Piperylene

Last updated
Piperylene [1]
Piperylene.svg
Piperylene3D.png
Names
Preferred IUPAC name
(3E)-Penta-1,3-diene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.269 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-995-2
PubChem CID
RTECS number
  • RZ2464000
UNII
UN number 1993 3295 1010
  • InChI=1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+ X mark.svgN
    Key: PMJHHCWVYXUKFD-SNAWJCMRSA-N X mark.svgN
  • InChI=1/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3/b5-4+
    Key: PMJHHCWVYXUKFD-SNAWJCMRBX
  • C/C=C/C=C
Properties
C5H8
Molar mass 68.117 g/mol
AppearanceColorless liquid
Density 0.683 g/cm3
Melting point −87 °C (−125 °F; 186 K) E-isomer
Boiling point 42 °C (108 °F; 315 K) E-isomer
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H304, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point <−30 °C (−22 °F; 243 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 ?)

Piperylene or 1,3-pentadiene is an organic compound with the formula CH3CH=CH-CH=CH2. It is a volatile, flammable hydrocarbon. It is one of the five positional isomers of pentadiene.

Contents

Reactions and occurrence

Piperylene is a typical diene. It forms a sulfolene upon treatment with sulfur dioxide. [2]

Piperylene is the product of the decarboxylation of sorbic acid, a common anti-mold agent. [3]

Piperylene is obtained as a byproduct of ethylene production from crude oil, combustion of biomass, waste incineration and exhaust gases. It is used as a monomer in the manufacturing of plastics, adhesives and resins. [4]

See also

Related Research Articles

Diene Covalent compound that contains two double bonds

In organic chemistry a diene is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alkene units, with the standard prefix di of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition.

Acetophenone Chemical compound

Acetophenone is the organic compound with the formula C6H5C(O)CH3 (also represented by the pseudoelement symbols PhAc or BzMe). It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.

Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber. C. G. Williams named the compound in 1860 after obtaining it from thermal decomposition (pyrolysis) of natural rubber; he correctly deduced the empirical formula C5H8.

In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Sorbic acid Chemical compound

Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula CH3(CH)4CO2H. It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isolated from the unripe berries of the Sorbus aucuparia (rowan tree), hence its name..

Ethyl acetate Chemical compound

Ethyl acetate is the organic compound with the formula CH3−COO−CH2−CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

Acetic anhydride Chemical compound

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Potassium sorbate Chemical compound

Potassium sorbate is the potassium salt of sorbic acid, chemical formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202). Potassium sorbate is effective in a variety of applications including food, wine, and personal-care products. While sorbic acid occurs naturally in some berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically.

Acidity regulator

Acidity regulators, or pH control agents, are food additives used to change or maintain pH. They can be organic or mineral acids, bases, neutralizing agents, or buffering agents. Typical agents include the following acids and their sodium salts: sorbic acid, acetic acid, benzoic acid, and propionic acid. Acidity regulators are indicated by their E number, such as E260, or simply listed as "food acid".

Trimethylsilyldiazomethane Chemical compound

Trimethylsilyldiazomethane is the organosilicon compound with the formula (CH3)3SiCHN2. It is classified as a diazo compound. Trimethylsilyldiazomethane is a commercially available reagent used in organic chemistry as a methylating agent and as a source of CH2 group. Its behavior is akin to the less convenient reagent diazomethane.

3-Methylbutanoic acid Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2

3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.

Crotonaldehyde Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

In chemistry, pentadiene is any hydrocarbon with an open chain of five carbons, connected by two single bonds and two double bonds. All those compounds have the same molecular formula C
5
H
8
. Specifically, it may be

C<sub>5</sub>H<sub>8</sub> Index of chemical compounds with the same molecular formula

The molecular formula C5H8 may refer to any of the following hydrocarbons:

Vinylogy

Vinylogy is the transmission of electronic effects through a conjugated organic bonding system. The concept was introduced in 1926 by Ludwig Claisen to explain the acidic properties of formylacetone and related ketoaldehydes. Its adjectival form, vinylogous, is used to describe functional groups in which the standard moieties of the group are separated a carbon–carbon double bond. For example, a carboxylic acid with a carbon-carbon double bond between a carbonyl group and a hydroxyl group is referred to as a vinylogous carboxylic acid.

Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.

Dimethylbutadiene, formally referred to as 2,3-dimethyl-1,3-butadiene, is an organic compound with the formula (CH3)2C4H4. It is colorless liquid which served an important role in the early history of synthetic rubber. It is now a specialty reagent.

Allyl iodide Chemical compound

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones, sorbic acid esters, 5,5-disubstituted barbituric acids, and organometallic catalysts. Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite, Finkelstein reaction on allyl halides, or by the action of elemental phosphorus and iodine on glycerol. Allyl iodide dissolved in hexane can be stored for up to three months in a dark freezer at −5 °C (23 °F) before decomposition into free iodine becomes apparent.

Alkynylation is an addition reaction in organic synthesis where a terminal alkyne adds to a carbonyl group to form an α-alkynyl alcohol. When the acetylide is formed from acetylene, the reaction gives an α-ethynyl alcohol. This process is often referred to as ethynylation. Such process often involve metal acetylide intermediates

References

  1. Safety (MSDS) data for piperylene. Retrieved 2007-11-14.
  2. Robert L. Frank, Raymond P. Seven (1949). "Isoprene Cyclic Sulfone". Organic Syntheses. 29: 59. doi:10.15227/orgsyn.029.0059.
  3. Erich Lück, Martin Jager, Nico Raczek (2000). "Sorbic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_507. ISBN   3527306730.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  4. Piperylene Archived 2009-05-13 at the Wayback Machine at Shell Chemicals. Retrieved 2009-05-19.