VAPOR-PHASE PHOTODECOMPOSITION

OF A L D E N AND DIELDRIN
DONALD G. CROSBY and KENNETHW. MOILANEN
Department o f Environmental Toxicology
University of California
Davis, California 95616

A special reactor was constructed to study the vapor-phase photodecomposition

of pesticides by ultraviolet (UV) light. The reactor was designed in such a way that
wall reactions would be minimized and could be distinguished from actual vapor-
phase transformations. The vapor-phase photodecomposition of the insecticides
aldrin and dieldrin were studied with this reactor. Irradiation of aldrin vapor with
UV light resulted in the formation of photoaldrin and dieldrin. Irradiation of either
photoaldrin or dieldrin vapor resulted in a single photoproduct, photodieldrin,
which was resistant to further photolysis. Hence, irradiation of aldrin vapor
ultimately produced photodieldrin by way of two separate pathways: a photo-
isomerization followed by photooxidation and a photooxidation followed by
photoisomerization.

Attempts to prepare environmental balance sheets for pesticides reveal that a sub-
stantial proportion of the applied amount usually cannot be accounted for (Woodwell
e t al. 1971). As an example, the low efficiency of aerial application often permits less
than 20 percent to reach the target area (Courshee 1960, Cope 1971). Further, due to
their appreciable vapor pressures, many pesticides also are subject to extensive volatilization
(Hamaker and Kerlinger 1969, Hartley 1969). A combination of these effects results in
the transfer of significant amounts into the atmosphere, as confirmed by analysis
(Risebrough 1968, Barney et al. 1971, Spencer and Cliath 1972), although their ultimate
fate remains unknown.

The recognized instability of many pesticides to light (Crosby 1969, Crosby and Li
1969, Crosby 1972) suggests that atmospheric photodecomposition could be important
to that fate. However, little information exists on the vapor-phase photochemistry of
these compounds; Nagl et al. (1970) reported that the irradiation of dieldrin vapor with
ultraviolet (UV) light provided photodietdrin as the only transformation product, Vollner
et al. (1971) described the similar irradiation of chlordane, and Kerner et al. (1972)
showed that DDE vapor decomposed in UV light.

Several authors (Stephens and Burleson 1967, Altshuller e t aL 1970, Doyle 1970,
Laity 1971) have described laboratory apparatus for investigating photochemical
reactions under simulated tropospheric conditions, but the principal drawback generally
has been the ever present possibility of unrecognized walt reactions. This paper describes
a simple vapor-phase photoreactor which permits compensation for wall effects, and its
application to the photodecomposition of the insecticides aldrin and dieldrin.

Archives of Environmental Contamination 62

and Toxicology, Vol. 2, No. 1, 1974
© 1974 by Springer-VerlagNew York Inc.
 Vapor-phase Photodecomposition of Aldrin and Dieldrin 63

Materials and m e t h o d s
Chemicals. ALDRIN (1,2,3,4,10,10-hexachloro- 1,4,4a,5,8,8a-hexahydro- 1,4-endo,
exo-5,8-dimethanonaphthalene, I), mp 104°C, was used as received from Shell Develop-
ment Co., Modesto, Calif.

DIELDRIN (1,2,3,4,10,10-hex achloro-6,7-epoxy-1,4,4a,5,6,7, 8,8a-octahydro- 1,4-

endo,exo-5,8-dimethanonaphthalene, II) was provided by the Shell Development Co.,
Modesto, Calif., and recrystallized from hexane to greater than 99.9 percent purity as
determined by gas-liquid chromatography (glc), mp 174-175°C [Spencer (1968) reports
175-176°C1.

PHOTOALDRIN (1,1,2,3,3a,7a-hexachloro-2,3,3a,3b,4,6a,7,7a-octahydro-2,4,7-meth-
eno-lH-cyclopenta[a] pentalene, III) was prepared by the method of Rosen and Carey
(1968) and was recrystallized from hexane until homogenous to glc, mp 186-187°C.

