Dichloromethane

Last updated
Dichloromethane
Dichloromethane molecular structure.svg
Dichloromethane-3D-vdW.png
Sample of dichloromethane.jpg
Names
Preferred IUPAC name
Dichloromethane
Other names
Methylene bichloride; Methylene chloride gas; Methylene dichloride; Solmethine; Narkotil; Solaesthin; Di-clo; Refrigerant-30; Freon-30; R-30; DCM; MDC
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.763 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-838-9
KEGG
PubChem CID
RTECS number
  • PA8050000
UNII
UN number 1593
  • InChI=1S/CH2Cl2/c2-1-3/h1H2 Yes check.svgY
    Key: YMWUJEATGCHHMB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CH2Cl2/c2-1-3/h1H2
    Key: YMWUJEATGCHHMB-UHFFFAOYAG
  • ClCCl
Properties
CH2Cl2
Molar mass 84.93 g·mol−1
AppearanceColorless liquid
Odor Faint, chloroform-like [1]
Density 1.3266 g/cm3 (20 °C) [2]
Melting point −96.7 °C (−142.1 °F; 176.5 K)
Boiling point 39.6 °C (103.3 °F; 312.8 K)
decomposes at 720 °C [3]
39.75 °C (103.55 °F; 312.90 K)
at 760 mmHg [4]
25.6 g/L (15 °C)
17.5 g/L (25 °C)
15.8 g/L (30 °C)
5.2 g/L (60 °C) [3]
Solubility Miscible in ethyl acetate, alcohol, hexanes, benzene, CCl4, diethyl ether, CHCl3
log P 1.19 [5]
Vapor pressure 0.13 kPa (−70.5 °C)
2 kPa (−40 °C)
19.3 kPa (0 °C)
57.3 kPa (25 °C) [6]
79.99 kPa (35 °C) [3]
3.25 L·atm/mol [4]
−46.6·10−6 cm3/mol
1.4244 (20 °C) [4] [7]
Viscosity 0.43 cP (20 °C) [4]
0.413 cP (25 °C)
Structure
1.6 D
Thermochemistry
102.3 J/(mol·K) [6]
Std molar
entropy (S⦵298)
174.5 J/(mol·K) [6]
−124.3 kJ/mol [6]
-454.0 kJ/mol (from standard enthalpies of formation) [6]
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards
Irritant
GHS labelling: [7]
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H315, H319, H335, H336, H351, H373
P261, P281, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point None, but can form flammable vapor-air mixtures above ≈100 °C [8]
556 °C (1,033 °F; 829 K)
Explosive limits 13%-23% [1]
Lethal dose or concentration (LD, LC):
1.25 g/kg (rats, oral)
2 g/kg (rabbits, oral) [3]
24,929 ppm (rat, 30  min)
14,400 ppm (mouse, 7  h) [9]
5000 ppm (guinea pig, 2 h)
10,000 ppm (rabbit, 7 h)
12,295 ppm (cat, 4.5 h)
14,108 ppm (dog, 7 h) [9]
NIOSH (US health exposure limits):
PEL (Permissible)
25 ppm over 8 hours (time-weighted average), 125 ppm over 15 minutes (STEL) [1] [10]
REL (Recommended)
Ca [1]
IDLH (Immediate danger)
Ca [2300 ppm] [1]
Legal status
Supplementary data page
Dichloromethane (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula C H 2 Cl 2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents. [12]

Contents

Occurrence

Natural sources of dichloromethane include oceanic sources, macroalgae, wetlands, and volcanoes. [13] However, the majority of dichloromethane in the environment is the result of industrial emissions. [13]

Production

DCM is produced by treating either chloromethane or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and chloromethane undergo a series of reactions producing progressively more chlorinated products. In this way, an estimated 400,000 tons were produced in the US, Europe, and Japan in 1993. [12]

CH4 + Cl2 → CH3Cl + HCl
CH3Cl + Cl2 → CH2Cl2 + HCl
CH2Cl2 + Cl2 → CHCl3 + HCl
CHCl3 + Cl2 → CCl4 + HCl

The output of these processes is a mixture of chloromethane, dichloromethane, chloroform, and carbon tetrachloride as well as hydrogen chloride as a byproduct. These compounds are separated by distillation.

