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Carbon monoxide

From Wikipedia, the free encyclopedia

Carbon monoxide (CO) is a colorless, odorless, and


tasteless gas that is slightly less dense than air. It is toxic to Carbon monoxide
hemoglobic animals (both invertebrate and vertebrate,
including humans) when encountered in concentrations
above about 35 ppm, although it is also produced in normal
animal metabolism in low quantities, and is thought to have
some normal biological functions. In the atmosphere, it is
spatially variable and short lived, having a role in the
formation of ground-level ozone.

Carbon monoxide consists of one carbon atom and one


oxygen atom, connected by a triple bond that consists of two
covalent bonds as well as one dative covalent bond.[5] It is Names
the simplest oxocarbon and is isoelectronic with the cyanide Preferred IUPAC name
anion, the nitrosonium cation and molecular nitrogen. In Carbon monoxide
coordination complexes the carbon monoxide ligand is called
Other names
carbonyl.
Carbon monooxide
Carbonous oxide
Carbon(II) oxide
Contents Carbonyl
Flue gas
1 History
2 Sources Monoxide
3 Molecular properties Identifiers
3.1 Bonding and dipole moment
CAS Number 630-08-0
3.2 Bond polarity and oxidation state
4 Biological and physiological properties 3D model (JSmol) Interactive image
4.1 Toxicity Beilstein Reference 3587264
4.2 Normal human physiology
4.3 Microbiology ChEBI CHEBI:17245
5 Occurrence ChemSpider 275
5.1 Atmospheric presence
5.2 Urban pollution ECHA InfoCard 100.010.118
5.2.1 Role in ground-level ozone EC Number 211-128-3
formation
Gmelin Reference 421
5.3 Indoor pollution
5.4 Presence in blood KEGG D09706
5.5 Astrophysics
MeSH Carbon+monoxide
6 Production
6.1 Industrial production PubChem CID 281
6.2 Laboratory preparation RTECS number FG3500000
7 Coordination chemistry
8 Organic and main group chemistry UNII 7U1EE4V452
9 Uses UN number 1016
9.1 Chemical industry
9.2 Meat coloring InChI
9.3 Medicine InChI=1S/CO/c1-2
9.4 Metallurgy Key: UGFAIRIUMAVXCW-UHFFFAOYSA-N

9.5 Lasers InChI=1/CO/c1-2


Key: UGFAIRIUMAVXCW-UHFFFAOYAT
9.6 Niche uses
10 See also SMILES
11 References [C-]#[O+]
12 External links Properties
Chemical formula CO
Molar mass 28.010 g/mol
History
Appearance colorless gas

Aristotle (384322 BC) first recorded that burning coals Odor odorless
produced toxic fumes. An ancient method of execution was Density 789 kg/m3, liquid
to shut the criminal in a bathing room with smoldering coals. 1.250 kg/m3 at 0 C, 1 atm
What was not known was the mechanism of death. Greek 1.145 kg/m3 at 25 C, 1 atm
physician Galen (129199 AD) speculated that there was a
change in the composition of the air that caused harm when Melting point 205.02 C (337.04 F;
inhaled.[6] In 1776, the French chemist de Lassone produced 68.13 K)
CO by heating zinc oxide with coke, but mistakenly Boiling point 191.5 C (312.7 F; 81.6 K)
concluded that the gaseous product was hydrogen, as it
Solubility in water 27.6 mg/L (25 C)
burned with a blue flame. The gas was identified as a
compound containing carbon and oxygen by the Scottish Solubility soluble in chloroform, acetic
chemist William Cumberland Cruikshank in 1800.[7][8] Its acid, ethyl acetate, ethanol,
toxic properties on dogs were thoroughly investigated by ammonium hydroxide,
Claude Bernard around 1846.[9] benzene