PtlOTODIELDRIN (1,t ,2,3,3 a,7a-hexachloro-5,6-epoxy-decahydro-2,4,7-methano-tH-

cyclopenta[a] pentalene, IV) was provided by J. D. Rosen, Rutgers University, and
was recrystallized from hexane until homogeneous to glc, mp 192°C [Benson (1971)
reports 192°C].

Analysis. Reaction products were identified by combined gas chromatography-mass

spectrometry (GC-MS). GC-MS employed a Finnegan Model 3000 Peak Identifier
equipped with a 5 ft × 1/8 in. id glass column containing 2%OV-1 on 60/80 mesh acid-
washed, DMCS-treated Chromosorb G (Perco Supplies, San Gabriel, Calif.). The initial
column temperature was 180°C, final column temperature 250°C, program rate t0°C
per min; injection port temperature 240°C; detector temperature 240°C; helium carrier
gas, flow rate 16 ml/min. As each compound eluted, its mass spectrum was recorded and
identification was achieved by comparison of its spectra with those of authentic
specimens.

For quantitative analysis, a Varian Model 1400 gas chromatograph was equipped with
an electron-capture detector and a 5 ft × 1/8 in. id glass column containing 2% OV-t as
described above. The column temperature was 200°C, injection port 250°C, detector
220°C, nitrogen carrier gas at 40 ml/min. Analytical values were read from a linear
standard curve with a maximum sensitivity of 1 ng and quantitative recovery.

Photoreactor design. The photoreactor is shown schematically to scale in Figure 1 ; its

stand and other construction details have been omitted for simplicity. The reaction
chamber (A) was a 72 liter borosilicate glass flask whose outer surface was painted dull
black. An unpainted circular area, 15 cm in diameter, was located opposite the mouth of
the flask to permit the beam of light to leave the chamber. The light-shield (B), a 33 cm
(diameter) cylinder open at one end and also painted black, housed the UV source and
collimator.

The collimator (C) was a 30-cm section of 59-mm id borosilicate glass tubing painted
dull black on both the inner and outer surfaces and provided a light beam approximately
64 D . G . Crosby and K. W. Moilanen

27 cm2 in area. A 3-mm-thick borosilicate glass disc was bonded over the end within the
reactor to prevent escape of vapor and filter out UV wavelengths below about 300 nm.
The removable light-trap (D) was a 15.5-cm (diameter) cylinder which could be replaced
with a 13-cm (diameter), one-liter spherical flask silvered on its interior surface.

Inlet and outlet tubes (5 mm od glass) provided vents to the outside of the reactor,
circulated air or other gas, and provide a convenient means to remove volatile products to
an absorption train. The tubes were used only as vents in the experiments described here.

For calibration, the light source (E) was a 100 W filtered low-pressure mercury arc
lamp (H100-PSP44-4 Reflector Spot, General Electric Co., Schenectady, N.Y.)(Table I).
The other experiments employed a 275 W RS-sunlamp (General Electric).

Cafibration. Total light energy was measured with a YSI-Kettering Radiometer (Yellow
Springs Instrument Co., Yellow Springs, Ohio), or an Eppley Pyranometer (Eppley
Laboratories Inc., Newport, Rhode Island), at points a, b, c, d, e, and f (Figure 1), first
with the light-trap in place and then with the spherical reflector touching the rear wall o f
the reactor.

Procedure. Dieldrin (5 mg) was dissolved in 2-3 ml of redistilled hexane, the solution
placed on a 48-ram watch glass, and the solvent evaporated in a current of air to leave a
thin solid film. The dry watch glass was placed at the bottom of the reaction chamber
and warmed to 35°C with a small heating mantle placed under the reactor.

3
1 i

12-W'
31-¼"

Fig. 1. Schematic diagram of vapor-phase photoreactor.

 Vapor-phase Photodecomposition of Aldrin and Dieldrin 65

Table I. Spectral Energy Distribution of Light Sources

Rated Energy distribution (W) in spectral range (nm)

Source power (W) 300-320 320-360 360-400 400-700

Sunlight a - 0.455 2.42 3.65 45.2

RS-Sunlamp 275 1.22 0.37 2.70 7.03

Mercury arch 100 0.066 0.188 1.32 6.26

Fluorescent UV c 40 0.33 3.32 3.99 2.64

aKoller, 1965.
bG.E. H100-PSP44.
CG.E. F40-BL.

