W. R. Grace Co.

Hampshire Chemical Corp.

W. R. Grace Co.-conn.

Gerald J O'Neill

Charles W Simons

Robert S Holdsworth

Robert J Bulka

Charles A Billings

Albert H Levesque

Joel A Gribens

Paul Tarrant

Felix B Popper

Vincent I DiBiasio

Process for the production of TMEDA in high yield by reducing 2,3-dimethyl-2,3-dinitrobutane with hydrogen in the presence of a chromium promoted Raney cobalt catalyst. A solution of 2,3-dimethyl-2,3-dinitrobutane in a suitable solvent is fed to a reactor while avoiding the accumulation of 2,3-dimethyl-2,3-dinitrobutane in the reaction medium, such as by feeding it at a rate no greater than its rate of reaction with hydrogen. In a preferred embodiment, the resulting TMEDA is recovered by converting it to an amine salt by sparging carbon dioxide through the solution.

Preparation of tetramethylethylenediamine

A method of stabilizing nitriles, and in particular iminodiacetonitrile (IDAN), ethylendiamine-triacetonitrile (EDTN), and especially nitrilotriacetonitrile (NTAN). The present invention also encompasses the resulting stabilized nitrile. The method of the present invention comprises contacting the nitrile with a mixture of silica and alumina, zeolites or glass.

Method of stabilizing nitriles

A process for the purification of bis(difluoromethyl)ether. Bis(difluoromethyl)ether is exposed to molecular sieves in order to reduce or completely remove impurities. In a further embodiment, the present invention optionally includes means for preferentially inhibiting the formation of CF.sub.2 HOCCl.sub.3 in the formation of bis(difluoromethyl)ether prior to exposing the bis(difluoromethyl)ether to the molecular sieves.

Purifications of flourinated dimethyl ethers

The synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein (x+y) is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether in the presence of a solvent to form a chlorinated reaction product of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z wherein z is 1, 2 or 3. The process may also be carried out in the presence of oxygen in order to inhibit the formation of CF.sub.2 HOCCl.sub.3. The resulting compound(s) is then fluorinated with HF before or after separation, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.

Chlorination of difluoromethyl methyl ether

A novel process for synthesizing difluoromethyl methyl ether for use as regrigerants and blowing agents, etc. is hereby disclosed. This process involves (1) feeding chlorodifluoromethane at a rate from about 0.5 to 5 grams of feed gas per gram of solution per minute through a sodium methoxide in methanol or basic ion exchange slurry in methanol; (2) removing the gaseous product and the unreacted chlorodifluoromethane continuously; and (3) separating difluoromethyl ether from the unreacted chlorodifluoromethane.

Synthesis of fluoromethyl ether

The synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein (x+y) is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether in the presence of oxygen to form a chlorinated reaction product of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z wherein z is 1 or 2, and wherein the formation of CF.sub.2 HOCCl.sub.3 is inhibited. The resulting compound(s) is then fluorinated with HF before or after separation, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.

Vapor phase chlorination of difluoromethyl methyl ether

A novel process is disclosed for the synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein the total x+y is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether to form a chlorinated reaction product, including at least one compound of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z, wherein z is 1, 2 or 3, which compound is then fluorinated with HF and/or an antimony salt and with or without separation from the chlorinated reaction product, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.

Synthesis of fluorinated dimethyl ethers

A novel process is disclosed for the synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.X F.sub.Y H.sub.3-(X+Y) wherein X and Y are each independently 0, 1, 2 or 3 and wherein the total X+Y is 2 or 3. The process involves chlorination of methyl difluoromethyl ether to form a chlorinated reaction product, including at least one compound of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z, wherein z is 1, 2 or 3, which compound is then fluorinated, with or without separation from the chlorinated reaction product, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.

Polyamines are prepared via the batchwise hydrogenation of polynitriles by the gradual addition of the polynitrile into a fed-batch reactor which contains chromium promoted Raney.RTM. cobalt catalyst. The hydrogenation optionally is conducted in the presence of anhydrous ammonia. The polyamine product having amino groups which corresponds to the nitrile of the polynitrile is economically obtained in high selectivity and yield as the dominant product.

Preparation of polyamines

A chlorine-free refrigerant comprised of bis (difluoromethyl)ether; CHF.sub.2 OCHF.sub.2. The refrigerant may be used alone or in combination with other refrigerants. The bis (difluoromethyl) ether refrigerant is environmentally safe, non toxic, non flammable and has the desired physical, chemical and thermodynamic properties necessary for a refrigerant.

Bis (difluoromethyl) ether refrigerant

Certain fluorinated dimethyl ethers have been found to possess the stability, the compatibility and sufficient freedom from deleterious physiological effects to be used as aerosol propellants in cosmetic, hygienic, pharmaceutical and other personal products. Bis(difluoromethyl) ether is also free of the chlorine atoms believed responsible for some destruction of ozone in the upper atmosphere. Bis(difluoromethyl) ether and carbon dioxide provides a combined gaseous and liquefied propellant system having improved aerosol pattern and emptying characteristics and eliminates the compressed gas effect usually shown by use of carbon dioxide in propellant systems.

Aerosol propellant for personal products

Methyl trifluorovinyl ether can be stabilized with respect to liquid and vapor phase deflagration or explosive potential by the addition of certain fluorohaloalkanes to the methyl trifluorovinyl ether.

Stabilization of methyl trifluorovinyl ether

Certain fluorinated dimethyl ethers have been found to possess the stability, the compatibility and sufficient freedom from deleterious physiological effects to be used as aerosol propellants in cosmetic, hygenic, pharmaceutical and other personal products. These compounds, bis(difluoromethyl) ether and perfluorodimethyl ether, are also free of the chlorine atoms believed responsible for some destruction of ozone in the upper atmosphere.

New aerosol propellants for personal products

The following halocyclopropyl halomethyl ethers have been synthesized and found to possess utility as general inhalation anesthetics: 1-chloro-2-chlorofluoromethoxy-1,2,3,3-tetrafluorocyclopropane, 1-chloro-2-difluoromethoxy-1,2,3,3-tetrafluorocyclopropane, 1-bromo-2-chlorofluoromethoxy-1,2,3,3-tetrafluorocyclopropane and 1-bromo-2-difluoromethoxy-1,2,3,3-tetrafluorocyclopropane.

Halocyclopropyl halomethyl ethers

The following chlorocyclopropanes have been found to possess utility as general inhalation anesthetics: 1,1-dichloro-2-methyl-2,3,3-trifluorocyclopropane, 1,2-dichloro-1-fluoro-2-methylcyclopropane, 1,1,2-trichloro-2,3,3-trifluorocyclopropane, 1,1-dichloro-2-trifluoromethyl-2,3,3-trifluorocyclopropane, 1,2-dichloro-1,2,3,3-tetrafluorocyclopropane, 1,1,2,2-tetrachloro-3,3-difluorocyclopropane and 1,1-dichloro-2,3,3-trifluorocyclopropane.

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Arlington, MA, United States of America

Gerald J O'Neill