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href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fw%2Findex.php%3Ftitle%3DCarbon_disulfide%26action%3Dedit%26undo%3D1248742839%26undoafter%3D1241436744"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q243354" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> </div> <div id="contentSub"><div id="mw-content-subtitle">← <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">Carbon disulfide</a></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-undo-success"><div class="mw-parser-output"> <style data-mw-deduplicate="TemplateStyles:r1238441935">.mw-parser-output .fmbox{clear:both;margin:0.2em 0;width:100%;border:1px solid #a2a9b1;background-color:var(--background-color-interactive-subtle,#f8f9fa);box-sizing:border-box;color:var(--color-base,#202122)}.mw-parser-output .fmbox-warning{border:1px solid #bb7070;background-color:#ffdbdb}.mw-parser-output .fmbox-editnotice{background-color:transparent}.mw-parser-output .fmbox .mbox-text{border:none;padding:0.25em 0.9em;width:100%}.mw-parser-output .fmbox .mbox-image{border:none;padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .fmbox .mbox-imageright{border:none;padding:2px 0.9em 2px 0;text-align:center}.mw-parser-output .fmbox .mbox-invalid-type{text-align:center}@media screen{html.skin-theme-clientpref-night .mw-parser-output .fmbox-warning{background-color:#300}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .fmbox-warning{background-color:#300}}</style><table id="mw-undo-success" class="plainlinks fmbox fmbox-editnotice" role="presentation"><tbody><tr><td class="mbox-text"><div> <p><b>You are about to <a href="/wiki/Help:Reverting" title="Help:Reverting">undo</a> an edit.</b> Please check the comparison below to verify that this is what you want to do, then publish the changes below to finish undoing the edit. </p><p><i>If you are undoing an edit that is not <a href="/wiki/Wikipedia:Vandalism" title="Wikipedia:Vandalism">vandalism</a>, explain the reason in the edit summary. Do not use the default message only.</i> </p> </div></td></tr></tbody></table> </div></div><p>You do not have permission to edit this page, for the following reasons: </p> <ul class="permissions-errors"><li class="mw-permissionerror-blockedtext"> <div id="mw-blocked-text" style="border: 1px solid #AAA; background-color: var(--background-color-warning-subtle, ivory); color: inherit; padding: 1.5em; width: 100%; box-sizing: border-box;"> <div style="text-align: center;"><span style="font-size: 26px;"><span typeof="mw:File"><a href="/wiki/File:Stop_hand_nuvola.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/f/f1/Stop_hand_nuvola.svg/50px-Stop_hand_nuvola.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f1/Stop_hand_nuvola.svg/75px-Stop_hand_nuvola.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f1/Stop_hand_nuvola.svg/100px-Stop_hand_nuvola.svg.png 2x" data-file-width="240" data-file-height="240" /></a></span><b> This IP address has been <a href="/wiki/Wikipedia:Blocking_policy" title="Wikipedia:Blocking policy">blocked</a> from <i>editing</i> Wikipedia.</b></span><br /><span style="font-size: 18px;">This does not affect your ability to <i>read</i> Wikipedia pages.</span></div><div class="paragraphbreak" style="margin-top:0.5em"></div><b>Most people who see this message have done nothing wrong.</b> Some kinds of blocks restrict editing from specific service providers or telecom companies in response to recent abuse or vandalism, and can sometimes affect other users who are unrelated to that abuse. Review the information below for assistance if you do not believe that you have done anything wrong.<div class="paragraphbreak" style="margin-top:0.5em"></div> <p>The IP address or range 8.222.128.0/17 has been <a href="/wiki/Wikipedia:Blocking_policy" title="Wikipedia:Blocking policy">blocked</a> by <a href="/wiki/User:L235" title="User:L235">‪L235‬</a> for the following reason(s): </p> <div style="padding:10px; background:var(--background-color-base, white); color:inherit; border:1px #666 solid;"> <div class="user-block colocation-webhost" style="margin-bottom: 0.5em; background-color: #ffefd5; border: 1px solid #AAA; padding: 0.7em;"> <figure class="mw-halign-left" typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Server-multiple.svg/40px-Server-multiple.svg.png" decoding="async" width="40" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Server-multiple.svg/60px-Server-multiple.