Sorbitan

Last updated
Sorbitan
Sorbitan.png
Names
IUPAC name
(3S)-2-(1,2-Dihydroxyethyl)tetrahydrofuran-3,4-diol
Other names
1,4-anhydrosorbitol
Identifiers
3D model (JSmol)
ChemSpider
  • none
ECHA InfoCard 100.032.415 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • C1C([C@@H](C(O1)C(CO)O)O)O
Properties
C6H12O5
Molar mass 164.16 g/mol
Appearancecolourless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sorbitan is a mixture of isomeric organic compounds derived from the dehydration of sorbitol and is an intermediate in the conversion of sorbitol to isosorbide. [1] Sorbitan is primarily used in the production of surfactants such as polysorbates; which are important emulsifying agents, with a total annual demand of more than 10000 tons in 2012. [2]

Contents

Synthesis

Sorbitan is produced by the dehydration of sorbitol 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) [3] with the five-membered 1,4-anhydrosorbitol form being the dominate 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. [4]

Sorbitol-Sorbitan-Isosorbid.svg

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 polysorbate 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. [5]

Polysorbate

Ethoxylated 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.

The general structure of polysorbate Polysorbate 60.png
The general structure of polysorbate

Related Research Articles

An emulsion is a mixture of two or more liquids that are normally immiscible owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Although the terms colloid and emulsion are sometimes used interchangeably, emulsion should be used when both phases, dispersed and continuous, are liquids. In an emulsion, one liquid is dispersed in the other. Examples of emulsions include vinaigrettes, homogenized milk, liquid biomolecular condensates, and some cutting fluids for metal working.

Surfactant Substance that lowers the surface tension between a liquid and another material

Surfactants are compounds that lower the surface tension between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, or dispersants.

Sulfonic acid

A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

A fabric softener is a conditioner that is typically applied to laundry during the rinse cycle in a washing machine to reduce harshness in clothes that are dried in air after machine washing. In contrast to laundry detergents, fabric softeners may be regarded as a kind of after-treatment laundry aid.

Isosorbide Chemical compound

Isosorbide is a bicyclic chemical compound from the group of diols and the oxygen-containing heterocycles, containing two fused furan rings. The starting material for isosorbide is D-sorbitol, which is obtained by catalytic hydrogenation of D-glucose, which is in turn produced by hydrolysis of starch. Isosorbide is discussed as a plant-based platform chemical from which biodegradable derivatives of various functionality can be obtained.

Polysorbate

Polysorbates are a class of emulsifiers used in some pharmaceuticals and food preparation. They are often used in cosmetics to solubilize essential oils into water-based products. Polysorbates are oily liquids derived from ethoxylated sorbitan esterified with fatty acids. Common brand names for polysorbates include Scattics, Alkest, Canarcel, and Tween.

Monoglyceride

Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.

Emulsifying wax is a cosmetic emulsifying ingredient. The ingredient name is often followed by the initials NF, indicating that it conforms to the specifications of the National Formulary.

Polysorbate 80 Nonionic surfactant and emulsifier used in food and cosmetics

Polysorbate 80 is a nonionic surfactant and emulsifier often used in foods and cosmetics. This synthetic compound is a viscous, water-soluble yellow liquid.

Polysorbate 20 is a polysorbate-type nonionic surfactant formed by the ethoxylation of sorbitan before the addition of lauric acid. Its stability and relative nontoxicity allows it to be used as a detergent and emulsifier in a number of domestic, scientific, and pharmacological applications. As the name implies the ethoxylation process leaves the molecule with 20 repeat units of polyethylene glycol; in practice these are distributed across 4 different chains, leading to a commercial product containing a range of chemical species.

Sorbitan monostearate is an ester of sorbitan and stearic acid and is sometimes referred to as a synthetic wax.

Sorbitan tristearate Chemical compound

Sorbitan tristearate is a nonionic surfactant. It is variously used as a dispersing agent, emulsifier, and stabilizer, in food and in aerosol sprays. As a food additive, it has the E number E492. Brand names for polysorbates include Alkest, Canarcel, and Span. The consistency of sorbitan tristearate is waxy; its color is light cream to tan.

Ouzo effect Phenomenon observed in drink mixing

The ouzo effect is a milky (louche) oil-in-water emulsion that is formed when water is added to ouzo and other anise-flavored liqueurs and spirits, such as pastis, rakı, arak, sambuca and absinthe. Such emulsions occur with only minimal mixing and are highly stable.

