Method for removing fluorinated organic compounds from contaminated fluids, and adsorbent component and adsorbent kit used therefor

Patent metadata

Field	Value
Publication number	US-10196286-B2
Application number	US-201414782259-A
Country	US
Kind code	B2
Filing date	Apr 3, 2014
Priority date	Apr 5, 2013
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

A method may be provided for removing fluorinated organic compounds from contaminated fluids by means of a kit that comprises a first and a second adsorbent component, or only by means of the first adsorbent component alone. The second adsorbent component is a solid adsorbent; the first adsorbent component is a chemical compound that contains a lipophilic group and a hydrophilic group, or contains such a compound in dissolved form, wherein the hydrophilic group contains at least one cationic group and wherein the lipophilic group is selected from alkyl groups that comprise at least one octylene unit, from aryl groups, and from aralkyl groups. The contaminated fluid may be brought in contact with the first adsorbent component, and optionally the fluid is also brought in contact with the second adsorbent component. The adsorbent component(s) may be removed from the fluid together with the adsorbed fluorinated organic compounds.

First claim

The invention claimed is:

1. A kit for separation of fluorinated organic compounds from contaminated fluids, the kit comprising a first adsorbent component and a second adsorbent component, wherein the second adsorbent component is a solid adsorbent and the first adsorbent component is a chemical compound having a formula R 1 -E-L-X, R 1 -L-E-X or R 1 -E-X, or includes a chemical compound having a formula R 1 -E-L-X, R 1 -L-E-X or R 1 -E-X in dissolved form
wherein R 1 is a lipophilic group including an alkyl group comprising at least one octylene unit, aryl groups, or aralkyl groups,
wherein E is a hydrophilic group comprising at least one cationic group, the cationic group comprising an amine, an organic substituted ammonium, or a metal complex,
wherein L is a linker, and
X is a reactive group that chemically reacts with the contaminated fluid, or comprises hydroxy groups,
wherein the first adsorbent component is furthermore present either in dissolved form or as a liquid, and
wherein a flocculant is included in addition to the first and second adsorbent component.

2. A method for separation of fluorinated organic compounds from contaminated fluids by means of an adsorbent component comprising the following steps:
providing the adsorbent component, wherein the adsorbent component is a chemical compound comprising a lipophilic group and a hydrophilic group, or the adsorbent component comprises the chemical compound in dissolved form, wherein the hydrophilic group includes at least one cationic group,
wherein the lipophilic group is selected from among alkyl groups comprising at least one octylene unit, aryl groups, or aralkyl groups, and

wherein the at least one cationic group comprises an amine, an organic substituted ammonium, an organic substituted phosphonium, or a metal complex;
bringing the contaminated fluid into contact with the adsorbent component, wherein the contaminated fluid includes the adsorbent component at least partially in dissolved form; and
separating the adsorbent component with an amount of adsorbed fluorinated organic compounds from the contaminated fluid.

3. The method of claim 2 , wherein a flocculant is added prior to the separation of the adsorbent component with an amount of adsorbed fluorinated organic compounds from the contaminated fluid.

4. A method comprising:
separating a fluorinated organic compound from a contaminated fluid with an adsorbent compound having a formula R 1 -E-L-X, R 1 -L-E-X or a formula R 1 -E-X, wherein
R 1 is a lipophilic group selected from among alkyl groups comprising at least one octylene unit, aryl groups and aralkyl groups,
E is a hydrophilic group including at least one cationic group, wherein the cationic group comprises an amine, an organic substituted ammonium, an organic substituted phosphonium or a metal complex,
L is a linker, and
X is a reactive group that chemically reacts with the contaminated fluid, or comprises hydroxy groups, wherein the hydroxy groups form hydrogen bonds with the contaminated fluid,
wherein the contaminated fluid is brought into contact with said adsorbent compound so as to effect a formation of an adduct, wherein the adduct comprises the adsorbent compound with an adsorbed fluorinated organic compound, and
the adsorbent compound with the adsorbed fluorinated organic compound is separated.

