Iodine and Iodine Compounds

PHYLLIS A. LYDAY, U.S. Bureau of Mines, Washington, DC, USA

TATSUO KAIHO, Godo Shigen Co., Ltd., Tokyo, Japan

1. Introduction . . . . . . . . . . . . . . . . . . . 1 7. Uses . . . . . . . . . . . . . . . . . . . . . . . . . 5
2. Physical Properties . . . . . . . . . . . . . . 1 8. Economic Aspects . . . . . . . . . . . . . . . 8
3. Chemical Properties. . . . . . . . . . . . . . 2 9. Inorganic Iodine Compounds . . . . . . . 9
4. Occurrence . . . . . . . . . . . . . . . . . . . . 3 10. Organic Iodine Compounds . . . . . . . . 10
5. Production . . . . . . . . . . . . . . . . . . . . 4 11. Toxicology and Occupational Health . 11
6. Quality Specifications, Transportation, References. . . . . . . . . . . . . . . . . . . . . 12
and Storage. . . . . . . . . . . . . . . . . . . . 5

1. Introduction new element. GAY-LUSSAC named the substance

“iode” after the Greek word for violet-colored.
Iodine, I [7553-56-2], atomic mass 126.9044, In 1814 GAY-LUSSAC published the results of his
atomic number 53, a nonmetallic element of the investigations in Mémoire sur l’Iode.
halogen family, appears in group 17 of the
periodic table between bromine and astatine.
The electronic configuration of the iodine 2. Physical Properties
atom is [Kr]4d105s25p5. The relative atomic
mass of the only stable isotope of iodine is Iodine is the first member of the halogen family
127. There are 22 artificial isotopes with masses that is solid at ambient temperature. Iodine
between 117 and 139, and fourteen of these vapor exhibits fluorescence at low pressure,
yield significant radiation, 122I through 123I and emitting a yellowish green light when illumi-
126
I through 136I (→ Radionuclides, 2. Radio- nated by sunlight or the light from an electric
active Elements and Artificial Radionuclides). arc. It also rotates the plane of polarized light
The half-lives of the isotopes vary; 136I, has the when placed in a magnetic field between
shortest half-life of 86 s, and 129I, has the longest crossed Nicol prisms, and is thermoluminescent
half-life of 1.6 × 107 a. The isotope 129I is a above 500 °C. Some physical properties of
product of the fission of 235U with slow neu- iodine are as follows:
trons. Because of their use in radioactive tracer
work and radiotherapy, the most important Atomic radius 133.1 pm
radioisotopes are 131I, which has a half-life of Covalent radius 136 pm
8 d, and 125I, which has a half-life of 60 d. Ionic radius 220 pm
Electronegativity (Pauling scale) 2.66
Iodine was first discovered by COURTOIS in Electron affinity 301.9 kJ/mol
1811. While cleaning kelp pans with hot sulfuric Ionization potential 10.451 eV
acid, he noticed the evolution of a violet vapor Solid iodine
that condensed as crystals on the cooler parts of mp 113.6 °C
Density at 101.3 kPa
the vessel. COURTOIS provided samples of this d20 4.93 g/cm3
4
unknown material to other scientists, and in d60
4 4.866 g/cm3
1813 DAVY and GAY-LUSSAC identified it as a Refractive index, n20
D 3.34

 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

10.1002/14356007.a14_381.pub2
2 Iodine and Iodine Compounds

Vapor pressure Except for the +4 state, thermodynamically

at 25 °C 0.031 kPa
at 113.6 °C 9.17 kPa
stable compounds are formed in all these oxi-
Electrical resistivity dation states. Iodine is the least electronegative
at 25 °C 5.85 × 106 Ωcm of the halogens and is usually less violent in its
at 110 °C 8.33 × 105 Ωcm reactions than fluorine, chlorine, or bromine. It
Thermal conductivity 0.421 W m 1K 1
Dielectric constant at 25 °C 10.3
exhibits mild oxidizing properties in acid solu-
Entropy at 298.2 K 116.81 JK 1mol 1 tion. Iodine is a stronger oxidizing agent than
Heat of fusion at mp 62.17 J/g astatine, the fifth halogen. A basic chemical
Heat of sublimation at mp 238.4 J/g characteristic of the halogens is the formation
Specific heat, J g 1K 1 at 25–113.6 °C 0.21163 + 19.615 × 10 5 t
Liquid iodine
of a salt by direct reaction with a metal. Iodine
bp 184.35 °C reacts slowly with metals that form nonvolatile
Critical temperature 546 °C iodides, for example, magnesium, especially if
Critical pressure 11.6 MPa they are not finely divided.
Critical compressibility factor Zc 0.268
Density
Iodine forms compounds with all the ele-
d120 3.960 g/cm3 ments except the noble gases, sulfur, and sele-
d180 3.736 g/cm3 nium, but only reacts indirectly with carbon,
Electrical resistivity at 140 °C 1.1 × 105 Ω cm nitrogen, oxygen, and some of the noble metals.
Kinematic viscosity
at 116 °C 0.5727 mm2/s (=cSt)
Unlike chlorine, iodine does not form com-
at 184 °C 0.3785 mm2/s (=cSt) pounds with carbon monoxide, nitric oxide,
Dynamic viscosity or sulfur dioxide. Ferric and cupric salts, as
at 116 °C 2.268 mPa
s well as compounds of vanadium, chromium,
at 184 °C 1.414 mPa
s
Dielectric constant at 118 °C 11.08
and manganese in their highest oxidation states,
Heat of vaporization at bp 164.46 J/g are reduced in acid solution by iodide ion, with
Specific heat at 113.6–184 °C 0.3163 J g 1 K 1
the liberation of free iodine.
Gaseous iodine
Vapor density at 101.3 MPa, 185 °C 6.75 g/L
Entropy at 298.2 K 260.63 JK 1
mol 1 Reaction with Organic Compounds. Iodine
Specific heat 25–1200 °C 0.1464 J g 1
K 1 reacts with hydrocarbons but the equilibria
are often unfavorable because hydrogen iodide
The solubilities of iodine in water and is liberated, which may reduce the alkyl iodide
organic solvents and the color of the solutions to the hydrocarbon with formation of iodine.
are given in Table 1. Iodination can sometimes be made to go to
completion by preventing the formation of
free hydrogen iodide. The following three meth-
3. Chemical Properties ods are commonly used:

