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Cas Database

123-91-1

123-91-1

Identification

  • Product Name:1,4-Dioxane

  • CAS Number: 123-91-1

  • EINECS:204-661-8

  • Molecular Weight:88.1063

  • Molecular Formula: C4H8O2

  • HS Code:29329990

  • Mol File:123-91-1.mol

Synonyms:Diethylene dioxide;p-Dioxan;NCI-C03689;1, 4-Diethylene dioxide;Silane,[1,3-dioxan-5-ylidenebis(methyleneoxy)]- bis-;Diossano-1,4;Dioxane;Dioxan-1, 4;Diethylene ether;1,4-Dioxan;Di (ethylene oxide);Tetrahydro-p-dioxin;Dioxaan-1,4;Tetrahydro-1,4-dioxin;Glycol ethylene ether;Dioxanne;Dioksan;Dioxane-1,4;Diokan;Dioxan;p-dioxane;Dioxyethylene ether;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,HarmfulXn

  • Hazard Codes:Xn,F,T

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH319 Causes serious eye irritation H335 May cause respiratory irritation H351 Suspected of causing cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer immediately for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. In case of eye contact Rinse with plenty of water for several minutes (remove contact lenses if easily possible). If swallowed Rinse mouth. Do NOT induce vomiting. Seek medical attention if you feel unwell. No significant irritation from brief exposure of skin; prolonged or repeated exposure may cause a rash or burn and absorption of toxic amounts leading to serious injury of liver and kidney. Chemical has poor warning properties; illness may be delayed. Moderately irritating to eyes; overexposure may cause corneal injury. (USCG, 1999) Exposures of the eye... must be flushed immediately with water. Likewise, any clothing that becomes contaminated with dioxane should be removed and contaminated skin irrigated with soap and water.

  • Fire-fighting measures: Suitable extinguishing media Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray, dry chemical. "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Special Hazards of Combustion Products: Toxic vapors are generated when heated. Behavior in Fire: Vapor is heavier than air and may travel to a source of ignition and flash back. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable air tight containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. 1) Remove all ignition sources. 2) ventilate area of spill or leak. 3) for small quantities, absorb on paper towels. Evaporate in safe place (such as flame hood). Allow ... to completely clear hood ductwork. Burn in suitable location away from combustible materials. Large quantities can be collected and atomized in suitable combustion chamber equipped with appropriate effluent gas cleaning device. Dioxane should not be allowed to enter confined space, such as sewer. ...

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants, strong acids and incompatible materials. Cool. Dry. Well closed. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, and sunlight. Outside or detached storage is preferred. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet.

  • Exposure controls/personal protection:Occupational Exposure limit valuesNIOSH considers dioxane to be a potential occupational carcinogen.NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration.Recommended Exposure Limit: 30 Minute Ceiling value: 1 ppm (3.6 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:1,4-Dioxane
  • Packaging:25g
  • Price:$ 140
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,4-Dioxane (stabilized with BHT) >99.0%(GC)
  • Packaging:500g
  • Price:$ 23
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,4-Dioxane (stabilized with BHT) >99.0%(GC)
  • Packaging:25g
  • Price:$ 16
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1,4-Dioxane 99%
  • Packaging:1 L
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1,4-Dioxane 99%
  • Packaging:2.5 L
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dioxane solution NMR reference standard, 40% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 6.5 mm × 8 in.
  • Packaging:10x8in
  • Price:$ 3510
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dioxane solution NMR reference standard, 10% in benzene-d6 (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 5 mm × 8 in.
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dioxane for analysis EMSURE? ACS,ISO
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dioxane solution NMR reference standard, 5 mM in chloroform-d (99.8 atom % D), NMR tube size 3 mm × 8 in.
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dioxane solution NMR reference standard, 5 mM in benzene-d6 (99.6 atom % D), NMR tube size 3 mm × 8 in.
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Relevant articles and documentsAll total 90 Articles be found

Synthesis of cyclic ethers from diols in the presence of copper catalysts

Bayguzina,Gimaletdinova,Khusnutdinov

, p. 1840 - 1843 (2017)

A number of cyclic ethers, namely tetrahydrofuran, 2,5-dimethyltetrahydrofuran, tetrahydropyran, 1,4-dioxane, oxepane, oxocane, and 1,4-oxathiane, have been synthesized in high yields by intramolecular dehydration of diols in the presence of copper-based catalysts.

