Phenol

108-95-2

Solvent. 
Produced by cumene oxidation and is used as an
intermediate in the manufacture of a wide range of important
chemicals including phenolic resins, bisphenol-A, caprolactam,
alkylphenols and adipic acid. 
Disinfectant.

Colourless to brown-black.

Colourless, acicular crystals or white, crystalline mass.

Threshold odour concentration in water: 1.0 - 7.5 mg/l
(Fawell & Hunt 1988).

Odour: characteristic, medicinal, sickening sweet and acrid
with a sharp and burning taste (Verschueren 1983).

Human odour perception: non perception: 0.022 mg/m3;
                        perception: 0.184 mg/m3;
human reflex response: adverse response: 0.015 mg/m3;
animal chronic exposure: no effect: 0.01 mg/m3;
                         adverse effect: 0.1 mg/m3
(Verschueren 1983).

Odour index: 16 at 20 °C (Verschueren 1983).

Sweet tarry odor. 
Sweet acrid odor. 
Has distinct, aromatic, 
somewhat sickening sweet and acrid odor. 
When perfectly pure 
phenol is devoid of odor of cresol, but it has peculiar
aromatic odor which is not disagreeable (HSDB 1998).

94.12

Despite its moderate vapor pressure, phenol has a low Henry's
Law constant and a low rate of evaporation from water. 
The
estimated half-life for evaporation from water is 3.2 months
(Branson 1978) (Shen 1982).

Using the Henry's Law constant, a half-life of 88 days was
calculated for evaporation from a model river 1 m deep with a
current of 3 m/sec and with a wind velocity of 3 m/sec
(Lyman et al. 1982).

Volatilization from near-surface soil should be relatively
rapid due to its moderate vapor pressure (Howard 1989).

The Henry's Law constant of phenol is 3.33x10-7 atm-m3/mole. 

Based this Henry's Law constant, the volatilization half-life 
from a model river (1 m deep, flowing 1 m/sec, wind velocity of
3 m/sec) is estimated to be 107 days (HSDB 1998).

Low adsorptivity to clay soils and silt loam is reported
(Artiola-Fortuny & Fuller 1982).

Koc values for two silt loams are 39 and 91 (Scott et al. 
1983).

No adsorption to aquifer material was observed (Ehrlich et al 
1982).

Using the log Kow, an estimated Koc of 148 was calculated 
(Lyman et al. 1982).

soil                      pH   organic matter  Koc
Brookstone clay loam      5.7        5.1       16
Captina silt              5.7        1.1       91
Palouse silt              5.7        3.6       39
(HSDB 1998).

The Koc for phenol to a Batcombe silt loam soil (pH 6.7,
organic carbon 2.51 %) was 30 (HSDB 1998).

2.83 % (air), 96.17 % (water), 1.00 % (sediment).

Equilibrium distribution:
        mass %
air      1.05
water   98.47
solid    0.48
(Anon 1988)

Based on the reported and estimated Koc, phenol will be
expected to exhibit high to very high mobility in soil (Swann
et al. 1983).

The pKa of phenol is 9.99, indicating that it will be partially
dissociated at the upperend of environmental pH range and its
mobility may be pH dependent (HSDB 1998).

Very soluble in alcohol, chloroform, ether, glyserol, carbon 
disulfide, volatile and fixed oils, aquatic alkali hydroxides.

Phenol absorbs light in region 290 - 330 nm and therefore might
directly photodegrade (Howard 1989).

Phenol's estimated half-life by reaction with hydroxyl radicals
in air is 0.61 days (Hendry & Kenley 1979).

Atmospheric photolysis half-life:
7.2d - 1.9d, based upon reported half-lives for photolysis
under sunlight for phenol in distilled water in summer (low
t1/2) and winter (high t1/2) (Howard 1991).

Photooxidation half-life in air:
22.8hr - 2.28hr, based upon measured reaction rate constant for
OH with phenol (Howard 1991).

The rate constant for the vapor-phase reaction of phenol with 
photochemically produced hydroxyl radicals is 2.63x10-11 
cm3/molecule at 25 °C. 
This corresponds to an atmospheric 
half-life of 14.6 hours at an atmospheric concentration of 
5x10+5 hydroxyl radicals per cm3 (HSDB 1998).

Photooxidation by UV-light in aqueous medium at 50 °C: 10.96 %
degradation to CO2 after 24 hr (Verschueren 1983).

Natural sunlight causes degradation in water (Callahan 1979).

Phenol has also been shown to inhibit oxidant formation both in
air and in water (Gitchell et al. 1974) (Draper & Crosby 1983).

The estimated half-life for reaction of phenol with
photochemically produced singlet oxygen in surface waters
contaminated by humic substances is 83 days (Scull & Hoigne 
1987).

As a class, phenols react relatively rapidly in sunlight natural
water via reaction with photochemically produced hydroxyl
radicals and peroxy radicals; typical half-lives for hydroxyl
and peroxyl radical reactions are on the order of 100 and 19.2
hr of sunlight, respectively (Mill & Mabey 1985).

