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Indene dimerization products

Proizvodi dimerizacije indena

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2002
0352-51390206393J.pdf (145.3Kb)
Authors
Jovanović, Jovan
Spiteller, Michael
Elling, Wilhelm
Article (Published version)
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Abstract
The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanović, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 2-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 1-(2’,3’-dihydro-1’H-inden-2’-yl)-1H-indene and 2,3,1’,3’-tetrahydro-[1,2’]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, sep...aration and isolation parameters were optimized in this study.

Ispitivana je reakcija 1H-indena u prisustvu Fridel-Kraftsovih kiselina. Kao što je i očekivano,1 smeša proizvoda je sadržala dimere, trimere i više oligomere. Među proizvodima sa dvostrukom molskom masom, u odnosu na molsku masu indena, određena je struktura četiri jedinjenja 6-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 2-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 1-(2’,3’-dihidro-1’H-inden-2’-il)-1H-indena i 2,3,1’,3’-tetrahidro-[1,2’]biindenilidena. Pokazano je da je prvo jedinjenje proizvod alkilacije indena, a da su preostala tri dobivena povezivanjem indena u položaju 2 sa indan-1-ilijum jonom, pri čemu je u slučaju trećeg i četvrtog jedinjenja došlo i do 1,2-hidridnog premeštanja. Uzimajući u obzir da su proizvodi dimerizacije indena komponente pirolitičkih ulja i interesantna jedinjenja kao modeli za NMR i MS analize i analize pomoću X-zraka, u ovom radu je optimizirano njihovo dobijanje, razdvajanje i izolovanje.
Keywords:
dimers of indene / structure elucidation / NMR spectroscopy / MS spectrometry / HPLC chromatography
Source:
Journal of the Serbian Chemical Society, 2002, 67, 6, 393-406
Publisher:
  • Serbian Chemical Society, Belgrade

ISSN: 0352-5139

WoS: 000176608800003

Scopus: 2-s2.0-0036060292
[ Google Scholar ]
7
8
Handle
https://hdl.handle.net/21.15107/rcub_technorep_449
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/449
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Jovanović, Jovan
AU  - Spiteller, Michael
AU  - Elling, Wilhelm
PY  - 2002
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/449
AB  - The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanović, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 2-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 1-(2’,3’-dihydro-1’H-inden-2’-yl)-1H-indene and 2,3,1’,3’-tetrahydro-[1,2’]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, separation and isolation parameters were optimized in this study.
AB  - Ispitivana je reakcija 1H-indena u prisustvu Fridel-Kraftsovih kiselina. Kao što je i očekivano,1 smeša proizvoda je sadržala dimere, trimere i više oligomere. Među proizvodima sa dvostrukom molskom masom, u odnosu na molsku masu indena, određena je struktura četiri jedinjenja 6-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 2-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 1-(2’,3’-dihidro-1’H-inden-2’-il)-1H-indena i 2,3,1’,3’-tetrahidro-[1,2’]biindenilidena. Pokazano je da je prvo jedinjenje proizvod alkilacije indena, a da su preostala tri dobivena povezivanjem indena u položaju 2 sa indan-1-ilijum jonom, pri čemu je u slučaju trećeg i četvrtog jedinjenja došlo i do 1,2-hidridnog premeštanja. Uzimajući u obzir da su proizvodi dimerizacije indena komponente pirolitičkih ulja i interesantna jedinjenja kao modeli za NMR i MS analize i analize pomoću X-zraka, u ovom radu je optimizirano njihovo dobijanje, razdvajanje i izolovanje.
PB  - Serbian Chemical Society, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Indene dimerization products
T1  - Proizvodi dimerizacije indena
EP  - 406
IS  - 6
SP  - 393
VL  - 67
UR  - https://hdl.handle.net/21.15107/rcub_technorep_449
ER  - 
@article{
author = "Jovanović, Jovan and Spiteller, Michael and Elling, Wilhelm",
year = "2002",
abstract = "The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanović, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 2-(2’,3’-dihydro-1’H-inden-1’-yl)-1H-indene 1-(2’,3’-dihydro-1’H-inden-2’-yl)-1H-indene and 2,3,1’,3’-tetrahydro-[1,2’]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, separation and isolation parameters were optimized in this study., Ispitivana je reakcija 1H-indena u prisustvu Fridel-Kraftsovih kiselina. Kao što je i očekivano,1 smeša proizvoda je sadržala dimere, trimere i više oligomere. Među proizvodima sa dvostrukom molskom masom, u odnosu na molsku masu indena, određena je struktura četiri jedinjenja 6-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 2-(2’,3’-dihidro-1’H-inden-1’-il)-1H-indena 1-(2’,3’-dihidro-1’H-inden-2’-il)-1H-indena i 2,3,1’,3’-tetrahidro-[1,2’]biindenilidena. Pokazano je da je prvo jedinjenje proizvod alkilacije indena, a da su preostala tri dobivena povezivanjem indena u položaju 2 sa indan-1-ilijum jonom, pri čemu je u slučaju trećeg i četvrtog jedinjenja došlo i do 1,2-hidridnog premeštanja. Uzimajući u obzir da su proizvodi dimerizacije indena komponente pirolitičkih ulja i interesantna jedinjenja kao modeli za NMR i MS analize i analize pomoću X-zraka, u ovom radu je optimizirano njihovo dobijanje, razdvajanje i izolovanje.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Indene dimerization products, Proizvodi dimerizacije indena",
pages = "406-393",
number = "6",
volume = "67",
url = "https://hdl.handle.net/21.15107/rcub_technorep_449"
}
Jovanović, J., Spiteller, M.,& Elling, W.. (2002). Indene dimerization products. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 67(6), 393-406.
https://hdl.handle.net/21.15107/rcub_technorep_449
Jovanović J, Spiteller M, Elling W. Indene dimerization products. in Journal of the Serbian Chemical Society. 2002;67(6):393-406.
https://hdl.handle.net/21.15107/rcub_technorep_449 .
Jovanović, Jovan, Spiteller, Michael, Elling, Wilhelm, "Indene dimerization products" in Journal of the Serbian Chemical Society, 67, no. 6 (2002):393-406,
https://hdl.handle.net/21.15107/rcub_technorep_449 .

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