Dibutyl maleate

Last updated
Maleic acid dibutyl ester
Maleinsauredibutylester.svg
Names
Preferred IUPAC name
Dibutyl (2Z)-but-2-enedioate
Other names
  • Maleic acid dibutyl ester
  • DBM
Identifiers
3D model (JSmol)
3DMet
ChEMBL
ChemSpider
ECHA InfoCard 100.003.027 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-328-4
MeSH maleate dibutyl maleate
PubChem CID
UNII
  • InChI=1S/C12H20O4/c1-3-5-9-15-11(13)7-8-12(14)16-10-6-4-2/h7-8H,3-6,9-10H2,1-2H3/b8-7-
    Key: JBSLOWBPDRZSMB-FPLPWBNLSA-N
  • CCCCOC(=O)/C=C\C(=O)OCCCC
Properties
C12H20O4
Molar mass 228.288 g·mol−1
AppearanceColorless to yellowish liquid with a characteristic odor [1]
Density 0.99 g·cm−3 [1]
Melting point −85 °C (−121 °F; 188 K) [1]
Boiling point 280 °C (536 °F; 553 K) [1]
Very hardly soluble (0.17 g·l−1 at 20 °C) [1]
Vapor pressure 0.0027 hPa (20 °C) [1]
1.445 (20 °C) [2]
Hazards
GHS pictograms GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg [1]
H317, H373, H411 [1]
P273, P280, P302+352, P314 [1]
Flash point 141 °C (286 °F; 414 K) [1]
265 °C (509 °F; 538 K) [1]
Explosive limits
  • Lower limit: 0.5 vol-% [1]
  • Upper limit: 3.4 vol-% [1]
Lethal dose or concentration (LD, LC):
  • 3700 mg·kg−1 (rat, oral) [1]
  • 10000 mg·kg−1 (rabbit, dermal) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dibutyl maleate is an organic compound with the formula (CHCO2Bu)2 (Bu = butyl). It is the diester of the unsaturated dicarboxylic acid maleic acid. It is a colorless oily liquid, although impure samples can appear yellow.

Contents

Preparation

Dibutyl maleate can be prepared by the reaction of maleic acid anhydride and 1-butanol in presence of p-toluenesulfonic acid. [3] [4]

Uses

Dibutyl maleate is mainly used as a plasticizer for aqueous dispersions of copolymers with vinyl acetate and as an intermediate in the preparation of other chemical compounds. [5] With the invention of polyaspartic technology the material found another use. In this situation, an amine is reacted with a dialkyl maleate - usually diethyl maleate but also dibutyl maleate may be used- utilizing the Michael addition reaction. The resulting products, polyaspartic esters products are then used in coatings, adhesives, sealants and elastomers. [6]

See also

Related Research Articles

Phthalic anhydride Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

Malonic acid Carboxylic acid with chemical formula CH2(COOH)2

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

Oxazolidine Chemical compound

An oxazolidine is a five-membered ring compound consisting of three carbon atoms, a nitrogen atom and an oxygen atom. The O atom and NH group are the 1 and 3 positions, respectively. In oxazolidine derivatives, there is always a carbon atom between the O and N atoms. All of the carbon atoms in oxazolidines are reduced. Some of their derivatives, the oxazolidinediones, are used as anticonvulsants.

Polyurea Class of elastomers

Polyurea is a type of elastomer that is derived from the reaction product of an isocyanate component and a synthetic resin blend component through step-growth polymerization. The isocyanate can be aromatic or aliphatic in nature. It can be monomer, polymer, or any variant reaction of isocyanates, quasi-prepolymer or a prepolymer. The prepolymer, or quasi-prepolymer, can be made of an amine-terminated polymer resin, or a hydroxyl-terminated polymer resin.

Organic acid anhydride Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

Maleic acid Dicarboxylic acid

Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.

Maleic anhydride Chemical compound

Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.

Chlorendic acid Chemical compound

Chlorendic acid, or 1,4,5,6,7,7-hexachlorobicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylic acid, is a chlorinated hydrocarbon used in the synthesis of some flame retardants and polymers. It is a common breakdown product of several organochlorine insecticides.

Alkyd

An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and organic acids. The inclusion of a fatty acid confers a tendency to form flexible coatings. Alkyds are used in paints, varnishes and in moulds for casting. They are the dominant resin or binder in most commercial oil-based coatings. Approximately 200,000 tons of alkyd resins are produced each year. The original alkyds were compounds of glycerol and phthalic acid sold under the name Glyptal. These were sold as substitutes for the darker-colored copal resins, thus creating alkyd varnishes that were much paler in colour. From these, the alkyds that are known today were developed.

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 PCO Polyester Concrete Overlays. 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. 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.

