CN100427490C - Process for preparing allyl chlorosilane - Google Patents
Process for preparing allyl chlorosilane Download PDFInfo
- Publication number
- CN100427490C CN100427490C CNB2006100505552A CN200610050555A CN100427490C CN 100427490 C CN100427490 C CN 100427490C CN B2006100505552 A CNB2006100505552 A CN B2006100505552A CN 200610050555 A CN200610050555 A CN 200610050555A CN 100427490 C CN100427490 C CN 100427490C
- Authority
- CN
- China
- Prior art keywords
- allyl
- earth metal
- chlorsilane
- rare earth
- chlorallylene
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- -1 allyl chlorosilane Chemical compound 0.000 title claims abstract description 18
- 239000005046 Chlorosilane Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 19
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims abstract description 10
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 229910000077 silane Inorganic materials 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052772 Samarium Inorganic materials 0.000 claims description 6
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052779 Neodymium Inorganic materials 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 abstract description 3
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005052 trichlorosilane Substances 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGTJLJZQQFGTJD-UHFFFAOYSA-N Carbonylcyanide-3-chlorophenylhydrazone Chemical compound ClC1=CC=CC(NN=C(C#N)C#N)=C1 UGTJLJZQQFGTJD-UHFFFAOYSA-N 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- MVKRJEALUDVITB-UHFFFAOYSA-N [SiH4].C(C)Cl Chemical compound [SiH4].C(C)Cl MVKRJEALUDVITB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- YCITZMJNBYYMJO-UHFFFAOYSA-N chloro(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](Cl)C1=CC=CC=C1 YCITZMJNBYYMJO-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
The present invention relates to a method for preparing allyl chlorsilane by a rare earth metal catalyst. With the action pf the rare earth metal catalyst, the allyl chlorsilane can be synthesized by the coupling reaction between dichlorosilane or trichlorosilane and allyl bromide. The present invention solves the problems in the prior art. The preparation method of the present invention is characterized in that the chlorsilane and the allyl bromide are dissolved in an organic solvent under the protection of nitrogen, and the earth metal is added as a catalyst; next, the chlorsilane and the allyl bromide are sufficiently stirred for sufficient reaction, and are placed statically and filtered. An allyl chlorsilane monomer can be obtained by the depressurization distillation of filter liquor, and has a general formula (1) of R (Allyl) x Si (Cl) y(1).
Description
Technical field
The present invention relates to organic chemistry filed, specifically is a kind of method for preparing chlorallylene silane with rare-earth metal catalyst.
Background technology
Organic halosilanes, R
nSiX
4-n(R=Me, Et, Vi, Allyl, Pr, Ph etc.; X=F, Cl, Br, I; N=1-3), particularly containing the chlorallylene silane of unsaturated double-bond, is the important source material of preparation organosilicon polymer (as: silicone oil, silicon rubber, silicone resin) and other functionalized silicon, carbon functional silane.
But the preparation method of chlorallylene silane is but very limited.Existing synthetic method mainly comprises: a) organometallics method (US 2698333,19540); B) hydrosilation additive process (spy opens flat 2-290886.1990 communique); C) pyrocondensation legal (CCCP OXH, 1956:630); D) direct synthesis technique (DD 5348.1942) etc.But method a) often obtains the blended hydrocarbyl si lanes, and uses a large amount of solvents, and is inflammable and explosive; B) method need be used valuable transition metal platinum, palladium etc.; C) the legal temperature of reaction of pyrocondensation higher (600 ℃) often has a certain proportion of by product to generate the separation difficulty of principal product; D) method is occupying an important position aspect synthetic ethyl chloride silane and the arylchlorosilane, also is not overripened but be used for the technology of the synthetic bright basic chlorosilane of alkene.
Summary of the invention
Main purpose of the present invention provides the method for a gentleness, safe and effective synthesis of allyl chlorosilane.Under catalyzing of rare-earth metal, by the linked reaction between dichlorosilane or trichlorosilane and allyl bromide 98, synthesis of allyl chlorosilane.Can solve more existing problems in the prior art well with catalyzing of rare-earth metal synthesis of allyl chlorosilane.
