1636:(having observed an increased incidence of cancer in controlled animal studies, but not in epidemiological studies of workers using the compound), and a known irritant (with a no-observed-adverse-effects level of 400 milligrams per cubic meter) at concentrations significantly higher than those found in commercial products. Animal studies in rats suggest that the greatest health risk is associated with inhalation of vapors in the pure form. The State of New York has adopted a first-in-the-nation drinking water standard for 1,4-Dioxane and set the maximum contaminant level of 1 part per billion.
1462:
421:
282:
1701:(FDA) have conducted tests on cosmetic raw materials and finished products for the levels of 1,4-dioxane. 1,4-Dioxane was present in ethoxylated raw ingredients at levels up to 1410 ppm (~0.14%wt), and at levels up to 279 ppm (~0.03%wt) in off the shelf cosmetic products. Levels of 1,4-dioxane exceeding 85 ppm (~0.01%wt) in children's shampoos indicate that close monitoring of raw materials and finished products is warranted. While the FDA encourages manufacturers to remove 1,4-dioxane, it is not required by federal law.
759:
754:
749:
54:
990:
44:
994:
70:
1245:
993:
995:
1714:
1615:
of 5170 mg/kg in rats. It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number of deaths from cancer was not significantly different
1671:
Dioxane has affected groundwater supplies in several areas. Dioxane at the level of 1 μg/L (~1 ppb) has been detected in many locations in the US. In the U.S. state of New
Hampshire, it had been found at 67 sites in 2010, ranging in concentration from 2 ppb to over 11,000 ppb. Thirty of these sites
1689:
and ammonium laureth sulfate, less abrasive and offers enhanced foaming characteristics. 1,4-Dioxane is found in small amounts in some cosmetics, a yet unregulated substance used in cosmetics in both China and the U.S. Research has found the chemical in ethoxylated raw ingredients and in
1704:
On 9 December 2019, New York passed a bill to ban the sale of cosmetics with more than 10 ppm of 1,4-dioxane as of the end of 2022. The law will also prevent the sale of household cleaning and personal care products containing more than 2 ppm of 1,4-dioxane at the end of 2022.
1684:
process, a route to some ingredients found in cleansing and moisturizing products, dioxane can contaminate cosmetics and personal care products such as deodorants, perfumes, shampoos, toothpastes and mouthwashes. The ethoxylation process makes the cleansing agents, such as
1672:
are solid waste landfills, most of which have been closed for years. In 2019, the
Southern Environmental Law Center successfully sued Greensboro, North Carolina's Wastewater treatment after 1,4-Dioxane was found at 20 times above EPA safe levels in the Haw River.
2335:
Kasai, T.; Kano, H.; Umeda, Y.; Sasaki, T.; Ikawa, N.; Nishizawa, T.; Nagano, K.; Arito, H.; Nagashima, H.; Fukushima, S. (2009). "Two-year inhalation study of carcinogenicity and chronic toxicity of 1,4-dioxane in male rats".
767:
2387:
729:
2037:
Anteunis, M. (1962). "Studies of the
Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone".
1011:
1694:(EWG) found that 97% of hair relaxers, 57% of baby soaps and 22 percent of all products in Skin Deep, their database for cosmetic products, are contaminated with 1,4-dioxane.
1660:
Dioxane tends to concentrate in the water and has little affinity for soil. It is resistant to abiotic degradation in the environment, and was formerly thought to also resist
1384:
In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons.
1433:
containers. Normally aluminium is protected by a passivating oxide layer, but when these layers are disturbed, the metallic aluminium reacts with trichloroethane to give
2284:
Kasai, T; Saito, M; Senoh, H; Umeda, Y; Aiso, S; Ohbayashi, H; Nishizawa, T; Nagano, K; Fukushima, S (2008). "Thirteen-week inhalation toxicity of 1,4-dioxane in rats".
917:
1616:
from the expected number. Dioxane is classified by the
National Toxicology Program as "reasonably anticipated to be a human carcinogen". It is also classified by the
996:
2064:
Shimizu, A.; Ikeguchi, M.; Sugai, S. (1994). "Appropriateness of DSS and TSP as internal references for 1H NMR studies of molten globule proteins in aqueous media".
2391:
1004:
905:
1807:
1782:
1156:
2243:
Kano, Hirokazu; Umeda, Yumi; Saito, Misae; Senoh, Hideki; Ohbayashi, Hisao; Aiso, Shigetoshi; Yamazaki, Kazunori; Nagano, Kasuke; Fukushima, Shoji (2008).
1258:
1353:
Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of
2413:
Zenker, Matthew J.; Borden, Robert C.; Barlaz, Morton A. (September 2003). "Occurrence and
Treatment of 1,4-Dioxane in Aqueous Environments".
