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Agricultural Chemicals
Animal Nutrients
Catalysts
Electronics
Explosives
Fuel Additives
Gas and Oil Treatment
Paper Chemicals
Personal Care
Pharmaceuticals
Photographic Chemicals
Resin Manufacturing
Rocket Fuels
Rubber Chemicals
Solvents
Surfactants
Water Treatment
Other Uses
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Agricultural Chemicals
(Mono-, Di-, and Trimethylamine)
Methylamines are used to make intermediates for a wide range of agricultural chemicals, including herbicides, fungicides, insecticides, biocides, and miticides. Agricultural chemicals are one of the widest uses for methylamines.
One use for monomethylamine is to produce metam-sodium (n-methyldithiocarbamate), which is a soil fumigant and sterilant. It is made from the reaction of MMA, carbon disulfide, and caustic. Its applications are increasing, and it is currently used for potatoes, tomatoes, and home and garden applications. It is replacing methyl bromide as a soil fumigant, due to concerns of methyl bromide being a possible ozone depleter.
MMA is also phosgenated to make methyl isocyanate, which is used to make carbaryl, aldicarb, and trimethocarb. The insecticides carbofuran and carbosulfan are produced from these. Monomethylformamide (MMF), made from MMA and carbon monoxide, is being used to make methyl isocyanate in situ, due to concerns of storing and transporting this highly toxic material. MMF, sold by DuPont, can also be used as a solvent for other applications.
Dimethylamine is used to produce the herbicide 2,4-D (2,4-dichlorophenoxyacetic acid). Its DMA salt improves the water solubility of pesticide formulations. Related agricultural products include the ferric reaction with N,N-dimethyl dithiocarbamate to make ferbam, a fungicide for apples and tobacco; the zinc reaction to make ziram, a fungicide for vegetables; and thiram (tetramethylthiuram disulfide), a disinfectant for grains, bulbs, tubers,
and corn.
Other products from DMA include the herbicides diuron, linuron, hexazinone, and fluometuron. Quaternary biocides are produced from alkyldimethylamine (from DMA) and dialkylmethylamine (from MMA). Salts of DMA reacted with substituted naphthaquinones are used to make miticides and aphicides. DMA is also used to produce systemic insecticides such as octamethylpyrophosphoramide (OMPA) (schradan) that are absorbed into the plant rendering it toxic to sapsucking
insects. Trimethylamine reacted with sulfur dioxide has been used to produce a volatile insecticide.
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Animal Nutrients
(Trimethylamine)
The largest use for trimethylamine (TMA) is in the production of choline chloride, a B vitamin supplement in animal feed for chickens, turkeys, and swine. It is made from the reaction of TMA with hydrochloric acid and ethylene oxide or TMA and ethylene chlorohydrin to make this quaternary ammonium compound. The intermediate, TMAhydrochloride, has many uses in other industries as well, such as electronics.
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Catalysts
(Mono-, Di-, and Trimethylamine)
Methylamines are used directly as catalysts or as raw materials to produce other compounds with catalytic activity. MDEA (see Gas and Oil Treatment) made from MMA is used as a urethane catalyst. DMAE (see Water Treatment) made from DMA is also used as a urethane catalyst to promote foam rise and gel strength for insulation applications, such as refrigerators. DMAPA (see Personal
Care) is also used as a urethane catalyst. It is made from the reaction of dimethylamine with acrylonitrile, followed by hydrogenation.
Hydrochlorides of MMA and DMA in the presence of cupric chloride are used for the polymerization of acetylene to vinyl and divinyl acetylene. MMA and DMA are used as catalysts for the dealdolization of diacetone alcohol. TMA is a catalyst for ethyl alcohol to ethylene oxide and for Diels-Alder diene association reactions. DMA and calcium sulfate are used to prepare dinitroalkanes and nitroolefins. MMA and DMA can be used for the condensation of phenol and formaldehyde. DMA is a catalyst to condense acetone with formaldehyde to produce synthetic resins used in paper bonding and coating.
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Electronics
(Di- and Trimethylamine)
Dimethylamine and benzyl chloride are used to make benzyldimethylamine, which can be used as an accelerator for epoxy resins in laminates for electrical equipment. Tetramethylammonium hydroxide from TMA is a stripper for resists in printed circuit boards. TMA-hydrochloride is used to make specialty chemicals for the electronics industry.
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Explosives
(Mono-, Di-, and Trimethylamine)
Water gel explosives have been used in the mining industry due to their ease and safety in handling. The prime ingredient is monomethylamine nitrate made from MMA, formaldehyde, and ammonium nitrate. Perchlorates of mono-, di-, and trimethylamine have also been used in the mining industry.
