CN102911062A - Method for preparing 1,3-cyclohexyl dimethylamine - Google Patents
Method for preparing 1,3-cyclohexyl dimethylamine Download PDFInfo
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Abstract
The invention relates to a method for preparing 1,3-cyclohexyl dimethylamine. Two steps of hydrogenation are carried out under the same solvent, the first step of hydrogenation uses raney nickel as a catalyst, one or more of methanol, methylamine or 1,4-dioxane is or are used as the solvent, and organic amine, liquid ammonia, water or sodium hydroxide are used as an addition agent. Under the condition of 40-80 DEG C of reaction temperature and 5-8 MPa of reaction pressure, isophthalonitrile and hydrogen are reacted, the reaction time is 1-5 hours, and an isophthalonitrile reaction solution is obtained. The second step of hydrogenation uses ruthenium-supported activated carbon as the catalyst. Under the condition of 80-130 DEG C of reaction temperature and 5-8 MPa of reaction pressure, the isophthalonitrile reaction solution and hydrogen are reacted, the reaction time is 1-6 hours, and 1,3-cyclohexyl dimethylamine is obtained. The total yield of the method can reach 90 percent. The method has the advantages of simplicity in process operation, high yield and easiness in rectification, can be directly improved on the current MXDA production process, and is easy for industrialization.
Description
Technical field
The present invention relates to a kind of preparation method of pesticide intermediate, especially relate to a kind of method for preparing 1,3-cyclohexyl dimethylamine.
Background technology
1,3-BAC, Chinese 1,3-cyclohexyl dimethylamine by name or 1,3-diamines methylcyclohexane, English 1,3-Bis (aminomethyl) Cyclohexane by name or 1,3-Cyclohexanedimethanamine (CA name),
Molecular formula is C
8H
18N
2, 1,3-BAC is colourless, little transparent liquid that the ammonia flavor is arranged, 220 ℃ of boiling points, zero pour be below-70 ℃, 113 ℃ of flash-points (Cleveland opens cup type), proportion (20 ℃) 0.942, viscosity 9.06 (cp, 20 ℃), vapour pressure 14mmHg (120 ℃).Water soluble, alcohol, ether, normal hexane, hexanaphthene, benzene equal solvent.Main solidifying agent as Resins, epoxy, urethane intermediate and corrosion prevention rust preventer.
Nowadays mainly contain Mitsubishi's gas abroad, the manufacturer production such as BASF 1,3-BAC, and domestic manufacturer is very few, the self-produced MXDA of my company has good economic advantages for producing 1,3-BAC.Particularly after MXDA was put into noxious chemical, 1, the 3-BAC as an alternative demand of product can sharply rise.According to using the raw material classification, the preparation method of 1,3-BAC is divided into two kinds, is respectively IPN method and MXDA method.Below will introduce respectively from the document aspect this two kinds of methods.
Standby 1, the 3-BAC of IPN legal system.Mitsubishi's gas was applied for a patent US5371293 in 1994, this patent uses 5% supported ruthenium charcoal or ruthenium aluminum oxide to be catalyzer, under the reaction system of dioxane and liquefied ammonia existence, under the temperature of reaction of the reaction pressure of 100atm and about 100 ℃, carry out hydrogenation reaction, the molar yield of 1,3-BAC is about 88%.Patent US4070399 is take 5% loading type Ru-Pd/C as catalyzer, with lower aliphatic alcohols, dioxane, low-grade aliphatic amines etc. are solvent, there is ammonia to exist in the reaction system, under the pressure of about 100atm and under 100-150 ℃ the temperature TPN is being carried out hydrogenation reaction, the mass yield of Isosorbide-5-Nitrae-BAC is up to 98%.Patent US3998881 is take 5% loading type rhodium aluminum oxide as catalyzer, and solvent uses dioxane, tetrahydrofuran (THF), and chloroform etc., reaction pressure is 100atm approximately, and temperature of reaction is 100-150 ℃, and the total recovery after the rectifying is 71%.Standby 1, the 3-BAC of above-mentioned IP N legal system has the relatively poor shortcoming of selectivity.