The preparation method of chlorallylene silane of the present invention is characterized in that: under nitrogen protection, chlorosilane and allyl bromide 98 are dissolved in the organic solvent, add rare earth metal then as catalyzer, fully stir, fully reaction is filtered; Filtrate is carried out underpressure distillation, just can obtain the alkyl chlorosilane that allyl group replaces, i.e. chlorallylene silane monomer, its general formula is (1):
R (CH
2=CHCH
2)
xSi (Cl)
y(1), x in the formula, y=1,2
R=CH
3, CH
2CH
3, vinyl, allyl group, H, CH
2CH
2OR,
R′＝H，Cl，F，CH
3，OCH
3
，
R in the formula
1, R
2, R
3Identical with the R in the above-mentioned general formula (1);
Described solvent is a tetrahydrofuran (THF) (THF), 1, and the mixture of one or more in 2-glycol dimethyl ether (DME), benzene, normal hexane, hexanaphthene, toluene, the dimethylbenzene is preferably toluene;
Described rare earth metal (Ln) catalyzer is: lanthanum (La), and cerium (Ce), neodymium (Nd), samarium (Sm), the mixture of a kind of in the ytterbium (Yb) or two kinds is preferably rare earth metal samarium (Sm).
The present invention uses rare earth metal (Ln) catalyzer, and by the linked reaction synthesis of allyl alkyl chlorosilane between chlorosilane and allyl bromide 98, concrete synthetic route is as follows in non-proton organic solvent:
R in the formula
1, R
2, R
3Identical with the R in the above-mentioned general formula (1).
The invention effect
A) use industrial raw material, do not need harsh reaction conditions, synthesis of allyl alkyl chlorosilane under the condition of gentleness;
B) use rare-earth metal catalyst, do not use poisonous, dangerous reagent, can safety and environmentally safe ground synthesize organopolysilane;
C) product is single, does not almost have side reaction to take place;
D) owing to the original reagent of going back of a kind of gentleness of rare earth metal, in reaction process, some particular functional groups such as carbonyl in its substrate, amide group, alkylene etc. can be not destroyed, the dehalogenation reaction can not take place simultaneously yet.
Embodiment
Below by embodiment technical solution of the present invention is further described in detail.
Embodiment 1
At one magnetic stirring apparatus is housed, places (0.1mol) rare earth metal samarium in three mouthfuls of round-bottomed flasks of the 100mL of constant pressure funnel, reflux condensing tube and air guide port device.Inject the new distillatory toluene solution of 40mL then, under nitrogen protection, in reaction flask, add excessive a little allyl bromide 98 (0.11mol), diphenyl dichlorosilane (0.1mol).Stirring at room, solution becomes red-purple after 10 minutes, and constant temperature (25 ℃) reaction is 2 hours then.It is light yellow to treat that solution becomes, stopped reaction.Filter.Underpressure distillation, (productive rate: 98%), some physical datas of this compound are as follows: IR:v promptly to obtain colourless allyl group diphenyl chlorosilane
Max(liquid film) 3070.6,2969.1,1630.0,1427.9,1112.5cm
-1 1H NMR (400MHz, CDCl
3): 7.28-7.72 (5 H, m, ArH), 5.73-5.83 (1H, m, CH), 5.05-5.09 (2H, t, CH
2=), 2.30-2.32 (2 H, d, CH
2CH=CH
2);
13C NMR (100MHz, CDCl
3): 133.96,131.77,130.82,130.53,128.13,115.66,19.40; MS:m/z (%): 258 (M
+, 3.8) and 216 (19.92), 175 (100), 77 (22.14).
Embodiment 2
At one magnetic stirring apparatus is housed, places (0.1mol) rare earth metal cerium in three mouthfuls of round-bottomed flasks of the 100mL of constant pressure funnel, reflux condensing tube and air guide port device.Inject the new distillatory tetrahydrofuran solution of 40mL then, under nitrogen protection, the allyl bromide 98 (0.11mol) that adds in the reaction flask, phenyl-trichloro-silicane (0.05mol).Stirring at room, solution becomes red-purple after 10 minutes, and constant temperature (25 ℃) reaction is 2 hours then.It is light yellow to treat that solution becomes, stopped reaction.Filter.Underpressure distillation promptly obtains colourless phenyl diallyl chlorosilane (productive rate: 95%).
