1,6-Hexanediol

Last updated
1,6-Hexanediol
1,6-Hexanediol.svg
Names
Preferred IUPAC name
Hexane-1,6-diol
Other names
Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.068 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-074-0
PubChem CID
RTECS number
  • MO2100000
UNII
  • InChI=1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2 Yes check.svgY
    Key: XXMIOPMDWAUFGU-UHFFFAOYSA-N Yes check.svgY
  • OCCCCCCO
Properties
C6H14O2
Molar mass 118.176 g·mol−1
Density 0.967
Melting point 42 °C (108 °F; 315 K)
Boiling point 250 °C (482 °F; 523 K)
500g/L [1]
Solubility soluble in ethanol and acetone, slightly soluble in diethyl ether, insoluble in benzene. [2]
Hazards
Flash point 102 °C (216 °F; 375 K)
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 ?)

1,6-Hexanediol is an organic compound with the formula (CH2CH2CH2OH)2. It is a colorless water-soluble solid. [3]

Contents

History and synthesis

W. H. Perkin Jr. and his graduate student Edward Haworth first prepared the compound in 1894 during their research on cyclohexane. They boiled 1,6-dibromohexane (which they were also the first to synthesize) with dilute potassium carbonate solution and named the product hexamethylene glycol. [4]

1,6-Hexanediol is industrially made by the hydrogenation of adipic acid or its esters. [3] [5] Laboratory preparation could be achieved by reduction of adipates with lithium aluminium hydride, although this method is impractical on a commercial scale.

Properties

As 1,6-hexanediol contains hydroxyl groups, it undergoes the typical chemical reactions of alcohols such as dehydration, substitution, and esterification. Oxidation with pyridinium chlorochromate gives adipaldehyde. [6]

Dehydration of 1,6-hexanediol gives oxepane, 2-methyltetrahydropyran and 2-ethyltetrahydrofuran. Corresponding thiophene and pyrrolidone can be made by reacting 1,6-hexanediol with hydrogen sulfide and ammonia respectively. [7]

Uses

1,6-Hexanediol is widely used for industrial polyester and polyurethane production.. [3]

1,6-Hexanediol can improve the hardness and flexibility of polyesters as it contains a fairly long hydrocarbon chain. In polyurethanes, it is used as a chain extender, and the resulting modified polyurethane has high resistance to hydrolysis as well as mechanical strength, but with a low glass transition temperature.

It is also an intermediate to acrylics as a crosslinking agent, e.g. hexanediol diacrylate. [3] Unsaturated polyester resins have also been made from 1,6-hexanediol, along with styrene, maleic anhydride and fumaric acid. [7]

Uses to study biomolecular condensates

1,6-Hexanediol has been used to characterize biomolecular condensates. The material properties of condensates can be examined to determine if they are solid or liquid condensates. 1,6-Hexanediol has been reported to interfere with weak hydrophobic protein-protein or protein-RNA interactions that comprise liquid condensates. 1,6-Hexanediol has been reported to dissolve liquid but not solid condensates. [8] 2,5-Hexanediol and 1,4-butanediol have been observed to have minimal effect on behavior of disorderd proteins as compared to 1,6-hexanediol. [9] [10]

Safety

1,6-Hexanediol [11] has low toxicity and low flammability, and is generally considered as safe. It is not irritating to skin, but may irritate the respiratory tract or mucous membranes. Dust or vapor of the compound can irritate or damage the eyes. [1]

Related Research Articles

<span class="mw-page-title-main">Polyurethane</span> Polymer composed of a chain of organic units joined by carbamate (urethane) links

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">Ethylene glycol</span> Organic compound ethane-1,2-diol

Ethylene glycol is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is toxic in high concentrations. This molecule has been observed in outer space.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.

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

Pyridinium refers to the cation [C5H5NH]+. It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids.

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

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups. The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, three and four hydroxyl groups are diols, triols, and tetrols, respectively.

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

Pyridinium chlorochromate (PCC) is a yellow-orange salt with the formula [C5H5NH]+[CrO3Cl]. It is a reagent in organic synthesis used primarily for oxidation of alcohols to form carbonyls. A variety of related compounds are known with similar reactivity. PCC offers the advantage of the selective oxidation of alcohols to aldehydes or ketones, whereas many other reagents are less selective.

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

Biuret is a chemical compound with the chemical formula HN(CONH2)2. It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula R1R2N−C(=O)−N(R3)−C(=O)−NR4R5, where R1, R2, R3, R4 and R5 are hydrogen, organyl or other groups. Also known as carbamylurea, it results from the condensation of two equivalents of urea. It is a common undesirable impurity in urea-based fertilizers, as biuret is toxic to plants.

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

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Polyester</span> Category of polymers, in which the monomers are joined together by ester links

Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

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

Hexamethylene diisocyanate (HDI) is the organic compound with the formula (CH2)6(NCO)2. It is classified as an diisocyanate. It is a colorless liquid. It has sometimes been called HMDI but this not usually done to avoid confusion with Hydrogenated MDI.

