Method for producing cocrystals by means of flash evaporation

Patent metadata

Field	Value
Publication number	US-10946305-B2
Application number	US-201515323654-A
Country	US
Kind code	B2
Filing date	Jul 6, 2015
Priority date	Jul 4, 2014
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

Abstract

The invention relates to a method for producing a cocrystal of at least two compounds by means of instantaneous evaporation or flash evaporation, for example for the production of cocrystals in the fields of energetic materials, pharmaceutical compounds, phytopharmaceutical compounds, ferroelectric materials, non-linear response materials or bioelectronic materials.

First claim

The invention claimed is:

1. A method for preparing a co-crystal of at least two compounds, comprising:
providing at least two organic, mineral, or organometal compounds which may be bound each other by hydrogen bonds, ionic bonds, bonds of the stacking type (π-π stacking) or Van der Waals bonds;
preparing a solution comprising at least one solvent and said at least two compounds to be co-crystalsized, wherein said preparation comprises dissolving said at least two compounds in said at least one solvent;
heating the solution, under a pressure ranging from 3 to 300 bars, at a temperature above the boiling point of the solvent or at a temperature above the boiling point of the mixture of solvents;
atomizing the solution in an atomization chamber with at least one dispersion device and under an angle ranging from 30 to 150° at a pressure ranging from 0.0001 to 2 bars;
separating the solvent or solvents in gaseous form; and
obtaining at least a co-crystal of said at least two compounds assembled on a molecular scale.

2. The method according to claim 1 wherein said at least two compounds are selected from the group consisting of:
two to ten compounds;
two compounds;
two compounds in a molar ratio selected from the group consisting of ¼, ⅓, ½, 1/1, 2/1, 3/1, and 4/1;
three compounds;
three compounds in a molar ratio X/Y/Z wherein X, Y and Z, either identical or different, represent 1, 2, 3 or 4;
four compounds;
four compounds in a molar ratio W/X/Y/Z wherein W, X, Y and Z, either identical or different, represent 1, 2, 3 or 4;
five compounds; and
five compounds in a molar ratio V/W/X/Y/Z wherein V, W, X, Y and Z, either identical or different, represent 1, 2, 3 or 4.

3. The method according to claim 1 wherein said co-crystal:
is of a micrometric size; or
has at least one dimension of less than 500 μm; or
has at least a dimension of less than 100 μm; or
is of submicrometric size; or
has at least one dimension comprised between 100 nm and 1,000 nm; or
is of a nanometric size; or
has at least one dimension of less than 100 nm; or
is of a size ranging from 2 to 100 nm; or
is of a size ranging from 5 to 90 nm; or
is of a size ranging from 10 to 80 nm; or
is of a size ranging from 50 to 300 nm; or
is of a size ranging from 50 to 200 nm; or
is of a size ranging from 50 to 120 nm; or
is of a size ranging from 10 to 100 nm; or
is of a size ranging from 60 to 100 nm.

4. The method according to claim 1 , comprising the preparation of one solution comprising said at least two compounds and at least two solvents or at least one solvent and at least one co-solvent or at least one solvent and at least one anti-solvent of one of the compounds.

5. The method according to claim 1 , further comprising recovering said co-crystals using one or more devices selected from the group consisting of an electrostatic separator, a cyclone, and a cyclone comprising an electrostatic device.

6. The method according to claim 1 wherein said method is continuous or semi-continuous.

7. The method according to claim 1 , wherein the solvent or of the mixture of solvents has a boiling point of less than 80° C. or less than 60° C.

8. The method according to claim 1 , wherein heating of the solution is carried out under a pressure ranging from 5 to 150 bars or ranging from 10 to 60 bars.

9. The method according to claim 1 , wherein heating of the solution is carried out under the pressure of an inert gas selected from the group consisting of nitrogen, argon, helium, neon, and xenon.

10. The method according to claim 1 , wherein atomization of the solution is carried out at a pressure ranging from 0.001 to 2 bars.

11. The method according to claim 1 , wherein the dispersion device is selected from the group consisting of a hollow cone nozzle, a solid cone nozzle, a flat jet nozzle, a rectilinear jet nozzle, a pneumatic atomizer, and combinations thereof.

