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Linseed oil
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<h2 id="structure-and-composition">Structure and composition</h2> <p>Linseed oil is a <a href="/facts/Triglyceride/BQmjv4A0">triglyceride</a>, like other fats. Linseed oil is distinctive for its unusually large amount of <a href="/facts/Alpha-linolenic_acid/8q795eSN">α-linolenic acid</a>, which oxidises in air. The fatty acids in a typical linseed oil are of the following types:<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> <ul><li>The triply unsaturated α-linolenic acid (51.9–55.2%),</li> <li>The saturated acids <a href="/facts/Palmitic_acid/wPvdsPHA">palmitic acid</a> (about 7%) and <a href="/facts/Stearic_acid/ajnXYFo9">stearic acid</a> (3.4–4.6%),</li> <li>The monounsaturated <a href="/facts/Oleic_acid/NeVuHTbe">oleic acid</a> (18.5–22.6%),</li> <li>The doubly unsaturated <a href="/facts/Linoleic_acid/E3zEMyb6">linoleic acid</a> (14.2–17%).</li></ul> <h2 id="drying-properties">Drying properties</h2> <p class="note">Main article: <a href="/facts/Drying_oil/pVoWIUvY">drying oil</a></p> <p>Having a high content of di- and tri-unsaturated <a href="/facts/Ester/FoUAIIw4">esters</a>, linseed oil is susceptible to polymerization reactions upon exposure to oxygen in air. This polymerization, which is called <a href="/facts/Autoxidation/2mY5fjvj">autoxidation</a>, results in the rigidification of the material.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> To prevent premature drying, linseed oil-based products (oil paints, putty) are stored in airtight containers. </p><p>Rags soaked with linseed oil pose fire hazard because they provide a large surface area for rapid <a href="/facts/Oxidation/Pyd5RVcj">oxidation</a>. The oxidation of linseed oil is <a href="/facts/Exothermic/gCuSvpa4">exothermic</a>, which may lead to <a href="/facts/Spontaneous_combustion/ULScfFt1">spontaneous combustion</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> In 1991, <a href="/facts/One_Meridian_Plaza/XxtGDLrN">One Meridian Plaza</a>, in <a href="/facts/Philadelphia/2bFFCCTU">Philadelphia</a>, was severely damaged in a fire, in which three firefighters perished, thought to be caused by rags soaked with linseed oil.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="applications">Applications</h2> <p>Most applications of linseed oil exploit its drying properties, i.e., the initial material is liquid or at least pliable and the aged material is rigid but not brittle. The water-repelling (hydrophobic) nature of the resulting <a href="/facts/Hydrocarbon/Dcg95Ju5">hydrocarbon</a>-based material is advantageous.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h3>Paint binder</h3> <p>Linseed oil is the carrier used in <a href="/facts/Oil_paint/YMgKMEaU">oil paint</a>. It can also be used as a painting medium, making oil paints more fluid, transparent and glossy. It is available in varieties such as cold-pressed, alkali-refined, sun-bleached, sun-thickened, and polymerised (stand oil). The introduction of linseed oil was a significant advance in the technology of oil painting. </p> <h3>Putty</h3> <p>Traditional glazing <a href="/facts/Putty/eNhqRU2v">putty</a>, consisting of a paste of <a href="/facts/Chalk/b6hepsNS">chalk</a> powder and linseed oil, is a sealant for glass windows that hardens within a few weeks of application and can then be painted over. The durability of putty is owed to the drying properties of linseed oil. </p> <h3>Wood finish</h3> <p>When used as a <a href="/facts/Wood_finishing/JraBr8US">wood finish</a>, linseed oil dries slowly and shrinks little upon hardening. A linseed oil finish is easily scratched and liquid water penetrates a linseed oil finish in mere minutes, and water vapour bypasses it almost completely.