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Server-multiple.svg/80px-Server-multiple.svg.png 2x" data-file-width="744" data-file-height="1052" /></span><figcaption></figcaption></figure><b>The <a href="/wiki/IP_address" title="IP address">IP address</a> that you are currently using has been blocked because it is believed to be a <a href="/wiki/Web_hosting_service" title="Web hosting service">web host provider</a> or <a href="/wiki/Colocation_centre" title="Colocation centre">colocation provider</a>.</b> To prevent abuse, <a href="/wiki/Wikipedia:Open_proxies" title="Wikipedia:Open proxies">web hosts and colocation providers may be blocked</a> from editing Wikipedia. <div style="border-top: 1px solid #AAA; clear: both">You will not be able to edit Wikipedia using a web host or colocation provider because it hides your IP address, much like a <a href="/wiki/Wikipedia:Open_proxies" title="Wikipedia:Open proxies">proxy</a> or <a href="/wiki/Virtual_private_network" title="Virtual private network">VPN</a>. <p><b>We recommend that you attempt to use another connection to edit.</b> For example, if you use a proxy or VPN to connect to the internet, turn it off when editing Wikipedia. If you edit using a mobile connection, try using a Wi-Fi connection, and vice versa. If you are using a corporate internet connection, switch to a different Wi-Fi network. If you have a Wikipedia account, please log in. </p><p>If you do not have any other way to edit Wikipedia, you will need to <a href="/wiki/Wikipedia:IP_block_exemption#Requesting_and_granting_exemption" title="Wikipedia:IP block exemption">request an IP block exemption</a>. </p> <style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">How to appeal if you are confident that your connection does not use a colocation provider's IP address:</div><div class="hidden-content mw-collapsible-content" style=""> If you are confident that you are not using a web host, you may <a href="/wiki/Wikipedia:Appealing_a_block" title="Wikipedia:Appealing a block">appeal this block</a> by adding the following text on your <a href="/wiki/Help:Talk_pages" title="Help:Talk pages">talk page</a>: <code>{{<a href="/wiki/Template:Unblock" title="Template:Unblock">unblock</a>|reason=Caught by a colocation web host block but this host or IP is not a web host. My IP address is _______. <i>Place any further information here.</i> ~~~~}}</code>. <b>You must fill in the blank with your IP address for this block to be investigated.</b> Your IP address can be determined <span class="plainlinks"><b><a class="external text" href="https://en.wikipedia.org/wiki/Wikipedia:Get_my_IP_address?withJS=MediaWiki:Get-my-ip.js">here</a></b></span>. Alternatively, if you wish to keep your IP address private you can use the <a href="/wiki/Wikipedia:Unblock_Ticket_Request_System" title="Wikipedia:Unblock Ticket Request System">unblock ticket request system</a>. There are several reasons you might be editing using the IP address of a web host or colocation provider (such as if you are using VPN software or a business network); please use this method of appeal only if you think your IP address is in fact not a web host or colocation provider.</div></div> <p><span class="sysop-show" style="font-size: 85%;"><span style="border:#707070 solid 1px;background-color:#ffe0e0;padding:2px"><b>Administrators:</b></span> The <a href="/wiki/Wikipedia:IP_block_exemption" title="Wikipedia:IP block exemption">IP block exemption</a> user right should only be applied to allow users to edit using web host in exceptional circumstances, and requests should usually be directed to the functionaries team via email. If you intend to give the IPBE user right, a <a href="/wiki/Wikipedia:CheckUser" title="Wikipedia:CheckUser">CheckUser</a> needs to take a look at the account. This can be requested most easily at <a href="/wiki/Wikipedia:SPI#Quick_CheckUser_requests" class="mw-redirect" title="Wikipedia:SPI">SPI Quick Checkuser Requests</a>. <b>Unblocking</b> an IP or IP range with this template <b>is highly discouraged</b> without at least contacting the blocking administrator.</span> </p> </div></div> </div> <p>This block will expire on 18:23, 24 August 2026. Your current IP address is 8.222.208.146. </p> <div class="paragraphbreak" style="margin-top:0.5em"></div><div style="font-size: 16px;"> <p>Even when blocked, you will <i>usually</i> still be able to edit your <a href="/wiki/Special:MyTalk" title="Special:MyTalk">user talk page</a>, as well as <a href="/wiki/Wikipedia:Emailing_users" title="Wikipedia:Emailing users">email</a> administrators and other editors. </p> </div> <div class="paragraphbreak" style="margin-top:0.5em"></div><div style="font-size: 16px;"> <p>For information on how to proceed, please read the <b><a href="/wiki/Wikipedia:Appealing_a_block#Common_questions" title="Wikipedia:Appealing a block">FAQ for blocked users</a></b> and the <a href="/wiki/Wikipedia:Appealing_a_block" title="Wikipedia:Appealing