Not to be confused with propane.
"Propylene" redirects here. For the unrelated compound referred to as "propolene", see glucomannan.
| Propene |
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| Identifiers |
| CAS number |
115-07-1 Y |
| PubChem |
8252 |
| ChemSpider |
7954 Y |
| UN number |
1077
In Liquefied petroleum gas: 1075 |
| KEGG |
C11505 Y |
| ChEBI |
CHEBI:16052 Y |
| ChEMBL |
CHEMBL117213 Y |
| RTECS number |
UC6740000 |
| Jmol-3D images |
Image 1 |
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InChI=1S/C3H6/c1-3-2/h3H,1H2,2H3 Y
Key: QQONPFPTGQHPMA-UHFFFAOYSA-N Y
InChI=1/C3H6/c1-3-2/h3H,1H2,2H3
Key: QQONPFPTGQHPMA-UHFFFAOYAA
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| Properties |
| Molecular formula |
C3H6 |
| Molar mass |
42.08 g mol−1 |
| Appearance |
Colorless gas |
| Density |
1.81 kg/m3, gas (1.013 bar, 15 °C)
613.9 kg/m3, liquid |
| Melting point |
− 185.2 °C, 88 K, -301 °F
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| Boiling point |
− 47.6 °C, 226 K, -54 °F
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| Solubility in water |
0.61 g/m3 |
| Viscosity |
8.34 µPa·s at 16.7 °C |
| Structure |
| Dipole moment |
0.366 D (gas) |
| Hazards |
| MSDS |
External MSDS |
| R-phrases |
12 |
| S-phrases |
9-16-33 |
| Main hazards |
Highly flammable,
Asphyxiant |
| NFPA 704 |
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| Flash point |
−108 °C |
| Related compounds |
| Related groups |
Allyl, Propenyl |
| Related compounds |
Propane, Propyne
Propadiene, 1-Propanol
2-Propanol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Propene, also known as propylene or methylethylene, is an unsaturated organic compound having the chemical formula C3H6. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons.
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Contents
- 1 Properties
- 2 Production
- 3 Uses
- 4 Reactions
- 5 Environmental safety
- 6 Storage & Handling
- 7 References
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Properties
At room temperature and atmospheric pressure, propene is a gas, and as with many other alkenes, it is also colorless with a weak but unpleasant smell.[1]
Propene has a higher density and boiling point than ethylene due to its greater mass. It has a slightly lower boiling point than propane and is thus more volatile. It lacks strongly polar bonds, yet the molecule has a small dipole moment due to its reduced symmetry (its point group is Cs).
Propene has the same empirical formula as cyclopropane but their atoms are connected in different ways, making these molecules structural isomers.
Production
Propene is produced from fossil fuels—petroleum, natural gas, and, to a much lesser extent, coal. Propene is a byproduct of oil refining and natural gas processing. During oil refining, ethylene, propene, and other compounds are produced as a result of cracking larger hydrocarbon molecules to produce hydrocarbons more in demand. A major source of propene is cracking intended to produce ethylene, but it also results from refinery cracking producing other products.[2] Propene can be separated by fractional distillation from hydrocarbon mixtures obtained from cracking and other refining processes; refinery-grade propene is about 50 to 70%.[2]
A shift to lighter steam cracker feedstocks with relatively lower propene yields and reduced motor gasoline demand in certain areas has created an imbalance of supply and demand for propene, and on-purpose production methods are becoming increasingly significant.[3]
On-purpose propylene production technologies include:
Olefin metathesis, also known as disproportionation, is a reversible reaction between ethylene and butenes in which double bonds are broken and then reformed to form propylene.[3] Propylene yields of about 90 wt% are achieved. This option may also be used when there is no butene feedstock. In this case, part of the ethylene feeds an ethylene-dimerization unit that converts ethylene into butene.
Propane dehydrogenation converts propane into propylene and by-product hydrogen. The propylene from propane yield is about 85 wt%. Reaction by-products (mainly hydrogen) are usually used as fuel for the propane dehydrogenation reaction. As a result, propylene tends to be the only product, unless local demand exists for hydrogen. This route is popular in regions, such as the Middle East, where there is an abundance of propane from oil/gas operations.[4] In this region, the propane output is expected to be capable of supplying not only domestic needs, but also the demand from China, where many PDH projects are scheduled to go on stream. However, as natural gas offerings in the USA are significantly increasing due to the rising exploitation of shale gas, propane prices are decreasing. Chemical companies are already planning to establish PDH plants in the USA to take advantage of the low price raw material, obtained from shale gas. Numerous plants dedicated to propane dehydrogenation are currently under construction around the world. There are already five licensed technologies.[5]
Methanol-to-Olefins/Methanol-to-Propylene converts synthesis gas (syn-gas) to methanol, and then converts the methanol to ethylene and/or propylene. The process also produces water as by-product. Synthesis gas is produced from the reformation of natural gas or by the steam-induced reformation of petroleum products such as naphtha, or by gasification of coal. A large amount of methanol is required to make a world-scale ethylene and/or propylene plant.[6]
High Severity fluid catalytic cracking (FCC) uses traditional FCC technology under severe conditions (higher catalyst-to-oil ratios, higher steam injection rates, higher temperatures, etc.) in order to maximize the amount of propylene and other light products. A high severity FCC unit is usually fed with gas oils (paraffins) and residues, and produces about 20-25 wt% propylene on feedstock together with greater volumes of motor gasoline and distillate byproducts.