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> <a href="/facts/Garden_furniture/Gh51JjCv">Garden furniture</a> treated with linseed oil may develop <a href="/facts/Mildew/wVos4nxG">mildew</a>. Oiled wood may be yellowish and is likely to darken with age. Even though the oil feels dry to the touch, studies show linseed oil does not fully cure.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p><p>Linseed oil is a common finish for wooden items, though very fine finish may require months to obtain. Studies show the fatty-acid structure of linseed oil has problems cross-linking and oxidizing, frequently turning black.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> </p> <h3>Gilding</h3> <p>Boiled linseed oil is used as <a href="/facts/Sizing/bwdFfFp2">sizing</a> in traditional oil <a href="/facts/Gilding/Q109QPJs">gilding</a> to adhere sheets of gold leaf to a substrate (parchment, canvas, <a href="/facts/Armenian_bole/5KMsh6Cu">Armenian bole</a>, etc.). It has a much longer working time than water-based size and gives a firm smooth surface that is adhesive enough in the first 12–24 hours after application to cause the gold to attach firmly to the intended surface. </p> <h3>Linoleum</h3> <p>Linseed oil is used to bind wood dust, cork particles, and related materials in the manufacture of the floor covering <a href="/facts/Linoleum/FwhkazoR">linoleum</a>. After its invention in 1860 by <a href="/facts/Frederick_Walton/0n2eJSsG">Frederick Walton</a>, linoleum, or "lino" for short, was a common form of domestic and industrial floor covering from the 1870s until the 1970s, when it was largely replaced by <a href="/facts/Polyvinyl_chloride/9VkegJvr">PVC</a> ("vinyl") floor coverings.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> However, since the 1990s, linoleum is returning to favor, being considered more environmentally sound than PVC.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> Linoleum has given its name to the printmaking technique <a href="/facts/Linocut/BdhqHXyG">linocut</a>, in which a relief design is cut into the smooth surface and then inked and used to print an image. The results are similar to those obtained by <a href="/facts/Woodcut/fg45gSl6">woodcut</a> printing. </p> <h3>Nutritional supplement and food</h3> <p>Raw cold-pressed linseed oil – commonly known as flax seed oil in nutritional contexts – is easily oxidized, and rapidly becomes rancid, with an unpleasant <a href="/facts/Odour/WnCopMmH">odour</a>, unless <a href="/facts/Refrigeration/Bs8HHbYd">refrigerated</a>. Linseed oil is not generally recommended for use in cooking. In one study, the content of <a href="/facts/Alpha-linolenic_acid/8q795eSN"><i>alpha</i>-linolenic acid (ALA)</a> in whole flaxseeds did not decrease after heating the seeds to temperatures of up to 178 °C (352.4 °F) for one and a half hours.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> </p><p>Linseed oil is an <a href="/facts/Edible_oil/FwHp4QXg">edible oil</a> in demand as a <a href="/facts/Dietary_supplement/SHXNNxaS">dietary supplement</a>, as a source of <a href="/facts/%25CE%2591-linolenic_acid/8q795eSN">α-linolenic acid</a>, an <a href="/facts/Omega-3_fatty_acid/X72Ynqov">omega-3 fatty acid</a>. In parts of Europe, it is traditionally eaten with potatoes and <a href="/facts/Quark_(dairy_product)/6TNShLyc">quark</a>. </p><p>Food-grade flaxseed oil is cold-pressed, obtained without solvent extraction, in the absence of oxygen, and marketed as edible flaxseed oil. Fresh, refrigerated and unprocessed, linseed oil is used as a <a href="/facts/Nutritional_supplement/SHXNNxaS">nutritional supplement</a> and is a traditional European ethnic food, highly regarded for its nutty flavor. Regular flaxseed oil contains between 57% and 71% polyunsaturated fats (<a href="/facts/Alpha-linolenic_acid/8q795eSN">alpha-linolenic acid</a>, <a href="/facts/Linoleic_acid/E3zEMyb6">linoleic acid</a>).