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Diethyl ether
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<h2 id="production">Production</h2> <p>Most diethyl ether is produced as a byproduct of the vapor-phase <a href="/facts/Hydration_reaction/T1Vb2u1d">hydration</a> of <a href="/facts/Ethylene/QMNBYLYn">ethylene</a> to make <a href="/facts/Ethanol/3lCLfBSP">ethanol</a>. This process uses solid-supported <a href="/facts/Phosphoric_acid/l6NbwyCv">phosphoric acid</a> <a href="/facts/Catalysis/LPBS7TQC">catalysts</a> and can be adjusted to make more ether if the need arises:<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> Vapor-phase <a href="/facts/Dehydration_reaction/dTAxlyRX">dehydration</a> of ethanol over some <a href="/facts/Aluminium_oxide/wXM9P6pI">alumina</a> catalysts can give diethyl ether yields of up to 95%.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> 2 CH3CH2OH → (CH3CH2)2O + H2O <p>Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="uses">Uses</h2> <p>The dominant use of diethyl ether is as a solvent. One particular application is in the production of cellulose plastics such as <a href="/facts/Cellulose_acetate/sBnBCBb1">cellulose acetate</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h3>Laboratory solvent</h3> <p>It is a common solvent for the <a href="/facts/Grignard_reaction/DfhXQ6SG">Grignard reaction</a> in addition to other reactions involving organometallic reagents.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> These uses exploit its basicity. Diethyl ether is a popular non-polar solvent in <a href="/facts/Liquid-liquid_extraction/qVfck5T1">liquid-liquid extraction</a>. As an extractant, it is immiscible with and less <a href="/facts/Density/92p6hh9I">dense</a> than water. </p><p>Although immiscible, it has significant <a href="/facts/Solubility/kLE9h3Jb">solubility</a> in <a href="/facts/Water_(molecule)/FFsl65l1">water</a> (6.05 g/(100 ml) at 25 °C<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a>) and dissolves 1.5 g/(100 g) (1.0 g/(100 ml)) water at 25 °C.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> </p> <h3>Fuel</h3> <p>Diethyl ether has a high <a href="/facts/Cetane_number/jzmECJhV">cetane number</a> of 85–96 and, in combination with petroleum distillates for gasoline and diesel engines,<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> is used as a <a href="/facts/Starting_fluid/XxAbItyX">starting fluid</a> because of its high volatility and low <a href="/facts/Flash_point/97JQP35E">flash point</a>. Ether starting fluid is sold and used in countries with cold climates, as it can help with cold starting an engine at sub-zero temperatures. For the same reason it is also used as a component of the fuel mixture for <a href="/facts/Carbureted_compression_ignition_model_engine/Rde8KW8B">carbureted compression ignition model engines</a>. </p> <h2 id="chemical-reactions">Chemical reactions</h2> <p><a href="/facts/Triethyloxonium_tetrafluoroborate/bxIE4S28">Triethyloxonium tetrafluoroborate</a> is prepared from <a href="/facts/Boron_trifluoride/2qa0NIH8">boron trifluoride</a>, diethyl ether, and <a href="/facts/Epichlorohydrin/pouNHADT">epichlorohydrin</a>:<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> </p> 4 Et2O·BF3 + 2 Et2O + 3 C2H3OCH2Cl → 3 [Et3O]+[BF4]− + B(OCH(CH2Cl)CH2OEt)3 <p>Diethyl ether is a common laboratory <a href="/facts/Polar_aprotic_solvent/LoMPMz8S">aprotic solvent</a>. It is susceptible to the formation of <a href="/facts/Hydroperoxide/w7hdgtVF">hydroperoxides</a>. </p> <h2 id="metabolism">Metabolism</h2> <p>A <a href="/facts/Cytochrome_P450/alxusFD0">cytochrome P450</a> enzyme is proposed to metabolize diethyl ether.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> </p><p>Diethyl ether inhibits <a href="/facts/Alcohol_dehydrogenase/XWwHgyad">alcohol dehydrogenase</a>, and thus slows the metabolism of <a href="/facts/Ethanol/3lCLfBSP">ethanol</a>.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> It also inhibits metabolism of other drugs requiring <a href="/facts/Oxidative_metabolism/kb6gpsvL">oxidative metabolism</a>. For example, <a href="/facts/Diazepam/h7lIGqkM">diazepam</a> requires hepatic oxidization whereas its oxidized metabolite <a href="/facts/Oxazepam/UGeD4Utb">oxazepam</a> does not.<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> </p> <h2 id="safety-stability-regulations">Safety, stability, regulations</h2> <p>Diethyl ether is extremely flammable and may form explosive vapour/air mixtures.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> </p><p>Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources. Ether will ignite if exposed to an open flame, though due to its high flammability, an open flame is not required for ignition. Other possible ignition sources include – but are not limited to – hot plates, steam pipes, heaters, and electrical arcs created by switches or outlets.