Standby 1, the 3-BAC of MXDA legal system.Patent EP0703213 working load type ruthenium, nickel, rhodium (perhaps their compound) catalyzer, the solvent that reaction is used is methylamine, dimethylamine, quadrol, BAC, methyl alcohol etc., the volume ratio of MXDA and solvent is 1: 3-1: 20, reaction pressure is 50-150atm, and temperature of reaction is 80-130 ℃, and mass yield can reach 94%.Patent US4181680 working load type ruthenium catalyst, the per-cent that the quality of metal Ru accounts for catalyzer total mass (comprising catalyzer and carrier) is 0.1-10%, the solvent that reaction is used is distilled water, the volume ratio of MXDA and solvent is 1: 1-1: 10, reaction pressure is 100-150atm, temperature of reaction is 75-130 ℃, and molar yield can reach about 88%.Owing to MXDA is got by the IPN hydrogenation, therefore prepare 1,3-BAC high cost take MXDA as raw material.
Summary of the invention
Purpose of the present invention is exactly to provide a kind of technological operation simple for the defective that overcomes above-mentioned prior art existence, and yield is high, the easily preparation 1 of rectifying, the method for 3-cyclohexyl dimethylamine.
Purpose of the present invention can be achieved through the following technical solutions:
A kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, it is characterized in that, the method is carried out two-stage hydrogenation under same solvent, the first paragraph hydrogenation is take Raney's nickel as catalyzer, methyl alcohol, methylamine or 1, in the 4-dioxane one or more are solvent, organic amine, liquefied ammonia, water or sodium hydroxide are auxiliary agent, are 40-80 ℃ in temperature of reaction, and reaction pressure is under the 5-8MPa, Isophthalodinitrile and hydrogen react, reaction times is 1-5h, obtains the m-xylene diamine reaction solution, and the second segment hydrogenation is take the gac that supports ruthenium as catalyzer, it is 80-130 ℃ in temperature of reaction, reaction pressure is under the 5-8MPa, and m-xylene diamine reaction solution and hydrogen are proceeded reaction, and the reaction times is 1-6h, prepare 1,3-cyclohexyl dimethylamine.
Preferred Isosorbide-5-Nitrae-the dioxane of described solvent; Described auxiliary agent preferred concentration is the sodium hydroxide of 50wt%.
Described solvent accounts for the 50-90wt% of first paragraph hydrogenation reaction thing total amount, and auxiliary agent accounts for the 0.6-6wt% of first paragraph hydrogenation reaction thing total amount, and Raney's nickel accounts for the 2.5-6wt% of first paragraph hydrogenation reaction thing total amount.
Described solvent accounts for the 60-80wt% of first paragraph hydrogenation reaction thing total amount, and auxiliary agent accounts for the 1-4wt% of first paragraph hydrogenation reaction thing total amount, and Raney's nickel accounts for the 3-6wt% of first paragraph hydrogenation reaction thing total amount.
The preferred 50-70 of the temperature of reaction of described first paragraph hydrogenation ℃, the preferred 5-7MPa of reaction pressure, preferred 1-3h of reaction times.
Contain ruthenium 5wt% in the catalyzer of the described gac that supports ruthenium, the add-on of catalyzer accounts for the 1-5wt% of second segment hydrogenation reaction thing total amount.
The add-on of described catalyzer accounts for the 2-4wt% of second segment hydrogenation reaction thing total amount.
The preferred 90-110 of the temperature of reaction of described second segment hydrogenation ℃, the preferred 5-7MPa of reaction pressure, preferred 1-4h of reaction times.
Compared with prior art, the present invention has that technological operation is simple, and yield is high, the easy characteristics of rectifying, and the total recovery after the rectifying can reach 90%, can directly improve in existing MXDA production technique, is easy to industrialization.
Embodiment
The present invention is described in detail below in conjunction with specific embodiment.