<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> Plant breeders have developed flaxseed with both higher ALA (70%)<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> and very low ALA content (< 3%).<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> The USFDA granted generally recognized as safe (GRAS) status for high alpha linolenic flaxseed oil.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> </p> <h4>Nutrient content</h4> <table><tbody><tr><th>Typical fatty acid content</th><th>% <a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a></th><th>% European<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a></th></tr><tr><td><a href="/facts/Palmitic_acid/wPvdsPHA">Palmitic acid</a></td><td>6.0</td><td>4.0–6.0</td></tr><tr><td><a href="/facts/Stearic_acid/ajnXYFo9">Stearic acid</a></td><td>2.5</td><td>2.0–3.0</td></tr><tr><td><a href="/facts/Arachidic_acid/elD7lYLx">Arachidic acid</a></td><td>0.5</td><td>0–0.5</td></tr><tr><td><a href="/facts/Palmitoleic_acid/aUrAYB0T">Palmitoleic acid</a></td><td>-</td><td>0–0.5</td></tr><tr><td><a href="/facts/Oleic_acid/NeVuHTbe">Oleic acid</a></td><td>19.0</td><td>10.0–22.0</td></tr><tr><td><a href="/facts/Eicosenoic_acid/dLdg3wfr">Eicosenoic acid</a></td><td>-</td><td>0–0.6</td></tr><tr><td><a href="/facts/Linoleic_acid/E3zEMyb6">Linoleic acid</a></td><td>24.1</td><td>12.0–18.0</td></tr><tr><td><a href="/facts/Alpha-linolenic_acid/8q795eSN">Alpha-linolenic acid</a></td><td>47.4</td><td>56.0–71.0</td></tr><tr><td>Other</td><td>0.5</td><td>-</td></tr></tbody></table> <p>Nutrition information from the Flax Council of Canada.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> </p><p>Per 1 tbsp (14 g) </p> <ul><li>Calories: 126</li> <li>Total <a href="/facts/Fatty_acid/JGg3erIu">fat</a>: 14 g</li> <li><a href="/facts/Omega-3/X72Ynqov">Omega-3</a>: 8 g</li> <li><a href="/facts/Omega-6/0o3n3dtL">Omega-6</a>: 2 g</li> <li><a href="/facts/Omega-9/fKjqu5po">Omega-9</a>: 3 g</li></ul> <p>Flax seed oil contains no significant amounts of protein, carbohydrates or fibre. </p> <h3>Comparison to other vegetable oils</h3> Properties of <a href="/facts/Vegetable_oil/70v8uQMH">vegetable oils</a><a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a>The nutritional values are expressed as percent (%) by mass of total fat.<table><tbody><tr><th rowspan="2">Type</th><th rowspan="2">Processingtreatment<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a></th><th rowspan="2"><a href="/facts/Saturated_fatty_acids/8pvw306D">Saturated</a>fatty acids</th><th colspan="2" rowspan="1"><a href="/facts/Monounsaturated_fatty_acids/87HcP11s">Monounsaturated</a>fatty acids</th><th colspan="4"><a href="/facts/Polyunsaturated_fatty_acids/hvHwC43j">Polyunsaturated</a>fatty acids</th><th rowspan="2"><a href="/facts/Smoke_point/5akKcjW8">Smoke point</a></th></tr><tr><th>Total<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a></th><th rowspan="1"><a href="/facts/Oleic_acid/NeVuHTbe">Oleic</a>acid(ω−9)</th><th>Total<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a></th><th><a href="/facts/Alpha-Linolenic_acid/8q795eSN">α-Linolenic</a>acid(ω−3)</th><th><a href="/facts/Linoleic_acid/E3zEMyb6">Linoleic</a>acid(ω−6)</th><th><a href="/facts/Fatty_acid_ratio_in_food/NKQnXYXr">ω−6:3ratio</a></th></tr><tr><td><a href="/facts/Avocado_oil/NS3HoMvA">Avocado</a><a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a></td><td></td><td>11.6</td><td>70.6</td><td>67.9</td><td>13.5</td><td>1</td><td>12.5</td><td>12.5:1</td><td>250 °C (482 °F)<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a></td></tr><tr><td><a href="/facts/Brazil_nut/eCSRJ3Vl">Brazil