CN102351837A - Novel method for preparing vinylene carbonate - Google Patents
Novel method for preparing vinylene carbonate Download PDFInfo
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- CN102351837A CN102351837A CN2011103673993A CN201110367399A CN102351837A CN 102351837 A CN102351837 A CN 102351837A CN 2011103673993 A CN2011103673993 A CN 2011103673993A CN 201110367399 A CN201110367399 A CN 201110367399A CN 102351837 A CN102351837 A CN 102351837A
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- Prior art keywords
- vinylene carbonate
- novel method
- triethylamine
- preparation
- reaction
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- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 238000004821 distillation Methods 0.000 claims description 24
- AGQKYUPKNZGEQS-UHFFFAOYSA-N C(C)(=O)OC=C.C(O)(=O)Cl Chemical compound C(C)(=O)OC=C.C(O)(=O)Cl AGQKYUPKNZGEQS-UHFFFAOYSA-N 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 238000009413 insulation Methods 0.000 claims description 8
- 238000010792 warming Methods 0.000 claims description 3
- 210000003298 dental enamel Anatomy 0.000 claims description 2
- -1 enamel Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 6
- 230000000192 social effect Effects 0.000 abstract description 2
- OYOKPDLAMOMTEE-UHFFFAOYSA-N 4-chloro-1,3-dioxolan-2-one Chemical compound ClC1COC(=O)O1 OYOKPDLAMOMTEE-UHFFFAOYSA-N 0.000 abstract 2
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 239000012043 crude product Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000011837 pasties Nutrition 0.000 description 3
- 238000012805 post-processing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a novel method for preparing vinylene carbonate, which comprises the following steps: reacting monochloroethylene carbonate and triethylamine for 1.5-5 hours while controlling the temperature at 45-100 DEG C; and after the reaction finishes, distilling the reaction system to obtain the vinylene carbonate, wherein the mol ratio of monochloroethylene carbonate to triethylamine is 1:(1-4). The novel method for preparing vinylene carbonate has the following outstanding advantages: firstly, the reaction does not need any solvent, and has no solvent consumption, thereby lowering the cost and enhancing the benefit; secondly, the invention is greener and more environment-friendly as compared with the preparation process in which a solvent participates; thirdly, the preparation method disclosed by the invention is simpler to operate, and the product quality is equivalent to that of the reaction in which a solvent participates; and the invention has high practicality, and can generate high economic benefit and social effect.
Description
Technical field
The invention belongs to the organic compound synthesis technical field, be specifically related to a kind of novel method for preparing vinylene carbonate.
Background technology
Vinylene carbonate, fusing point 19-22 ℃, 162 ℃ of boiling points, its structural formula is:
When vinylene carbonate uses as the lithium ion battery electrolysis additive, require its content at 99.95wt%, moisture content is below 20ppm.Preparing method commonly used is gone up in industry at present need use high amounts of solvents, and solvent-oil ratio is bigger, and cost is high, and is uneconomical.In addition; Post-treating method commonly used in the industry need use filter type to carry out solid-liquid separation; Complex equipments; Operation easier is bigger; And because solid-liquid separation is not thorough; Cause material waste easily, and problem such as solids aftertreatment difficulty, can't satisfy the requirements of green environmental protection of modern chemistry industry.
Summary of the invention
Goal of the invention: to the deficiency that exists in the prior art; The purpose of this invention is to provide a kind of novel method for preparing vinylene carbonate; Guarantee under the product quality premise to be implemented in; Do not use solvent; And the advanced isolation technique of employing; Reduce cost, be convenient to suitability for industrialized production, meet the requirements of green environmental protection of modern chemistry industry.
Technical scheme: in order to realize the foregoing invention purpose, the technical scheme that the present invention adopts is following:
A kind of novel method for preparing vinylene carbonate, 45 ~ 100 ℃ of temperature controls react a chlorocarbonic acid vinyl acetate and triethylamine 1.5 ~ 5h, and after the end, the distillation reaction system gets vinylene carbonate.Wherein, the mol ratio of a chlorocarbonic acid vinyl acetate and triethylamine is 1:1 ~ 4, preferred 1:1 ~ 2; Temperature is preferably 50 ~ 80 ℃.Distillation is preferably underpressure distillation, and vacuum tightness is 500 ~ 1000Pa.
