WO1991007375A1 - Peracetic acid composition - Google Patents

Peracetic acid composition Download PDF

Info

Publication number
WO1991007375A1
WO1991007375A1 PCT/SE1990/000716 SE9000716W WO9107375A1 WO 1991007375 A1 WO1991007375 A1 WO 1991007375A1 SE 9000716 W SE9000716 W SE 9000716W WO 9107375 A1 WO9107375 A1 WO 9107375A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
weight
mineral
composition
hydrogen peroxide
Prior art date
Application number
PCT/SE1990/000716
Other languages
French (fr)
Inventor
Gunilla Jadesjö
Pia Hellström
Original Assignee
Eka Nobel Ab
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eka Nobel Ab filed Critical Eka Nobel Ab
Publication of WO1991007375A1 publication Critical patent/WO1991007375A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds

Definitions

  • the present invention relates to a composition containing peracetic acid, hydrogen peroxide, mineral acid and water. For the purpose of improving the stability of the peracetic acid, it also contains dipicolinic acid and at least one phosphonic acid. The invention also concerns a method of preparing peracetic acid from acetic acid and hydrogen peroxide.
  • Peracetic acid which is widely used as a dis- infectant, can be prepared directly from acetic acid and hydrogen peroxide with a mineral acid as a catalyst.
  • the raw materials often contain metal cations as impurities which catalyze the decomposition of the peracetic acid formed. Therefore, stabilizing agents are often added to the reaction mixture.
  • Prom SE, A, 7608459-9 it is known that phosphonic acids having capability of complex binding divalent metal cations, have an effect of stabilizing peracetic acid.
  • EP, Al, 87343 disclose peracetic acid compositions containing phosphonic acids and a high concentration of nitric acid, but the stability of the peracetic acid is not discussed.
  • dipicolinic acid for stabilizing peracetic acid is known from US, A, 2609391.
  • the stability of the peracetic acid in compositions containing dipicolinic acid is good, but the yield of peracetic acid prepared from acetic acid and hydrogen peroxide is rather low. It has also been found that no further improvement of the stabil ⁇ ity is obtained if the concentration of dipicolinic acid is higher than about 500 mg/1.
  • the composition contains peracetic acid, acetic acid, hydrogen peroxide and water. It also contains dipicolinic acid and at least one phosphonic acid having capability of complex binding divalent metal cations. Dipicolinic acid and phosphonic acids have thus appeared to show a synergistic effect in respect of stabilizing peracetic acid.
  • a compo ⁇ sition contain from 0.1 to 20, preferably from 1 to 5% by weight of phosphonic acids and from 0.1 to 5000, preferably from 10 to 1000 mg/1 of dipicolinic acid.
  • Any mineral acid for example sulfuric acid or pho ⁇ sphoric acid, can be used, alone or in a mixture.
  • concentration of mineral acid in the composition is suitab ⁇ ly at least 1% by weight, preferably at least 5% by weight.
  • All phosphonic acids having capability of complex binding divalent metal cations can be used, alone or in mixtures.
  • Specific examples of such phosphonic acids that can be used, alone or in mixtures, are aminotrimethylene phosphonic acid, ethylene diamin tetramethylene phosphonic acid, hexamethylene diamin tetramethylene phosphonic acid, diethylene triamin tetramethylene phosphonic acid and 1- hydroxyethylidene-l,l-diphosphonic acid.
  • a preferred composition according to the invention contains from 0.1 to 45, preferably from 0.5 to 15% by weight of peracetic acid, from 1 to 35, preferably from 15 to 30% by weight of hydrogen peroxide, from 1 to 40, preferably from 5 to 40% by weight of mineral acid, from 0.1 to 20, preferably from 1 to 5% by weight of phosphonic acids and from 0.1 to 5000, preferably from 10 to 1000 mg/1 of dipicolinic acid, the balance preferably substantially being acetic acid and water.
  • the invention also concerns a method of preparing peracetic acid by mixing acetic acid, hydrogen peroxide, a catalyzing mineral acid and water.
  • aqueous solutions of acetic acid, hydrogen peroxide and a mineral acid are mixed with water.
  • dipicolinic acid and one ore more phosphonic acids having capability of complex binding divalent metal cations are added to the reaction mixture.
  • the hydrogen peroxide reacts with the acetic acid, whereby peracetic acid forms.
  • concentration of peracetic acid is increasing while the concentrations of acetic acid and hydrogen peroxide are decreasing.
  • the concentrations of the other components remain substantially constant.
  • concentration of peracetic acid is decreasing due to decomposition.
  • the rate of decomposition is substantially decreased without decreasing the yield of peracetic acid.
  • the components are added so that the initial concentrations in the reaction mixture, i e before the peracetic acid starts forming, become from 0.1 to 45, preferably from 0.5 to 15% by weight of acetic acid, from 1 to 35, preferably from 15 to 30% by weight of hydrogen peroxide, from 1 to 40, preferably from 5 to 40% by weight of mineral acid, from 0.1 to 5000, preferably from 10 to 1000 mg/1 of dipicolinic acid and from 0.1 to 20, preferably from 1 to 5% by weight of phosphonic acids, the balance preferably substantially being water.
  • EXAMPLE 1 Four peracetic acid formulations were prepared according to the following specifications: A: 150 g 80% acetic acid was mixed with 328 g de- ionized water, whereupon 480 g 50% hydrogen peroxide was added carefully. Then 12 g 85% phosphoric acid, 30 g hydroxyethylidene diphosphonic acid and 500 g dipicolinic acid were added. B: The procedure according to A was repeated except that the dipicolinic acid was omitted.
  • EXAMPLE 3 The procedures according to example 1 were repeated except that the phosphoric acid was changed to 205 g 98% sulfuric acid and the amount of deionized water was changed to 135 g.

