Carbon-disulfide

Chemical Names Carbon Disulfide, Carbon Bisulfide Common Names Carbon Disulfide, Carbon Bisulfide Formula CS2 

Grades Commercial or Technical, and USP Important Physical and Chemical Properties 

Odor Almost odorless when pure the commercial grade has a strong disagreeable odor, due to presence of sulfur compounds. Specific Gravity at 20° C/4° C (68° F/39° F) (Water = 1) 1.263 Vapor Density (Air = 1) 2.63 Boiling Point (760 mm) 46.3° C (115° F) 

Explosive Limits (per cent by volume in air) 1 to 50 Ignition Temperature 100° C (212° F) 

Corrosive Commercial grade slightly corrosive to some metals due to impurities. 

Manufacture. Up to fairly recently carbon disulfide was almost exclusively manufactured by the reaction of carbon, in particular low ash charcoal, with sulfur at high temperatures in brick-lined retorts or in electrical furnaces (electrochemical process). In the USA, Canada, Japan and Europe methane or natural gas is currently largely used as the carbon source and this is reacted with sulfur at ca. 650°C  

Carbon disulfide is purified by distillation. The hydrogen sulfide byproduct is processed to sulfur in Claus plants. 

3 lO t of carbon disulfide was produced worldwide in I99I, mainly from methane and sulfur. 

Applications Carbon disulfide is mainly used in the viscose industry for fiber production. Smaller quantities are utilized in the manufacture of cellophane from viscose or as a starting material in the production of carbon tetrachloride. In addition carbon disulfide is used in the production of vulcanization accelerators, flotation agents, corrosion inhibitors, pesticides and intermediates for pharmaceuticals. 

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CARBON DISULFIDE 195-448 1.8618E402 -7 6S92E4 03 7 904SE-02 -3 18886701 -3.51I9E-0S... 

This measurement provides a definition of the bitumen content in bitumen materials as the portion soluble in carbon disulfide (in France, in trichloroethylene, carbon tetrachloride or tetrachloroethylene). The method is defined by AFNOR NF T 66-012 or IP 47, or ASTM D 4 (the latter is not equivalent to the others). 

Without carbon, the basis for life would be impossible. While it has been thought that silicon might take the place of carbon in forming a host of similar compounds, it is now not possible to form stable compounds with very long chains of silicon atoms. The atmosphere of Mars contains 96.2% CO2. Some of the most important compounds of carbon are carbon dioxide (CO2), carbon monoxide (CO), carbon disulfide (CS2), chloroform (CHCb), carbon tetrachloride (CCk), methane (CHr), ethylene (C2H4), acetylene (C2H2), benzene (CeHe), acetic acid (CHsCOOH), and their derivatives. 

It is insoluble in water, but soluble in carbon disulfide. It takes fire spontaneously in air, burning to the pentoxide. 

Sulfur is pale yellow, odorless, brittle solid, which is insoluble in water but soluble in carbon disulfide. In every state, whether gas, liquid or solid, elemental sulfur occurs in more than one allotropic form or modification these present a confusing multitude of forms whose relations are not yet fully understood. 

Organic compounds containing sulfur are very important. Calcium sulfur, ammonium sulfate, carbon disulfide, sulfur dioxide, and hydrogen sulfide are but a few of the many important compounds of sulfur. 

Carbon disulfide, hydrogen sulfide, and sulfur dioxide should be handled carefully. Hydrogen sulfide in small concentrations can be metabolized, but in higher concentrations it quickly can cause death by respiratory paralysis. 

Iodine is a bluish-black, lustrous solid, volatizing at ordinary temperatures into a blue-violet gas with an irritating odor it forms compounds with many elements, but is less active than the other halogens, which displace it from iodides. Iodine exhibits some metallic-like properties. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide to form beautiful purple solutions. It is only slightly soluble in water. 