nut</a><a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a></td><td></td><td>24.8</td><td>32.7</td><td>31.3</td><td>42.0</td><td>0.1</td><td>41.9</td><td>419:1</td><td>208 °C (406 °F)<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a></td></tr><tr><td><a href="/facts/Rapeseed_oil/6KgzlLuc">Canola</a><a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a></td><td></td><td>7.4</td><td>63.3</td><td>61.8</td><td>28.1</td><td>9.1</td><td>18.6</td><td>2:1</td><td>204 °C (400 °F)<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a></td></tr><tr><td><a href="/facts/Coconut_oil/mULGkRTS">Coconut</a><a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a></td><td></td><td>82.5</td><td>6.3</td><td>6</td><td>1.7</td><td>0.019</td><td>1.68</td><td>88:1</td><td>175 °C (347 °F)<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a></td></tr><tr><td><a href="/facts/Corn_oil/eebVEq2J">Corn</a><a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a></td><td></td><td>12.9</td><td>27.6</td><td>27.3</td><td>54.7</td><td>1</td><td>58</td><td>58:1</td><td>232 °C (450 °F)<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a></td></tr><tr><td><a href="/facts/Cottonseed_oil/m1TpX35L">Cottonseed</a><a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a></td><td></td><td>25.9</td><td>17.8</td><td>19</td><td>51.9</td><td>1</td><td>54</td><td>54:1</td><td>216 °C (420 °F)<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a></td></tr><tr><td><a href="/facts/Cottonseed_oil/m1TpX35L">Cottonseed</a><a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a></td><td><a href="/facts/Hydrogenated_fat/WJfaYJlG">hydrogenated</a></td><td>93.6</td><td>1.5</td><td></td><td>0.6</td><td>0.2</td><td>0.3</td><td>1.5:1</td><td></td></tr><tr><td>Flaxseed/linseed<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a></td><td></td><td>9.0</td><td>18.4</td><td>18</td><td>67.8</td><td>53</td><td>13</td><td>0.2:1</td><td>107 °C (225 °F)</td></tr><tr><td><a href="/facts/Grape_seed_oil/nz49QCBT">Grape seed</a><a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a></td><td> </td><td>9.6</td><td>16.1</td><td>15.8 </td><td>69.9</td><td>0.10</td><td>69.6</td><td>very high</td><td>216 °C (421 °F)</td></tr><tr><td><a href="/facts/Hemp_oil/uY3rmcW7">Hemp seed</a><a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a></td><td></td><td>7.0</td><td>9.0</td><td>9.0</td><td>82.0</td><td>22.0</td><td>54.0</td><td>2.5:1</td><td>166 °C (330 °F)<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a></td></tr><tr><td><a href="/facts/Safflower_oil/ntdyFrxu">High-oleic safflower oil</a><a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a></td><td></td><td>7.5</td><td>75.2</td><td>75.2</td><td>12.8</td><td>0</td><td>12.8</td><td>very high</td><td>212 °C (414 °F)<a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a></td></tr><tr><td><a href="/facts/Olive_oil/ae1Qnt2I">Olive</a> (extra virgin)<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a></td><td></td><td>13.8</td><td>73.0</td><td>71.3</td><td>10.5</td><td>0.7</td><td>9.8</td><td>14:1</td><td>193 °C (380 °F)<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a></td></tr><tr><td><a href="/facts/Palm_oil/n8zHXqoG">Palm</a><a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a></td><td></td><td>49.3</td><td>37.0</td><td>40</td><td>9.3</td><td>0.2</td><td>9.1</td><td>45.5:1</td><td>235 °C (455 °F)</td></tr><tr><td><a href="/facts/Palm_oil/n8zHXqoG">Palm</a><a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a></td><td>hydrogenated</td><td>88.2</td><td>5.7</td><td></td><td>0</td><td></td><td></td><td></td><td></td></tr><tr><td><a href="/facts/Peanut_oil/TJoTgDfN">Peanut</a><a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a></td><td></td><td>16.2</td><td>57.1</td><td>55.4</td><td>19.9</td><td>0.318</td><td>19.6</td><td>61.6:1</td><td>232 °C (450 °F)<a class="footnote-ref" id="fnref:48" href="#fn:48"><sup>48</sup></a></td></tr><tr><td><a href="/facts/Rice_bran_oil/RCk9UbaC">Rice bran oil</a></td><td></td><td>25</td><td><i>38.4</i></td><td>38.4</td><td><i>36.6</i></td><td>2.2</td><td>34.4<a class="footnote-ref" id="fnref:49" href="#fn:49"><sup>49</sup></a></td><td>15.6:1</td><td>232 °C (450 °F)<a class="footnote-ref" id="fnref:50" href="#fn:50"><sup>50</sup></a></td></tr><tr><td><a href="/facts/Sesame_oil/3jLjqRnN">Sesame</a><a class="footnote-ref" id="fnref:51" href="#fn:51"><sup>51</sup></a></td><td></td><td>14.2</td><td>39.7</td><td>39.3</td><td>41.7</td><td>0.3</td><td>41.3</td><td>138:1</td><td></td></tr><tr><td><a href="/facts/Soybean_oil/I9NzorzT">Soybean</a><a class="footnote-ref" id="fnref:52" href="#fn:52"><sup>52</sup></a></td><td></td><td>15.6</td><td>22.8</td><td>22.6</td><td>57.7</td><td>7</td><td>51</td><td>7.3:1</td><td>238 °C (460 °F)<a class="footnote-ref" id="fnref:53" href="#fn:53"><sup>53</sup></a></td></tr><tr><td><a href="/facts/Soybean_oil/I9NzorzT">Soybean</a><a class="footnote-ref" id="fnref:54" href="#fn:54"><sup>54</sup></a></td><td>partially hydrogenated</td><td>14.9</td><td>43.0</td><td>42.5</td><td>37.6</td><td>2.6</td><td>34.9</td><td>13.4:1</td><td></td></tr><tr><td><a href="/facts/Sunflower_oil/WIxPvWz8">Sunflower</a><a class="footnote-ref" id="fnref:55" href="#fn:55"><sup>55</sup></a></td><td></td><td>8.99</td><td>63.4</td><td>62.9</td><td>20.7</td><td>0.16</td><td>20.5</td><td>128:1</td><td>227 °C (440 °F)<a class="footnote-ref" id="fnref:56" href="#fn:56"><sup>56</sup></a></td></tr><tr><td><a href="/facts/Walnut_oil/RoG9Inqy">Walnut oil</a><a class="footnote-ref" id="fnref:57" href="#fn:57"><sup>57</sup></a></td><td>unrefined</td><td>9.1</td><td>22.8</td><td>22.2</td><td>63.3</td><td>10.4</td><td>52.9</td><td>5:1</td><td>160 °C (320 °F)<a class="footnote-ref" id="fnref:58" href="#fn:58"><sup>58</sup></a></td></tr></tbody></table> <h3>Additional uses</h3> <ul><li>Animal care products</li> <li><a href="/facts/Bicycle/nxBVrlBF">Bicycle</a> maintenance as a thread fixative, rust inhibitor and lubricant</li> <li><a href="/facts/Composition_ornament/33KuJzmx">Composition ornament</a> for moulded decoration</li> <li><a href="/facts/Earthen_floor/4p4rAvWj">Earthen floors</a></li> <li><a href="/facts/Fodder/b4Hw0Lq0">Animal feeds</a></li> <li>Industrial <a href="/facts/Lubricant/9PXISDwU">lubricant</a></li> <li><a href="/facts/Leather/kvQtwHPH">Leather</a> treatment</li> <li><a href="/facts/Oilcloth/SRKhnBA9">Oilcloth</a></li> <li><a href="/facts/Particle_detector/rYj0qKtA">Particle detectors</a><a class="footnote-ref" id="fnref:59" href="#fn:59"><sup>59</sup></a></li> <li><a href="/facts/Textile/PJrVeM5S">Textiles</a></li> <li><a href="/facts/Wood_preservation/eLLDnkbE">Wood preservation</a> (including as an active ingredient of <a href="/facts/Danish_oil/T4wve4x5">Danish oil</a>)</li> <li><a href="/facts/Seasoning_(cookware)/hXykQGXj">Cookware seasoning</a></li> <li>Plant protection<a class="footnote-ref" id="fnref:60" href="#fn:60"><sup>60</sup></a></li></ul> <h2 id="modified-linseed-oils">Modified linseed oils</h2> <h3>Stand oil</h3> <p>Stand oil is generated by heating linseed oil near 300 °C for a few days in the complete absence of air. Under these conditions, the polyunsaturated fatty esters convert to conjugated <a href="/facts/Diene/F5NxrLPW">dienes</a>, which then undergo <a href="/facts/Diels-Alder_reaction/zc6dVpKl">Diels-Alder reactions</a>, leading to crosslinking. The product, which is highly viscous, gives highly uniform coatings that "dry" to more elastic coatings than linseed oil itself. <a href="/facts/Soybean_oil/I9NzorzT">Soybean oil</a> can be treated similarly, but converts more slowly. On the other hand, <a href="/facts/Tung_oil/mqz1xtkf">tung oil</a> converts very quickly, being complete in minutes at 260 °C. Coatings prepared from stand oils are less prone to yellowing than are coatings derived from the parent oils.