PRODUCT IDENTIFICATION

H.S. CODE

CLASSIFICATION

Monomer, Diene, Hemiterpene

EXTRA NOTES

By-product of C5 fraction.
Used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers
Overall Carcinogenic Evaluation: Group 2B
UN1218 [Flammable liquid]

PHYSICAL AND CHEMICAL PROPERTIES

AUTOIGNITION

220 C

NFPA RATINGS

REFRACTIVE INDEX

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Isoprene

Google Scholar Search - Isoprene

Drug Information Portal (U.S. National Library of Medicine) - Isoprene

PubChem Compound Summary - Isoprene

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Isoprene

http://www.ebi.ac.uk/chebi/ -  Isoprene

http://www.ncbi.nlm.nih.gov/ -  Isoprene

Human Metabolome Database - Isoprene

Material Safety Data Sheet

http://ntp.niehs.nih.gov/
Use:The majority of isoprene produced commercially is used to make synthetic rubber (cis-polyisoprene), most of which is used to produce vehicle tires. The second- and third-largest uses are in the production of styrene-isoprene-styrene block polymers and butyl rubber (isobutene-isoprene copolymer) (IARC 1994).
Production:Isoprene is recovered as a by-product of thermal cracking of naphtha or gas oil from C5 streams (IARC 1994, NTP 1999a). The isoprene yield is about 2% to 5% of the ethylene yield. U.S. demand for isoprene grew 6.5% annually from 1985 to 1992 (NTP 1999a). In 1994, isoprene production in the United States was about 619 million pounds, almost 29% more than in 1992. Estimated isoprene production capacity for eight facilities was 598 million pounds in 1996, based on estimates of isoprene content of product stream available from ethylene production via heavy liquids. In 2009, isoprene was produced by 22 manufacturers worldwide, including 12 U.S. producers (SRI 2009), and was available from 23 suppliers, including 12 U.S. suppliers (ChemSources 2009). U.S. imports of isoprene (purity ¡Ã 95% by weight) increased from zero in 1989 to a peak of 144 million pounds in 2003. Imports declined to 19.6 million pounds in 2004, the lowest level since 1992, but remained near 32 million pounds from 2005 through 2008. During this period, U.S. exports of isoprene ranged from 7.9 million to 39.6 million pounds (in 2006) (USITC 2009). Reports filed from 1986 to 2002 under the U.S. Environmental Protection Agency¡¯s Toxic Substances Control Act Inventory Update Rule indicated that U.S. production plus imports of isoprene totaled 100 million to 500 million pounds (EPA 2004).

http://pages.towson.edu/
ISOPRENE AND TERPENES: Some of the most interesting naturally occurring compounds originate from 2-methyl-1,3-butadiene, otherwise known as isoprene, in plants; the isoprene itself is synthesized from acetate. Pyrophosphate esters of isoprene are the actual reagents for these construction projects; pyrophosphoric acid is an anhydride of phosphoric acid. isoprene isopentenyl pyrophosphate geranyl pyrophosphate ---> ---> squalene The isoprene units are always linked 1,4 and head-to-tail in terpenes (the preferred addition orientation even in mineral acid), but are often linked further in bizarre ways to produce rings. Oxygen functional groups are often included, as might be expected from hydrolysis of the pyrophosphate linkage. The diversity of compounds produced is amazing, but the pattern of one methyl group every fourth carbon reveals their origin. The simplest, monoterpenes, consist of 2 isoprene units. The stereoisomers of these simplest terpenes provide interesting illustrations of the stereospecificity of odor receptors; for example (+)-(S)-carvone is responsible for the odor of caraway and (-)-(R)-carvone the odor of spearmint.

Local:
Isoprene, derived from butadiene, is a monomer which contains two double bonds, and is readily polymerized.  It is a clear liquid; insoluble in water; soluble in many organic solvents; boiling at 34 C. It is used in the manufacture of polyisoprene synthetic rubbers and elastomers. Isoprene unit (CH₂=C(CH₃)-CH=CH₂) is abundant in nature. Natural rubber is a polymer of isoprene. Synthetic polyisoprene rubber is the similarity of natural resin. The term terpene refers to a class of naturally occurring compounds whose carbon skeletons are composed exclusively of isoprene. Terpenes are major components of natural resin and some biological compounds such as vitamins, carotenes and squalene. Isoprene monomer production is almost entirely from C5 fraction as a by-product and consumption is linked almost entirely to polyisoprene synthetic rubbers.

APPEARANCE

CONTENT

99.3% min

WATER

0.2% max

DIMER

0.3% max

PENTADIENE

100ppm max

ALKYNES

50ppm max

PARAFFINS

50ppm max

CYCLOPENTADIENE

10ppm max

SULFUR

5ppm max

TBC

100ppm (4-TERT-BUTYLCATECHOL)

TRANSPORTATION

1218

HAZARD OVERVIEW

May cause respiratory tract irritation. Causes eye and skin irritation. Extremely flammable liquid and vapor. Vapor may cause flash fire. Target Organs: Eyes, skin

GHS

Danger

PICTOGRAMS

HAZARD STATEMENTS

H224  Extremely flammable liquid and vapor
H312  Harmful in contact with skin
H341  Suspected of causing genetic defects
H350  May cause cancer
H412  Harmful to aquatic life with long lasting effects

PRECAUTIONARY STATEMENTS

P201  Obtain special instructions before use
P210  Keep away from heat/sparks/open flames/hot surfaces. - No smoking
P240  Ground/Bond container and receiving equipment
P243  Take precautionary measures against static discharge
P273  Avoid release to the environment
P280  Wear protective gloves/protective clothing/eye protection/face protection
P281  Use personal protective equipment as required
P302 + P352  IF ON SKIN: Wash with plenty of soap and water
P308 + P313  IF exposed or concerned: Get medical advice/attention
P403 + P235  Store in a well-ventilated place. Keep cool

F+ Extremely flammableT Toxic

RISK PHRASES

12  Extremely flammable
45  May cause cancer
52/53  Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
68  Possible risks of irreversible effects.

SAFETY PHRASES

53  Avoid exposure - obtain special instructions before use
45  In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible)
61  Avoid release to the environment. Refer to special instructions / safety data sheets.