There have been some military uses for 2,4,6- trinitrophenylmethyl nitramine made from the nitration of dinitromethylaniline with nitric acid. Dinitromethylaniline is the product of MMA plus dinitrochlorobenzene in the presence of caustic. Fuses have been made from trimethylamine with nitric acid and nitrous perchlorate-paraffin mixtures.
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Fuel Additives
(Mono-, Di-, and Trimethylamine)
Fuel additives are used to improve engine performance in a variety of ways. DMCHA and DMAPA (see Personal Care) are used for gasoline and motor oil additives. MMA and chlorobenzene are reacted with copper as a catalyst to make n-methylaniline for aviation fuel. DMA hydrochloride is also used as an additive in aviation fuel as an antiknock compound. MMA nitrate is a freezing point depressant in jet engines using ammonium nitrate-urea fuels. Mixtures of MMA, DMA, and TMA in water have been tested as coolants in some high-speed
engines.
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Gas and Oil Treatment
(Mono- and Dimethylamine)
Alkylalkanolamines have a large use in the treatment of natural gas and oil. Two of the largest volume alkylalkanolamines, methyldiethanolamine (MDEA) and monomethylethanolamine (NMEA), are made from the reaction of monomethylamine and ethylene oxide. MDEA is especially important in removing acidic components in natural gas such as hydrogen sulfide, mercaptans, carbonyl sulfide, and carbon monoxide. Dimethylammonium dimethylcarbamate, made from the reaction of dimethylamine and carbon dioxide, is used to remove sulfur compounds, olefins, and aromatic hydrocarbons from raw oil.
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Paper Chemicals
(Di- and Trimethylamine)
Trimethylamine is used to make paper chemicals such as its reaction with epichlorohydrin to make 3-chloro-2-hydroxypropyltrimethylammonium chloride and the epoxy product glyciditrimethylammonium chloride. These are both used as cationizing starches. DMDAC (see Surfactants) from dimethylamine is also used in the paper industry.
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Personal Care
(Dimethylamine)
The personal care industry is an area with growing use for methylamines as raw materials. N,N-dimethylaminopropylamine (DMAPA) and DMDAC (see Water Treatment) are used to make cosmetics.
DMAPA is also an intermediate for betaines and fatty amide/amine oxides for liquid soaps. DMAE (see Water Treatment) is reacted in polymers for hair products and cosmetics, as well as other personal care items such as hand lotions, shaving creams, and shampoos.
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Pharmaceuticals
(Mono- and Dimethylamine)
The manufacture of intermediates to make pharmaceuticals is one of the most diverse uses of methylamines. The reaction of monomethylamine and ethylene oxide creates two key intermediates: methyldiethanolamine (MDEA) and monomethylethanolamine (NMEA) (see Gas and Oil Treatment). MDEA is used to make analgesics with sedative and antispasmodic effects, such as meperidine.
MMA reacted with phosgene or carbon dioxide yields N,N'dimethylurea. This is used to make xanthine derivatives, such as caffeine and theophylline. The reaction of MMA and phenylsuccinic acid yields phensuximide, an anticonvulsant. N-benzyl-n-methylamine is used in pharmaceuticals. MMA is also used to make intermediates for chlordiazepoxide and lorazepam tranquilizers, nortryptylene antidepressant, isometheptene veterinary smooth muscle relaxant, iothalamic acid x-ray contrast medium, and levothyroxine.
Sympathomimetic drugs are made from MMA, such as adrenaline (amination of 3,4-dihydroxyphenyl chloromethyl ketone from pyrocatechol), ephidrine (reductive amination of phenylmethyl diketone), neosynephrine, vanedrine, and veritol.
Dimethylamine is used to make DMAE (see Water Treatment), which has many uses to produce pharmaceuticals. It is used to make antihistamines, such as pheniramine, chlorpheniramine, and diphenhydramine, for the symptomatic relief of allergies, such as hay fever. DMAE is also used in the synthesis of local anesthetics, such as amethocaine, procaine, and pontocaine.
Propoxyphene analgesic and doxepin antidepressant are made from DMA. Salicylates of both MMA and DMA are used as ointments for skin disorders. DMA is used to make intermediates for tranquilizing agents.
