CS266111B1 - 2-/4-benzoylphenyl/-2-/4-propenoylphenyl/propane - Google Patents
2-/4-benzoylphenyl/-2-/4-propenoylphenyl/propane Download PDFInfo
- Publication number
- CS266111B1 CS266111B1 CS875527A CS552787A CS266111B1 CS 266111 B1 CS266111 B1 CS 266111B1 CS 875527 A CS875527 A CS 875527A CS 552787 A CS552787 A CS 552787A CS 266111 B1 CS266111 B1 CS 266111B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzoylphenyl
- propane
- compound
- propenoylphenyl
- acetonitrile
- Prior art date
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000001294 propane Substances 0.000 title abstract description 4
- JIGQUTBMSJSFAE-UHFFFAOYSA-N 1-[4-[2-(4-benzoylphenyl)propan-2-yl]phenyl]prop-2-en-1-one Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=C(C(=O)C=C)C=C1 JIGQUTBMSJSFAE-UHFFFAOYSA-N 0.000 claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 12
- -1 4— -benzoylphenyl Chemical group 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000001632 sodium acetate Substances 0.000 abstract description 3
- 235000017281 sodium acetate Nutrition 0.000 abstract description 3
- 230000000593 degrading effect Effects 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012667 polymer degradation 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Riešenie sa týká novej zlúčeniny 2—(4— -benzoylfenyl)-2-(4-propenoyl)propánu. Uvedená zlúčenina sa připraví tak, že na 2-(4-benzoylfenyl)-2-C4-(3-chlórpropanoyl)- fenyljpropán sa pósobí octanom sodným v acetonitrile pri 50 °C. Zlúčenina je monomérom k príprave polymérov degradujúcich světlom.The solution relates to the new compound 2— (4— -benzoylphenyl) -2- (4-propenoyl) propane. The compound is prepared so that the compound of formula (I) is obtained 2- (4-benzoylphenyl) -2-4- (3-chloropropanoyl) - phenylpropane is treated with sodium acetate in acetonitrile at 50 ° C. The compound is a monomer to prepare polymers degrading light.
Description
Vynález sa týká 2-(4-benzoylfenyl)-2-(4-propenoylfenyl)propánu.The invention relates to 2- (4-benzoylphenyl) -2- (4-propenoylphenyl) propane.
Aromatické vinylketóny sa pripravujú obecne dehydrochloráciou l-aryl-3-chlór-l-propanónov (P. Hrdlovič, I. Lukáč, Developements in Polymer Degradation 4, 101,1982, Ed. N. Grassie, Applied Science Publishers Ltd.). Rovnaká metoda sa použila i na pripravu 2-(4-benzoylfenyl)-2-(4-propenoylfenyl)propánu, ktorý nie je popísaný v literatúre.Aromatic vinyl ketones are generally prepared by dehydrochlorination of 1-aryl-3-chloro-1-propanones (P. Hrdlovic, I. Lukac, Developements in Polymer Degradation 4, 101, 1982, Ed. N. Grassie, Applied Science Publishers Ltd.). The same method was used to prepare 2- (4-benzoylphenyl) -2- (4-propenoylphenyl) propane, which is not described in the literature.
Podstatou vynálezu je 2-(4-benzoylfenyl)-2-(4-propenoylfenyl)propán. Spůsob přípravy tejto zlúčeniny spočívá v tom, že na 2-(4-benzoylfenyl)-2-C4-(3-ohlórpropanoyl)fenyljpropán sa působí octanom sodným v acetonitrile pri 50 °C.The present invention provides 2- (4-benzoylphenyl) -2- (4-propenoylphenyl) propane. A method for preparing this compound is to treat 2- (4-benzoylphenyl) -2-C4- (3-chloropropanoyl) phenyl] propane with sodium acetate in acetonitrile at 50 ° C.
Výhodou uvedeného vynálezu je, že umožňuje připravit predmetnú zlúčeninu vo vysokom výtažku a jednoducho.An advantage of the present invention is that it makes it possible to prepare the subject compound in high yield and easily.
Předmětná zlúčenina je monomérom k príprave polymérov degradujúcich svetlom.The present compound is a monomer for the preparation of light degrading polymers.
