Method for the production of a material of plant origin that is rich in phenolic acids, comprising at least one metal, for carrying out organic synthesis reactions

Patent metadata

Field	Value
Publication number	US-11254597-B2
Application number	US-201816498912-A
Country	US
Kind code	B2
Filing date	Mar 30, 2018
Priority date	Mar 31, 2017
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

Disclosed is a method for preparing a material of plant origin rich in phenolic acids, including at least one metal, including: preparing a material of plant origin chosen from: aquatic plants; materials rich in tannins; materials rich in lignin; and obtaining a material of plant origin, rich in phenolic acids, in which the ratio of the intensity of the vibration band of the C═O bond of the COOH group and the intensity of each of the vibration bands the aromatic ring determined in FT-IR is between 0.5 and 4. The material of plant origin is brought into contact with an effluent including from 0.1 to 1000 mg/l of at least one metal, thus obtaining a material of plant origin rich in phenolic acids including from 1 to 30% by weight of at least one metal relative to the total weight of the material.

First claim

The invention claimed is:

1. Method for preparing a material of plant origin rich in phenolic acids, comprising at least one metal, said method comprising the following steps:
a. preparation of a material of plant origin from a dead plant chosen from:
aquatic plants;
materials rich in tannins;
materials rich in lignin; and

obtaining a material of plant origin, rich in phenolic acids, in which the ratio of the intensity of the vibration band of the C═O bond of the COOH group and the intensity of each of the vibration bands the aromatic ring determined in FT-IR is between 0.5 and 4;
b. bringing into contact the material of plant origin obtained at the end of step a) with an effluent comprising from 0.1 to 1000 mg/l of at least one metal; and
c. obtaining a material of plant origin rich in phenolic acids comprising from 1 to 30% by weight of at least one metal relative to the total weight of the material.

2. Method for the decontamination or treatment of an effluent comprising at least one metal, said method comprising the following steps:
a. preparation of a material of plant origin from a dead plant chosen from:
aquatic plants;
materials rich in tannins;
materials rich in lignin; and

obtaining a material of plant origin, rich in phenolic acids, in which the ratio of the intensity of the vibration band of the C═O bond of the COOH group and the intensity of each of the bands of the aromatic ring vibration determined in FT-IR is between 0.5 and 4;
b. bringing into contact the material of plant origin obtained at the end of step a) with an effluent comprising from 0.1 to 1000 mg/l of at least one metal, and
c. obtaining an effluent comprising less than 100 mg/l by weight of said at least one metal.

3. Method according to claim 1 wherein the material of plant origin is chosen from:
the roots of aquatic plants;
coffee grounds or tea grounds;
wheat straw, pine cones, pine bark, coconut husks.

4. Method according to claim 1 , wherein the material of plant origin comprises phenolic acid functions and is capable of fixing more than 90% by weight, of at least one metal included in an effluent, said effluent comprising from 0.1 to 1000 mg/l of at least one metal.

5. Method according to claim 1 wherein the metal compound comprises at least one metal selected from platinoids, rare earths; or from the group consisting of Zn, Mn, Ni, Cu, Fe, Al, Ca, Mg, As, Sb, Cr, Cd, Ni and Co.

6. Method of claim 1 wherein:
when the material of plant origin is water hyacinth, the effluent comprises at least one metal selected from Sc, Ni, Ce, Yb, Co, Ni, Cu, Pd, Pt, Rh, Mn, Fe, Zn, As, Cr or Sb;
when the material of plant origin is water lettuce, the effluent comprises at least one metal chosen from Pd, Pt, Rh or Ni;
when the material of plant origin is coffee grounds, the effluent comprises at least one metal chosen from Pd, Pt, Rh, Mn, Fe, Zn, Ni or Cd.

7. Method according to claim 1 , wherein the material of plant origin has a ratio of the intensity of the absorption band of the C═O bond of the COOH group and of the absorption band of the aromatic ring determined in FT-IR less than 1.