The principal oxidation states of iodine are 1, 1. Addition of an oxidizing agent, such as nitric
+1, +3, +5, and +7, but an oxide of formula IO2 acid, iodic acid, or a peroxide
with a formal oxidation state of +4 also exists. 2. Neutralization of hydrogen iodide with a
base
Table 1. Solubility of iodine in various solvents at 25 °C 3. Combination with mercuric salts to form
Solvent Solubility, g/kg Color
mercuric iodide or an iodomercurate(II)
complex [1, 2]
Benzene 164.0 red
Butan-2-ol 97 brown
Carbon disulfide 197.0 red Iodine also adds to carbon – carbon double
Carbon tetrachloride 19.2 violet bonds in compounds such as ethylene, but the
Chloroform 49.7 violet
Ethanol 271.7 brown
reactions often do not go to completion due to
Diethyl ether 337.3 brown their reversibility.
Ethyl acetate 157.0 brown Iodine is used as a catalyst in many
Hexane 13.2 violet organic reactions (e.g., acylation, halogen-
Toluene 182.5 red
Water 0.34 brown
ation, dehydration, isomerization, and pyro-
lytic decomposition).

Detection of Iodine. Iodine as the free ele-
ment can be detected by the characteristic blue
color given with a starch solution, or by the
violet color of its vapor and of solutions in
carbon tetrachloride or carbon disulfide. Iodine
is also detected by the precipitation of yellow
silver iodide, black palladium iodide, or yellow
or red mercuric iodide. Iodine can be quantita-
tively determined in acidic aqueous solutions by
titrating with a standard solution of sodium
thiosulfate by using starch as the indicator.
Iodides can also be assayed by the Volhard
method, in which an excess of a standard silver
nitrate solution is added and then backtitrated
with a standard thiocyanate solution with ferric
alum as the indicator. Quantities of up to 0.05 μg
of iodine can be determined by colorimetric
methods. Iodide and iodate in seawater and
other saline matrices can be detected by
using a reagent-free ion chromatography system
with suppressed conductivity and UV detection
[3].
4. Occurrence
According to the U.S. Geological Survey,
iodine is the forty-seventh most abundant ele-
ment in the earth’s crust if the rare earths are
counted as a single element. Small quantities of
iodine are widely distributed in rocks, soils,
underground brines, and seawater.
Minerals. Iodine is found in nature in the
following mineral forms: bruggenite,
Ca(IO3)2
H2O; dietzeite, Ca2(IO3)2
CrO4; iodo-
argyrite, AgI; iodoembolite, Ag (Cl, Br, I);
lautarite [7789-80-2], Ca(IO3)2; and marshite
[24401-69-2], CuI. The most important iodine-
containing mineral is lautarite (anhydrous
calcium iodate) [4]. Iodate occurs in the minerals
bruggenite, dietzeite, and lautarite, in caliche
deposits (between 2 and 50 feet below ground
level) in the Atacama Desert of Chile’s Antofa-
gasta and Tarapaca Provinces. The iodate is
believed to have formed from oceanic emissions
during the late Tertiary and Quaternary epochs.
The atmospheric photochemical oxidation of
iodide to iodate is thought to have occurred in
the troposphere and at ground level.
Seawater contains approximately 0.05 ppm of
iodine [5]. The amount of iodine is related to the
Iodine and Iodine Compounds 3
salinity. For example, the Red Sea contains 0.06
ppm and the Baltic Sea, 0.01 ppm. Iodine is
concentrated by marine organisms, (e.g.,
sponges and seaweed) and by fish, especially
in the thyroid gland and in liver oil, which
contain 510–69 200 ppm [5]. The brown algae
Laminaria and Fucus, which grow in temperate
zones of the Northern Hemisphere, have the
highest iodine content (0.0279–0.4535 wt %
after drying). The name kelp was originally
applied to the ash obtained by burning seaweed,
but has been extended to include the seaweed
itself, particularly the varieties yielding potash,
iodine, and other commercially important
products.
Brines. Iodine occurs frequently as potassium
or sodium iodide in subsurface brines associated
with oil and gas deposits.
In Oklahoma, iodine occurs in brines with
concentrations of 150–1200 ppm in the Morro-
wan formation of the Pennsylvanian age [6]. In
California, brines containing 30–70 ppm of
iodine are found in the Monterey Formation
of the Middle Miocene age and in the Repetto
Formation of the Pliocene age. In Michigan,
brines containing about 30 ppm of iodine occur
in the Sylvania Formation of the Devonian age.
In playa lakes in the western USA, iodine occurs
at a concentration of 14 ppm [7].
In Japan, the major iodine production
occurs in the southern Kanto gas field that
underlies the Chiba, Tokyo, and Kanagawa
Prefectures. The primary iodine reservoirs
occur in the Kiwada, Otadai, and Umegase
Formations of the Pliocene to middle Pleisto-
cene. Iodine concentrations in the southern
Kanto gas field range between 110 and 130
