1-octene

Structural formula
General
Surname	1-octene
other names	1-octylene; Oct-1-en; Caprylics;
Molecular formula	C 8 H 16
Brief description	colorless liquid with a gasoline-like odor
External identifiers / databases
EC number	203-893-7
ECHA InfoCard	100.003.540
PubChem	8125
Wikidata	Q161664
properties
Molar mass	112.22 g mol −1
Physical state	liquid
density	0.71 g cm −3 (20 ° C)
Melting point	−102 ° C
boiling point	121 ° C
Vapor pressure	22.7 hPa (20 ° C); 37.8 hPa (30 ° C); 60.4 hPa (40 ° C); 93.5 hPa (50 ° C);
solubility	very slightly soluble in water (4.1 mg l −1 at 25 ° C); soluble in acetone , ethanol , diethyl ether and benzene ;
Refractive index	1.4087
safety instructions
H and P phrases	H: 225-304-410
	P: 210-273-301 + 310-331-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1-Octene is a chemical compound from the group of unsaturated, aliphatic hydrocarbons (more precisely the alkenes ) and is isomeric to isooctene and often occurs together with this and other isomers.

Occurrence

1-Octene is a product of petroleum distillation and occurs as a component in gasoline .

Extraction and presentation

It can be produced industrially in various ways. These are the oligomerization of ethylene (although there are various processes for this), a telomerization of butadiene and by Fischer-Tropsch synthesis with subsequent purification.

properties

Physical Properties

1-Octene is a colorless liquid that boils at 121 ° C under normal pressure . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.05752, B = 1353.486 and C = −60.386 in the temperature range from 318 to 395 K. The critical values are 294 ° C for the critical temperature, 26.8 bar for the critical pressure, 2.8 mol·l ⁻¹ for the critical density and 0.468 l · mol ⁻¹ for the critical volume. An azeotrope boiling at 88 ° C is formed with water . The azeotrope composition is 28.7% by mass of water and 71.3% by mass of 1-octene.

Chemical properties

The compound tends to form peroxides in the presence of air . A strongly exothermic reaction is observed with alkaline substances, bromine , hydrogen bromide , chlorine , hydrogen chloride and oxidizing agents. The presence of radical formers, alkalis or acids can initiate spontaneous polymerization .

Safety-related parameters

1-Octene forms highly flammable vapor-air mixtures. The compound has a flash point of 10 ° C. The explosion range is between 0.7% by volume as the lower explosion limit (LEL) and 6.8% by volume as the upper explosion limit (UEL). The ignition temperature is 240 ° C. The substance therefore falls into temperature class T3.

use

1-Octene is used as a starting material in organic syntheses, for example as a comonomer in the production of polyethylene , in the production of linear aldehydes by hydroformylation and in addition reactions such as epoxidation , dihydroxylation, hydrometalation, carbometalation, radical addition and Wacker oxidation. It can also be cycloisomerized to aromatics. It is used to manufacture plasticizers, surface-active substances and lubricants. It is used as a reference substance in gas chromatography .

toxicology

The liquid is irritating to the skin and eyes. The vapors are also irritating and, in high concentrations, can lead to lung damage and CNS depression.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 1-octene in the GESTIS substance database of the IFA , accessed on March 12, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g Entry on Octene. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2014.
^ Yadu B. Tewari, Michele M. Miller, Stanley P. Wasik, Daniel E. Martire: "Aqueous Solubility and Octanol / Water Partition Coefficient of Organic Compounds at 25 ° C"; in: J. Chem. Eng. Data , 1982 , 27 , pp. 451-454 ( doi : 10.1021 / je00030a025 ).
↑ Kenneth C. Bachman: "Relation of Luminometer Number to Molecular Structure and Smoke Point"; in: J. Chem. Eng. Data , 1961 , 6 , pp. 631-634 ( doi : 10.1021 / je60011a045 ).
↑ Desty, DH; Whyman, BHF: Application of Gas-Liquid Chromatography to Analysis of Liquid Petroleum Fractions ; in: Anal. Chem. 29 (1957) pp. 320-329, doi : 10.1021 / ac60123a001 .
↑ Forziati, AF; Camin, DL; Rossini, FD: Density, refractive index, boiling point, and vapor pressure of eight monoolefin (1-alkenes), six pentadiene, and two cyclomonoolefin hydrocarbons ; in: J. Res. NBS 45 (1950) pp. 406-410, doi : 10.6028 / jres.045.044 , pdf .
↑ Tsonopoulos, C .; Ambrose, D .: Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons ; in: J. Chem. Eng. Data 41 (1996) pp. 645-656, doi : 10.1021 / je9501999 .
↑ Dean, JA: Lange's Handbook of Chemistry , 15th Ed. 1999, McGraw-Hill, Inc. New York, ISBN 0-07-016384-7 .
↑ ^a ^b E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on 1-octene in the GESTIS substance database of the IFA , accessed on March 12, 2019(JavaScript required) .

[Römpp-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Octene. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2014.

[3] Yadu B. Tewari, Michele M. Miller, Stanley P. Wasik, Daniel E. Martire: "Aqueous Solubility and Octanol / Water Partition Coefficient of Organic Compounds at 25 ° C"; in: J. Chem. Eng. Data , 1982 , 27 , pp. 451-454 ( doi : 10.1021 / je00030a025 ).

[4] Kenneth C. Bachman: "Relation of Luminometer Number to Molecular Structure and Smoke Point"; in: J. Chem. Eng. Data , 1961 , 6 , pp. 631-634 ( doi : 10.1021 / je60011a045 ).

[Desty-5] Desty, DH; Whyman, BHF: Application of Gas-Liquid Chromatography to Analysis of Liquid Petroleum Fractions ; in: Anal. Chem. 29 (1957) pp. 320-329, doi : 10.1021 / ac60123a001 .

[Forziati-6] Forziati, AF; Camin, DL; Rossini, FD: Density, refractive index, boiling point, and vapor pressure of eight monoolefin (1-alkenes), six pentadiene, and two cyclomonoolefin hydrocarbons ; in: J. Res. NBS 45 (1950) pp. 406-410, doi : 10.6028 / jres.045.044 , pdf .

[Tsonopoulos-7] Tsonopoulos, C .; Ambrose, D .: Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons ; in: J. Chem. Eng. Data 41 (1996) pp. 645-656, doi : 10.1021 / je9501999 .

[Dean-8] Dean, JA: Lange's Handbook of Chemistry , 15th Ed. 1999, McGraw-Hill, Inc. New York, ISBN 0-07-016384-7 .

[Brandes-9] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.