After several hours to allow the dieldrin vapor to saturate the air in the chamber,
irradiation was commenced. Photolysis was allowed to proceed for an arbitrary period
(Tables IV and V) at 25-30°C, after which the reactor was dismantled and rinsed with
four 500-ml portions of redistilled hexane. The rinses were combined, reduced to small
volume on a rotary evaporator, and analyzed by glc. Dieldrin eluted at 238°C and photo-
dieldrin at 250°C; the detected compounds exhibited mass spectra identical with those
of standards. No other products were detected.

Another experiment was conducted simultaneously in an identical reactor for which

the light trap had been replaced with the spherical reflector, and a dark control was
included in yet another flask. All products were identified and analyzed in an identical
manner.

Aldrin, photoaldrin, and photodieldrin were investigated in the same way.

Results and discussion

The products and rates of many vapor-phase reactions are dependent upon the size
and nature of the reaction vessel (Rice and Herzfeld 1951, Pollorak and Voevodskii 1958,
Voevodskii t959). Certain steps in the overall reaction occur chiefly on the reactor walls
(the "wall reaction") making rates dependent upon both the surface and surface/volume
ratio. Even the identity and composition of the products may be altered (Raley et al.
1948).

Wall reactions commonly are measured by increasing the effective surface area of the
reactor, e.g., by addition of glass rods, or by changing the materials of construction
(Frost and Pearson 1961); if reaction rates and products are not affected, the process is
considered to take place in the gas phase. The present experiments examined wall effects
66 D.G. Crosby and K. W. Moilanen

by varying the intensity of the light impinging on the inner surface of the reaction
chamber in relation to irradiation of the vapor.

For the initial calibration of the photoreactor, the Filtered low-pressure mercury arc
spotlight was chosen for convenience, intensity, and its previous widespread use in ex-
perimental photochemistry. Its spectral energy distribution, represented by the cross-
hatched bands in Figure 2, showed only a superficial resemblance to those of sunlight
(curve D) or the fluorescent blacklight (curve C) used in previous photochemical investiga-
tions of pesticides (Crosby 1969) and in atmospheric simulation (Laity 1971). However,
the highly energetic Hg emission at 254 nm (band A) and other UV wavelengths shown to
be absent from normal sunlight would be removed effectively by the borosilicate glass
window of the lamp (transmission curve B) as well as the filter on the collimator. The
vapor-phase photodecomposition of atdrin was conducted with an RS-sunlamp of
similar wattage but more satisfactory spectral-energy distribution compared to sunlight.
The spectral energy distribution of the RS-sunlamp is represented by the area under the
bold line in Figure 2.

1200 - -

1000

800
A
E
t-
O
"7,

E 600

400

200

250 300 350 4OO 450

Wavelength (rim)

Fig. 2. Spectral energy distributions for various light sources.

 Vapor-phase Photodecomposition of Aldrin and Dieldrin 67

The energy entering the chamber from the arc spotlight (Table II) was reduced 20-fold
by spreading and passage through the uncoated reactor wall, but no detectable radiation
( ~ 20 #W/cm 2) was scattered to the walls at right-angles to the beam. The spherical re-
flector produced 90 /~W/cm2 at the same point (reduced from the calculated value of
133 /aW/cm 2 largely by the imperfect mirror and four more passages through glass),
obviously far more than enough to compensate tot any stray light reaching the walls
during the irradiation of vapor.

Dieldrin was chosen as the model because o f its known volatility, photodecomposition
to a single readily identified product (photodieldrin) (Nagl et al. 1970), and widespread
presence in the environment. Its accepted vapor pressure (Spencer and Cliath 1969)
assured that air saturated with dieldrin at ambient temperatures would contain easily
detectable amounts (Table III). Dieldrin vapor was stable in the dark (Tables IV and V),
and no electron-capturing artifacts interfered with the analysis (Figure 3). However,
mercury-arc irradiation resulted in appreciable formation of photodieldrin; subsequent
reflection of the beam onto the reactor wall gave no appreciable change in the amount or
nature of the product.

