Branched-chain fatty acids as liquid cation exchangers

Patent metadata

Field	Value
Publication number	US-9919303-B2
Application number	US-201314419580-A
Country	US
Kind code	B2
Filing date	Jul 24, 2013
Priority date	Aug 21, 2012
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The present invention relates to a method for removing an organic compound from an aqueous solution, comprising the steps of providing the aqueous solution which contains the organic compound, and a hydrophobic organic solution, where the latter comprises a liquid hydrophobic cation exchanger, contacting the aqueous solution and the hydrophobic organic solution, and separating off the hydrophobic organic solution from the aqueous solution, wherein the liquid hydrophobic cation exchanger is a saturated alkanoic acid having at least one alkyl substituent, where the organic compound is an organic compound having at least one positive charge and a neutral or positive total charge.

First claim

The invention claimed is:

1. A reaction mixture, comprising
an aqueous solution comprising an organic compound, and
a hydrophobic organic solution comprising a liquid hydrophobic cation exchanger,
wherein
the liquid hydrophobic cation exchanger is a saturated alkanoic acid comprising an alkyl substituent which has at least 12 carbon atoms, and
the organic compound is a compound of formula (II)
NR 2 R 3 H + -A-NR 4 R 5 H +   (II),

wherein
A is an alkylene group comprising at least three carbon atoms, and
R 2 , R 3 , R 4 , and R 5 , each independently, are selected from the group consisting of methyl, ethyl, propyl and butyl.

2. The reaction mixture according to claim 1 , wherein the liquid hydrophobic cation exchanger is a branched-chain fatty acid of formula (H 3 C) 2 CH—(CH 2 ) n —COOH, or an unprotonated form thereof, and n is at least 4.

3. The reaction mixture according to claim 1 , wherein the liquid cation exchanger is a branched-chain fatty acid which comprises substituents that are other than cyclic substituents.

4. The reaction mixture according to claim 1 , wherein the aqueous solution further comprises a metabolically active cell.

5. The reaction mixture according to claim 1 , wherein the organic compound is a diamine selected from the group consisting of 1,4-butanediamine, 1,5-pentanediamine, 1,6-hexanediamine, 1,8-octanediamine, 1,14-tetradecanediamine, 1,18-octadecanediamine, 2-methyl-1,5-diaminopentane, 2,2 dimethyl-1,5-diaminopentane, 4,4′-diaminodicyclohexylmethane, 3,3′-dimethyl-4,4′-diaminodicyclohexylmethane, 3,3′,5,5′-tetramethyl-4,4′-diaminodicyclohexylmethane, 2,2,4- or 2,4,4-trimethylhexamethylenediamine, 1,4-diaminocyclohexane, 4,4′-diaminodicyclohexylpropane, and isophoronediamine.

6. The reaction mixture according to claim 1 , wherein a molar ratio of the liquid cation exchanger to the organic compound is at least 1.

7. The reaction mixture according to claim 1 , wherein a molar ratio of the liquid cation exchanger to the organic compound is from 1.5 to 3.

8. The reaction mixture according to claim 1 , wherein a volumetric ratio of the hydrophobic organic solution to the aqueous solution is 100:1 to 1:100.

9. The reaction mixture according to claim 1 , wherein a volumetric ratio of the hydrophobic organic solution to the aqueous solution is 20:1 to 1:20.

10. The reaction mixture according to claim 1 , wherein a volumetric ratio of the hydrophobic organic solution to the aqueous solution is 2:1 to 1:2.

Assignees

• Erhardt Frank
• Falke Lukas
• Kelle Ralf
• Haeger Harald
• Haas Thomas
• Hennemann Hans Georg
• Thum Oliver
• Roos Martin
• Poetter Markus
• Evonik Degussa Gmbh

Inventors

• Erhardt Frank
• Falke Lukas
• Kelle Ralf
• Haeger Harald
• Haas Thomas
• Hennemann Hans-Georg
• Thum Oliver
• Roos Martin
• Poetter Markus

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C209/90

  Stabilisation; Use of additives · CPC title

• C02F2001/425

  using cation exchangers · CPC title

• C07C209/84

  Purification · CPC title

• C02F1/42

  by ion-exchange (ion-exchange in general B01J) · CPC title