During World War II, a gas mixture including carbon Henry's law 1.04 atm-m3/mol
constant (kH)
monoxide was used to keep motor vehicles running in parts
of the world where gasoline and diesel fuel were scarce. Magnetic -9.8106 cm3/mol
External (with a few exceptions) charcoal or wood gas susceptibility ()
generators were fitted, and the mixture of atmospheric Refractive index 1.0003364
nitrogen, carbon monoxide, and small amounts of other gases (nD)
produced by gasification was piped to a gas mixer. The gas Dipole moment 0.122 D
mixture produced by this process is known as wood gas.
Thermochemistry
Carbon monoxide was also used on a large scale during the
Holocaust at some Nazi German extermination camps, the Specific 29.1 J/K mol
most notable by gas vans in Chemno, and in the Action T4 heat capacity (C)
"euthanasia" program.[10] Std molar 197.7 Jmol1K1
entropy (So298)

Sources Std enthalpy of


o
110.5 kJmol1
formation (fH 298)
Carbon monoxide is produced from the partial oxidation of Std enthalpy of 283.4 kJ/mol
carbon-containing compounds; it forms when there is not combustion
enough oxygen to produce carbon dioxide (CO2), such as (cHo298)
when operating a stove or an internal combustion engine in Hazards
an enclosed space. In the presence of oxygen, including Safety data sheet See: data page
atmospheric concentrations, carbon monoxide burns with a
ICSC 0023
blue flame, producing carbon dioxide.[11] Coal gas, which
was widely used before the 1960s for domestic lighting, EU classification
F T+
(DSD) (outdated)
cooking, and heating, had carbon monoxide as a significant
fuel constituent. Some processes in modern technology, such R-phrases (outdated) R61 R12 R26 R48/23
as iron smelting, still produce carbon monoxide as a
S-phrases (outdated) S53 S45
byproduct.[12]
NFPA 704 [2]

Worldwide, the largest source of carbon monoxide is natural 4


in origin, due to photochemical reactions in the troposphere 3 0
that generate about 5 1012 kilograms per year.[13] Other
natural sources of CO include volcanoes, forest fires, and
Flash point 191 C (311.8 F; 82.1 K)
other forms of combustion.
Autoignition
In biology, carbon monoxide is naturally produced by the Autoignition 609 C (1,128 F; 882 K)
action of heme oxygenase 1 and 2 on the heme from temperature
hemoglobin breakdown. This process produces a certain Explosive limits 12.574.2%
amount of carboxyhemoglobin in normal persons, even if Lethal dose or concentration (LD, LC):
they do not breathe any carbon monoxide. Following the first
report that carbon monoxide is a normal neurotransmitter in LC50 (median 8636 ppm (rat, 15 min)
concentration)
1993,[14][15] as well as one of three gases that naturally 5207 ppm (rat, 30 min)
modulate inflammatory responses in the body (the other two 1784 ppm (rat, 4 hr)
being nitric oxide and hydrogen sulfide), carbon monoxide 2414 ppm (mouse, 4 hr)
has received a great deal of clinical attention as a biological 5647 ppm (guinea pig, 4 hr)[1]
regulator. In many tissues, all three gases are known to act as
LCLo (lowest 4000 ppm (human, 30 min)
anti-inflammatories, vasodilators, and promoters of published) 5000 ppm (human, 5 min)[1]
neovascular growth.[16] Clinical trials of small amounts of
carbon monoxide as a drug are ongoing.[17] Too much US health exposure limits (NIOSH):[3]
carbon monoxide causes carbon monoxide poisoning. PEL (Permissible) TWA 50 ppm (55 mg/m3)
REL TWA 35 ppm (40 mg/m3) C
Molecular properties (Recommended) 200 ppm (229 mg/m3)
IDLH (Immediate 1200 ppm
Carbon monoxide has a molar mass of 28.0, which, danger)
according to the ideal gas law, makes it slightly less dense
than air, whose average molar mass is 28.8. Related compounds
Related carbon Carbon dioxide
The bond length between the carbon atom and the oxygen oxides Carbon suboxide
atom is 112.8 pm.[18][19] This bond length is consistent with Oxocarbons
a triple bond, as in molecular nitrogen (N2), which has a
Supplementary data page
similar bond length (109.76 pm) and nearly the same
molecular mass. Carbonoxygen double bonds are Structure and Refractive index (n),
significantly longer, 120.8 pm in formaldehyde, for properties Dielectric constant (r), etc.
example.[20] The boiling point (82 K) and melting point Thermodynamic Phase behaviour
(68 K) are very similar to those of N2 (77 K and 63 K, data solidliquidgas
respectively). The bond-dissociation energy of 1072 kJ/mol
is stronger than that of N2 (942 kJ/mol) and represents the Spectral data UV, IR, NMR, MS
strongest chemical bond known.[21] Except where otherwise noted, data are given for
materials in their standard state (at 25 C [77 F],
The ground electronic state of carbon monoxide is a singlet 100 kPa).
state[22] since there are no unpaired electrons. verify (what is ?)
Infobox references
Bonding and dipole moment

