# US 2010/0166930 A1 · Process for extracting carbonylated compounds from a drink by liquid-solid extraction with a functionalized inert support

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- Number: US 2010/0166930 A1
- Document ID: US20100166930A1
- Status: Published application
- Kind: A1
- Application number: 12/293,802
- Filed: 2007-03-22
- Published: 2010-07-01
- Earliest claimed: 2006-03-22
- Assignees: Centre National de la Recherche Scientifique (CNRS)
- Inventors: Hervé Deleuze; Mélanie Blasi; Jean-Christophe Barbe; Denis Dubourdieu; Bernard Jean Maillard
- Web page: https://patentgrep.com/patent/US20100166930A1

## CPC

- C12G 1/04: Sulfiting the must; Desulfiting
- B01D 15/00: Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01J 20/103: {comprising silica}
- B01J 20/261: {obtained by reactions only involving carbon to carbon unsaturated bonds (macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds per se C08F)}
- B01J 20/264: {derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers}
- B01J 20/267: {Cross-linked polymers}
- B01J 20/28004: {Sorbent size or size distribution, e.g. particle size}
- B01J 20/28083: {being in the range 2-50 nm, i.e. mesopores}
- B01J 20/28085: {being more than 50 nm, i.e. macropores}
- B01J 20/3204: {Inorganic carriers, supports or substrates}
- B01J 20/321: {consisting of a polymer obtained by reactions involving only carbon to carbon unsaturated bonds}
- B01J 20/3242: {Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group}
- B01J 20/3251: {comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulphur}
- B01J 20/3253: {comprising a cyclic structure not containing any of the heteroatoms nitrogen, oxygen or sulfur, e.g. aromatic structures}
- B01J 20/3259: {comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom}
- B01J 20/3261: {comprising a cyclic structure not containing any of the heteroatoms nitrogen, oxygen or sulfur, e.g. aromatic structures}
- C12H 1/0424: {with the aid of a polymer}
- C12G: WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES (beer C12C); PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C12H: PASTEURISATION, STERILISATION, PRESERVATION, PURIFICATION, CLARIFICATION OR AGEING OF ALCOHOLIC BEVERAGES; METHODS FOR ALTERING THE ALCOHOL CONTENT OF FERMENTED SOLUTIONS OR ALCOHOLIC BEVERAGES (simulation ageing by flavouring C12G3/06)

## Abstract

The present invention relates to a process for extracting carbonylated compounds from a drink by liquid-solid extraction with a functionalized inert support containing nitrogenous nucleophilic functional groups. Advantageously, according to the present invention, the drink is wine or fruit juice. The process according to the present invention is advantageously applied to the reduction of the sulphur dioxide combination capacity of a drink such as wine.

## Claims

### Claim 1

Process for extracting carbonyl compounds from a beverage by liquid-solid extraction using an inert functionalized support containing functional nitrogenous nucleophilic groups.

### Claim 2 (depends on 1)

Extraction process according to claim 1, characterized in that the beverage is wine or fruit juice.

### Claim 3 (depends on 2)

Extraction process according to claim 2, characterized in that the carbonyl compounds are compounds present in wine or fruit juice, in particular ethanal, pyruvic acid, 2-oxoglutaric acid, 5-oxofructose, and their mixtures.

### Claim 4

Extraction process according to any of claims to 3, characterized in that the functional nitrogenous, nucleophilic groups are chosen from the group consisting of hydroxylamines of RONH2 type in which R is an alkyl or aryl group; derivatives of hydrazines, advantageously hydrazines of formula RNHNH2 in which R is an alkyl or aryl group, sulfonylhydrazines of formula RSO2NHNH2 in which R is an alkyl or ayrl group, semicarbazides and 2,4-dinitrophenylhydrazine; and diamines in which the nitrogen atoms are separated by an ethylene group and are substituted by identical or different groups.

### Claim 5

Extraction process according to any of claims to 4, characterized in that the functional nitrogenous, nucleophilic groups are chosen from among phenylsulfonylhydrazine and O-benzylhydroxylamine.

### Claim 6

Extraction process according to any of the preceding claims, characterized in that the support is a support insoluble in the beverage, is organic or inorganic, and is advantageously of millimeter size.

### Claim 7 (depends on 6)

Extraction process according to claim 6, characterized in that the support is polymer-, silica-, alumina- or clay-based.

### Claim 8 (depends on 7)

Extraction process according to claim 7, characterized in that the support is a polymeric support containing vinyl and/or styrene monomers, advantageously a support containing a styrene-divinylbenzene copolymer.

### Claim 9

Extraction process according to any of the preceding claims, characterized in that the functionalization rate of the support lies between 0.75 and 4.5 mmol/g.

### Claim 10

Extraction process according to any of the preceding claims, characterized in that the quantity of support ranges from 1 to 15 g per liter of beverage.

### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10)

Process to reduce the sulfur dioxide binding power of a beverage, comprising the following successive steps:
extraction of carbonyl compounds from said beverage following the process such as defined in any of claims 1 to 10, and
removal of the support by filtration or decanting.

### Claim 12 (depends on 11)

Process according to claim 11, characterized in that extraction of carbonyl compounds is performed at ambient temperature, advantageously without agitation.

### Claim 13 (depends on 11, 12)

Process according to claim 11 or 12, characterized in that extraction is conducted for a time of between 1 day and 52 weeks.

### Claim 14 (depends on 11, 12, 13)

Process according to any of claims 11 to 13, characterized in that the process is implemented before or after sulfiting.