# US 8,569,540 B2 · Stabilization of dicarbonate diesters with protonic acids

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- Number: US 8,569,540 B2
- Document ID: US8569540B2
- Status: Granted
- Kind: B2
- Application number: 12/297,493
- Filed: 2007-04-11
- Published: 2009-04-23
- Granted: 2013-10-29
- Earliest claimed: 2006-04-22
- Assignees: LANXESS Deutschland GmbH
- Applicants: Steffen Kahlert; Johannes Kaulen; Erasmus Vogl
- Inventors: Steffen Kahlert; Johannes Kaulen; Erasmus Vogl
- Web page: https://patentgrep.com/patent/US8569540B2

## CPC

- C07C 68/08: Purification; Separation; Stabilisation
- A23B 2/729: Organic compounds; Microorganisms; Enzymes
- A23B 2/758: Carboxylic acid esters
- A23B 2/788: Inorganic compounds
- A23B 70/10: by addition of preservatives
- C12H 1/14: with non-precipitating compounds, e.g. sulfiting; Sequestration, e.g. with chelate-producing compounds
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A23B: PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- 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

By using protonic acids, diesters of dicarbonic acid may be stabilized against thermal and chemical decomposition over a relatively long period. Mixtures of diesters of dicarbonic acid and protonic acids are outstandingly suitable for preserving foods.

## Claims

### Claim 1

A mixture for the stabilization of diesters of dicarbonic acid, comprising:
at least one protonic acid in an amount of 0.01 to 100,000 ppm, based on the diesters of dicarbonic acid, wherein the protonic acid is selected from the group of an inorganic acid and derivatives thereof and an organic carboxylic acid, and
one or more diesters of dicarbonic acid of the general formula (I)
where
R1 and R2 independently of one another are straight-chain or branched C1-C8-alkyl, cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl or benzyl,
each of which said R1 and R2 is optionally monosubstituted to polysubstituted, identically or differently by halogen; nitro; cyano; C1-C6-alkoxy; dialkylamino; or are phenyl which is optionally monosubstituted to polysubstituted, identically or differently by halogen; nitro; cyano; alkyl; haloalkyl; alkoxy; haloalkoxy; acyl; acyloxy; alkoxycarbonyl; carboxyl,
wherein said organic carboxylic acid is selected from the group consisting of saturated and monounsaturated or polyunsaturated aliphatic monocarboxylic acids, saturated or polyunsaturated aliphatic dicarboxylic and polycarboxylic acids and derivatives thereof, hydroxamic acids, hydroxycarboxylic acids, amino acids, and keto acids.

### Claim 2 (depends on 1)

The mixture according to claim 1, wherein the inorganic acid and derivatives thereof is selected from the group consisting of hydrochloric acid, sulphuric acid, sulphurous acid, nitric acid, nitrous acid, hypochlorous acid, chlorous acid, chloric acid, perchloric acid, sulphonic acids, and strongly acidic ion exchangers.

### Claim 3 (depends on 1)

The mixture according to claim 1 wherein diesters of dicarbonic acid are dimethyl dicarbonate or diethyl dicarbonate and wherein the at least one protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid, sulphurous acid, nitric acid, nitrous acid, hypochlorous acid, chlorous acid, chloric acid, perchloric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, longer-chain saturated and unsaturated fatty acids, oxalic acid, malonic acid, succinic acid, maleic acid, glutaric acid, citric acid, tartaric acid, malic acid, lactic acid, ascorbic acid and its derivatives thereof.

### Claim 4 (depends on 1)

The mixture according to claim 1, wherein the organic carboxylic acid and derivates thereof is selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, longer-chain saturated and unsaturated fatty acids, oxalic acid, malonic acid, succinic acid, maleic acid, glutaric acid, citric acid, tartaric acid, malic acid, lactic acid or ascorbic acid or derivatives thereof.

### Claim 5 (depends on 1)

A process for the preservation of foods, drinks and materials, comprising:
treating foods, drinks and materials with the mixture according to claim 1.

### Claim 6

A method for the purification by distillation of diesters of dicarbonic acids, comprising:
admixing one or more diesters of dicarbonic acids of the general formula
where
R1 and R2 independently of one another are straight-chain or branched C1-C8-alkyl, cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl or benzyl,
each of which is optionally monosubstituted to polysubstituted, identically or differently by halogen; nitro; cyano; C1-C6-alkoxy; dialkylamino; or are phenyl which is optionally monosubstituted to polysubstituted, identically or differently by halogen; nitro; cyano; alkyl; haloalkyl; alkoxy; haloalkoxy; acyl; acyloxy; alkoxycarbonyl; carboxyl,
with a protonic acid present in an amount of 0.01 to 100 000 ppm, based on the diesters of dicarbonic acid, thereby forming a mixture, and distilling the mixture,
wherein the protonic acid is selected from the group of an inorganic acid and derivatives thereof and an organic carboxylic acid, and
further wherein said organic carboxylic acid is selected from the group consisting of saturated and monounsaturated or polyunsaturated aliphatic monocarboxylic acids, saturated and monounsaturated or polyunsaturated aliphatic dicarboxylic and polycarboxylic acids and derivatives thereof, hydroxamic acids, hydroxycarboxylic acids, amino acids, and keto acids.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the distilling step is carried out at a pressure of 5 to 100 mbar and a temperature between 30 and 120° C.