Reaction of butyltin hydroxide oxide with p-toluenesulfonic acid: Synthesis, X-ray crystal analysis, and multinuclear NMR characterization of {(BuSn)12O14(OH)6}(4-CH3C 6H4SO3)2

Eychenne-Baron, Christophe,Ribot, Fran?ois,Steunou, Nathalie,Sanchez, Clément,Fayon, Franck,Biesemans, Monique,Martins, José C.,Willem, Rudolph

, p. 1940 - 1949 (2000)

The reaction of butyltin hydroxide oxide, BuSnO(OH), with p-toluenesulfonic acid, 4-CH3C6H4SO3H, yields the butyltin oxo cluster {(BuSn)12(μ3-O)14(μ2-OH) 6}2+ mixed with a soluble ill-defined butyltin oxo polymer, the presence of which was established by solid-state and quantitative solution 119Sn NMR. The reaction conditions were varied in order to optimize the yield of oxo cluster, which can be quantitatively isolated by crystallization as {(BuSn)12O14(OH)6}(4-CH3C 6H4SO3)2·C4H 8O2 (1·diox). The structure of the latter compound was determined by X-ray diffraction. 1·diox and {(BuSn)12O14(OH)6}-(4-CH3C 6H4SO3)2 (1) were also characterized by solid-state 119Sn MAS NMR and solution 119Sn, 1H, and 13C NMR. In 1·diox, the existence of weak Lewis interactions, taking place in the crystal between five-coordinate tin atoms and dioxane molecules, was evidenced by solid-state 119Sn NMR. 2D 1H-1H NOESY and ROESY experiments, along with ionic conductivity measurements, have proved that the ionic dissociation between {(BuSn)12O14(OH)6}2+ and 4-CH3C6H4SO3- (PTS-) does not take place in dichloromethane, while it does in the more polar and dissociating dimethyl sulfoxide. Using the 1H-119Sn J-HMQC NMR technique, the weak 2J(1H-O-119Sn) coupling constant between the μ2-OH and the six-coordinate tin nuclei was determined and shown to depend on the solvent.

Comyns,Lucas

, p. 1019 (1954)

Skarulis,Ricci

, p. 3429 (1941)

Barnes, J. C.,Duncan, C. S.

, (1972)

-

Gordon et al.

, p. 583,587 (1955)

-

Grunwald et al.

, p. 5801,5802, 5803 (1960)

Gruhn,Gorman

, p. 482 (1965)

Synthesis of 1,4-dioxene from diethylene glycol in the presence of bifunctional copper-containing catalysts. Effect of support on the selectivity of dioxene formation

Gitis,Neumoeva,Isagulyants

, p. 23 - 29 (1996)

In the synthesis of 1,4-dioxene from diethylene glycol in the presence of a bifunctional copper-containing catalyst, the composition of the by-products has been studied and the effect of the support on the overall direction of the reactions has been investigated. It has been established that on Cu/SiO2, 1,4-dioxanone is formed together with dioxene, the yield of the former increasing with an increase in the content of copper in the catalyst. This is due to an increase in the dehydrogenating function of the latter. On the more acidic Cu/Al2O3, 1,4-dioxane is mainly obtained together with, to a lesser degree, methyl-1,3-dioxolane. This is due to the predominance of dehydration reactions followed by isomerization. Dioxene, dioxane, and methyldioxolane are formed on Cu/HNaY, and the yield of the latter increases with an increase in the degree of acidity (degree of decationization) of the zeolite. It is possible to increase the selectivity of dioxene formation substantially with the use of a catalyst with a moderately acidic zeolite, by varying its copper content and by dilution with water vapor. 1996 Plenum Publishing Corporation.