Carbon and oxygen together have a total of 10 electrons in the valence shell. Following the octet rule for both
carbon and oxygen, the two atoms form a triple bond, with six shared electrons in three bonding molecular
orbitals, rather than the usual double bond found in organic carbonyl compounds. Since four of the shared
electrons come from the oxygen atom and only two from carbon, one bonding orbital is occupied by two
electrons from oxygen, forming a dative or dipolar bond. This causes a CO polarization of the molecule, with
a small negative charge on carbon and a small positive charge on oxygen. The other two bonding orbitals are
each occupied by one electron from carbon and one from oxygen, forming (polar) covalent bonds with a
reverse CO polarization, since oxygen is more electronegative than carbon. In the free carbon monoxide, a
net negative charge remains at the carbon end and the molecule has a small dipole moment of 0.122 D.[23]

The molecule is therefore asymmetric: oxygen has more electron density than carbon, and is also slightly
positively charged compared to carbon being negative. By contrast, the isoelectronic dinitrogen molecule has
no dipole moment.
If carbon monoxide acts as a ligand, the polarity of the dipole may reverse with a net negative charge on the
oxygen end, depending on the structure of the coordination complex.[24] See also the section "Coordination
chemistry" below.

Bond polarity and oxidation state

Theoretical and experimental studies show that, despite the greater electronegativity of oxygen, the dipole
moment points from the more-negative carbon end to the more-positive oxygen end.[25][26] The three bonds are
in fact polar covalent bonds that are strongly polarized. The calculated polarization toward the oxygen atom is
71% for the -bond and 77% for both -bonds.[27]

The oxidation state of carbon in carbon monoxide is +2 in each of these structures. It is calculated by counting
all the bonding electrons as belonging to the more electronegative oxygen. Only the two non-bonding electrons
on carbon are assigned to carbon. In this count, carbon then has only two valence electrons in the molecule
compared to four in the free atom.

Biological and physiological properties


Toxicity

Carbon monoxide poisoning is the most common type of fatal air poisoning in many countries.[28] Carbon
monoxide is colorless, odorless, and tasteless, but highly toxic. It combines with hemoglobin to produce
carboxyhemoglobin, which usurps the space in hemoglobin that normally carries oxygen, but is ineffective for
delivering oxygen to bodily tissues. Concentrations as low as 667 ppm may cause up to 50% of the body's
hemoglobin to convert to carboxyhemoglobin.[29] A level of 50% carboxyhemoglobin may result in seizure,
coma, and fatality. In the United States, the OSHA limits long-term workplace exposure levels above 50
ppm.[30]

The most common symptoms of carbon monoxide poisoning may resemble other types of poisonings and
infections, including symptoms such as headache, nausea, vomiting, dizziness, fatigue, and a feeling of
weakness. Affected families often believe they are victims of food poisoning. Infants may be irritable and feed
poorly. Neurological signs include confusion, disorientation, visual disturbance, syncope (fainting), and
seizures.[31]

Some descriptions of carbon monoxide poisoning include retinal hemorrhages, and an abnormal cherry-red
blood hue.[32] In most clinical diagnoses these signs are seldom noticed.[31] One difficulty with the usefulness
of this cherry-red effect is that it corrects, or masks, what would otherwise be an unhealthy appearance, since
the chief effect of removing deoxygenated hemoglobin is to make an asphyxiated person appear more normal,
or a dead person appear more lifelike, similar to the effect of red colorants in embalming fluid. The "false" or
unphysiologic red-coloring effect in anoxic CO-poisoned tissue is related to the meat-coloring commercial use
of carbon monoxide, discussed below.