The novel method of above-mentioned preparation vinylene carbonate; Be specially: in reaction vessel, add a chlorocarbonic acid vinyl acetate; Stir, be warming up to 45 ~ 100 ℃, drip triethylamine 1.5 ~ 2.5h; Insulation 1.5 ~ 2.5h; Cool to room temperature is transferred to and is carried out underpressure distillation in the distiller, gets vinylene carbonate; Wherein, the vacuum tightness of underpressure distillation is 500 ~ 1000Pa.This reaction also can adopt chlorocarbonic acid vinyl acetate dropping triethylamine to carry out.
This method is not used solvent in the process of synthesized vinylene carbonate; When reaction finishes; Reacting phase is a solid particulate suspension-s; Directly transfer to this suspension-s in the distiller; Without solid-liquid separation, but directly carry out the underpressure distillation operation, receive the vinylene carbonate crude product; Residual solid is exsiccant powdered granule comparatively in the distiller, can directly collect.
Select for use distiller should be high temperature resistant and not with the material of material generation chemical reaction, like glass, enamel, stainless steel, tetrafluoroethylene etc.Its support equipment also should possess above characteristic.In addition,, thereby cause material to disperse difficulty to become big, therefore, be heated evenly, must adopt the stirring system of better performances for guaranteeing material because liquid phase part can reduce gradually in still-process.
Beneficial effect: the novel method of preparation vinylene carbonate of the present invention, the outstanding advantage that has comprises: at first, reaction need not solvent and participates in, and solvent-free consumption has reduced cost; Need not equipment for separating liquid from solid, reduced number of devices and operation steps, thereby reduced equipment cost; Improved benefit; Secondly, compare environmental protection more with the preparation process that has solvent to participate in; Once more, compare the solid-liquid separation process, improved yield and post-treating method and operated more simple.Have good practicability, can produce good economic benefits and social effect.
Embodiment
Below in conjunction with specific embodiment the present invention is done further explanation.
Embodiment 1
In 5000ml four-hole reaction flask, add 1512g one chlorocarbonic acid vinyl acetate (content is 81wt%); Connect after the device such as condenser blow-down pipe; Open and stir; Open heating; Be warmed up to 50 ℃; Drip the 2020g triethylamine with constant pressure funnel then; The dropping time is controlled at 1.5 ~ 2.5h; Drip after the end; Insulation 1.5 ~ 2.5h, cool to room temperature is transferred to and is carried out the underpressure distillation that vacuum tightness is 500 ~ 1000Pa in the distiller then; Obtain 791g vinylene carbonate crude product, wherein the content of vinylene carbonate is 83.5wt%.
Embodiment 2
In 5000ml four-hole reaction flask, add the 2020g triethylamine; Connect after the device such as condenser blow-down pipe; Open and stir; Open heating; Be warmed up to 50 ℃; Drip 1512g one chlorocarbonic acid vinyl acetate (content is 81wt%) with constant pressure funnel then; The dropping time is controlled at 1.5 ~ 2.5h; Drip after the end; Insulation 1.5 ~ 2.5h, cool to room temperature is transferred to and is carried out the underpressure distillation that vacuum tightness is 500 ~ 1000Pa in the distiller then; Obtain 769g vinylene carbonate crude product, wherein the content of vinylene carbonate is 86.7wt%.
Embodiment 3
The yield experimental study of different mol ratio reaction, test method is with embodiment 1, and wherein temperature of reaction is 65 ℃, and the mol ratio of a chlorocarbonic acid vinyl acetate and triethylamine is as shown in table 1, and the test-results of being carried out is specifically seen table 1.