12. The method according to claim 1 , wherein the dispersion device is a hollow cone nozzle.

13. The method according to claim 1 , wherein the compound is selected from the group consisting of energy compounds, pharmaceutical compounds, phytopharmaceutical compounds, coloring compounds, pigments, inks, paints, and metal oxides.

14. The method according to claim 1 , wherein the solvent is selected from the group consisting of alkanes; alcohols; thiols; aldehydes; ketones; ethers; acid esters; amines; and any mixture thereof.

15. A method for preparing a co-crystal of at least two compounds comprising successively:
providing at least two organic, mineral, or organometal compounds which may be bound each other by hydrogen bonds, ionic bonds, bonds of the stacking type (π-π stacking) or Van der Waals bonds;
preparing at least two solutions each comprising at least one solvent and said at least one compound, wherein each preparation comprises dissolving said compound in said solvent;
heating the solutions, under a pressure ranging from 3 to 300 bars, at a temperature above the boiling point of the solvent or at a temperature above the boiling point of the mixture of solvents;
atomizing the solutions in a same atomization chamber with at least one dispersion device and under an angle ranging from 30 to 150° at a pressure ranging from 0.0001 to 2 bars;
separating the solvents in a gaseous form; and
obtaining at least a co-crystal of said at least two compounds assembled on a molecular scale.

16. The method according to claim 15 wherein said at least two compounds are selected from the group consisting of:
two to ten compounds;
two compounds;
two compounds in a molar ratio selected from the group consisting of ¼, ⅓, ½, 1/1, 2/1, 3/1, and 4/1;
three compounds;
three compounds in a molar ratio X/Y/Z wherein X, Y and Z, either identical or different, represent 1, 2, 3 or 4;
four compounds;
four compounds in a molar ratio W/X/Y/Z wherein W, X, Y and Z, either identical or different, represent 1, 2, 3 or 4;
five compounds; and
five compounds in a molar ratio V/W/X/Y/Z wherein V, W, X, Y and Z, either identical or different, represent 1, 2, 3 or 4.

17. A method according to claim 15 wherein said co-crystal:
is of a micrometric size; or
has at least one dimension of less than 500 μm; or
has at least a dimension of less than 100 μm; or
is of submicrometric size; or
has at least one dimension comprised between 100 nm and 1,000 nm; or
is of a nanometric size; or
has at least one dimension of less than 100 nm; or
is of a size ranging from 2 to 100 nm; or
is of a size ranging from 5 to 90 nm; or
is of a size ranging from 10 to 80 nm; or
is of a size ranging from 50 to 300 nm; or
is of a size ranging from 50 to 200 nm; or
is of a size ranging from 50 to 120 nm; or
is of a size ranging from 10 to 100 nm; or
is of a size ranging from 60 to 100 nm.

18. The method according to claim 15 , further comprising recovering said co-crystals of compounds using one or several devices selected from the group consisting of an electrostatic separator, a cyclone, and a cyclone comprising an electrostatic device.

19. The method according to claim 15 wherein said method is continuous or semi-continuous.

20. The method according to claim 15 , wherein the solvent or of the mixture of solvents has a boiling point of less than 80° C. or less than 60° C.

21. The method according to claim 15 , wherein heating of the solutions is carried out under a pressure ranging from 5 to 150 bars or ranging from 10 to 60 bars.

22

Assignees

• Centre Nat Rech Scient
• Univ Strasbourg
• Isl—Institut Franco Allemand De Rech De Saint Louis
• Isl Institut Franco Allemand De Rech De Saint Louis

Inventors

• Risse Benedikt
• Spitzer Denis
• Pessina Florent

Classifications

• B01D1/16 Primary

  by spraying (B01D1/22 takes precedence) · CPC title

• B01D9/0018

  Evaporation of components of the mixture to be separated · CPC title

• B01D1/18

  to obtain dry solids (B01D1/24 takes precedence) · CPC title

• B01D9/0031

  by heating (B01D9/0022, B01D9/0027 take precedence) · CPC title

• C06B25/34

  the compound being a nitrated acyclic, alicyclic or heterocyclic amine · CPC title