Aquatic photolysis half-life:
7.2d - 1.9d, based upon reported half-lives for photolysis
under sunlight for phenol in distilled water in summer (low
t1/2) and winter (high t1/2) (Howard 1991).

Photooxidation half-life in water:
160d - 3.2d, scientific judgement based upon reported reaction
rate constants for RO2. with the phenol glass (Howard 1991).

AEROBIC DEGRADATION IN SOIL
Maximum adsorption wavelength: 271 nm
NON-STERILE SOIL
Minimum time for >70% decrease: 0.50 - 1.00 d
% decomposition at the termination of the experiment:  5d, 100%
STERILE SOIL
% decomposition at the termination of the experiment:  40d, 15%
(Baker et al. 1980)

Percent mineralization in an alkaline, para-brown soil under
aerobic conditions was 45.5%, 48% and 65% after 3,7 and 70
days, respectively. 
(Haider et al. 1974)

ANAEROBIC DEGRADATION IN SOIL
Maximum adsorption wavelength: 271 nm
NON-STERILE SOIL
% decomposition at the termination of the experiment:  40d, 20%
STERILE SOIL
% decomposition at the termination of the experiment:  40d,  7%
(Baker et al. 1980)

Biodegradation to CO2 in estuarine water:

conc.   month     incubation  degradation rate   turnover time
µg/l              time (hr)   (µg/l/day) x 1000   (days)

5       January    24         270                  18
10      January    24         550                  18
5       March      24         100                  25
10      June       24         580                  17
(Verschueren 1983).

Aerobic half-life:
3.5d - 0.25d, scientific judgement based upon aerobic river 
die-away study data (high t1/2) and lake die-away study data 
(low t1/2) (Howard 1991).

Anaerobic half-life:
28d - 8d, scientific judgement based upon aqueous anaerobic 
screening studies (Howard 1991).

Decomposition rate in soil suspension: 2 days for complete
disappearance (Verschueren 1983).

Degradation in soil is completed in 2 - 5 days even in
subsurface soils (Baker & Mayfield 1980).

Half-lives for degradation of low concn of phenol in 2 silt
loam soils were 2.70 and 3.51 hr (Scott et al. 1983).

Complete degradation in <1 day in water from 3 lakes; rates
increace with increase concn phenol and increase tropic levels
of water; rate affected by concn of organic and inorganic
nutrients (Rubin & Alexander 1983).

Complete removal in river water after 2 days at 20°C and after 4
days at 4°C (Ludzack & Ettinger 1960).

Degradation is somewhat slower in salt water and a half-life of
9 days has been reported in an estuarine river (Lee & Ryan 
1979).

Biodegradation:
85% by BOD
period: 14d
substance: 100 mg/l
sludge: 30 mg/l
(MITI 1992)

Confirmed to be biodegradable (Anon. 1987).

Impact on biodegradation processes:
inhibition of degradation of glucose by Pseudomonas
fluorescent: 70 mg/l; inhibition of degradation of glucose by
Escherichia coli: > 1000 mg/l; inhibition of the nitrification
process in non adapted activated sludge from 5.6 mg/l upwards
(Verschueren 1983).

Inhibition of cellulose degradation
by natural soil populations            at 17 hr     at 200 hr
 500 ppm phenol                        72 %           44.0 %
1000 ppm phenol                        97.6 %         56.5 %
1500 ppm phenol                        98.4 %         60.3 %
5000 ppm phenol                        98.7 %         99.5 %

inhibition of starch degradation
by natural soil populations            at 20 hr      at 140 hr
 500 ppm phenol                        41 %          40.3 %
1000 ppm phenol                        96 %          52.7 %
1500 ppm phenol                        97.4 %        85.1 %
5000 ppm phenol                        98.4 %        98.4 %
(Verschueren 1983).

*--------------------------------------------------------------*
ENVIRONMENT  INIT.CONC   REDOX-        TEMP  DEGRADATION  REF.
             mg/l        COND.         °C     %/day
*--------------------------------------------------------------*
water        20          aerobic       25      99/7        a
water         5          aerobic       25      96/7        b
water        10          aerobic       25      97/7        b
water (adapted) 5        aerobic       25     100/7        b
water  0.0001 - 0.001    aerobic       29      80/10       c
groundwater 30 - 50      sulfate reducing room 99/90       d
groundwater 30 - 50      methanogen    room   100/90       d
lake sediment    30 - 50 anaerobic     room   100/90       d
activated sludge 30 - 50 anaerobic     room   100/90       d
activated sludge appr. 50 anaerobic    35      91/14       e
soil suspension  10 - 100 aerobic      30     100/2        f
soil suspension  25      aerobic       25     100/1        g
soil              1      aerobic       23     100/5        h
soil              1      anaerobic     23      20/40       h
sterile soil      1      aerobic       23      15/40       h
sterile soil      1      anaerobic     23       7/40       h
soil            258      aerobic       20     >99/3        i
*--------------------------------------------------------------*
a) Bunch & Chamber 1967 b) Tabak et al. 1981 c) Subba-Rao et al.
1982 d) Gibson & Suflita 1986 e) Horowitz et al. 1982
f) Alexander & Aleem 1961 g) Alexander & Lustigman 1966
h) Baker & Mayfield 1980 i) Lųkke 1984 (Anon. 1987b).