The yield experimental study of table 1 different mol ratio reaction is table as a result
| Mol ratio | One chlorocarbonic acid vinyl acetate (g) | Triethylamine (g) | The yield of vinylene carbonate (%) |
| 1:1 | 122.5 | 101 | 71.2 |
| 1:1.25 | 122.5 | 126.25 | 74.2 |
| 1:1.5 | 122.5 | 151.5 | 79.1 |
| 1:2 | 122.5 | 202 | 76.8 |
| 1:2.5 | 122.5 | 252.5 | 74.1 |
| 1:3 | 122.5 | 303 | 73.7 |
The yield experimental study of differing temps reaction, test method is with embodiment 1, and wherein temperature of reaction is as shown in table 2, and the mol ratio of a chlorocarbonic acid vinyl acetate and triethylamine is 1:1.5, and the test-results of being carried out is specifically seen table 2.
The yield experimental study of table 2 differing temps reaction is table as a result
| One chlorocarbonic acid vinyl acetate (g) | Triethylamine (g) | Temperature of reaction ℃ | Yield (%) |
| 122.5 | 151.5 | 45 | 50.8 |
| 122.5 | 151.5 | 50 | 57.6 |
| 122.5 | 151.5 | 55 | 64.5 |
| 122.5 | 151.5 | 60 | 74.8 |
| 122.5 | 151.5 | 65 | 79.1 |
| 122.5 | 151.5 | 70 | 78.7 |
| 122.5 | 151.5 | 75 | 71.7 |
| 122.5 | 151.5 | 80 | 65.7 |
Visible from table 1 and table 2, this preparation method can realize yield preferably in the temperature of broad and molar ratio range, can satisfy production requirement.
Embodiment 4
In 5000ml four-hole reaction flask, add 1512g one chlorocarbonic acid vinyl acetate (content is 81wt%); Connect after the device such as condenser blow-down pipe; Open and stir; Open heating, be warmed up to 50 ℃, drip the 2020g triethylamine with constant pressure funnel then; The dropping time is controlled at 2h; Drip after the end, insulation 2h obtains pasty state mixed phase 3508g.Uniformly this mixed phase is divided into two groups, every group is 1754g, and volume is No. 1 and No. 2.
No. 1 sample is carried out centrifugal treating, the centrifugal 600 order cloth bags of selecting for use, rotating speed is 1200r/min, is centrifugal terminal point with dripless in the discharge port 5min.Gained filtrating transferred to carry out underpressure distillation in the water distilling apparatus, distillation finishes to obtain vinylene carbonate crude product 357g, and content is 88.4%.
No. 2 samples are carried out post-treating method of the presently claimed invention carry out underpressure distillation, distillation finishes to obtain vinylene carbonate crude product 396g, and content is 83.5wt%.
Embodiment 5
In 5000ml four-hole reaction flask, add the 2020g triethylamine; Connect after the device such as condenser blow-down pipe; Open and stir; Open heating, be warmed up to 50 ℃, drip 1512g one chlorocarbonic acid vinyl acetate (content is 81wt%) with constant pressure funnel then; The dropping time is controlled at 2h; Drip after the end, insulation 2h obtains pasty state mixed phase 3498g.Uniformly this mixed phase is divided into two groups, every group is 1754g, and volume is No. 1 and No. 2.
No. 1 sample is carried out centrifugal treating, the centrifugal 600 order cloth bags of selecting for use, rotating speed is 1200r/min, is centrifugal terminal point with dripless in the discharge port 5min.Gained filtrating transferred to carry out underpressure distillation in the water distilling apparatus, distillation finishes to obtain vinylene carbonate crude product 351g, and content is 87.4%.
No. 2 samples are carried out post-treating method of the presently claimed invention carry out underpressure distillation, distillation finishes to obtain vinylene carbonate crude product 385g, and content is 86.7wt%.
Embodiment 6
In the 10000ml reactor, add 3024g one chlorocarbonic acid vinyl acetate (content is 81wt%); Connect after the device such as condenser blow-down pipe; Open and stir; Open heating, be warmed up to 65 ℃, drip the 4040g triethylamine with constant pressure funnel then; The dropping time is controlled at 2h; Drip after the end, insulation 2h obtains pasty state mixed phase 6995g.