a block">guideline on block appeals</a>. The <a href="/wiki/Wikipedia:Guide_to_appealing_blocks" title="Wikipedia:Guide to appealing blocks">guide to appealing blocks</a> may also be helpful. </p> </div> <p>Other useful links: <a href="/wiki/Wikipedia:Blocking_policy" title="Wikipedia:Blocking policy">Blocking policy</a> · <a href="/wiki/Help:I_have_been_blocked" title="Help:I have been blocked">Help:I have been blocked</a> </p> </div></li><li class="mw-permissionerror-globalblocking-blockedtext-range"> <div id="mw-blocked-text" style="border: 1px solid #AAA; background-color: var(--background-color-warning-subtle, ivory); color: inherit; padding: 1.5em; width: 100%; box-sizing: border-box;"> <div style="text-align: center;"><span style="font-size: 26px;"><span typeof="mw:File"><a href="/wiki/File:Stop_hand_nuvola.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/f/f1/Stop_hand_nuvola.svg/50px-Stop_hand_nuvola.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f1/Stop_hand_nuvola.svg/75px-Stop_hand_nuvola.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f1/Stop_hand_nuvola.svg/100px-Stop_hand_nuvola.svg.png 2x" data-file-width="240" data-file-height="240" /></a></span><b> This IP address range has been <a href="https://meta.wikimedia.org/wiki/Global_blocks" class="extiw" title="m:Global blocks">globally blocked</a>.</b></span><br /><span style="font-size: 18px;">This does not affect your ability to <i>read</i> Wikipedia pages.</span></div><div class="paragraphbreak" style="margin-top:0.5em"></div><b>Most people who see this message have done nothing wrong.</b> Some kinds of blocks restrict editing from specific service providers or telecom companies in response to recent abuse or vandalism, and can sometimes affect other users who are unrelated to that abuse. 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Retrieved on 2024-10-23.</ref> | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|315|319|332|361fd|372}} | PPhrases = {{P-phrases|202|210|281|303+361+353|304+340+312|305+351+338|308+313}}<br/>[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc00/icsc0022.htm ICSC 0022] | NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 0 | FlashPtC = −43 | FlashPt_ref = <ref name="chemister" /> | AutoignitionPtC = 102 | AutoignitionPt_ref = <ref name="chemister" /> | ExploLimits = 1.3–50%<ref name="PGCH" /> | LD50 = 3188 mg/kg (rat, oral) | EyeHazard = Irritant | SkinHazard = Irritant | InhalationHazard = Irritant; neurotoxic | PEL = TWA 20 ppm C 30 ppm 100 ppm (30-minute maximum peak)<ref name="PGCH">{{PGCH|0104}}</ref> | REL = TWA 1 ppm (3 mg/m<sup>3</sup>) ST 10 ppm (30 mg/m<sup>3</sup>) [skin]<ref name="PGCH" /> | IDLH = 500 ppm<ref name="PGCH" /> | LC50 = >1670 ppm (rat, 1&nbsp;h)<br />15500 ppm (rat, 1&nbsp;h)<br />3000 ppm (rat, 4&nbsp;h)<br />3500 ppm (rat, 4&nbsp;h)<br />7911 ppm (rat, 2&nbsp;h)<br />3165 ppm (mouse, 2&nbsp;h)<ref name="IDLH">{{IDLH|75150|Carbon disulfide}}</ref> | LCLo = 4000 ppm (human, 30&nbsp;min)<ref name="IDLH" /> }} | Section8 = {{Chembox Related | OtherCompounds = [[Carbon dioxide]]<br />[[Carbonyl sulfide]]<br />[[Carbon diselenide]] }} }} '''Carbon disulfide''' (also spelled as '''carbon disulphide''') is an [[inorganic compound]] with the [[chemical formula]] {{chem2|CS2}} and [[Chemical structure|structure]] {{chem2|S\dC\dS}}. It is also considered as the anhydride of [[thiocarbonic acid]].<ref>{{Cite web |last=Informatics |first=NIST Office of Data and |title=Carbon disulfide |url=https://webbook.nist.gov/cgi/cbook.cgi?ID=C75150&Mask=80 |access-date=2024-05-07 |website=webbook.nist.gov |language=en}}</ref> It is a colorless, flammable, [[Neurotoxicity|neurotoxic]] liquid that is used as a building block in organic synthesis. Pure carbon disulfide has a pleasant, [[diethyl ether|ether]]- or [[chloroform]]-like odor, but commercial samples are usually yellowish and are typically contaminated with foul-smelling impurities.<ref name="Holleman">{{Holleman&Wiberg}}.</ref> == History == In 1796, the German chemist [[Wilhelm August Lampadius]] (1772–1842) first prepared carbon disulfide by heating [[pyrite]] with moist charcoal. He called it "liquid sulfur" (''flüssig Schwefel'').<ref>{{cite journal |last1=Lampadius |title=Etwas über flüssigen Schwefel, und Schwefel-Leberluft |journal=Chemische Annalen für die Freunde der Naturlehre, Arzneygelährtheit, Haushaltungskunst und Manufacturen (Chemical Annals for the Friends of Science, Medicine, Economics, and Manufactures)|date=1796 |issue=2 |pages=136–137 |url=https://books.google.com/books?id=gqk5AAAAcAAJ&pg=PA136 |trans-title=Something about liquid sulfur and liver-of-sulfur gas (i.e., hydrogen sulfide) |language=de}}</ref> The composition of carbon disulfide was finally determined in 1813 by the team of the Swedish chemist [[Jöns Jacob Berzelius]] (1779–1848) and the Swiss-British chemist [[Alexander Marcet]] (1770–1822).