Embodiment 1
In autoclave, drop into successively the 60g m-xylene diamine, the 120g dioxane, 5.62g50% sodium hydroxide solution and 8g Raney's nickel catalyst close still, use H
2After replacing three times, pass into H
2To 5MPa, open and be heated with stirring to 60 ℃, be inflated to again 6MPa, wait reaction to inhale hydrogen, Pressure Drop is inflated to 6MPa during to 5MPa, and so repeatable operation is to no longer inhaling till the hydrogen, and reacted approximately 80 minutes this moment.Be cooled to room temperature, emptying hydrogen is driven still, pours out supernatant liquid (MXDA reaction solution), and lower floor's catalyzer is applied mechanically.
In autoclave, drop into successively the ruthenium Pd/carbon catalyst of a certain amount of above-mentioned MXDA reaction solution and 4g5%, close still, use H
2After replacing three times, pass into H
2To 6MPa, open and be heated with stirring to 90 ℃, be inflated to again 7MPa, hydrogen is inhaled in reaction, and Pressure Drop is inflated to 7MPa during to 6MPa, and so repeatable operation is to no longer inhaling till the hydrogen, and reacted approximately 140 minutes this moment.Be cooled to room temperature, still is driven in emptying, discharging, and suction filtration, filter cake (catalyzer) is applied mechanically, and the total recovery of filtrate after precipitation rectifying is 88.3%.
Embodiment 2
In autoclave, drop into successively the 37.5g m-xylene diamine, the 150g dioxane, 5.7g50% sodium hydroxide solution and 8g Raney's nickel catalyst close still, use H
2After replacing three times, pass into H
2To 5MPa, open and be heated with stirring to 70 ℃, be inflated to again 6MPa, hydrogen is inhaled in reaction, and Pressure Drop is inflated to 6MPa during to 5MPa, and so repeatable operation is to no longer inhaling till the hydrogen, and reacted approximately 60 minutes this moment.Be cooled to room temperature, still is driven in emptying, pours out supernatant liquid (MXDA reaction solution), and lower floor's catalyzer is applied mechanically.
In autoclave, drop into successively the ruthenium Pd/carbon catalyst of a certain amount of above-mentioned MXDA reaction solution and 4g5%, close still, use H
2After replacing three times, pass into H
2To 6MPa, open and be heated with stirring to 100 ℃, be inflated to again 7MPa, inhale hydrogen Deng reaction, Pressure Drop is inflated to 7MPa during to 6MPa, and so repeatable operation is to no longer inhaling till the hydrogen, reacted approximately 120 minutes this moment. be cooled to room temperature, still is driven in emptying, discharging, suction filtration, filter cake (catalyzer) is applied mechanically, and the total recovery of filtrate after precipitation rectifying is 90%.
Embodiment 3
In autoclave, drop into successively the 37.5g m-xylene diamine, the 150g dioxane, 5.7g50% sodium hydroxide solution and 8g Raney's nickel catalyst close still, use H
2After replacing three times, pass into H
2To 5MPa, open and be heated with stirring to 70 ℃, be inflated to again 6MPa, wait reaction to inhale hydrogen, Pressure Drop is inflated to 6MPa during to 5MPa, and so repeatable operation is to no longer inhaling till the hydrogen, and reacted approximately 100 minutes this moment.Be cooled to room temperature, still is driven in emptying, pours out supernatant liquid (MXDA reaction solution), and lower floor's catalyzer is applied mechanically.
In autoclave, drop into successively the ruthenium Pd/carbon catalyst of a certain amount of above-mentioned MXDA reaction solution and 5g5%, close still, use H
2After replacing three times, pass into H
2To 6MPa, open and be heated with stirring to 100 ℃, be inflated to again 7MPa, inhale hydrogen Deng reaction, Pressure Drop is inflated to 7MPa during to 6MPa, and so repeatable operation is to no longer inhaling till the hydrogen, reacted approximately 100 minutes this moment. be cooled to room temperature, still is driven in emptying, discharging, suction filtration, filter cake (catalyzer) is applied mechanically, and the total recovery of filtrate after precipitation rectifying is 90%.
