Bis(2-Hydroxyethyl) terephthalate

Last updated
Bis(2-Hydroxyethyl) terephthalate
Bis(2-hydroxyethyl) terephthalate.svg
Names
Preferred IUPAC name
Bis(2-hydroxyethyl) benzene-1,4-dicarboxylate [1]
Other names
Bis(2-hydroxyethyl) terephthalate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.270 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H14O6/c13-5-7-17-11(15)9-1-2-10(4-3-9)12(16)18-8-6-14/h1-4,13-14H,5-8H2
    Key: QPKOBORKPHRBPS-UHFFFAOYSA-N
  • InChI=1/C12H14O6/c13-5-7-17-11(15)9-1-2-10(4-3-9)12(16)18-8-6-14/h1-4,13-14H,5-8H2
    Key: QPKOBORKPHRBPS-UHFFFAOYAN
  • O=C(OCCO)c1ccc(C(=O)OCCO)cc1
Properties
C12H14O6
Molar mass 254.238 g·mol−1
AppearanceWhite powder
Density 1.3 (±0.1) g/cm3
Melting point 106 °C
0.593 g/L [2]
Hazards
Flash point 172.0 (±19.4) °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bis(2-Hydroxyethyl) terephthalate (BHET) is an organic compound; it is the ester of ethylene glycol and terephthalic acid. Together with 2-hydroxyethyl terephthalic acid, bis(2-Hydroxyethyl) terephthalate is an intermediate in the production of poly(ethylene terephthalate). It is the product of the glycolysis reaction of PET with Ethylene glycol.

Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Ethylene</span> Hydrocarbon compound (H₂C=CH₂)

Ethylene is a hydrocarbon which has the formula C2H4 or H2C=CH2. It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene.

A monomer is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization.

<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.

<span class="mw-page-title-main">Polyethylene terephthalate</span> Polymer

Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also 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">PET bottle recycling</span> Recycling of bottles made of polyethylene terephthalate

Although PET is used in several applications, as of 2022 only bottles are collected at a substantial scale. The main motivations have been either cost reduction or recycle content of retail goods. An increasing amount is recycled back into bottles, the rest goes into fibres, film, thermoformed packaging and strapping. After sorting, cleaning and grinding, 'bottle flake' is obtained, which is then processed by either:

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

Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

In polymer chemistry, a structural unit is a building block of a polymer chain. It is the result of a monomer which has been polymerized into a long chain.

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

Terephthaloyl chloride is the acyl chloride of terephthalic acid. It is a white solid. It is one of two precursors used to make Kevlar, the other being p-phenylenediamine. TCL is used as a key component in performance polymers and aramid fibers, where it imparts flame resistance, chemical resistance, temperature stability, light weight, and very high strength. TCL is also an effective water scavenger, used to stabilize isocyanates and urethane prepolymers.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

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

Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula (CH3OCH2CH2)2O. It is a colorless liquid with a slight ether-like odor. It is a solvent with a high boiling point. It is the dimethyl ether of diethylene glycol. The name diglyme is a portmanteau of diglycol methyl ether. It is miscible with water as well as organic solvents.

In polymer chemistry, a repeat unit or repeating unit is a part of a polymer whose repetition would produce the complete polymer chain by linking the repeat units together successively along the chain, like the beads of a necklace.

Commodity chemicals are a group of chemicals that are made on a very large scale to satisfy global markets. The average prices of commodity chemicals are regularly published in the chemical trade magazines and web sites such as Chemical Week and ICIS. There have been several studies of the scale and complexity of this market for example in the USA.

Ideonella sakaiensis is a bacterium from the genus Ideonella and family Comamonadaceae capable of breaking down and consuming the plastic polyethylene terephthalate (PET) using it as both a carbon and energy source. The bacterium was originally isolated from a sediment sample taken outside of a plastic bottle recycling facility in Sakai City, Japan.

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

Polyethylene furan-2,5-dicarboxylate, also named poly(ethylene furan-2,5-dicarboxylate), polyethylene furanoate and poly(ethylene furanoate) and generally abbreviated as PEF, is a polymer that can be produced by polycondensation or ring-opening polymerization of 2,5-furandicarboxylic acid (FDCA) and ethylene glycol. As an aromatic polyester from ethylene glycol it is a chemical analogue of polyethylene terephthalate (PET) and polyethylene naphthalate (PEN). PEF has been described in (patent) literature since 1951, but has gained renewed attention since the US department of energy proclaimed its building block, FDCA, as a potential bio-based replacement for purified terephthalic acid (PTA) in 2004.

<span class="mw-page-title-main">PETase</span> Class of enzymes

PETases are an esterase class of enzymes that catalyze the breakdown (via hydrolysis) of polyethylene terephthalate (PET) plastic to monomeric mono-2-hydroxyethyl terephthalate (MHET). The idealized chemical reaction is:

2-Hydroxyethyl terephthalic acid is an organic compound with the formula HOC2H4O2CC6H4CO2H. It is the monoester of terephthalic acid and ethylene glycol. The compound is a precursor to poly(ethylene terephthalate) (PET), a polymer that is produced on a large scale industrially. 2-Hydroxyethyl terephthalic acid is a colorless solid that is soluble in water and polar organic solvents. Near neutral pH, 2-hydroxyethyl terephthalic acid converts to 2-hydroxyethyl terephthalate, HOC2H4O2CC6H4CO2.

<span class="mw-page-title-main">MHETase</span>

The enzyme MHETase is a hydrolase, which was discovered in 2016. It cleaves 2-hydroxyethyl terephthalic acid, the PET degradation product by PETase, to ethylene glycol and terephthalic acid. This pair of enzymes, PETase and MHETase, enable the bacterium Ideonella sakaiensis to live on the plastic PET as sole carbon source.

References

  1. IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-65.1.1.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPACRSC. ISBN   978-0-85404-182-4.
  2. Yuan, Peiquan; Liu, Baoshu; Li, Qiuju; Sun, Hua (2022). "Solubility Determination and Correlation for Bis(2-hydroxyethyl) Terephthalate (BHET) in Four Binary Solvents from 283.15 to 323.15 K". Journal of Chemical & Engineering Data. 67 (9): 2693–2705. doi:10.1021/acs.jced.2c00194.