Abstract

The present invention relates to a composition containing peracetic acid, hydrogen peroxide, mineral acid and water. For the purpose of improving the stability of the peracetic acid, it also contains dipicolinic acid and at least one phosphonic acid having capability of complex binding divalent metal cations. The invention also concerns a method of preparing peracetic acid from acetic acid and hydrogen peroxide.

Description

PERACETIC ACID COMPOSITION The present invention relates to a composition containing peracetic acid, hydrogen peroxide, mineral acid and water. For the purpose of improving the stability of the peracetic acid, it also contains dipicolinic acid and at least one phosphonic acid. The invention also concerns a method of preparing peracetic acid from acetic acid and hydrogen peroxide.
Peracetic acid, which is widely used as a dis- infectant, can be prepared directly from acetic acid and hydrogen peroxide with a mineral acid as a catalyst. The raw materials often contain metal cations as impurities which catalyze the decomposition of the peracetic acid formed. Therefore, stabilizing agents are often added to the reaction mixture.
Prom SE, A, 7608459-9 it is known that phosphonic acids having capability of complex binding divalent metal cations, have an effect of stabilizing peracetic acid.
However, in many cases the stability obtained by the phosphonic acids is not satisfactory, especially not when the concentration of mineral acid is high. In some appli¬ cations it is desirable to use peracetic acid compositions with high content of mineral acid, see for example Oliver Daumen, "Peroxysauren in Verbindung mit Schwefelsaure- praparaten", Brauwelt, No 11 (1986), pp 385-390. Till now, this has been very difficult due to low stability of the peracetic acid.
EP, Al, 87343 disclose peracetic acid compositions containing phosphonic acids and a high concentration of nitric acid, but the stability of the peracetic acid is not discussed.
The use of dipicolinic acid for stabilizing peracetic acid is known from US, A, 2609391. The stability of the peracetic acid in compositions containing dipicolinic acid is good, but the yield of peracetic acid prepared from acetic acid and hydrogen peroxide is rather low. It has also been found that no further improvement of the stabil¬ ity is obtained if the concentration of dipicolinic acid is higher than about 500 mg/1.
DE, Al, 2451904 disclose the use of dipicolinic acid and sodium hexa-metaphosphate for stabilizing peracetic acid. However, there is no indication that any other compounds might be useful in combination with dipicolinic acid.
Now it has surprisingly been found that it is pos¬ sible to achieve a higher yield of peracetic acid and improved storage stability by providing a composition - according to claim 1. More specifically the composition contains peracetic acid, acetic acid, hydrogen peroxide and water. It also contains dipicolinic acid and at least one phosphonic acid having capability of complex binding divalent metal cations. Dipicolinic acid and phosphonic acids have thus appeared to show a synergistic effect in respect of stabilizing peracetic acid. Suitably a compo¬ sition contain from 0.1 to 20, preferably from 1 to 5% by weight of phosphonic acids and from 0.1 to 5000, preferably from 10 to 1000 mg/1 of dipicolinic acid. Any mineral acid, for example sulfuric acid or pho¬ sphoric acid, can be used, alone or in a mixture. The concentration of mineral acid in the composition is suitab¬ ly at least 1% by weight, preferably at least 5% by weight. All phosphonic acids having capability of complex binding divalent metal cations can be used, alone or in mixtures. Specific examples of such phosphonic acids that can be used, alone or in mixtures, are aminotrimethylene phosphonic acid, ethylene diamin tetramethylene phosphonic acid, hexamethylene diamin tetramethylene phosphonic acid, diethylene triamin tetramethylene phosphonic acid and 1- hydroxyethylidene-l,l-diphosphonic acid.
A preferred composition according to the invention contains from 0.1 to 45, preferably from 0.5 to 15% by weight of peracetic acid, from 1 to 35, preferably from 15 to 30% by weight of hydrogen peroxide, from 1 to 40, preferably from 5 to 40% by weight of mineral acid, from 0.1 to 20, preferably from 1 to 5% by weight of phosphonic acids and from 0.1 to 5000, preferably from 10 to 1000 mg/1 of dipicolinic acid, the balance preferably substantially being acetic acid and water.
The invention also concerns a method of preparing peracetic acid by mixing acetic acid, hydrogen peroxide, a catalyzing mineral acid and water. Preferably aqueous solutions of acetic acid, hydrogen peroxide and a mineral acid are mixed with water. Further, dipicolinic acid and one ore more phosphonic acids having capability of complex binding divalent metal cations are added to the reaction mixture. The hydrogen peroxide reacts with the acetic acid, whereby peracetic acid forms. During the time until the reaction comes to equilibrium, which takes about 4 days in room temperature, the concentration of peracetic acid is increasing while the concentrations of acetic acid and hydrogen peroxide are decreasing. The concentrations of the other components remain substantially constant. During further storage the concentration of peracetic acid is decreasing due to decomposition. However, by the addition of dipicolinic acid and phosphonic acids, the rate of decomposition is substantially decreased without decreasing the yield of peracetic acid.
Since the concentrations of mineral acid, dipicolinic acid and phosphonic acids do not change very much during storage of the mixture, neither before nor after egui- librium has been reached, these components are suitably added in quantities enough for obtaining the same con¬ centrations in the reaction mixture as they suitably have in a composition according to the invention. Any mineral acid or phosphonic acid suitable in the composition can also be used in the claimed method.
In a preferred method according to the invention, the components are added so that the initial concentrations in the reaction mixture, i e before the peracetic acid starts forming, become from 0.1 to 45, preferably from 0.5 to 15% by weight of acetic acid, from 1 to 35, preferably from 15 to 30% by weight of hydrogen peroxide, from 1 to 40, preferably from 5 to 40% by weight of mineral acid, from 0.1 to 5000, preferably from 10 to 1000 mg/1 of dipicolinic acid and from 0.1 to 20, preferably from 1 to 5% by weight of phosphonic acids, the balance preferably substantially being water.
The invention will now be described through the following examples which however do not restrict the invention. All percentages are based on weight if not otherwise stated.
EXAMPLE 1: Four peracetic acid formulations were prepared according to the following specifications: A: 150 g 80% acetic acid was mixed with 328 g de- ionized water, whereupon 480 g 50% hydrogen peroxide was added carefully. Then 12 g 85% phosphoric acid, 30 g hydroxyethylidene diphosphonic acid and 500 g dipicolinic acid were added. B: The procedure according to A was repeated except that the dipicolinic acid was omitted.
C: The procedure according to B was repeated except that 40 g of the phosphonic acid was added.
D: The procedure according to B was repeated except that the phosphonic acid was omitted.
The mixtures were stored at 20°C in a thermostat controlled water bath and were subjected to consecutive analyses in respect of peracetic acid. The results appear from table 2. EXAMPLE 2: The procedures according to example 1 were repeated except that the amounts of water and phosphoric acid were changed to 105 g deionized water and 235 g 80% phosphoric acid respectively.
EXAMPLE 3: The procedures according to example 1 were repeated except that the phosphoric acid was changed to 205 g 98% sulfuric acid and the amount of deionized water was changed to 135 g.
The initial concentrations of the main components before peracetic acid starts forming in the three examples appear from table 1. The results from the stability tests are shown in table 2. Table l; Initial concentrations of the main com onents
Figure imgf000007_0001
The results show that high acidity gives a higher yield of peracetic acid, but also a higher rate of decom¬ position. However, the examples show that the combination of stabilizing agents according to the invention, in all cases gives a higher content of peracetic acid than if they are used alone, after 4 days as well as after 36 days. Such an improvement cannot be achieved only by increasing the amount of phosphonic acid or dipicolinic acid.

