# US 7,612,030 B2 · Enzymatic production of peracids using perhydrolytic enzymes

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- Number: US 7,612,030 B2
- Document ID: US7612030B2
- Status: Granted
- Kind: B2
- Application number: 11/413,246
- Filed: 2006-04-28
- Published: 2007-05-10
- Granted: 2009-11-03
- Earliest claimed: 2005-04-29
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Robert DiCosimo; Mark S. Payne; Vincent Brian Croud; John E. Gavagan; Lorraine W. Wagner; Eugenia Costa Hann
- Web page: https://patentgrep.com/patent/US7612030B2

## CPC

- A61L 2/186: Peroxide solutions
- A61L 2/183: Ozone dissolved in a liquid
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C11D 1/521: {Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups}
- C11D 3/2093: {Esters; Carbonates}
- C11D 3/32: Amides; Substituted amides
- C11D 3/386: Preparations containing enzymes {, e.g. protease or amylase}
- C11D 3/3947: {Liquid compositions}
- C11D 3/48: Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
- C12P 7/00: Preparation of oxygen-containing organic compounds
- C12P 7/40: containing a carboxyl group {including Peroxycarboxylic acids}
- A61L 2103/15: Laboratory, medical or dentistry appliances, e.g. catheters or sharps
- A61L 2103/50: Textiles, e.g. bedwear or towels
- A61L 2202/18: Aseptic storing means
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}

## Abstract

A process is provided to produce a concentrated aqueous peracid solution in situ using at least one enzyme having perhydrolase activity in the presence of hydrogen peroxide (at a concentration of at least 500 mM) under neutral to acidic reaction conditions from suitable carboxylic acid esters (including glycerides) and/or amides substrates. The concentrated peracid solution produced is sufficient for use in a variety of disinfection and/or bleaching applications.

## Claims

### Claim 1

A process for producing a concentrated aqueous peracid solution comprising;
a) providing a set of peracid reaction components, said components comprising:
1) at least one substrate selected from the group consisting of:
i) esters having the structure
wherein R1=C1 to C10 straight chain or branched chain alkyl optionally substituted with an hydroxyl or a C1 to C4 alkoxy group and R2=C1 to C10 straight chain or branched chain alkyl group, (CH2CH2—O)nH or (CH2CH(CH3)—O)nH and n=1 to 10;
ii) glycerides having the structure
wherein R1=C1 to C10 straight chain or branched chain alkyl optionally substituted with an hydroxyl or a C1 to C4 alkoxy group and R3 and R4 are individually H or R1C(O); and
iii) amides having the structure
wherein R5 and R6are individually H, acetyl, or a C1 to C5 straight chain or branched alkyl group;
2) a source of peroxygen that provides a concentration of at least 500 mM hydrogen peroxide upon combining said reaction components; and
3) at least one enzyme catalyst having perhydrolase activity, wherein said enzyme catalyst is selected from the group consisting of lipases, esterases, proteases, and mixtures thereof; and
b) combining said reaction components at a pH of about 2.5 to about 7.5, whereby a concentrated peracid solution is produced within at least about 5 minutes to about 2 hours after combining said reaction components.

### Claim 2 (depends on 1)

The process of claim 1 wherein the pH is 3 to 7.

### Claim 3 (depends on 2)

The process of claim 2 wherein the pH is 4 to 6.5.

### Claim 4 (depends on 1)

The process of claim 1 wherein the concentrated peracid solution has a peracid concentration of at least 10 ppm.

### Claim 5 (depends on 4)

The process of claim 4 wherein the peracid concentration is at least 100 ppm.

### Claim 6 (depends on 5)

The process of claim 5 wherein the peracid concentration is at least 500 ppm.

### Claim 7 (depends on 6)

The process of claim 6 wherein the peracid concentration is at least 1000 ppm.

### Claim 8 (depends on 7)

The process of claim 7 wherein the peracid concentration is at least 5000 ppm.

### Claim 9 (depends on 1)

The process of claim 1 wherein the reaction components comprise at least one lipase and at least one substrate selected from the group consisting of esters, glycerides, and mixtures thereof.