The irradiation of dieldrin at saturation levels with the RS-sunlamp produced very
similar results (Table V), and a separate irradiation of photodieldrin revealed it to be en-
tirely stable under these conditions. The subsequent irradiation of saturated aldrin vapor

Table II. Calibration o f the Photoreactor

Radio meter Observed Calculated energy

location #W/cm 2 ktW/cm2

a 4.48 X 104 -

b 4.00 X 104 4.13 X 104

c 1.95 X 103 -

d1 100 %0

d2 180 133

eI <20 %0

e2 85 133

fi < 20 ",, 0

f2 90 133

1Without reflector.
2With :reflector.
68 D . G . Crosby and K. W. Moilanen

resulted in photoaldrin and dieldrin, but in this instance the level of photodieldrin
probably was below the detection limit. In no case was a dark reaction observed, and
irradiation of the wall provided no unusual results. These photodecomposition reactions
are summarized in Figure 4.

When aldrin was irradiated at levels well below saturation (14 ~g/m3), dieldrin was
the major photoproduct while photoaldrin and photodieldrin were detected at nanogram
levels (Table VI) and then only at a column temperature of 230°C. Small amounts of the
same electron-capturing impurities were present in both the irradiation mixture and the
dark control, indicating the contamination problems expected at these low levels. The
combined amount of recovered aldrin and dieldrin was close to the calculated value, so
any other photoproducts necessarily were present in only minute quantities.

Table IlL Volatility of Aldrin and Dieldrin

Vapor pressure Saturation conc. Reactor capacity

torr ng/1 /ag of vapor

Aldrin

6.0 X 10 - 6 (25°C) 118 8.5

Dieldrin

2.8 X 10 - 6 (20°C) 59.7 4.3

10.1 X 10 - 6 (30°C) 206 14.8

33.9 X 1 0 - 6 (40°C) 660 47.5

Table IV. Vapor-PhasePhotolysisofDieldrin

with the Mercury Arc Lamp

Recovered
Time (days) Light Reflector dieldrin (/zg) Photodieldrin (/~g)

4 No - t2 < 0.5

24 No - 70 < 0.5

12 Yes No 34 4.4

t2 Yes Yes 32 4.0

 Vapor-phase Photodecomposition of Aldrin and Dieldrin 69

Table V. Photodecomposition Experiments with the RS-Sunlamp

Amount Products recovered b (#g)

Irradiated irradiated Photo- Photo-
compound Conditions a (mg) Aldrin aldrin Dieldrin dieldrin

Aldrin A, 45 hrs 5.0 3,300 30 60

B, 45 hrs 5.0 4,300 20 50
C, 45 hrs 5.0 3,200

Dieldrin A, 91 hrs 0.5 300 30

B, 91 hrs 0.5 290 28
C, 91 hrs. 0.5 400

Photoaldrin A, 65 hrs. 2.0 1,900 20

B, 65 hrs 2.0 1,700 20
C, 65 hrs 2.0 1,100

Photodieldrin A, 65 hrs 3.0 2,600

B, 65 hrs 3.0 2,400
C, 65 hrs 3.0 2,300

a A denotes the irradiation utilizing the light trap.

B denotes the irradiation utilizing the spherical mirror.
C denotes the dark control.
b Refers to the amount of products recovered from the wall of the reactor.

Dieldrin

iPhotodieldrin
-$
c~

er

~ L"~--~I~-----Lighttrap

_ J I I I l
2 4 6
Retentiontime(min)
Fig. 3. GLC profiles illustrating the conversion of dieldrin to photodieldrin.
70 D.G. Crosby and K. W. Moilanen

Cl Cl

CI ) Cl

Cl CI
Cl Cl
t II

CI Ct

CI CI

>
el
Ct CI
III IV
Fig. 4. Vapor-phase photochemical transformations of aldrin, dieldrin, and photoaldrin.