<ref>{{cite journal |last1=Berzelius |first1=J. |last2=Marcet |first2=Alexander |title=Experiments on the alcohol of sulphur, or sulphuret of carbon |journal=Philosophical Transactions of the Royal Society of London |date=1813 |volume=103 |pages=171–199 |doi=10.1098/rstl.1813.0026 |s2cid=94745906 |doi-access=free }}</ref> Their analysis was consistent with an [[empirical formula]] of CS<sub>2</sub>.<ref>(Berzelius and Marcet, 1813), p. 187.</ref> ==Occurrence, manufacture, properties== Small amounts of carbon disulfide are released by [[volcano|volcanic]] eruptions and [[marsh]]es. CS<sub>2</sub> once was manufactured by combining [[carbon]] (or [[Coke (fuel)|coke]]) and [[sulfur]] at 800–1000&nbsp;°C.<ref>{{cite journal | last=Warnecke | first=Friedrich | title=Die gewerbliche Schwefelkohlenstoffvergiftung | journal=Archiv für Gewerbepathologie und Gewerbehygiene | publisher=Springer Science and Business Media LLC | volume=11 | issue=2 | year=1941 | issn=0340-0131 | doi=10.1007/bf02122927 | pages=198–248 | bibcode=1941IAOEH..11..198W | s2cid=72106188 | language=de}}</ref> :C + 2S → CS<sub>2</sub> A lower-temperature reaction, requiring only 600&nbsp;°C, utilizes [[natural gas]] as the carbon source in the presence of [[silica gel]] or [[alumina]] [[catalyst]]s:<ref name="Holleman" /> :2 CH<sub>4</sub> + S<sub>8</sub> → 2 CS<sub>2</sub> + 4 H<sub>2</sub>S The reaction is analogous to the combustion of [[methane]]. Global production/consumption of carbon disulfide is approximately one million tonnes, with China consuming 49%, followed by India at 13%, mostly for the production of rayon fiber.<ref>{{cite web |url=http://www.ihs.com/products/chemical/planning/ceh/carbon-disulfide.aspx |title=Carbon Disulfide report from IHS Chemical |access-date= June 15, 2013 }}</ref> United States production in 2007 was 56,000 tonnes.<ref>{{cite web |url=http://www.icis.com/Articles/2008/09/08/9154319/chemical-profile-carbon-disulfide.html |title=Chemical profile: carbon disulfide from ICIS.com |access-date= June 15, 2013 }}</ref> ===Solvent=== Carbon disulfide can dissolve a variety of [[Chemical polarity#Nonpolar molecules|nonpolar]] chemicals including [[phosphorus]], sulfur, [[selenium]], [[bromine]], [[iodine]], [[fat]]s, [[resin]]s, [[rubber]], and [[Bitumen|asphalt]].<ref>{{cite web |url=http://www.akzonobel.com/sulfurderivatives/products/carbon_disulfide/ |title=Carbon Disulfide |publisher=Akzo Nobel |access-date=2010-12-16 |archive-date=2017-09-03 |archive-url=https://web.archive.org/web/20170903211829/https://www.akzonobel.com/sulfurderivatives/products/carbon_disulfide/ |url-status=dead }}</ref> === Extraterrestrial === In March 2024, traces of CS<sub>2</sub> were likely detected in the atmosphere of the temperate [[mini-Neptune]] planet [[TOI-270|TOI-270 d]] by the [[James Webb Space Telescope]].<ref >{{Citation |last1=Benneke |first1=Björn |title=JWST Reveals CH$_4$, CO$_2$, and H$_2$O in a Metal-rich Miscible Atmosphere on a Two-Earth-Radius Exoplanet |date=2024-03-05 |last2=Roy |first2=Pierre-Alexis |last3=Coulombe |first3=Louis-Philippe |last4=Radica |first4=Michael |last5=Piaulet |first5=Caroline |last6=Ahrer |first6=Eva-Maria |last7=Pierrehumbert |first7=Raymond |last8=Krissansen-Totton |first8=Joshua |last9=Schlichting |first9=Hilke E.|arxiv=2403.03325 }}</ref> ==Reactions== Combustion of CS<sub>2</sub> affords [[sulfur dioxide]] according to this ideal stoichiometry: :CS<sub>2</sub> + 3{{nbsp}}O<sub>2</sub> → CO<sub>2</sub> + 2{{nbsp}}SO<sub>2</sub> ===With nucleophiles=== For example, amines afford [[dithiocarbamate]]s:<ref name=":0">{{cite journal | last1=Yokoyama | first1=Masataka | last2=Imamoto | first2=Tsuneo | title=Organic Reactions of Carbon Disulfide | journal=Synthesis | publisher=Georg Thieme Verlag KG | volume=1984 | issue=10 | year=1984 | issn=0039-7881 | doi=10.1055/s-1984-30978 | pages=797–824}}</ref> :2{{nbsp}}R<sub>2</sub>NH + CS<sub>2</sub> → [R<sub>2</sub>NH<sub>2</sub><sup>+</sup>][R<sub>2</sub>NCS<sub>2</sub><sup>−</sup>] [[Xanthate]]s form similarly from [[alkoxide]]s:<ref name=":0"/> :RONa + CS<sub>2</sub> → [Na<sup>+</sup>][ROCS<sub>2</sub><sup>−</sup>] This reaction is the basis of the manufacture of regenerated [[cellulose]], the main ingredient of [[viscose]], [[rayon]], and [[cellophane]]. Both xanthates and the related [[thioxanthate]]s (derived from treatment of CS<sub>2</sub> with sodium [[thiolate]]s) are used as [[Froth flotation|flotation agents]] in mineral processing. Upon