1895:
1629:
470:
1617:
1227:
1223:
2522:
2505:
2388:"Governor Cuomo Announces First in the Nation Drinking Water Standard for Emerging Contaminant 1,4-Dioxane | Governor Andrew M. Cuomo"
1824:
2659:
2173:
2136:
1018:
1664:. However, more recent studies since the 2000s have found that it can be biodegraded through a number of pathways, suggesting that
913:
1588:
678:
1644:
Like some other ethers, dioxane combines with atmospheric oxygen upon prolonged exposure to air to form potentially explosive
2109:
651:
849:
1481:(THF) in some processes, because of its lower toxicity and higher boiling point (101 °C, versus 66 °C for THF).
2646:
1253:
2700:
1865:
2710:
1698:
1621:
435:
2512:. U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, December 2002.
1265:
2645:
FDA/CFSAN--Cosmetics
Handbook Part 3: Cosmetic Product-Related Regulatory Requirements and Health Hazard Issues.
1921:
710:
94:
1652:
of these mixtures is dangerous. Storage over metallic sodium could limit the risk of peroxide accumulation.
1916:
Klaus
Weissermel, Hans-Jürgen Arpe (2003) "Industrial Organic Chemistry". John Wiley & Sons, page 158.
909:
835:
368:
277:
2066:
1961:
Fischer, Reinald; Görls, Helmar; Meisinger, Philippe R.; Suxdorf, Regina; Westerhausen, Matthias (2019).
1691:
399:
219:
893:
758:
1492:. At standard pressure, the mixture of water and dioxane in the ratio 17.9:82.1 by mass is a positive
1180:
1167:
845:
753:
2574:
289:
2548:
2176:. United States Department of Health and Human Services' National Toxicology Program. Archived from
43:
1354:
1041:
957:
416:
2695:
609:
2010:
Cope, Arthur C. (1935). "The
Preparation of Dialkylmagnesium Compounds from Grignard Reagents".
748:
2199:
1686:
827:
627:
2705:
1434:
1426:
1316:
861:
781:
741:
1934:
Schneider, Charles H.; Lynch, Cecil C. (1943). "The
Ternary System: Dioxane—Ethanol—Water".
945:
823:
2526:
2502:
2345:
2293:
1821:
1523:
1366:
941:
377:
239:
167:
82:
53:
929:
8:
1732:
1527:
1442:
1438:
925:
143:
133:
24:
2349:
2297:
1963:"Structure–Solubility Relationship of 1,4-Dioxane Complexes of Di(hydrocarbyl)magnesium"
921:
420:
281:
199:
2369:
2317:
2091:
1987:
1962:
1609:
1393:
869:
179:
2690:
2628:
2463:
2361:
2309:
2266:
2148:
2135:
Buffler, Patricia A.; Wood, Susan M.; Suarez, Lucina; Kilian, Duane J. (April 1978).
2083:
1992:
1917:
1861:
1531:
1461:
1446:
1401:
1370:
2607:"Occurrence of 1,4-dioxane in cosmetic raw materials and finished cosmetic products"
2373:
2321:
2095:
2618:
2453:
2422:
2353:
2301:
2256:
2113:
2075:
2046:
2019:
1982:
1974:
1943:
1853:
1737:
1319:
1283:
587:
493:
2458:
2441:
341:
2509:
2481:
2230:
1828:
1592:
1478:
1474:
1054:
885:
857:
2426:
1665:
1661:
1378:
1236:
961:
877:
598:
2357:
2305:
1778:
1138:
1111:
1078:
933:
873:
2684:
2623:
2606:
1857:
1799:
1466:
1331:
889:
576:
566:
548:
270:
897:
795:
2632:
2467:
2365:
2313:
2270:
2087:
1996:
1978:
1884:
1681:
1649:
1017:
953:
2152:
1504:
1503:. It forms adducts with a variety of Lewis acids. It is classified as a
1489:
1409:
1397:
1347:
1343:
1030:
937:
2050:
2023:
1947:
1713:
1477:, e.g. for inks, adhesives, and cellulose esters. It is substituted for
1425:
In the 1980s, most of the dioxane produced was used as a stabilizer for
1003:
901:
259:
2660:"New York restricts 1,4-dioxane in cleaning and personal care products"
2261:
2244:
2112:. National Institute for Occupational Safety and Health. Archived from
2079:
1633:
1500:
1374:
1010:
521:
290:
230:
17:
2440:
Zhang, Shu; Gedalanga, Phillip B.; Mahendra, Shaily (December 2017).