ppm. In the Miyazaki Prefecture, iodine and
natural gas are produced from the late Pliocene
Sadowara and Tonogori members of the Miya-
zaki group. Iodine concentrations in the Sado-
wara gas field range between 59 and 101 ppm.
Iodine is contained in the Tomigusuku Forma-
tion of the Shimajiri group of late Miocene to
early Pliocene. Iodine concentrations in the
southern Okinawa gas field range between
40 and 110 ppm. In the Niigata Prefecture,
iodine concentrations range between 7 and 68
ppm in brines in the Niigata and Hachimori gas
fields. The Niigata basin is of the Pliocene to
Pleistocene age [8].
4 Iodine and Iodine Compounds
In Indonesia, iodine occurs with trace
amounts of bromine in brines associated with
oil. The most important iodine-producing area is
the Gujangon anticline of sandstone and diato-
maceous marls of the Upper Pliocene, Kailibeng
Formation. The brines were reported to contain
about 50 ppm of iodine [9].
Information on iodine production in other
parts of the world is incomplete, but the former
Soviet Union has reported iodine concentrations
of 67 ppm in brines associated with oil fields at
Lake Bejuk-Schor, near Baku in the Azerbaidz-
han area on the Caspian Sea. Brines in the
Slavyansko – Troitsko area were reported to
have iodine concentrations of 80–120 ppm in
the Neftechinski oil field near the Black Sea. At
the Nebit-Dag iodine – bromine plant in
Turkmenistan, iodine is produced from brines
that contain 250 g/L of a combination of boron,
calcium, magnesium, sodium compounds, and
iodine [10].
5. Production
There have been three phases in the history of
iodine production:
1. Production from seaweed began in 1817 and
continued until 1959.
2. Production as a byproduct of sodium nitrate
production began in 1852.
3. Production from brines began in 1854.
Six processes have been used to produce
iodine from brines; the three that are currently
used are described here in detail. Other, obsolete
processes include the nitrate – sulfite and silver
iodide methods [10].
Production from Chile Salpeter. Chile is the
only location in the world where an iodine-
containing deposit is commercially mined and
processed. Iodine is present in the deposits as
calcium iodate (lautarite and dietzeite). Process-
ing of the deposits began prior to the 1800s. The
first iodine plant opened in 1852, but closed
during the first year of production. Iodine
production did not begin again until about
1868 and has continued ever since. Iodine is
obtained as a byproduct of sodium nitrate
production.
Crushed ore is leached to give a solution
containing sodium nitrate and calcium iodate.
After removal of sodium nitrate by precipita-
tion, the iodate-rich mother liquor is treated with
aqueous sodium hydrogensulfite to reduce the
iodate to iodide as follows [11]:
2 NaIO3 ‡ 6 NaHSO3 →2 NaI ‡ 3 Na2 SO4 ‡ 3 H2 SO4
Addition of an equivalent quantity of the
mother liquor then liberates free iodine.
5 NaI ‡ NaIO3 ‡ 3 H2 SO4 →3 Na2 SO4 ‡ 3 H2 O ‡ 3 I2
The iodine precipitate is collected by filtra-
tion and is then fed into a melting tank where it
is indirectly heated with steam to 120 °C. The
molten iodine flows to a settler tank for flaking.
The flaker consists of two water-cooled cylin-
drical drums made of Hastelloy C, an alloy
which is resistant to corrosion by iodine. The
molten iodine flows into the trough formed by
the drums and is removed by scraping. The
iodine flakes are carried by conveyor belt to
be packed in fiber drums with two plastic bags
inside. An alternative refining process is the
prilling process. The molten iodine is intro-
duced into a prilling tower through a perforated
surface so as to form a plurality of molten
streams, which transform into droplets, and
are then solidified to prills by a counter-current
flow of cold air and atomized water. Prilled
iodine is flowable and easy to handle.
Production from Brine. In the USA, iodine is
produced in Oklahoma by two brine processes.
The brines contain ca. 300 ppm of iodine. In the
blowing-out process, brine is pumped from the
production well into a surge tank. The iodide-
rich brine is fed into a column, where it is
acidified with hydrochloric acid and treated
with chlorine to oxidize the iodide to iodine.
The iodine is stripped from the brine by large
volume of air and sent to a second column,
where it is reduced and absorbed in an aqueous
solution of hydriodic acid and sulfuric acid. A
reducing environment is maintained by adding
sulfur dioxide and water. The iodide solution
is continuously fed to a storage tank where
chlorine gas precipitates crystals of molecular
iodine. The iodine is filtered from the solution,
and the acid stream is returned to the absorption
 Iodine and Iodine Compounds 5

