Propene

From Wikipedia, the free encyclopedia
  (Redirected from Propylene)
Jump to: navigation, search
Not to be confused with propane.
"Propylene" redirects here. For the unrelated compound referred to as "propolene", see glucomannan.
Propene
Skeletal formula of propene Propene-2D-flat.png
Propylene.png Propylene
Identifiers
CAS number 115-07-1 YesY
PubChem 8252
ChemSpider 7954 YesY
UN number 1077
In Liquefied petroleum gas: 1075
KEGG C11505 YesY
ChEBI CHEBI:16052 YesY
ChEMBL CHEMBL117213 YesY
RTECS number UC6740000
Jmol-3D images Image 1
Image 3
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 (−301.4 °F; 88.0 K)
Boiling point −47.6 °C (−53.7 °F; 225.6 K)
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
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −108 °C (−162 °F; 165 K)
Related compounds
Related alkenes Ethylene
Isomers of Butylene
Related compounds Propane, Propyne
Propadiene, 1-Propanol
2-Propanol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.

Properties[edit]

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.

Occurrence in nature[edit]

Propene is found in nature and is a byproduct of vegetation and fermentation processes. Propene has been detected in trace amounts in the lower atmosphere of Titan.[2] On September 30, 2013 NASA announced that the Cassini orbiter space craft, part of the Cassini-Huygens mission, had discovered small amounts of naturally occurring propene in the atmosphere of Titan (moon) using spectroscopy.[3]

Production[edit]

Propene is produced from fossil fuelspetroleum, 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 naphtha cracking intended to produce ethylene, but it also results from refinery cracking producing other products.[4] 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%.[4]

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.[5]

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 propene.[5] Propene 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 propene and by-product hydrogen. The propene from propane yield is about 85 m%. Reaction by-products (mainly hydrogen) are usually used as fuel for the propane dehydrogenation reaction. As a result, propene 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.[6] 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.[7] The propane dehydrogenation process may be accomplished through different commercial technologies. The main differences between each of them concerns the catalyst employed, design of the reactor and strategies to achieve higher conversion rates.[8]

Methanol-to-Olefins/Methanol-to-Propene converts synthesis gas (syngas) to methanol, and then converts the methanol to ethylene and/or propene. 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 propene plant.[9]

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 propene and other light products. A high severity FCC unit is usually fed with gas oils (paraffins) and residues, and produces about 20–25 m% propene 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 propene 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.[10][11] Total world production of propene is currently about half that of ethylene.

Uses[edit]

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.[12]

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.[13]

Reactions[edit]

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.

Propene will react with NBS (N-Bromo Succinide) to form the allyl halide 2-bromo-propene (CH2=CH-CH2Br). The use of NBS, instead of hydrobromic acid, allows the substitution of hydrogen from the methyl functional group adjacent to the double bond, instead of the addition of hydrogen and bromide to the double bond as stated above in a hydrohalogenation reaction.

Environmental safety[edit]

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.[4]

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.[4]

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.[4]

Storage and handling[edit]

Since propene is volatile and flammable, precautions must be taken to avoid fire hazards in the handling of the gas. If propene is loaded to any equipment capable of causing ignition, such equipment should be shut down while loading, unloading, connecting or disconnecting. Propene is usually stored as liquid under pressure, although it is also possible to store it safely as gas at ambient temperature in approved containers.[14]

Pharmacology[edit]

Propene acts as a central nervous system depressant via allosteric agonism of the GABAA receptor. Excessive exposure may result in sedation and amnesia, progressing to coma and death in a mechanism equivalent to benzodiazepine overdose. Intentional inhalation may also result in death via asphyxiation (sudden inhalant death).

See also[edit]

References[edit]

  1. ^ Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers, 2005
  2. ^ "Cassini finds ingredient of household plastic on Saturn moon". Spacedaily.com. Retrieved 2013-11-12. 
  3. ^ "Spacecraft finds propylene on Saturn moon, Titan". UPI.com. 2013-09-30. Retrieved 2013-11-12. 
  4. ^ a b c d e "Product Safety Assessment(PSA): Propylene". Dow Chemical Co. 
  5. ^ a b "Propylene Production via Metathesis, Technology Economics Program". by Intratec, ISBN 978-0-615-61145-7, Q2 2012. 
  6. ^ Ashford’s Dictionary of Industrial Chemicals, Third edition, 2011, ISBN 978-0-9522674-3-0, pages 7766-9
  7. ^ by Giovanni Maggini (2012-06-28). "Technology Economics: Propylene via Propane Dehydrogenation". Slideshare.net. Retrieved 2013-11-12. 
  8. ^ by Giovanni Maggini (2013-04-17). "Technology Economics: Propylene via Propane Dehydrogenation, Part 3". Slideshare.net. Retrieved 2013-11-12. 
  9. ^ by Giovanni Maggini (2012-05-31). "Technology Economics: Propylene from Methanol". Slideshare.net. Retrieved 2013-11-12. 
  10. ^ http://www.petrochemistry.net Accessed August 2008
  11. ^ Organic Chemistry 6th edition, McMurry,J., Brooks/Cole Publishing, Pacific Grove USA (2005)
  12. ^ "Market Study: Propylene, Ceresana Research, February 2011". ceresana.com. Retrieved 2011-02-13. 
  13. ^ Budavari, Susan, ed. (1996). "8034. Propylene". The Merck Index, Twelfth Edition. New Jersey: Merck & Co. pp. 1348–1349 
  14. ^ Encyclopedia of Chemical Technology, Fourth edition, 1996, ISBN 0471-52689-4 (v.20), page 261