According to following method, this reaction mixed phase is divided into 5 parts uniformly, obtain the crude product of vinylene carbonate through different post processing modes (table 3), carry out the comparative studies of yield.The test-results of being carried out is specifically seen table 3.
The different post processing mode comparative studies of table 3 result
| Numbering | Mixed phase weight (g) | Post processing mode | Vinylene carbonate crude product weight (g) | Vinylene carbonate content in crude product (%) | Weighting weight (g) |
| 1 | 1399 | Whizzer is centrifugal | 296 | 84.1 | 249 |
| 2 | 1399 | The B vacuum filtration | 277 | 86.2 | 239 |
| 3 | 1399 | The press filtration of B nitrogen | 272 | 87.6 | 238 |
| 4 | 1399 | Standing sedimentation is poured out liquid phase | 125 | 89.0 | 111 |
| 5 | 1399 | The unified distillation of the inventive method | 319 | 81.2 | 259 |
Visible from table 3, preparation method of the present invention has better yield, can satisfy production requirement.
Above-described only is preferred implementation of the present invention.Should be understood that; For the person of ordinary skill of the art; Under the prerequisite that does not break away from patent principle of the present invention; Can also make some distortion and improvement, for example, according to this area general knowledge; In order further to improve reaction yield; But described dropping and soaking time proper extension or shortening, material proportions etc. also can suitably be adjusted, and these also should be considered as protection scope of the present invention.
Claims (8)
1. novel method for preparing vinylene carbonate is characterized in that: 45 ~ 100 ℃ of temperature controls, react a chlorocarbonic acid vinyl acetate and triethylamine 1.5 ~ 5h, and after the end, the distillation reaction system gets vinylene carbonate; Wherein, the mol ratio of a chlorocarbonic acid vinyl acetate and triethylamine is 1:1 ~ 4.
2. the novel method of preparation vinylene carbonate according to claim 1 is characterized in that: the mol ratio of a chlorocarbonic acid vinyl acetate and triethylamine is 1:1 ~ 2.
3. the novel method of preparation vinylene carbonate according to claim 1 is characterized in that: temperature is 50 ~ 80 ℃.
4. the novel method of preparation vinylene carbonate according to claim 1 is characterized in that: distill and be that underpressure distillation, vacuum tightness are 500 ~ 1000Pa.
5. the novel method of preparation vinylene carbonate according to claim 1; It is characterized in that: in reaction vessel, add a chlorocarbonic acid vinyl acetate; Stir, be warming up to 45 ~ 100 ℃, drip triethylamine 1.5 ~ 2.5h; Insulation 1.5 ~ 2.5h; Cool to room temperature is transferred to and is carried out underpressure distillation in the distiller, gets vinylene carbonate; Wherein, the vacuum tightness of underpressure distillation is 500 ~ 1000Pa.
6. the novel method of preparation vinylene carbonate according to claim 1; It is characterized in that: in reaction vessel, add triethylamine; Stir, be warming up to 45 ~ 100 ℃, drip a chlorocarbonic acid vinyl acetate 1.5 ~ 2.5h; Insulation 1.5 ~ 2.5h; Cool to room temperature is transferred to and is carried out underpressure distillation in the distiller, gets vinylene carbonate; Wherein, the vacuum tightness of underpressure distillation is 500 ~ 1000Pa.
7. according to the novel method of claim 1,5 or 6 described preparation vinylene carbonates, it is characterized in that: the material of the distiller that said underpressure distillation is used be high temperature resistant and not with the material of material generation chemical reaction.
