drop wise in the solution of 300 ml of 1.013 molar aqueous solution of potassium permanganate at 70.degree. C. for an hour with constant stirring and kept standing for 12 hrs. The precipitate of manganese dioxide was filtered and washed with distilled water till free from chloride ions. The precipitate was dried at 110.degree. C. for 8 hrs. Yield of manganese dioxide was 0.198 mole.

[0038] 0.096 mole 4-cyanopyridine was dissolved in 5.556 mole water and 0.0115 mole of manganese dioxide, which was prepared by above method, was added to this. The reaction mixture was refluxed at 100.degree. C. for 8 hrs in a glycerine bath. The reaction mixture was cooled, filtered and washed thoroughly with distilled water. The filtrate was evaporated on steam bath to dryness. Weight of isonicotinamide was 0.089 mole. Yield was 92.71 mole %

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Abstract

The present invention relates to an improved process for conversion of cyanopyridines to nicotinamides More particularly the present invention relates to preparation of nicotinamides and isonicotinamides which finds its usage in the preparation of anti-TB drug i.e. isoniazid and as an intermediate of vitamin B12. The present invention also relates to a process for a catalyst useful for the preparation of nicotinamide and isonicotinamide.

Description

[0001] The present invention relates to an improved process for conversion of cyanopyridines to nicotinamides. More particularly the present invention relates to preparation of nicotinamides and isonicotinamides which finds its usage in the preparation of anti-TB drug i.e. isoniazid and as an intermediate of vitamin B.sub.12. The present invention also relates to a process for a catalyst useful for the preparation of nicotinamide and isonicotinamide.[0002] Reference is made to Bull. Chem. Soc., Japan, Vol.-40, P-1660 (1967) wherein nickel oxide has been used as a catalyst for the hydration of 3-cyanopyridine to nicotinamide. The drawbacks are that the catalytic activity was reported to be low and the yield of nicotinamide was also low. Reference is also made to U.S. Pat. No. 4,008,241 to Gelbein et al of M / s. The Lummus Company (Bloom Field, N.J., USA) for the production of nicotinamide from 3-cyanopyridine by aqueous ammonia solution. The reaction temperature was 90-150.degree. C.,...

Claims

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Application Information

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IPC IPC(8): C07D213/56C07D213/81C07D213/82C07D213/84
CPCC07D213/82C07D213/81
Inventor RAY, SUBHASH CHANDRASINGH, BALDEVPRASAD, HIRALALSARKAR, PRODYOT KUMARDUTTA, PASHUPATIROY, SHYAM KISHOREBANDYOPADHYAY, ANUP KUMARSEN, RAJA
Owner COUNCIL OF SCI & IND RES
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