Claims

1. Composition containing peracetic acid, acetic acid, hydrogen peroxide, mineral acid and water, c h a¬ r a c t e r i s e d in that it also contains dipicolinic acid and at least one phosphonic acid having capability of complex binding divalent metal cations.
2. Composition as claimed in claim 1, c h a r a c- t e r i s e d in that the concentration of the mineral acid in the composition is at least 1 % by weight.
3. Composition as claimed in claim 2, c h a r a c- t e r i s e in that the concentration of the mineral acid in the composition is at least 5 % by weight.
4. Composition as claimed in any of the claims 1-3, c h a r a c t e r i s e d in that the mineral acid includes phosphoric acid or sulfuric acid.
5. Composition as claimed in any of the preceding claims, c h a r a c t e r i s e d in that it contains from 0.1 to 45 % by weight of peracetic acid, from 1 to 35 % by weight of hydrogen peroxide, from 1 to 40 % by weight of mineral acid, from 0.1 to 20 % by weight of phosphonic acids and from 0.1 to 5000 mg/1 of dipicolinic acid.
6. A method of preparing peracetic acid by mixing acetic acid, hydrogen peroxide, mineral acid and water, c h a r a c t e r i s e d in that dipicolinic acid and at least one phosphonic acid having capability of complex binding divalent metal cations are added to the reaction mixture.
7. A method as claimed in claim t e r i s e d in that the mineral acid quantity enough for obtaining at least 1 mineral acid in the reaction mixture.
8. A method as claimed in claim t e r i s e d in that the mineral acid quantity enough for obtaining at least 5
Figure imgf000008_0001
mineral acid in the reaction mixture.
9. A method as claimed in any of the claims 6-8, c h a r a c t e r i s e d in that the mineral acid includes phosphoric acid or sulfuric acid.
10. A method as claimed in any of the claims 6-9, c h a r a c t e r i s e d in that the components are added so that the initial concentrations in the reaction mixture become from 0.1 to 45 % by weight of acetic acid, from 1 to 35 % by weight of hydrogen peroxide, from 1 to 40 % by weight of mineral acid, from 0.1 to 5000 mg/1 of di¬ picolinic acid and from 0.1 to 20 % by weight of phosphonic acid.
PCT/SE1990/000716 1989-11-10 1990-11-06 Peracetic acid composition WO1991007375A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE8903773-3 1989-11-10
SE8903773A SE8903773L (en) 1989-11-10 1989-11-10 PERAETTIKSYRAKOMPOSITION

Publications (1)

Publication Number Publication Date
WO1991007375A1 true WO1991007375A1 (en) 1991-05-30

Family

ID=20377438

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE1990/000716 WO1991007375A1 (en) 1989-11-10 1990-11-06 Peracetic acid composition

Country Status (2)

Country Link
SE (1) SE8903773L (en)
WO (1) WO1991007375A1 (en)

