| 词条 | Carbon disulfide |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 476998332 | Name = Carbon disulfide | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Carbon-disulfide-2D-dimensions.png | ImageSize = 150px | ImageFile1 = Carbon-disulfide-3D-vdW.png | ImageSize1 = 150px | ImageName = Carbon disulfide | IUPACName = Methanedithione | OtherNames = Carbon bisulfide |Section1={{Chembox Identifiers | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 23012 | SMILES = C(=S)=S | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6108 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = S54S8B99E8 | InChI = 1/CS2/c2-1-3 | InChIKey = QGJOPFRUJISHPQ-UHFFFAOYAS | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/CS2/c2-1-3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QGJOPFRUJISHPQ-UHFFFAOYSA-N | CASNo = 75-15-0 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 6348 | EINECS = 200-843-6 | RTECS = FF6650000 | UNNumber = 1131 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C19033 |Section2={{Chembox Properties | C=1 | S=2 | Appearance = Colorless liquid Impure: light-yellow | Odor = Chloroform (pure) Foul (commercial) | Density = 1.539 g/cm3 (−186°C) 1.2927 g/cm3 (0 °C) 1.266 g/cm3 (25 °C)[1] | MeltingPtC = −111.61 | MeltingPt_notes = | BoilingPtC = 46.24 | Solubility = 2.58 g/L (0 °C) 2.39 g/L (10 °C) 2.17 g/L (20 °C)[1] 0.14 g/L (50 °C)[1] | RefractIndex = 1.627[4] | Viscosity = 0.436 cP (0 °C) 0.363 cP (20 °C) | SolubleOther = Soluble in alcohol, ether, benzene, oil, CHCl3, CCl4 | Solubility1 = 4.66 g/100 g[1] | Solvent1 = formic acid | Solubility2 = 45 g/100 g (20.3 °C)[1] | Solvent2 = dimethyl sulfoxide | VaporPressure = 48.1 kPa (25 °C) 82.4 kPa (40 °C)[2] | MagSus = −42.2·10−6 cm3/mol }} |Section3={{Chembox Structure | MolShape = Linear | Dipole = 0 D (20 °C)[1] }} |Section5={{Chembox Thermochemistry | DeltaHf = 88.7 kJ/mol[3] | DeltaGf = 64.4 kJ/mol[3] | Entropy = 151 J/(mol·K)[3] | HeatCapacity = 75.73 J/(mol·K)[3] | DeltaHc = 1687.2 kJ/mol[2] |Section7={{Chembox Hazards | ExternalSDS = | GHSPictograms = {{GHS02}}{{GHS06}}{{GHS08}}[4] | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|315|319|361|372}}[4] | PPhrases = {{P-phrases|210|281|305+351+338|314}}[4] ICSC 0022 | NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 0 | FlashPtC = −43 | FlashPt_ref = [3] | AutoignitionPtC = 102 | AutoignitionPt_ref = [3] | ExploLimits = 1.3–50%[19] | LD50 = 3188 mg/kg (rat, oral) | EyeHazard = Irritant | SkinHazard = Irritant | InhalationHazard = Irritant; toxic | PEL = TWA 20 ppm C 30 ppm 100 ppm (30-minute maximum peak)[5] | REL = TWA 1 ppm (3 mg/m3) ST 10 ppm (30 mg/m3) [skin][5] | IDLH = 500 ppm[5] | LC50 = >1670 ppm (rat, 1 h) 15500 ppm (rat, 1 h) 3000 ppm (rat, 4 h) 3500 ppm (rat, 4 h) 7911 ppm (rat, 2 h) 3165 ppm (mouse, 2 h)[6] | LCLo = 4000 ppm (human, 30 min)[6] |Section8={{Chembox Related | OtherCompounds = Carbon dioxide Carbonyl sulfide Carbon diselenide }}Carbon disulfide is a colorless volatile liquid with the formula CS2. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent. It has an "ether-like" odor, but commercial samples are typically contaminated with foul-smelling impurities.[7] Occurrence, manufacture, propertiesSmall amounts of carbon disulfide are released by volcanic eruptions and marshes. CS2 once was manufactured by combining carbon (or coke) and sulfur at high temperatures. C + 2S → CS2 A lower-temperature reaction, requiring only 600 °C, utilizes natural gas as the carbon source in the presence of silica gel or alumina catalysts:[7] 2 CH4 + S8 → 2 CS2 + 4 H2S 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.[8] United States production in 2007 was 56,000 tonnes.[9] SolventCarbon disulfide is a solvent for phosphorus, sulfur, selenium, bromine, iodine, fats, resins, rubber, and asphalt.[10] It has been used in the purification of single-walled carbon nanotubes.[11] ReactionsCS2 is highly flammable: CS2 + 3 O2 → CO2 + 2 SO2 It is isoelectronic with carbon dioxide but it is more reactive toward nucleophiles and more easily reduced. These differences in reactivity can be attributed to the weaker π donor-ability of the sulfido centers, which renders the carbon more electrophilic. Amines afford dithiocarbamates: 2 R2NH + CS2 → [R2NH2+][R2NCS2−] Xanthates form similarly from alkoxides: RONa + CS2 → [Na+][ROCS2−] This reaction is the basis of the manufacture of regenerated cellulose, the main ingredient of viscose, rayon and cellophane. Both xanthates and the related thioxanthates (derived from treatment of CS2 with sodium thiolates) are used as flotation agents in mineral processing. Sodium sulfide affords trithiocarbonate: Na2S + CS2 → [Na+]2[CS32−] Carbon disulfide does not hydrolyze readily, although the process is catalyzed by an enzyme carbon disulfide hydrolase. Reduction of carbon disulfide with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium trithiocarbonate:[12] 4 Na + 4 CS2 → Na2C3S5 + Na2CS3 ChlorinationChlorination of CS2 is the principal route to carbon tetrachloride:[7]CS2 + 3 Cl2 → CCl4 + S2Cl2 This conversion proceeds via the intermediacy of thiophosgene, CSCl2. Coordination chemistryCS2 is a ligand for many metal complexes, forming pi complexes. One example is CpCo(η2-CS2)(PMe3).