Process for recovering a mixture comprising a (thio)phosphoric acid derivative

Patent metadata

Field	Value
Publication number	US-10954256-B2
Application number	US-201615763651-A
Country	US
Kind code	B2
Filing date	Sep 30, 2016
Priority date	Oct 1, 2015
Publication date	Mar 23, 2021
Grant date	Mar 23, 2021

Abstract

Provided herein is a use of a high-boiling solvent in a mixture comprising a (thio)phosphoric acid derivative and a process including the addition of a high-boiling solvent to a mixture comprising a (thio)phosphoric acid derivative to recover the (thio)phosphoric acid from the mixture by an evaporation process.

First claim

The invention claimed is:

1. A method of using at least one high-boiling solvent having a boiling point of at least 130° C., in a mixture comprising at least one (thio)phosphoric acid derivative and at least one volatile component, for preventing decomposition or solids formation of the at least one (thio)phosphoric acid derivative in an evaporation process, wherein said evaporation process comprises:
separating the at least one (thio)phosphoric acid derivative from the at least one volatile component, wherein the at least one volatile component is selected from the group consisting of liquid paraffinic, cycloparaffinic, and/or aromatic hydrocarbons, liquid halocarbons and halohydrocarbons, ethers, and esters; and
recovering as a bottom product a first mixture (1) comprising components:
(1a) the at least one (thio)phosphoric acid derivative; and
(1b) the at least one high-boiling solvent, wherein the at least one (thio)phosphoric acid derivative is selected from the group consisting of: (thio)phosphoric acid triamides according to general formula (I) and (thio)phosphoric acid ester amides according to general formula (IIa) or (IIb);
wherein general formula (I) is

wherein
X 1 is O or S;
R 1 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl;
R 2 is H, C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; or
R 1 and R 2 together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of N, O, and S; and
R 3 , R 4 , R 5 , and R 6 are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl;
and wherein general formula (IIa) is

wherein
X 2 is O or S;
R 7 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and
R 8 , R 9 , R 10 , and R 11 are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl;
and wherein general formula (IIb) is

wherein
X 3 is O or S;
R 12 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl;
R 15 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and
R 13 and R 14 are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl, and
wherein the at least one high-boiling solvent is hydrophilic.

2. The method according to claim 1 , wherein the at least one volatile component comprises at least one solvent having a boiling point of at least 30° C. lower than the boiling point of the at least one high-boiling solvent.

3. The method according to claim 1 , wherein the at least one high-boiling solvent is further used as a formulation agent for the at least one (thio)phosphoric acid derivative in the recovered first mixture (1).

4. A process for recovering at least one (thio)phosphoric acid derivative from a first mixture comprising the at least one (thio)phosphoric acid derivative and at least one solvent, wherein the process comprises:
adding at least one high-boiling solvent having a boiling point of at least 130° C. to the first mixture so as to form a second mixture (2) comprising components:
(2a) the at least one (thio)phosphoric acid derivative;
(2b) the at least one high-boiling solvent; and
(2c) the at least one solvent, the at least one solvent having a boiling point that is at least 30° C. lower than the boiling point of the at least one high-boiling solvent to be and is selected from liquid paraffinic, cycloparaffinic, and/or aromatic hydrocarbons, liquid halocarbons and halohydrocarbons, ethers, and esters; and
and separating a third mixture (1) from said second mixture (2), wherein said third mixture (1) comprises components:
(1a) the at least one (thio)phosphoric acid derivative; and
(1b) the at least one high-boiling solvent;
by evaporating the at least one solvent component (2c) of the second mixture (2) and collecting the third mixture (1) as a bottom product, wherein the at least one (thio)phosphoric acid derivative is selected from the group consisting of: (thio)phosphoric acid triamides according to general formula (I) and (thio)phosphoric acid ester amides according to general formula (IIa) or (IIb);
wherein general formula (I) is

wherein
X 1 is O or S;
R 1 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl;
R 2 is H, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; or
R 1 and R 2 together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of N, O, and S; and
R 3 , R 4 , R 5 , and R 6 are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl;
and wherein general formula (IIa) is

wherein
X 2 is O or S;
R 7 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and
R 8 , R 9 , R 10 , and R 11 are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl;
and wherein general formula (IIb) is

wherein
X 3 is O or S;
R 12 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl;
R 15 is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and
R 13 and R 14 are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl, and
wherein the at least one high-boiling solvent is hydrophilic.

5. The process according to claim 4 , wherein
evaporating the at least one solvent component (2c) of the second mixture (2) and collecting the third mixture (1) as the bottom product is performed by:
(i) continuously introducing a stream of the second mixture (2) into at least one thin film evaporator operating at a temperature of from 40° C. to 160° C. and at a pressure of from 5 mbar to 300 mbar (0.5 kPa to 30 kPa); and
(ii) continuously collecting the bottom product.

6. The process according to claim 4 , wherein the first mixture further comprises at least one HCl scavenger having a boiling point of at least 30° C. lower than the boiling point of the at least one high-boiling solvent.

Assignees

• Basf Se

Inventors

• Lang Tobias
• Schneider Karl-Heinrich
• Baan Zoltan
• Muelheims Philip
• Tschirschwitz Steffen
• Zhu Sascha Shuxia

Classifications

• C07F9/2458

  of aliphatic amines · CPC title

• C07F9/2475

  of aralkylamines · CPC title

• C07F9/242

  of hydroxyaryl compounds · CPC title

• C07F9/224 Primary

  Phosphorus triamides · CPC title

• C07F9/2466

  of cycloaliphatic amines · CPC title