5. A method for separation of fluorinated organic compounds from contaminated fluids by means of a kit comprising at least a first adsorbent component and a second adsorbent component, the method comprising the following steps:
A) providing the first adsorbent component, wherein the first adsorbent component is a chemical compound comprising a lipophilic group and a hydrophilic group, or comprising such a compound in dissolved form,
wherein the hydrophilic group comprises at least one cationic group,
wherein the lipophilic group is selected from among alkyl groups comprising at least one octylene unit, aryl groups and aralkyl groups, and
wherein the at least one cationic group comprises an amine, an organic substituted ammonium, an organic substituted phosphonium or a metal complex; and providing the second adsorbent component, wherein the second adsorbent component is a solid adsorbent;
B) bringing the contaminated fluid into contact with the first adsorbent component;
C) bringing the contaminated fluid into contact with the second adsorbent component; and
D) separating the at least first adsorbent component and the second adsorbent component with adsorbed fluorinated organic compounds from the contaminated fluid.

6. The method of claim 5 , wherein steps B) and C) are carried out simultaneously, or step B) is carried out prior to step C).

7. The method of claim 5 , wherein the first adsorbent component has a formula R 1 -E-L-X, R 1 -L-E-X or R 1 -E-X, wherein R 1 is a lipophilic group, E is the hydrophilic group, L is a linker and X is a reactive group, which chemically reacts with the contaminated fluid in step B) and/or step C), or X includes hydroxy groups, wherein the hydroxy groups form hydrogen bonds with the contaminated fluid.

8. The method of claim 7 , wherein the reactive group X has at least one hydroxy group, or at least one hydroxy group is formed on the reactive group X by a reaction of the reactive group X with the contaminated fluid.

9. The method of claim 8 , wherein the reactive group X is selected from a group consisting of epoxide groups and groups that react to a hydroxy group in an S N reaction in step B) and/or step C).

10. The method of claim 9 , wherein the reactive group X is selected from the group consisting of 2-chloroethanol groups, alkyl sulfonate groups, bromoalkyl groups, and iodoalkyl groups.

11. The method of claim 7 , wherein two or more X or L-X groups are bonded to the hydrophilic group, and X is an ether group, or wherein at least one X or L-X group is bonded to the hydrophilic group, and X comprises a vicinal diol group or comprises a precursor for a vicinal diol group formed by reaction with the fluid in step B) and/or step C).

12. The method of claim 11 , wherein the group X is an ethyl or methyl ether group bonded via a methylene, ethylene, or propylene linker in the first adsorbent component having the formula R 1 -E-L-X, R 1 -L-E-X, or R 1 -E-X.

13. The method of claim 7 , wherein a pH value of the contaminated fluid is changed as a result of the reaction of the reactive group X with the contaminated fluid.

14. The method of claim 13 , Wherein the second adsorbent component provided in step A) has a non-ionic surface.

15. The method of claim 5 , wherein the second adsorbent component is selected from a group consisting of activated carbon, aluminum oxides, silica gels, soot, zeolite, fibrous celluloses, and microcrystalline celluloses.

16. The method of claim 5 , wherein a flocculent is added prior to step D).

17. The method of claim 5 , wherein step B) and/or step C) are carried out in a stirred tank reactor.

Assignees

• Fraunhofer Ges Forschung
• Cornelsen Solutions GmbH
• Fraunhofer Ges Forschung

Inventors

• Bruzzano Stefano
• Cornelsen Martin

Classifications

• B01J20/22

  comprising organic material · CPC title

• C02F1/285 Primary

  using synthetic organic sorbents · CPC title

• C02F1/683

  by addition of complex-forming compounds · CPC title

• C02F1/52

  by flocculation or precipitation of suspended impurities {(C02F1/463 takes precedence)} · CPC title

• C02F1/5272

  using specific organic precipitants · CPC title