[13] PolymerizationCS2 polymerizes upon photolysis or under high pressure to give an insoluble material called "Bridgman's black", named after the discoverer of the polymer, Percy Williams Bridgman. Trithiocarbonate (-S-C(S)-S-) linkages comprise, in part, the backbone of the polymer, which is a semiconductor.[14] UsesThe principal industrial uses of carbon disulfide, consuming 75% of the annual production, are the manufacture of viscose rayon and cellophane film.[35] It is also a valued intermediate in chemical synthesis of carbon tetrachloride. It is widely used in the synthesis of organosulfur compounds such as metam sodium, xanthates, dithiocarbamates, which are used in extractive metallurgy and rubber chemistry. Niche usesIt can be used in fumigation of airtight storage warehouses, airtight flat storages, bins, grain elevators, railroad box cars, shipholds, barges and cereal mills.[15] 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.[16] Health effectsCarbon disulfide is highly toxic. It has been linked to both acute and chronic forms of poisoning.[https://www.atsdr.cdc.gov/phs/phs.asp?id=472&tid=84#bookmark05] To identify the effects of carbon disulfide, it is necessary to confirm exposure, compatible signs and symptoms, and exclude other health conditions, as its effects are non-specific. Typical recommended TLV is 30 mg/m3, 10 ppm. Symptoms include tingling or numbness, "cramps, muscle weakness, pain, distal sensory loss, and neurophysiological impairment".[17] Occupational exposure to carbon disulfide is associated with cardiovascular disease, in particular: stroke.[18]See also
References1. ^{{cite book |last=Seidell |first=Atherton |last2=Linke |first2=William F. |year=1952 |title=Solubilities of Inorganic and Organic Compounds |publisher=Van Nostrand }} 2. ^1 {{nist |name=Carbon disulfide |id=C75150 |accessdate=2014-05-27 |mask=FFFF |units=SI }}. 3. ^1 2 3 4 5 6 7 8 9 10 {{cite web |url=http://chemister.ru/Database/properties-en.php?dbid=1&id=1955 |website=chemister.ru |title=Properties of substance: carbon disulfide}} 4. ^1 2 3 Sigma-Aldrich Co., Carbon disulfide. Retrieved on 2014-05-27. 5. ^1 2 3 {{PGCH|0104}} 6. ^1 {{IDLH|75150|Carbon disulfide}} 7. ^1 2 {{Holleman&Wiberg}}. 8. ^{{cite web |url=http://www.ihs.com/products/chemical/planning/ceh/carbon-disulfide.aspx |title=Carbon Disulfide report from IHS Chemical |accessdate= June 15, 2013 }} 9. ^{{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 |accessdate= June 15, 2013 }} 10. ^{{cite web |url=http://www.akzonobel.com/sulfurderivatives/products/carbon_disulfide/ |title=Carbon Disulfide |publisher=Akzo Nobel }} 11. ^{{cite journal |last1=Park |first1=Tae-Jin |last2=Banerjee |first2=Sarbajit |last3=Hemraj-Benny |first3=Tirandai |last4=Wong |first4=Stanislaus S. |title=Purification strategies and purity visualization techniques for single-walled carbon nanotubes |journal=Journal of Materials Chemistry |year=2006 |volume=16 |issue=2 |pages=141–154 |doi=10.1039/b510858f }} 12. ^{{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}} 13. ^{{cite journal |last=Werner |first=Helmut |title=Novel Coordination Compounds formed from CS2 and Heteroallenes |journal=Coordination Chemistry Reviews |year=1982 |volume=43 |pages=165–185 |doi=10.1016/S0010-8545(00)82095-0 }} 14. ^{{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 }} 15. ^{{Greenwood&Earnshaw2nd|page=}} 16. ^{{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 }} 17. ^1 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}} 18. ^{{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 |dead-url=yes |df= }} External links{{Commons category|Carbon disulfide}}{{EB1911 poster|Carbon Bisulphide}}
8 : Sulfides|Inorganic carbon compounds|Inorganic sulfur compounds|Inorganic solvents|Hazardous air pollutants|Neurotoxins|Dichalcogenides|Occupational safety and health |
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