### Claim 10 (depends on 1, 9)

The process of claim 1 or claim 9 wherein said at least one substrate is an ester substrate selected from the group consisting of methyl lactate, ethyl lactate, methyl glycolate, ethyl glycolate, methyl methoxyacetate, ethyl methoxyacetate, methyl 3-hydroxybutyrate, ethyl 3-hydroxybutyrate, and mixtures thereof.

### Claim 11 (depends on 1, 9)

The process of claim 1 or claim 9 wherein the said at least one substrate is a glyceride substrate selected from the group consisting of monoacetin, diacetin, triacetin, monobutyrin, dibutyrin, tributyrin, glyceryl monooctanoate, glyceryl dioctanoate, glyceryl trioctanoate, and mixtures thereof.

### Claim 12 (depends on 11)

The process of claim 11 wherein said glyceride substrate is selected from the group consisting of monoacetin, diacetin, triacetin, and mixtures thereof.

### Claim 13 (depends on 1)

The process of claim 1 wherein said at least one enzyme catalyst is at least one lipase produced by an organism selected from the genera Aspergillus, Rhizopus, Penicillium, Candida, Pseudomonas, Mucor, Thermomyces, Alcaligenes, and Sus.

### Claim 14 (depends on 13)

The process of claim 13 wherein said at least one lipase is produced by an organism selected from the group consisting of Aspergillus sp., Aspergillus niger, Rhizopus sp., Rhizopus oryzae, Penicillium sp. I, Penicillium sp. II, Candida sp.,Candida rugosa, Candida antartia, Pseudomonas sp., Pseudomonas cepacia, Pseudomonas fluorescens, Thermomyces lanuginosus, Mucor sp., and Mucor miehei, and Alcaligenes sp.

### Claim 15 (depends on 14)

The process of claim 14 wherein said at least one lipase is selected from the group consisting of Aspergillus sp. lipase, Aspergillus niger lipase, Rhizopus sp. lipase, Rhizopus oryzae lipase, Penicillium sp.I lipase, Penicillium sp. II lipase, Candida sp.lipase, Candida rugosa lipase, Candida antartic lipase A, Candida antartica lipase B, Pseudomonas sp. lipase, Pseudomonas cepacia lipase, Pseudomonas fluorescens lipase, Thermomyces lanuginosus lipase, Mucor sp. lipase, Mucor miehei lipase, Alcaligenes sp. lipase, Sus sp. lipase, and mixtures thereof.

### Claim 16 (depends on 15)

The process of claim 15 wherein said at least one lipase is selected from the group consisting of BioCatalytics ICR-101 Aspergillus sp. lipase, BioCatalytics ICR-102 Rhizopus sp. lipase, BioCatalytics ICR-103 Rhizopus oryzae lipase, BioCatalytics ICR-104 Penicillium sp. I lipase, BioCatalytics ICR-105 Penicillium sp. II lipase, BioCatalytics ICR-106 Candida rugosa lipase, BioCatalytics ICR-107 Pseudomonas cepacia lipase, BioCatalytics ICR-108 Pseudomonas sp. lipase, BioCatalytics ICR-109 Pseudomonas fluorescens lipase, BioCatalytics ICR-110 Candida antartica lipase B, BioCatalytics ICR-111 Candida sp. lipase, BioCatalytics ICR-112 Candida antartica lipase A, BioCatalytics ICR-113 Pseudomonas sp. lipase, BioCatalytics ICR-114 porcine pancreas lipase, BioCatalytics ICR-115 Thermomyces languinosus lipase, BioCatalytics ICR-116 Mucor miehei lipase, BioCatalytics ICR-117 Alcaligenes sp. lipase, BioCatalytics IMB-111 immobilized Candida antartica lipase B, Amano Lipase AY 30 Candida rugosa lipase, Amano Lipase R Penicillium roqueforti lipase, Amano Lipase F-AP15 Rhizopus oryzae lipase, Amano Lipase M 10 Mucor javanicus lipase, Amano Lipase A 12 Aspergillus niger lipase, Amano Lipase G 50 Penicillium camembertii lipase, Amano F-DS Rhizopus oryzae lipase, Amano DS Aspergillus niger lipase, Novozym CALB L Candida antartica lipase B, Novozym 435 immobilized Candida antartica lipase B, and Novozym Palatase 20000L Aspergillus oryzae lipase, Lipozyme TL Thermomyces lanuginosus lipase, Chirazyme L2 Candida antartica lipase B, Validase AN Aspergillus niger lipase, Dietrenz CR Candida rugosa lipase, Enzeco MLC Aspergillus niger lipase, and mixtures thereof.

