1,4-Dioxane Chemistry, Uses, and Occurrence - Environmental Investigation and Remediation - page 97

TABLE 2.12
USEPA 1995 Toxic Release Inventory Data for 1,4-Dioxane from EPA Sector Notebook

Average Releases per
Facility Fugitive Air Point Air Water Discharges Total Releases

3810 1763 17,246 22,841 4568

Disposal
transfers

Treatment
transfers

Energy recovery
transfers

Total
transfers

Average transfer
per facility

271 12,655 11,990 24,916 4983

Source: U.S. Environmental Protection Agency (USEPA), 1995b, Proi le of the rubber and plastics industry. Ofi ce of
Enforcement and Compliance Assurance, USEPA.
Note: Values in pounds per year for i ve plastic-resin manufacturing facilities.

wastewater treatment plants or shipped by rail for off-site treatment (North Carolina Department of
Environment and Natural Resources, 1998).
In 1992, chemical manufacturing operations produced 2.56 billion kg of terephthalic acid
(2.82 million tons). A summary of 1,4-dioxane emissions, releases, and off-site transfers for i ve
plastic-resin manufacturing facilities in 1995 is given in Table 2.12.
Many photographic i lms are produced from DMT to create a polyester i lm base. Polyester
waste material such as old x-rays and used movie i lm is commonly recycled to make DMT avail-
able for reuse. The processing of polyester waste produces 1,4-dioxane as a by-product, which
has been discharged from operations as wastewater. For example, in 1994, 140,000 pounds of
1,4-dioxane were discharged to the industrial sewer in Rochester, New York, from Kodak, the lead-
ing U.S. i lm products company. Because the industrial wastewater-treatment plant was inefi cient
for 1,4-dioxane removal, plant engineers have since devised and deployed several innovative means
to separate and collect 1,4-dioxane for on-site energy recovery so that the chemical can be used as
a fuel for plant boilers. The plant successfully eliminated the discharge of 1,4-dioxane (Eastman
Kodak Corporation, 2001).

2.4.3 1,4-D IOXANE AS A B Y -P RODUCT OF P ETROLEUM R EFINING AND
G ASOLINE A NTIKNOCK A GENT
The literature contains reference to the use and formation of 1,4-dioxane during petroleum rei ning;
however, the information that exists is insufi cient to suggest that 1,4-dioxane was present in gaso-
line at levels that can be detected or cause environmental impacts. The main impurities in rei ned
benzene are nonaromatics with nine or fewer carbon atoms, toluene, 1,4-dioxane, and aromatics
containing eight carbon atoms (Wypych, 2001). 1,4-Dioxane may also occur as an impurity of tolu-
ene. Some petroleum rei ning methods for isolating and purifying toluene have reportedly used
oxygenated reagents. Analytical methods have been specii cally developed to address the possible
residual presence of 1,4-dioxane in toluene (Cortellucci and Dietz, 1999).
Universal Oil Products Company of Chicago obtained a patent in 1938 for a petroleum rei ning
process to produce 1,4-dioxane from the ethylene by-product of petroleum rei ning and then to use
the 1,4-dioxane to serve as an antiknock agent in gasoline. Ethylene is i rst converted to ethylene
glycol by adding hydrogen peroxide; the ethylene glycol is then converted to 1,4-dioxane by using
concentrated sulfuric acid. 1,4-Dioxane acts as a polymerizing agent in the rei ning process, and
excess 1,4-dioxane remaining in the gasoline acts as an antioxidant to preserve the antiknock rating
in gasoline stored for 6 months or more (McCaffrey, 1938). 1,4-Dioxane was thus apparently con-
sidered a viable oxygenate for gasoline at levels up to 0.05 wt%, although the extent to which this
invention was put into practice has not been determined.