8. the novel method of preparation vinylene carbonate according to claim 7 is characterized in that: material is glass, enamel, stainless steel or tetrafluoroethylene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103673993A CN102351837A (en) | 2011-11-18 | 2011-11-18 | Novel method for preparing vinylene carbonate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103673993A CN102351837A (en) | 2011-11-18 | 2011-11-18 | Novel method for preparing vinylene carbonate |
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| CN102351837A true CN102351837A (en) | 2012-02-15 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804340A (en) * | 2012-11-06 | 2014-05-21 | 中国科学院理化技术研究所 | Preparation method of vinylene carbonate |
| CN106632225A (en) * | 2016-12-27 | 2017-05-10 | 苏州华新能源科技有限公司 | Method for preparing high-purity vinylene carbonate |
| CN106749155A (en) * | 2017-01-06 | 2017-05-31 | 淮安瀚康新材料有限公司 | A kind of method that microchannel plate should prepare vinylene carbonate |
| CN113336736A (en) * | 2021-05-31 | 2021-09-03 | 多氟多新材料股份有限公司 | Method for preparing vinylene carbonate |
| CN114133371A (en) * | 2021-12-09 | 2022-03-04 | 泰兴华盛精细化工有限公司 | Method for synthesizing vinylene carbonate at low temperature |
| CN114835670A (en) * | 2022-06-16 | 2022-08-02 | 浙江天硕氟硅新材料科技有限公司 | Method for preparing high-purity vinylene carbonate |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB957003A (en) * | 1961-03-28 | 1964-04-29 | Huels Chemische Werke Ag | Improvements in the production of vinylene carbonate |
| CN1304935A (en) * | 1999-11-19 | 2001-07-25 | 默克专利股份有限公司 | Preparation method of vinylene carbonate and its application |
| DE102004020443A1 (en) * | 2004-04-27 | 2005-07-14 | Lenze, Norman, Dr. | Preparation of vinylene carbonate by dehydrogenation of monohaloethylene carbonate is carried out in ether, preferably methyl tert.-butyl ether, as solvent |
| CN1995033A (en) * | 2006-12-19 | 2007-07-11 | 太仓华一化工科技有限公司 | Vinylene carbonate synthesis method |
| CN101171242A (en) * | 2005-05-12 | 2008-04-30 | 赛拓有限责任公司 | Process for producing vinylene carbonate |
-
2011
- 2011-11-18 CN CN2011103673993A patent/CN102351837A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB957003A (en) * | 1961-03-28 | 1964-04-29 | Huels Chemische Werke Ag | Improvements in the production of vinylene carbonate |
| CN1304935A (en) * | 1999-11-19 | 2001-07-25 | 默克专利股份有限公司 | Preparation method of vinylene carbonate and its application |
| DE102004020443A1 (en) * | 2004-04-27 | 2005-07-14 | Lenze, Norman, Dr. | Preparation of vinylene carbonate by dehydrogenation of monohaloethylene carbonate is carried out in ether, preferably methyl tert.-butyl ether, as solvent |
| CN101171242A (en) * | 2005-05-12 | 2008-04-30 | 赛拓有限责任公司 | Process for producing vinylene carbonate |
| CN1995033A (en) * | 2006-12-19 | 2007-07-11 | 太仓华一化工科技有限公司 | Vinylene carbonate synthesis method |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804340A (en) * | 2012-11-06 | 2014-05-21 | 中国科学院理化技术研究所 | Preparation method of vinylene carbonate |
| CN106632225A (en) * | 2016-12-27 | 2017-05-10 | 苏州华新能源科技有限公司 | Method for preparing high-purity vinylene carbonate |
| CN106632225B (en) * | 2016-12-27 | 2018-06-26 | 苏州华一新能源科技有限公司 | A kind of preparation method of high-purity vinylene carbonate |
| CN106749155A (en) * | 2017-01-06 | 2017-05-31 | 淮安瀚康新材料有限公司 | A kind of method that microchannel plate should prepare vinylene carbonate |
| CN113336736A (en) * | 2021-05-31 | 2021-09-03 | 多氟多新材料股份有限公司 | Method for preparing vinylene carbonate |
| CN114133371A (en) * | 2021-12-09 | 2022-03-04 | 泰兴华盛精细化工有限公司 | Method for synthesizing vinylene carbonate at low temperature |
| CN114835670A (en) * | 2022-06-16 | 2022-08-02 | 浙江天硕氟硅新材料科技有限公司 | Method for preparing high-purity vinylene carbonate |
| CN114835670B (en) * | 2022-06-16 | 2023-03-21 | 浙江天硕氟硅新材料科技有限公司 | Method for preparing high-purity vinylene carbonate |
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Application publication date: 20120215 |