Weicksel, J. A.,Lynch, C. C.

, p. 2632 - 2636 (1950)

Rheinboldt, H.

, p. 2535 - 2535 (1941)

-

Stone,Emeleus

, p. 2755,2757 (1950)

-

-

Tratremouille et al.

, p. 120,124 (1960)

-

Catalysis, kinetic and mechanistical studies for the transformation of ethylene glycol by alumina and silica gel under autogenous pressure and solvent-free conditions

Rohand, Taoufik,Tanemura, Kiyoshi

, p. 387 - 394 (2021/06/25)

A kinetic and mechanistical studies of the new pathway for competitive transformation of ethylene glycol by alumina and silica gel have been described. Commercial alumina (Al com), synthetic alumina (Al syn), commercial silica gel (Si com) and synthetic silica gel (Si syn) were used for the transformation of ethylene glycol to a mixture of diethylene glycol, 1,4-dioxane and 2-methyl-1,3-dioxolane via acetaldehyde by heating at 150 °C under autogenous pressure without solvent. The results show that the yield of these three products strongly depends on the nature of the used catalyst and the reaction time.

Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers

Biberger, Tobias,Makai, Szabolcs,Lian, Zhong,Morandi, Bill

supporting information, p. 6940 - 6944 (2018/05/14)

Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.

Synthesis of dioxolanes and oxazolidines by silica gel catalysis

Rohand, Taoufik,Savary, Jér?me,Markó, István E.

, p. 1429 - 1436 (2018/06/25)

Abstract: Ethylene glycol condensed with carbonyl compounds in the presence of silica gel or alumina, without solvent and under pressure, affords 1,3-dioxolanes. 2-Amino-2-methylpropanol also condensed with carbonyl compounds in the presence of silica gel or an acid-activated clay, without solvent and under pressure, produces oxazolidines. To explain these results, we propose that the glycol and the aminopropanol react with Br?nsted (H+) and Lewis acid sites (Si and Al) located on the surface of the catalysts, leading to the products via various ionic intermediates.

Transition metal triflate catalyzed conversion of alcohols, ethers and esters to olefins

Keskiv?li,Parviainen,Lagerblom,Repo

, p. 15111 - 15118 (2018/05/04)

Herein, we report an efficient transition metal triflate catalyzed approach to convert biomass-based compounds, such as monoterpene alcohols, sugar alcohols, octyl acetate and tea tree oil, to their corresponding olefins in high yields. The reaction proceeds through C-O bond cleavage under solvent-free conditions, where the catalytic activity is determined by the oxophilicity and the Lewis acidity of the metal catalyst. In addition, we demonstrate how the oxygen containing functionality affects the formation of the olefins. Furthermore, the robustness of the used metal triflate catalysts, Fe(OTf)3 and Hf(OTf)4, is highlighted by their ability to convert an over 2400-fold excess of 2-octanol to octenes in high isolated yields.

Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol

Yu, Weiqiang,Lu, Fang,Huang, Qianqian,Lu, Rui,Chen, Shuai,Xu, Jie

supporting information, p. 3327 - 3333 (2017/07/28)

Etherification of ethylene glycol with methanol provides a sustainable route for the production of widely used dimethoxyethane; dimethoxyethane is a green solvent and reagent that is applied in batteries and used as a potential diesel fuel additive. SAPO-34 zeolite was found to be an efficient and highly selective catalyst for this etherification via a continuous flow experiment. It achieved up to 79.4% selectivity for dimethoxyethane with around 96.7% of conversion. The relationship of the catalyst's structure and the dimethoxyethane selectivity was established via control experiments. The results indicated that the pore structure of SAPO-34 effectively limited the formation of 1,4-dioxane from activated ethylene glycol, enhanced the reaction of the activated methanol with ethylene glycol in priority, and thus resulted in high selectivity for the desired products. The continuous flow technology used in the study could efficiently promote the complete etherification of EG with methanol to maintain high selectivity for dimethoxyethane.