Lactylates are organic compounds that are FDA approved for use as food additives and cosmetic ingredients. These additives are non-toxic, biodegradable, and typically manufactured using biorenewable feedstocks. Owing to their safety and versatile functionality, lactylates are used in a wide variety of food and non-food applications. In the United States, the Food Chemicals Codex specifies the labeling requirements for food ingredients including lactylates. In the European Union, lactylates must be labelled in accordance with the requirements of the applicable EU regulation. Lactylates may be labelled as calcium stearoyl lactylate (CSL), sodium stearoyl lactylate (SSL), or lactylic esters of fatty acids (LEFA).

Macroemulsions are dispersed liquid-liquid, thermodynamically unstable systems with particle sizes ranging from 1 to 100 μm, which, most often, do not form spontaneously. Macroemulsions scatter light effectively and therefore appear milky, because their droplets are greater than a wavelength of light. They are part of a larger family of emulsions along with miniemulsions. As with all emulsions, one phase serves as the dispersing agent. It is often called the continuous or outer phase. The remaining phase(s) are disperse or inner phase(s), because the liquid droplets are finely distributed amongst the larger continuous phase droplets. This type of emulsion is thermodynamically unstable, but can be stabilized for a period of time with applications of kinetic energy. Surfactants are used to reduce the interfacial tension between the two phases, and induce macroemulsion stability for a useful amount of time. Emulsions can be stabilized otherwise with polymers, solid particles or proteins.

Polyelectrolytes are charged polymers capable of stabilizing colloidal emulsions through electrostatic interactions. Their effectiveness can be dependent on molecular weight, pH, solvent polarity, ionic strength, and the hydrophilic-lipophilic balance (HLB). Stabilized emulsions are useful in many industrial processes, including deflocculation, drug delivery, petroleum waste treatment, and food technology.

Ammonium carbamate Chemical compound

Ammonium carbamate is an organic compound with the formula NH4[H2NCO2] consisting of ammonium NH+
4
and carbamate H
2
NCO
2
. It is a white solid that is extremely soluble in water, less so in alcohol. Ammonium carbamate can be formed by the reaction of ammonia with carbon dioxide, and will slowly decompose to those gases at ordinary temperatures and pressures. It is an intermediary in the industrial synthesis of urea, an important fertilizer.

Sucrose esters

Sucrose esters or sucrose fatty acid esters are a group of non-naturally occurring surfactants chemically synthesized from the esterification of sucrose and fatty acids. This group of substances is remarkable for the wide range of hydrophilic-lipophilic balance (HLB) that it covers. The polar sucrose moiety serves as a hydrophilic end of the molecule, while the long fatty acid chain serves as a lipophilic end of the molecule. Due to this amphipathic property, sucrose esters act as emulsifiers; i.e., they have the ability to bind both water and oil simultaneously. Depending on the HLB value, some can be used as water-in-oil emulsifiers, and some as oil-in-water emulsifiers. Sucrose esters are used in cosmetics, food preservatives, food additives, and other products. A class of sucrose esters with highly substituted hydroxyl groups, olestra, is also used as a fat replacer in food.

Sorbitan monopalmitate (SMP) is a food additive, permitted by the EU. It is entry E495 in the E number list of permitted food additives. It is also known under the trade name Span 40.

References

  1. Rose, Marcus; Palkovits, Regina (9 January 2012). "Isosorbide as a renewable platform chemical for versatile applications--quo vadis?". ChemSusChem . 5 (1): 167–76. doi:10.1002/CSSC.201100580. ISSN   1864-5631. PMID   22213713. Wikidata   Q28256587.
  2. Kobayashi, Hirokazu; Fukuoka, Atsushi (2013). "Synthesis and utilisation of sugar compounds derived from lignocellulosic biomass". Green Chemistry . 15 (7): 1740. doi:10.1039/C3GC00060E. ISSN   1463-9262. Wikidata   Q105286575.
  3. Merck Index , 12th Edition, 8872
  4. Yamaguchi, Aritomo; Hiyoshi, Norihito; Sato, Osamu; Shirai, Masayuki (2011). "Sorbitol dehydration in high temperature liquid water". Green Chemistry . 13 (4): 873. doi:10.1039/C0GC00426J. ISSN   1463-9262. Wikidata   Q29040373.
  5. Martindale: The Complete Drug Reference. The Pharmaceutical Press. 2005.