treatment with [[sodium sulfide]], carbon disulfide affords [[trithiocarbonate]]:<ref name=":0"/> :Na<sub>2</sub>S + CS<sub>2</sub> → [Na<sup>+</sup>]<sub>2</sub>[CS<sub>3</sub><sup>2−</sup>] Carbon disulfide does not hydrolyze readily, although the process is catalyzed by an [[enzyme]] [[carbon disulfide hydrolase]]. Compared to the [[Isoelectronicity|isoelectronic]] [[carbon dioxide]], CS<sub>2</sub> is a weaker [[electrophile]]. While, however, reactions of [[nucleophile]]s with CO<sub>2</sub> are highly reversible and products are only isolated with very strong nucleophiles, the reactions with CS<sub>2</sub> are thermodynamically more favored allowing the formation of products with less reactive nucleophiles.<ref>{{Cite journal|last1=Li|first1=Zhen|last2=Mayer|first2=Robert J.|last3=Ofial|first3=Armin R.| last4=Mayr|first4=Herbert|date=2020-04-27|title= From Carbodiimides to Carbon Dioxide: Quantification of the Electrophilic Reactivities of Heteroallenes|journal=Journal of the American Chemical Society|volume=142|issue=18|pages=8383–8402|doi=10.1021/jacs.0c01960|pmid=32338511|s2cid=216557447}}</ref> ===Reduction=== Reduction of carbon disulfide with [[sodium]] affords [[sodium 1,3-dithiole-2-thione-4,5-dithiolate]] together with sodium [[trithiocarbonate]]:<ref>{{cite journal|journal=Org. Synth.|year=1996|volume=73|page=270|doi=10.15227/orgsyn.073.0270|title=4,5-Dibenzoyl-1,3-dithiole-1-thione}}</ref> : 4{{nbsp}}Na + 4{{nbsp}}CS<sub>2</sub> → Na<sub>2</sub>C<sub>3</sub>S<sub>5</sub> + Na<sub>2</sub>CS<sub>3</sub> ===Chlorination=== [[Chlorination reaction|Chlorination]] of CS<sub>2</sub> provides a route to [[carbon tetrachloride]]:<ref name="Holleman" /> :CS<sub>2</sub> + 3 [[chlorine|Cl<sub>2</sub>]] → CCl<sub>4</sub> + [[disulfur dichloride|S<sub>2</sub>Cl<sub>2</sub>]] This conversion proceeds via the intermediacy of [[thiophosgene]], CSCl<sub>2</sub>. ===Coordination chemistry=== CS<sub>2</sub> is a ligand for many metal complexes, forming pi complexes. One example is [[Cyclopentadienyl complex|Cp]]Co([[hapticity|η<sup>2</sup>]]-CS<sub>2</sub>)(P[[Methyl group|Me]]<sub>3</sub>).<ref>{{cite journal |last=Werner |first=Helmut |title=Novel Coordination Compounds formed from CS<sub>2</sub> and Heteroallenes |journal=Coordination Chemistry Reviews |year=1982 |volume=43 |pages=165–185 |doi=10.1016/S0010-8545(00)82095-0 }}</ref> ==Polymerization== CS<sub>2</sub> polymerizes upon photolysis or under high pressure to give an insoluble material called car-sul or "Bridgman's black", named after the discoverer of the polymer, [[Percy Williams Bridgman]].<ref>{{cite journal |last1=Bridgman |first1=P.W. |title=Explorations toward the limit of utilizable pressures |journal=Journal of Applied Physics |date=1941 |volume=12 |issue=6 |pages=461–469|doi=10.1063/1.1712926 |bibcode=1941JAP....12..461B }}</ref> Trithiocarbonate (-S-C(S)-S-) linkages comprise, in part, the backbone of the polymer, which is a [[semiconductor]].<ref>{{cite journal |title=Carbon dioxide and carbon disulfide as resources for functional polymers |first1=Bungo |last1=Ochiai |first2=Takeshi |last2=Endo |journal=Progress in Polymer Science |volume=30 |issue=2 |pages=183–215 |doi=10.1016/j.progpolymsci.2005.01.005 |year=2005 }}</ref> ==Uses== The principal industrial uses of carbon disulfide, consuming 75% of the annual production, are the manufacture of [[viscose rayon]] and [[cellophane]] film.<ref name="Ullmann" /> It is also a valued intermediate in chemical synthesis of [[carbon tetrachloride]]. It is widely used in the synthesis of [[Organosulfur chemistry|organosulfur compounds]] such as [[xanthate]]s, which are used in [[froth flotation]], a method for extracting metals from their ores. Carbon disulfide is also a precursor to [[dithiocarbamates]], which are used as drugs (e.g. [[Metam sodium]]) and [[rubber chemistry]]. ===Niche uses=== [[File:Carbon disulfide insecticide ad, 1896 - The American elevator and grain trade (IA CAT31053470064) (page 3 crop).jpg|left|thumb|Carbon disulfide insecticide ad from the 1896 issue of ''The American Elevator and Grain Trade'' magazine]] It can be used in [[fumigation]] of airtight storage warehouses, airtight flat storage, bins, [[Grain elevator|grain elevators]], railroad [[Boxcar|box cars]], ship holds, [[Barge|barges]], and cereal mills.<ref>{{Greenwood&Earnshaw2nd|page=}}</ref> Carbon disulfide is also used as an [[insecticide]] for the fumigation of grains, nursery stock, in fresh fruit conservation, and as a [[soil disinfectant]] against insects and [[nematodes]].