Chlorinated paraffins chemistry

As their name implies, chlorinated paraffins are chlorinated derivatives of paraffinic hydrocarbons. They are referred to in this review as polychlorinated alkanes (PCAs) because they are produced by chlorination of n-alkane feedstocks. Commercial PCA mixtures fall into different categories C10-C13 (short), C 4-C17 (medium) and C2o-C30 (long). These mixtures are further subcategorized into their weight content of chlorine 40-50%, 50-60%, and 60-70% [1,2]. Knowledge of the environmental chemistry of PCAs is needed because the physical properties of short and medium chain mixtures are similar to those of the... 

The environmental chemistry of chlorinated paraffins was first reviewed in the Handbook of Environmental Chemistry by Zitko [4]. There have been many other reviews, especially for environmental and human exposure assessment, beginning with a report prepared for the US Environmental Protection Agency by Howard et al. [5] and more recently by Mukherjee [6], Environment Canada [2], UK Dept of the Environment [7], the World Health Organization [8], and by Tomy et al. [9], In addition to environmental chemistry aspects, the above reviews have covered the toxicity and bio accumulation of PCAs. This chapter will focus on the recent advances in knowledge of the physical properties, degradation, analysis, and environmental levels of PCAs with special emphasis on the Cio-Cu group. 

Muir DCG, Stem GA, Tomy GT (2000) Chlorinated paraffins. In Paasivirta J (ed) New types of persistent halogenated compounds, vol 3, Part K, The Handbook of Environmental Chemistry. Springer, Berlin, pp 203-236... 

Nikiforov VA (2010) Synthesis of polychloroalkanes. In de Boer J (ed) The handbook of environmental chemistry chlorinated paraffins. Springer, Heidelberg... 

The M2 plant used a water suspension method, developed in 1942 by a group under Dr. P. L. Salzberg at the Du Pont chemistry laboratories, involving micronized CC-2, chlorinated paraffin, and suspension and dispersing agents. This process, through the elimination of the toxic solvent, was simpler, safer, and more economical than the solvent process and was standardized for both the Army and Navy in mid-1943. ... 

Sulfochlorination of Paraffins. The sulfonation of paraffins using a mixture of sulfur dioxide and chlorine in the presence of light has been around since the 1930s and is known as the Reed reaction (123). This process is made possible by the use of free-radical chemistry and has had limited use in the United States. Other countries have had active research into process optimization (124,125). 

Chemistry and general properties. The main challenge in the manufacture of paraffin sulphonates is the lack of a reactive function in the paraffin (alkane) hydrophobe but this is overcome by using the Strecker reaction or a variant of it. The classical Strecker reaction (shown in Figure 4.10) uses a chloroalkane (which can be made by the reaction of a chlorinating agent with an alcohol) and sodium sulphite. 

The use of organic halogen compounds as the starting products for the synthesis of other organic chemicals is too immense a field to do more than indicate some of the commercial applications. In his book I4S) on the chemistry of petroleum derivatives, Ellis includes a chapter on the production of alcohols and esters from alkyl halides, and also one on miscellaneous reactions of halo-paraffins and cycloparaffins. The manufacture of amyl alcohols and related products from the chlorides has been well covered 14 ) 1 )-A two-step process for the synthesis of cyclopropane by chlorinating propane from natural gas and dechlorinating with zinc dust was devised in 1936 152). A critical review of syntheses from l,3-dichloro-2-butene was published in Russia in 1950 (1-54). The products obtainable from the allylic chlorides are covered in a number of articles 14If 14 157). 

Because the chlorine industry has a tradition of mutual cooperation in matters of safety and the environment, the process of improvement was soon taken to international level. In Europe the Bureau International Technique du Chlore (BIT) was established in 1954 and in 1989 renamed as Euro Chlor. 1991 Euro Chlor was expanded to combine various chlorine-related associations for derivatives, solvents and paraffins and today is an affiliate of the European Chemical Industry Council (CEFIC). In the USA, work coordinated by the Chlorine Institute and the Chlorine Chemistry Council. 

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