Embodiment 4
A kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, the method is carried out two-stage hydrogenation under same solvent, the first paragraph hydrogenation is take Raney's nickel as catalyzer, take methyl alcohol as solvent, liquefied ammonia is auxiliary agent, and wherein, solvent accounts for the 50wt% of first paragraph hydrogenation reaction thing total amount, auxiliary agent accounts for the 0.6wt% of first paragraph hydrogenation reaction thing total amount, Raney's nickel accounts for the 2.5wt% of first paragraph hydrogenation reaction thing total amount, is 40 ℃ in temperature of reaction, and reaction pressure is under the 8MPa, Isophthalodinitrile and hydrogen react, reaction times is 5h, obtains the m-xylene diamine reaction solution, and the second segment hydrogenation is take the gac that supports ruthenium as catalyzer, contain ruthenium 5wt%, the add-on of catalyzer accounts for the 1wt% of second segment hydrogenation reaction thing total amount, is 80 ℃ in temperature of reaction, and reaction pressure is under the 8MPa, m-xylene diamine reaction solution and hydrogen are proceeded reaction, reaction times is 6h, prepares 1,3-cyclohexyl dimethylamine.
Embodiment 5
A kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, the method is carried out two-stage hydrogenation under same solvent, the first paragraph hydrogenation is take Raney's nickel as catalyzer, 1, the 4-dioxane is solvent, and the sodium hydroxide of 50wt% is auxiliary agent, and solvent accounts for the 60wt% of first paragraph hydrogenation reaction thing total amount, auxiliary agent accounts for the 1wt% of first paragraph hydrogenation reaction thing total amount, Raney's nickel accounts for the 3wt% of first paragraph hydrogenation reaction thing total amount, is 50 ℃ in temperature of reaction, and reaction pressure is under the 6MPa, Isophthalodinitrile and hydrogen react, reaction times is 2h, obtains the m-xylene diamine reaction solution, and the second segment hydrogenation is take the gac that supports ruthenium as catalyzer, contain ruthenium 5wt%, the add-on of catalyzer accounts for the 2wt% of second segment hydrogenation reaction thing total amount, is 90 ℃ in temperature of reaction, and reaction pressure is under the 6MPa, m-xylene diamine reaction solution and hydrogen are proceeded reaction, reaction times is 2h, prepares 1,3-cyclohexyl dimethylamine.
Embodiment 6
A kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, the method is carried out two-stage hydrogenation under same solvent, the first paragraph hydrogenation is take Raney's nickel as catalyzer, methyl alcohol and methylamine are solvent, the sodium hydroxide of 50wt% is auxiliary agent, solvent accounts for the 90wt% of first paragraph hydrogenation reaction thing total amount, and auxiliary agent accounts for the 4wt% of first paragraph hydrogenation reaction thing total amount, and Raney's nickel accounts for the 6wt% of first paragraph hydrogenation reaction thing total amount, it is 70 ℃ in temperature of reaction, reaction pressure is under the 7MPa, and Isophthalodinitrile and hydrogen react, and the reaction times is 3h, obtain the m-xylene diamine reaction solution, the second segment hydrogenation contains ruthenium 5wt% take the gac that supports ruthenium as catalyzer, and the add-on of catalyzer accounts for the 4wt% of second segment hydrogenation reaction thing total amount, it is 110 ℃ in temperature of reaction, reaction pressure is under the 7MPa, and m-xylene diamine reaction solution and hydrogen are proceeded reaction, and the reaction times is 4h, prepare 1,3-cyclohexyl dimethylamine.
Embodiment 7
A kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, the method is carried out two-stage hydrogenation under same solvent, the first paragraph hydrogenation is take Raney's nickel as catalyzer, methyl alcohol is solvent, organic amine is auxiliary agent, solvent accounts for the 80wt% of first paragraph hydrogenation reaction thing total amount, and auxiliary agent accounts for the 6wt% of first paragraph hydrogenation reaction thing total amount, and Raney's nickel accounts for the 6wt% of first paragraph hydrogenation reaction thing total amount, it is 80 ℃ in temperature of reaction, reaction pressure is under the 8MPa, and Isophthalodinitrile and hydrogen react, and the reaction times is 5h, obtain the m-xylene diamine reaction solution, the second segment hydrogenation contains ruthenium 5wt% take the gac that supports ruthenium as catalyzer, and the add-on of catalyzer accounts for the 4wt% of second segment hydrogenation reaction thing total amount, it is 130 ℃ in temperature of reaction, reaction pressure is under the 8MPa, and m-xylene diamine reaction solution and hydrogen are proceeded reaction, and the reaction times is 6h, prepare 1,3-cyclohexyl dimethylamine.