<ref>{{cite book |last1=Worthing |first1=Charles R. |last2=Hance |first2=Raymond J. |title=The Pesticide Manual, A World Compendium |publisher=British Crop Protection Council |year=1991 |edition=9th |isbn=9780948404429 |url-access=registration |url=https://archive.org/details/pesticidemanualw0000unse }}</ref> It can also be used for the [[Barking dog reaction]]. ==Health effects== Carbon disulfide has been linked to both [[Acute (medicine)|acute]] and chronic forms of [[poisoning]], with a diverse range of symptoms.<ref>{{Cite web|url=https://www.atsdr.cdc.gov/phs/phs.asp?id=472&tid=84#bookmark05|title=ATSDR - Public Health Statement: Carbon Disulfide|website=www.atsdr.cdc.gov|access-date=2020-01-17}}</ref> Concentrations of 500–3000&nbsp;mg/m<sup>3</sup> cause acute and subacute poisoning. These include a set of mostly neurological and psychiatric symptoms, called encephalopathia sulfocarbonica. Symptoms include acute [[psychosis]] (manic [[delirium]], [[hallucinations]]), [[paranoia|paranoic]] ideas, loss of appetite, gastrointestinal and sexual disorders, [[polyneuritis]], [[myopathy]], and mood changes (including irritability and anger). Effects observed at lower concentrations include neurological problems ([[encephalopathy]], psychomotor and psychological disturbances, [[polyneuritis]], abnormalities in nerve conduction), [[Hearing loss|hearing]] problems, vision problems (burning eyes, abnormal light reactions, increased [[intraocular pressure|ophthalmic pressure]]), heart problems (increased deaths for heart disease, [[angina pectoris]], [[hypertension|high blood pressure]]), reproductive problems (increased [[miscarriages]], [[Asthenozoospermia|immobile]] or [[Teratospermia|deformed]] sperm), and decreased immune response.<ref name="WHO">{{cite book |title=Air Quality Guidelines |date=2000 |publisher=WHO Regional Office for Europe, Copenhagen, Denmark |edition=2 |url=https://www.euro.who.int/__data/assets/pdf_file/0019/123058/AQG2ndEd_5_4carbodisulfide.PDF |access-date=31 July 2021 |chapter=Chapter 5.4 : Carbon disulfide |archive-date=18 October 2022 |archive-url=https://web.archive.org/web/20221018194943/https://www.euro.who.int/__data/assets/pdf_file/0019/123058/AQG2ndEd_5_4carbodisulfide.PDF |url-status=dead }}</ref><ref>{{Cite report |url=https://www.cdc.gov/niosh/docs/2018-124/ |title=Preventing hearing loss caused by chemical (ototoxicity) and noise exposure. |date=2018-03-01 |publisher=U.S. Department of Health and Human Services, Public Health Service, Centers for Disease Control and Prevention, National Institute for Occupational Safety and Health |doi=10.26616/nioshpub2018124 |language=en|doi-access=free }}</ref> [[Chemical hazard|Occupational exposure]] to carbon disulfide is also associated with [[cardiovascular disease]], particularly [[stroke]].<ref name="SBU2017">{{cite web |url=http://www.sbu.se/en/publications/sbu-assesses/occupational-health-and-safety--chemical-exposure/ |title=Occupational health and safety – chemical exposure |publisher=[[Swedish Agency for Health Technology Assessment and Assessment of Social Services]] (SBU) |website=www.sbu.se |language=en |access-date=2017-06-07 |archive-url=https://web.archive.org/web/20170606093333/http://www.sbu.se/en/publications/sbu-assesses/occupational-health-and-safety--chemical-exposure/ |archive-date=2017-06-06 |url-status=dead }}</ref> In 2000, the WHO believed that health harms were unlikely at levels below 100 μg/m<sup>3</sup>, and set this as a guideline level.{{needs update|date=November 2023}} Carbon disulfide can be smelled at levels above 200 μg/m<sup>3</sup>, and the WHO recommended a sensory guideline of below 20 μg/m<sup>3</sup>. Exposure to carbon disulfide is well-established to be harmful to health in concentrations at or above 30&nbsp;mg/m<sup>3</sup>. Changes in the function of the central nervous system have been observed at concentrations of 20–25&nbsp;mg/m<sup>3</sup>. There are also reports of harms to health at 10&nbsp;mg/m<sup>3</sup>, for exposures of 10–15 years, but the lack of good data on past exposure levels make the association of these harms with concentrations of 10&nbsp;mg/m<sup>3</sup> findings uncertain. The measured concentration of 10&nbsp;mg/m<sup>3</sup> may be equivalent to a concentration in the general environment of 1&nbsp;mg/m<sup>3</sup>.<ref name="WHO"/> ===Environmental sources=== The primary source of carbon disulfide in the environment is [[rayon]] factories.<ref name="WHO"/> Most global carbon disulfide emissions come from rayon production, as of 2008.<ref name=dir/> Other sources include the production of [[cellophane]], [[carbon tetrachloride]],<ref name=dir>{{cite web |url=https://www.dir.ca.gov/dosh/DoshReg/CarbonDisulfide5155-4-08.doc|type=DOC|title=Carbon Disulfide Health Effects Assessment for HEAC Discussion April 2008|date=April 2008|website=Division of Occupational Safety and Health|publisher=State of California Department of Industrial Relations|access-date=24 March 2023}}</ref> [[carbon black]], and sulfur recovery. Carbon disulfide production also emits hydrogen sulfide.