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US 2017/0341955 A1Published application
Cross-linked polymeric resin and methods for wastewater treatment
AssigneeKing Fahd University of Petroleum and Minerals
InventorsOluwafemi S. AKINTOLA, Tawfik Abdo Saleh Awadh, Mazen Mohammad Khaled, Othman Charles Sadeq Al Hamouz
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Abstract
Cross-linked polymeric resins from anilines linked together with dithiocarbamate alkyl chains. A process for producing the cross-linked polymeric resins by Mannich-type polycondensation of anilines and diaminoalkanes linked together by an aldehyde and subsequent conversion of one or more amine functionalities to dithiocarbamate moieties. In addition, a method for removing heavy metals, such as Hg(II) from aqueous solution via contacting and treatment with the cross-linked polymeric resins.
Claims20
1:
- A cross-linked polymeric resin of formula (I)
- or a salt, solvate, tautomer or stereoisomer thereof;
- wherein, each R1 is independently —H, —CS2−Z+, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl with the proviso that at least one R1 is —CS2−Z+;
- each R2 is independently —H, —F, —Cl, —Br, —CN, —OR3, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;
- each R3 is independently —H, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;
- Z is —H or an alkali metal counter ion;
- n is a positive whole number in the range of 2-16;
- X is a positive whole number;
- and
- A1 forms a bond to A2.
7 more elements
2:
- The cross-linked polymeric resin of claim 1, wherein each R1 is —CS2−Z+.
3:
- The cross-linked polymeric resin of claim 1, wherein the compound of formula (I) is
- or a salt, solvate, tautomer or stereoisomer thereof;
- wherein, n is a positive whole number in the range of 4-12;
- X is a positive whole number;
- and
- A1 forms a bond to A2.
3 more elements
4:
- The cross-linked polymeric resin of claim 1, which is in the form of polyhedral nanometer sized structures having an average width in the range of 10 to 30 nm and an average height in the range of 4-16 {acute over (Å)}.
5:
- The cross-linked polymeric resin of claim 1, which has a BET surface area in the range of 2.0 to 15.0 m2 g−1.
6:
- A process for producing the cross-linked polymeric resin of claim 1, comprising:
- reacting an aniline compound with a diaminoalkane compound in the presence of an aldehyde to form the cross-linked polymeric resin wherein R1 is —H;
- and
- reacting the cross-linked polymeric resin wherein R1 is —H with carbon disulfide in the presence of an alkali metal hydroxide to form the cross-linked polymeric resin wherein at least one R1 is CS2−Z+.
1 more element
7:
- The process of claim 6, wherein the molar ratio of the aldehyde to the aniline compound is in the range of 4:1 to 8:1.
8:
- The process of claim 6, wherein the molar ratio of the diaminoalkane compound to the aniline compound is in the range of 1:1 to 5:1.
9:
- The process of claim 6, wherein the aniline compound is aniline, the aldehyde is paraformaldehyde and the diaminoalkane compound is at least one selected from the group consisting of 1,4-diaminobutane, 1,6-diaminohexane, 1,8-diaminooctane, 1,10-diaminodecane, and 1,12-diaminododecane.
10:
- A method for removing a heavy metal from an aqueous solution, comprising:
- contacting the cross-linked polymeric resin of claim 1 with the aqueous solution comprising at least one heavy metal;
- and
- adsorbing the heavy metal onto the cross-linked polymeric resin to form a heavy metal loaded cross-linked polymeric resin.
1 more element
11:
- The method of claim 10, further comprising:
- desorbing the heavy metal from the heavy metal loaded cross-linked polymeric resin by treating with an acid to reform the cross-linked polymeric resin;
- and
- reusing the cross-linked polymeric resin up to 15 times without a loss in adsorption capacity.
1 more element
12:
- The method of claim 10, wherein the heavy metal is at least one ion selected from the group consisting of Hg, Cu, Zn, Mn, Fe, and Ni.
13:
- The method of claim 10, wherein the heavy metal is Hg(II).
14:
- The method of claim 10, wherein the cross-linked polymeric resin has an adsorption capacity in the range of 15-35 mg of heavy metal per g of the cross-linked polymeric resin.
15:
- The method of claim 10, wherein the aqueous solution has a pH in the range of 2 to 8.
16:
- The method of claim 10, wherein the aqueous solution has an initial heavy metal concentration in the range of 0.05 mmol L−1 to 1.0 mmol L−1.
17:
- The method of claim 10, wherein the cross-linked polymeric resin is present at a concentration in the range of 0.02-5.0 g of resin per L of the aqueous solution during the contacting.
18:
- The method of claim 10, wherein the cross-linked polymeric resin is contacted with the aqueous solution for 0.1 to 24 hours.
19:
- The method of claim 10, wherein the contacting is performed at a temperature in the range of 20° C. to 60° C.
20:
- The method of claim 10, wherein greater than 90% of the total mass of the heavy metal is removed from the aqueous solution.