Names | |
---|---|
Preferred IUPAC name 1,4-Dioxan-2-one | |
Other names para-Dioxanone | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.130.057 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C4H6O3 | |
Molar mass | 102.089 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
p-Dioxanone (1,4-dioxan-2-one) is the lactone of 2-(2-hydroxyethoxy)acetic acid. It is a monomer that can undergo ring-opening polymerization to give polydioxanone, a biodegradable implant material. [1] It is isomeric to trimethylene carbonate (1,3-dioxan-2-one).
The common synthetic process for p-dioxanone is continuous gas-phase dehydrogenation of diethylene glycol on a copper or copper chromite catalyst at 280 °C.
This gives yields of up to 86%. Removal of excess diethylene glycol is crucial to the stability of the product as a monomer. [2] Further purification with recrystallization, vacuum distillation, [3] or melt crystallization [2] allows purities of >99.5% to be achieved.
Pure p-dioxanone is a white crystalline solid with a melting point of 28 °C. [4]
The oxidation of p-dioxanone with nitric acid or dinitrogen tetroxide gives diglycolic acid at 75% yield. [5]
p-Dioxanone can undergo ring-opening polymerization catalyzed by organic compounds of tin, such as tin(II) octoate [6] or dibutyltin dilaurate, or by basic alkoxides such as aluminium isopropoxide. This affords polydioxanone, a biodegradable, semicrystalline and thermally labile polymer with uses in industry and medicine. [7] Depolymerization back to the monomer is triggered at 100 °C.
In chemistry, 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.
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. Ethylene glycol has a sweet taste, but it is toxic in high concentrations. This molecule has been observed in outer space.
In polymer chemistry, an addition polymer is a polymer that forms by simple linking of monomers without the co-generation of other products. Addition polymerization differs from condensation polymerization, which does co-generate a product, usually water. Addition polymers can be formed by chain polymerization, when the polymer is formed by the sequential addition of monomer units to an active site in a chain reaction, or by polyaddition, when the polymer is formed by addition reactions between species of all degrees of polymerization. Addition polymers are formed by the addition of some simple monomer units repeatedly. Generally polymers are unsaturated compounds like alkenes, alkalines etc. The addition polymerization mainly takes place in free radical mechanism. The free radical mechanism of addition polymerization completed by three steps i.e. Initiation of free radical, Chain propagation, Termination of chain.
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:
Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization. PGA has been known since 1954 as a tough fiber-forming polymer. Owing to its hydrolytic instability, however, its use has initially been limited. Currently polyglycolide and its copolymers (poly(lactic-co-glycolic acid) with lactic acid, poly(glycolide-co-caprolactone) with ε-caprolactone and poly (glycolide-co-trimethylene carbonate) with trimethylene carbonate) are widely used as a material for the synthesis of absorbable sutures and are being evaluated in the biomedical field.
Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(COOCH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.
Polylactic acid, also known as poly(lactic acid) or polylactide (PLA), is a thermoplastic polyester with backbone formula (C
3H
4O
2)
n or [–C(CH
3)HC(=O)O–]
n, formally obtained by condensation of lactic acid C(CH
3)(OH)HCOOH with loss of water. It can also be prepared by ring-opening polymerization of lactide [–C(CH
3)HC(=O)O–]
2, the cyclic dimer of the basic repeating unit.
Hot-melt adhesive (HMA), also known as hot glue, is a form of thermoplastic adhesive that is commonly sold as solid cylindrical sticks of various diameters designed to be applied using a hot glue gun. The gun uses a continuous-duty heating element to melt the plastic glue, which the user pushes through the gun either with a mechanical trigger mechanism on the gun, or with direct finger pressure. The glue squeezed out of the heated nozzle is initially hot enough to burn and even blister skin. The glue is sticky when hot, and solidifies in a few seconds to one minute. Hot-melt adhesives can also be applied by dipping or spraying, and are popular with hobbyists and crafters both for affixing and as an inexpensive alternative to resin casting.
