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Stabilizing aqueous solution of iodine chloride by adding sodium chloride

A technology of iodine chloride and sodium chloride, applied in the direction of interhalogen compounds, etc., can solve problems such as reducing the use efficiency and reducing the concentration of iodine chloride

Inactive Publication Date: 2011-02-02
GE HEALTHCARE AS
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, iodine chloride in aqueous solution may degrade over time, resulting in a lower concentration of iodine chloride and thus less efficient use of its iodinating power in the synthesis of non-ionic X-ray contrast agents

Method used

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  • Stabilizing aqueous solution of iodine chloride by adding sodium chloride

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Embodiment 1

[0019] Iodine (7.61 kg, 30 mol), hydrochloric acid (37%, 6.91 kg, 70 mol), water (0.62 kg, 35 mol) and sodium chloride (1.46 kg, 25 mol) were mixed in a reactor at 25°C. A solution of sodium chlorate (1.07 kg, 10 mol) in water (1.20 kg, 67 mol) was prepared with heating and added carefully to the reactor over a period of 2 hours with vigorous stirring. The reaction was continued at 27-30°C for 17 hours with moderate stirring. Free iodine was confirmed by extracting the sample with chloroform in the presence of hydrochloric acid (a pink color was obtained). The pH was measured to be 1.06. An aqueous iodine chloride solution (18.80 kg) having a concentration of 51.6 w / w% (relative to the reaction solution) was obtained, corresponding to a yield of 99.6%.

Embodiment 2

[0021] Iodine (2700kg, 10.6kmol), hydrochloric acid (35%, 2285kg, 21.9kmol), water (250kg, 13.3kmol) and sodium chloride (475kg, 8.1kmol) were mixed in a reactor at 20°C. Under vigorous stirring, an aqueous solution of sodium chlorate (43 w / w%, 864 kg, 2.6 mol) was carefully added to the reactor over 3-4 hours. The reaction was continued at 50°C for at least 10 hours with moderate agitation. Free iodine was confirmed by extracting the sample with chloroform in the presence of hydrochloric acid (organic phase was pink). The resulting pH is below 0.5. An aqueous solution of iodine chloride (approximately 3970 kg) was obtained at a concentration of 50 w / w% (relative to the reaction solution), corresponding to a yield of almost 100% relative to iodine.

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Abstract

This invention relates generally to non-ionic X-ray contrast agents. It further relates to the preparation of iodine chloride, a key reagent in the synthesis of non-ionic X-ray contrast agents such as iodixanol and iohexol. In particular, the iodine chloride is produced in a reaction involving iodine, sodium chlorate, and hydrochloric acid as the starting materials. The instant invention relates to a method of stabilizing aqueous iodine chloride solutions by adding about one to about four molar equivalents of sodium chloride relative to sodium chlorate to an aqueous reaction mixture of sodium chlorate, hydrochloric acid, and iodine.

Description

[0001] Cross References to Related Applications [0002] This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 61 / 227,081, filed July 21, 2009, the entirety of which The disclosure is incorporated herein by reference. technical field [0003] In general, the present invention relates to non-ionic X-ray contrast agents. Further, it relates to the preparation of iodine chloride, a key reagent in the synthesis of non-ionic X-ray contrast agents (such as iodixanol and iohexol). In particular, it concerns the stabilization of aqueous iodine chloride solutions by adding sodium chloride to the reaction mixture. Background of the invention [0004] Non-ionic X-ray contrast agents are a very important class of pharmaceutical compounds with large yields. 5-[N-(2,3-dihydroxypropyl)-acetamido]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-iso-o Phthalamide ("iohexol"), 5-[N-(2-hydroxy-3-methoxypropyl)acetamido]-N,N'-bis(2,3-dihydroxypropyl )-2,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C01B7/24
CPCC01B7/24
Inventor O·E·英沃斯塔德
Owner GE HEALTHCARE AS
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