Determination of chloromethyl methyl ether and bis(chloromethyl ether) in air at the part per billion level by gas-liquid chromatography

Solomon, Richard A.; Kallos, George J.

doi:10.1021/ac60356a007

Cited by 26 publications

(13 citation statements)

References 21 publications

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“…The possibility of any BCME forming at the parts per billion level was checked by the gas chromatographic techniques since direct monitoring with the mass spectrometer did not provide adequate sensitivity. In all reactions, the gas chromatographic method (7) was desirable for the determination of BCME. The results are shown in Table I.…”

Section: Resultsmentioning

confidence: 99%

“…The rubber septa of the three small ball joints were covered on the inside of the reactor with a Teflon sheet to minimize interaction with reactants or products. The joint ports were used for injecting chlorine, dimethyl ether, or BCME gas standards, connecting the 15-head silicone fiber probe (18) to the mass spectrometer, and for connecting the impingers containing the 2,4,6-trichlorophenate derivatizing reagent (7). The impingers were connected to a dry ice trap so that the correct flow of air could be adjusted through the reaction mixture with a needle valve and flow meter.…”

Section: Methodsmentioning

confidence: 99%

“…To determine the level of BCME formation, a reaction was carried out as above for a predetermined time. Then the lamp was turned off, and the products were pulled through two impinger solutions containing the 2,4,6-trichlorophenate reagent and analyzed by the gas chromatographic derivative techniques (7,8). Dry air was drawn through the reactor into the impingers for 40 min at a rate of 0.35 L/min, assuring at least 90% depletion of the sample from the reactor.…”

Section: Methodsmentioning

confidence: 99%

“…Due to major concern of possible industrial exposure, many analytical techniques have been developed to determine or monitor BCME in air at the parts per billion level. These techniques are high-resolution mass spectrometry (3), gas chromatography-mass spectrometry (4), dual-column gas chromatography (5), gas chromatography-high-resolution mass spectrometry (6), and derivative gas chromatography (7,8).…”

mentioning

confidence: 99%

“…Due to this concern and the impact on our industrial environment, a study was undertaken to investigate the possible formation of BCME in diluted gas mixtures of DME and chlorine under photolysis. The reaction under various experimental conditions was followed with a mass spectrometer, and BCME, possibly being generated from the reaction, was determined at several reaction times with the gas chromatographic derivative technique (7,8).…”

mentioning

confidence: 99%

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Study of photolytic oxidation and chlorination reactions of dimethyl ether and chlorine in ambient air

Kallos¹,

Tou²

1977

Environ. Sci. Technol.

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Preliminary studies show that both dimethyl ether and bis(chloromethyl) ether (BCME) are unstable in the presence of chlorine and air under visible and near UV irradiation. The rates of reactions between chlorine and dimethyl ether are dependent on the relative chlorine/dimethyl ether concentrations. The evidence is consistent with a reaction mechanism dependent upon several consecutive chlorine atom sensitized photooxidations. Parts per billion levels of BCME possibly formed during the reactions at various concentrations of chlorine and dimethyl ether up to 300 ppm are determined, and the results are discussed.Bis(chloromethyl) ether (BCME), a carcinogen (1, 2), is most commonly found to be an impurity in chloromethyl methyl ether, a chloromethylating agent used in the manufacture of commercial ion-exchange resins. During the past few years, BCME has been the subject of many investigations concerning methods of analysis, its stability in the environment, and reactions by which it may be formed. Due to major concern of possible industrial exposure, many analytical techniques have been developed to determine or monitor BCME in air at the parts per billion level. These techniques are high-resolution mass spectrometry (3), gas chromatography-mass spectrometry (4), dual-column gas chromatography (5), gas chromatography-high-resolution mass spectrometry (6), and derivative gas chromatography (7,8).

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Study of photolytic oxidation and chlorination reactions of dimethyl ether and chlorine in ambient air

Kallos¹,

Tou²

1977

Environ. Sci. Technol.

