Chrysene

218-01-9

Chrysene is used in organic synthesis. 
Chrysene occurs in coal
tar and is formed during distillation of coal and in very small
amounts during distillation or pyrolysis of many fats and oils. 
It is also found in exhaust grom gasoline and diesel engines, the
atmosphere, soil, water, cigarette smoke, petroleum
products, wood smoke, and foods.

Crystals. 
Red, blue, fluorescent.

Odourless.

228.2

Insoluble in water. 
Soluble in ethanol at 0.097 parts chrysene
/ 100 parts ethanol at 16 °C, and 0.17 / 100 parts ethanol at
78 °C. 100 parts toluene dissolves 0.24 parts chrysene at 18
°C, and 5.39 parts chrysene at 100 °C. 
Sparingly soluble in
glacial acetic acid, ether and carbon disulfide and slightly
soluble in hot benzene or xylene.

Sublimes easily in a vacuum. 
A partition coefficient for
chrysene was determined between the two solvent phased hexane
and aqueous monoethanolammonium desoxycholate to be 10.4 (Sax
1986).

Airborne particulate polycyclic aromatic hydrocarbons can
persist at relatively high concentrations in aerosols
transported for long distances. 
The atmosperic persistence is
longer than would be predicted from laboratory photooxidation
studies. 
On the other hand, the National Academy of Sciences
(1972) proposed that the chemical half-life of PAHs in the
atmosphere may be limited to hours or days (Sax 1986).

Photolysis half-life in air:
13hr - 4.4hr, based upon measured aqueous photolysis quantum 
yields and calculated for midday summer sunlight at 40°N 
latitude (low t1/2) and adjusted  for approximate winter 
sunlight intensity.

Photooxidation half-life in air:
8.02hr - 0.802hr, scientific judgement ased upon estimated rate 
constant for reaction with hydroxyl radical in air.

(Howard 1991)

Aquatic photolysis half-life:
13hr - 4.4hr, based upon measured aqueous photolysis quantum 
yields and calculated for midday summer sunlight at 40°N 
latitude (low t1/2) and adjusted for approximate winter 
sunlight intensity.

Ozone and chlorinating agents oxidize polycyclic aromatic
hydrocarbons to quinones, diacids, and nuclear and side-chain
oxidation products. 
Chlorinating agents also produce
chlorine-substituted derivatives. -  
The most common
photooxidation product in solution is an endo peroxide.

Dealkylation, ring cleavage, and other reactions ensue
following photolysis or pyrolysis of these peroxides.

Frequently, only quinones are isolable. 
Photodimers may result
in some cases. 
Absorbed PAH's are more reactive than in
solution (Sax 1986).

Aerobic half-life:
2.72yr - 1.02yr, based upon aerobic soil die-away test data 
(Howard 1991).

Anaerobic half-life:
11yr - 4.06yr, scientific judgement based upon estimated 
unacclimated aqueous aerobic biodegradation half-life (Howard 
1991).

PAHs deposited in sediments are less subject to photochemical or
biological oxidation, especially if the sediment is anoxic. 
Sedimentary PAH is therefore quite persistent and may
accumulate to high concentrations (Sax 1986).

Biodegradation may be less slow in the soil than in aquatic
systems. -  
Oxidation of any PAH by chlorine and ozone, when
used for the disinfection of drinking water, forms quinones. -

Chlorinating agents will also produce chlorine-substituted PAHs
as well as oxidation products. -  
The half-life for the
reaction of all PAHs with chlorine is less than 0.5 hour. -

Hydrolysis is not significant. 
Photolysis in an aquatic
environment may be an important fate process, especially for
the dissolved portion. 
The half-life for chrysene photolysis
calculated for surface waters in midsummer at 40 degrees north
latitude was 4.4 hr. -  
Evaporation of lower-molecular-weith
PAHs may be significant only in a clear, rapidly flowing
shallow stream. -  
Movement via sediment is considered to be an
important transport process for PAHs. 
An exchange equilibrium
exists in natural water systems between absorbed and soluble
PAHs. 
Although the particulate form if favored, a significant
fraction of the PAH will be dissolved except in systems that
are very heavily contaminated by PAHs. -  
However, chrysene was
found to be more resistant to microbial degradation than 6
other PAHs having 3 to 5 aromatic rings. -  
The concentrations
of bacteria and fungi capable of oxidizing hydrocarbons are
extremely low in all but heavily polluted fresh and marine
waters. 
Most species cannot use PAHs as a sole carbon source.