<a class="footnote-ref" id="fnref:61" href="#fn:61"><sup>61</sup></a> </p> <h3>Boiled linseed oil</h3> <p>Boiled linseed oil is a combination of raw linseed oil, stand oil (see above), and metallic <a href="/facts/Oil_drying_agent/WkAFXuT3">oil drying agents</a> (catalysts to accelerate drying).<a class="footnote-ref" id="fnref:62" href="#fn:62"><sup>62</sup></a> In the <a href="/facts/Medieval_era/RqzEKB9v">Medieval era</a>, linseed oil was boiled with <a href="/facts/Lead_oxide/NT1AxDpu">lead oxide</a> (litharge) to give a product called boiled linseed oil.<a class="footnote-ref" id="fnref:63" href="#fn:63"><sup>63</sup></a> The lead oxide forms lead "soaps" (lead oxide is <a href="/facts/Alkaline/s6NqPGSP">alkaline</a>) that promote hardening (polymerisation) of linseed oil by reaction with atmospheric oxygen. Heating shortens its drying time. </p> <h3>Raw linseed oil</h3> <p>Raw linseed oil is the base oil, unprocessed and without driers or thinners. It is mostly used as a feedstock for making a boiled oil. It does not cure sufficiently well or quickly to be regarded as a <a href="/facts/Drying_oil/pVoWIUvY">drying oil</a>.<a class="footnote-ref" id="fnref:64" href="#fn:64"><sup>64</sup></a> Raw linseed is sometimes used for <a href="/facts/Cricket_bat/6hphjcuU">oiling cricket bats</a> to increase surface friction for better ball control.<a class="footnote-ref" id="fnref:65" href="#fn:65"><sup>65</sup></a> It was also used to treat <a href="/facts/Belt_(mechanical)/k2zQ5tGv">leather flat belt drives</a> to reduce slipping. </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Danish_oil/T4wve4x5">Danish oil</a></li> <li><a href="/facts/Flax/rm28CMyJ">Flax seed</a></li> <li><a href="/facts/National_Linseed_Oil_Trust/GR9WJfR5">National Linseed Oil Trust</a></li> <li><a href="/facts/Smoke_point/5akKcjW8">Smoke point</a></li></ul> <h2 id="further-reading">Further reading</h2> <ul><li>Knight, William A.; Mende, William R. (2000). <a href="https://web.archive.org/web/20130530042026/http://www.thealchemist.us/alchemist1_005.htm"><i>Staining and Finishing for Muzzleloading Gun Builders</i></a>. privately published. Archived from <a href="http://www.thealchemist.us/alchemist1_005.htm">the original</a> on 2013-05-30.</li></ul> <h2 id="external-links">External links</h2> Wikimedia Commons has media related to Linseed oil. <ul><li><a href="https://en.wikisource.org/wiki/Collier%27s_New_Encyclopedia_(1921)/Linseed_Oil">"Linseed Oil" </a>. <i><a href="/facts/Collier%2527s_Encyclopedia/0t2uzTCK">Collier's New Encyclopedia</a></i>. 1921.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Jones, Frank N. (2003). "Alkyd Resins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_409. 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>Vereshchagin, A. G.; Novitskaya, Galina V. (1965). "The triglyceride composition of linseed oil". Journal of the American Oil Chemists' Society. 42 (11): 970–974. doi:10.1007/BF02632457. PMID 5898097. S2CID 29785363. <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>Poth, Ulrich (2001). "Drying Oils and Related Products". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_055. ISBN 9783527303854. <a href="9783527303854" target="_blank">9783527303854</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Ettling, Bruce V.; Adams, Mark F. (1971). "Spontaneous combustion of linseed oil in sawdust". Fire Technology. 7 (3): 225. doi:10.1007/BF02590415. S2CID 109500727. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Routley, J. 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