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> Vapour may also be ignited by the static electricity which can build up when ether is being poured from one vessel into another. The autoignition temperature of diethyl ether is 160 °C (320 °F). The diffusion of diethyl ether in air is 9.18 × 10−6 m2/s (298 K, 101.325 kPa). </p><p>Ether is sensitive to light and air, tending to form explosive <a href="/facts/Diethyl_ether_peroxide/l9kJ34Vb">peroxides</a>.<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> Ether peroxides have a higher boiling point than ether and are contact explosives when dry.<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> Commercial diethyl ether is typically supplied with trace amounts of the <a href="/facts/Antioxidant/4TG4MQ83">antioxidant</a> <a href="/facts/Butylated_hydroxytoluene/Td6ctev7">butylated hydroxytoluene</a> (BHT), which reduces the formation of peroxides. Storage over <a href="/facts/Sodium_hydroxide/xjtdYtq7">sodium hydroxide</a> precipitates the intermediate ether hydroperoxides. Water and peroxides can be removed by either distillation from <a href="/facts/Sodium/eYuSPu2V">sodium</a> and <a href="/facts/Benzophenone/U1dDfM9k">benzophenone</a>, or by passing through a column of <a href="/facts/Activated_alumina/z2PNLrbS">activated alumina</a>.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> </p><p>Due to its application in the manufacturing of illicit substances, it is listed in the Table II precursor under the <a href="/facts/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances/DIes6dB8">United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances</a> as well as substances such as <a href="/facts/Acetone/cVyJxKqw">acetone</a>, <a href="/facts/Toluene/Pzdt8dwD">toluene</a> and <a href="/facts/Sulfuric_acid/Wom6fymJ">sulfuric acid</a>.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> </p> <h2 id="history">History</h2> <p>The compound may have been synthesised by either <a href="/facts/J%C4%81bir_ibn_Hayy%C4%81n/qUTxy4kA">Jābir ibn Hayyān</a> in the 8th century<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> or <a href="/facts/Ramon_Llull/MnK265Y1">Ramon Llull</a> in 1275.<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a><a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a> It was synthesised in 1540 by <a href="/facts/Valerius_Cordus/HLbAXdyB">Valerius Cordus</a>, who called it "sweet oil of vitriol" (<i>oleum dulce vitrioli</i>) – the name reflects the fact that it is obtained by distilling a mixture of <a href="/facts/Ethanol/3lCLfBSP">ethanol</a> and <a href="/facts/Sulfuric_acid/Wom6fymJ">sulfuric acid</a> (then known as oil of vitriol) – and noted some of its <a href="/facts/Medicinal_properties/InK1lB9l">medicinal properties</a>.<a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> At about the same time, <a href="/facts/Paracelsus/U6H7KEUs">Paracelsus</a> discovered the <a href="/facts/Analgesic/xLj4XBcq">analgesic</a> properties of the molecule in dogs.<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> The name <i>ether</i> was given to the substance in 1729 by <a href="/facts/August_Sigmund_Frobenius/R7n1Ppku">August Sigmund Frobenius</a>.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> </p><p>It was considered to be a sulfur compound until the idea was disproved in about 1800.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> </p><p>The synthesis of diethyl ether by a reaction between <a href="/facts/Ethanol/3lCLfBSP">ethanol</a> and <a href="/facts/Sulfuric_acid/Wom6fymJ">sulfuric acid</a> has been known since the 13th century.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> </p> <h3>Anesthesia</h3> <p><a href="/facts/William_T._G._Morton/JDNS1NBu">William T. G. Morton</a> participated in a public demonstration of ether anesthesia on October 16, 1846, at the <a href="/facts/Ether_Dome/1CEq6BYv">Ether Dome</a> in <a href="/facts/Boston,_Massachusetts/exjfn6xf">Boston, Massachusetts</a>. Morton had called his ether preparation, with aromatic oils to conceal its smell, "<i>Letheon</i>" after the <a href="/facts/Lethe/vXsAzMpT">Lethe River</a> (Λήθη, meaning "forgetfulness, oblivion").<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> However, <a href="/facts/Crawford_Williamson_Long/cVgtFrqD">Crawford Williamson Long</a> is now known to have demonstrated its use privately as a <a href="/facts/General_anesthetic/YNM2tqty">general anesthetic</a> in surgery to officials in Georgia, as early as March 30, 1842, and Long publicly demonstrated ether's use as a surgical anesthetic on six occasions before the Boston demonstration.