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993023517A1 (en) * 1992-05-16 1993-11-25 Laporte Esd Limited Peroxygen cleaning composition
EP0626371A1 (en) * 1993-05-26 1994-11-30 Degussa Aktiengesellschaft Stabilized percarboxylic acid solutions and process for their preparation
ES2072229A1 (en) * 1993-07-08 1995-07-01 Fmc Corp Method for controlling zebra mussels
WO1995033816A1 (en) * 1994-06-08 1995-12-14 Unilever Plc Aqueous bleaching compositions comprising peroxy carboxylic acids
US5632676A (en) * 1993-10-12 1997-05-27 Fmc Corporation Use of peracetic acid to sanitize processed fowl
US6008405A (en) * 1997-03-15 1999-12-28 Solvay Interox Limited Stabilized peracid solutions
EP1247801A1 (en) * 2001-04-04 2002-10-09 Kemira Chemicals Oy Process for the production of percarboxylic acid
EP1287740A1 (en) * 1998-04-06 2003-03-05 Ecolab Inc. Peroxy acid treatment to control pathogenic organisms on growing plants
CN102219722A (en) * 2011-07-27 2011-10-19 上海哈勃化学技术有限公司 Production technology of high purity peroxyacetic acid
BE1020013A3 (en) * 2011-07-11 2013-03-05 Christeyns Nv PRODUCTION OF MORE STABLE PERSONS.
CN102015648B (en) * 2008-04-29 2014-01-29 阿肯马法国公司 Perpropionic acid composition that is stable in a basic medium
WO2014055900A1 (en) 2012-10-05 2014-04-10 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US8822719B1 (en) 2013-03-05 2014-09-02 Ecolab Usa Inc. Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring
WO2014172280A1 (en) 2013-04-15 2014-10-23 Ecolab Usa Inc. Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing
EP2878593A1 (en) * 2006-10-18 2015-06-03 Ecolab Inc. Apparatus and method for making a peroxycarboxylic acid
US9242879B2 (en) 2012-03-30 2016-01-26 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water
US9253978B2 (en) 2008-03-28 2016-02-09 Ecolab USA, Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US9290448B2 (en) 2008-03-28 2016-03-22 Ecolab USA, Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US9288992B2 (en) 2013-03-05 2016-03-22 Ecolab USA, Inc. Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids
US9288982B2 (en) 2006-10-18 2016-03-22 Ecolab USA, Inc. Method for making a peroxycarboxylic acid
WO2016100694A1 (en) 2014-12-18 2016-06-23 Ecolab Usa Inc. Generation of peroxyformic acid through polyhydric alcohol formate
US9540598B2 (en) 2008-03-28 2017-01-10 Ecolab Usa Inc. Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids
US9560874B2 (en) 1998-08-20 2017-02-07 Ecolab Usa Inc. Treatment of animal carcasses
US10165774B2 (en) 2013-03-05 2019-01-01 Ecolab Usa Inc. Defoamer useful in a peracid composition with anionic surfactants
WO2019241635A1 (en) 2018-06-15 2019-12-19 Ecolab Usa Inc. On site generated performic acid compositions for teat treatment
WO2020028657A1 (en) 2018-08-02 2020-02-06 Evonik Corporation Stabilized peroxyacid solutions
WO2020041545A1 (en) 2018-08-22 2020-02-27 Ecolab Usa Inc. Hydrogen peroxide and peracid stabilization with molecules based on a pyridine carboxylic acid at c-3, -4 or -5
WO2021026410A1 (en) 2019-08-07 2021-02-11 Ecolab Usa Inc. Polymeric and solid-supported chelators for stabilization of peracid-containing compositions
WO2021155078A1 (en) 2020-01-31 2021-08-05 Ecolab Usa Inc. Generation of peroxyhydroxycarboxylic acid and the use thereof
WO2021163407A1 (en) 2020-02-12 2021-08-19 Ecolab Usa Inc. Use of urea or a urea / chelator combination to chemically stabilize peroxycarboxylic acid and peroxide formulations
US20210300839A1 (en) * 2020-03-31 2021-09-30 Ecolab Usa Inc. Method for quenching peroxycarboxylic acid runaway reactions
CN114190379A (en) * 2021-11-17 2022-03-18 陕西环玉食品科技有限公司 Universal high-stability monoperoxyacetic acid disinfectant and preparation method thereof
WO2022061104A1 (en) 2020-09-18 2022-03-24 Ecolab Usa Inc. Reduced misting peracid based cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight polymers
WO2022165094A1 (en) 2021-01-29 2022-08-04 Ecolab Usa Inc. Solid peroxyalphahydroxycarboxylic acid generation compositions and the use thereof
EP4136973A1 (en) 2012-10-05 2023-02-22 Ecolab USA Inc. Use of percarboxylic acid compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2609391A (en) * 1950-09-13 1952-09-02 Buffalo Electro Chem Co Stabilization of peracids with dipicolinic acid
US2877266A (en) * 1957-06-04 1959-03-10 Columbia Southern Chem Corp Preparation of peracids
US3048624A (en) * 1958-08-25 1962-08-07 Union Carbide Corp Stabilization of peracids
US3192254A (en) * 1959-10-19 1965-06-29 Shawinigan Chem Ltd Stabilization of peracids with picolinic acid
DE2451904A1 (en) * 1973-11-02 1975-05-07 Daicel Ltd PREPARATION FOR STABILIZING PERACETIC ACID
EP0087343A1 (en) * 1982-02-24 1983-08-31 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Commercial solutions of stable and non-corrosive percarboxylic acids and their use

