Isosorbide

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Isosorbide
Isosorbide.svg
Names
Preferred IUPAC name
(3R,3aR,6S,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diol
Other names
D-Isosorbide; 1,4:3,6-Dianhydro-D-sorbitol; 1,4-Dianhydrosorbitol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.449 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1 Yes check.svgY
    Key: KLDXJTOLSGUMSJ-JGWLITMVSA-N Yes check.svgY
  • InChI=1/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
    Key: KLDXJTOLSGUMSJ-JGWLITMVBP
  • O[C@@H]1[C@H]2OC[C@@H](O)[C@H]2OC1
Properties
C6H10O4
Molar mass 146.142 g·mol−1
AppearanceHighly hygroscopic white flakes
Density 1.30 at 25 °C
Melting point 62.5 to 63 °C (144.5 to 145.4 °F; 335.6 to 336.1 K)
Boiling point 160 °C (320 °F; 433 K) at 10 mmHg
in water (>850 g/L), alcohols and ketones
Pharmacology
None
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Isosorbide
Clinical data
Trade names Ismotic, Isobide, others
License data
Identifiers
CompTox Dashboard (EPA)
ECHA InfoCard 100.010.449 OOjs UI icon edit-ltr-progressive.svg

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.

In 2022, it was the 119th most commonly prescribed medication in the United States, with more than 5 million prescriptions. [1] [2]

Uses

Isosorbide

Because of its pronounced hygroscopicity, isosorbide is used as a humectant and in medicine as an osmotic diuretic for the treatment of hydrocephalus and acute angle-closure glaucoma. [3] [4] The two secondary hydroxy groups make isosorbide a versatile platform chemical accessible from renewable resources. As a diol, isosorbide can be mono- or biderivatized using the standard methods of organic chemistry, such as nitration, esterification, etherification, tosylation, etc., and converted into compounds with interesting properties or into monomeric units for novel polymers. [5]

Reaktionen von Isosorbid Isosorbide reactions.svg
Reaktionen von Isosorbid

Isosorbide nitrates

By nitration of isosorbide with concentrated nitric acid, 2,5-isosorbide dinitrate (ISDN) can be obtained. 2,5-isosorbide dinitrate is suitable (just like its major metabolite 5-isosorbide mononitrate, ISMN [6] ) for the treatment of angina pectoris due to its vasodilator effect. [7]

Isosorbide esters

Esterification of isosorbide with fatty acids gives access to isosorbide monoesters, which are useful as detergents in household cleaners, dishwashing detergents, and cosmetic preparations, because of their properties as surfactant. [8] The likewise readily available isosorbide diesters [9] are used as dispersants for pigments, preservatives, polymer stabilizers, as emulsifiers for cosmetics and as plasticizers for vinyl polymers (in particular polyvinyl chloride, PVC). Isosorbide dioctanoate [10] is a diester of isosorbide and octanoic acid (obtained from palm oil, for example) and therefore made entirely from bio-based building blocks and has been used as Polysorb ID 37 by Roquette Frères for some time as a particularly non-toxic product. [11]

Isosorbide ethers

Isosorbide ethers (and in particular the simplest representative, 2,5-dimethylisosorbide, abbreviated DMI), are increasingly used as a renewable solvent for cosmetic and pharmaceutical preparations, [12] as an electrolyte additive for lithium-ion accumulators [13] [18] and as a fuel additive for diesel. [14]

Isosorbide phosphates

Phosphoric acid derivatives of isosorbide are explored as an environmentally friendly alternative to halogen-containing flame retardants. So far, 1,2,5,6,9,10-hexabromocyclododecane (HBCD) has been widely used as a flame retardant in extruded polystyrene foam (XPS) in the construction and insulation sector, but it was as SVHC (substance of very high concern) banned from manufacturing and application in May 2013. Phosphorus-based isosorbide compounds, such as isosorbide bis (diphenyl phosphate) [ISTP] are considered as a replacement.

Isosorbid-bis(diphenylphosphate) Isosorbid-bis-(diphenylphosphate).svg
Isosorbid-bis(diphenylphosphate)

ISTP is readily accessible by transesterification of isosorbide with triphenyl phosphate in the presence of potassium carbonate at 150 °C. The isosorbide-bis-diphenyl phosphate obtained in 88% yield as a yellowish oil contains about 20% dimers. [15] The high decomposition temperature of ISTP allows a use in XPS, although the high softening effect is a drawback. The flame retardancy is particularly pronounced in the presence of sulfur-containing synergists such as bis(diphenylphosphinothionyl)disulfide (BDPS). This allows to reach the minimum requirement of fire protection (class B2) with only 3% ISTP. [16]

Polymers from Isosorbide

Isosorbide has been examined as a potential platform chemical for the production of diverse polymers and resins. [5] The hydroxy groups can be converted into the primary amino groups [5] via the tosylates and azides or by addition of acrylonitrile followed by hydrogenation into the corresponding aminopropyl derivatives. [17] The latter have potential for the preparation of polyurethanes, as diamines for the preparation of polyamides, and as a hardener for epoxy resins.