Polyester resins are synthetic resins formed by the reaction of dibasic organic acids and polyhydric alcohols. Maleic anhydride is a commonly used raw material with diacid functionality in unsaturated polyester resins. Unsaturated polyester resins are used in sheet moulding compound, bulk moulding compound and the toner of laser printers. Wall panels fabricated from polyester resins reinforced with fiberglass—so-called fiberglass reinforced plastic (FRP)—are typically used in restaurants, kitchens, restrooms and other areas that require washable low-maintenance walls. They are also used extensively in cured-in-place pipe applications. Departments of Transportation in the USA also specify them for use as overlays on roads and bridges. In this application they are known AS Polyester Concrete Overlays (PCO). These are usually based on isophthalic acid and cut with styrene at high levels—usually up to 50%. Polyesters are also used in anchor bolt adhesives though epoxy based materials are also used. Many companies have and continue to introduce styrene free systems mainly due to odor issues, but also over concerns that styrene is a potential carcinogen. Drinking water applications also prefer styrene free. Most polyester resins are viscous, pale coloured liquids consisting of a solution of a polyester in a reactive diluent which is usually styrene, but can also include vinyl toluene and various acrylates.

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

Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.

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

The Cornforth reagent (pyridinium dichromate or PDC) is a pyridinium salt of dichromate with the chemical formula [C5H5NH]2[Cr2O7]. This compound is named after the Australian-British chemist Sir John Warcup Cornforth (b. 1917) who introduced it in 1962. The Cornforth reagent is a strong oxidizing agent which can convert primary and secondary alcohols to aldehydes and ketones respectively. In its chemical structure and functions it is closely related to other compounds made from hexavalent chromium oxide, such as pyridinium chlorochromate and Collins reagent. Because of their toxicity, these reagents are rarely used nowadays.

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

Polytetrahydrofuran, also called poly(tetramethylene ether) glycol or poly(tetramethylene oxide), is a collection of chemical compounds with formula HO(CH2)4O(CH2)4)nOH or HO((CH2)4O-)n-H. The material is a mixture of polyether diols terminated with alcohol groups. It is produced by polymerization of tetrahydrofuran as well as 1,4-butanediol.

Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids.

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

Levoglucosenone is an organic compound with the formula [OCH2(CH)4CO2]. A pale yellow liquid, it is an unsaturated bicyclic ketone-diether formed from levoglucosan by loss of two molecules of water. As a product of the acid-catalysed pyrolysis of cellulose, D-glucose, and levoglucosan, this liquid hydrocarbon is of interest as a biofuel and biofeedstock.

<span class="mw-page-title-main">2,5-Hexanediol</span> Chemical compound

2,5-Hexanediol is an organic compound with the formula CH3CH(OH)CH2CH2CH(OH)CH3. It is both a glycol and a secondary alcohol. It is a colorless water-soluble viscous liquid. The chemical properties are well understood and have been extensively reported and studied. It has the IUPAC name of hexane-2,5-diol and the CAS Registry Number CAS 2935-44-6.

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

Adipaldehyde is the organic compound with the formula (CH2)4(CHO)2. It is a colorless oil that is usually encountered as an aqueous solution because it is highly reactive like many dialdehydes. The compound has attracted interest as a precursor to nylon-related polymers. It can be produced by double hydroformylation of 1,3-butadiene, but this methodology has not achieved commercialization. It has been prepared by oxidation of 1,6-hexanediol with pyridinium chlorochromate.

References

  1. 1 2 Chemicals and reagents 2008-2010, Merck
  2. CRC Handbook of Chemistry and Physics, 87th Edition
  3. 1 2 3 4 Peter Werle; Marcus Morawietz; Stefan Lundmark; Kent Sörensen; Esko Karvinen; Juha Lehtonen (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN   978-3527306732.
  4. Haworth, E.; Perkin, W. H. (1894). "Hexamethylene dibromide and its action on sodium and on ethylic sodio-malonate". Journal of the Chemical Society, Transactions. 65 (0): 591–602. doi:10.1039/CT8946500591. ISSN   0368-1645.
  5. Lazier, W. A.; Hill, J. W.; Amend, W. J. (1939). "Hexamethylene glycol". Org. Synth. 19: 48. doi:10.15227/orgsyn.019.0048.
  6. Corey, E.J.; Suggs, J.William (1975). "Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds". Tetrahedron Letters. 16 (31): 2647–2650. doi:10.1016/s0040-4039(00)75204-x.
  7. 1 2 BASF intermediates, BASF
  8. Kroschwald, Sonja; Maharana, Shovamayee; Simon, Alberti (2017-05-22). "Hexanediol: a chemical probe to investigate the material properties of membrane-less compartments". Matters. doi: 10.19185/matters.201702000010 . ISSN   2297-8240.
  9. Kato, Masato; McKnight, Steven L. (2018-06-20). "A Solid-State Conceptualization of Information Transfer from Gene to Message to Protein". Annual Review of Biochemistry. 87: 351–390. doi:10.1146/annurev-biochem-061516-044700. ISSN   1545-4509. PMID   29195049. S2CID   28314614.
  10. Franco, Hector L.; Nagari, Anusha; Kraus, W. Lee (2015-04-02). "TNFα signaling exposes latent estrogen receptor binding sites to alter the breast cancer cell transcriptome". Molecular Cell. 58 (1): 21–34. doi:10.1016/j.molcel.2015.02.001. ISSN   1097-4164. PMC   4385449 . PMID   25752574.
  11. Solutions, Navux Commerce. "1,6 Hexanediol (Cas 629-11-8) - Bulk Specialty Chemical Supplier & distributor". www.parchem.com. Retrieved 2024-06-27.