Propene- Wikipedia, the free encyclopedia 

Propene 

From Wikipedia, the free encyclopedia 

Propene, also known 

as propylene or 

methyletbylene, 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. 

Propene 

CAS 115-07-1 I 

number 

PubChem 8252 

ChemSpider 7954 I 

UN number I 077 

Propene 

IUPAC name 

Identifiers 

In Liquefied petroleum gas: 1075 

KEGG Ctt505 1 

ChEBI CHEB1:16052 1 

ChEMBL CHEMBL117213 1 

RTECS UC6740000 

number 

http://en.wikipedia.org/wiki/Propene 

H H, I H C 

\ I ' H C=C 

I \ 

H H 

Jmol-30 Image I (http://chemapps.stolaf.edu/jmol/jmol.php?modei=C%30CC) 

images Image 3 (http://chemapps.stolaf.edu/jmol/jmol.php?modei=CC%3DC) 

Molecular C3H6 

formula 

Molar mass 42.08 g mol- l 

Appearance Colorless gas 

SMILES 

InCh I 

Properties 

Density 1.81 kg/m3, gas (1.013 bar, 15 oq 

613.9 kg/m3, liquid 

Melting - 185.2 °C (-301.4 °F; 88.0 K) 

point 

Boiling - 47.6 oc (-53.7 °F; 225.6 K) 

point 
Propene - Wikipedia, the free encyclopedia http:/ /en. wikipedia.org/wiki/Propene 

Contents 

• l Properties 

Solubility in 0.61 g/m3 

water 

Viscosity 8.34 f.iPa·s at 16.7 oc 

Dipole 

moment 

0.366 D (gas) 

Structure 

Hazards 

MSDS External MSDS (http://www.praxair.com/-/media!North%20America 

/US/Documents 

/SDS/Propylene%20C3H6%20Safety%20Data%20Sheet%20SDS%20P4648.ashx) 

R-phrases 12 

S-phrases 9-16-33 

Main Highly flammable, 

hazards Asphyxiant 

NFPA 704 

Flash point -I 08 oc ( -162 °F; 165 K) 

Related 

alkenes; 

related 

groups 

Related 

Related compounds 

Ethylene, Isomers of Butylene; 

Allyl, Propenyl 

Propane, Propyne 

compounds Propadiene, !-Propanol 

2-Propanol 

Except where noted otherwise, data are given for materials in their standard state (at 25 oc 

(77 °F), I 00 kPa) 

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Infobox references 

• 2 Occurrence in nature 

• 3 Production 

• 4 Uses 

• 5 Reactions 

• 6 Environmental safety 

• 7 Storage and handling 

• 8 Pharmacology 

• 9 See also 
Propene- Wikipedia, the free encyclopedia http:/ /en. wikipediaorg/wi ki!Propene 

• I 0 References 

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.(l] 

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 C5). 

Propene has the same empirical formula as cyclopropane but their atoms are connected in different ways, 

making these molecules structural isomers. 

Occurrence in nature 

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 ofTitan.l21 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 ofTitan (moon) using spectroscopy.Pl 

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 naphtha cracking intended to produce ethylene, but it also results 

from refinery cracking producing other products.l41 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%.[41 

A shift to lighter steam cracker feedstocks with relatively lower propene yields and reduced motor gasoline 

demand in certain areas has reduced propene supply. 

On-purpose production methods are becoming increasingly significant.l5l On-purpose 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 propeneVl 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.f61 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 
Propene - Wikipedia, the free encyclopedia http:/ /en. wikipedia.orglwiki/Propene 

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.Pl 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-Oiefins/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.[JO][II ] 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 ofthe 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. ln the year 2008 the worldwide sales of propene reached a 

value of over 90 billion US dollars.[J 21 

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.[l 31 

Reactions 

Propene resembles other alkenes in that it undergoes addition reactions relatively easily at room temperature. 

The relative weakness of its double bond 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 samplesJ41 

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 
Propene - Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Propene 

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.l41 

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 Jevet.l41 

Storage and handling 

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.l141 

Pharmacology 

Propene acts as a central nervous system depressant via allosteric agonism of the GAB AA 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 

• Los Alfaques Disaster 

• Inhalant abuse 

• 2014 Kaohsiung gas explosions 

References 

I. " Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers, 2005 

2." "Cassini finds ingredient of household plastic on Saturn moon" (http://www.spacedaily.com/reports 

/Cassini_finds_ingredient_of_household_plastic_on_Saturn_moon_999.html). Spacedaily.com. Retrieved 

2013-11-12. 

3. ""Spacecraft finds propylene on Saturn moon, Titan" (http://www.upi.com/Science_News/2013/09/30/Cassinifinds-ingredient-of-h<>usehold-plastic-on-Saturn-moon/UPl-4288138057 1911 /). UP I. com. 20 13-09-30. Retrieved 

20 13-11 -12. 

4. 1\ abc de "Product Safety Assessment(PSA): Propylene" (http://www.dow.com/productsafety/finder/pro.htm). 

Dow Chemical Co. 

5. "a b "Propylene Production via Metathesis, Technology Economics Program" (http://www.slideshare.net/intratec 

/propylene-production-via-metathesis). by lntratec, ISBN 978-0-615-61145-7, Q2 2012. 

6. " Ashford's Dictionary of Industrial Chemicals, Third edition, 201 1, ISBN 978-0-9522674-3-0, pages 7766-9 

7. "by Giovanni Maggini (2012-06-28). "Technology Economics: Propylene via Propane Dehydrogenation" 

(http://www.slideshare.net/intratec/propylene-production-via-propane-dehydrogenation). Slideshare.net. Retrieved 

2013-11-12. 
Propene- Wikipedia, the free encyclopedia http://en.wikipedia.org/wiki/Propene 

8. /\ by Giovanni Maggini (20 13-04-17). "Technology Economics: Propylene via Propane Dehydrogenation, Part 3" 

(http://www.slideshare.net/intratec/technology-economics-propylene-via-propane-dehydrogenation-part-3). 

Slideshare.net. Retrieved 2013-Il -12. 

9. /\by Giovanni Maggini (20 12-05-31 ). "Technology Economics: Propylene from Methanol" 

(http://www.slideshare.net/intratec/propylene-production-from-methanol). Slideshare.net. Retrieved 2013-11-12. 

I 0. /\ http://www.petrochemistry.net Accessed August 2008 

II. /\Organic Chemistry 6th edition, McMuny,J., Brooks/Cole Publishing, Pacific Grove USA (2005) 

12. /\ "Market Study: Propylene, Ceresana Research, February 20 II" (http://www.ceresana.com/enlmarket-studies 

/chemicals/propylene/). 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 Chern ical Technology, Fourth edition, 1996, ISBN 0471-52689-4 (v.20), page 261 

Retrieved from "http://en.wikipedia.org/w/index.php?title=Propene&oldid=64 1880660" 

Categories: Alkenes Monomers Commodity chemicals Petrochemicals 

GABAA receptor positive allosteric modulators 

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