Nicotinic Acid Powder CAS 59-67-6

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Nicotinic acid powder, belonging to the vitamin B group, is also known as niacin, vitamin B3 and anti leprosy factor. Its molecular formula is C6H5NO2, CAS 59-67-6 and its chemical name is pyridine-3-formic acid. It has good thermal stability and can be sublimated. Nicotinic acid is often purified by sublimation in industry. Nicotinic acid is white crystal or white crystalline powder, soluble in water, mainly present in animal viscera and muscle tissue, and also trace in fruit and egg yolk. It is one of the 13 essential vitamins for human body. Nicotinic acid is mainly used as feed additive, which can improve the utilization rate of feed protein, milk yield of dairy cows, and the yield and quality of fish, chicken, duck, cattle, sheep and other poultry and livestock meat. Nicotinic acid is also a widely used pharmaceutical intermediate. It can be used as raw material to synthesize a variety of medicines, such as nikethamide and nicotinic inositol ester. In addition, nicotinic acid also plays an irreplaceable role in luminescent materials, dyes, electroplating industries and other fields.

Nicotinic acid powder has 3 commodity specifications, namely food grade, feed grade and pharmaceutical grade. Nicotinic acid is mainly used as a nutritional additive (water-soluble vitamin) of feed, as well as an intermediate of food, medicine and dye, and as an additive of electroplating solution and biochemical reagent.

 

1. Application of nicotinic acid in pharmaceutical synthesis:

Nicotinic acid, as a drug, can prevent and treat skin diseases and similar vitamin deficiencies, and has the effect of expanding blood vessels. It is used to treat peripheral nervous spasm, arteriosclerosis and other diseases. Nicotinic acid can also be used as a medical intermediate to synthesize a variety of amide and ester drugs with important medical uses, such as nicotinamide can be used to treat gastrointestinal diseases, hydroxymethylamine nicotinate is a good drug to protect the liver, promote bile and inhibit bacteria, and nicotinamide, as a highly effective molluscicidal drug, can be used to prevent and treat schistosomiasis; Nicotinic acid and tromethamine can be synthesized to treat circulatory disorders, vitamin B deficiency, glossitis, hypertension and other diseases; Nikethamide, synthesized from nicotinic acid and diethylamine, is a central nervous stimulant used to treat central nervous respiratory and circulatory system failure; Nicotinic acid inositol ester and Mizhiling produced by the reaction of nicotinic acid and alcohol are drugs for treating hyperlipidemia, coronary heart disease, migraine, peripheral vascular disorders, etc.

 

2. Application of nicotinic acid as auxiliary agent:

Nicotinic acid is an indispensable food and feed additive for human and animal growth and development. Therefore, niacin is widely used as an additive for cakes, dairy products, corn flour, etc; Nicotinic acid can also be used together with vitamins to replace part of nitrite as a deodorant or preservative for meat products. In addition, nicotinic acid can also be used as a preservative for vegetables. Because a large part of nicotinic acid in cereal feed exists in the form of complex, it cannot be directly absorbed by animals. Therefore, the method widely used in the world is to add industrial synthetic nicotinic acid into feed. The feed feeding test proved that the artificial synthetic nicotinic acid can be 100% absorbed and utilized by animals, and the obvious weight gain effect can be achieved in a short period of time. According to the situation of the breeding industry in China, the standard for adding niacin in China is: 9-24mg per kg of pig feed (dry basis) and 10-27mg per kg of chicken feed (dry basis).

 

3. Food additives:

Nicotinic acid belongs to the vitamin B family and participates in the lipid metabolism, oxidation process and anaerobic decomposition process of the human body. Nicotinic acid can be converted from tryptophan in the body. Nicotinic acid deficiency is not easy to occur in the human body. However, when the staple food does not contain nicotinic acid or there are substances that can decompose nicotinic acid in the staple food, it is easy to cause rough skin disease due to lack of nicotinic acid. Therefore, niacin is widely used in flour processing, dairy products and corn flour production. Adding a certain amount of niacin in food can effectively prevent the occurrence of this kind of disease.

 

4. Feed additives:

Nicotinic acid is an indispensable substance for animal growth and development. Nicotinic acid in cereal feed mainly exists in the form of combination, which is difficult for animals to absorb. Therefore, it is necessary to manually add synthetic nicotinic acid to feed.

Adding proper amount of nicotinic acid to the feed can rapidly increase the weight of piglets (chickens). Feeding nicotinic acid feed to laying hens can improve their egg production rate, and make eggs also contain a certain amount of nicotinic acid, thus improving the nutritional value.

5. Reactive dye:

Because nicotinic acid can make the fiber dyeing lasting, wide application range and good uniformity, nicotinic acid is outstanding in the dye industry and becomes an intermediate of a variety of reactive dyes. In 1984, the Japanese Chemical Pharmaceutical Company introduced a weakly basic nicotinic acid triazine reactive dye.