2177:
1742:
1727:
1722:
1508:
1493:
1430:
1405:
841:
388:
1235:
Except where otherwise noted, data are given for materials in their
1645:
1485:
1219:
976:
316:
250:
1776:
1392:
The dioxane molecule is centrosymmetric, meaning that it adopts a
969:
166:
2647:
Prohibited
Ingredients and other Hazardous Substances: 9. Dioxane
1526:
by linking metal centers. In this way, it is used to drive the
881:
556:
328:
787:
2442:"Advances in bioremediation of 1,4-dioxane-contaminated waters"
1450:
1339:
811:
210:
1400:. However, the molecule is conformationally flexible, and the
69:
2549:"Watchdog issues inspection results on Johnson & Johnson"
2245:"Thirteen-week oral toxicity of 1,4-dioxane in rats and mice"
1804:
Immediately Dangerous to Life or Health Concentrations (IDLH)
1484:
While diethyl ether is rather insoluble in water, dioxane is
1323:
1215:
949:
352:
190:
156:
1960:
1473:
Dioxane is used in a variety of applications as a versatile
853:
404:
1327:
1304:
1289:
1193:
803:
542:
307:
1449:. Dioxane "poisons" this catalysis reaction by forming an
1295:
865:
1850:
Dioxane in Ullmann's Encyclopedia of Industrial Chemistry
1530:, allowing the synthesis of dialkyl magnesium compounds.
815:
2137:"Mortality Follow-up of Workers Exposed to 1,4-Dioxane"
2134:
1628:
because it is a known carcinogen in other animals. The
2439:
2600:
2598:
2596:
1808:
National Institute for Occupational Safety and Health
1783:
National Institute for Occupational Safety and Health
1668:
can be used to treat 1,4-dioxane contaminated water.
1307:
1301:
1298:
819:
2334:
2283:
2063:
1286:
799:
2242:
2225:1,4-Dioxane (1,4-Diethyleneoxide). Hazard Summary.
1292:
2593:
2412:
2229:. Created in April 1992; Revised in January 2000.
2141:Journal of Occupational and Environmental Medicine
791:
2604:
2682:
2575:"The Dangers of 1,4-Dioxane and How to Avoid It"
2482:"1,4-dioxane in Greensboro | Haw River Assembly"
807:
340:
2219:
1820:Wisconsin Department of Health Services (2013)
992:
142:
1933:
1408:of metal cations. Dioxane resembles a smaller
1326:. It is a colorless liquid with a faint sweet
965:
23:"Dioxane" redirects here. For other uses, see
2525:. Healthy Child Healthy World. Archived from
2207:. International Agency for Research on Cancer
1896:United States Environmental Protection Agency
1630:United States Environmental Protection Agency
1587:Dioxane is used as an internal standard for
1420:
581:101.1 °C (214.0 °F; 374.2 K)
2639:
1885:"1, 4-Dioxane Fact Sheet: Support Document"
2605:Black, RE; Hurley, FJ; Havery, DC (2001).
1848:Surprenant, Kenneth S. (2000). "Dioxane".
1847:
1365:Dioxane is produced by the acid-catalysed
1145:1000–3000 ppm (guinea pig, 3 hr)
571:11.8 °C (53.2 °F; 284.9 K)
419:
280:
238:
2622:
2457:
2260:
1986:
1843:
1841:
1839:
1837:
1831:. Publication 00514. Accessed 2016-11-12.
376:
2036:
2012:Journal of the American Chemical Society
1936:Journal of the American Chemical Society
1777:NIOSH Pocket Guide to Chemical Hazards.
1712:
1460:
1632:classifies dioxane as a probable human
1589:nuclear magnetic resonance spectroscopy
1334:. The compound is often called simply
415:
258:
2683:
1879:
1877:
1834:
1794:
1792:
1772:
1770:
1768:
1766:
1764:
1762:
1760:
1758:
1049:180 °C (356 °F; 453 K)
271:
2249:The Journal of Toxicological Sciences
1690:off-the-shelf cosmetic products. The
1373:, which in turn is obtained from the
447:Key: RYHBNJHYFVUHQT-UHFFFAOYSA-N
444:InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
218:
198:
2523:"Chemical Encyclopedia: 1,4-dioxane"
2227:U.S. Environmental Protection Agency
2110:"International Chemical Safety Card"
2009:
1910:
1441:of the remaining trichloroethane to
1035:12 °C (54 °F; 285 K)
454:InChI=1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
2446:Journal of Environmental Management
1874:
1814:
1789:
1755:
1639:
457:Key: RYHBNJHYFVUHQT-UHFFFAOYAN
331:
315:
13:
1412:with only two ethyleneoxyl units.