When monoethylene glycol as a diol is replaced with isosorbide in the polyester polyethylene terephthalate (PET), polyisosorbide terephthalate (PIT) is obtained, which is characterized by an extreme thermal stability (up to 360 °C under nitrogen). However, the inherently lower reactivity of the secondary hydroxyl groups in isosorbide cause in comparison lower molecular weights and high residual contents of terephthalic acid, which leads to the insufficient chemical stability of the resulting polymers. Therefore, today's polyesters with isosorbide and monoethylene glycol are examined as diol components that show improved properties such as less discoloration. [18] [19]

Isosorbide is of also of interest as a precursor to polycarbonates,. [20] It could in principle replace the bisphenol A, which was identified as xenoestrogen. Limitations of isosorbide-based polycarbonates are their unsatisfactory temperature resistance and limited impact resistance, which can be improved though by the addition of comonomers to the isosorbide or by polymer blends. [21]

Isosorbide, a diol, is a precursor to In polyurethanes. [22] or as a building block for the polyol [23] [29] It could be converted to the diisocyanate component [24] as well as a chain extender. [25]

By reacting isosorbide with epichlorohydrin, isosorbide bis-glycidyl ether [26] (a bis-epoxide) is formed, which could be used as a replacement for the analog bisphenol A bis-epoxide. Isosorbide bis-glycidyl ether can be crosslinked to a thermosetting epoxy resins with suitable curing agents, such as polyamines or cyclic acid anhydrides. These resins are used as adhesives, paints or coatings for food cans. [27] Furthermore, polyoxazolidones are described which can be obtained by reaction of isosorbide diglycidyl ethers with diisocyanates. [28] Polyoxazolidones could find use as rigid, highly branched and solvent-resistant thermoset plastics in the electrical and electronics industry.

Production

Hydrogenation of glucose gives sorbitol. Isosorbide is obtained by acid-catalyzed dehydration of D-sorbitol which yields the monocyclic furanoid sorbitan, [5] which in turn forms by further dehydration the bicyclic furofuran derivative isosorbide. [29]

Sorbitol-Sorbitan-Isosorbid.svg

The reaction gives about 70 to 80% isosorbide in addition to 30 to 20% of undesirable by-products which have to be removed costly by distillation, recrystallization from alcohols, recrystallization from the melt, [30] by a combination of these methods or by deposition from the vapor phase. [31] A high purity product (> 99.8% [31] ) is essential for the use of a monomer when uncoloured, high molecular weight polymers shall be obtained.

Properties

Isosorbide is a white, crystalline, highly hydrophilic solid. The two secondary hydroxy groups in the V-shaped bicyclic system possess different orientations leading to different chemical reactivities. This allows a selective monoderivatization of isosorbide. The hydroxy group in 5-position is endo oriented and forms a hydrogen bond with the oxygen atom in the adjacent furan ring. This makes the hydroxy group in 5-position more nucleophilic and more reactive than the exo oriented hydroxy group in 2-position; however, it is more shielded from the attack of sterically demanding reactants. [32]

Safety

With an LD50 value of 25.8 g·kg−1 (rat, oral [33] ), isosorbide is similarly nontoxic as D-glucose (also with an LD50 of 25.8 g·kg−1, rat, oral [34] ) and is classified by the Food and Drug Administration FDA as GRAS ("generally recognized as safe"). [35]

Related Research Articles

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Polyurethane refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term does not refer to the single type of polymer but a group of polymers. Unlike polyethylene and polystyrene polyurethanes can be produced from a wide range of starting materials resulting various polymers within the same group. This chemical variety produces polyurethanes with different chemical structures leading to many different applications. These include rigid and flexible foams, and coatings, adhesives, electrical potting compounds, and fibers such as spandex and polyurethane laminate (PUL). Foams are the largest application accounting for 67% of all polyurethane produced in 2016.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Thermosetting polymer</span> Polymer obtained by irreversibly hardening (curing) a resin

In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening ("curing") a soft solid or viscous liquid prepolymer (resin). Curing is induced by heat or suitable radiation and may be promoted by high pressure or mixing with a catalyst. Heat is not necessarily applied externally, and is often generated by the reaction of the resin with a curing agent. Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.

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<span class="mw-page-title-main">Hexamethylenediamine</span> Chemical compound

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<span class="mw-page-title-main">2,5-Bis(hydroxymethyl)furan</span> Chemical compound

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<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

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References

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  3. ↑ CID 12597 from PubChem
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  34. ↑ Datenblatt. "D-Glucose" (PDF). Carl Roth  [ de ]. Retrieved 24 August 2010.
  35. ↑ Feng X, East A, Hammond W, Ophir Z, Zhang Y, Jaffe M (September 2012). "Thermal analysis characterization of isosorbide-containing thermosets: Isosorbide epoxy as BPA replacement for thermosets industry". Journal of Thermal Analysis and Calorimetry. 109 (3): 1267–1275. doi:10.1007/s10973-012-2581-2. S2CID   94674402.
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