PříkladExample
Roztok 2-(4-benzoylfenyl)-2-C4-(3-chlórpropanoyl)fenyljpropánu (30,7 g, 0,078 mol) v acetonitrile (50 ml) sa přidá po častiach k miešanej suspenzii octanu sodného (39,5 g,A solution of 2- (4-benzoylphenyl) -2-C4- (3-chloropropanoyl) phenyl] propane (30.7 g, 0.078 mol) in acetonitrile (50 mL) was added portionwise to a stirred suspension of sodium acetate (39.5 g,
0,4 mól) v acetonitrile (550 ml). Po miešaní 1 h pri 50 °C produkt podlá chromatografie neobsahuje východziu látku. Reakčná zmes sa neutralizuje roztokom uhličitanu sodného (8,21 g, 0,078 mol) vo vodě (70 ml) a extrahuje dietyléterom. Extrakt sa suší bezvodým síranom sodným a zahustí za vákua. Získá sa 22,7 g (82 hmot %) žltej viskóznej kvapaliny. Analytická vzorka sa získá chromatografický (silikagél L 100/400, eluent n-hexán:aceton 9:1). Elementárna analýza pre C25H22O2 (354,45) vypočítané: 84,71 hmot. % uhlíka, 6,26 hmot. % vodíka, nájdené: 84,59 hmot. % uhlíka, 6,34 hmot. % vodíka. IR CC14: 1 680 (C=O), 1 670 (C=O), 1 605 cm-1 (C-H aromatické). UV CHCl-j: 267 nm (logf= 5,83), 340 (2,49). 1H NMR (CDCl.,) : 1,75 (s, 6H,0.4 mol) in acetonitrile (550 ml). After stirring at 50 ° C for 1 h, the title product was not chromatographed. The reaction mixture was neutralized with a solution of sodium carbonate (8.21 g, 0.078 mol) in water (70 mL) and extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate and concentrated in vacuo. 22.7 g (82%) of a yellow viscous liquid are obtained. An analytical sample was obtained by chromatography (silica gel L 100/400, eluent n-hexane: acetone 9: 1). Elemental analysis for C 25 H 22 O 2 (354.45) calculated: 84.71 wt. % carbon, 6.26 wt. % hydrogen, found: 84.59 wt. % carbon, 6.34 wt. % hydrogen. IR CCl 4 : 1680 (C = O), 1670 (C = O), 1660 cm -1 (CH aromatic). UV CHCl3: 267 nm (logf = 5.83), 340 (2.49). 1 H NMR (CDCl 3): 1.75 (s, 6H,
CH3), 5,83, 5,85, 5,94, 5,96 (2xd, 1H, H-C=C trans), 6,32, 6,34, 6,49, 6,51 (2xd, 1H, H-C=C cis), 7,02, 7,12, 7,19 (m, 0,85 H, =CH-CO), 7,28 až 7,59 (m, 7H, aromatické + 0,15H, =CH-CO-),CH 3 ), 5.83, 5.85, 5.94, 5.96 (2xd, 1H, HC = C trans), 6.32, 6.34, 6.49, 6.51 (2xd, 1H, HC = C cis), 7.02, 7.12, 7.19 (m, 0.85 H, = CH-CO), 7.28-7.59 (m, 7H, aromatic + 0.15H, = CH-CO-),
7,64 až 7,93 (m, 6H, aromatické orto k C=O). Hmotnostně spektrum m/e: 354 (M+), 339, 327,7.64 to 7.93 (m, 6H, aromatic ortho to C = O). Mass Spectrum m / e: 354 (M < + > ), 339, 327,
223, 178, 105, 77.223, 178, 105, 77.
Vynález má využitie v chemickom priemysle pri príprave polymérov vyznačujúcich sa vysokou degradácioui ultrafialovým svetlom.The invention has utility in the chemical industry in the preparation of polymers characterized by high degradation by ultraviolet light.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875527A CS266111B1 (en) | 1987-07-22 | 1987-07-22 | 2-/4-benzoylphenyl/-2-/4-propenoylphenyl/propane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS875527A CS266111B1 (en) | 1987-07-22 | 1987-07-22 | 2-/4-benzoylphenyl/-2-/4-propenoylphenyl/propane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS552787A1 CS552787A1 (en) | 1989-03-14 |
| CS266111B1 true CS266111B1 (en) | 1989-11-14 |
Family
ID=5400333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS875527A CS266111B1 (en) | 1987-07-22 | 1987-07-22 | 2-/4-benzoylphenyl/-2-/4-propenoylphenyl/propane |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS266111B1 (en) |
-
1987
- 1987-07-22 CS CS875527A patent/CS266111B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS552787A1 (en) | 1989-03-14 |
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