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A new technology for the synthesis of serinol

A technology of serinol and propylene glycol, which is applied in chemical synthesis, pharmaceutical and chemical fields, can solve the problems of low product purity, increased manufacturing cost, and low yield of serinol, and achieve the effect of reducing manufacturing cost

Inactive Publication Date: 2017-12-12
TSINGRUN SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above-mentioned prior art uses 2-nitro-1,3-propanediol sodium salt as the reaction raw material. During the reaction, the sodium salt easily covers the surface of the catalyst, affects the activity of the catalyst, and causes the catalyst to be deactivated, so that the reaction cannot be carried out completely, resulting in silk Amino alcohol yield is low, product purity is not high
In addition, the catalyst used therein cannot be reused, making the manufacturing cost increase and the economic benefit low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Step 1: Preparation of reaction raw material 2-nitro-1,3-propanediol methanol solution

[0023] Add 124g of nitromethane and 126g of paraformaldehyde to 750g of methanol, and control the temperature at 25°C~35°C to obtain 1000g of 25% 2-nitro-1,3-propanediol solution.

[0024] Step 2: Prepare Serinol

[0025] Add 3.5 g of 5% palladium / carbon to 1000 g of the 25% 2-nitro-1,3-propanediol solution prepared above, continuously inject 90 L of hydrogen gas at a pressure of 0.5 MPa, and keep warm at 70° C. for 3 hours to obtain a serinol solution. Palladium / charcoal was filtered off, washed and reused.

[0026] Step 3: High-purity serinol is distilled out by high vacuum

[0027] The serinol solution is pumped into a high-vacuum still, vacuumed to 20Pa, and the methanol is evaporated for recycling. The yield of serinol is 80.2%.

Embodiment 2

[0029] Step 1: Preparation of 2-nitro1,3-propanediol sodium salt

[0030] Add 124g of nitromethane and 126g of paraformaldehyde to 320g of methanol, add dropwise 482g of 20% sodium hydroxide methanol solution after complete depolymerization, control the temperature at 20°C~35°C, filter and dry to obtain 2-nitro-1,3-propylene glycol sodium Salt 295g.

[0031] Step 2: Preparation of 2-nitro-1,3-propanediol solution

[0032] Add 750g of methanol to the reaction kettle, add 295g of 2-nitro-1,3-propanediol sodium salt, and 108g of ammonium chloride, stir for 1 hour, and filter to obtain 1000g of 25% 2-nitro-1,3-propanediol solution.

[0033] Step 3: Catalytic hydrogenation of 2-nitro-1,3-propanediol solution to produce serinol

[0034] Add 3.75 g of 5% palladium / carbon to 1000 g of the 25% 2-nitro-1,3-propanediol solution prepared above, continuously inject 70 L of hydrogen gas at a pressure of 0.5 MPa, and keep warm at 70°C for 3 hours to prepare a serinol solution. Palladium / c...

Embodiment 3

[0038] Step 1: Preparation of 2-nitro1,3-propanediol sodium salt

[0039] Add 124g of nitromethane and 126g of paraformaldehyde to 320g of methanol, add dropwise 482g of 20% sodium hydroxide methanol solution after complete depolymerization, control the temperature at 20°C~35°C, filter and dry to obtain 2-nitro-1,3-propylene glycol sodium Salt 295g.

[0040] Step 2: Preparation of 2-nitro-1,3-propanediol solution

[0041] Add 2250g of methanol to the reaction kettle, add 295g of 2-nitro-1,3-propanediol sodium salt, and 108g of ammonium chloride, stir for 1 hour, and filter to obtain 2,500g of 10% 2-nitro-1,3-propanediol solution.

[0042] Step 3: Catalytic hydrogenation of 2-nitro-1,3-propanediol solution to produce serinol

[0043] 2500 g of 10% 2-nitro-1,3-propanediol methanol solution was added with 2.5 g of 5% palladium / carbon catalyst, 70 L of hydrogen gas was continuously introduced, the pressure of hydrogen gas was 1 MPa, and the temperature was kept at 70 ° C for 3 h...

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Abstract

A preparation method of serinol belongs to the technical field of preparation of serinol by reduction reaction. Serinol is an important intermediate of nonionic X-ray contrast agent iopamidol. In the invention, nitromethane and paraformaldehyde are used as raw materials, hydrogen is used as a reducing agent, and palladium / carbon is used as a catalyst to prepare serine alcohol. The method of the invention has mature technology, simple equipment, high serinol yield, and has been industrialized.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a new process of serinol synthesis technology, especially a technology of hydrogenation reduction of nitro compounds into amino compounds, which belongs to the technical field of chemical synthesis. Background technique [0002] Serinol (2-amino-1,3-propanediol) is a pharmaceutical intermediate used to synthesize the main raw material of non-ionic contrast agent iopamidol (iobemol). It is mainly used as a diagnostic reagent for the blood system, lymphatic system, urinary system, and nervous system, and has been widely used in foreign developed countries. At present, most hospitals in my country still use ionic contrast agents. Compared with ionic contrast agents, non-ionic contrast agents have many advantages: low osmotic pressure, good tolerance, stable performance, and minimal side effects. Therefore, it is a trend to replace ionic contrast agents with non-ionic on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/10C07C213/02C07C201/12C07C205/15
Inventor 不公告发明人
Owner TSINGRUN SCI & TECH CO LTD
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