<ref name=large-scale/> {{as of|2004}}, about 250 g of carbon disulfide is emitted per kilogram of rayon produced. About 30 g of carbon disulfide is emitted per kilogram of carbon black produced. About 0.341 g of carbon disulfide is emitted per kilogram of sulfur recovered.<ref name=large-scale/> Japan has reduced carbon disulfide emissions per kilogram of rayon produced, but in other rayon-producing countries, including China, emissions are assumed to be uncontrolled (based on global modelling and large-scale free-air concentration measurements). Rayon production is steady or decreasing except in China, where it is increasing, {{as of|lc=yes|2004}}.<ref name=large-scale>{{cite journal |last1=Blake |first1=Nicola J. |title=Carbonyl sulfide and carbon disulfide: Large-scale distributions over the western Pacific and emissions from Asia during TRACE-P |journal=Journal of Geophysical Research |date=2004 |volume=109 |issue=D15 |pages=D15S05 |doi=10.1029/2003JD004259|bibcode=2004JGRD..10915S05B |s2cid=43793469 |url=https://scholars.unh.edu/cgi/viewcontent.cgi?article=1072&context=earthsci_facpub |doi-access=free }}</ref> Carbon black production in Japan and Korea uses incinerators to destroy about 99% of the carbon disulfide that would otherwise be emitted.<ref name=large-scale/> When used as a [[solvent]], Japanese emissions are about 40% of the carbon disulfide used; elsewhere, the average is about 80%.<ref name=large-scale/> Most rayon production uses carbon sulfide.<ref name=SwanBlanc>{{cite news |last1=Swan |first1=Norman |last2=Blanc |first2=Paul |title=The health burden of viscose rayon |url=http://www.abc.net.au/radionational/programs/healthreport/the-health-burden-of-viscose-rayon/8286870 |work=ABC Radio National |date=20 February 2017 |language=en|access-date=24 March 2023}}</ref><ref name="scientificamerican.com">{{cite magazine|title=Bamboo Boom: Is This Material for You?|author=Nijhuis, Michelle |magazine=Scientific American Special Editions|volume=19|issue=2|pages=60–65|url=https://www.scientificamerican.com/article/bamboo-boom/|access-date=24 March 2023|year=2009|bibcode=2009SciAm..19f..60N}}</ref> One exception is rayon made using the [[lyocell]] process, which uses a different solvent; {{as of|lc=yes|2018}} the lyocell process is not widely used, because it is more expensive than the viscose process.<ref name=brief>{{cite journal |title=Regenerated cellulose by the Lyocell process, a brief review of the process and properties :: BioResources |journal=BioRes |url=https://bioresources.cnr.ncsu.edu/resources/regenerated-cellulose-by-the-lyocell-process-a-brief-review-of-the-process-and-properties/ |date=2018}}</ref><ref name=thesis>{{cite thesis |last1=Tierney |first1=John William |title=Kinetics of Cellulose Dissolution in N-MethylMorpholine-N-Oxide and Evaporative Processes of Similar Solutions |date=2005 |url=https://trace.tennessee.edu/cgi/viewcontent.cgi?referer=&httpsredir=1&article=3796&context=utk_gradthes}}</ref> [[Cuprammonium rayon]] also does not use carbon disulfide. ===Historic and current exposure=== Industrial workers working with carbon disulfide are at high risk. Emissions may also harm the health of people living near rayon plants.<ref name="WHO"/> Concerns about carbon disulfide exposure have a long history.<ref name="Ullmann">Lay, Manchiu D. S.; Sauerhoff, Mitchell W.; Saunders, Donald R.; "Carbon Disulfide", in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2000 {{doi| 10.1002/14356007.a05_185}}</ref><ref>{{Cite book|title=The Golden Thread: How Fabric Changed History|last=St. Clair|first=Kassia|publisher=John Murray|year=2018|isbn=978-1-4736-5903-2|location=London|pages=213–215|oclc=1057250632}}</ref><ref name="Blanc 2016">{{cite book |last1=Blanc, M.D. |first1=Paul David |title=Fake Silk / The Lethal History of Viscose Rayon |date=15 November 2016 |publisher=Yale University Press |isbn=9780300204667 |url=https://yalebooks.yale.edu/book/9780300204667/fake-silk |access-date=17 December 2020 |quote=in 1915,...[of 16] carbon disulfide poisoning cases....one worker had been briefly committed to an asylum and several others had experienced nervous system complaints...}}</ref>{{rp|79}} Around 1900, carbon disulfide came to be widely used in the production of [[vulcanized rubber]]. The [[psychosis]] produced by high exposures was immediately apparent (it has been reported with 6 months of exposure<ref name="WHO"/>). [[Sir Thomas Oliver]] told a story about a [[Rubber_technology|rubber factory]] that put bars on its windows so that the workers would not [[Suicide|jump out to their deaths]].