Benzyl chloride, effect

Benzyl chloride is a severely irritating Hquid and causes damage to the eyes, skin, and respiratory tract including pulmonary edema. Other possible effects of overexposure to benzyl chloride are CNS depression, Hver, and heart damage. Table 3 Hsts some exposure limits. 

Other toxicological effects that may be associated with exposure to benzyl chloride based on animal studies are skin sensitization and developmental embryo and/or fetal toxicity. A 1980 OSHA regulation has estabhshed a national occupational exposure limit for benzyl chloride of 5 mg/m (1 ppm). Concentrations of 160 mg/m (32 ppm) in air cause severe irritation of the eyes and respiratory tract (68). 

The work of Hyatt on cyclotriveratrylene—derived octopus molecules contrasts with this. Of course, these species have the advantage of ligand directionality absent in the benzene-derived octopus molecules. Except for the shortest-armed of the species (i.e., n = 1), all of the complexing agents (i.e., n = 2—4) were capable of complexing alkali metal cations. Synthesis of these species was accomplished as indicated below in Eq. (7.7). These variations of the original octopus molecules were also shown to catalyze the reaction between benzyl chloride and potassium acetate in acetonitrile solution and to effect the Wittig reaction between benzaldehyde and benzyltriphenylphos-phonium chloride. 

An attempt to prepare phenylacetonitrile by the effect of sodium cyanide on benzyl chloride in a methanol medium led to the explosion of the reactor. This was explained by insufficient cooling of the medium. 

Quaternary ammonium salts (Cio to Cig alkyl benzyl dimethyl ammonium chloride) added in 40 ppm and 2% of sodium chloride effect an increase in the strength of the cement rock and the adhesion properties by 50% to 80% [1769]. 

Hydrocarbonylation. The hydrocarbonylation reaction can be applied to the synthesis of a-arylpropanoic acids of the NSAIDS type.239 For this synthesis to be effective, selective carbonylation of the more-substituted sp2 carbon is required. Although many carbonylation conditions are unselective, PdCl2(PPh3)2 with /2-toluenesulfonic acid and LiCl achieves excellent selectivity. The selectivity is thought to involve the formation of a benzylic chloride intermediate. 

For carbon-carbon bond-formation purposes, S 2 nucleophilic substitutions are frequently used. Simple S 2 nucleophilic substitution reactions are generally slower in aqueous conditions than in aprotic organic solvents. This has been attributed to the solvation of nucleophiles in water. As previously mentioned in Section 5.2, Breslow and co-workers have found that cosolvents such as ethanol increase the solubility of hydrophobic molecules in water and provide interesting results for nucleophilic substitutions (Scheme 6.1). In alkylations of phenoxide ions by benzylic chlorides, S/y2 substitutions can occur both at the phenoxide oxygen and at the ortho and para positions of the ring. In fact, carbon alkylation occurs in water but not in nonpolar organic solvents and it is observed only when the phenoxide has at least one methyl substituent ortho, meta, or para). The effects of phenol substituents and of cosolvents on the rates of the competing alkylation processes... 

The effect of the size of the reaction vessel on the rate of M W-heated SN2 reaction of 4-cyanophenoxide ion 1 and benzyl chloride 2 in methanol (Scheme 4.2) was investigated by reacting identical amounts of reagents in Teflon vessels of different sizes. 

Knochel et al. (1977a) have studied the effect of the structure of the ligand on its ability to catalyse the reaction between solid metal acetates and benzyl chloride dissolved in acetonitrile. Approximate half-lives for the reactions are given in Table 29. For crown ethers, the reactivity sequence decreases in the... 

Phenol (508) is found to be produced continuously from benzene (507) by aerial oxidation in aqueous sulfuric acid when a Cu(I)/Cu(II) redox couple is used as a mediator (Scheme 176) [581]. The Cu(I)-mediated electroreduction of oxygen in the presence of chloride is found to be effective for toluene oxidation, leading to benzaldehyde and benzyl chloride [582]. Recently, benzene has also been oxidized... 

Pierce, J.H. Wolfe, N.L. "Effects of Sediment Sorption on Abiotic Hydrolyses II. 4-(p-chlorophenoxy) butyl bromide and Benzyl Chloride", paper in preparation, 1984. 

Solid-phase microextraction (SPME) is effectively a miniamrised version of SPE. Instead of using a packed cartridge, a rod is typically used, which is coated with the stationary phase. This is dipped into a solution of the analyte and allowed to extract for a pre-determined period of time. After this incubation period, the rod is removed from the solution and may be inserted directly into the injection system of the GC or HPLC. All of these operations can be automated on an autosampler. Clearly, the success of this technique depends intimately on the affinity of the analyte for the stationary phase. Frost, Hussain and Raghani [34] used SPME with GC-FID to measure benzyl chloride and chloroethylmethyl ether (amongst other process impurities) in pharmaceutical preparations. 

We synthesized 8 by the one-step reaction of [Ph4(Tl -C4CO)]Ru(CO)3 with benzyl chloride. In contrast to previous alcohol racemization catalysts, 8 was stable in the air during racemization [30]. The racemization was performed even under 1 atm of molecular oxygen. Thus, alcohol DKR was for the first time possible with 8 in the air at room temperature (R)-l-phenylethyl acetate (99% yield, greater than 99%e.e.) was obtained from 1-phenylethanol by using 4mol% of 8, CALB and isopropenyl acetate in the presence of potassium phosphate (Scheme 1.22). This catalyst system was effective for both benzylic and aliphatic alcohols. The synthetic method for 8 was applied to the preparation of a polymer-bound derivative (9). Hydroxymethyl polystyrene was reacted with 4-(chloromethyl)benzoyl chloride to... 

Benzyl chloride caused genetic mutations and chromosome-damaging effects in a wide variety of in vitro assays it was not mutagenic in vivo in the mouse micronucleus assay. ... 

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