column. The wet iodine is purified by melting compounds and the manufacturing step of
under concentrated sulfuric acid to remove iodine-containing materials such as X-ray con-
water and organic contaminants. Finally fused trast agents and optical polarizing films is very
iodine is flaked or prilled, and packaged [6]. beneficial from the viewpoint of economy, envi-
The second process is an adsorption process ronmental protection, and the conservation of
that is used with brines from oil field disposal natural resources. Many iodine manufacturers
plants. The brines are skimmed in holding tanks have recently focused on collecting and recy-
to remove suspended oil. Oil and suspended cling iodine from waste streams with a view to
matter are removed by filtration through sand. sustainability [14].
Hydrochloric acid is added to the brine and
chlorine gas to oxidize the iodide to iodine. 6. Quality Specifications,
The brine is then passed through the absorber,
where iodine is absorbed, and the waste brine is
Transportation, and Storage
neutralized and sent to a disposal well. The
Commercial crude iodine normally has a mini-
adsorbent is treated with sodium hydroxide
mum purity of 99.5 %. Impurities are chiefly
solution, which elutes the iodine as sodium
water, sulfuric acid, iron, and insoluble materi-
iodide. The iodide-rich eluate is sent to a refin-
als. The U.S. Pharmacopeia (U.S.P.) XVII spec-
ery that uses a process similar to the blowing-out
ifies an iodine content of not less than 99.8 %.
process.
The Committee on Analytical Reagents of the
In Japan, iodine is produced from under-
American Chemical Society (ACS) allows a
ground brines associated with gas fields by a
maximum of 0.005 % total bromine and chlo-
blowing-out process and by an ion-exchange
rine, and 0.010 % nonvolatile matter.
process [10]. The blowing-out process is similar
Crude iodine is packed in fiber drums with
to that used in the USA.
two plastic bags inside that contain 25–50 kg.
In the ion-exchange process, the acidified
There are no specific transportation, shipping, or
brine is treated with chlorine or sodium hypo-
safety requirements. As low temperatures
chlorite to liberate iodine, which is adsorbed on
reduce vapor pressure and therefore decrease
an ion-exchange resin (Amberlite) as polyio-
the rate of loss, a cool, well-ventilated storage
dides. The resin is transferred to a recovery
area is recommended.
plant, and the polyiodide is removed as hydro-
Under normal conditions, the rate of loss from
gen iodide by elution with sulfurous acid. Iodine
intact commercial containers is negligible.
is precipitated by addition of chlorine. The
Investment and maintenance costs are high for
iodine is then recovered from the resulting
a new iodine plant using underground brines
slurry by filtration or centrifugation, and purif-
because brine sources usually do not contain
ied by melting under sulfuric acid. Finally fused
high concentrations of iodine and because 1 kg
iodine is flaked or prilled, and packaged [12].
of chlorine is required for the production of
In China iodine resources are limited; almost
1.4–1.8 kg of iodine. Electrical costs for main-
all iodine is produced as a byproduct of seaweed
taining the pumps to bring the brine to the surface,
processing. The Wengfu Mine in China has
for air blowing the iodine, and for reinjecting the
reported iodine concentrations of 0.010% in
brine are major components of maintenance
phosphate rock. Calcining phosphate rock at
costs. Capital costs include high-quality stainless
1050 °C yielded an iodine-rich gas that could
steels because iodine is highly corrosive. In
be further processed. The iodine recovery plant
addition, the brine must be leased from private
consisted of a blowing column and an absorbing
landowners over large acreages for many years.
column with an annual output of 100 t of crude
iodine was commercialized in 1998 [13].
7. Uses
Recycling of Iodine. The production of iodine
is limited mainly to Japan and Chile, so that Iodine was first exploited commercially in 1916
iodine is an extremely limited precious resource. in the form of potassium iodide as a remedy for
Accordingly, recovery of expensive iodine from goiter. In 1916, tincture of iodine and iodoform,
used iodine-containing materials or iodine CHI3, were used as disinfectants for cuts and
6 Iodine and Iodine Compounds
abrasions, and for sanitation. In 1939, LOUIS
DAGUERRE published details of his method for
making photographs on plated silver by using
iodine vapor to form a thin coating of light-
sensitive silver iodide crystals. Clinical uses of
iodine have evolved from simple tinctures to
radiopaque media, iodophors, and batteries in
subcutaneously implanted pacemakers [15].
Iodine is also used in a wide variety of specialty
chemicals.
Uses include dietary supplements, catalysts,
inks and colorants, pharmaceuticals, radiopaque
diagnostic (X-ray contrast) media, photographic
equipment, sanitary and industrial disinfectants,
and stabilizers, as well as the production of
motor fuels, smog inhibitors, lubricants, high-
purity metals, and iodized salt. Iodine also has
applications in cloud seeding.
Catalysts. The major end use of iodine is in
catalysts. Most acetic acid is produced by meth-
anol carbonylation processes. The process
involves hydrogen iodide and iodomethane as
the intermediates. Two processes are known for
the carbonylation of methanol: the rhodium-
catalyzed Monsanto process, and the iridium-
catalyzed Cativa process. The latter process is
greener and more efficient [16]. Iodide catalysts,
such as titanium tetraiodide [7720-83-4] and
aluminum iodide [7784-23-8], are also signifi-
cant in the dehydrogenation of butane and
butene to butadiene [17], and in the preparation
of stereoregular polymers [18]. Samarium diio-
dide (SmI2) [32248-43-4] is an important
reagent in organic synthesis. SmI2 promotes a
number of important carbon–carbon bond for-
mation reactions and is utilized for stereoselec-
tive synthesis of natural products [19].
Optical Polarizing Film. Optical polarizing
films are indispensable materials for liquid crys-
tal displays (LCDs) such as LCD TV, mobile
phones, and automotive navigation systems. In
the widely-used iodine-type poly(vinyl alcohol)
(PVA) polarizing films, iodine-dyed PVA films,
which are drawn and cross-linked in a hot boric
acid solution to improve their durability by cre-
ating a cross-linked internal structure, are used as
polarizers [20].
Stabilizers. Consumption of iodine as a stabi-
lizer in the manufacture of nylon for tire cord
and carpets, and for converting rosins, tall oil,
and other wood products to more stable forms is
the second major end use [21].
Butadiene reacts with iodine and copper
cyanide to yield a copper(I) iodide complex
of dehydroadiponitrile. Reaction with hydro-
cyanic acid gives a high yield of adiponitrile,
which can be catalytically hydrogenated to give
hexamethylenediamine, a precursor of nylon 66
[22]. In the reaction with HCN the starting
materials, copper(I) cyanide and iodine, are
regenerated.
Animal Feeds. The third area of major iodine
consumption is in the form of additives for
animal feeds. In 1986, the recommended
amount of ethylenediamine dihydroiodide
[5700-49-2] (EDDI) consumed in animal feeds
was lowered from 50 to 10 mg per head per day,
in accordance with the U.S. FDA Compliance
Policy Guideline (7125.18). Cattle and sheep
are fed iodine compounds for the prevention of
soft tissue lumpy jaw. The use of iodized salt
has significantly reduced the incident of goiter
in livestock in certain iodine-deficient geo-
graphical regions. In addition, iodized protein
in fowl and cattle feed increases yields of eggs
and milk. About 25 % of the reported domestic
consumption of iodine was in animal feeds,
primarily as the compound EDDI, but also as
potassium iodide, calcium iodate [7789-80-2],
and calcium periodate [7790-28-5]. Iodine is
one of 14 mineral commodities listed by the
National Feed Ingredients Association as being
used for domestic meat production.
Agrochemicals. Today a number of halogen-
modified compounds are among the best-selling
agrochemicals. However iodine-containing com-
pounds are in the minority. Typical iodine-con-
taining compounds, in use for a long time to date
are as follows;
Ioxynil [1689-83-4] (herbicide), Ioxynil octa-
noate [3861-47-0] (herbicide), triiodobenzoic
acid [88-82-4] (plant growth regulator), Iodobo-
nil [25671-45-8] (herbicide), Benodanil [15310-
01-7] (fungicide), and Iodocarb [55406-53-6]
(fungicide).
Modern iodine-containing agrochemicals are
as follows;
Iodsulfuron-methyl-sodium [144550-36-7]
(herbicide), Proquinazid [189278-12-4]