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Photographic Chemicals
(Monomethylamine)
P-methylaminophenol sulfate, used as a photographic developer, is made by using monomethylamine to replace an hydroxyl group on hydroquinone. N-methyl acetoacetamide, used as a coupling agent for pigment manufacture, is produced from MMA and diketene. MDEA (see Gas and Oil Treatment) has a growing use in making other photographic chemicals.
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Resin Manufacturing
(Di- and Trimethylamine)
Methylamines are used to make resins for water demineralization and deionization. Cationic exchange resins are made from trimethylamine reacted with chloromethylated polystyrene-divinyl benzene copolymers. Anionic resins are made from adding dimethylamine and hydrochloric acid to melamine formaldehyde condensation products.
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Rocket Fuels
(Dimethylamine)
1,1-dimethylhydrazine is used as a propellant for booster rockets. It has replaced hydrazine in some applications, because it is more soluble in petroleum fuels and has a lower freezing point. It is made from dimethylamine salt and sodium nitrite to make dimethylnitrosamine, which is reduced using zinc, or it can be directly oxidized with chloramine.
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Rubber Chemicals
(Dimethylamine)
Dimethylamine is used in several applications in the rubber industry. Dimethyldithiocarbamate salts are used for vulcanization accelerators. Tetramethylthiuram mono- and disulfide (TMTD) is a rubber accelerator, especially for butyl rubbers. DMA oleate is an emulsifier for use in synthetic rubber production. DMA is used directly as a modifier in the vapor phase polymerization of butadiene and as a stabilizer for natural rubber latex (instead of using ammonia).
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Solvents
(Mono- and Dimethylamine)
Solvents are the biggest use for dimethylamine (DMA) and a growing use for monomethylamine (MMA). They are used to make the polar, aprotic solvents dimethylformamide (DMF), dimethylacetamide (DMAc), and n-methylpyrrolidone
(NMP).
DMF is made from the reaction of DMA and carbon monoxide or methyl formate. Its uses include urethane coatings, spinning solvent (primarily for acrylics), reaction solvent, extraction solvent (such as butadiene extraction), and processing solvent (including solvent for dicyandiamide for epoxy-laminated printed circuit boards).
DMAC is made from the reaction of DMA and acetic acid or acetic anhydride. It is also used as a spinning solvent and reaction solvent as well as for the manufacture of dyes, pharmaceuticals, and vinyl polymers.
NMP uses MMA reacted with gammabutyrolactone. Its varied uses include reaction solvent (engineering resins), extraction solvent (lube oil refining), spinning solvent, paint stripper (replacing methylene chloride), electronics (for strippers and cleaners), and enamel coatings (magnet wire with polyamide/imide resins).
MMA is also used for extractive distillation of butylene and butadiene by forming an azeotrope with butylene. DMA can be reacted with phosphorous trichloride in the presence of trimethylamine to make tris-(dimethylamido)-phospate. This has been used to dissolve polyacrylonitrile, as a solvent for polyvinylidene chloride, and as a selective solvent for acetylene.
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Surfactants
(Dimethylamine)
Surfactants are used in the manufacture of soaps, shampoos, detergents, and other specialty wetting applications. Dimethylamine is reacted with fatty tertiary amines with C10-C18 alkyl groups from alpha-olefins or fatty alcohols to make nonionic alkyldimethylamines. Salts of n-acyl-n-methyltaurates and n-acyl sarcosinates are used in many specialty surfactants. DMDAC (see Water Treatment), made from DMA, is used in shampoos.
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Water Treatment
(Dimethylamine)
Dimethylamine is used as a raw material to produce agents that remove suspended solids for water clarification in industrial and municipal raw, potable, and wastewater treatment plants. They are used to improve solid/liquid separation in sedimentation, filtration, and flotation operations.
Polyelectrolytic cationic flocculants made from DMA, such as dimethyldiallylammonium chloride (DMDAC) or epichlorohydrindimethylamine, are homopolymerized or copolymerized with acrylamide. Also, DMA can be reacted with formaldehyde and polyacrylamide to make Mannich polymers. These polymers can be quarternized with dimethyl sulfate or methyl chloride to improve their performance at high pHs. Dimethylaminoethanol (DMAE) methacrylate-acrylamide copolymers are also used as cationic flocculants.
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Other Uses
(Mono-, Di-, and Trimethylamine)
Methylamines are used to make many other intermediates covering a myriad of applications. DMAE (see Water Treatment) is used for water-based surface coatings as a dispersant and pH control agent. It is also used as a viscosity index improver for lube oils. MMA is used to make cyclic polyimides. DMAE and DMAPA (see Personal Care) are used for corrosion inhibitors in boiler feed water and return condensate steam systems.
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