2,2,4-Trimethylpentane

<h2 id="production">Production</h2>
<p>Isooctane is produced on a massive scale in the <a href="/facts/Petroleum/IQV0bHVd">petroleum</a> industry by alkylation of <a href="/facts/Isobutene/Bl5REcDx">isobutene</a> with <a href="/facts/Isobutane/Bd8H7rsH">isobutane</a>. This process is conducted in <a href="/facts/Alkylation_unit/CW0FUWv4">alkylation units</a> in the presence of <a href="/facts/Acid_catalyst/JkJ7LkT6">acid catalysts</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a>
</p>

<p>It can also be produced from <a href="/facts/Isobutylene/Bl5REcDx">isobutylene</a> by <a href="/facts/Dimer_(chemistry)/mU64PnEq">dimerization</a> using an <a href="/facts/Amberlyst/z6KwlG8K">Amberlyst</a> <a href="/facts/Catalyst/LPBS7TQC">catalyst</a> to produce a mixture of iso-octenes.  <a href="/facts/Hydrogenation/l7EzNSA7">Hydrogenation</a> of this mixture produces  2,2,4-trimethylpentane.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a>
</p>

<h2 id="history">History</h2>
<p><a href="/facts/Engine_knocking/k9rhaaYD">Engine knocking</a> is an unwanted process that can occur during high compression ratios in <a href="/facts/Internal_combustion_engine/Ju4BXzj0">internal combustion engines</a>. In 1926 Graham Edgar added different amounts of <a href="/facts/Heptane/jP4XjrBe"><i>n</i>-heptane</a> and 2,2,4-trimethylpentane to gasoline, and discovered that the knocking stopped when 2,2,4-trimethylpentane was added. This work was the origin of the <a href="/facts/Octane_rating/LqkAlYbq">octane rating</a> scale.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> Test motors using 2,2,4-trimethylpentane gave a certain performance that was standardized as 100 octane.  The same test motors, run in the same fashion, using heptane, gave a performance which was standardized as 0 octane.  All other compounds and blends of compounds then were graded against these two standards and assigned octane numbers.
</p>
<h2 id="safety">Safety</h2>
<p>In common with all hydrocarbons, 2,2,4-trimethylpentane is flammable.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a>
</p>
<h2 id="see-also">See also</h2>
<ul><li><a href="/facts/Oil_refinery/yeaW0UMv">Oil refinery</a></li>
<li><a href="/facts/Antiknock_agent/drJDnGLL">Antiknock agents</a></li></ul>

<h2 id="external-links">External links</h2>

Wikimedia Commons has media related to 2,2,4-Trimethylpentane.

<ul><li><a href="http://www.inchem.org/documents/icsc/icsc/eics0496.htm">International Chemical Safety Card 0496</a></li></ul>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>Werner Dabelstein; Arno Reglitzky; Andrea Schütze; Klaus Reders (2007). "Automotive Fuels". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_719.pub2. ISBN 978-3527306732. <a href="978-3527306732" target="_blank">978-3527306732</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>Richardson, KA; Wilmer, JL; Smith-Simpson, D; Skopek, TR (February 1986). "Assessment of the genotoxic potential of unleaded gasoline and 2,2,4-trimethylpentane in human lymphoblasts in vitro". Toxicology and Applied Pharmacology. 82 (2): 316–22. doi:10.1016/0041-008x(86)90207-3. PMID 3945956. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
<li id="fn:3"><p>Clayden, Jonathan (2005). Organic chemistry (Reprinted (with corrections). ed.). Oxford [u.a.]: Oxford Univ. Press. pp. 315. ISBN 978-0-19-850346-0. <a href="978-0-19-850346-0" target="_blank">978-0-19-850346-0</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li>
<li id="fn:4"><p>Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961. <a href="0471238961" target="_blank">0471238961</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li>
<li id="fn:5"><p>Dimerization of isobutylene, Amberlyst.com <a href="http://www.amberlyst.com/isooctane.htm" target="_blank">http://www.amberlyst.com/isooctane.htm</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li>
<li id="fn:6"><p>Fuels and lubricants handbook, Volume 1, George E. Totten, Steven R. Westbrook, Rajesh J. Shah, page 62 <a href="https://books.google.com/books?id=J_AkNu-Y1wQC&dq=Graham+Edgar+2%2C2%2C4-trimethylpentane&pg=PA62" target="_blank">https://books.google.com/books?id=J_AkNu-Y1wQC&dq=Graham+Edgar+2%2C2%2C4-trimethylpentane&pg=PA62</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li>
<li id="fn:7"><p>2,2,4-Trimethylpentane, Integrated Risk Information System, United States Environmental Protection Agency <a href="http://www.epa.gov/iris/subst/0614.htm" target="_blank">http://www.epa.gov/iris/subst/0614.htm</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li>
</ol>

2,2,4-Trimethylpentane open-in-new

2,2,4-Trimethylpentane