(fungcide), and Flubendiamide [272451-65-7]
(insecticide) [23]
Disinfectant. Iodine is an effective germicide
for a wide range of microorganisms. The use of
iodine in sanitary preparations, such as disin-
fectants, is the fourth major area of consump-
tion. Iodine is often used in conjunction with
iodine-complexing nonionic surfactants or
polymers (iodophors) in disinfectants that are
used in dairies, laboratories, and food process-
ing plants, and for the sanitation of dishes in
restaurants [22]. Poly(vinyl pyrrolidinone) –
iodine complex [25655-41-8], PVP-iodine, is
extensively used because of its germicidal, bac-
tericidal, fungicidal, and general disinfecting
properties [24] (→ Disinfectants). The solution
contains about 10 % available iodine and about
5 % inactive iodide [25]. Globaline tablets are
used by the army to disinfect water supplies
without boiling [26]. Iodine is used as a disin-
fectant in swimming pools and is an efficient
microbiocide. It is more effective than chlorine
against the standard fecal indicators. High
iodine concentrations are easily maintained
and are more stable than chlorine [27]. A study
in Florida showed that concentrations up to 5
ppm of iodine in potable water are not deleteri-
ous to health and that 1 ppm is sufficient to
safely disinfect a water supply with no loss of
effectiveness at high pH values [28]. Triosyn is
a stable iodinated ion-exchange resin consisting
of a triiodide complex (I3–) that is bound ioni-
cally to a quaternary amine based ion-exchange
polymer. This polymer is a versatile antimicro-
bial agent that belongs to a novel class of
nontoxic, broad-spectrum biocidal agents used
to control disease-causing microorganisms and
to treat microbial infections. Triosyn provides
active biological protection and chemical neu-
tralization of agents [29].
Pharmaceuticals. The fifth major area of
iodine consumption is in pharmaceuticals, pri-
marily as radiopaque (X-ray contrast) media,
which are injected intravenously or intra-
cerebrally to produce X-ray photographs of
the internal structure of the body (→ X-Ray
Contrast MedIA2). Clinical use includes cardi-
oangiography, cerebral angiography, arteriogra-
phy, urography, and phlebography. Media listed
by the U.S. International Trade Commission
Iodine and Iodine Compounds 7
include meglumine diatrizoate [131-49-7],
sodium diatrizoate [737-31-5], iopanoic acid
[96-83-3], iothalamic acid [2276-90-6], and
sodium tyropanoate [7246-21-1]. These sub-
stances contain between 47 and 67 wt % iodine.
Of the nonionic contrast media, Iohexol (1985),
N,N'-bis(2,3-dihydroxypropyl-5-[N-(2,3-dihy-
droxypropyl)acetamidol]-2,4,6-triiodoisophtha-
lamide, which contains 46 wt % iodine, and
Iopamidol (1985), 1-N,3-N-bis(1,3-dihydroxy-
propan-2-yl)-5-[(2S)-2-hydroxypropanamido]-
2,4,6-triiodobenzene-1,3-dicarboxamide were
the first to be marketed [30]. Thereafter,
many nonionic contrast media, such as Ioversol
(1988) 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[2-
hydroxy-N-(2-hydroxyethyl)acetamido]-2,4,6-
triiodobenzene-1,3-dicarboxamide, Ioxilan
(1995), N-(2,3-dihydroxypropyl)-N´ -(2-hydrox-
yethyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-
2,4,6-triiodoisophthalamide, Iopromide (1995),
1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-
triiodo-5-(2-methoxyacetamido)-1-N-methyl-
benzene-1,3-dicarboxamide, were developed
[31]. Potassium iodide is widely used as an
expectorant in cough medicines. Hydriodic
acid and potassium iodide are used in the syn-
thesis of amphetamine, methamphetamine, and
ethylamphetamine.
Miscellaneous Uses. One of the oldest indus-
trial uses of iodine is in photography. Up to 7 %
of the silver salt in negative emulsions is iodide.
However the digital photographic industry has
accomplished unprecedented growth in the past
decades. As a result, traditional silver halide-
based photography is being rapidly displaced by
digital photography [32]. Iodine is also a con-
stituent of some dyes including 4´ ,5´ -diiodo-
fluorescein [38577-97-8], rose bengal [11121-
48-5], and erythrosine [16423-68-0].
Erythrosine, certified food color Red No. 3,
contains 58 % iodine and is used in carbonated
soft drinks, powdered drinks, gelatin desserts,
icings, and pet food. 4´ ,5´ -Diiodofluorescein
[38577-97-8], C.I. Solvent Red 73, is used
in dyeing and printing cotton, in printing
half-silk, and in dyeing jute and straw prod-
ucts. Sodium iodate can also be used in the
dyeing process as an oxidizing agent. Fluo-
roiodocarbons, such as CF3(CF2)7I [507-63-1]
and CF3(CF2)7CH2CH2I [2043-53-0], are
intermediates in the manufacture of oil and
8 Iodine and Iodine Compounds