<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a><a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a><a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> Diethyl ether was preferred by some practitioners over <a href="/facts/Chloroform/gvzuJMXa">chloroform</a> as a general anesthetic due to ether's more favorable <a href="/facts/Therapeutic_index/h311pqE5">therapeutic index</a>, that is, a greater difference between an effective dose and a potentially toxic dose.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> </p><p>Diethyl ether does not depress the <a href="/facts/Myocardium/oMqU4Sdu">myocardium</a> but rather it stimulates the sympathetic nervous system leading to hypertension and tachycardia. It is safely used in patients with shock as it preserves the <a href="/facts/Baroreflex/PuVw15ba">baroreceptor reflex</a>.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a> Its minimal effect on myocardial depression and respiratory drive, as well as its low cost and high therapeutic index allows it to see continued use in developing countries.<a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> Diethyl ether could also be mixed with other anesthetic agents such as <a href="/facts/Chloroform/gvzuJMXa">chloroform</a> to make <a href="/facts/C.E._mixture/opkUXNkF">C.E. mixture</a>, or chloroform and <a href="/facts/Ethanol/3lCLfBSP">alcohol</a> to make <a href="/facts/A.C.E._mixture/opkUXNkF">A.C.E. mixture</a>. In the 21st century, ether is rarely used. The use of flammable ether was displaced by nonflammable fluorinated hydrocarbon anesthetics. <a href="/facts/Halothane/PQ58E6ah">Halothane</a> was the first such anesthetic developed and other currently used inhaled anesthetics, such as <a href="/facts/Isoflurane/mWv7ku8s">isoflurane</a>, <a href="/facts/Desflurane/jo4eubpY">desflurane</a>, and <a href="/facts/Sevoflurane/rzRREcGA">sevoflurane</a>, are halogenated ethers.<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects.<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> </p> <p>Prior to 2005, it was on the <a href="/facts/World_Health_Organization%27s_List_of_Essential_Medicines/6kmu81Xm">World Health Organization's List of Essential Medicines</a> for use as an anesthetic.<a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a><a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a> </p> <h3>Medicine</h3> <p>Ether was once used in pharmaceutical formulations. A mixture of alcohol and ether, one part of diethyl ether and three parts of ethanol, was known as <a href="/facts/Compound_spirit_of_ether/A7BpmwPR">"Spirit of ether"</a>, Hoffman's <a href="/facts/Anodyne/VbEDUdRY">Anodyne</a> or Hoffman's Drops. In the United States this concoction was removed from the <a href="/facts/United_States_Pharmacopeia/CyYDYG8m">Pharmacopeia</a> at some point prior to June 1917,<a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a> as a study published by <a href="/facts/William_Procter,_Jr./ofUevXb7">William Procter, Jr.</a> in the <i>American Journal of Pharmacy</i> as early as 1852 showed that there were differences in formulation to be found between commercial manufacturers, between international <a href="/facts/Pharmacopoeia/CCNj7RSM">pharmacopoeia</a>, and from Hoffman's original recipe.<a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a> It is also used to treat <a href="/facts/Hiccups/dTyQsvSn">hiccups</a> through instillation into the nasal cavity.<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a> </p> <h3>Recreational abuse</h3> <p class="note">See also: <a href="/facts/Ether_addiction/TfUTLDqC">Ether addiction</a></p> <p>The recreational use of ether also took place at organised parties in the 19th century called <a href="/facts/History_of_general_anesthesia/3RVnDgJC">ether frolics</a>, where guests were encouraged to inhale therapeutic amounts of diethyl ether or <a href="/facts/Nitrous_oxide/Jvys91lI">nitrous oxide</a>, producing a state of excitation. Long, as well as fellow dentists <a href="/facts/Horace_Wells/EM8QWoQ9">Horace Wells</a>, William Edward Clarke, and <a href="/facts/William_T._G._Morton/JDNS1NBu">William T. G. Morton</a>, observed that during these gatherings, people would often experience minor injuries but appear to show no reaction to them, nor memory that it had happened, demonstrating ether's anaesthetic effects.<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a> </p><p>In the 19th and early 20th centuries, ether drinking was popular among Polish peasants.<a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a> It is a traditional and still relatively popular recreational drug among <a href="/facts/Lemkos/t0U3XPGo">Lemkos</a>.<a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a> It is usually consumed in a small quantity (<i>kropka</i>, or "dot") poured over milk, sugar water, or orange juice in a <a href="/facts/Shot_glass/VANQ5QzX">shot glass</a>. As a drug, it has been known to cause <a href="/facts/Psychological_dependence/9M3oLRP5">psychological dependence</a>, sometimes referred to as <a href="/facts/Etheromania/TfUTLDqC">etheromania</a>.