Olefins Cracking includes a broad range of technologies that catalytically convert large olefins molecules (C4-C8) into mostly propylene and small amounts of ethylene.
Propene production has remained static at around 35 million tonnes (Europe and North America only) from 2000 to 2008, but it has been increasing in East Asia, most notably Singapore and China.[7][8] Total world production of propene is currently about half that of ethylene.
Uses
Propene is the second most important starting product in the petrochemical industry after ethylene. It is the raw material for a wide variety of products. Manufacturers of the plastic polypropylene account for nearly two thirds of all demand. Polypropylene is, for example, needed for the production of films, packaging, caps and closures as well as for other applications. In the year 2008 the worldwide sales of propene reached a value of over 90 billion US dollars.[9]
Propene and benzene are converted to acetone and phenol via the cumene process. Propene is also used to produce isopropanol (propan-2-ol), acrylonitrile, propylene oxide (epoxypropane) and epichlorohydrin.[10]
Reactions
Propene resembles other alkenes in that it undergoes addition reactions relatively easily at room temperature. The relative weakness of its double bond (which is less strong than two single bonds) explains its tendency to react with substances that can achieve this transformation. Alkene reactions include: 1) polymerization, 2) oxidation, 3) halogenation and hydrohalogenation, 4) alkylation, 5) hydration, 6) oligomerization, and 7) hydroformylation.
Environmental safety
Propene is produced naturally by vegetation, particularly certain tree species. It is also a product of combustion, from forest fires and cigarette smoke to motor vehicle and aircraft exhaust. It is an impurity in some heating gases. Observed concentrations have been in the range of 0.1-4.8 parts per billion (ppb) in rural air, 4-10.5 ppb in urban air, and 7-260 ppb in industrial air samples.[2]
In the United States and some European countries a Threshold Limit Value of 500 parts per million (ppm) was established for occupational (8-hour time-weighted average) exposure. It is considered a volatile organic compound (VOC) and emissions are regulated by many governments, but it is not listed by the U.S. Environmental Protection Agency (EPA) as a hazardous air pollutant under the Clean Air Act. With a relatively short half-life, it is not expected to bioaccumulate.[2]
Propene has low acute toxicity from inhalation. Inhalation of the gas can cause anesthetic effects and at very high concentrations, unconsciousness. However, the asphyxiation limit for humans is about 10 times higher (23%) than the lower flammability level.[2]
Storage & Handling
Since propylene is volatile and flammable, precautions must be taken to avoid fire hazards in the handling of the gas. If propylene is loaded to any equipment capable of causing ignition, such equipment should be shut down while loading, unloading, connecting or disconnecting. Propylene is usually stored as liquid under pressure, although it is also possible to store it safely as gas at ambient temperature in approved containers.[11]
References
- ^ Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers, 2005
- ^ a b c d e "Product Safety Assessment(PSA): Propylene". Dow Chemical Co.. http://www.dow.com/productsafety/finder/pro.htm.
- ^ a b "Propylene Production via Metathesis, Technology Economics Program". by Intratec, ISBN 978-0-615-61145-7, Q2 2012. http://www.slideshare.net/intratec/propylene-production-via-metathesis.
- ^ Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, ISBN 978-0-9522674-3-0, pages 7766-9
- ^ http://www.slideshare.net/intratec/propylene-production-via-propane-dehydrogenation
- ^ http://www.slideshare.net/intratec/propylene-production-from-methanol
- ^ www.petrochemistry.net Accessed August 2008
- ^ Organic Chemistry 6th edition, McMurry,J., Brooks/Cole Publishing, Pacific Grove USA (2005)
- ^ "Market Study: Propylene, Ceresana Research, February 2011". ceresana.com. http://www.ceresana.com/en/market-studies/chemicals/propylene/. Retrieved 2011-02-13.
- ^ Budavari, Susan, ed. (1996). "8034. Propylene". The Merck Index, Twelfth Edition. New Jersey: Merck & Co.. pp. 1348–1349
- ^ Encyclopedia of Chemical Technology, Fourth edition, 1996, ISBN 0471-52689-4 (v.20), page 261
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Alkenes
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- Ethene ( C2H4 )
- Propene ( C3H6 )
- Butene ( C4H8 )
- Pentene ( C5H10 )
- Hexene ( C6H12 )
- Heptene ( C7H14 )
- Octene ( C8H16 )
- Nonene ( C9H18 )
- Decene ( C10H20 )
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Branches of chemistry
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| Physical chemistry |
- Chemical kinetics
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- Thermochemistry
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| Organic chemistry |
- Biochemistry
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| Inorganic chemistry |
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- List of biomolecules
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