Microbial oxidation of PAHs requires oxygen and will not
proceed in anoxic sediments or water (Sax 1986).

There are large differences among species in their ability to
absorb and assimilate PAHs from food. 
Polychaete worms have a
very limited ability, fish show limited and variable absorption
from the gut, and crustaceans readily assilimate PAHs.

Assimilated PAHs are metabolized and excreted rapidly. 
For
biomagnification to occur, a substance must be relatively
resistant to metabolism or exreation (Sax 1986).

The estimated steady-state bioconcentration factor for aquatic
organisms containing 7.6 % lipids is 11700. 
Although polycyclic
aromatic hydrocarbons are rapidly bioaccumulated, those
containing 4 or fewer aromatic rings may also be rapidly
metabolized by multicellular organisms. 
Bioaccumulation is
considered to be short-term. -  
In most cases, PAHs are less
bioavailable when complexed to colloidal organic materials or
adsorbed to organis or inorganic particulated then when in
solution or in fine dispersion in water. 
For example, the
deposit-feeding clam Tacoma inquinata exhibited bioaccumulation
factors of 0.04 and 694 when exposed for 7 days to chrysene in
contaminated sediments and seawater, respectively. -  
The
long-lived and pollution-tolerant freshwater mollusc
Cipangopaludina chinensis (a snail), which is a mucociliary and
bottom feeder, showed a bioaccumulation factor of approximately
100 for chrysene in its soft tissues (dry weight basis)
compared to the chrysene concentration in the dry sediment from a
marsh in a highly populated area. -  
A bioaccumulation factor
of 8.2 was reported for chrysene by the estuarine clam Rangia
cuneata when exposed ot 0.066 ppm for 24 hr. 
After 24 hr in
clean water, 26 % of the chrysene had been released. -  
Pink
shrimp Penaeus duorarum was exposed to 0.001 or 0.005 ppm
chrysene in seawater. 
Highest concentrations after 28 days were
in the cephalothorax and abdomen. 
They released most of the
chrysene in 10 days after returning to clean seawater, but
small amounts still remained after depuration fo 28 days (Sax
1986).

Polycyclic aromatic hydrocarbons can presumably be absorbed
from ingestion, inhalation and skin contact. 
Chrysene is a weak
carcinogen (Sax 1986).

In mice, chrysene caused skin tumors after dermal exposure at
high concentrations. it was also an initiator in skin
carcinogenesis. 
A low incidence of tumors occurred after scu
injection at high doses in mice. -  
Chrysene is a carcinogenic
suspect agent (Sax 1986).

Mutagen data:
mma, sat, 0.010 mg/plate;
msc, hmn, lym, 0.006 mmol/l;
msc, mus, orl, 450 mg/kg;
otr, ham, kdy, 0.025 mg/l;
otr, ham, emb, 5 mg/l;
dnd, ham, emb, 1 mg/l;
sce, ham, ipr, 900 mg/kg, 24 hr (Sax 1986).

In the Salmonella test: positive
38 revertant colonies/nmol
1670 revertant colonies at 0,01 mg/plate
(Mc Cann et al. 1975)

Neanthes arenaceodentata, 96hr, LC50, > 1 mg/l (Sax 1986).

Polychlorinated PAHs are probably highly toxic to aquatic
organisms and persistent in the environment as are
polychlorinated biphenyls and polychlorinated naphthalenes.

Chlorination for purification of wastewaters or drinking waters
containing high concentrations of PAHs may not be advisable.

Activated sludge treatment is unable to oxidize PAHs within
normal retention times (Sax 1986).

Daphnia magna; lethal threshold concentration, 1 day,
0.0007 mg/l (Newsted & Giesy 1987).