1,4-Dioxane Chemistry, Uses, and Occurrence - Environmental Investigation and Remediation - page 75

TABLE 2.1
Synonyms, Translations, and Identifi cation of 1,4-Dioxane

Dioxane Glycol Ethylene Ether Diethylene Dioxide Diethylene Ether

p -Dioxane Diethylene-1,4-dioxide Dioxyethylene ether 1,4-Dioxacyclohexane

1,4-Diethylenedioxide 1,4-Dioxacyclohexane Tetrahydro-1,4-dioxane Tetrahydro- p -dioxane

Di(Ethylene oxide) Tetramethylene 1,4-oxide NE 220 Dioksan (Polish)

Diossano-1,4 (Italian) Dioxaan-1,4 (Dutch) Dioxan; dioxan-1,4 (German) 1,4-Dioksaani (Finnish)

1,4-Dioxano (Spanish) Dioxane; dioxyethylene ether;

p -dioxan (Czech)

1,4-Dioxanne; dioxane-1,4;
dioxanne (French)

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(Japanese)

1,4-Dioxan (Danish) 1,4-Dioxano (Portuguese) 1,4-Dioxan (Swedish)

1,4-διοξα ′ ν (Greek)

TABLE 2.2
Identifi cation of 1,4-Dioxane

Identifi cation Type Identifi er

Chemical Abstracts Service Registry Number (CASRN) 123-91-1

Registry of Toxic Effects of Chemical Substances (RTECS) JG8225000

United Nations Number (UN) 1165

National Institute of Occupational Safety and Health (NIOSH) JG8225000

EPA Hazardous Waste Identii cation Number U108

Department of Transportation Number 1165; Guide 127

Standard Transportation Number 49 091 55; Dioxane

European Inventory of Existing Chemical Substances (EINICS Number) 204-661-8

Beilstein Registry Number 102551

composed of two similar subunits or monomers linked together). The two remaining oxygen atoms
are available for interaction with the water molecules (Mazurkiewicz and Tomasik, 2006).
1,4-Dioxane has a slight odor similar to butanol. It is fully miscible with water and most organic
solvents, and water is fully soluble in dioxane. 1,4-Dioxane is favored as a solvent for cellulose
derivatives, polymers, chlorinated rubber, and resins, and it has many other uses, as described fur-
ther in this chapter. 1,4-Dioxane remains inert as a reagent in some chemical reactions, such as
hydrogenation and sulfonation (Stoye, 2005).
There are two other dioxane isomers, 1,2-dioxane (CASRN: 5703-46-8) and 1,3-dioxane
(CASRN: 505-22-6); in each designation, the two numbers separated by a comma indicate the oxy-
gen positions in the ring structure, as shown in Figure 2.1. 1,3-Dioxane should not be confused with
1,3-dioxolane, which has a pentagonal ring structure similar to tetrahydrofuran and is used as a
stabilizer of methyl chloroform.

O O O

H 2 C O H 2 C CH 2 H 2 C CH 2

H 2 C CH 2 H 2 C CH 2

H 2 C

O

CH 2 CH 2 O

1,2-dioxane 1,3-dioxane 1,4-dioxane

FIGURE 2.1 Structures of 1,2-dioxane, 1,3-dioxane, and 1,4-dioxane.