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Thiol-containing compounds for the removal of elements from contaminated milieu and methods of use

A technology of compounds and polymers, applied in the field of compounds of metals and main group elements

Inactive Publication Date: 2012-07-25
UNIV OF KENTUCKY RES FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Thus, existing approved heavy metal binders suffer from a number of deficiencies in their overall chemical profile, which could be improved by synthesizing ones with safer excretion properties (e.g., higher affinity for metals and / or main group elements). high and excreted in feces rather than urine) better designed true chelators

Method used

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  • Thiol-containing compounds for the removal of elements from contaminated milieu and methods of use
  • Thiol-containing compounds for the removal of elements from contaminated milieu and methods of use
  • Thiol-containing compounds for the removal of elements from contaminated milieu and methods of use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156] This example details the synthesis of one non-limiting embodiment of AB9, the scheme is as follows:

[0157]

[0158] / or will be obtained from Sigma- 0.78 g of L-cysteine ​​hydrochloride (5.0 mmol) was dissolved in 100 ml of deionized water. 1.02 g of triethylamine (10 mmol, 1.4 ml) (hereinafter referred to as "TEA"), and obtained from 0.5 g (2.5 mmol) of isophthaloyl chloride were each dissolved in Acros 20 ml of tetrahydrofuran (hereinafter referred to as "THF"). TEA dissolved in THF was slowly added to the stirred deionized water solution of L-cysteine ​​hydrochloride in the flask under nitrogen flow. After stirring for 5-10 minutes, isophthaloyl chloride dissolved in THF was slowly added to the flask. As the reaction proceeded, the reaction mixture turned pale yellow. The reaction mixture was stirred for an additional 16-18 hours. After 16-18 hours, the aqueous layer was extracted with 100 mL of ethyl acetate. Subsequently, the ethyl acetate layer was...

Embodiment 2

[0160] This example details the synthesis of a non-limiting embodiment of MEAB9, the scheme is as follows:

[0161]

[0162] 2.57 g of L-cysteine ​​methyl ester hydrochloride (15 mmol) was dissolved in 150 ml of chloroform. 1.52 g of TEA (15 mmol, 2.07 mL) was dissolved in 25 mL of chloroform, and 1 g of isophthaloyl chloride (5 mmol) was dissolved in 40 mL of chloroform. The TEA solution and the isophthaloyl chloride solution were slowly added to the L-cysteine ​​methyl ester hydrochloride solution. The reaction was stirred for 24 hours. Subsequently, the reaction solution was filtered, and the filtrate was washed with 200 ml of 10% Wash with hydrochloric acid three times. After washing, the chloroform layer was filtered again and washed with anhydrous Na 2 SO 4 dry. Chloroform was removed under vacuum to obtain a highly viscous oily liquid product. The oily liquid was redissolved in chloroform, and the chloroform was removed under vacuum. This step was repeated t...

Embodiment 3

[0164] This example details the synthesis of a non-limiting embodiment of EEAB9 as follows:

[0165]

[0166] 2.72 g of L-cysteine ​​ethyl ester hydrochloride (15 mmol) was dissolved in 150 ml of chloroform. 1.48 g of TEA (15 mmol, 2.02 mL) was dissolved in 25 mL of chloroform, and 1 g of isophthaloyl chloride (5 mmol) was dissolved in 40 mL of chloroform. The TEA solution and the isophthaloyl chloride solution were slowly added to the L-cysteine ​​ethyl ester hydrochloride solution. The reaction was stirred for 24 hours. Then filter the reaction solution, the filtrate with 1.5 liters of 20% Wash with hydrochloric acid three times. After washing, the chloroform layer was filtered again and washed with anhydrous Na 2 SO 4 dry. Chloroform was subsequently removed under vacuum to obtain a highly viscous oily liquid product. The oily liquid was redissolved in chloroform, which was then removed under vacuum. This step was repeated twice and the resulting white solid was...

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Abstract

Sulfur-containing ligands and methods of their utilization for binding metals and / or main group elements and removing them from fluids, solids, gases and / or tissues are disclosed. The ligands are of the general structure (A): or structure (B) where R1 comprises benzene, pyridine, pyridin-4-one, naphthalene, anthracene, phenanthrene or alkyl groups, R2 comprises hydrogen, alkyls, aiyls, a carboxyl group, carboxylate esters, organic groups or biological groups, R3 comprises alkyls, aryls, a carboxyl group, carboxylate esters, organic groups or biological groups, X comprises hydrogen, lithium, sodium, potassium, rubidium, cesium, francium, alkyls, aryls, a carboxyl group, carboxylate esters, thiophosphate, N-acetyl cysteine, mercaptoacetic acid, mercaptopropionic acid, thiolsalicylate, organic groups or biological groups, n independently equals 1-10, m = 1 -6, Y comprises hydrogen,; polymers, silicas or silica supported substrates, and Z comprises hydrogen, alkyls, aryls, a carboxyl group, carboxylate esters, a hydroxyl group, NH2, HSO3, halogens, a carbonyl group, organic groups, biological groups, polymers, silicas or silica supported substrates.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application Serial Nos. 61 / 246,278, 61 / 246,282, and 61 / 246,360, all of which were filed September 28, 2009, the entire disclosures of which are incorporated herein in their entirety. technical field [0003] The present invention relates to compounds for the covalent binding of a wide range of metals and main group elements, and more particularly to sulfur-containing ligands and the use of these sulfur-containing ligands to remove pollutants from solids, liquids and gases. Background technique [0004] Heavy metal and main group element pollution is an existing and growing global problem. Over the past few decades, federal and state governments have enacted environmental regulations to protect the quality of surface water and groundwater from contamination. In response to these regulatory requirements, a number of products have been developed to precipitate pollutants...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/42A61K31/194A61K31/166A61K31/095A61P39/04
CPCB01D2253/25C07C327/30A61K31/216A61K31/198C07B2200/11B01D53/64C07C323/42B01D2253/106B01D2257/602C07C323/60C07C323/59C07F7/1836A61K31/695B01D2257/60A61K31/795C07F7/1804A61P39/04A61P43/00
Inventor 博伊德·E·黑利大卫·A·阿特伍德
Owner UNIV OF KENTUCKY RES FOUND
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