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2609391A (en) * 1950-09-13 1952-09-02 Buffalo Electro Chem Co Stabilization of peracids with dipicolinic acid
US2877266A (en) * 1957-06-04 1959-03-10 Columbia Southern Chem Corp Preparation of peracids
US3048624A (en) * 1958-08-25 1962-08-07 Union Carbide Corp Stabilization of peracids
US3192254A (en) * 1959-10-19 1965-06-29 Shawinigan Chem Ltd Stabilization of peracids with picolinic acid
DE2451904A1 (en) * 1973-11-02 1975-05-07 Daicel Ltd PREPARATION FOR STABILIZING PERACETIC ACID
EP0087343A1 (en) * 1982-02-24 1983-08-31 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Commercial solutions of stable and non-corrosive percarboxylic acids and their use

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 104, No 19, 12 May 1986, (Columbus, Ohio, US), USA Food and Drug Administration: "Indirect food additives: adjuvants, production aids, and sanitizers; hydrogen peroxide, etc.", see page 547, Abstract 167038w; & FED. REGIST. 1904, 51(42), 7438-7439. *
CHEMICAL ABSTRACTS, Volume 88, No. 8, 20 February 1978, (Columbus, Ohio, US), Abstract 55113m; & DE,A,26 16 049, (Storage-stable concent rates of functional compositions), 27 October 1977, see page 282. *