Table VI. Vapor-Phase Photolysis o f 1 #g o f A Mrin with the RS-Sunlamp

Products detected (/./g)

Aldrin Dieldrin Photoaldrin Photodieldrin

Dark control 0.84 0.14 < 0.004 <( 0.004

Irradiated sample 0.40 0.63 0.02 0.02

Irradiation Time: 168 hr.

Conclusion
Both aldrin and dieldrin have been reported to occur in the ambient air over agricul-
tural communities. For example, Tabor (I 966) reported #g/m3 levels, while Barney et al.
(1971) showed levels of only a few ng/m3. Both compounds are quite volatile (Lichten-
stein et al. 1968), and the widely observed conversion of aldrin to dieldrin in soil (Lichten-
stein and Schulz 1959, 1965) also could provide the latter to the atmosphere even in
areas where it had not been applied.

However, the oxidation of aldrin in the atmosphere has not been reported; aldrin and
dieldrin have not been found together in air samples. Metabolic conversion in plants,
animals, and microorganisms (Menzie 1969) and most laboratory methods of
oxidation involve ionic mechanisms, e.g., hydroperoxides (Lidov et al. 1950), not
 Vapor-phase Photodecomposition of Aldrin and Dieldrin 71

applicable to vapor-phase reactions. The tbnnation of dieldrin from aldrin by Fenton's

reagent (HO radicals) in solution (Marshall and Wilkinson 1970) suggests that a free-
radical oxidation is possible, although the necessity for serum protein in those experi-
ments again could be indicative of ionic oxidation processes. The vapor-phase conversion
of aldrin to dieldrin seems more likely to involve direct combination with oxygen,
perhaps in its excited singlet state (Crosby 1973).

The isomerization of both aldrin and dieldrin under the influence of UV light is welt
known (Parsons and Moore 1966; Rosen and Sutherland 1967),but remains mechanistically
unexplained. Whether isomers or dechlorinated compounds result from irradiation
depends upon the reaction medium, concentration, and wavelength of light (Henderson
and Crosby 1967, Rosen and Carey 1968, Benson 1971).

Despite the report of Nagl et al. (1971), isomerization in the vapor-phase has not been
unequivocally demonstrated previously, and the occurrence of photoaldrin or photo-
dieldrin in the atmosphere has not been reported. The surprisingly low yield of these
substances during irradiation of dilute vapor might be due to the need for a sufficient
concentration of some coreactant or sensitizer (Rosen and Carey 1968, Ivie and Casida
1971, Lykken 1972). Although a number of reaction products were reported to occur
during the irradiation of dieldrin vapor in the presence of nitrogen oxides or ozone (Nagl
and Korte 1972), nothing other than the several expected compounds were observed
during our experiments.

Obviously, the present work cannot be presumed to accurately represent atmospheric

conditions in the environment. Atmospheric levels of aldrin and dieldrin generally lie
well below our operating concentrations; particulate matter is excluded, although it may
be important in atmospheric reactions; the present irradiations were of limited duration
while exposure to UV light in the real world could be extensive enough to ensure opera-
tion of even very slow reactions; and the existing lamps still are not ideal for sinmlation
of sunlight.

However, this work has demonstrated the utility of a versatile and inexpensive vapor-
phase photoreactor which minimizes interfering wall reactions. With this reactor, we have
shown the anticipated photooxidation of aldrin vapor to dieldrin, which now should be
verified by field experiments. The expected facile atmospheric conversion of aldrin and
dieldrin to their more toxic photoisomers has been opened to serious question, although
the seeming stability of these products in the air should make their precipitation and
eventual fate in condensed environmental phases a matter of increased interest.

Acknowledgments

We thank Michael Hardesty, Gary Nakamura, Clayton Reece, and Michael Riley for
technical assistance in various aspects of this investigation. This research was supported,
in part, by USPHS Research Grant ES-00054, USDA Regional Research Project W-45,
and NSF Grant GB-33723X.
72 D. G. Crosby and K. W. Moilanen

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Presented at the Division of Pesticide Chemistry, 163rd Meeting, ACS, Aprit 11,
t972, Boston, Mass.

Manuscript received July 12, 1973; accepted for publication October 2, 1973