Sodium cyclohexylsulfamate

Sulfation andSulfamation. Sulfamic acid can be regarded as an ammonia—SO. complex and has been used thus commercially, always in anhydrous systems. Sulfation of mono-, ie, primary and secondary, alcohols polyhydric alcohols unsaturated alcohols phenols and phenolethylene oxide condensation products has been performed with sulfamic acid (see Sulfonation and sulfation). The best-known appHcation of sulfamic acid for sulfamation is the preparation of sodium cyclohexylsulfamate [139-05-9] which is a synthetic sweetener (see Sweeteners). 

Sulfamation is the formation (245) of a nitrogen sulfur(VI) bond by the reaction of an amine and sulfur trioxide, or one of the many adduct forms of SO. Heating an amine with sulfamic acid is an alternative method. A practical example of sulfamation is the artificial sweetener sodium cyclohexylsulfamate [139-05-9] produced from the reaction of cyclohexylamine and sulfur trioxide (246,247) (see Sweeteners). Sulfamic acid is prepared from urea and oleum (248). Whereas sulfamation is not gready used commercially, sulfamic acid has various appHcations (see SuLFAMiC ACID AND SULFAMATES) (249—253). 

In the presence of a large excess of acid, sulfones such as diphenyl sulfone [127-63-9] (C H )2S02, can be formed (see Sulfolanes and sulfones). Sulfamation forms a —C—N—S— bond as in sodium cyclohexylsulfamate [139-03-9], C H NHSO Na, (see Sulfamic acid and sulfamates). Reviews of chlorosulfuric acid reactions are available (21,22). 

Sulfamic acid, like pyridine-SOa, can be used for preparing sulfamates, such as the widely used sweetening agent sodium cyclohexylsulfamate." ... 

Sodium cyclohexanesulfamate Sodium cyclohexyl amidosulfate Sodium cyclohexylsulfamate Sodium cyclohexyl sulfamidate. See Sodium cyclamate Sodium cyclopentane carboxylate Synonyms Cyclopentane carboxylic acid, sodium salt... 

Before a 1/1 /70 FDA ban (rescission proposed in early 1990), cyclamate noncaloric sweeteners were the major derivatives driving cycloliexylamine production. The cyclohexylsulfamic acid sodium salt (39) [139-05-9J and mote thermally stable calcium cyclohexylsulfamic acid (40) [139-06-1] salts were prepared from high purity cyclohexylamine by, among other routes, a reaction cycle with sulfamic acid. 

Cyclamate is a name for a group of compounds that include cyclamic (/V-cyclohexylsulfamic) acid, sodium cyclamate, and calcium cyclamate (Fig. 1). Audrieth and Sevda discovered this compound accidentally in 1937. It is a white crystalline powder with the molecular formula... 

Cyclamate (cyclohexylsulfamic acid and its calcium and sodium salts) were discovered in the United States in 1937. They are 30 to 80 times as sweet as sucrose and were widely used until late 1969, when it was... 

Cyclohexylsulfamic acid monosodium salt E952 sodium cyclohexanesulfamate. 

Systematic name Cyclohexylsulfamic acid, sodium salt... 

Another application of cyclohexylamine is in the manufacture of sodium and calcium cyclohexylsulfamates, used as sweeteners. Cyclohexylamine is converted with SO3 in the presence of an excess of a salt-forming tertiary amine. Subsequent reaction of the amine salt with sodium hydroxide yields sodium cyclohexylsulfa-mate (sodium cyclamate). The calcium salt is produced analogously using calcium hydroxide. 

Sodium iV-cyclohexyl sulfamate (cycliunate, 141 R = cyclohexyl) was introduced as a non-nutritive artificial sweetener in 1939. It is 30 times sweeter than sucrose, but was banned in the USA and Canada in 1970 because rats fed with large doses developed bladder cancer, although it is permitted in many other countries. Cyclohexylammonium sulfamate, an intermediate in the manufacture of non-nutritive sweeteners, may be prepared by reaction of cyclohexylamine (two to three equivalents) with chlorosulfonic acid in trichloroethene at 60-75 C the presence of the excess amine avoids an acidic medium and side reactions. A-Cyclohexylsulfamic acid has been obtained by treatment of cyclohexylamine with a mixture of sulfur trioxide and chlorosulfonic acid in trichloroethene at < 60 Cyclamate can also be manufactured by heating cyclohexylamine with sulfamic acid in xylene at 132-139 Benson and Spillane discussed the... 

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