Cited By (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993023517A1 (en) * 1992-05-16 1993-11-25 Laporte Esd Limited Peroxygen cleaning composition
EP0626371A1 (en) * 1993-05-26 1994-11-30 Degussa Aktiengesellschaft Stabilized percarboxylic acid solutions and process for their preparation
ES2072229A1 (en) * 1993-07-08 1995-07-01 Fmc Corp Method for controlling zebra mussels
US5632676A (en) * 1993-10-12 1997-05-27 Fmc Corporation Use of peracetic acid to sanitize processed fowl
WO1995033816A1 (en) * 1994-06-08 1995-12-14 Unilever Plc Aqueous bleaching compositions comprising peroxy carboxylic acids
US6008405A (en) * 1997-03-15 1999-12-28 Solvay Interox Limited Stabilized peracid solutions
EP1287740A1 (en) * 1998-04-06 2003-03-05 Ecolab Inc. Peroxy acid treatment to control pathogenic organisms on growing plants
US9770040B2 (en) 1998-08-20 2017-09-26 Ecolab Usa Inc. Treatment of animal carcasses
US9560875B2 (en) 1998-08-20 2017-02-07 Ecolab Usa Inc. Treatment of animal carcasses
US9560874B2 (en) 1998-08-20 2017-02-07 Ecolab Usa Inc. Treatment of animal carcasses
EP1247801A1 (en) * 2001-04-04 2002-10-09 Kemira Chemicals Oy Process for the production of percarboxylic acid
KR100902677B1 (en) * 2001-04-04 2009-06-15 케미라 오와이제이 Process for the production of percarboxylic acid
EP2878593A1 (en) * 2006-10-18 2015-06-03 Ecolab Inc. Apparatus and method for making a peroxycarboxylic acid
US9708256B2 (en) 2006-10-18 2017-07-18 Ecolab Usa Inc. Method for making a peroxycarboxylic acid
US9288982B2 (en) 2006-10-18 2016-03-22 Ecolab USA, Inc. Method for making a peroxycarboxylic acid
US9253978B2 (en) 2008-03-28 2016-02-09 Ecolab USA, Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US9540598B2 (en) 2008-03-28 2017-01-10 Ecolab Usa Inc. Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids
US11827867B2 (en) 2008-03-28 2023-11-28 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US9676711B2 (en) 2008-03-28 2017-06-13 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US10323218B2 (en) 2008-03-28 2019-06-18 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US10077415B2 (en) 2008-03-28 2018-09-18 Ecolab Usa Inc. Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids
US9290448B2 (en) 2008-03-28 2016-03-22 Ecolab USA, Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US10017720B2 (en) 2008-03-28 2018-07-10 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US11015151B2 (en) 2008-03-28 2021-05-25 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US10669512B2 (en) 2008-03-28 2020-06-02 Ecolab Usa Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
US9359295B2 (en) 2008-03-28 2016-06-07 Ecolab USA, Inc. Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents
CN102015648B (en) * 2008-04-29 2014-01-29 阿肯马法国公司 Perpropionic acid composition that is stable in a basic medium
BE1020013A3 (en) * 2011-07-11 2013-03-05 Christeyns Nv PRODUCTION OF MORE STABLE PERSONS.
CN102219722A (en) * 2011-07-27 2011-10-19 上海哈勃化学技术有限公司 Production technology of high purity peroxyacetic acid
US9902627B2 (en) 2011-12-20 2018-02-27 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US20160200595A1 (en) * 2011-12-20 2016-07-14 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US9321664B2 (en) * 2011-12-20 2016-04-26 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US20140097144A1 (en) * 2011-12-20 2014-04-10 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US9242879B2 (en) 2012-03-30 2016-01-26 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water
US9926214B2 (en) 2012-03-30 2018-03-27 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water
US10023484B2 (en) 2012-03-30 2018-07-17 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water
US10017403B2 (en) 2012-03-30 2018-07-10 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing enzymes for treatment of drilling fluids, frac fluids, flowback water and disposal water
US11180385B2 (en) 2012-10-05 2021-11-23 Ecolab USA, Inc. Stable percarboxylic acid compositions and uses thereof