DCM was first prepared in 1839 by the French chemist Henri Victor Regnault (1810–1878), who isolated it from a mixture of chloromethane and chlorine that had been exposed to sunlight. [14]

Uses

DCM's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes. [12] In the food industry, it is used to decaffeinate coffee and tea as well as to prepare extracts of hops and other flavourings. [15] [16] Its volatility has led to its use as an aerosol spray propellant and as a blowing agent for polyurethane foams.

Specialized uses

Near IR absorption spectrum of dichloromethane showing complicated overlapping overtones of mid IR absorption features Dichloromethane near IR spectrum.png
Near IR absorption spectrum of dichloromethane showing complicated overlapping overtones of mid IR absorption features

The chemical compound's low boiling point allows the chemical to function in a heat engine that can extract mechanical energy from small temperature differences. An example of a DCM heat engine is the drinking bird. The toy works at room temperature. [17] It is also used as the fluid in jukebox displays and holiday bubble lights that have a colored bubbling tube above a lamp as a source of heat and a small amount of rock salt to provide thermal mass and a nucleation site for the phase changing solvent.

DCM chemically welds certain plastics. For example, it is used to seal the casing of electric meters. Often sold as a main component of plastic welding adhesives, it is also used extensively by model building hobbyists for joining plastic components together. It is commonly referred to as "Di-clo".

It is used in the garment printing industry for removal of heat-sealed garment transfers.

DCM is used in the material testing field of civil engineering; specifically it is used during the testing of bituminous materials as a solvent to separate the binder from the aggregate of an asphalt or macadam to allow the testing of the materials. [18]

Dichloromethane extract of Asparagopsis taxiformis , a seaweed fodder for cattle, has been found to reduce their methane emissions by 79%. [19]

It has been used as the principal component of various paint and lacquer strippers, although its use is now restricted in the EU and many such products now use benzyl alcohol as a safer alternative.

Chemical reactions

Dichloromethane is widely used as a solvent in part because it is relatively inert. It does participate in reactions with certain strong nucleophiles however. Tert-butyllithium deprotonates DCM: [20]

H2CCl2 + RLi → HCCl2Li + RH

Methyllithium reacts with methylene chloride to give chlorocarbene:[ citation needed ]

CH2Cl2 + CH3Li → CHCl + CH4 + LiCl

Although DCM is a common solvent in organic chemistry laboratories and is commonly assumed to be inert, it does react with some amines and triazoles. [21] Tertiary amines can react with DCM to form quaternary chloromethyl chloride salts via the Menshutkin reaction. [22] Secondary amines can react with DCM to yield an equilibrium of iminium chlorides and chloromethyl chlorides, which can react with a second equivalent of the secondary amine to form aminals. [23] At increased temperatures, pyridines including DMAP, react with DCM to form methylene bispyridinium dichlorides. [24] Hydroxybenzotriazole and related reagents used in peptide coupling react with DCM in the presence of triethylamine, forming acetals. [25]

Toxicity

Serious health risks are associated with DCM, despite being one of the least toxic simple chlorohydrocarbons. Its high volatility makes it an inhalation hazard. [26] [27] It can also be absorbed through the skin. [1] [28] Symptoms of acute overexposure to dichloromethane via inhalation include difficulty concentrating, dizziness, fatigue, nausea, headaches, numbness, weakness, and irritation of the upper respiratory tract and eyes. More severe consequences can include suffocation, loss of consciousness, coma, and death. [1] [28]

DCM is also metabolized to carbon monoxide potentially leading to carbon monoxide poisoning. [29] Acute exposure by inhalation has resulted in optic neuropathy [30] and hepatitis. [31] Prolonged skin contact can result in DCM dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns. [32]

It may be carcinogenic, as it has been linked to cancer of the lungs, liver, and pancreas in laboratory animals. [33] Other animal studies showed breast cancer and salivary gland cancer. Research is not yet clear as to what levels may be carcinogenic to humans. [1] [28] DCM crosses the placenta but fetal toxicity in women who are exposed to it during pregnancy has not been proven. [34] In animal experiments, it was fetotoxic at doses that were maternally toxic but no teratogenic effects were seen. [33]

In people with pre-existing heart problems, exposure to DCM can cause abnormal heart rhythms and/or heart attacks, sometimes without any other symptoms of overexposure. [28] People with existing liver, nervous system, or skin problems may worsen after exposure to methylene chloride. [10]

Regulation

In many countries, products containing DCM must carry labels warning of its health risks. Concerns about its health effects have led to a search for alternatives in many of its applications. [12] [35]

