# US 9,518,013 B2 · Generation of peroxyformic acid through polyhydric alcohol formate

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- Number: US 9,518,013 B2
- Document ID: US9518013B2
- Status: Granted
- Kind: B2
- Application number: 14/973,389
- Filed: 2015-12-17
- Published: 2016-06-23
- Granted: 2016-12-13
- Earliest claimed: 2014-12-18
- Assignees: Ecolab USA Inc.
- Applicants: Ecolab USA Inc.
- Inventors: Junzhong Li; Allison Brewster; Richard Staub; Steven J. Lange; Taz Cheritu; Jonathan P. Fast
- Web page: https://patentgrep.com/patent/US9518013B2

## CPC

- A01N 37/16: containing the group [IMAGE cpc-sch-A01N-0934.gif]; Thio analogues thereof
- A01N 37/00: Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids (containing cyclopropane carboxylic acids or derivatives thereof, e.g. cyclopropane carboxylic acid nitriles, A01N53/00)
- A61K 8/38: Percompounds, e.g. peracids
- A61L 2/00: Disinfection or sterilisation of materials or objects, in general; Accessories therefor
- A61L 2/16: using chemical substances
- A61P 1/02: Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 17/00: Drugs for dermatological disorders
- A61P 27/16: Otologicals
- A61P 31/04: Antibacterial agents
- A61Q 17/005: {Antimicrobial preparations}
- C07C 407/00: Preparation of peroxy compounds
- C07C 409/24: the —O—O— group being bound between a >C=O group and hydrogen, i.e. peroxy acids
- C11D 3/00: Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D 3/3947: {Liquid compositions}
- C11D 3/48: Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
- C12P 7/40: containing a carboxyl group {including Peroxycarboxylic acids}
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- 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
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

The present invention relates generally to peroxyformic acid forming compositions, methods for forming peroxyformic acid, preferably in situ, using the peroxyformic acid forming compositions. The present invention also relates to the peroxyformic acid formed by the above compositions and methods. The present invention further relates to the uses of the peroxyformic acid, preferably in situ, for treating a surface or a target. The present invention further relates to methods for treating a biofilm using peroxyformic acid, including peroxyformic acid generated in situ.

## Claims

### Claim 1

A method for forming peroxyformic acid comprising:
contacting a polyhydric alcohol ester of formic acid comprising glycerol formate with hydrogen peroxide to form a liquid that comprises peroxyformic acid,
wherein the formed liquid comprises at least 1 ppm peroxyformic acid within 1 minute,
wherein the pH of said formed liquid becomes 8 or lower within 1 minute after the contacting of the polyhydric alcohol ester of formic acid and hydrogen peroxide without the addition of an acidulant to decrease the pH of said formed liquid at any point after said contacting, and
wherein the method for forming peroxyformic acid does not include an enzyme catalyst and/or a second step of adding an acidulant to decrease the pH of said formed liquid.

### Claim 2 (depends on 1)

The method of claim 1, wherein the ester(s) further comprises pentaerythritol formates, mannitol formates, propylene glycol formates, sorbitol formates and sugar formates, and wherein the sugar formates are sucrose formates, dextrin formates, maltodextrin formates, or starch formates.

### Claim 3 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted with each other to form a solution that has a pH ranging from 6 to 8.

### Claim 4 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted with each other to form a solution that has a pH ranging from 4 to 8.

### Claim 5 (depends on 1)

The method of claim 1, wherein said polyhydric alcohol ester of formic acid and said hydrogen peroxide are kept separately prior to said contacting.

### Claim 6 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 1 ppm peroxyformic acid within 30 seconds or less.

### Claim 7 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 1 ppm peroxyformic acid within 15 seconds or less.

### Claim 8 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 100 ppm peroxyformic acid within 5 minutes or less.

### Claim 9 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 500 ppm peroxyformic acid within 5 minutes or less.

### Claim 10 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises peroxyformic acid under temperatures from 0° C. to 60° C.

### Claim 11 (depends on 1)

The method of claim 1, which further comprises using a stabilizing agent for peroxyformic acid, a stabilizing agent for hydrogen peroxide, and/or a pH buffering agent.

### Claim 12 (depends on 11)

The method of claim 11, wherein the stabilizing agent is phosphonate salt(s) and/or a heterocyclic dicarboxylic acid.

### Claim 13 (depends on 1)

The method of claim 1, wherein the formed liquid comprises from 1 ppm to 500,000 ppm of the polyhydric alcohol ester of formic acid and 0.1 ppm to 100,000 ppm of the hydrogen peroxide.

### Claim 14 (depends on 1)

The method of claim 1, wherein the formed liquid comprises a solution that comprises from 0.1 ppm to 10,000 ppm of peroxyformic acid.

### Claim 15 (depends on 1)

The method of claim 1, wherein the formed liquid comprises a solution that comprises from 100 ppm to 1,000 ppm of peroxyformic acid.

### Claim 16 (depends on 1)

The method of claim 1, wherein the polyhydric alcohol ester of formic acid and hydrogen peroxide are provided in a solid composition.

### Claim 17 (depends on 16)

The method of claim 16, wherein the solid composition comprises a stabilizing agent for peroxyformic acid, a stabilizing agent for hydrogen peroxide and/or a pH buffering agent.

### Claim 18

A method for forming peroxyformic acid comprising:
contacting a polyhydric alcohol ester of formic acid comprising glycerol formates and hydrogen peroxide to form a liquid that comprises from 0.1 ppm to 10,000 ppm of peroxyformic acid and wherein the pH of said formed liquid becomes 8 or lower without the addition of an acidulant to decrease the pH of said formed liquid at any point after said contacting;
wherein the ester in the formed liquid comprises from 1 ppm to 500,000 ppm
wherein the hydrogen peroxide in the formed liquid comprises from 0.1 ppm to 100,000 ppm,
wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 1 ppm peroxyformic acid within 1 minute of the contact time, and
wherein the method for forming peroxyformic acid does not include an enzyme catalyst and/or a second step of adding an acidulant to decrease the pH of said formed liquid.

### Claim 19 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are kept separately prior to said contacting.

### Claim 20 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted with each other to form a solution that has a pH ranging from 5 to 7.

### Claim 21 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 1 ppm peroxyformic acid within 30 seconds or less.

### Claim 22 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 1 ppm peroxyformic acid within 15 seconds or less.

### Claim 23 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least 100 ppm peroxyformic acid within 5 minutes or less.

### Claim 24 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises at least about 500 ppm peroxyformic acid within about 5 minutes or less.

### Claim 25 (depends on 18)

The method of claim 18, which further comprises using a stabilizing agent for peroxyformic acid, a stabilizing agent for hydrogen peroxide, and/or a pH buffering agent, and wherein the formed liquid comprises from 50 ppm to 40,000 ppm of the ester of the polyhydric alcohol and formic acid, and from 150 ppm to 50,000 ppm of the hydrogen peroxide.

### Claim 26 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and the hydrogen peroxide are contacted to form a solution that comprises from 1 ppm to 500 ppm of peroxyformic acid.

### Claim 27 (depends on 18)

The method of claim 18, wherein the polyhydric alcohol ester of formic acid and hydrogen peroxide are provided in a solid composition.
