Octane-1,8-diisocyanate

However, Dr. Rmke was successful in his attempt to synthesize octane-1,8-diisocyanate from sebacic add and sodium azide. In demonstrating his childlike curiosity, Dr. Bayer added the first few drops of the distillate to 1,4-butane diol and obtained a product which could be drawn into filaments, much like Carothers nylon. 

The Postnitrated Polyurethane Polymer of 3,6-Dinitro-3,6-Diaza-1,8-Octane Diisocyanate and... 

Table 8.9 shows the non-fuel uses of toluene. Some of the toluene goes into gasoline depending on its supply and price compared to other octane enhancers. Of the other uses of toluene about half is converted into benzene by hydrodealkylation, though this amount varies with the price difference between benzene and toluene. 2,4-Toluene diisocyanate (TDI) is a monomer for polyurethanes. Included in miscellaneous uses is 2,4,6-trinitrotoluene (TNT) as an explosive. 

Dibutyltin dilaurate (DBTDL) (M T Chem. Co.), 1,4-diaza [2,2,2.]. octane (Air Products), isocyanatoethyl methacrylate (IEM) and carbamoyl chloride of IEM (Dow Chem. Co.) and hexamethylene diisocyanate were used as supplied. Phenyl isocyanate, p-tolyl isocyanate, p-chlorophenyl Isocyanate (all Aldrich Chem. Co.), 2-ethoxyethyl acetate (Eastman Kodak Co.) and n-butanol (Mallinkrodt) were purified by distillation before use. 

All that is needed to make this reaction happen is a suitable catalyst, a substance that will encourage the first hydrogen atom to leave the polyol and move to the diisocyanate. The catalyst most frequently used is diazobicyclo[2.2.2]octane, more commonly known as DABCO. DABCO provides an initial tug on the hydrogen atom that needs to be moved. Once it gets the reaction started, DABCO has no further role and can be recovered for re-use. 

Terepthalonitrile disulfite, obtained from the corresponding hydroxamic acid (s. Synth. Meth. 23, 119), added with stirring to -octane, and rapidly heated to reflux at which time SOg-evolution has ceased -> p-phenylene diisocyanate. Y 96%. Also m-isomer in the presence of Supercel, and prepn. of 1,3,2,4-dioxathiazole 2-oxides from nitrile oxides, s. E. H. Burk and D. D. Carlos, J. Heterocyclic Chem. 7, 177 (1970). 

Uses Aviation gasoline additive octane booster in gasoline solvent for paints, gums, resins, rubber, inks, cleaners, adhesives, cosmetics, pharmaceuticals diluent, thinner in nitrocellulose lacquers thinner for perfumes, dyes alcohol denaturant process solvent adhesive solvent in plastic toys in extraction of various principles from plants mfg. of benzene, benzoic acid, benzaldehyde, toluene diisocyanate for PU resins, dyes, TNT for explosives, toluene sulfonates for detergents and dyestuffs adjuvant in resinous/polymeric food-contact coatings in paper/paperboard in contact with dry food in acrylic food pkg. in cellophane for food pkg. adjuvant for PC food-pkg. resins solvent in food-contact PPO resins in food-pkg. adhesives Regulatory FDA 21CFR 175.105, 175.320, 176.180, 177.1010, 177.1200, 177.1440,... 

Later, both the methods have been studied and compared, the addition reaction of various diisocyanates and dithiols carried out in chlorobenzene/o-dichlorobenzene solution with tri- -propylamine [102-69-2] and DABCO (1,4-diazabicyklo[2.2.2.]octane, triethylene diamine, 2,2 -diazabicyclo[2.2.2]octane, TED, BACO) [280-57-9] as catalyst (eq. 5) and interfacial condensation of... 

Isocyanato-octane 397 has been prepared by a multistep reaction from the corresponding amine. Octylamine 396 was first treated with CO2 at 1 atm in acetonitrile in the presence of triethylamine as organic base. The carbamate anion derived from the primary amine was then dehydrated with POQ3 in acetonitrile [198]. The method has been employed to prepare hexamethylene diisocyanate 373, a commercial isocyanate [198]. 

IPDI is a cycloaliphatic diisocyanate, but the two isocyanate groups are not equivalent. One is attached directly to the aliphatic ring, and the other is separated from the ring by a methylene group. Because their environments are different, the reactivities of the two groups are different and the reactivity can depend on the choice of catalyst. For instance, Ono and coworkers have shown that when IPDI is reacted with a primary hydroxyl group, the primary NCO is most reactive when the catalyst is 1,4-diazabicyclo [2.2.2] octane. The secondary NCO attached to the ring is the most reactive when dibutyl tin dilaurate is the catalyst. 

The catalytic activity of products I, II and HI, as well as of some comparison amines, was assessed by viscometric measurements. A polyether triol, Laprol 5003-2 B-lOl was combined with commercial toluene diisocyanate T 80 (Bayer AG)2 plus some water and acetone, for simulation of foam production conditions. The molar ratio of hydroxyl to isocyanate groups was 3/1. The amines tested for catalytic activity were also present they were 1,4-dimethylpiperazine (DMP), bis(2-morpholino-ethyl) ether (BMDEE) and l,4-diazabicyclo[2.2.2]octane (DABCO). The concentrations of amines were in the range 0.006 to 0.4 M. (DABCO is used in industrial production of PU foams, while DMP and BMDEE are used as co-catalysts.)... 

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