Carbon monoxide also binds to other molecules such as myoglobin and mitochondrial cytochrome oxidase.
Exposures to carbon monoxide may cause significant damage to the heart and central nervous system,
especially to the globus pallidus,[33] often with long-term chronic pathological conditions. Carbon monoxide
may have severe adverse effects on the fetus of a pregnant woman.[34]

Normal human physiology

Carbon monoxide is produced naturally by the human body as a signaling molecule. Thus, carbon monoxide
may have a physiological role in the body, such as a neurotransmitter or a blood vessel relaxant.[35] Because of
carbon monoxide's role in the body, abnormalities in its metabolism have been linked to a variety of diseases,
including neurodegenerations, hypertension, heart failure, and pathological inflammation.[35] Relative to
inflammation, carbon monoxide has been shown to inhibit the movement of leukocytes to inflamed tissues,
stimulate leukocyte phagocytosis of bacteria, and reduce the production of pro-inflammatory cytokines by
leukocytes. In animal model studies, furthermore, carbon monoxide reduced the severity of experimentally
induced bacterial sepsis, pancreatitis, hepatic ischemia/reperfusion injury, colitis, osteoarthritis, lung injury,
lung transplantation rejection, and neuropathic pain while promoting skin wound healing. These actions are
similar to those of Specialized pro-resolving mediators which act to dampen, reverse, and repair the tissue
damage due to diverse inflammation responses. Indeed, carbon monoxide can act additively with one of these
mediators (Resolvin D1) to limit inflammatory responses. The studies implicate carbon monoxide as a
physiological contributor to limiting inflammation and suggest that its delivery by inhalation or carbon
monoxide-forming drugs may be therapeutically useful for controlling pathological inflammatory
responses.[36][37][38][39]

CO functions as an endogenous signaling molecule, modulates functions of the cardiovascular system, inhibits
blood platelet aggregation and adhesion, suppresses, reverses, and repairs the damage caused by inflammatory
responses. It may play a role as potential therapeutic agent.[36][40]

Microbiology

Carbon monoxide is a nutrient for methanogenic archaea, which reduce it to methane using hydrogen.[41] This
is the theme for the emerging field of bioorganometallic chemistry. Extremophile micro-organisms can, thus,
utilize carbon monoxide in such locations as the thermal vents of volcanoes.[42]

Some microbes can convert carbon monoxide to carbon dioxide to yield energy.[43]

In bacteria, carbon monoxide is produced via the reduction of carbon dioxide by the enzyme carbon monoxide
dehydrogenase, an Fe-Ni-S-containing protein.[44]

CooA is a carbon monoxide sensor protein.[45] The scope of its biological role is still unknown; it may be part
of a signaling pathway in bacteria and archaea. Its occurrence in mammals is not established.

Occurrence
Carbon monoxide occurs in various natural and artificial environments.
Typical concentrations in parts per million are as follows:

Composition of dry atmosphere, by volume[47]


ppmv: parts per million by volume (note: volume fraction is equal to mole fraction for ideal gas only,
see volume (thermodynamics))

Concentration Source

0.1 ppmv Natural atmosphere level (MOPITT)[48]


Play media
0.55 ppmv Average level in homes[49] Monthly averages of global
concentrations of tropospheric carbon
Near-properly adjusted gas stoves in homes, modern vehicle
515 ppmv monoxide at an altitude of about 12,000
exhaust emissions[50]
feet. Data were collected by the
17 ppmv Atmosphere of Venus MOPITT (Measurements Of Pollution In
The Troposphere) sensor on NASAs
Exhaust from automobiles in the Mexico City central area in
100200 ppmv Terra satellite.[46]
1975[51]

700 ppmv Atmosphere of Mars

5,000 ppmv Exhaust from a home wood fire[52]

7,000 ppmv Undiluted warm car exhaust without acatalytic converter[50]

Atmospheric presence
Carbon monoxide is present in small amounts in the
atmosphere, chiefly as a product of volcanic activity but
also from natural and man-made fires (such as forest and
bushfires, burning of crop residues, and sugarcane fire-
cleaning). The burning of fossil fuels also contributes to
carbon monoxide production. Carbon monoxide occurs
dissolved in molten volcanic rock at high pressures in the
Earth's mantle.[53] Because natural sources of carbon
monoxide are so variable from year to year, it is extremely
difficult to accurately measure natural emissions of the gas. Play media
The streak of red, orange, and yellow acrossSouth
Carbon monoxide is a short-lived greenhouse gas and also America, Africa, and the Atlantic Ocean in this
has an indirect radiative forcing effect by elevating animation points to high levels of carbon monoxide on
concentrations of methane and tropospheric ozone through September 30, 2005.
chemical reactions with other atmospheric constituents
(e.g., the hydroxyl radical, OH.) that would otherwise
destroy them.[54] Through natural processes in the atmosphere, it is
eventually oxidized to carbon dioxide. Carbon monoxide is both short-
lived in the atmosphere (on average about two months) and spatially
variable in concentration.