Claims (8)
1. one kind prepares 1, the method of 3-cyclohexyl dimethylamine, it is characterized in that, the method is carried out two-stage hydrogenation under same solvent, the first paragraph hydrogenation is take Raney's nickel as catalyzer, methyl alcohol, methylamine or 1, in the 4-dioxane one or more are solvent, organic amine, liquefied ammonia, water or sodium hydroxide are auxiliary agent, are 40-80 ℃ in temperature of reaction, and reaction pressure is under the 5-8MPa, Isophthalodinitrile and hydrogen react, reaction times is 1-5h, obtains the m-xylene diamine reaction solution, and the second segment hydrogenation is take the gac that supports ruthenium as catalyzer, it is 80-130 ℃ in temperature of reaction, reaction pressure is under the 5-8MPa, and m-xylene diamine reaction solution and hydrogen are proceeded reaction, and the reaction times is 1-6h, prepare 1,3-cyclohexyl dimethylamine.
2. a kind of method for preparing 1,3-cyclohexyl dimethylamine according to claim 1 is characterized in that, the preferred Isosorbide-5-Nitrae-dioxane of described solvent; Described auxiliary agent preferred concentration is the sodium hydroxide of 50wt%.
3. according to claim 1ly a kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, it is characterized in that, described solvent accounts for the 50-90wt% of first paragraph hydrogenation reaction thing total amount, auxiliary agent accounts for the 0.6-6wt% of first paragraph hydrogenation reaction thing total amount, and Raney's nickel accounts for the 2.5-6wt% of first paragraph hydrogenation reaction thing total amount.
4. according to claim 1ly a kind ofly prepare 1, the method of 3-cyclohexyl dimethylamine, it is characterized in that, described solvent accounts for the 60-80wt% of first paragraph hydrogenation reaction thing total amount, auxiliary agent accounts for the 1-4wt% of first paragraph hydrogenation reaction thing total amount, and Raney's nickel accounts for the 3-6wt% of first paragraph hydrogenation reaction thing total amount.
5. a kind of method for preparing 1,3-cyclohexyl dimethylamine according to claim 1 is characterized in that, the preferred 50-70 of the temperature of reaction of described first paragraph hydrogenation ℃, and the preferred 5-7MPa of reaction pressure, preferred 1-3h of reaction times.
6. a kind of method for preparing 1,3-cyclohexyl dimethylamine according to claim 1 is characterized in that, contains ruthenium 5wt% in the catalyzer of the described gac that supports ruthenium, and the add-on of catalyzer accounts for the 1-5wt% of second segment hydrogenation reaction thing total amount.
7. a kind of method for preparing 1,3-cyclohexyl dimethylamine according to claim 6 is characterized in that, the add-on of described catalyzer accounts for the 2-4wt% of second segment hydrogenation reaction thing total amount.