Polyester is a category of polymers that contain the ester functional group 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.
Barrelene is a bicyclic organic compound with chemical formula C8H8 and systematic name bicyclo[2.2.2]octa-2,5,7-triene. First synthesized and described by Howard Zimmerman in 1960, the name derives from the resemblance to a barrel, with the staves being three ethylene units attached to two methine groups. It is the formal Diels–Alder adduct of benzene and acetylene. Due to its unusual molecular geometry, the compound is of considerable interest to theoretical chemists.
Polyanhydrides are a class of biodegradable polymers characterized by anhydride bonds that connect repeat units of the polymer backbone chain. Their main application is in the medical device and pharmaceutical industry. In vivo, polyanhydrides degrade into non-toxic diacid monomers that can be metabolized and eliminated from the body. Owing to their safe degradation products, polyanhydrides are considered to be biocompatible.
Biodegradable polymers are a special class of polymer that breaks down after its intended purpose by bacterial decomposition process to result in natural byproducts such as gases (CO2, N2), water, biomass, and inorganic salts. These polymers are found both naturally and synthetically made, and largely consist of ester, amide, and ether functional groups. Their properties and breakdown mechanism are determined by their exact structure. These polymers are often synthesized by condensation reactions, ring opening polymerization, and metal catalysts. There are vast examples and applications of biodegradable polymers.
Diglycolic acid is an aliphatic dicarboxylic acid, its acidity is between the one of acetic acid and oxalic acid. It is formed in the oxidation of diethylene glycol in the body and can lead to severe complications with fatal outcome.
N,N′-Methylenebisacrylamide (MBAm or MBAA, colloquially "bis") is the organic compound with the formula CH2[NHC(O)CH=CH2]2. A colorless solid, this compound is a crosslinking agent in polyacrylamides, e.g., as used for SDS-PAGE.
Laurolactam is an organic compound from the group of macrocyclic lactams. Laurolactam is mainly used as a monomer in engineering plastics, such as nylon-12 and copolyamides.
Poly(ethylene adipate) or PEA is an aliphatic polyester. It is most commonly synthesized from a polycondensation reaction between ethylene glycol and adipic acid. PEA has been studied as it is biodegradable through a variety of mechanisms and also fairly inexpensive compared to other polymers. Its lower molecular weight compared to many polymers aids in its biodegradability.
Allyl glycidyl ether is an organic compound used in adhesives and sealants and as a monomer for polymerization reactions. It is formally the condensation product of allyl alcohol and glycidol via an ether linkage. Because it contains both an alkene and an epoxide group, either group can be reacted selectively to yield a product where the other functional group remains intact for future reactions.
Nitrilotriacetonitrile (NTAN) is a precursor for nitrilotriacetic acid, for tris(2-aminoethyl)amine and for the epoxy resin crosslinker aminoethylpiperazine.
3,9-Divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane (DVTOSU) is a bicyclic organic molecule having a central quaternary carbon atom with which two alicyclic rings are linked, each comprising five atoms. DVTOSU is a diallyl acetal and the precursor for the isomeric ketene acetal monomer 3,9-diethylidene-2,4,8,10-tetraoxaspiro[5.5]undecane (DETOSU) which is a building block for polyorthoesters.
β-Butyrolactone is the intramolecular carboxylic acid ester (lactone) of the optically active 3-hydroxybutanoic acid. It is produced during chemical synthesis as a racemate. β-Butyrolactone is suitable as a monomer for the production of the biodegradable polyhydroxyalkanoate poly(3-hydroxybutyrate) (PHB). Polymerisation of racemic (RS)-β-butyrolactone provides (RS)-polyhydroxybutyric acid, which, however, is inferior in essential properties (e.g. strength or degradation behaviour) to the (R)-poly-3-hydroxybutyrate originating from natural sources.
{{cite book}}
: |work=
ignored (help)