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Ethers

Mehlman

2024

Patty's Toxicology

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Naturally occurring ethers may be constituents of essential oils and may be extracted from these sources. Although some ethers may appear naturally, they may be prepared synthetically from other chemicals or other ethers. Symmetrical ethers are produced by the catalytic dehydration of their corresponding alcohols, for example, diethyl ether from ethanol. They are also obtained as by‐products from the formation of their corresponding esters or alcohols. Ethers may also be made by special synthesis procedures. Some ethers are obtained through the destructive distillation of selected hardwoods. Ethers have a wide variety of industrial uses. Their commercial value is recognized in the following industries: rubber, plastics, paints and coatings, refrigeration, medicine, dentistry, petroleum, chemical, perfume, cosmetics, toiletries, and food. The more volatile ethers have been used as liquid refrigerants, general anesthetics, commercial solvents, primers for gasoline engines, fuel additives, and rocket propellants. Other ethers have been used as alkylating agents in chemical syntheses of organic chemicals and in the manufacture of polymers. They are also used to denature alcohol. Halogenated ethers are used in the preparation of ion‐exchange resin, which is a modified polystyrene resin that is chloromethylated and then treated with a tertiary amine or with a polyamine. Ethers have wide use as commercial solvents and extractants for esters, gums, hydrocarbons, alkaloids, oils, resins, dyes, plastics, lacquers, and paints. They are used as dewaxing extractants for lubricating oils. Ethers have had limited use as cleaning and spotting agents. They are used as chemical intermediates in the manufacture of textile aids, such as dyes and resins. In the pharmaceutical industry, ethers are used as solvents, suspending agents, flavorings for oral drugs, and dental products. They are used to increase viscosity, as penetrants and wetting agents and as antioxidants and stabilizers. Ethers are used in foods as flavorings and in perfumes as fragrances. They are used as solvents for elastomers and for regenerating rubber. They have use as antiskinning agents in surface coatings and as weathering agents for paints and plastics. Ethers are also used in soaps. Ethers appear in heat transfer agents. Several industries use specific ethers for thickening, dispersing, suspending, binding, and film forming. The data presented here are arranged according to the chemical structure of the compounds. An effort has been made to place the chemicals within each group in an order that represents an increase in chain length. Even though the number of chemicals in any one group is limited, it is possible to make general, comparative statements. This corresponds with the acute toxicity data available in the NIOSH Registry of Toxic Effects of Chemical Substances . The oral toxicity and concentrated vapor data indicate that as the chain length increases in the symmetrical ethers, the toxicity is reduced. The inverse is true for skin penetration toxicity.

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Ethers

Mehlman¹

2000

Patty's Toxicology

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Naturally occurring ethers may be constituents of essential oils and may be extracted from these sources. Although some ethers may appear naturally, they may be prepared synthetically from other chemicals or other ethers. Symmetrical ethers are produced by the catalytic dehydration of their corresponding alcohols, for example, diethyl ether from ethanol. They are also obtained as by‐products from the formation of their corresponding esters or alcohols. Ethers may also be made by special synthesis procedures. Some ethers are obtained through the destructive distillation of selected hardwoods. Ethers have a wide variety of industrial uses. Their commercial value is recognized in the following industries: rubber, plastics, paints and coatings, refrigeration, medicine, dentistry, petroleum, chemical, perfume, cosmetics, toiletries, and food. The more volatile ethers have been used as liquid refrigerants, general anesthetics, commercial solvents, primers for gasoline engines, fuel additives, and rocket propellants. Other ethers have been used as alkylating agents in chemical syntheses of organic chemicals and in the manufacture of polymers. They are also used to denature alcohol. Halogenated ethers are used in the preparation of ion‐exchange resin, which is a modified polystyrene resin that is chloromethylated and then treated with a tertiary amine or with a polyamine. Ethers have wide use as commercial solvents and extractants for esters, gums, hydrocarbons, alkaloids, oils, resins, dyes, plastics, lacquers, and paints. They are used as dewaxing extractants for lubricating oils. Ethers have had limited use as cleaning and spotting agents. They are used as chemical intermediates in the manufacture of textile aids, such as dyes and resins. In the pharmaceutical industry, ethers are used as solvents, suspending agents, flavorings for oral drugs, and dental products. They are used to increase viscosity, as penetrants and wetting agents, and as antioxidants and stabilizers. Ethers are used in foods as flavorings and in perfumes as fragrances. They are used as solvents for elastomers and for regenerating rubber. They have use as antiskinning agents in surface coatings and as weathering agents for paints and plastics. Ethers are also used in soaps. Ethers appear in heat transfer agents. Several industries use specific ethers for thickening, dispersing, suspending, binding, and film forming. The data presented in here are arranged according to the chemical structure of the compounds. An effort has been made to place the chemicals within each group in an order that represents an increase in chain length. Even though the number of chemicals in any one group is limited, it is possible to make general, comparative statements. This corresponds with the acute toxicity data available in the NIOSH Registry of Toxic Effects of Chemical Substances . The oral toxicity and concentrated vapor data indicate that as the chain length increases in the symmetrical ethers the toxicity is reduced. The inverse is true for skin penetration toxicity.

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Determination of chloromethyl methyl ether and bis(chloromethyl ether) in air at the part per billion level by gas-liquid chromatography

Cited by 26 publications

References 21 publications

Study of photolytic oxidation and chlorination reactions of dimethyl ether and chlorine in ambient air

Study of photolytic oxidation and chlorination reactions of dimethyl ether and chlorine in ambient air

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