From phosgene

Nacconate 100 A lachrymatory liquid b.p. 25l°C. Manufactured from phosgene and 2,4-diaminotoJuene. Used for preparing polyurethane foams and other elastomers by reaction with polyhydroxy compounds. Produces skin irritation and causes allergic eczema and bronchial asthma. 

Friedel-Crafts acylation pRIEDEL-CRAFTSREACTIONS] pol 11) -from phosgene PHOSGENE] pol 18)... 

Succinyl chloride [543-20-4] is obtained from phosphorous pentachloride and succinic acid, from thionyl chloride and succinic acid or anhydride (91,92), or from phosgene and succinic anhydride (93). 

In the ketone method, the central carbon atom is derived from phosgene (qv). A diarylketone is prepared from phosgene and a tertiary arylamine and then condenses with another mole of a tertiary arylamine (same or different) in the presence of phosphoms oxychloride or zinc chloride. The dye is produced directly without an oxidation step. Thus, ethyl violet [2390-59-2] Cl Basic Violet 4 (15), is prepared from 4,4 -bis(diethylamino)benzophenone with diethylaruline in the presence of phosphoms oxychloride. This reaction is very useful for the preparation of unsymmetrical dyes. Condensation of 4,4 -bis(dimethylamino)benzophenone [90-94-8] (Michler s ketone) with AJ-phenjl-l-naphthylamine gives the Victoria Blue B [2580-56-5] Cl Basic Blue 26, which is used for coloring paper and producing ballpoint pen pastes and inks. 

Carbonates ate manufactured by essentially the same method as chloroformates except that more alcohol is required in addition to longer reaction times and higher temperatures. The products are neutralized, washed, and distilled. Corrosion-resistant equipment similar to that described for the manufacture of chloroformates is requited. Diaryl carbonates are prepared from phosgene and two equivalents of the sodium phenolates or with phenols and various... 

Acid chlorides are used for the quantitative deterrnination of hydroxyl groups and for acylation of sugars. Industrial appHcations include the formation of the alkyl or aryl carbonates from phosgene (see Carbonic and chloroformic esters) and phosphate esters such as triethyl, triphenyl, tricresyl, and tritolyl phosphates from phosphoms oxychloride. 

An important example is the preparation of carbobenzoxy chloride (PhCH20C0Cl) from phosgene and benzyl alcohol. This compound is widely used for protection of amino groups during peptide synthesis (see 10-55). 

Polycarbonates are condensation polymers made from phosgene and bisphenol A. They have high impact strength and are used in glazing, helmets, and appliance casings. 

A V -Carbonyldiimidazole (CDI) is prepared in a convenient and safe procedure from phosgene and imidazole as a non-toxic crystalline compound (m.p. 116-118 °C).[5],[6] It reacts almost quantitatively at room temperature or by short and moderate heating with an equimolar quantity of a carboxylic acid in tetrahydrofuran, chloroform, or similar inert solvents within a few minutes to give the corresponding carboxylic acid imidazolide, which is formed under release of carbon dioxide, together with one equivalent of readily separable and recyclable imidazole.Thus, this reaction leads under very mild conditions to the activation of a carboxylic acid appropriate for transacylation onto a nucleophile with an alcohol to an ester, with an amino compound to an amide or peptide, etc. 

In their literature review, Diller and Zante (1982) also identified nonlethal effects from phosgene exposure (lethal effects are described in Section 2.1). Nonlethal information synthesized from this review is presented in Table 1-4. From the above data and from animal data for initial lung damage, Diller and Zante (1982) synthesized information for nonlethal effects of phosgene in humans (Table 1-5). 

Thus, partial protection from phosgene-induced lethality was obtained by the phosgene pretreatment. TABLE 1-6 Acute Lethality of Phosgene in Mice ... 

Time scaling Cnxt=k where n=l. Haber s Law (Cxt=k) has been shown to be valid for phosgene within certain limits (EPA 1986). Haber s Law was originally derived from phosgene data (Haber 1924). Reported 30-min data point used to determine the 30-min AEGL value. AEGL-3 values for 1-, 4-, and 8-h were based on extrapolation from the 30 min value. The 10-min value was based on a reported 10-min data point. Data adequacy The AEGL-3 values are based on a well-conducted study in rats and the database is rich. 

First of all, DMC is a nontoxic compound since the middle 1980s, in fact, it has not been produced from phosgene, but by catalytic oxidative carbonylation of methanol with oxygen through a process developed by Enichem (Italy) and UBE Industries (Japan) (Scheme 4.3) ... 

In addition to improving procedural safety, this method of producing DMC avoids contamination from phosgene, and eliminates the need to dispose of by-product inorganic salts. 

Methyl isocyanate is a very dangerous chemical. It was responsible for the deaths of over 2,500 people, perhaps as many as 10,000 people, in the worst industrial accident ever, that of the carbamate insecticide plant in Bhopal, India on December 3, 1984. It is a very toxic chemical. This tragedy is discussed in more detail in Chapter 25. Methyl isocyanate can be made from phosgene and methylamine, which would circumvent use of the isocyanate. Phosgene is made from chlorine and carbon monoxide, but it is also very toxic and dangerous. 

The conformations of the 2-oxo-tetrahydro-l,3-oxazines obtained from phosgene and the isomeric 3-amino-2,3-diphenylpropanols were used by Fodor et al. as an ingenious criterion for the configurational determination of the aminopropanols.13,14 The erythro form yielded an oxazinone that showed optical activity 4-8 times stronger than that from the threo form. 

Diphenyl carbonate is an important intermediate in the production of bisphenol-A-polycarbonate (BPA-PC). The technology shift from phosgene to DPC to produce BPA-PC on a commercial scale also allows the number of applications of this type of polymer to be increased for example, high-performance BPA-PCs utilized for information storage (e.g., DVDs) are prepared from high-purity DPC. The chemical route to this DPC brand is based on a two-step reaction, namely transesterification followed by disproportionation (Equations 7.4 and 7.5). 

Isocyanide dichlorides, formally imines derived from phosgene, react in a manner similar to that of phosgene (above) except that 2-amino-l,3,4-oxadiazole derivatives, instead of oxadiazolin-5-ones, are produced (Scheme 15) (71CC1223,81AP193,73CHE1216). 

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