Methyl indan

After reaction, any solid residue was filtered off and the liquid product was separated by distillation into a bottoms product and a distillate that included unreacted Tetralin and low-boiling products from both the coal and the Tetralin. As tetralin breaks down under dissolution conditions to form mainly the tetralin isomer 1-methyl indan, naphthalene and alkyl benzenes (4) it was assumed that no compound with a higher boiling point than naphthalene was formed from the solvent, and the distillation to recover solvent was therefore continued until naphthalene stopped subliming. Some residual naphthalene remained in the bottoms product its mass, as determined from nmr and elemental analysis, was subtracted from the mass of bottoms product recovered and included in the amount of distillate recovered. It was assumed that all naphthalene present came from the Tetralin, not the coal. However, as the amount of tetralin reacted was 10 times the amount of coal this assumption appears reasonable. 

Analysis Techniques. The contents of the major breakdown products of xetralin (naphthalene and 1-methyl indan) present in the distillate were determined by gas-liquid chromatography using a Hewlett Packard Series 5750 Research Chromatograph with a 62m x 0.5mm diameter glass capillary SCOT column coated with nonpolar SE 30 liquid phase (see Reference (4 ) for details). 

Tetralin has been shown to undergo thermal dehydrogenation to naphthalene and rearrangement to methyl indan in either the absence or presence of free radical acceptors [ 1, 2]. The presence of free radical acceptors usually accelerates the rearrangement reaction. Even with alkylated Tetralins>... 

The basic reactions of Tetralin and derivatives have been extended to the use of 1-13C labels and 1,2-dihydronaphthalene, with and without a source of free radicals. The studies with Tetralin were monitored equally well with C-NMR and GLC techniques. The rate constant for the conversion of Tatralin to methyl indan in the presence of dibenzyl at 450°C was 6.4 x 10 min i which is consistent with that previously reported [2]. 

The most significant observation by NMR is the redistribution of the label in the methyl indan isomer. 

Concentration of 2-methyl indan and 2- C-1-methyl indan were very low. 

Dihydronaphthalene (DHN) is frequently assumed to be an intermediate in hydrogen transfer reactions. While this appears reasonable, efforts to detect and/or measure this intermediate have never been very successful. Assuming that DHN is present, we have briefly explored its role in hydrogen transfer and methyl indan formation. 

DHN. Apparently DHN both thermally dehyrogenates to naphthalene and disproportionates to Tetralin and naphthalene. In all of the runs, there was a sizable amount of hydrogen released when the reactors were opened. When DHN was heated at 450°C for either 15 or 180 minutes, the ratio of naphthalene to etralin was 1.8. Increased methyl indan formation occurred with time. With the introduction of dibenzyl, the anticipated [2] increased isomerization of T etralin to methyl indan occurred. These results suggest that the rearrangement of hydroaromatics does not proceed through the dihydro-... 

Since the Tetralin studies showed that isomerization yielded predominantly the 1-methyl indan isomer and that the... 

FIGURE 9. MM2-85 calculated torsional potential surface for the two-angle driver of the side chain of (S)-4-hydroxy-2-[(dimethylamino)methyl]indan 70. Reproduced with permission from Reference 108... 

Figure 2.7 contains plots of repetitive injection GC/MS chromatographic peak areas (integrated total ion current) as a function of sample temperature for benzene and styrene as well as selected products representing alkyl aromatics (ethyl benzene), indanes (methyl indane) and indenes (indene) evolved from PS-catalyst samples. The plots show that benzene is by far the most abundant volatile product. All of the PS-catalyst samples produce alkyl benzenes and indanes, however samples containing HZSM-5 catalyst generate significantly lower relative yields of these products. 

Figure 2.8 Species-specific evolution profiles for methyl indane (open circles) and naphthalene (open squares) derived from a PS-Zr02/S04 sample. (Reproduced by permission of John Wiley Sons, Ltd)...