In the atmosphere of Venus carbon monoxide occurs as a result of the


photodissociation of carbon dioxide by electromagnetic radiation of
wavelengths shorter than 169 nm.

Due to its long lifetime in the mid-troposphere, carbon monoxide is also Carbon Monoxide concentrations in
used as tracer of transport for pollutant plumes.[55] Northern Hemisphere spring as measured
with the MOPITT instrument.
Urban pollution

Carbon monoxide is a temporary atmospheric pollutant in some urban areas, chiefly from the exhaust of
internal combustion engines (including vehicles, portable and back-up generators, lawn mowers, power
washers, etc.), but also from incomplete combustion of various other fuels (including wood, coal, charcoal, oil,
paraffin, propane, natural gas, and trash).

Large CO pollution events can be observed from space over cities.[56]

Role in ground-level ozone formation

Carbon monoxide is, along with aldehydes, part of the series of cycles of chemical reactions that form
photochemical smog. It reacts with hydroxyl radical (OH) to produce a radical intermediate HOCO, which
transfers rapidly its radical hydrogen to O2 to form peroxy radical (HO2) and carbon dioxide (CO2).[57] Peroxy
radical subsequently reacts with nitrogen oxide (NO) to form nitrogen dioxide (NO2) and hydroxyl radical.
NO2 gives O(3P) via photolysis, thereby forming O3 following reaction with O2. Since hydroxyl radical is
formed during the formation of NO2, the balance of the sequence of chemical reactions starting with carbon
monoxide and leading to the formation of ozone is:

CO + 2O2 + h CO2 + O3

(where h refers to the photon of light absorbed by the NO2 molecule in the sequence)

Although the creation of NO2 is the critical step leading to low level ozone formation, it also increases this
ozone in another, somewhat mutually exclusive way, by reducing the quantity of NO that is available to react
with ozone.[58]
Indoor pollution

In closed environments, the concentration of carbon monoxide can easily rise to lethal levels. On average, 170
people in the United States die every year from carbon monoxide produced by non-automotive consumer
products.[59] However, according to the Florida Department of Health, "every year more than 500 Americans
die from accidental exposure to carbon monoxide and thousands more across the U.S. require emergency
medical care for non-fatal carbon monoxide poisoning"[60] These products include malfunctioning fuel-burning
appliances such as furnaces, ranges, water heaters, and gas and kerosene room heaters; engine-powered
equipment such as portable generators; fireplaces; and charcoal that is burned in homes and other enclosed
areas. The American Association of Poison Control Centers (AAPCC) reported 15,769 cases of carbon
monoxide poisoning resulting in 39 deaths in 2007.[61] In 2005, the CPSC reported 94 generator-related carbon
monoxide poisoning deaths.[59] Forty-seven of these deaths were known to have occurred during power
outages due to severe weather, including Hurricane Katrina.[59] Still others die from carbon monoxide produced
by non-consumer products, such as cars left running in attached garages. The Centers for Disease Control and
Prevention estimates that several thousand people go to hospital emergency rooms every year to be treated for
carbon monoxide poisoning.[62]

Presence in blood

Carbon monoxide is absorbed through breathing and enters the blood stream through gas exchange in the lungs.
It is also produced in heme catabolism and enters the blood from the tissues, and thus is present in all normal
tissues, even if not inhaled.

