Natural and Synthetic Rubber. II. Reduction of Isoprene by Na-Nh3

1929 ◽  
Vol 2 (3) ◽  
pp. 452-452
Author(s):  
Thomas Midgley ◽  
Albert L. Henne

Abstract The reduction of isoprene by sodium in liquid ammonia was attempted to determine: (1) whether reduction would take place in preference to polymerization and (2) the location of the added hydrogen. Isoprene was added to sodium dissolved in liquid ammonia and a 60% yield of 2-methyl-2-butene resulted. No other volatile hydrocarbon was found. High molecular weight hydrocarbons were formed but were not investigated. It is thus shown: (1) that the predominant reaction proceeds in accordance with the equation C5C8+2Na+2NH3=C5C10+2NaNH2 and (2) that hydrogen adds to isoprene in the 1,4-position, in agreement with Thiele's theory. The hydrogen addition is similar to the bromination of isoprene at low temperature. If properly conducted the latter reaction stops after 2 atoms of bromine have been added to 1 molecule of isoprene; the resulting compound, 1,4-dibromo-2-methyl-2-butene, is characterized b the inactivity of its double bond toward bromine. Similarly, 2-methyl-2-butene obtained by reduction of isoprene is not reduced to isopentane by an excess of Na—NH3 reagent.

2020 ◽  
pp. 77-78

The use of ultra-high molecular weight polyethylene (UHMW PE) for the manufacture of various parts, in particular cuffs for hydraulic drives, is proposed. The properties and advantages of UHMW PE in comparison with other polyethylene materials are considered. Keywords ultra-high molecular weight polyethylene, hydraulic pump, hydraulic motor, hydraulic control valve, hydraulic oil, low temperature. [email protected]


1930 ◽  
Vol 3 (3) ◽  
pp. 483-484
Author(s):  
Thomas Midgley ◽  
Albert L. Henne

Abstract Isoprene has been ethylated; 4-methyl-4-octene was formed exclusively. The structure of this nonene is in agreement with the usual behavior of a conjugated double bond system. This type of addition is further evidence in favor of the hypothesis which regards the polymerization of isoprene to synthetic rubber as the formation of long chains of isoprene units linked together- by ordinary valences in the 1,4-position.


Polymer ◽  
1996 ◽  
Vol 37 (15) ◽  
pp. 3411-3417 ◽  
Author(s):  
P.N. Adams ◽  
P.J. Laughlin ◽  
A.P. Monkman ◽  
A.M. Kenwright

1945 ◽  
Vol 18 (4) ◽  
pp. 874-876
Author(s):  
Richard F. Robey ◽  
Herbert K. Wiese

Abstract Peroxides are found in synthetic rubbers either as the result of attack by oxygen, usually from the air, or as a residue from polymerization operations employing peroxide catalysts. Because of possible detrimental effects of active oxygen on the properties of the rubber, a method of quantitative determination is needed. The concentration of peroxides in substances of lower molecular weight may be determined with ferrous thiocyanate reagent, either titrimetrically as recommended by Yule and Wilson or colorimetrically as by Young, Vogt, and Nieuwland. Unfortunately, many highly polymeric substances are not soluble in the acetone and methanol solutions employed in these procedures. This is also the case with hydrocarbon monomers, such as butadiene, containing appreciable concentrations of soluble high molecular weight polymers. Bolland, Sundralingam, Sutton and Tristram recommended benzene as a solvent for natural rubber samples and the reagent made up in methanol. However, most synthetic rubbers are not readily soluble even in this combination. The following procedure employs the ferrous thiocyanate reagent in combination with a solvent capable of maintaining considerable concentrations of synthetic rubber in solution. The solvent comprises essentially 20 per cent ethanol in chloroform.


1948 ◽  
Vol 21 (4) ◽  
pp. 864-876
Author(s):  
John B. Gregory ◽  
Irving Pockel ◽  
John F. Stiff

Abstract A new method for measuring the flexibility of rubber has been described. The method consists essentially in determining the stress-strain curve obtained by loading and unloading a loop formed from a one-inch by six-inch strip cut from a test slab. A coefficient of flexibility independent of the thickness of the sample and, in addition, information on per cent resilience were obtained. By the use of the method described, the behavior of various natural and synthetic rubber gas mask facepiece compounds was studied during one month to three months' exposure at various temperatures down to −20° F. Progressive stiffening probably due to crystallization was found for natural rubber, GR-I, and GR-M compounds at low temperatures. No tendency to crystallize was noted for the GR-S compound. Of the crystallizable polymers GR-I was the most resistant, and GR-M the least resistant to stiffening during low temperature storage. It is of course evident that different polymers have inherently different degrees of resistance to low temperatures. Disregarding these inherent differences the work reported indicates that the resistance of elastomer compounds to stiffening during prolonged low temperature storage is favored by the following: 1. Use of interpolymers made from monomer mixtures having a relatively large proportion of each component, thus obtaining mutual intereference with crystallization. 2. Use of a “tight” cure which probably so impedes the movement of the polymer chains as to make crystallization difficult.


2016 ◽  
Vol 7 (3) ◽  
pp. 1773-1778 ◽  
Author(s):  
Inbal Berkovich ◽  
Sudheendran Mavila ◽  
Olga Iliashevsky ◽  
Sebastian Kozuch ◽  
N. Gabriel Lemcoff

High molecular weight polybutadienes and rhodium complexes were used to produce single chain organometallic nanoparticles. A relationship was found between the cis double bond content of the polymer and metal binding kinetics.


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