The results of supercritical water reaction of quinoline in the presence of Fe2O3 conducted by Ogunsola (4) allowed her to develop a reaction sequence depicted in Figure 3. Generation of aniline type products has been regarded by Houser et al (24) as due to pronounced preference for 1-2 bond rupture. The presence of naphthalene 2- methyl also suggests that naphthalene is an intermediate product that may arise from methyl-indane interaction. 

R1 = CH, R2 = H Raney-Ni Athanol/Wasser — - 1 -Hydroxy -2 -methyl-indan — i... 

Piperidin Ra-Co 1) Enamin-Bildung 140-160° in 100 60 3-(Piperidino-methyl)-indan 52 1... 

A number of acrylonitrile - Cinchona alkaloid copolymers have been prepared in which the vinyl group of the alkaloid has been modified, and the ability of these copolymers to act as asymmetric catalysts in the Michael addition of methyl vinyl ketone to methyl indan-l-one-2-carboxylate has been studied.In twelve cases, good enantiomeric yields, ranging from 41 to 56% ee, were obtained. 

Copyrolysis (ca. 650 °C) of tetrafluorophthalic anhydride with tetrafluoro-ethylene or hexafluoropropene provides a route to perfluorobenzocyclobutenes (50 X = F, Y = F or CFs) (some perfluoroindane is also formed in the former reaction) and an analogous reaction occurs with phthalic anhydride itself [to give (50 X = H, Y = F)]. Perfluoro(methylnaphthalenes) are the main products from octafluoronaphthalene and polytetrafluoroethylene at elevated temperatures, but the reaction of octafluoronaphthalene with potassium fluoride at ca. 500 °C gives a mixture containing perfluoro(methylnaphthalenes, indane, and methyl-indanes). Such reactions are believed to involve difluorocarbene, and some... 

Representative procedure synthesis of (S)-(l-methyl-indan-l-yl)-acetonitril ... 

Oxidative rearrangements, via oxythallation, have been improved in yield and selectivity by the use of thallium(iii) nitrate supported on clay rather than in methanolic solution. Thus, cyclohexene gave an 85% yield of dimethoxymethyl-cyclopentane while 1-tetralone, which normally gives a complex mixture of products, gave a 1 1 mixture of methyl indane-l-carboxylate and 2-methoxytetralone. An efficient, large-scale procedure for the direct cis-dihydroxylation of olefins has been reported. The oxidant is t-butyl hydroperoxide and the catalyst osmium tetroxide, with the reaction conducted under alkaline conditions (E%N OH ), so facilitating a rapid turnover of catalyst via enhanced hydrolysis of the osmate esters. The method appears to be more advantageous for the more substituted olefins than the Hofmann and Miles procedure. 

The need for HTPs or HTPBs is often for chemical (e.g., preventing of swelling or oxidation) and mechanical performance. For example, in the petroleum industry dual-layer hollow fiber membranes are used for separation of H2/CO2 and CO2/CH4 gases. These are prepared from solutions of 1 1 PIB/PI blend (e.g. poly[2,2 -(l,3-phenylene)-5,5 -bibenzimidazole] and poly[3,3 4,4 -benzophenone-icira-carboxylic-df-anhydride-co-5(6)-amino-l-(4 -amino-phenyl-l,3-/n-methyl-indane)]).i i The spun hollow fibers are coated by a solution of silicone rubber. The membranes had the desired microstructure. Membrane selectivity of 11.11 and 41.81 was obtained for H2/ CO2 and CO2/CH4, respectively. Furthermore, the new membranes showed good resistance toward COj-induced plasticization. Camacho-Zuniga et al. 

Azeotropic water entrainment. 2-Methyl-2,3 -oxobutylcyclopentane-l,3-dione refluxed in benzene under a modified Dean-Stark water separator in the presence of p-toluenesulfonic acid, which is added in 2 portions, until after 5 hrs. the theoretical amount of water has been collected 5,6,7,8-tetrahydro-8-methyl-indane-l,5-dione. Y 83%. Limitation s. C. B. C. Boyce and J. S. Whitehurst, Soc. 1959, 2022. 

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