water repellents, surfactants, and fire- Table 2. Worldwide production of crude iodine [39]
extinguishing foams [33, 34]. Country Production, t/a
Trifluoroiodomethane [2314-97-8], CF3I),
Mr 195.91 is a nontoxic, nonflammable, low 2010 2011 2013 2014
USA W∗ W W W
global warming potential (GWP<5) compound Chile 17 500 18 000 20 700 21 000
with almost zero ozone depletion potential. CF3I China NA∗∗ NA NA NA
is also useful as a foam blowing agent and a Indonesia 75 75 75 75
plasma etching agent. CF3I can be produced Japan 9300 9400 9500 9500
Former Soviet Union 300 170 200 200
from CHF3 and I2 by a novel catalyst system Turkmenistan 480 480 500 500
that allows practical and cost-effective large- Azerbaijan 350 350 350 350
scale manufacture [35]. Total 28 000 28 500 31 300 31 600
The addition of iodine to aromatic hydro- ∗
W = Withheld to avoid disclosing company proprietary data.
carbons, such as n-butylbenzene [104-51-8], ∗∗
NA = not available.
results in the formation of charge-transfer com-
plexes that are effective lubricants for some
metals, e.g., titanium or steels [36]. Iodine is crystal, according to Industrial Minerals, aver-
also used to produce high-purity forms of tita- aged around $50 per kilogram at the beginning
nium, silicon, hafnium, and zirconium in the van of 2014 and decreased continuously to an aver-
Arkel process, which involves the formation of age of around $37 per kilogram in September
volatile iodides [37]. 2014 [38].
Table 2 summarizes world production of
crude iodine; estimated iodine consumption
8. Economic Aspects according to use is given in Table 3.
Strong demand for iodine has continued,
In Japan, iodine is produced entirely as a driven by the LCD and X-ray contrast medium
byproduct of natural gas production. Therefore, industries. Some companies that minimized
Japan’s iodine production has remained at con- their use of iodine and iodine compounds in
stant levels because the amount of water 2011 and 2012 owing to the uncertainty of
extracted for this purpose has to be maintained supply have come back into the market. With
at constant levels to prevent land subsidence continued global economic recovery, demand
associated with pumping of water from for iodine for use in biocides, iodine salts,
unconsolidated formations. Japan accounted LCDs, synthetic fabric treatments, and X-ray
about 30% of iodine production in the world contrast media was expected to increase at a rate
in 2014. of between 3.% and 4% per annum during the
Chile has large reserves of iodine associated next decade [38].
with sodium nitrate deposits, but until 1986 had
not provided capital for expansion or process
improvements. In 1987, Chile completed con-
Table 3. Estimated world consumption of iodine according to use
struction of a 150 t/a iodine plant to extract
iodine from waste tailings from sodium nitrate Use Consumption, %
production. After that many iodine plants were SQM (2014)a Kanto (2014)b
constructed in Chile. These new plants guaran-
teed Chile a secure source of iodine from the X-ray contrast media 22 22
Biocide 18 12
accumulated waste tailings. Pharmaceuticals 13 10
Today Chile has the largest iodine produc- Optical polarizing films 12 11
tion capacity in the world. In recent years, Chile Animal nutrition 8 7
is the world’s leading producer of iodine, fol- Heat stabilizers 4 5
Fluorine derivatives 7
lowed by Japan and the USA. Chile accounted Human nutrition 3 4
for more than 60% of world production in 2014. Industrial catalysts 11
The iodine price reached historically high Others 13 18
levels in 2012, after which iodine prices steadily a
Annual Report SQM, 2014.
declined throughout 2014. Spot prices of iodine b
Kanto Natural Gas Dev. WEB [40].