1174:TWA 100 ppm (360 mg/m)
1121:10,109 ppm (mouse, 2 hr)
988:
52:
42:
14:
2722:
2415:Environmental Engineering Science
1699:U.S. Food and Drug Administration
1187:Ca C 1 ppm (3.6 mg/m)
1150:2085 ppm (mouse, 8 hr)
2039:The Journal of Organic Chemistry
1469:for the system 1,4-dioxane/water
1282:
1243:
1148:12,022 ppm (cat, 7 hr)
757:
752:
747:
505:
68:
2652:
2581:. Aspen Clean. 11 February 2020
2567:
2541:
2515:
2496:
2474:
2433:
2406:
2380:
2328:
2277:
2236:
2192:
2166:
2128:
2102:
2057:
2030:
1626:possibly carcinogenic to humans
1582:
1507:and its base parameters in the
1456:
1404:is easily adopted, e.g. in the
1239:(at 25 °C , 100 kPa).
2003:
1967:Chemistry – A European Journal
1954:
1927:
1655:
1437:, which in turn catalyses the
1097:7.6 g/kg (rabbit, dermal)
1094:3 g/kg (guinea pig, oral)
711:Occupational safety and health
511:
499:
1:
2611:Journal of AOAC International
2459:10.1016/j.jenvman.2017.05.033
1748:
1598:
1429:for storage and transport in
1161:(US health exposure limits):
47:Chemical structure of dioxane
2174:"12th Report on Carcinogens"
1717:The three isomers of dioxane
1675:
1534:is prepared in this manner:
1499:The oxygen atoms are weakly
1453:with aluminium trichloride.
1387:
1360:
7:
2503:Tenth Report on Carcinogens
2067:Journal of Biomolecular NMR
1708:
1692:Environmental Working Group
1067:or concentration (LD, LC):
724:Suspected human carcinogen
38:
10:
2727:
2427:10.1089/109287503768335913
1396:, typical of relatives of
1350:) are rarely encountered.
1338:because the other dioxane
603:29 mmHg (20 °C)
22:
15:
2701:IARC Group 2B carcinogens
2358:10.1080/08958370802629610
2306:10.1080/08958370802105397
2201:IARC Monographs Volume 71
1892:OPPT Chemical Fact Sheets
1603:
1421:Trichloroethane transport
1357:in aluminium containers.
1233:
1204:
1155:
1088:5 g/kg (mouse, oral)
1063:
728:
708:
703:
620:
486:
466:
431:
126:
105:
93:
81:
76:
67:
37:
2711:Sweet-smelling chemicals
1858:10.1002/14356007.a08_545
1355:chlorinated hydrocarbons
836:Precautionary statements
16:Not to be confused with
2555:. Xinhua. 21 March 2009
2508:1 November 2004 at the
1827:16 October 2020 at the
1515: = 1.86 and C
1496:that boils at 87.6 °C.
1415:
1091:4 g/kg (rat, oral)
610:Magnetic susceptibility
2624:10.1093/jaoac/84.3.666
1979:10.1002/chem.201903120
1822:1,4-Dioxane Fact Sheet
1718:
1687:sodium laureth sulfate
1680:As a byproduct of the
1470:
1124:12,568 ppm (rat, 2 hr)
999:
616:−52.16·10 cm/mol
58:
48:
2338:Inhalation Toxicology
2286:Inhalation Toxicology
1716:
1524:coordination polymers
1464:
1435:aluminium trichloride
1427:1,1,1-trichloroethane
998:
95:Systematic IUPAC name
56:
46:
1519: = 1.29.
1112:median concentration
981:(fire diamond)
99:1,4-Dioxacyclohexane
83:Preferred IUPAC name
2529:on 29 November 2009
2350:2009InhTx..21..889K
2298:2008InhTx..20..961K
2051:10.1021/jo01049a060
2024:10.1021/ja01314a059
1973:(55): 12830–12841.
1948:10.1021/ja01246a015
1733:Dioxane tetraketone
1622:Group 2B carcinogen
1528:Schlenk equilibrium
1443:vinylidene chloride
1439:dehydrohalogenation
1330:similar to that of
1322:, classified as an
645:196.6 J/K·mol
588:Solubility in water
529: g·mol
180:Beilstein Reference
34:
25:Dioxane (compounds)
2484:. 18 November 2020
2394:on 29 October 2020
2262:10.2131/jts.33.141
2080:10.1007/BF00398414
1719:
1471:
1394:chair conformation
1266:Infobox references
1205:Related compounds
1196:(Immediate danger)
1000:
699:−2363 kJ/mol
117:Diethylene dioxide
59:
49:
32:
2452:(Pt 2): 765–774.