<a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a>[<i>medical citation needed</i>] </p><p>Ether intoxication is referenced in <a href="/facts/Hunter_S._Thompson/J5sgub5C">Hunter S. Thompson</a>'s <i><a href="/facts/Fear_and_Loathing_in_Las_Vegas/0cA17xXc">Fear and Loathing in Las Vegas</a></i>, where in one of the book's most famous quotes, protagonist Raoul Duke declares that "There is nothing in the world more helpless and irresponsible and depraved than a man in the depths of an ether binge."<a class="footnote-ref" id="fnref:48" href="#fn:48"><sup>48</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/The_Great_Moment_(1944_film)/PK511RJt"><i>The Great Moment</i></a> – film about William T.G. Morton and ether</li> <li><a href="/facts/Flurothyl/FFNs7sEy">Flurothyl</a> – fluorinated derivative</li></ul> <h2 id="explanatory-notes">Explanatory notes</h2> <h2 id="external-links">External links</h2> Wikimedia Commons has media related to Diethyl ether. <ul><li><a href="http://journals.lww.com/anesthesiology/Abstract/1992/10000/Michael_Faraday_and_His_Contribution_to_Anesthesia.27.aspx">Michael Faraday's announcement of ether as an anesthetic in 1818</a> <a href="https://web.archive.org/web/20110522040512/http://journals.lww.com/anesthesiology/Abstract/1992/10000/Michael_Faraday_and_His_Contribution_to_Anesthesia.27.aspx">Archived</a> 2011-05-22 at the <a href="/facts/Wayback_Machine/nmQ3a6JC">Wayback Machine</a></li> <li>Calculation of <a href="http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Diethyl%20ether">vapor pressure</a>, <a href="http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Diethyl%20ether">liquid density</a>, <a href="http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Diethyl%20ether">dynamic liquid viscosity</a>, <a href="http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Diethyl%20ether">surface tension</a> of diethyl ether, ddbonline.ddbst.de</li> <li><a href="https://www.cdc.gov/niosh/npg/npgd0277.html">CDC – NIOSH Pocket Guide to Chemical Hazards</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Et stands for monovalent ethyl group CH3CH2 which is often written as C2H5 (see pseudoelement symbol) <a href="/wiki/Ethyl_group" target="_blank">/wiki/Ethyl_group</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Sakuth, Michael; Mensing, Thomas; Schuler, Joachim; Heitmann, Wilhelm; Strehlke, Günther; Mayer, Dieter (2010). "Ethers, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_023.pub2. ISBN 978-3-527-30385-4. <a href="978-3-527-30385-4" target="_blank">978-3-527-30385-4</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>"Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2004. <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Ethyl Ether, Chem. Economics Handbook. Menlo Park, Calif: SRI International. 1991. <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Cohen, Julius Berend (1920). A Class-book of Organic Chemistry, Volume 1. London: Macmillan and Co. p. 39. the structure of ethyl alcohol cohen julius diethyl ether. <a href="https://archive.org/details/aclassbookorgan00cohegoog" target="_blank">https://archive.org/details/aclassbookorgan00cohegoog</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>"Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2004. <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Moyer, W. W.; Marveltitle=Triethyl Carbinol, C. S. (1931). "Triethyl Carbinol". Organic Syntheses. 11: 98. doi:10.15227/orgsyn.011.0098. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Merck Index, 10th ed., Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, p. 551 <a href="/wiki/Merck_Index" target="_blank">/wiki/Merck_Index</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>H. H. Rowley; Wm. R. Reed (1951). "Solubility of Water in Diethyl Ether at 25 °". J. Am. Chem. Soc. 73 (6): 2960. Bibcode:1951JAChS..73.2960R. doi:10.1021/ja01150a531. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>"Extra Strength Starting Fluid: How it Works". Valvovine. Archived from the original on 2007-09-27. Retrieved 2007-09-05. <a href="https://web.archive.org/web/20070927222427/http://www.valvoline.com/pages/products/product_detail.asp?product=38§ion=402" target="_blank">https://web.archive.org/web/20070927222427/http://www.valvoline.com/pages/products/product_detail.asp?product=38§ion=402</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>H. Meerwein (1966). "Triethyloxonium fluoroborate". Organic Syntheses. 46: 113. doi:10.15227/orgsyn.046.0113. <a href="/wiki/Organic_Syntheses" target="_blank">/wiki/Organic_Syntheses</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>109. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript. Archived 2017-09-17 at the Wayback Machine Matthew P. Brown and Gary A. 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