WO1991007375A1 - Peracetic acid composition - Google Patents
Peracetic acid composition Download PDFInfo
- 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
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.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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
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.
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.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8903773A SE8903773L (en) | 1989-11-10 | 1989-11-10 | PERAETTIKSYRAKOMPOSITION |
SE8903773-3 | 1989-11-10 |
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) |
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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 |
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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 |
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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 |
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Citations (6)
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 |
-
1989
- 1989-11-10 SE SE8903773A patent/SE8903773L/en not_active Application Discontinuation
-
1990
- 1990-11-06 WO PCT/SE1990/000716 patent/WO1991007375A1/en unknown
Patent Citations (6)
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)
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. * |
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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 |
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US6008405A (en) * | 1997-03-15 | 1999-12-28 | Solvay Interox Limited | Stabilized peracid solutions |
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SE8903773L (en) | 1991-05-11 |
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