Normal circulating levels in the blood are 0% to 3%,[63] are higher in smokers. Carbon monoxide levels cannot
be assessed through a physical exam. Laboratory testing requires a blood sample (arterial or venous) and
laboratory analysis on a CO-Oximeter. Additionally, a noninvasive carboxyhemoglobin (SpCO) test method
from Pulse CO-Oximetry exists and has been validated compared to invasive methods.[64]

Astrophysics

Outside of Earth, carbon monoxide is the second-most common molecule in the interstellar medium, after
molecular hydrogen. Because of its asymmetry, the carbon monoxide molecule produces far brighter spectral
lines than the hydrogen molecule, making CO much easier to detect. Interstellar CO was first detected with
radio telescopes in 1970. It is now the most commonly used tracer of molecular gas in general in the interstellar
medium of galaxies, as molecular hydrogen can only be detected using ultraviolet light, which requires space
telescopes. Carbon monoxide observations provide much of the information about the molecular clouds in
which most stars form.[65]

Beta Pictoris, the second brightest star in the constellation Pictor, shows an excess of infrared emission
compared to normal stars of its type, which is caused by large quantities of dust and gas (including carbon
monoxide)[66][67] near the star.

Production
Many methods have been developed for carbon monoxide's production.[68]

Industrial production

A major industrial source of CO is producer gas, a mixture containing mostly carbon monoxide and nitrogen,
formed by combustion of carbon in air at high temperature when there is an excess of carbon. In an oven, air is
passed through a bed of coke. The initially produced CO2 equilibrates with the remaining hot carbon to give
CO. The reaction of CO2 with carbon to give CO is described as the Boudouard reaction.[69] Above 800 C,
CO is the predominant product:
CO2 + C 2 CO (H = 170 kJ/mol)

Another source is "water gas", a mixture of hydrogen and carbon monoxide produced via the endothermic
reaction of steam and carbon:

H2O + C H2 + CO (H = +131 kJ/mol)

Other similar "synthesis gases" can be obtained from natural gas and other fuels.

Carbon monoxide is also a byproduct of the reduction of metal oxide ores with carbon, shown in a simplified
form as follows:

MO + C M + CO

Carbon monoxide is also produced by the direct oxidation of carbon in a limited supply of oxygen or air.

2C(s) + O2 2CO(g)

Since CO is a gas, the reduction process can be driven by heating, exploiting the positive (favorable) entropy of
reaction. The Ellingham diagram shows that CO formation is favored over CO2 in high temperatures.

Laboratory preparation

Carbon monoxide is conveniently produced in the laboratory by the dehydration of formic acid or oxalic acid,
for example with concentrated sulfuric acid.[70][71][72] Another method is heating an intimate mixture of
powdered zinc metal and calcium carbonate, which releases CO and leaves behind zinc oxide and calcium
oxide:

Zn + CaCO3 ZnO + CaO + CO

Silver nitrate and iodoform also afford carbon monoxide:

CHI3 + 3AgNO3 + H2O 3HNO3 + CO + 3AgI

Finally, metal oxalate salts release CO upon heating, leaving a carbonate as byproduct:

Na2C2O4 Na2CO3 + CO

Coordination chemistry
Most metals form coordination complexes
containing covalently attached carbon
monoxide. Only metals in lower oxidation
states will complex with carbon monoxide
ligands. This is because there must be
sufficient electron density to facilitate back-
donation from the metal dxz-orbital, to the *
molecular orbital from CO. The lone pair on The HOMO of CO is a
the carbon atom in CO, also donates electron MO.
density to the dxy on the metal to form a
sigma bond. This electron donation is also
Energy level scheme of the and exhibited with the cis effect, or the labilization of CO ligands in the cis
orbitals of carbon monoxide position. Nickel carbonyl, for example, forms by the direct combination of
carbon monoxide and nickel metal:
Ni + 4 CO Ni(CO)4 (1 bar, 55 C)

For this reason, nickel in any tubing or part must not come into prolonged contact
with carbon monoxide. Nickel carbonyl decomposes readily back to Ni and CO
upon contact with hot surfaces, and this method is used for the industrial
purification of nickel in the Mond process.[73]

In nickel carbonyl and other carbonyls, the electron pair on the carbon interacts
with the metal; the carbon monoxide donates the electron pair to the metal. In
these situations, carbon monoxide is called the carbonyl ligand. One of the most
The LUMO of CO is a *
important metal carbonyls is iron pentacarbonyl, Fe(CO)5:
antibonding MO.