8. a kind of method for preparing 1,3-cyclohexyl dimethylamine according to claim 1 is characterized in that, the preferred 90-110 of the temperature of reaction of described second segment hydrogenation ℃, and the preferred 5-7MPa of reaction pressure, preferred 1-4h of reaction times.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105992756A (en) * | 2013-12-11 | 2016-10-05 | 巴斯夫欧洲公司 | Method for hydrogenating aromatic compounds |
| CN111100014A (en) * | 2019-11-18 | 2020-05-05 | 名畔科技(镇江)有限公司 | Preparation method of 1, 3-cyclohexyldimethylamine |
| CN112079746A (en) * | 2020-08-21 | 2020-12-15 | 江苏维尤纳特精细化工有限公司 | Purification process and catalytic hydrogenation process of isophthalonitrile |
| CN112479897A (en) * | 2020-12-07 | 2021-03-12 | 万华化学集团股份有限公司 | Preparation process of 1, 3-cyclohexyldimethylamine |
| CN113045431A (en) * | 2021-03-01 | 2021-06-29 | 淄博尚正新材料科技有限公司 | Method for preparing 1, 3-cyclohexyl dimethylamine |
| CN113402396A (en) * | 2020-03-16 | 2021-09-17 | 中国石油化工股份有限公司 | Production method for m-xylylenediamine and co-production of 1, 3-diamine methylcyclohexane |
| CN113461543A (en) * | 2021-07-27 | 2021-10-01 | 万华化学集团股份有限公司 | Rectification purification method of 1, 3-cyclohexyldimethylamine crude product |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998881A (en) * | 1974-11-13 | 1976-12-21 | Sun Ventures, Inc. | Hydrogenation of phthalonitriles using rhodium catalyst |
| US4070399A (en) * | 1976-09-20 | 1978-01-24 | Suntech, Inc. | Hydrogenation of terephthalnitrile |
| EP0538865A1 (en) * | 1991-10-23 | 1993-04-28 | Mitsubishi Gas Chemical Company, Inc. | Process for producing bisaminomethylcyclohexane |
| EP0703213A2 (en) * | 1994-09-21 | 1996-03-27 | Mitsubishi Gas Chemical Company, Inc. | Process for producing bis(aminomethyl)cyclohexane |
-
2011
- 2011-08-04 CN CN2011102229986A patent/CN102911062A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998881A (en) * | 1974-11-13 | 1976-12-21 | Sun Ventures, Inc. | Hydrogenation of phthalonitriles using rhodium catalyst |
| US4070399A (en) * | 1976-09-20 | 1978-01-24 | Suntech, Inc. | Hydrogenation of terephthalnitrile |
| EP0538865A1 (en) * | 1991-10-23 | 1993-04-28 | Mitsubishi Gas Chemical Company, Inc. | Process for producing bisaminomethylcyclohexane |
| EP0703213A2 (en) * | 1994-09-21 | 1996-03-27 | Mitsubishi Gas Chemical Company, Inc. | Process for producing bis(aminomethyl)cyclohexane |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105992756A (en) * | 2013-12-11 | 2016-10-05 | 巴斯夫欧洲公司 | Method for hydrogenating aromatic compounds |
| CN105992756B (en) * | 2013-12-11 | 2018-09-21 | 巴斯夫欧洲公司 | The method of hydroaromatic compound |
| CN111100014A (en) * | 2019-11-18 | 2020-05-05 | 名畔科技(镇江)有限公司 | Preparation method of 1, 3-cyclohexyldimethylamine |
| CN111100014B (en) * | 2019-11-18 | 2022-05-10 | 名畔科技(镇江)有限公司 | Preparation method of 1, 3-cyclohexyldimethylamine |
| CN113402396A (en) * | 2020-03-16 | 2021-09-17 | 中国石油化工股份有限公司 | Production method for m-xylylenediamine and co-production of 1, 3-diamine methylcyclohexane |
| CN112079746A (en) * | 2020-08-21 | 2020-12-15 | 江苏维尤纳特精细化工有限公司 | Purification process and catalytic hydrogenation process of isophthalonitrile |
| CN112479897A (en) * | 2020-12-07 | 2021-03-12 | 万华化学集团股份有限公司 | Preparation process of 1, 3-cyclohexyldimethylamine |
| CN112479897B (en) * | 2020-12-07 | 2022-11-04 | 万华化学集团股份有限公司 | Preparation process of 1, 3-cyclohexyldimethylamine |
| CN113045431A (en) * | 2021-03-01 | 2021-06-29 | 淄博尚正新材料科技有限公司 | Method for preparing 1, 3-cyclohexyl dimethylamine |
| CN113461543A (en) * | 2021-07-27 | 2021-10-01 | 万华化学集团股份有限公司 | Rectification purification method of 1, 3-cyclohexyldimethylamine crude product |
| CN113461543B (en) * | 2021-07-27 | 2024-02-02 | 万华化学集团股份有限公司 | Rectification and purification method of 1, 3-cyclohexanediamine crude product |
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Application publication date: 20130206 |