In the European Union, the Scientific Committee on Occupational Exposure Limit Values (SCOEL) recommends an occupational exposure limit for DCM of 100 ppm (8-hour time-weighted average) and a short-term exposure limit of 200 ppm for a 15-minute period. [36] The European Parliament voted in 2009 to ban the use of DCM in paint-strippers for consumers and many professionals, [37] with the ban taking effect in December 2010. [38]

In February 2013, the US Occupational Safety and Health Administration (OSHA) and the National Institute for Occupational Safety and Health warned that at least 14 bathtub refinishers have died since 2000 from DCM exposure. These workers had been working alone, in poorly ventilated bathrooms, with inadequate or no respiratory protection, and no training about the hazards of DCM. [10] [28] [39] OSHA has since then issued a DCM standard. [40]

On March 15, 2019, the US Environmental Protection Agency (EPA) issued a final rule to prohibit the manufacture (including importing and exporting), processing, and distribution of DCM in all paint removers for consumer use, effective in 180 days. However, it does not affect other products containing DCM, including many consumer products not intended for paint removal. On April 20, 2023, the EPA proposed a widespread ban on the production of DCM with some exceptions for military and industrial uses. [41] On April 30, 2024, the EPA finalized a ban on most commercial uses of DCM, which mainly banned its application for stripping paint and degreasing surfaces but allowed for some remaining commercial applications, such as chemical production. [42]

Environmental effects

CH2Cl2 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion. CH2Cl2 mm.png
CH2Cl2 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion.

Dichloromethane is not classified as an ozone-depleting substance by the Montreal Protocol. [43] The US Clean Air Act does not regulate dichloromethane as an ozone depleter. [44] Dichloromethane has been classified as a very short-lived substance (VSLS). Despite their short atmospheric lifetimes of less than 0.5 year, VSLSs can contribute to stratospheric ozone depletion, particularly if emitted in regions where rapid transport to the stratosphere occurs. [45] Atmospheric abundances of dichloromethane have been increasing in recent years.

See also

Related Research Articles

<span class="mw-page-title-main">Phosgene</span> Toxic gaseous compound (COCl2)

Phosgene is an organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

<span class="mw-page-title-main">Isocyanate</span> Chemical group (–N=C=O)

In organic chemistry, isocyanate is the functional group with the formula R−N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

Chloroform, or trichloromethane, is an organochloride with the formula CHCl3 and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and PTFE. Chloroform was once used as an inhalational anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

<span class="mw-page-title-main">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known as perchloroethylene or under the systematic name tetrachloroethene, and abbreviations such as perc, and PCE, is a chlorocarbon with the formula Cl2C=CCl2. It is a non-flammable, stable, colorless and heavy liquid widely used for dry cleaning of fabrics. It also has its uses as an effective automotive brake cleaner. It has a mild sweet, sharp odor, detectable by most people at a concentration of 50 ppm.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Solvent, now banned for ozone depletion

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and as such use has declined since 1996. Trichloroethane should not be confused with the similar-sounding trichloroethene which is also commonly used as a solvent.

<span class="mw-page-title-main">Hydrogen bromide</span> Chemical compound

Hydrogen bromide is the inorganic compound with the formula HBr. It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temperature. Aqueous solutions that are 47.6% HBr by mass form a constant-boiling azeotrope mixture that boils at 124.3 °C (255.7 °F). Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid generates the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor. The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Dimethoxymethane</span> Chemical compound

Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.

<span class="mw-page-title-main">Bromochloromethane</span> Chemical compound

Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.

<span class="mw-page-title-main">1-Bromopropane</span> Chemical compound

1-Bromopropane (n-propylbromide or nPB) is a bromoalkane with the chemical formula CH3CH2CH2Br. It is a colorless liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of chloro­fluoro­carbons and chloro­alkanes such as 1,1,1-trichloroethane under the Montreal Protocol.

<span class="mw-page-title-main">Chloroacetyl chloride</span> Chemical compound

Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical.

<span class="mw-page-title-main">Perchloromethyl mercaptan</span> Chemical compound

Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.

<i>m</i>-Xylylenediamine Chemical compound

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.