Halogenation of 2-aminothiazole and derivatives has been reported under a wide variety of experimental conditions in water (161, 405. 406) in aqueous acids (16. 172, 407, 408) in solvents such as chloroform (27. 172), carbon disulfide (162, 166. 320. 409). benzene (165), acetic acid (410-413, 1580). or hydrochloric acid (414) or in 20% sulfuric acid (415-417). 

N-(2-thiazolyl)dithiocarbamates are prepared by the action of carbon disulfide on 2-aminothiazoles (see Section III.3.C and Ref. 505). When refluxed with secondary amines these heterocyclic dithiocarbamates yield l,T-dialkyl-3-(2-thiazoIyI)thioureas (261) (491). 

Recently, it has been reported that l,3-dithiole-2-thione (12) reacts with primary amine to give the corresponding thiourea and A-4-thia2oline-2-thione (Scheme 5) (14). 5-Methylenethiazolidine-2-thione (13) obtained from the reaction of propargyl amine and carbon disulfide... 

The thiazole ring can be obtained directly by other methods, but they have limited application. An example is the synthesis of Cook and Heilbron using a-aminonitriles or a-aminoamides and carbon disulfide (or thioacid derivatives) as reactants of type II. 

This type of synthesis, which was investigated by Cook and Heilbron (323) and Takahashi (393, 394) between 1947 and 1953, gives 5-aminothiazoles variously substituted in the 2-position by reacting an aminonitrile with salts and esters of dithioacids, carbon disulfide, carbon oxysulfide, and isothiocyanates under exceptionally mild conditions. 

Carbon disulfide readily reacts with a-aminonitriles giving 2-mercapto-5-aminothiazoles (213), (271, 293) which can be converted to 5-aminothiazoles unsubstituted in the 2-position (Scheme 110 and Table II-34a). If this reaction is carried out in the presence of benzyl chloride in phosphorus tribromide, a 2-S-substituted thiazole derivative (214) is obtained in quantitative yield (Scheme 111), with R = hydrogen or phenyl (68, 304). 

TABLE II-34a. 2-MERCAPTO-5-AMINOTH1AZOLE DERIVATJVES FROM a-AMINONITRUJES and carbon disulfide... 

When benzaldehyde or its substituted derivatives are added to carbon disulfide and a-aminonitrile, the corresponding 2-mercapto-5-(p-R-benzylideneamino)thiazoles (215), R = hydrogen atom or a propenyl or phenyl group and Ar = aryl, are obtained (Scheme 112) (393, 442, 694). Yields ranged from 40 to 60% (Table II-34b). 

Reactions were carried out by condensing a-aminonitriles [NCCHiRiiNHJ with carbon disulfide in the presence of aldehydes (R CHO) or ketones [Pg.287]

Methyiaminoacetonitrile (216) reacts with carbon disulfide in the presence of acetic anhydride with ethyl acetate as solvent to give 2-thio-3-methyl-A-4-thiazoline in 74% yield (Scheme 113a) (326). If the reaction is carried out using benzaldehyde in place of acetic anhydride, the corresponding 5-benzylideneamino derivative of 217 is obtained in 70% yield. 

Another example of condensation with carbon disulfide is shown in (Scheme 113b) (774). 

Although not fully characterized, 2-carbethoxy-4-hydroxythiazole (230a), R, = C02Et, R2 = H, apparently results from the reaction of chloroacetonitrile with ethyl thiooxamate (2), Ri = C02Et (417). a-Chlorothioacids (232) condensed with thiobenzamide in the presence of carbon disulfide (542) yield the corresponding 2-phenyl-4-hydroxy-thiazole (234). The same product was obtained from 233 (Scheme 121). 

Ethylisocyanoacetate with carbon disulfide leads to the 1,3-thiazole in 49% yield (Scheme 147) (778). 

When a dilute solution of 6 phenylhexanoyl chloride in carbon disulfide was slowly added (over a period of eight days ) to a suspension of aluminum chloride in the same solvent it yielded a product A (C12H14O) in 67% yield Oxidation of A gave benzene 1 2 dicarboxyhc acid... 

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