AU2018241060B2 (en) * 2012-10-05 2020-05-28 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US11939241B2 (en) 2012-10-05 2024-03-26 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
WO2014055900A1 (en) 2012-10-05 2014-04-10 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
EP4136973A1 (en) 2012-10-05 2023-02-22 Ecolab USA Inc. Use of percarboxylic acid compositions
AU2020223668B2 (en) * 2012-10-05 2022-05-26 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
EP2903939A4 (en) * 2012-10-05 2016-02-17 Ecolab Usa Inc Stable percarboxylic acid compositions and uses thereof
US20220041473A1 (en) * 2012-10-05 2022-02-10 Ecolab USA, Inc. Stable percarboxylic acid compositions and uses thereof
AU2013326904B2 (en) * 2012-10-05 2018-07-05 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
EP2984929A1 (en) 2012-10-05 2016-02-17 Ecolab USA Inc. Stable percarboxylic acid compositions and uses thereof
EP3574758A1 (en) 2012-10-05 2019-12-04 Ecolab USA Inc. Stable percarboxlic acid compositions and uses thereof
US11206826B2 (en) 2013-03-05 2021-12-28 Ecolab Usa Inc. Defoamer useful in a peracid composition with anionic surfactants
US11026421B2 (en) 2013-03-05 2021-06-08 Ecolab Usa Inc. Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids
US10893674B2 (en) 2013-03-05 2021-01-19 Ecolab Usa Inc. Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids
US9585397B2 (en) 2013-03-05 2017-03-07 Ecolab Usa Inc. Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring
US10031081B2 (en) 2013-03-05 2018-07-24 Ecolab Usa Inc. Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring
US9288992B2 (en) 2013-03-05 2016-03-22 Ecolab USA, Inc. Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids
US10165774B2 (en) 2013-03-05 2019-01-01 Ecolab Usa Inc. Defoamer useful in a peracid composition with anionic surfactants
US9675076B2 (en) 2013-03-05 2017-06-13 Ecolab Usa Inc. Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring
US8822719B1 (en) 2013-03-05 2014-09-02 Ecolab Usa Inc. Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring
EP3461882A1 (en) 2013-04-15 2019-04-03 Ecolab USA Inc. Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing
WO2014172280A1 (en) 2013-04-15 2014-10-23 Ecolab Usa Inc. Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing
EP3766523A1 (en) 2014-12-18 2021-01-20 Ecolab USA Inc. Generation of peroxyformic acid through polyhydric alcohol formate
WO2016100694A1 (en) 2014-12-18 2016-06-23 Ecolab Usa Inc. Generation of peroxyformic acid through polyhydric alcohol formate
WO2019241635A1 (en) 2018-06-15 2019-12-19 Ecolab Usa Inc. On site generated performic acid compositions for teat treatment
US11779013B2 (en) 2018-08-02 2023-10-10 Evonik Corporation Stabilized peroxyacid solutions
WO2020028657A1 (en) 2018-08-02 2020-02-06 Evonik Corporation Stabilized peroxyacid solutions
WO2020041545A1 (en) 2018-08-22 2020-02-27 Ecolab Usa Inc. Hydrogen peroxide and peracid stabilization with molecules based on a pyridine carboxylic acid at c-3, -4 or -5
WO2021026410A1 (en) 2019-08-07 2021-02-11 Ecolab Usa Inc. Polymeric and solid-supported chelators for stabilization of peracid-containing compositions
EP4332090A2 (en) 2020-01-31 2024-03-06 Ecolab USA Inc. Generation of peroxyhydroxycarboxylic acid and the use thereof
WO2021155078A1 (en) 2020-01-31 2021-08-05 Ecolab Usa Inc. Generation of peroxyhydroxycarboxylic acid and the use thereof
WO2021163407A1 (en) 2020-02-12 2021-08-19 Ecolab Usa Inc. Use of urea or a urea / chelator combination to chemically stabilize peroxycarboxylic acid and peroxide formulations
US20210300839A1 (en) * 2020-03-31 2021-09-30 Ecolab Usa Inc. Method for quenching peroxycarboxylic acid runaway reactions
WO2022061104A1 (en) 2020-09-18 2022-03-24 Ecolab Usa Inc. Reduced misting peracid based cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight polymers
WO2022165094A1 (en) 2021-01-29 2022-08-04 Ecolab Usa Inc. Solid peroxyalphahydroxycarboxylic acid generation compositions and the use thereof
CN114190379A (en) * 2021-11-17 2022-03-18 陕西环玉食品科技有限公司 Universal high-stability monoperoxyacetic acid disinfectant and preparation method thereof