References

  1. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0414". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 3.164. ISBN   1-4398-5511-0.
  3. 1 2 3 4 Properties of Dichloromethane. chemister.ru
  4. 1 2 3 4 CID 6344 from PubChem
  5. ↑ "Dichloromethane_msds".
  6. 1 2 3 4 5 Methylene chloride in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-26)
  7. 1 2 Sigma-Aldrich Co., Dichloromethane. Retrieved on 2014-05-26.
  8. ↑ "Real time measurement of dichloromethane containing mixtures" (PDF). Health & Safety Laboratory. Retrieved 5 August 2015.
  9. 1 2 "methylene chloride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  10. 1 2 3 "Methylene Chloride Hazards for Bathtub Refinishers". OSHA-NIOSH Hazard Alert 2013-110. OSHA and NIOSH. Retrieved 22 January 2015.
  11. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  12. 1 2 3 4 Rossberg, M. et al. (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a06_233.pub2.
  13. 1 2 Gribble, Gordon W. (2009). Naturally Occurring Organohalogen Compounds. Springer. ISBN   978-3211993248.
  14. ↑ Regnault, V. (1839) "De l'action du chlore sur les éthers hydrochloriques de l'alcool et de l'esprit de bois, et de plusieurs points de la théorie des éthers" (On the action of chlorine on the hydrochloric ethers of ethanol and methanol, and on several points of the theory of ethers), Annales de chimie et physique, series 2, 71 : 353–431; see especially: "Seconde partie. De l'action du chlore sur l'éther hydrochlorique de l'esprit de bois" (Second part. On the action of chlorine on the hydrochloric ether of methanol [i.e., chloromethane]), pages 377–380. Regnault gives dichloromethane the name éther hydrochlorique monochloruré (monochlorinated hydrochloric ether). Note: Regnault gives the empirical formula for dichloromethane as C2H4Cl4 because during that era, chemists used incorrect atomic masses.
    Reprinted in German in:
  15. ↑ Office of Environmental Health Hazard Assessment (September 2000). "Dichloromethane" (PDF). Public Health Goals for Chemicals in Drinking Water. California Environmental Protection Agency . Retrieved June 5, 2016.[ permanent dead link ]
  16. ↑ James2014-04-09T00:00:00+01:00, Emily. "Dichloromethane". Chemistry World.{{cite web}}: CS1 maint: numeric names: authors list (link)
  17. ↑ Perelman, Yakov (1972) [1936]. Physics for Entertainment. Vol. 2. Hyperion Books. pp. 175–178. ISBN   978-1401309213.
  18. ↑ Shell Bitumen (2003-09-25). The Shell Bitumen Handbook. Thomas Telford. ISBN   978-0-7277-3220-0.
  19. ↑ Machado, Lorenna; Magnusson, Marie; Paul, Nicholas; Tomkins, Nigel (2016). "Identification of bioactives from the red seaweed Asparagopsis taxiformis that promote antimethanogenic activity in vitro". Journal of Applied Phycology. 28 (5): 3117–3126. Bibcode:2016JAPco..28.3117M. doi: 10.1007/s10811-016-0830-7 .
  20. ↑ Matteson, Donald S.; Majumdar, Debesh (1983). "Homologation of boronic esters to .alpha.-chloro boronic esters". Organometallics. 2 (11): 1529–1535. doi:10.1021/om50005a008.
  21. ↑ Mills, John E.; Maryanoff, Cynthia A.; Cosgrove, Robin M.; Scott, Lorraine; McComsey, David F. (1984). "The Reaction of Amines with Methylene Chloride. A Brief Review". Organic Preparations and Procedures International. 16 (2): 97–114. doi:10.1080/00304948409356172. ISSN   0030-4948.
  22. ↑ Dunlap, Lee E.; Olson, David E. (2018-05-31). "Reaction of N , N -Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions". ACS Omega. 3 (5): 4968–4973. doi:10.1021/acsomega.8b00507. ISSN   2470-1343. PMC   5981293 . PMID   29876537.
  23. ↑ Mills, John E.; Maryanoff, Cynthia A.; McComsey, David F.; Stanzione, Robin C.; Scott, Lorraine (1987). "Reaction of amines with methylene chloride. Evidence for rapid aminal formation from N-methylenepyrrolidinium chloride and pyrrolidine". The Journal of Organic Chemistry. 52 (9): 1857–1859. doi:10.1021/jo00385a038. ISSN   0022-3263.