1532:Dimethylmagnesium
1522:Dioxane produces
1447:hydrogen chloride
1402:boat conformation
1371:diethylene glycol
1274:Chemical compound
1272:
1271:
1211:Related compounds
782:Hazard statements
672:−354 kJ/mol
537:Colorless liquid
400:CompTox Dashboard
168:Interactive image
63:
62:
2718:
2675:
2674:
2672:
2670:
2656:
2650:
2643:
2637:
2636:
2626:
2602:
2591:
2590:
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2586:
2571:
2565:
2564:
2562:
2560:
2545:
2539:
2538:
2536:
2534:
2519:
2513:
2500:
2494:
2493:
2491:
2489:
2478:
2472:
2471:
2461:
2437:
2431:
2430:
2410:
2404:
2403:
2401:
2399:
2390:. Archived from
2384:
2378:
2377:
2332:
2326:
2325:
2281:
2275:
2274:
2264:
2240:
2234:
2223:
2217:
2216:
2214:
2212:
2206:
2196:
2190:
2189:
2187:
2185:
2170:
2164:
2163:
2161:
2159:
2132:
2126:
2125:
2123:
2121:
2116:on 29 April 2005
2106:
2100:
2099:
2061:
2055:
2054:
2034:
2028:
2027:
2007:
2001:
2000:
1990:
1958:
1952:
1951:
1942:(6): 1063–1066.
1931:
1925:
1924:, 9783527305780.
1914:
1908:
1907:
1905:
1903:
1889:
1881:
1872:
1871:
1845:
1832:
1818:
1812:
1811:
1796:
1787:
1786:
1774:
1738:Oxalic anhydride
1640:Explosion hazard
1320:organic compound
1314:
1313:
1310:
1309:
1306:
1303:
1300:
1297:
1294:
1291:
1288:
1256:
1250:
1247:
1246:
1139:lowest published
1055:Explosive limits
1020:
1013:
1006:
991:
971:
967:
963:
959:
955:
951:
947:
943:
939:
935:
931:
927:
923:
919:
915:
911:
907:
903:
899:
895:
891:
887:
883:
879:
875:
871:
867:
863:
859:
855:
851:
847:
843:
829:
825:
821:
817:
813:
809:
805:
801:
797:
793:
789:
761:
756:
751:
695:
668:
641:
621:Thermochemistry
561:1.033 g/mL
528:
513:
507:
501:
494:Chemical formula
424:
423:
408:
406:
380:
344:
333:
319:
292:
284:
273:
262:
242:
222:
202:
170:
146:
119:Diethylene ether
72:
39:
35:
31:
2726:
2725:
2721:
2720:
2719:
2717:
2716:
2715:
2681:
2680:
2679:
2678:
2668:
2666:
2658:
2657:
2653:
2649:Web.archive.org
2644:
2640:
2603:
2594:
2584:
2582:
2573:
2572:
2568:
2558:
2556:
2547:
2546:
2542:
2532:
2530:
2521:
2520:
2516:
2510:Wayback Machine
2501:
2497:
2487:
2485:
2480:
2479:
2475:
2438:
2434:
2411:
2407:
2397:
2395:
2386:
2385:
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2333:
2329:
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2278:
2241:
2237:
2224:
2220:
2210:
2208:
2204:
2198:
2197:
2193:
2183:
2181:
2180:on 14 July 2014
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2035:
2031:
2008:
2004:
1959:
1955:
1932:
1928:
1915:
1911:
1901:
1899:
1898:. February 1995
1887:
1883:
1882:
1875:
1868:
1846:
1835:
1829:Wayback Machine
1819:
1815:
1798:
1797:
1790:
1775:
1756:
1751:
1711:
1697:Since 1979 the
1678:
1658:
1642:
1613:
1608:Dioxane has an
1606:
1601:
1593:deuterium oxide
1585:
1577:
1573:
1569:
1565:
1561:
1557:
1553:
1549:
1545:
1541:
1518:
1514:
1488:and in fact is
1479:tetrahydrofuran
1475:aprotic solvent
1459:
1423:
1418:
1390:
1363:
1285:
1281:
1275:
1268:
1263:
1262:
1261: ?)
1252:
1248:
1244:
1240:
1226:
1222:
1218:
1212:
1197:
1184:
1171:
1149:
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1025:
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1023:
1022:
1015:
1008:
1001:
997:
989:
838:
784:
770:
744:
721:
696:
693:
687:
683:
680:
679:Std enthalpy of
669:
666:
660:
656:
653:
652:Std enthalpy of
642:
639:
632:
629:
613:
590:
526:
516:
510:
504:
496:
482:
479:
474:
473:
462:
459:
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347:
334:
322:
302:
265:
245:
225:
205:
182:
173:
160:
149:
136:
122:
121:Dioxane solvent
120:
118:
116:
114:
109:
101:
100:
89:
88:
28:
21:
12:
11:
5:
2724:
2714:
2713:
2708:
2703:
2698:
2696:Ether solvents
2693:
2677:
2676:
2651:
2638:
2592:
2566:
2540:
2514:
2495:
2473:
2432:
2421:(5): 423–432.