Cellulose acetate phthalate (CAP), also known as cellacefate (INN) and cellulosi acetas phthalas, is a commonly used polymer phthalate in the formulation of pharmaceuticals, such as the enteric coating of tablets or capsules and for controlled release formulations. It is a cellulose polymer where about half of the hydroxyls are esterified with acetyls, a quarter are esterified with one or two carboxyls of a phthalic acid, and the remainder are unchanged. It is a hygroscopic white to off-white free-flowing powder, granules, or flakes. It is tasteless and odorless, though may have a weak odor of acetic acid. Its main use in pharmaceutics is with enteric formulations. It can be used together with other coating agents, e.g. ethyl cellulose. Cellulose acetate phthalate is commonly plasticized with diethyl phthalate, a hydrophobic compound, or triethyl citrate, a hydrophilic compound; other compatible plasticizers are various phthalates, triacetin, dibutyl tartrate, glycerol, propylene glycol, tripropionin, triacetin citrate, acetylated monoglycerides, etc.

Dimethyl maleate Chemical compound

Dimethyl maleate is an organic compound with the formula C6H8O4. It is the dimethyl ester of maleic acid.

Polyaspartic chemistry was first introduced in the early 1990s making it a relatively new technology. The patents were issued to Bayer in Germany and Miles Corporation in the United States. Pure polyurea reacts extremely quickly making them almost unusable without plural component spray equipment. Polyaspartic technology utilizes a partially blocked amine to react more slowly with the isocyanates and thus produce a modified polyurea. The amine/diamine or even triamine functional coreactant for aliphatic polyisocyanate is typically reacted with a maleate. Polyaspartic esters (PAE) as they are often called, initially found use in conventional solvent-borne two-component polyurethane coatings.

Bis(2-ethylhexyl) maleate is the chemical compound with the structural formula (H
3
C
3
−CH −CH
2
−O−C −CH=)
2
, where the two carboxylate groups are mutually cis. It can be described as the double ester of maleic acid with the alcohol 2-ethylhexanol. It is commonly called dioctyl maleate (DOM), reflecting the older usage of "octane" to refer to any 8-carbon alkane, straight-chained or branched.

Dimethylol propionic acid Organic compound with one carboxyl and two hydroxyl groups

Dimethylol propionic acid -DMPA is a chemical compound that has the full IUPAC name of 2,2-bis(hydroxymethyl)propionic acid and is an organic compound with one carboxyl and two hydroxy groups. It has the CAS Registry Number of 4767-03-7.

Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomers and composite materials. When the phrase waterborne resin is used it usually describes all resins which have water as the main carrying solvent. The resin could be water soluble, water reducible or water dispersed.

1,2-Diaminocyclohexane Chemical compound

1,2-Diaminocyclohexane is an organic compound with the formula (CH2)4(CHNH2)2. It is a mixture of three stereoisomers: cis-1,2-diaminocyclohexane and both enantiomers of trans-1,2-diaminocyclohexane. The mixture is a colorless, corrosive liquid, although older samples can appear yellow. It is often called DCH-99 and also DACH.

Diethyl maleate is an organic compound with the CAS Registry number 141-05-9. It is chemically a maleate ester with the formula C8H12O4. It is a colorless liquid at room temperature. It has the IUPAC name of diethyl (Z)-but-2-enedioate.

Alpha-beta Unsaturated carbonyl compounds

α,β-Unsaturated carbonyl compounds refers to organic compounds with the general structure (O=CR)−Cα=Cβ-R. Examples would be enones and enals. In these compounds the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

Hydrogenated MDI (H12MDI or 4,4′-diisocyanato dicyclohexylmethane) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is a water white liquid at room temperature and is manufactured in relatively small quantities. It is also known as 4,4'-methylenedi(cyclohexyl isocyanate) or methylene bis(4-cyclohexylisocyanate) and has the formula CH2[(C6H10)NCO]2.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Record of Maleinsäuredibutylester in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 3 April 2019.
  2. Sigma-Aldrich Co., Dibutyl maleate, 96%. Retrieved on 2019-04-03.
  3. R. Wen, L. Long, L. Ding, Silas Yu (2001). "Study on synthesis of dibutyl maleate". Jishou Daxue Xuebao/Journal of Jishou University. 22 (1): 78–80.CS1 maint: multiple names: authors list (link)
  4. B. Trivedi (2013). Maleic Anhydride. Springer Science & Business Media. p. 277. ISBN   978-1-4757-0940-7.
  5. Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Dibutyl maletate (pdf) (Report). OECD . Retrieved 3 April 2019.
  6. Howarth, GA (2003-06-01). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 111–118. doi:10.1007/BF02699621. ISSN   1476-4865.