Phenol is readily absorbed by all routes, though it is rapidly
conjugated with either sulfate or glucuronic acid, followed by
elimination in the urine. 
Small quantities of oxidative
metabolites such as catechol, hydroquinone and benzoquinones
can be formed. 
Such metabolites have been suggested to be
involved in the hematotoxicity of benzene, though phenol does
appear to have much weaker activity than benzene in this
respect (Fawell & Hunt 1988).

Bioconcentration factor (crustaceans):
277, Daphnia magna (Dauble et al. 1981).
  
Bioconcentration factor (algae):
200, Chlorella fusca (Freitag et al. 1984).
3.5, Scenedesmus quadricauda (Hardy et al. 1985)

The BCFs reported in aquatic organisms include:
goldfish (Carassius auratus) 1.9 
fish (unspecified) 17 
water flea (Daphnia magna) 277
algae (Clorella fusca) 200
freshwater phytoplankter (Scenedesmus 
quadricauda) 3.5. 
Phenol was rapidly eliminated from goldfish 
and therefore would be unlikely bioaccumulate
(HSDB 1998).

Skin and eye irritation data:
skin, rabbit, 500 mg, 24 hr, severe;
skin, rabbit, 535 mg open, severe;
skin, rabbit, 100 mg, mild;
eye, rabbit, 5 mg, severe;
eye, rabbit, 100 mg rinse, mild (Sweet 1987).

Man: oral, ingestion, 1000 mg dose may be lethal (Verschueren
1983).

NCI carcinogenesis bioassay completed: results negative;
mus,rat (Lewis & Sweet 1984).

NCI carcinogenesis bioassay (oral); no evidence; mouse, rat
(Sweet 1987).

Does not appear to be mutagenic in the Ames test, but has given
positive results in some higher test systems (Fawell & Hunt
1988).

Mutation data:
cyt, fish, multiple, 300 nl/l;
dnd, mam, lym, 250 mmol/l;
DNA inhibition:
hmn, fbr, 10 mmol/l;
hmn, hla, 1 mmol/l;
mus, orl, 20000 mg/kg;
mus, lym, 0.8 mmol/l;
dns, rat, orl, 4000 mg/kg;
mma, sat, 0.040 mmol/plate;
sin, smg, ovr, 100 ppm;
sce, hmn, lym, 0.005 mmol/l (Sweet 1987).

LDLo, 290 mg/kg, par, frog;
LDLo, 75 mg/kg, scu, frog;
LDLo, 290 mg/kg, scu, frog (Sweet 1987).

Tanytarsus dissimilis, > 51.1 mg/l, LC50, 2 d (Holcombe et al.
1987).

Escherichia coli: > 1000 mg/l (Verschueren 1983).

Toxicity threshold (cell multiplication inhibition test):
bacteria (Pseudomonas putida): 64 mg/l
(Bringmann & Kühn 1980a)

Inhibition of photosynthesis of a freshwater, non-axenic
unialgal culture of Selenastrum capricornutum:
at 10 mg/l: 105 % carbon-14 fixation (vs. controls);
  100 mg/l: 92 %;
 1000 mg/l: 19 % (Verschueren 1983).

LC50, 96hr, 128.8 mg/l, Lymnea acuminata (Gupta & Rao 1982).

LC50, 4d, > 51.1 mg/l, Aplexa hypnorum (Holcombe et al. 1987). 
Branchydanio rerio, 4.9 mg/l, 27 d, 100 % mortality including
algicidal and herbicidal effects (Razani et al. 1986).

Toxicity threshold (cell multiplication inhibition test):
bacteria (Pseudomonas putida): 64 mg/l;
algae (Microcystis aeruginosa): 4.6 mg/l;
green algae (Scenedesmus quadricauda): 7.5 mg/l;
protozoa (Entosiphon sulcatum): 33 mg/l;
protozoa (Uronema parduczi): 144 mg/l (Verschueren 1983).

Chlorella pyrenoidosa, toxic, 233 mg/l (Verschueren 1983).

Lethal concentration:
rainbow trout: 5 mg/l, 3 hr;
perch: 9 mg/l, 1 hr
goldfish: 28.9 mg/l, 48 hr (Verschueren 1983).

Toxicity threshold (cell multiplication inhibition test):
green algae (Scenedesmus quadricauda): 7.5 mg/l
protozoa (Entosiphon sulcatum): 33 mg/l
(Bringmann & Kühn 1980a)

Reduction of amenities:
taste and odour of fish is affected at: 15 - 25 mg/l;
tainting of the flesh of fish and other aquatic organisms: 1 -
10 mg/l;
taste in trout and carp: 25 mg/l; 1.0 mg/l;
odour threshold: average: 5.9 ppm;
                 range: 0.016 - 16.7 ppm;
taste and odour threshold: (tentative): 0.15 mg/l;
organoleptic limit: 0.001 mg/l (Verschueren 1983).