9. Inorganic Iodine Compounds
Iodine forms binary compounds with hydrogen,
metals, other halogen elements, and oxygen.
Iodides range from completely ionic to
covalent structures; for example, potassium
iodide is ionic and titanium tetraiodide is
covalent. In general, the ionic iodides are the
most soluble of the halides of a given element.
Commercially, iodides are the most impor-
tant class of iodine compounds. In general, they
are less fusible and volatile than chlorides or
bromides. At higher temperature, even the more
stable iodides show dissociation. Volatile
covalent iodides, such as those of aluminum
and titanium, form inflammable mixtures with
air. Dry nitrogen triiodide, NI3, formed by
reacting iodine with excess ammonia, will
explode at ordinary temperature under the
slightest shock.
Potassium iodide [7681-11-0], KI, Mr 166.02,
mp 686 °C, forms colorless cubic crystals,
which are soluble in water, ethanol, methanol,
and acetone. It is used in animal feeds, catalysts,
photographic chemicals, and for sanitation.
Potassium iodide is produced by reaction of
potassium hydroxide with iodine. The product
is purified by crystallization from water.
Sodium iodide [7681-82-5], NaI, Mr 149.92,
mp 662 °C, forms colorless cubic crystals which
are soluble in water, ethanol, acetone and glyc-
erol. It is used in photography, for the produc-
tion of organic chemicals, and as an expectorant
in cough medicines. Sodium iodide is produced
by the addition of sodium hydroxide or sodium
carbonate to an acidic iodide solution. The
anhydrous product is obtained from the solution
by evaporation.
Ammonium iodide [12027-06-4], Mr 144.96,
forms white tetragonal crystals which are solu-
ble in water, alcohol, glycerol, and methanol.
On heating, ammonium iodide sublimes with
decomposition. It is used as an expectorant and
in photographic chemicals. Ammonium iodide
is prepared from ammonia, iodine, and hydro-
gen peroxide; from ammonia and hydrogen
iodide; or from ammonium carbonate and
hydrogen iodide. To prevent the crystals or
solution from turning yellow due to formation
Iodine and Iodine Compounds 9
of free iodine, up to 1 % of ammonium hypo-
phosphite is added as a stabilizer.
Iodates have the general formula MIO3, where
M is a univalent metal or electropositive radical.
Iodates can be prepared by dissolving iodine in a
caustic alkali solution and recovering the iodate
by filtration. Iodine can be oxidized with con-
centrated nitric acid to iodic acid, followed by
neutralization with an oxide or hydroxide; oxi-
dation of an alkaline iodide solution with chlo-
rine; or electrolytic oxidation of a neutral iodide
solution containing chromate with a platinum
anode and an iron cathode in a nondiaphragm
cell. Iodates are precipitated when solutions of
metal salts react with alkali metal iodates.
Most iodates are white. The solid metal
iodates are stable and safe to handle in the
pure state, but should be kept out of contact
with organic substances and other combustible
materials because such mixtures can be explo-
sive. The salts of the alkali metals and magne-
sium are soluble in water.
Iodates and periodates can be determined by
addition of excess alkali metal iodide in an acid
solution followed by titration of the liberated
iodine with thiosulfate. Periodates can be deter-
mined in the presence of iodates by adding
potassium iodide to a solution buffered with
borax and boric acid, and titrating the liberated
iodine with sodium arsenite solution.
Hydrogen iodide [10034-85-2], HI, Mr 127.93,
mp 50.9 °C, bp 35.4 °C, is a colorless gas
which fumes in moist air. It is the least stable of
the common hydrogen halides, and the best
reducing agent. It cannot be prepared using
strong acids because it is readily oxidized; there-
fore, it must be prepared from a weak acid and
iodine, or by the hydrolysis of certain iodides.
Hydriodic acid is the colorless solution formed
when hydrogen iodide gas dissolves in water
and, at commercial strength, typically contains
47 % hydrogen iodide. Hydriodic acid is used in
the preparation of iodides and is an important
reagent in organic chemistry. Dilute hydriodic
acid reacts with metals or their hydroxides,
carbonates, and other salts to yield metal
iodides.
Iodic acid [7782-68-5], HIO3, Mr 175.93,
forms colorless rhombohedral crystals, which
10 Iodine and Iodine Compounds
decompose at 110 °C. It is prepared by oxidizing
iodine with nitric acid. It is a strong oxidizing
agent that oxidizes iodide to iodine, sulfite to
sulfate, and hydrogen sulfide to sulfur. It reacts
vigorously with dry carbon, phosphorus, and
organic matter.
Polyiodides and polyhalides form when
iodine or iodine halides combine with halide
salts. Some examples are RbI3 [12298-69-0],
[N(CH3)4I9 [3345-37-7], [N(C2H5)4IBr2]
[20445-98-1], and KICl4 [14323-44-5]. Polyio-
dide and polyhalide salts usually form highly
colored orthorhombic crystals; however, KIF6
[20916-97-6] is white.
Iodine Halides. Seven iodine halides are
known: IF, IF3, IF5 [7783-66-6], IF7 [16921-
96-3], I2Cl6 [865-44-1], ICl [7790-99-0], and
IBr [7789-33-5]. All are readily formed by
direct reaction of the two halogen elements.
10. Organic Iodine Compounds
As with inorganic iodides, organic iodides have
higher specific gravities and refractive indices
than the corresponding chloro and bromo deriv-
atives, and higher melting and boiling points.
Compounds containing an iodine atom attached
to a primary carbon atom are the most stable.
Secondary compounds are less stable, and ter-
tiary are the least stable of all. Aliphatic iodo
compounds can be prepared by treating alcohols
with a mixture of iodine and red phosphorus.
Other methods for preparing aliphatic iodo com-
pounds include the addition of iodine halides or
iodine to olefins; the substitution reactions
between an alkyl bromide or chloride and an
alkali metal iodide; and the reaction of alcohols
with triphenyl phosphite and methyl iodide.
Organic iodo compounds are highly reactive.
The alkyl iodides are generally 50–100 times
more reactive than the corresponding chlorides.
Reactivity of unsaturated organic iodides is
affected little if iodine is attached to one of
the carbon atoms involved in the double
bond, but reactivity is promoted if iodine is
attached to the carbon atom in the α position
to the double bond. Iodine in organic com-
pounds can be determined after being converted
into an inorganic form by heating the compound
with one of the following: (1) fuming nitric acid
in a sealed strong glass tube, the Carius method;
(2) sodium peroxide in a combustion container;
or (3) a mixture of chromic and sulfuric acids,
followed by addition of phosphoric acid and
distillation into a solution of sodium arsenite
[41].
Iodoform [75-47-8], triiodomethane, CHI3, mp
119 °C, crystallizes from acetone as yellow
hexagonal plates, which have a characteristic
penetrating odor and are insoluble in water. The
compound can be prepared by the reaction of
iodine chloride with acetone in the presence of
potassium hydroxide, or by reaction of chloro-
form with methyl iodide. Iodoform is used as a
disinfectant.
Methylene iodide [75-11-6], CH2I2, Mr 267.85,
mp 5 °C, bp 180 °C (101.3 kPa), is a colorless
liquid when pure. It has a relative density of
3.325 at 20 °C and can be mixed with benzene
20 ˆ 0:879† to produce liquids with different
d20
densities. These mixtures are used in the deter-
mination of the refractive indices of minerals
and for the separation of minerals according to
density.
Ethyl iodide [75-03-6], C2H5I, Mr 155.98, bp
72.3 °C, is a colorless liquid, which is com-
pletely miscible with ethanol and ether, but only
partially miscible with benzene. Ethyl iodide is
prepared by reaction of ethanol with iodine and
red phosphorus.
Methyl iodide [74-88-4], CH3I, Mr 141.95 mp
66.1 °C, bp 42.5 °C, is a colorless, transparent
liquid, which turns brown upon exposure to
light. Methyl iodide is prepared from methyl
alcohol, iodine, and red phosphorus. Methyl
iodide is used as a methylating agent.
Iodobenzene [591-50-4], Mr 204.02, mp
30 °C, bp 188.7 °C, is a colorless liquid that
rapidly turns yellow and has a characteristic
odor. Iodobenzene is prepared by diazotization
of aniline followed by treatment of the solution
with an aqueous solution of potassium iodide, or
by the action of nitric acid on a benzene and
iodine mixture.
4,4´ -Diiodobiphenyl [3001-15-8], C12H8I2, Mr
406.00, mp 201–204 °C, is colorless crystalline
powder, which turns yellow upon exposure to

