Preparation method and application of isoamyl nitrite

Background and overview

Isoamyl nitrite, also known as nitrosoamyl and amyl nitrate, is a light yellow clear and transparent liquid, smells like ether and has a fruity fragrance. Volatile at room temperature and easy to burn. Almost insoluble in water, can be mixed with ethanol, ether, chloroform or benzene. It will decompose when exposed to light and air. It is an anti-angina drug with the fastest onset and the shortest duration. It is a nitrite short-acting vasodilator. Its pharmacological action is similar to that of nitroglycerin. , Peripheral resistance decreases, blood pressure decreases, venous return to the heart decreases, and cardiac output decreases, thereby reducing myocardial oxygen consumption, resisting angina pectoris, and effectively stimulating libido. Because it is rapidly hydrolyzed in the gastrointestinal tract, this product is invalid when taken orally. Usually, the drugs used in clinical are made into a volatile liquid inhaler by the pharmaceutical factory. , the effect lasts only 3 to 10 minutes, its anti-angina effect is similar to that of nitroglycerin, but the inhaled dose of this product is difficult to control, and the adverse reactions are large, which is its disadvantage. Because it often causes severe headache, severe hypotension and tachycardia, it is rarely used in the clinical treatment of angina pectoris and biliary colic, and is gradually replaced by other nitrates.

Preparation

The tubular reactor in this embodiment is a single tube, with a tube length of 5 m and a tube diameter of 1 mm. The molar ratio of isoamyl alcohol, concentrated hydrochloric acid and sodium nitrite is 1:1.5:1.07. Pre-prepared isoamyl alcohol (880 g, 10 mol), concentrated hydrochloric acid (1.52 kg, HCl content 15 mol), sodium nitrite aqueous solution (1845 g, sodium nitrite content 10.7 mol). The above-mentioned isoamyl alcohol and concentrated hydrochloric acid are evenly mixed and stored in the first liquid storage container, and the above-mentioned sodium nitrite aqueous solution is stored in the second liquid storage container. The solutions in the first liquid reservoir and the second liquid reservoir are continuously transported to the static mixer for mixing through the first metering pump and the second metering pump respectively, and the first throttle valve and the second throttle valve are controlled at the same time to control the material The flow rate, the feed molar ratio of concentrated hydrochloric acid and sodium nitrite is 1:1.5:1.07, after mixing in the static mixer, the reaction is carried out in a tubular reactor at 0° C. to produce isoamyl alcohol. After staying for 200 s, the reaction liquid after the reaction was completed entered the separatory tank, and the crude product was separated and extracted to finally obtain 1.12 kg of isoamyl nitrite, with a yield of 96% and a purity of 97%.

Use

Cyanide Poisoning Antidote

The pharmacological action is the same as that of sodium nitrite. Isoamyl nitrite is also an oxidant, which can oxidize hemoglobin into high iron (Fe³⁺) hemoglobin, which combines with cyanide ions to generate cyanide methemoglobin and eliminates the oxidation of cytochrome by free cyanide ions in the blood. In addition, it can release the cyanide ions combined with cytochrome oxidase, so that the activity of the enzyme and the respiratory function of the tissue can be restored. Radical (SCN-) excreted from the body, thus playing a role in the treatment of cyanide poisoning. This product is administered by inhalation method, and it is rapidly absorbed in the lungs after inhalation. It takes effect after 10 to 30 seconds, and the effect lasts for 3 to 5 minutes. For emergency use, intravenously inject sodium nitrite after symptoms improve.

For the synthesis of spices, drugs and diazo compounds, also used as oxidants, solvents

References

【1】CN109912421,2019, A