  24. ↑ Rudine, Alexander B.; Walter, Michael G.; Wamser, Carl C. (2010-06-18). "Reaction of Dichloromethane with Pyridine Derivatives under Ambient Conditions". The Journal of Organic Chemistry. 75 (12): 4292–4295. doi:10.1021/jo100276m. ISSN   0022-3263. PMID   20469919.
  25. ↑ Ji, Jian-guo; Zhang, De-yi; Ye, Yun-hua; Xing, Qi-yi (1998). "Studies on the reactions of HOBt, HOOBt, HOSu with dichloroalkane solvents". Tetrahedron Letters. 39 (36): 6515–6516. doi:10.1016/S0040-4039(98)01406-3.
  26. ↑ Rioux JP, Myers RA (1988). "Methylene chloride poisoning: a paradigmatic review". J Emerg Med. 6 (3): 227–238. doi:10.1016/0736-4679(88)90330-7. PMID   3049777.
  27. ↑ CDC (2012). "Fatal Exposure to Methylene Chloride Among Bathtub Refinishers — United States, 2000–2011". MMWR. 61 (7): 119–122. PMID   22357403.
  28. 1 2 3 4 5 Hall, Ronald M. (4 February 2013). "Dangers of Bathtub Refinishing". National Institute for Occupational Safety and Health. Retrieved 21 January 2015.
  29. ↑ Fagin J, Bradley J, Williams D (1980). "Carbon monoxide poisoning secondary to inhaling methylene chloride". Br Med J. 281 (6253): 1461. doi:10.1136/bmj.281.6253.1461. PMC   1714874 . PMID   7437838.
  30. ↑ Kobayashi A, Ando A, Tagami N, Kitagawa M, Kawai E, Akioka M, Arai E, Nakatani T, Nakano S, Matsui Y, Matsumura M (2008). "Severe optic neuropathy caused by dichloromethane inhalation". J Ocul Pharmacol and Ther. 24 (6): 607–612. doi:10.1089/jop.2007.0100. PMID   19049266.
  31. ↑ Cordes DH, Brown WD, Quinn KM (1988). "Chemically induced hepatitis after inhaling organic solvents". West J Med. 148 (4): 458–460. PMC   1026148 . PMID   3388849.
  32. ↑ Wells GG, Waldron HA (1984). "Methylene chloride burns". Br J Ind Med. 41 (3): 420. doi:10.1136/oem.41.3.420. PMC   1009322 . PMID   6743591.
  33. 1 2 USDHHS. "Toxicological Profile for Methylene Chloride" (PDF). Retrieved 2006-09-10.
  34. ↑ Bell BP, Franks P, Hildreth N, Melius J (1991). "Methylene chloride exposure and birthweight in Monroe County, New York". Environ Res. 55 (1): 31–9. Bibcode:1991ER.....55...31B. doi:10.1016/S0013-9351(05)80138-0. PMID   1855488.
  35. ↑ "Summary of Regulations Controlling Air Emissions from Paint Stripping and Miscellaneous Surface Coating Operations" (PDF). NESHAP (Subpart HHHHHH) . US Environmental Protection Agency. April 2008. Archived from the original (PDF) on 2016-11-23.
  36. ↑ Recommendation from the Scientific Committee on Occupational Exposure Limits for methylene chloride (dichloromethane) (PDF). European Chemicals Agency (Report). June 2009. Retrieved 2023-09-07.
  37. ↑ "EU Banning Most DCM Paint Strippers". PaintSquare News. 2012-03-09. Retrieved 2023-09-07.
  38. ↑ "COMMISSION REGULATION (EU) No 276/2010 (Official Journal of the European Union, L 86/7)". 2010-04-01. Retrieved 2012-02-07.
  39. ↑ OSHA QuickTakes, February 1, 2013;
  40. ↑ Methylene Chloride. Occupational Safety & Health Administration. osha.gov
  41. ↑ "EPA Proposes Ban on All Consumer, Most Industrial and Commercial Uses of Methylene Chloride to Protect Public Health". 2023-04-20.
  42. ↑ "Biden-Harris Administration Finalizes Ban on Most Uses of Methylene Chloride, Protecting Workers and Communities from Fatal Exposure". 2024-04-30.
  43. ↑ United States Environmental Protection Agency (2015-07-17). "Ozone-Depleting Substances" . Retrieved April 20, 2018.
  44. ↑ United States Environmental Protection Agency (October 1995). "Questions and Answers on Ozone-Depleting Solvents and Their Substitutes" . Retrieved April 20, 2018.
  45. ↑ World Meteorological Organization, United Nations Environmental Program (15 April 2020). "Scientific Assessment of Ozone Depletion: 2018". Archived from the original on December 18, 2023.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.