### Claim 17 (depends on 15)

The process of claim 15 wherein said lipase is selected from the group consisting of Candida antartica lipase B and Aspergillus niger lipase.

### Claim 18 (depends on 1)

The process of claim 1 wherein said at least one enzyme catalyst is at least one protease.

### Claim 19 (depends on 18)

The process of claim 18 wherein said at least one substrate is selected from the group of esters, glycerides, and mixtures thereof.

### Claim 20 (depends on 19)

The process of claim 19 wherein said substrate is an ester substrate selected from the group consisting of methyl lactate, ethyl lactate, methyl glycolate, ethyl glycolate, methyl methoxyacetate, ethyl methoxyacetate, methyl 3-hydroxybutyrate, ethyl 3-hydroxybutyrate, and mixtures thereof.

### Claim 21 (depends on 19)

The process of claim 19 wherein said substrate is a glyceride substrate selected from the group consisting of monoacetin, diacetin, triacetin, monobutyrin, dibutyrin, tributyrin, glyceryl monooctanoate, glyceryl dioctanoate, glyceryl trioctanoate, and mixtures thereof.

### Claim 22 (depends on 21)

The process of claim 21 wherein the glyceride substrate is selected from the group consisting of monoacetin, diacetin, triacetin, and mixtures thereof.

### Claim 23 (depends on 18)

The process of claim 18 wherein said at least one substrate is an amide selected from the group consisting of acetamide, diacetamide, and mixtures of acetamide and diacetamide.

### Claim 24 (depends on 18)

The process of claim 18 wherein said at least one protease is produced by an organism selected from the genera Aspergillus, Rhizopus, Bacillus, Carica, Ananas, Streptomyces, Tritirachium, and Sus.

### Claim 25 (depends on 24)

The process of claim 24 wherein said protease is produced from an organism selected from the group consisting of Aspergillus saitoi, Rhizopus sp., Bacillus sp., Bacillus subtilis, Sus scrofa, Carica papaya, Ananas comosus, Streptomyces griseus, and Tritirachium album.

### Claim 26 (depends on 25)

The process of claim 25 wherein said protease is selected from the group consisting of Aspergillus saitoi protease type XIII, Rhizopus sp. protease type XVIII, Bacillus sp. protease, Sus scrofa pepsin, Carica papaya Chymopapain, Carica papaya papain, Ananas comosus bromelain, Streptomyces griseus Pronase, Tritirachium album Proteinase K, and mixtures thereof.

### Claim 27 (depends on 26)

The process of claim 26 wherein said protease is selected from the group consisting of Streptomyces griseus Pronase, Tritirachium album Proteinase K, and mixtures thereof.

### Claim 28 (depends on 18)

The process of claim 18 wherein said at least one protease has prion-degrading activity and perhydrolase activity

### Claim 29 (depends on 1)

The process of claim 1 wherein the reaction components comprise at least one lipase and at least one prion-degrading protease.

### Claim 30 (depends on 29)

The process of claim 29 wherein the prion-degrading protease is selected from the group consisting of Proteinase K, Pronase, and mixtures thereof.

### Claim 31 (depends on 1)

The process of claim 1 wherein the peracid produced is selected from the group consisting of peracetic acid, perbutyric acid, perlactic acid, perglycolic acid, permethoxyacetic acid, per-β-hydroxybutyric acid, peroctanoic acid, and mixtures thereof.

### Claim 32 (depends on 31)

The process of claim 31 wherein the peracid is peracetic acid.