Also Published As

Publication number Publication date
SE8903773D0 (en) 1989-11-10
SE8903773L (en) 1991-05-11

Similar Documents

Publication Publication Date Title
WO1991007375A1 (en) Peracetic acid composition
US4070442A (en) Stabilized hydrogen peroxide
EP0426949B1 (en) Stabilisation of concentrated hydrogen peroxide solutions
GB1578062A (en) Process of stabilising sodium percarbonate
JP3181347B2 (en) Method for stabilizing amine oxide and amine oxide composition containing stabilizer
EP0364840A1 (en) Process for manufacturing a soda ash peroxygen
EP0363852B1 (en) Soda ash peroxygen carrier
EP0147207B2 (en) Disinfectants
US4362706A (en) Stabilizer system for commercial hydrogen peroxide
JP3597873B2 (en) Methods for controlling nitrosamine formation.
US4312843A (en) Dicalcium phosphate dihydrate having improved monofluorophosphate compatibility and process for the preparation thereof
EP0061268B1 (en) Stabilised peroxide composition and method of producing the same
US4322361A (en) Method of preparing a manganese chelate having improved properties
EP0368100B1 (en) Particulate composition containing bleach and an optical brightener and process for its manufacture
US3792152A (en) Stabilized phosphate and dentifrice compositions and process for producing same
US3629331A (en) Stabilization of urea peroxide
EP0047150B2 (en) Improvements relating to aminomethylenephosphonic acid solutions
JPH1135306A (en) Hydrogen peroxide composition
JP3919411B2 (en) Method for producing equilibrium peracetic acid composition having excellent stability
US4496527A (en) Dicalcium phosphate dihydrate having improved monofluorophosphate compatibility and process for the preparation thereof
EP0023104B1 (en) Plant growth medium
US4728460A (en) Aminomethylenephosphonic acid solutions
JP2644977B2 (en) Iminocarboxylate aqueous solution composition
US4594090A (en) High nutrient content fertilizers
EP0551298B1 (en) Peroxidic compositions

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE