CS202896B1 - 1-phenyl-2-/4-/2-methacryloyloxyethoxy/phenyl/-1,2-ethandione and process for preparing thereof - Google Patents
1-phenyl-2-/4-/2-methacryloyloxyethoxy/phenyl/-1,2-ethandione and process for preparing thereof Download PDFInfo
- Publication number
- CS202896B1 CS202896B1 CS43279A CS43279A CS202896B1 CS 202896 B1 CS202896 B1 CS 202896B1 CS 43279 A CS43279 A CS 43279A CS 43279 A CS43279 A CS 43279A CS 202896 B1 CS202896 B1 CS 202896B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- methacryloyloxyethoxy
- ethanedione
- preparing
- methacrylic acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- PAGBUXPBSJJPTH-UHFFFAOYSA-N C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(=O)C(=O)C1=CC=CC=C1 Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(=O)C(=O)C1=CC=CC=C1 PAGBUXPBSJJPTH-UHFFFAOYSA-N 0.000 claims description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- -1 2-hydroxyethoxy Chemical group 0.000 claims 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- MOKAUAZWXALXDH-UHFFFAOYSA-N 1-[4-(2-hydroxyethoxy)phenyl]-2-phenylethane-1,2-dione Chemical compound C1=CC(OCCO)=CC=C1C(=O)C(=O)C1=CC=CC=C1 MOKAUAZWXALXDH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
POPIS VYNÁLEZU
K AUTORSKÉMU OSVEDČENIU ČESKOSLOVENSKASOCIALISTICKÁREPUBLIKA( 1· ) 202896 (11) (Bl)
ÚŘAD pro vynálezy
A OBJEVY /22/ Přihlášené 19 01 79/21/, /PV 432-79/ (40) Zverejnené 30 05 80(45) Vydané 15 09 82 (51) Int, Cl? C 07 C 69/54 (75)
Autor vynálezu ZVARA IVAN ing,, LUKÁC IVAN ing. CSc. , BRATISLAVA
a HRDLOVlC PAVOL RNDr. CSc., MALACKY (54) 1 -fenyl-2-[4- (2- metakryloyloxyetoxylfenyl]-1,2- etándión a sposobjeho přípravy i
Vynález sa týká novej zlúSeníny 1-feny1-2-[4-/2-metakryloyloxyetoxy/fenyl]-1,2-etándiónuvzorca I o ^0^-CO-CO-^D^-O—CHj-CHj-O-C—C=*CHj /1/ ch3 a spósobu jej přípravy.
Sposob přípravy novej zlúíeniny, ktorá nie je známa z literatury, je možný dvorní spósobmi:buď esterifikáciou 1-feny1-2-[4-/2-hydroxyetoxy/fenylj-1,2-etándiónu s kyselinou metakrylovoualebo jej chloridom alebo oxidáciou 1 -metakryloy loxy-2-: £/4-f eny lacetyl/f enoxy J-e tánu kysliční-kom seleničitým v prostředí vodného dioxánu. ·
Uvedená zlúčenina je monomer na přípravu polymeru so Špeciálnym použitím. Přikladl 3,4 g /0,01260 mol/ 1-feny1-2-[4-/2-hydroxyetoxy/fenylj- 1,2-etándiónu sa rozpustilov benzene /20 ml/, přidalo sa 1,6 g kyseliny metakrylovej /502 nadbytok/ a 5 kvapiek koncentro-vanej kyseliny sírovej. Z reakčnej zmesi sa za refluxu oddes ti 1 oval o teoretické množstvo vody.Po vychladnutí sa reakčná zmes naníesla na krátku chromátografickú kolonku /3x5 cm/ plněnusilikagélom a eluovala sa s 200 ml benzenu". Benzén sa vákuovo odpařil bez- zahrievania v trne.
Po odpaření benzenu k viskóznemu odparku sa přidal metanol, po pretrepaní odparok stuhol.Opatrné sa to zahriatím rozpustilo a nechalo krystalizovat. Získala sa svetložltá krystalickálátka s t.t. 72,0-73,0 °C a 78,52 výtažkom.
Rovnaký. produkt sa získal i esterifikáciou s chloridom kyseliny metakrylovej. 202896
Claims (3)
- 202896 2 P r í k 1 a d 2 1 mál 1-me takry loyloxy-2_£/4-f enylacě-ty l/-f enoxy j-e tánu sa rozpustil v dioxáne a přidalsa k němu roztok 1,1 molu kysližníka seleniSitého a 1,1 molu vody v dioxáne /dioxán sa pridávv.1 až dvojnásobku hmotnosti SeO,,/ a zmes sa refluxuje 12 hodin. Po tomto čase sa reakSnázmes přefiltruje, dioxán sa vákuovo odpaří a produkt sa krystalizuje z etanolu. 1 H NMR /CDClj/ delta s 2,33 Cs, 3H/-CH3/Js 4,82 /m, 4H/-OCH2CH2-O//j 5,97 s, 1H/CH2 « = C-//; 6,5/s, 1H/CH2 » C-//; 7,88/M, 9H arom/. elem. analýza vyp. C = 70,99 Z nájdené C = 71,57 XH = 5,36 X H = 5,54 X PREDMEŤ VYNÁLEZU 1. 1-fenyl-2-[4y2-metakryloyloxyetoxy/feny1^-1,2_etándión vzorca I T /o\-CO-CO-/oVo- CH2-CH2-Ó- c- c-ch2 I ch3 /1/
- 2. Sposob přípravy novej zlúíeniny podlá bodu 1, vyznačujúci sa tým, že 1-fenyl-2--C4-/2-hydroxyetoxy/-fenylj-1,2-etándión vzorca II ^O^-CO -CO-^O^-O-CHj-CHj-OH /11/ sa esterifikuje s kyselinoú metakrylovou alebo s chloridom kyseliny metakrylovej.
- 3. Sp5sob přípravy novej zlúčeniny podlá bodu 1, vyznačujúci sa tým, že 1-raetakryloyloxy -2-[/4-fenylacetyl/fenoxyJ-etán vzorca III <O> CH2-CO-(C^-O-CHj- CH2-O-C-C-CHjch3 /111/ sa oxiduje kysličníkom seleničitým v prostředí vodného dioxánu pri refluxe. Sřvrropafia. n. p.. xávod 7. Moet
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS43279A CS202896B1 (en) | 1979-01-19 | 1979-01-19 | 1-phenyl-2-/4-/2-methacryloyloxyethoxy/phenyl/-1,2-ethandione and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS43279A CS202896B1 (en) | 1979-01-19 | 1979-01-19 | 1-phenyl-2-/4-/2-methacryloyloxyethoxy/phenyl/-1,2-ethandione and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202896B1 true CS202896B1 (en) | 1981-02-27 |
Family
ID=5336365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS43279A CS202896B1 (en) | 1979-01-19 | 1979-01-19 | 1-phenyl-2-/4-/2-methacryloyloxyethoxy/phenyl/-1,2-ethandione and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS202896B1 (cs) |
-
1979
- 1979-01-19 CS CS43279A patent/CS202896B1/cs unknown
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