CS201971B1 - Tertiary butyl-/2,3-dimethyl-3-brom/butyl-2-peroxide and process for preparing thereof - Google Patents
Tertiary butyl-/2,3-dimethyl-3-brom/butyl-2-peroxide and process for preparing thereof Download PDFInfo
- Publication number
- CS201971B1 CS201971B1 CS234379A CS234379A CS201971B1 CS 201971 B1 CS201971 B1 CS 201971B1 CS 234379 A CS234379 A CS 234379A CS 234379 A CS234379 A CS 234379A CS 201971 B1 CS201971 B1 CS 201971B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- butyl
- dimethyl
- peroxide
- brom
- preparing
- Prior art date
Links
- -1 butyl- Chemical group 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- FVBHYZVVSXFCOO-UHFFFAOYSA-N tert-butyl hydrogen sulfate Chemical compound CC(C)(C)OS(O)(=O)=O FVBHYZVVSXFCOO-UHFFFAOYSA-N 0.000 claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
- 235000011089 carbon dioxide Nutrition 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 1
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- UAJUDVMLDWICLE-UHFFFAOYSA-N bromooxy hypobromite Chemical class BrOOBr UAJUDVMLDWICLE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká novej zlúčeniny terc.butyl - /2.3-dimetyl-3-bróm/butyl -2-peroxidu vzorca
CH, CH, CH,
I J I I J
CH, - C -0 - 0 - C - C -Br l· II
CH3 ch3 ch3 a spósobu jeho přípravy.
Doteraz sa podařilo pripraviť metodou peroxymerkurécie brómperoxidy s brómom v /^-polohe v peroxyskupine len na sekundárnom uhlíku /A.J. Bloodworth} I.M, Griffin, J. Chem,
Soc. Perkin, Transaetion I. 1975, 695/.
Předložený vynález využívá spósob přípravy nesubstituovanýeh peroxidov, ktorý je založený na peroxidécii hydroperoxidu s terc.butylhydrogánsulfétom /N.A. Milas, D.M. Surgenol, J. Am. Chem. Soc., 68, 1946/ str. 205 a 643/. ,
Spósob přípravy novej zlúčeniny je založený na tom, že na 2,3-dimetyl - 3 - brómbutyl - 2 - bydroperoxid sa pósobí terč, butylhydrogénsulfétom.
Význam uvedenej zlúčeniny spočívá v jej použití ako iniciátora radikálových reakcií, napr. radikálovéj polymerizácie.
201 971
Příklad
K 6,1 g 2,3-dimetyl-3-brómbutyl-2-hydroperoxidu sa při teplote suchého l'adu v metanole za miešania přidal postupné studený roztok terč. butylhydrogénsulfátu připravený zmiešením zriedenej kyseliny sírovej /3,2 ml konc. HgSO^ + 1,2 ml vody/ s terč. butanolom /4,8 ml./. Po zhomogenizovaní sa zmes miešala pri teplote miestnosti 2 hodiny a nechala stéť do druhého dňa bez miešania. Reakčná zmes sa zriedila dietyléterom a premyla 3-krát vodou. Po vákuovom odpaření éteru sa produkt zriedil n-hexénom a přefiltroval cez 4 cm stípec silikagélu. Po odpaření n-hexánu sa získalo 6 g kvapalného produktu /nD 2θ = 1,4498/ Produkt je možné čistiť i destiláciou /t.v. 61 °C/133 Pa/, avšak produkt velmi pění. Pre zamedzenie premenia okrem varnej kapiláry sa použila ďalšia nad hladinou na rozréžanie pěny. Kvalita produktu čištěného chromátograficky bola podobná s kvalitou destilovaného. Elementárna analýza pre C1Q Hg^ Og Br vypočítané: C = 47,44; H = 8,36; Br = 31,56 nájdené:
C » 47,97; H - 8,99; Br = 34,16. Infračervené spektrum /CCl^/: ^max = 600, 840, 890,,1 110, 1 165, 1 205, 1 250, 1 370, 1 380, 1 465, 2 960, 3 000 cm-1. NMR /CCl^/ : 1,18 /s,9H, C/CH3/3/; 1,40 /β, 6H, Br-C/CH3/2 -/; 1,78 /s, 6H, -0- C/CH3/2 -/. Hmotné spektrum: m/e = 252 /M+/; 195, 179, 163, 165, 131, 121, 123, 73, 69, 57.
PREDMETVYHÍLEZU
Claims (2)
1..Terc.butyl - /2,3 - dimetyl - 3 - bróm/butyl - 2 -peroxid vzorca /
• CH, CH, CH,
I 3 I 3 I 3
CH, - C - 0 - 0 - C - C - Br.
I I I
CH3 ch3 ch3 ,
2. Spdsob přípravy zlúčeniny podl’a bodu 1 vyznačujúci sa tým, že na 2,3 - dimetyl - 3 - bróm/butyl - 2 - hydroperoxid sa pdsobí terc.butylhydrogénaulfátom pri teplote suchého 1’adu v metanole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS234379A CS201971B1 (en) | 1979-04-06 | 1979-04-06 | Tertiary butyl-/2,3-dimethyl-3-brom/butyl-2-peroxide and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS234379A CS201971B1 (en) | 1979-04-06 | 1979-04-06 | Tertiary butyl-/2,3-dimethyl-3-brom/butyl-2-peroxide and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS201971B1 true CS201971B1 (en) | 1980-12-31 |
Family
ID=5360268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS234379A CS201971B1 (en) | 1979-04-06 | 1979-04-06 | Tertiary butyl-/2,3-dimethyl-3-brom/butyl-2-peroxide and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS201971B1 (cs) |
-
1979
- 1979-04-06 CS CS234379A patent/CS201971B1/cs unknown
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