<ref name="Blanc 2016"/>{{rp|17|\}} Carbon disulfide's use in the US as a heavier-than-air burrow poison for [[Richardson's ground squirrel]] also led to reports of psychosis. No systematic medical study of the issue was published, and knowledge was not transferred to the rayon industry.<ref name=SwanBlanc/> The first large epidemiological study of rayon workers was done in the US in the late 1930s, and found fairly severe effects in 30% of the workers. Data on increased risks of heart attacks and strokes came out in the 1960s. [[Courtaulds]], a major [[rayon manufacturer]], worked hard to prevent publication of this data in the UK.<ref name=SwanBlanc/> Average concentrations in sampled rayon plants were reduced from about 250&nbsp;mg/m<sup>3</sup> in 1955–1965 to about 20–30&nbsp;mg/m<sup>3</sup> in the 1980s (US figures only?{{globalize inline|US|date=October 2021}}).<ref name="WHO"/> Rayon production has since largely moved to the developing world, especially China, Indonesia and India.<ref name="scientificamerican.com"/><ref name=SwanBlanc/> Rates of [[disability]] in modern factories are unknown, {{as of|lc=yes|2016}}.<ref name="scientificamerican.com"/><ref name="Monosson">{{cite journal |doi= 10.1126/science.aak9834|pmid=27884997|title=Toxic textiles|year= 2016 |last1= Monosson |first1= Emily |journal= Science|volume= 354|issue= 6315 |page=977|bibcode= 2016Sci...354..977M|s2cid=45869497}}</ref> Current manufacturers using the [[viscose]] process do not provide any information on harm to their workers.<ref name=SwanBlanc/><ref name="scientificamerican.com"/> ==See also== * [[Carbon monosulfide]] * [[Ethenedithione]] * [[Carbon subsulfide]] * [[Carbon diselenide]] * [[Carbon dioxide]] * [[1949 Holland Tunnel fire]], accident with truck carrying carbon disulfide. ==References== {{reflist}} ==External links== {{Commons category|Carbon disulfide}} {{EB1911 poster|Carbon Bisulphide}} *[http://www.npi.gov.au/substances/carbon-disulfide/index.html Australian National Pollutant Inventory: Carbon disulfide] *[https://www.cdc.gov/niosh/npg/npgd0104.html CDC - NIOSH Pocket Guide to Chemical Hazards - Carbon Disulfide] * [https://web.archive.org/web/20120305094145/http://www.innomotionengg.com/ Inno Motion Engineering] * Agency for Toxic Substances & Disease Registry [https://www.atsdr.cdc.gov/phs/phs.asp?id=472&tid=84#bookmark05 Public Health Statement for Carbon Disulfide], 1996. * [https://www.cdc.gov/niosh/topics/carbon-disulfide/default.html Resources on Carbon Disulfide] by the [[National Institute for Occupational Safety and Health]] * {{cite book |last1=Blanc |first1=Paul David |title=Fake silk : the lethal history of viscose rayon |date=2016 |publisher=Yale University Press |location=New Haven |isbn=9780300204667 |pages=328 |url=https://yalebooks.yale.edu/book/9780300204667/fake-silk}} {{Carbon compounds}} {{Sulfides}} {{Authority control}} {{DEFAULTSORT:Carbon Disulfide}} [[Category:Sulfides]] [[Category:Inorganic carbon compounds]] [[Category:Inorganic sulfur compounds]] [[Category:Inorganic solvents]] [[Category:Hazardous air pollutants]] [[Category:Neurotoxins]] [[Category:Dichalcogenides]] [[Category:Chemical hazards]] [[Category:Foul-smelling chemicals]] [[Category:IV-VI semiconductors]] </textarea><div class="templatesUsed"><div class="mw-templatesUsedExplanation"><p><span id="templatesused">Pages transcluded onto the current version of this page<span class="posteditwindowhelplinks"> (<a href="/wiki/Help:Transclusion" 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href="/wiki/Module:GHS_phrases" title="Module:GHS phrases">Module:GHS phrases</a> (<a href="/w/index.php?title=Module:GHS_phrases&action=edit" title="Module:GHS phrases">view source</a>) (extended confirmed protected)</li><li><a href="/wiki/Module:GHS_phrases/data" title="Module:GHS phrases/data">Module:GHS phrases/data</a> (<a href="/w/index.php?title=Module:GHS_phrases/data&action=edit" title="Module:GHS phrases/data">view source</a>) (extended confirmed protected)</li><li><a href="/wiki/Module:Gapnum" title="Module:Gapnum">Module:Gapnum</a> (<a href="/w/index.php?title=Module:Gapnum&action=edit" title="Module:Gapnum">view source</a>) (extended confirmed protected)</li><li><a href="/wiki/Module:GetParameters" title="Module:GetParameters">Module:GetParameters</a> (<a href="/w/index.php?title=Module:GetParameters&action=edit" title="Module:GetParameters">view source</a>) (template editor protected)</li><li><a href="/wiki/Module:If_empty" title="Module:If empty">Module:If empty</a> (<a 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