2405:
2379:
2344:(11): 889–97.
2327:
2292:(10): 961–71.
2276:
2235:
2218:
2191:
2165:
2147:(4): 255–259.
2127:
2101:
2056:
2029:
2002:
1953:
1926:
1909:
1873:
1867:978-3527306732
1866:
1833:
1813:
1788:
1753:
1752:
1750:
1747:
1746:
1745:
1740:
1735:
1730:
1725:
1710:
1707:
1677:
1674:
1666:bioremediation
1662:biodegradation
1657:
1654:
1641:
1638:
1611:
1605:
1602:
1600:
1597:
1584:
1581:
1580:
1579:
1575:
1571:
1567:
1563:
1559:
1555:
1551:
1547:
1543:
1539:
1516:
1512:
1458:
1455:
1422:
1419:
1417:
1414:
1389:
1386:
1379:ethylene oxide
1362:
1359:
1273:
1270:
1269:
1264:
1242:
1241:
1237:standard state
1234:
1231:
1230:
1213:
1210:
1207:
1206:
1202:
1201:
1198:
1192:
1189:
1188:
1185:
1179:
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1175:
1172:
1166:
1163:
1162:
1153:
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1143:
1134:
1132:
1129:
1128:
1126:
1125:
1122:
1118:
1116:
1107:
1105:
1102:
1101:
1099:
1098:
1095:
1092:
1089:
1085:
1083:
1074:
1072:
1069:
1068:
1061:
1060:
1057:
1051:
1050:
1047:
1040:
1037:
1036:
1033:
1027:
1026:
1016:
1009:
1002:
987:
986:
985:
984:
982:
973:
972:
918:P305+P351+P338
906:P303+P361+P353
839:
834:
831:
830:
785:
780:
777:
776:
771:
766:
763:
762:
745:
740:
737:
736:
726:
725:
722:
719:
716:
715:
706:
705:
701:
700:
697:
691:
685:
677:
674:
673:
670:
664:
658:
650:
647:
646:
643:
637:
626:
623:
622:
618:
617:
614:
608:
605:
604:
601:
599:Vapor pressure
595:
594:
591:
586:
583:
582:
579:
573:
572:
569:
563:
562:
559:
553:
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365:
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304:
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123:
107:
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102:
98:
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91:
90:
86:
85:
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73:
65:
64:
61:
60:
50:
9:
6:
4:
3:
2:
2723:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2688:
2686:
2665:
2661:
2655:
2648:
2642:
2634:
2630:
2625:
2620:
2617:(3): 666–70.
2616:
2612:
2608:
2601:
2599:
2597:
2580:
2576:
2570:
2554:
2550:
2544:
2528:
2524:
2518:
2511:
2507:
2504:
2499:
2483:
2477:
2469:
2465:
2460:
2455:
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2447:
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2428:
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2307:
2303:
2299:
2295:
2291:
2287:
2280:
2272:
2268:
2263:
2258:
2255:(2): 141–53.
2254:
2250:
2246:
2239:
2232:
2228:
2222:
2203:
2202:
2195:
2179:
2175:
2169:
2154:
2150:
2146:
2142:
2138:
2131:
2115:
2111:
2105:
2097:
2093:
2089:
2085:
2081:
2077:
2074:(6): 859–62.
2073:
2069:
2068:
2060:
2052:
2048:
2044:
2040:
2033:
2025:
2021:
2017:
2013:
2006:
1998:
1994:
1989:
1984:
1980:
1976:
1972:
1968:
1964:
1957:
1949:
1945:
1941:
1937:
1930:
1923:
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1913:
1897:
1893:
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1878:
1869:
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1859:
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1809:
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1801:
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1771:
1769:
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1744:
1741:
1739:
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1734:
1731:
1729:
1726:
1724:
1721:
1720:
1715:
1706:
1702:
1700:
1695:
1693:
1688:
1683:
1673:
1669:
1667:
1663:
1653:
1651:
1647:
1637:
1635:
1631:
1627:
1623:
1619:
1614:
1596:
1594:
1590:
1537:
1536:
1535:
1533:
1529:
1525:
1520:
1510:
1506:
1502:
1497:
1495:
1491:
1487:
1482:
1480:
1476:
1468:
1467:phase diagram
1463:
1454:
1452:
1448:
1444:
1440:
1436:
1432:
1428:
1413:
1411:
1407:
1403:
1399:
1395:
1385:
1382:
1380:
1376:
1372:
1368:
1358:
1356:
1351:
1349:
1345:
1341:
1337:
1333:
1332:diethyl ether
1329:
1325:
1321:
1318:
1312:
1279:
1267:
1260:
1255:
1238:
1232:
1229:
1225:
1221:
1217:
1214:
1209:
1208:
1203:
1199:
1195:
1191:
1190:
1186:
1183:(Recommended)
1182:
1178:
1177:
1173:
1170:(Permissible)
1169:
1165:
1164:
1160:
1159:
1154:
1151:
1144:
1140:
1131:
1130:
1123:
1120:
1119:
1117:
1113:
1104:
1103:
1096:
1093:
1090:
1087:
1086:
1084:
1080:
1071:
1070:
1066:
1062:
1058:
1056:
1053:
1052:
1048:
1045:
1039:
1038:
1034:
1032:
1029:
1028:
1021:
1014:
1007:
983:
980:
979:
975:
974:
840:
837:
833:
832:
786:
783:
779:
778:
775:
772:
769:
765:
764:
760:
755:
750:
746:
743:
739:
738:
734:
732:
727:
723:
718:
717:
713:
712:
707:
702:
698:
690:
682:
676:
675:
671:
663:
655:
649:
648:
644:
636:
631:
625:
624:
619:
615:
611:
607:
606:
602:
600:
597:
596:
592:
589:
585:
584:
580:
578:
577:Boiling point
575:
574:
570:
568:
567:Melting point
565:
564:
560:
558:
555:
554:
550:
549:diethyl ether
546:
544:
541:
540:
536:
533:
532:
525:
523:
520:
519:
498:
495:
491:
490:
485:
476:
475:
472:
465:
451:
441:
440:
437:
430:
422:
418:
417:DTXSID4020533
414:
413:
411:
401:
397:
396:
392:
390:
387:
386:
379:
375:
374:
372:
370:
367:
366:
359:
358:
356:
354:
351:
350:
343:
339:
338:
336:
330:
326:
325:
318:
314:
313:
311:
309:
306:
305:
298:
297:
295:
293:
288:
287:
283:
279:
276:
274:
272:ECHA InfoCard
269:
268:
261:
257:
256:
254:
252:
249:
248:
241:
237:
236:
234:
232:
229:
228:
221:
217:
216:
214:
212:
209:
208:
201:
197:
196:
194:
192:
189:
188:
184:
181:
177:
176:
169:
165:
164:
162:
158:
153:
152:
145:
141:
140:
138:
135:
131:
130:
125:
112:
104:
96:
92:
84:
80:
75:
71:
66:
55:
51:
45:
41:
40:
36:
30:
26:
19:
2706:Crown ethers
2667:. Retrieved
2663:
2654:
2641:
2614:
2610:
2583:. Retrieved
2578:
2569:
2557:. Retrieved
2552:
2543:
2531:. Retrieved
2527:the original
2517:
2498:
2486:. Retrieved
2476:
2449:
2445:
2435:
2418:
2414:
2408:
2396:. Retrieved
2392:the original
2382:
2341:
2337:
2330:
2289:
2285:
2279:
2252:
2248:
2238:
2226:
2221:
2209:. Retrieved
2200:
2194:
2182:. Retrieved
2178:the original
2168:
2156:. Retrieved
2144:
2140:
2130:
2118:. Retrieved
2114:the original
2104:
2071:
2065:
2059:
2042:
2038:
2032:
2018:(11): 2238.
2015:
2011:
2005:
1970:
1966:
1956:
1939:
1935:
1929:
1912:
1900:. Retrieved
1891:
1849:
1816:
1803:
1703:
1696:
1682:ethoxylation
1679:
1670:
1659:
1650:Distillation
1643:
1625:
1607:
1586:
1583:Spectroscopy
1521:
1498:
1483:
1472:
1457:As a solvent
1424:
1391:
1383:
1364:
1352:
1335:
1317:heterocyclic
1277:
1276:
1157:
1147:
1064:
1042:Autoignition
977:
773:
730:
720:Main hazards
709:
688:
661:
634:
353:RTECS number
220:ChEMBL453716
127:Identifiers
110:
106:Other names
33:1,4-Dioxane
29:
2669:13 November
2664:Cen.acs.org
2585:17 December
2579:Aspen Clean
2553:China Daily
2533:14 December
1656:Environment
1501:Lewis-basic
1490:hygroscopic
1410:crown ether
1398:cyclohexane
1367:dehydration
1278:1,4-Dioxane
1079:median dose
1065:Lethal dose
1044:temperature
1031:Flash point
768:Signal word
714:(OHS/OSH):
534:Appearance
487:Properties
278:100.004.239
200:CHEBI:47032
87:1,4-Dioxane
57:1,4-dioxane
2685:Categories
2398:30 October
2231:Fact Sheet
2120:6 February
2045:(2): 596.