Process route upstream and downstream products

Process route

2,2-dimethyl-3,6,9,12-tetraoxa-2-silatridecane
864079-62-9

2,2-dimethyl-3,6,9,12-tetraoxa-2-silatridecane

Dimethyl ether
115-10-6,157621-61-9

Dimethyl ether

Trimethylmethoxysilane
1825-61-2

Trimethylmethoxysilane

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

Conditions
Conditions Yield
With Cp*Si(1+)* B(C6F5)4(1-); In dichloromethane-d2; at -30 ℃; Inert atmosphere;
diethylene glycol
111-46-6

diethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

ethylene glycol
107-21-1

ethylene glycol

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

Conditions
Conditions Yield
With hydrogen; at 250 ℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;
diethylene glycol
111-46-6

diethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

Conditions
Conditions Yield
DELOXAN ASP; In carbon dioxide; at 330 ℃; under 152000 Torr;
95 % Turnov.
5 % Turnov.
ethylene glycol
107-21-1

ethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

diethylene glycol
111-46-6

diethylene glycol

Conditions
Conditions Yield
With tungsten trioxide on silica; hydrogen; In water; at 340 ℃; Temperature; Inert atmosphere;
44.9%
38.8%
28.7%
ethylene glycol
107-21-1

ethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

Conditions
Conditions Yield
With Nafion-H; at 175 ℃; for 19h; Product distribution; also in continuous flow reactor charged with Nafion-H or NaHX zeolites, at 175 deg C or 250 deg C, respectively;
71 % Chromat.
20 % Chromat.
6 % Chromat.
With sulfuric acid; In water; at 110 - 140 ℃; Product distribution;
diethylene glycol
111-46-6

diethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

1,4-dioxene
543-75-9

1,4-dioxene

Conditions
Conditions Yield
With zeolite NaY; copper; at 280 ℃; Yield given; further catalysts and conditions;
With zeolite NaY; copper; at 280 ℃; Product distribution; effect of support on selectivity of dioxene formation; further catalysts and conditions;
potassium 18-crown-6 benzene anion radical salt

potassium 18-crown-6 benzene anion radical salt

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

1,1'-oxybisethene
109-93-3,9003-19-4

1,1'-oxybisethene

cyclohexa-1,4-diene
1165952-92-0

cyclohexa-1,4-diene

cyclohexene
110-83-8

cyclohexene

Conditions
Conditions Yield
at 320 ℃; for 0.00833333h; Product distribution; Mechanism; other temperatures;
C<sub>12</sub>H<sub>24</sub>O<sub>6</sub>*C<sub>6</sub><sup>(2)</sup>H<sub>6</sub><sup>(1-)</sup>*K<sup>(1+)</sup>

C12H24O6*C6(2)H6(1-)*K(1+)

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

15-crown-5
33100-27-5

15-crown-5

1,1'-oxybisethene
109-93-3,9003-19-4

1,1'-oxybisethene

1,2,3,4,5,6-hexadeuteriocyclohexa-1,4-diene
71092-65-4

1,2,3,4,5,6-hexadeuteriocyclohexa-1,4-diene

1,2,3,4,5,6-hexadeuteriocyclohexene

1,2,3,4,5,6-hexadeuteriocyclohexene

Conditions
Conditions Yield
at 320 ℃; Product distribution; Mechanism;
ethylene glycol
107-21-1

ethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

diethylene glycol
111-46-6

diethylene glycol

Conditions
Conditions Yield
at 300 ℃; Produkt 5:Aethylen;
at 400 ℃; Produkt 5:Aethylen;
hydrogen sulfide
7783-06-4

hydrogen sulfide

ethylene glycol
107-21-1

ethylene glycol

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

1,4-Oxathiane
15980-15-1

1,4-Oxathiane

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

Conditions
Conditions Yield
at 225 ℃; Produkt 5:<1,4>Dithian;

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