8. Method according to claim 7 comprising a step of functionalizing the material of plant origin obtained at the end of step a), said step being prior to step b), and obtaining a source material in which the ratio of the intensity of the absorption band of the C═O bond of the COOH group and of the aromatic ring absorption band determined in FT-IR is greater than 1.

9. Method according to claim 8 wherein the functionalization step is performed via:
a carboxylation reaction of the material of plant origin obtained at the end of step a) with a carboxylic acid anhydride in an aprotic polar solvent; or
a autocatalysed esterification reaction between the material of plant origin obtained at the end of step a) and a polyacid, this reaction taking place in a solvent; or
an esterification reaction followed by hydrolysis and transfunctionalization.

10. Material of plant origin, rich in phenolic acids, comprising at least one metal, said material being obtained according to the method of claim 8 , further comprising functionalized phenolic acid functional groups.

11. Material of plant origin, rich in phenolic acids, comprising at least one metal, said material being obtained according to the method of claim 1 .

12. Material according to claim 10 , wherein the functionalization rate of the material of plant origin is between 0.0007 and 0.0014 mol NaOH /g of material in the case of water hyacinth and between 0.0006 and 0.0018 mol NaOH /g of material in the case of coffee grounds.

13. Method for implementing an organic synthesis reaction comprising the following steps:
a. heat treatment of a material according to claim 11 , and obtaining a calcined material;
b. implementation of an organic synthesis reaction involving the calcined material as a catalyst.

14. Method according claim 13 , wherein step a) comprises an acidic treatment of the calcined material.

15. Method according to claim 13 wherein the organic synthesis reaction is selected from:
the coupling reactions,
the reduction reactions,
the isomerization reaction of an exocyclic double bond;
the oxidation reactions;
oxidative halogenation reactions;
electrophilic substitution reactions;
condensation reactions;
multi-component reactions; and
oxidation reactions of alkenes.

16. The method of claim 1 , wherein the step of bringing into contact the material of plant origin obtained at the end of step a) with an effluent comprising from 0.1 to 1000 mg/l of at least one metal, is performed for a duration of between 1 hour and 2 hours, at a temperature between 10 and 30° C.

17. Method according to claim 1 , wherein the material of plant origin comprises phenolic acid functions and is capable of fixing more than 99% by weight, of at least one metal included in an effluent, said effluent comprising from 0.1 to 1000 mg/l of at least one metal.

18. Method of claim 1 wherein:
when the material of plant origin is water hyacinth, the effluent comprises at least one metal selected from Sc, Ni, Ce, Yb, Co, Ni, Cu, Pd, Pt, Mn, Fe, Zn or As;
when the material of plant origin is water lettuce, the effluent comprises at least one metal chosen from Pd, Pt or Ni;
when the material of plant origin is coffee grounds, the effluent comprises at least one metal chosen from Pd, Pt, Mn, Fe, Zn, Ni or Cd.

19. Material of plant origin, rich in phenolic acids, comprising at least one metal, wherein the material is dehydrated, and said plant origin being chosen from:
materials rich in tannins;
materials rich in lignin,

said material having a ratio of the intensity of the absorption band of the C═O bond of the COOH group and the aromatic ring absorption band determined in FT-IR is greater than 1 and possibly comprising phenolic acid functions functionalized.

20. Material of plant origin, rich in phenolic acids, comprising at least one metal, said material being obtained according to the method of claim 2 .

Assignees

• Centre Nat Rech Scient

Inventors

• Grison Claude
• Carrasco David
• Stanovych Andrii

Classifications

• B01J29/00

  Catalysts comprising molecular sieves {(molecular sieves per se C01B)} · CPC title

• B01J2235/10

  Infrared [IR] · CPC title

• B01J23/002

  Mixed oxides other than spinels, e.g. perovskite · CPC title

• C07C45/512

  the singly bound functional group being a free hydroxyl group · CPC title

• C07C1/00

  Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon · CPC title