1922:3527305785
1749:References
1634:carcinogen
1599:Toxicology
1375:hydrolysis
742:Pictograms
681:combustion
522:Molar mass
378:J8A3S10O7S
231:ChemSpider
155:3D model (
134:CAS Number
18:1,4-Dioxin
1800:"Dioxane"
1743:Dioxanone
1728:9-crown-3
1723:Dioxolane
1676:Cosmetics
1646:peroxides
1542:MgBr + (C
1509:ECW model
1505:hard base
1494:azeotrope
1431:aluminium
1406:chelation
1388:Structure
1361:Synthesis
1228:Pentoxane
1224:Tetroxane
962:P403+P235
958:P403+P233
954:P370+P378
946:P337+P313
942:P332+P313
926:P308+P313
922:P307+P311
914:P304+P340
910:P304+P312
902:P302+P352
733:labelling
654:formation
628:Std molar
593:Miscible
389:UN number
360:JG8225000
299:204-661-8
291:EC Number
2691:Dioxanes
2633:11417628
2506:Archived
2468:28625566
2374:45963495
2366:19681729
2322:86811931
2314:18668411
2271:18544906
2158:26 March
2096:34800494
2088:22911388
1997:31328293
1825:Archived
1810:(NIOSH).
1785:(NIOSH).
1709:See also
1486:miscible
1220:Trioxane
1059:2.0–22%
978:NFPA 704
704:Hazards
612:(χ)
478:O1CCOCC1
251:DrugBank
144:123-91-1
115:-crown-2
113:-Dioxane
2346:Bibcode
2294:Bibcode
2211:11 July
2184:11 July
1988:7027550
1779:"#0237"
1465:Binary
1340:isomers
1336:dioxane
1315:) is a
1259:what is
1257: (
630:entropy
557:Density
329:PubChem
260:DB03316
185:102551
108:Dioxane
2631:
2559:14 May
2488:13 May
2466:
2372:
2364:
2320:
2312:
2269:
2153:641607
2151:
2094:
2086:
1995:
1985:
1920:
1902:14 May
1864:
1604:Safety
1554:→ MgBr
1451:adduct
1254:verify
1251:
774:Danger
551:-like
547:Mild,
527:88.106
471:SMILES
317:C14440
211:ChEMBL
77:Names
2370:S2CID
2318:S2CID
2205:(PDF)
2092:S2CID
1888:(PDF)
1620:as a
1570:+ (CH
1511:are E
1324:ether
1216:Oxane
1158:NIOSH
436:InChI
393:1165
342:31275
240:29015
191:ChEBI
157:JSmol
2671:2021
2629:PMID
2587:2020
2561:2010
2535:2009
2490:2022
2464:PMID
2400:2020
2362:PMID
2310:PMID
2267:PMID
2213:2014
2186:2014
2160:2016
2149:PMID
2122:2006
2084:PMID
1993:PMID
1918:ISBN
1904:2010
1862:ISBN
1618:IARC
1538:2 CH
1445:and
1416:Uses
1348:1,3-
1346:and
1344:1,2-
1328:odor
1200:Ca
1194:IDLH
970:P501
966:P405
950:P362
938:P321
934:P314
930:P312
898:P281
894:P280
890:P271
886:P270
882:P264
878:P261
874:P260
870:P243
866:P242
862:P241
858:P240
854:P233
850:P210
846:P202
842:P201
828:H373
824:H372
820:H370
816:H351
812:H336
808:H332
804:H319
800:H315
796:H305
792:H302
788:H225
543:Odor
369:UNII
308:KEGG
2619:doi
2454:doi
2450:204
2423:doi
2354:doi
2302:doi
2257:doi
2076:doi
2047:doi
2020:doi
1983:PMC
1975:doi
1944:doi
1854:doi
1591:in
1377:of
1369:of
1181:REL
1168:PEL
731:GHS
692:298
665:298
638:298
405:EPA
332:CID
2687::
2662:.
2627:.
2615:84
2613:.
2609:.
2595:^
2577:.
2551:.
2462:.
2448:.
2444:.
2419:20
2417:.
2368:.
2360:.
2352:.
2342:21
2340:.
2316:.
2308:.
2300:.
2290:20
2288:.
2265:.
2253:33
2251:.
2247:.
2145:20
2143:.
2139:.
2090:.
2082:.
2070:.
2043:27
2041:.
2016:57
2014:.
1991:.
1981:.
1971:25
1969:.
1965:.
1940:65
1938:.
1894:.
1890:.
1876:^
1860:.
1852:.
1836:^
1806:.
1802:.
1791:^
1781:.
1757:^
1648:.
1624::
1612:50
1610:LD
1595:.
1578:Mg
1566:O)
1558:(C
1550:O)
1381:.
1305:eɪ
1290:aɪ
1135:Lo
1133:LC
1108:50
1106:LC
1075:50
1073:LD
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