light. 4,4´ -Diiodobiphenyl is prepared from
biphenyl and iodine. It is used as liquid crystal
and intermediate for high-performance polymers.
5-Amino-2,4,6-triiodoisophthalic acid [35453-
19-1], C8H4I3NO4, Mr 558.84, mp 265–270 °C,
is beige solid, which is used as an intermediate
for nonionic iodinated X-ray contrast agents.
Hypervalent Iodine Compounds. Phenylio-
dine(III) diacetate [3240-34-4] (PIDA), C6H5I
(O2CCH3)2, Mr 322.10, mp 161–163 °C, is a
white to off-white solid.
Phenyliodine(III) bis(trifluoroacetate) [2712-
78-9] (PIFA) (CF3CO2)2IC6H5, Mr 430.04,
121–125 °C, is white crystalline solid.
1,1,1-Triacetoxy-1,1-dihydro-1,2-benzio-
doxol-3(1H)-one [87413-09-0] (DMP)
C13H13IO8, Mr 424.14, mp 130–133 °C, is a
white powder.
Hypervalent iodine reagents are receiving
considerable attention as oxidants due to their
low toxicity, mild reactivity, ready availability,
high stability, easy handling, and so on. A major
use of hypervalent reagents is replacing the
highly toxic heavy metal oxidizing agents,
that is, lead(IV), mercury(II), and thallium(III)
reagents. As stoichiometric oxidants, they medi-
ate a wide array of bond-forming reactions and
other oxidative transformations. For example,
PIDA- and PIFA-induced oxidations of phenols
and related reactions have been applied to total
syntheses of biologically important natural
products and their pivotal intermediates. The
pentavalent iodine compound Dess–Martin
periodinane (DMP), is widely known as mild
and highly selective reagent for the oxidation of
alcohols. For details of the synthetic versatility
of these reagents, see [42].
Iodinating Agents. N-Iodosuccinimide [516-
12-1] (NIS)
C4H4INO2 Mr 224.98, mp 202–206 °C, is
white or off-white solid.
1,3-Diiodo-5,5-dimethylhydantoin [2232-
12-4] (DIH)
C5H6I2N2O2 Mr 379.92, mp 198 °C
(decomp.), is light yellow or white solid.
2-Iodo-1,2-benzisothiazol-3(2H)-one 1,1-
dioxide [86340-94-5]
C7H4INO3S Mr 309.08, mp 206–208°C,
forms pale yellow crystals.
Iodine and Iodine Compounds 11
NIS is an electrophilic iodinating reagent and
is used to iodinate various substances in a
similar manner to molecular iodine. A number
of iodination reactions using NIS have been
reported, and alkenes, heteroaromatic rings,
and the α position of ketones are successfully
iodinated. DIH is a powerful electrophilic iodin-
ating reagent and readily iodinates various
aromatic compounds under mild reaction con-
ditions. DIH is a pale yellow solid that does not
sublime like molecular iodine. NIS is a mild
electrophilic iodinating reagent that is chemi-
cally stable and soluble in common polar
organic solvents. NIS can convert various
alkenes and activated aromatic rings to corre-
sponding iodinated compounds. In addition,
NIS is an efficient reagent to synthesize benzyl
and allyl iodides from the corresponding alco-
hols [43].
11. Toxicology and Occupational
Health
Iodine is absorbed by the body and concentrated
in the form of diiodotyrosine and tri-
iodothyronine, which form thyroxine that is
stored as thyroglobulin. Thyroxine is secreted
by the thyroid, enters the circulation, and is
carried to the peripheral tissues, where it con-
trols tissue metabolism primarily through regu-
lation of enzyme activities (→ Hormones, 1.
Hormone Systems). Iodine is essential to higher
animals and humans. A normal person requires
about 75 mg of iodine per year, which is usually
consumed as iodized salt that contains one part
sodium or potassium iodide to 100 000 parts of
sodium chloride. Iodine deficiency is a major
cause of goiter. Studies on chickens link auto-
immune thyroiditis directly with consumption
of large amounts of iodine [44]. These results
are also applicable to humans.
Iodine is safer to handle at ambient tempera-
ture than chlorine or bromine because it is a
solid with a lower vapor pressure. When han-
dling properly packaged containers, usual work
clothes are sufficient. In the handling of solid,
unpacked iodine, rubber gloves, a rubber apron,
and safety goggles are recommended; more
drastic situations may necessitate the use of a
gas mask. The maximum safe concentration for
short-term exposure of up to 1 h is 1.0 ppm.
12 Iodine and Iodine Compounds
Exposure of the lungs and eyes can be irritating
at concentrations of 0.1 ppm and should be
avoided. Exposure in concentrations higher
than 0.1 ppm for extended periods causes severe
irritation to the eyes and the respiratory tract,
and may lead to pulmonary edema [45]. The
mean lethal oral dose for an adult is 2–4 g.
Prolonged contact with the skin may be harmful.
Treatment includes irrigating the eyes with
water or washing the contaminated body area
with a 5 % solution of sodium thiosulfate, fol-
lowed by saline catharsis. Iodine and concen-
trated solutions, including U.S.P. tincture, are
classed as poisons because of their irritating
effects to the gastrointestinal tract. The gastric
treatment antidote is a 5 % solution of sodium
thiosulfate followed by saline catharsis. Medical
attention should be provided.
In the USA, the OSHA has set the maximum
concentration of iodine vapor permitted in the
working atmosphere as 0.1 ppm [46].
The ACGIH established 0.1 ppm as the TLV
(TWA) for iodine. The MAK value is also 0.1
ppm. To detect iodine at this concentration, air
monitoring is necessary [47].
Iodine and iodine-containing compounds are
not genotoxic in most short-term tests, and this
is indirect evidence for the absence of carcino-
genic activity of these compounds with high
probability [48].
Empty containers may be destroyed in an
incinerator or decontaminated by washing with
a dilute sodium thiosulfate solution. Bulk waste
should be treated by controlled chemical opera-
tions to reclaim the iodine or convert it to
harmless waste.
Iodine can be mixed safely with ammonia
solutions in the presence of a reactive organic
substance; however, contact of gaseous ammo-
nia or its solutions with free iodine and its
halogen derivatives in any form can form explo-
sive nitrogen triiodide [13444-85-4], NI3. If this
dark brown to black solid forms, it should be
discarded while wet or destroyed by adding a
reducing agent, such as ethanol, or more of the
compound to be iodinated.
In general, iodides are acutely toxic only
when ingested in large amounts. Chronic inges-
tion or absorption through the skin may produce
iodism, which is manifested by a rash, nasal
drip, or headache. In severe cases, weakness,
anemia, and general depression may occur. Care
should be taken in handling organic iodine
compounds.
In 1979 (Three Mile Island, USA), 1986
(Chernobyl, Ukraine), and 2011 (Fukushima,
Japan) nuclear accidents caused the release of
radioactive iodine, 131I, into the atmosphere.
Ingestion of potassium iodide, KI, can reduce
the radiation dose to the thyroid gland by up to
90 % if administered before or shortly after
exposure. A dosage of 130 mg was recom-
mended for adults. If administered 4 h after
exposure, KI can block 50 % of the uptake of
131
I. The U.S. Federal Emergency Management
Agency provided guidelines to state and local
agencies regarding the distribution of KI for use
as a thyroidal blocking agent by the general
public in the vicinity of nuclear power plants
[49]. Guidance on the use of radioprotective
substances was delegated to the FDA, which
recommended that KI be used by people who
are likely to receive more than 10–20 rad to the
thyroid [50].
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Further Reading
Lauterbach, A. and Ober, G. (2005) Iodine and iodine compounds, in
Kirk Othmer Encyclopedia of Chemical Technology, 5th edn,
vol. 14, John Wiley & Sons, Hoboken, NJ, pp. 353–380. online:
doi: 10.1002/0471238961.0915040912012120.a01.pub2.
Preedy, V.R, Burrow, G.N, and Watson, R.R (eds) (2009) Compre-
hensive Handbook of Iodine, Elsevier, Amsterdam, London.
Kaiho, T. (ed.) (2014) Iodine Chemistry and Applications, John
Wiley & Sons, Hoboken, NJ.