Йодистый метил: свойства, применение и опасность

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| ImageFile = Methyl iodide. svg
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| ImageName = Stereo skeletal formula of iodomethane with all explicit hydrogens added
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| PIN = Iodomethane
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| LCLo = 3800ppm (rat, 15min) It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

Like many organoiodide compounds, iodomethane is typically stored in dark bottles to inhibit degradation caused by light to give iodine, giving degraded samples a purplish tinge. Commercial samples may be stabilized by copper or silver wire.

In the Monsanto process and the Cativa process, MeI forms in situ from the reaction of methanol and hydrogen iodide. The CH3I then reacts with carbon monoxide in the presence of a rhodium or iridium complex to form acetyl iodide, the precursor to acetic acid after hydrolysis. The Cativa process is usually preferred because less water is required to use and there are less byproducts. MeI is used to prepare the Grignard reagent, methylmagnesium iodide ("MeMgI"), a common source of "Me−". The use of MeMgI has been somewhat superseded by the commercially available methyllithium. MeI can also be used to prepare dimethylmercury, by reacting 2 moles of MeI with a 2/1 molar sodium amalgam (2 moles of sodium, 1 mol of mercury). Iodomethane and other organic iodine compounds do form under the conditions of a serious nuclear accident, after both Chernobyl and Fukushima, Iodine 131 was detected in organic iodine compounds in Europe and Japan respectively.

Iodomethane had also been proposed for use as a fungicide, herbicide, insecticide, nematicide, and as a soil disinfectant, replacing methyl bromide (also known as bromomethane) (banned under the Montreal Protocol). Manufactured by Arysta LifeScience and sold under the brand name MIDAS, iodomethane is registered as a pesticide in the U. S., Mexico, Morocco, Japan, Turkey, and New Zealand and registration is pending in Australia, Guatemala, Costa Rica, Chile, Egypt, Israel, South Africa and other countries. The first commercial applications of MIDAS soil fumigant in California began in Fresno County, in May, 2011. Iodomethane had been approved for use as a pesticide by the United States Environmental Protection Agency in 2007 as a pre plant biocide used to control insects, plant parasitic nematodes, soil borne pathogens, and weed seeds. The compound was registered for use as a preplant soil treatment for field grown strawberries, peppers, tomatoes, grape vines, ornamentals and turf and nursery grown strawberries, stone fruits, tree nuts, and conifer trees. After the discovery phase in a consumer lawsuit, the manufacturer withdrew the fumigant citing its lack of market viability. The use of iodomethane as a fumigant has drawn concern. For example, 54 chemists and physicians contacted the U. S. EPA in a letter, saying "We are skeptical of U. S. EPA's conclusion that the high levels of exposure to iodomethane that are likely to result from broadcast applications are 'acceptable' risks. U. S. EPA has made many assumptions about toxicology and exposure in the risk assessment that have not been examined by independent scientific peer reviewers for adequacy or accuracy. Additionally, none of U. S. EPA's calculations account for the extra vulnerability of the unborn fetus and children to toxic insults." EPA Assistant Administrator Jim Gulliford replied saying, "We are confident that by conducting such a rigorous analysis and developing highly restrictive provisions governing its use, there will be no risks of concern," and in October the EPA approved the use of iodomethane as a soil fumigant in the United States. The California Department of Pesticide Regulation (DPR) concluded that iodomethane is "highly toxic," that "any anticipated scenario for the agricultural or structural fumigation use of this agent would result in exposures to a large number of the public and thus would have a significant adverse impact on the public health", and that adequate control of the chemical in these circumstances would be "difficult, if not impossible." Iodomethane was approved as a pesticide in California that December. A lawsuit was filed on January 5, 2011, challenging California's approval of iodomethane. Subsequently, the manufacturer withdrew the fumigant and requested that California Department of Pesticide Regulation cancel its California registration, citing its lack of market viability. The Centers for Disease Control and Prevention (CDC) lists inhalation, skin absorption, ingestion, and eye contact as possible exposure routes with target organs of the eyes, skin, respiratory system, and the central nervous system. Symptoms may include eye irritation, nausea, vomiting, dizziness, ataxia, slurred speech, and dermatitis. In high dose acute toxicity, as may occur in industrial accidents, toxicity includes metabolic disturbance, renal failure, venous and arterial thrombosis and encephalopathy with seizures and coma, with a characteristic pattern of brain injury. Iodomethane has an for oral administration to rats 76 mg/kg, and is rapidly converted in the liver to S methylglutathione. In its risk assessment of iodomethane, the U. S. EPA conducted an exhaustive scientific and medical literature search over the past 100 years for reported cases of human poisonings attributable to the compound. Citing the EPA as its source, the California Department of Pesticide Regulation said: "Over the past century, only 11 incidents of iodomethane poisoning have been reported in the published literature." "An updated literature search on May 30, 2007 for iodomethane poisoning produced only one additional case report." All but one were industrial—not agricultural—accidents, and the remaining case of poisoning was an apparent suicide. Iodomethane is routinely and regularly used in industrial processes as well as in most university and college chemistry departments for study and learning related to a variety of organic chemical reactions.

The U. S. National Institute for Occupational Safety and Health (NIOSH), the U. S. Occupational Safety and Health Administration and the U. S. Centers for Disease Control and Prevention consider iodomethane a potential occupational carcinogen. The International Agency for Research on Cancer concluded based on studies performed after methyl iodide was put on the Proposition 65 list that: "Methyl iodide is not classifiable as to its carcinogenicity to humans (Group 3)." as of 2007 the Environmental Protection Agency classifies it as "not likely to be carcinogenic to humans in the absence of altered thyroid hormone homeostasis," i. e. it is a human carcinogen but only at doses large enough to disrupt thyroid function (via excess iodide). However this finding is disputed by the Pesticide Action Network, which states that the EPA's assessment "appears to be based solely on a single rat inhalation study in which 66% of the control group and 54 62% of the rats in the other groups died before the end of the study". They go on to state: "The EPA appears to be dismissing early peer reviewed studies in favor of two nonpeer reviewed studies conducted by the registrant that are flawed in design and execution." Despite requests by the U. S. EPA to the Pesticide Action Network to bring forth scientific evidence of their claims, they have not done so.

Sulikowski, G. A.; Sulikowski, M. M. (1999). in Coates, R. M.; Denmark, S. E. (Eds.) Handbook of Reagents for Organic Synthesis, Volume 1: Reagents, Auxiliaries and Catalysts for C C Bond Formation New York: Wiley, pp. 423–26.