Sorbitan is a mixture of

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s derived from the

dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...

sorbitol Sorbitol (), less commonly known as glucitol (), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alco ...

and is an intermediate in the conversion of sorbitol to isosorbide. Sorbitan is primarily used in the production of

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

s such as

polysorbate Polysorbates are a class of emulsifiers used in some pharmaceuticals and food preparation. They are commonly used in oral and topical pharmaceutical dosage forms. They are also often used in cosmetics to solubilize essential oils into water-based ...

s; which are important emulsifying agents, with a total annual demand of more than 10,000 tons in 2012. Sorbitan and Sorbitol esters are an uncommon allergen.

Synthesis

Sorbitan is produced by the dehydration of

and is an intermediate in the conversion of sorbitol to isosorbide. The dehydration reaction usually produces sorbitan as a mixture of five- and six-membered cyclic ethers (1,4-anhydrosorbitol, 1,5-anhydrosorbitol and 1,4,3,6-dianhydrosorbitol) with the five-membered 1,4-anhydrosorbitol form being the dominant product. The rate of formation of sorbitan is typically greater than that of isosorbide, which allows it to be produced selectively, providing the reaction conditions are carefully controlled. The dehydration reaction has been shown to work even in the presence of excess water. Sorbitol-Sorbitan-Isosorbid

Surfactant derivatives

Esters

Sorbitan esters (also known as Spans) are nonionic surfactants that are used as emulsifying agents in the preparation of emulsions, creams, and ointments for pharmaceutical and cosmetic use. When used alone they produce stable water-in-oil emulsions but they are frequently used with a

in varying proportions to produce water-in-oil or oil-in-water emulsions or creams with a variety of different textures and consistencies. Sorbitan esters are also used as emulsifiers and stabilisers in food. File:Sorbitan monostearate.svg, Sorbitan monostearate File:Sorbitan_tristearate.png, Sorbitan tristearate File:Sorbitan_monolaurate.svg, Sorbitan monolaurate

Polysorbate

Ethoxylated In organic chemistry, ethoxylation is a chemical reaction in which ethylene oxide () addition reaction, adds to a Substrate (chemistry), substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrat ...

sorbitan esters are known as polysorbates (trade name: Tweens). They are an important class of emulsifiers used in a variety of settings, including pharmaceuticals and food. Polysorbate 60

References

{{Reflist Tetrahydrofurans Non-ionic surfactants Monosaccharide derivatives