 

6. Daily chemical industrial products:

In the daily chemical industry, nicotinic acid can be combined with other daily chemical raw materials to form products with excellent performance, such as hair dyeing auxiliaries, detergents, etc.

7. Other applications:

Nicotinic acid is an important chemical additive and corrosion inhibitor. It can be used as an antioxidant and anti fogging agent in photosensitive materials. In electroplating, nicotinic acid is also an excellent brightening additive. As long as 1-10g nicotinic acid is added to each liter of electroplating solution, it will have a significant effect.

Nicotinic acid is used as antioxidant and anti fogging agent in photosensitive materials. Adding 0.1% aqueous nicotinic acid solution to the photosensitive lotion can increase the stability of the photosensitive material to light; Adding 5-20mL 0.1% nicotinic acid aqueous solution to each milliliter of photosensitive lotion can reduce the fog of photosensitive materials.

Nicotinic acid powder was first synthesized in the laboratory in 1867, but it was not until the 1930s that nicotinic acid was truly industrialized. Nicotinic acid was synthesized by oxidizing nicotine at the beginning of industrialization. Later, most of the alkyl pyridines such as quinoline, 2-methyl-5-ethylpyridine and 3-methylpyridine were used as raw materials to synthesize nicotinic acid through chemical or electrochemical oxidation. According to the classification of synthesis methods, it is generally divided into reagent oxidation method with nitric acid, potassium permanganate and other oxidants, ammonia oxidation method with ammonia and air as oxidants, air direct oxidation method, electrolytic oxidation method, biological transformation method and pyridine hydroxylation method. According to the classification of main raw materials, there are nicotine, 6-hydroxyquinoline, naphthalene, pyridine, 3-pyridylaldehyde, 3-methylpyridine, 2-methyl-5-ethylpyridine. The 3-methylpyridine route is widely used.

(1) Nitric acid oxidation method:

With nitric acid as oxidant, the mixture of nitric acid aqueous solution and MEP is introduced into a titanium tubular reactor, and the mixture is reacted at 330 ℃ and 29MPa for 8h before separation and refining to obtain pure niacin.

(2) Air oxidation method:

The synthesis of nicotinic acid by direct oxidation of 3-methylpyridine with air as oxidant has attracted much attention in recent years due to its high efficiency and low cost. This method was first used to oxidize alkyl pyridine with air added with catalyst. Later, it was improved to synthesize nicotinic acid by gas-solid catalytic oxidation of 3-methylpyridine for 3h at 350 ℃ - 400 ℃ in a fixed bed reactor. The catalyst can be used for a long time. Nicotinic acid can be obtained by direct oxidation of 3-methylpyridine with air, which is economical. If the one-way conversion rate can be improved, it will become a low cost and high efficiency production process. Its core is the development of high efficiency, low cost and long life catalysts, which mostly stay in the laboratory research stage, and there is no report of successful industrialization.

Electrolytic oxidation

Electrolytic oxidation is widely used in production because of its mild conditions, low cost of oxidants, low toxicity and pollution, and low production cost. Similar to the chemical oxidation method, nicotinic acid is usually synthesized by electrochemical oxidation of alkyl pyridine compounds as raw materials, but the disadvantage is that the electrolysis efficiency is low, mainly because the isolation membrane used in the electrolytic cell has poor selective permeability, which greatly restricts the industrial production of this method.

(1) Ammonia oxidation method:

The method uses 3-methylpyridine or MEP as raw material, conducts gas-solid catalytic oxidation with ammonia and oxygen in a certain proportion in the catalyst bed, generates 3-cyanopyridine, and obtains nicotinic acid by hydrolysis and purification. The single pass conversion of 3-methylpyridine was increased to 99%, and the selectivity of 3-cyanopyridine hydrolysis to nicotinic acid powder was also increased to 99%.

The raw material of ammoxidation method is 3-methylpyridine, the by-product with the highest yield ratio in the production of pyridine base. It is cheap, widely sourced, and the reaction conditions are relatively mild. It can be carried out under normal or low pressure conditions. The production is safe and reliable. The existing technology has a high one-way conversion rate, good selectivity, and high purity of the product. It can realize continuous synthesis and is suitable for large-scale industrial production, It has become one of the most widely used methods for preparing nicotinic acid in industry.

(2) Biosynthesis:

Enzymatic hydrolysis of nitriles has incomparable advantages over chemical methods. It has the advantages of high efficiency, good selectivity, mild reaction conditions, less environmental pollution, low cost, and high optical purity of products. It is in line with the development direction of green chemistry. A Swiss company has industrialized the synthesis of B group vitamin nicotinic acid by enzyme catalysis. Hideki Yamada of Kyoto University in Japan and others produced nicotinic acid with Rhodococcus rhodochrous J1 strain.