Many metal-CO complexes are prepared by decarbonylation of organic solvents, not from CO. For instance,
iridium trichloride and triphenylphosphine react in boiling 2-methoxyethanol or DMF to afford IrCl(CO)
(PPh3)2.

Metal carbonyls in coordination chemistry are usually studied using infrared spectroscopy.

Organic and main group chemistry


In the presence of strong acids and water, carbon monoxide reacts with alkenes to form carboxylic acids in a
process known as the KochHaaf reaction.[70] In the GattermannKoch reaction, arenes are converted to
benzaldehyde derivatives in the presence of AlCl3 and HCl.[71] Organolithium compounds (e.g. butyl lithium)
react with carbon monoxide, but these reactions have little scientific use.

Although CO reacts with carbocations and carbanions, it is relatively nonreactive toward organic compounds
without the intervention of metal catalysts.[74]

With main group reagents, CO undergoes several noteworthy reactions. Chlorination of CO is the industrial
route to the important compound phosgene. With borane CO forms the adduct H3BCO, which is isoelectronic
with the acetylium cation [H3CCO]+. CO reacts with sodium to give products resulting from C-C coupling such
+
as sodium acetylenediolate 2Na C2O2
2 . It reacts with molten potassium to give a mixture of an organometallic
+ +
compound, potassium acetylenediolate 2K C2O2 2 , potassium benzenehexolate 6K C6O6 ,
6 [75]
and potassium
+
rhodizonate 2K C6O2
6 .
[76]

The compounds cyclohexanehexone or triquinoyl (C6O6) and cyclopentanepentone or leuconic acid (C5O5),
which so far have been obtained only in trace amounts, can be regarded as polymers of carbon monoxide.

At pressures of over 5 gigapascals, carbon monoxide converts into a solid polymer of carbon and oxygen. This
is metastable at atmospheric pressure but is a powerful explosive.[77][78]

Uses
Chemical industry

Carbon monoxide is an industrial gas that has many applications in bulk chemicals manufacturing.[79] Large
Carbon monoxide is an industrial gas that has many applications in bulk chemicals manufacturing.[79] Large
quantities of aldehydes are produced by the hydroformylation reaction of alkenes, carbon monoxide, and H2.
Hydroformylation is coupled to the Shell higher olefin process to give precursors to detergents.

Phosgene, useful for preparing isocyanates, polycarbonates, and polyurethanes, is produced by passing purified
carbon monoxide and chlorine gas through a bed of porous activated carbon, which serves as a catalyst. World
production of this compound was estimated to be 2.74 million tonnes in 1989.[80]

CO + Cl2 COCl2

Methanol is produced by the hydrogenation of carbon monoxide. In a related reaction, the hydrogenation of
carbon monoxide is coupled to C-C bond formation, as in the Fischer-Tropsch process where carbon monoxide
is hydrogenated to liquid hydrocarbon fuels. This technology allows coal or biomass to be converted to diesel.

In the Monsanto process, carbon monoxide and methanol react in the presence of a homogeneous rhodium
catalyst and hydroiodic acid to give acetic acid. This process is responsible for most of the industrial production
of acetic acid.

An industrial scale use for pure carbon monoxide is purifying nickel in the Mond process.

Meat coloring

Carbon monoxide is used in modified atmosphere packaging systems in the US, mainly with fresh meat
products such as beef, pork, and fish to keep them looking fresh. The carbon monoxide combines with
myoglobin to form carboxymyoglobin, a bright-cherry-red pigment. Carboxymyoglobin is more stable than the
oxygenated form of myoglobin, oxymyoglobin, which can become oxidized to the brown pigment
metmyoglobin. This stable red color can persist much longer than in normally packaged meat.[81] Typical levels
of carbon monoxide used in the facilities that use this process are between 0.4% to 0.5%.