Embodiment 3
At one magnetic stirring apparatus is housed, places (0.1mol) rare earth metal samarium in three mouthfuls of round-bottomed flasks of the 100mL of constant pressure funnel, reflux condensing tube and air guide port device.Inject the new distillatory xylene solution of 40mL then, under nitrogen protection, the allyl bromide 98 (0.11mol) that adds in the reaction flask, METHYL TRICHLORO SILANE (0.1mol).Stirring at room, solution becomes red-purple after 10 minutes, and reflux (110 ℃) is 12 hours then.It is light yellow to treat that solution becomes, stopped reaction.Filter.Underpressure distillation promptly obtains colourless methylene propyl group dichlorosilane (productive rate: 98%).
Claims (2)
1, a kind of preparation method of chlorallylene silane is characterized in that: under nitrogen protection, chlorosilane and allyl bromide 98 are dissolved in the organic solvent, add rare earth metal then as catalyzer, fully stir, fully reaction is filtered; Filtrate is carried out underpressure distillation, just can obtain the chlorallylene silane monomer, its general formula is: R (CH
2=CHCH
2)
xSi (Cl)
y(1), x in the formula, y=1,2
R=CH
3, CH
2CH
3, vinyl, allyl group, H,
R′＝H，Cl，F，CH
3，OCH
3
；
Described solvent is a tetrahydrofuran (THF), 1, the mixture of one or more in 2-glycol dimethyl ether, benzene, normal hexane, hexanaphthene, toluene, the dimethylbenzene;
Described rare-earth metal catalyst is: lanthanum, cerium, neodymium, samarium, the mixture of a kind of in the ytterbium or two kinds.
2, the preparation method of chlorallylene silane according to claim 1 is characterized in that described solvent is a toluene, and described catalyzer is the rare earth metal samarium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100505552A CN100427490C (en) | 2006-04-28 | 2006-04-28 | Process for preparing allyl chlorosilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100505552A CN100427490C (en) | 2006-04-28 | 2006-04-28 | Process for preparing allyl chlorosilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1880321A CN1880321A (en) | 2006-12-20 |
| CN100427490C true CN100427490C (en) | 2008-10-22 |
Family
ID=37518700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100505552A Expired - Fee Related CN100427490C (en) | 2006-04-28 | 2006-04-28 | Process for preparing allyl chlorosilane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100427490C (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101117388B (en) * | 2007-07-16 | 2010-05-26 | 杭州师范大学 | Method for preparing Si-H silicon functionalized polysilane |
| CN101143874B (en) * | 2007-11-05 | 2011-08-24 | 杭州师范大学 | Method for preparing allylchlorosilane containing different substituents |
| CN102863466B (en) * | 2012-10-11 | 2018-04-03 | 威海新元化工有限公司 | Preparation method of di (2-propenyl) dialkoxy (or dichloro) silane |
| CN105968363A (en) * | 2016-05-17 | 2016-09-28 | 江苏中路新材料科技发展有限公司 | Organic silicon resin capable of improving water damage resistance of roads as well as preparation method and application of organic silicon resin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965386A (en) * | 1990-03-26 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Hydrosilation, and dehydrocondensation of silicon hydrides, catalyzed by scandium, yttrium and rare earth metal compounds |
| CN1634935A (en) * | 2004-11-16 | 2005-07-06 | 浙江大学 | Method for CH3SiCl3 conversion reaction |
-
2006
- 2006-04-28 CN CNB2006100505552A patent/CN100427490C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965386A (en) * | 1990-03-26 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Hydrosilation, and dehydrocondensation of silicon hydrides, catalyzed by scandium, yttrium and rare earth metal compounds |
| CN1634935A (en) * | 2004-11-16 | 2005-07-06 | 浙江大学 | Method for CH3SiCl3 conversion reaction |
Non-Patent Citations (6)
| Title |
|---|
| 氨烷基硅烷偶联剂的合成. 李国威等.有机硅材料及应用，第4期. 1998 |
| 氨烷基硅烷偶联剂的合成. 李国威等.有机硅材料及应用，第4期. 1998 * |
| 烯丙基氯硅氢化反应的均相催化机理. 方白盈等.安徽师大学报（自然科学版），第19卷第4期. 1996 |
| 烯丙基氯硅氢化反应的均相催化机理. 方白盈等.安徽师大学报（自然科学版），第19卷第4期. 1996 * |
| 硅烷偶联剂KBM602的合成工艺研究. 彭以元等.江西师范大学学报（自然科学版），第22卷第2期. 1998 |
| 硅烷偶联剂KBM602的合成工艺研究. 彭以元等.江西师范大学学报（自然科学版），第22卷第2期. 1998 * |
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|---|---|
| CN1880321A (en) | 2006-12-20 |
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