Propene

Structural formula
General
Surname	Propene
other names	Propylene; R-1270;
Molecular formula	C 3 H 6
Brief description	colorless, odorless gas
External identifiers / databases
EC number	204-062-1
ECHA InfoCard	100.003.693
PubChem	8252
Wikidata	Q151324
properties
Molar mass	42.08 g mol −1
Physical state	gaseous
density	1.91 kg m −3 (0 ° C, 1013 hPa) ; 0.609 kg l −1 at the boiling point
Melting point	−185.3 ° C
boiling point	−47.7 ° C
Vapor pressure	1.02 M Pa (20 ° C); 1.31 M Pa (30 ° C); 2.07 M Pa (50 ° C);
solubility	slightly soluble in water (384 mg l −1 , 20 ° C, 0.1 MPa)
Dipole moment	0.366 D (1.22 * 10 -30 C * m )
Refractive index	1.3567 (−70 ° C)
safety instructions
H and P phrases	H: 220-280
	P: 210-377-381-403
MAK	Switzerland: 10,000 ml m −3 or 17,500 mg m −3
Thermodynamic properties
ΔH f 0	20.0 kJ / mol
	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

Propene [ propene ] ( propylene [ propylene ]) is a colorless combustible gas . It is obtained by thermal cracking ( steam cracking ) of the light petroleum produced during the processing of crude oil .

Extraction and presentation

Steam cracking

Propene is mainly synthesized by steam cracking longer-chain alkanes (C ₅ -C ₁₀ ):

Propane dehydration (PDH)

Alternatively, propene can be prepared by thermal-catalytic treatment of propane with elimination of hydrogen :

This process is used by BASF Sonatrach in Tarragona , among others .

The main propane dehydrogenation process is UOP's Oleflex process , on which 55% of global capacity is based. In it, a propane-containing gas is preheated to 600–700 ° C and dehydrogenated in a fluidized bed dehydrogenation reactor over a platinum catalyst with aluminum oxide as the carrier.

Further procedures

Propene can also be obtained from ethylene and butenes by olefin metathesis or from methanol ( methanol-to-propylene ) using the Mobil process .

properties

Chemical properties

In water propene is only slightly soluble; the gas is flammable. Due to its double bond , propene is an unsaturated hydrocarbon and therefore tends to undergo addition reactions , including with hydrogen and halogens .

Examples:

Propene reacts with bromine to form 1,2-dibromopropane :

Propene reacts with hydrogen to form propane :

So that the addition reaction can take place, z. B. platinum , or palladium catalysts are used.

The (acid-catalyzed) addition of water produces 2-propanol :

Hexafluoropropene is the fully fluorinated form of propene.

By polymerization of propene widespread produced thermoplastic plastic polypropylene .

Safety-related parameters

Propene forms highly flammable mixtures with air. The explosion range is between 1.8% by volume (32 g / m ³ ) as the lower explosion limit (LEL) and 11.2% by volume (200 g / m ³ ) as the upper explosion limit (UEL).) The maximum explosion pressure is 9.4 bar. The limit gap width was determined to be 0.91 mm. This results in an assignment to explosion group IIA. The ignition temperature is 485 ° C. The substance therefore falls into temperature class T1.

use

Propene is used as a gas for flame cutting and the like and is a refrigerant in industrial refrigeration systems (R-1270). Furthermore, it is one of the most important raw materials in the chemical industry and is used to manufacture secondary products such as:

Approximately two thirds of the propene is used to make polypropylene. The next largest areas of application are the production of acrylonitrile, which is primarily used for the manufacture of acrylic textile fibers, and propylene oxide, which is used as a raw material for products such as polyurethane, paints and adhesives, polyester resins, coolants, antifreeze and solvents. Around 5 percent of propene is used to produce phenol and acetone in the cumene hydroperoxide process .

safety instructions

Propene is not very toxic, but has a narcotic and suffocating effect at high concentrations . Since propene has a greater density than air and is flammable, easily explosive mixtures form with air, as the propene collects near the ground.

Accidents with propene

In the Los Alfaques tanker truck accident on July 11, 1978, a tank truck loaded with 23 tons of propene burst south of Sant Carles de la Ràpita (Tarragona province, Spain). The propene spilled over the neighboring Los Alfaques campsite and caught fire there. In this accident, 217 people were killed and over 300 injured, some seriously.

On July 2, 2013, a goods tanker with propene gas derailed in Düsseldorf . An explosion could be prevented. There were no dead or injured.

In the Hitrino railway accident in Bulgaria, a freight train loaded with liquefied propene derailed and exploded on December 10, 2016, killing several people and destroying dozens of buildings.

Web links

Wiktionary: Propene - explanations of meanings, word origins, synonyms, translations

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on propene in the GESTIS substance database of the IFA , accessed on July 27, 2017(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Permittivity (Dielectric Constant) of Gases, pp. 6-188.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-442.
↑ Entry on propene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 115-07-1 or propene ), accessed on November 2, 2015.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.
↑ BASF Sonatrach PropanChem
^ UOP Light Olefin Solutions for Propylene and Ethylene Production
↑ Patent EP1824803 : Process for the production of propene from propane. Registered on December 8, 2005 , published on June 10, 2009 , applicant: BASF, inventor: Götz-Peter Schindler, Sven Crone, Otto Machhammer. ‌
↑ Jeffrey S. Plotkin: The Propylene Gap: How Can It Be Filled? , September 14, 2015.
↑ ^a ^b ^c ^d E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ Ceresana Research: Propylene market study , January 2011.
↑ rp-online.de: Kesselwaggon derailed in Düsseldorf: Dangerous goods accident paralyzes rail traffic ( memento of July 5, 2013 in the Internet Archive ), July 2, 2013.
^ Theguardian.com: Several killed as Bulgarian freight train derails and explodes , accessed on December 11, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on propene in the GESTIS substance database of the IFA , accessed on July 27, 2017(JavaScript required) .

[CRC90_6_188-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Permittivity (Dielectric Constant) of Gases, pp. 6-188.

[CRC90_3_442-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-442.

[CLP_100.003.693-4] Entry on propene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 115-07-1 or propene ), accessed on November 2, 2015.

[CRC90_5_24-6] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.

[7] BASF Sonatrach PropanChem

[8] UOP Light Olefin Solutions for Propylene and Ethylene Production

[9] Patent EP1824803 : Process for the production of propene from propane. Registered on December 8, 2005 , published on June 10, 2009 , applicant: BASF, inventor: Götz-Peter Schindler, Sven Crone, Otto Machhammer. ‌

[10] Jeffrey S. Plotkin: The Propylene Gap: How Can It Be Filled? , September 14, 2015.

[Brandes-11] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[12] Ceresana Research: Propylene market study , January 2011.

[13] rp-online.de: Kesselwaggon derailed in Düsseldorf: Dangerous goods accident paralyzes rail traffic ( memento of July 5, 2013 in the Internet Archive ), July 2, 2013.

[theguardian.com-14] Theguardian.com: Several killed as Bulgarian freight train derails and explodes , accessed on December 11, 2016.