The technology was first given "generally recognized as safe" (GRAS) status by the U.S. Food and Drug
Administration (FDA) in 2002 for use as a secondary packaging system, and does not require labeling. In 2004,
the FDA approved CO as primary packaging method, declaring that CO does not mask spoilage odor.[82]
Despite this ruling, the process remains controversial for fears that it masks spoilage.[83][84] In 2007, a bill[85]
was introduced to the United States House of Representatives to label modified atmosphere carbon monoxide
packaging as a color additive, but the bill died in subcommittee. The process is banned in many other countries,
including Japan, Singapore, and the European Union.[86][87][88]

Medicine

In biology, carbon monoxide is naturally produced by the action of heme oxygenase 1 and 2 on the heme from
hemoglobin breakdown. This process produces a certain amount of carboxyhemoglobin in normal persons,
even if they do not breathe any carbon monoxide.

Following the first report that carbon monoxide is a normal neurotransmitter in 1993,[14][15] as well as one of
three gases that naturally modulate inflammatory responses in the body (the other two being nitric oxide and
hydrogen sulfide), carbon monoxide has received a great deal of clinical attention as a biological regulator. In
many tissues, all three gases are known to act as anti-inflammatories, vasodilators, and encouragers of
neovascular growth.[16] However, the issues are complex, as neovascular growth is not always beneficial, since
it plays a role in tumor growth, and also the damage from wet macular degeneration, a disease for which
smoking (a major source of carbon monoxide in the blood, several times more than natural production)
increases the risk from 4 to 6 times.

There is a theory that, in some nerve cell synapses, when long-term memories are being laid down, the
receiving cell makes carbon monoxide, which back-transmits to the transmitting cell, telling it to transmit more
readily in future. Some such nerve cells have been shown to contain guanylate cyclase, an enzyme that is
activated by carbon monoxide.[15]
activated by carbon monoxide.[15]

Studies involving carbon monoxide have been conducted in many laboratories throughout the world for its anti-
inflammatory and cytoprotective properties. These properties have potential to be used to prevent the
development of a series of pathological conditions including ischemia reperfusion injury, transplant rejection,
atherosclerosis, severe sepsis, severe malaria, or autoimmunity. Clinical tests involving humans have been
performed, however the results have not yet been released.[17]

Metallurgy

Carbon monoxide is a strong reductive agent, and whilst not known, it has been used in pyrometallurgy to
reduce metals from ores since ancient times. Carbon monoxide strips oxygen off metal oxides, reducing them to
pure metal in high temperatures, forming carbon dioxide in the process. Carbon monoxide is not usually
supplied as is, in gaseous phase, in the reactor, but rather it is formed in high temperature in presence of
oxygen-carrying ore, carboniferous agent such as coke and high temperature. The blast furnace process is a
typical example of a process of reduction of metal from ore with carbon monoxide.

Lasers

Carbon monoxide has also been used as a lasing medium in high-powered infrared lasers.[89]

Niche uses

Carbon monoxide has been proposed for use as a fuel on Mars. Carbon monoxide/oxygen engines have been
suggested for early surface transportation use as both carbon monoxide and oxygen can be straightforwardly
produced from the atmosphere of Mars by zirconia electrolysis, without using any Martian water resources to
obtain hydrogen, which would be needed to make methane or any hydrogen-based fuel.[90] Likewise, blast
furnace gas collected at the top of blast furnace, still contains some 10% to 30% of carbon monoxide, and is
used as fuel on Cowper stoves and on Siemens-Martin furnaces on open hearth steelmaking.

See also
Metal carbonyl
Boudouard reaction
Carbon monoxide (data page)
Carbon monoxide breath monitor
Carbon monoxide detector
Carbon monoxide poisoning
Criteria air contaminants
List of highly toxic gases
Molecular cloud
Undersea and Hyperbaric Medical Society hyperbaric treatment for CO poisoning
Rubicon Foundation research articles on CO poisoning
Guanylate cyclase
Bridging carbonyl

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External links
Global map of carbon monoxide distribution
Explanation of the structure
Carbon Monoxide Safety Association
International Chemical Safety Card 0023
NIOSH Pocket Guide to Chemical Hazards
CDC Carbon Monoxide NIOSH Workplace Safety and Health Topic
http://www.cdc.gov/co/faqs.htm
External MSDS data sheet
Carbon Monoxide Detector Placement
Carbon Monoxide Purification Process
Microscale Gas Chemistry Experiments with Carbon Monoxide
Instant insight outlining the physiology of carbon monoxide from the Royal Society of Chemistry
Pictures of CO Poisoning Radiology and Pathology Images from MedPix.

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