Nicotinic acid powder is an important organic synthetic intermediate with wide application value. There are three main methods for obtaining niacin: (1) extraction method; (2) Biosynthetic method; (3) Chemical synthesis method.
Niacin was first synthesized in the laboratory in 1867, but it was not until the 1930s that it was truly industrialized. Initially, industrialization synthesized niacin by oxidizing nicotine, but later mostly used alkyl pyridines such as quinoline, 2-methyl-5-ethylpyridine, and 3-methylpyridine as raw materials to synthesize niacin through chemical or electrochemical oxidation. From the classification of synthesis methods, they are generally divided into reagent oxidation methods using nitric acid, potassium permanganate, etc. as oxidants, ammonia oxidation methods using ammonia and air as oxidants, direct air oxidation methods, electrolytic oxidation methods, biotransformation methods, and pyridine hydroxylation methods. From the main raw material classification, there are nicotine, 6-hydroxyquinoline, naphthalene, pyridine, 3-pyridinecarboxaldehyde, 3-methylpyridine, 2-methyl-5-ethylpyridine, and the 3-methylpyridine route is widely used.

1. Nitric acid oxidation method
Using nitric acid as the oxidant, a mixture of nitric acid aqueous solution and MEP was introduced into a titanium tubular reactor. The reaction was carried out at 330 ℃ and 29 MPa for 8 hours before separation and purification to obtain pure niacin.
This method was developed in the early stages due to its wide range of oxidant sources, flexible operation, easy control, and low one-time investment. However, due to its high consumption of oxidants, harsh reaction conditions, high requirements for mechanical and corrosion resistance of equipment, large output of "three wastes", low yield, poor appearance and quality of products, and high cost, it is not suitable for large-scale industrial production. This method has been phased out in industrialized countries such as the United States, Western Europe, and Japan.
2. Air oxidation method
The air oxidation method, which uses air as an oxidant to directly oxidize 3-methylpyridine to synthesize nicotinic acid, has attracted much attention in recent years due to its high efficiency and low cost. This method was originally carried out by introducing air into alkyl pyridine with a catalyst for oxidation reaction. Later, it was improved to synthesize nicotinic acid using 3-methylpyridine as raw material in a fixed bed reactor at 350 ℃ -400 ℃ for 3 hours through gas-solid phase catalytic oxidation reaction. Catalysts can be used for a long time by directly oxidizing 3-methylpyridine with air to obtain nicotinic acid, which has good economic efficiency. If the one-way conversion rate can be improved, it will become a low-cost and efficient production process. Its core lies in the development of efficient, low-cost, and long-life catalysts, which are mostly in the laboratory research stage and have not yet been successfully industrialized.
3. Electrolytic oxidation method
The electrolytic oxidation method is widely used in production due to its mild conditions, low cost of oxidants, low toxicity and pollution, and low production cost. Similar to the chemical oxidation method, alkyl pyridine compounds are often used as raw materials to synthesize nicotinic acid through electrochemical oxidation. However, the drawback is the low electrolysis efficiency, mainly due to the poor permeability of the isolation membrane used in the electrolytic cell, which greatly limits the industrial production of this method.

1. Ammonia oxidation method
This method uses 3-methylpyridine or MEP as raw materials, and performs gas-solid phase catalytic oxidation with ammonia and oxygen in a certain proportion in the catalyst bed to generate 3-cyanopyridine, which is hydrolyzed and purified to obtain niacin. This process increases the one-way conversion rate of 3-methylpyridine to 99%, and the selectivity of 3-cyanopyridine hydrolysis to prepare nicotinic acid also increases to 99%.
The raw material of ammonia oxidation method is 3-methylpyridine, which has the highest proportion of by-products produced in the production process of pyridine base. It is inexpensive, widely available, and the reaction conditions are relatively mild. It can be carried out under normal pressure or low pressure conditions, and the production is safe and reliable. The existing technology has a high one-way conversion rate, good selectivity, and high product purity. It can achieve continuous synthesis and is suitable for large-scale industrial production. Nicotinic acid powder has become one of the most widely used methods for preparing niacin in industry.
2. Biological synthesis method
The enzymatic hydrolysis of nitrile has unparalleled advantages over chemical methods, including high efficiency, good selectivity, mild reaction conditions, low environmental pollution, low cost, and high optical purity of the product, which is in line with the development direction of green chemistry. Swiss companies have already industrialized the synthesis of B-complex vitamin niacin using enzymatic catalysis. Hideaki Yamada and others from Kyoto University in Japan produced niacin using Rhodococcus rhodochrous J1 strain.

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