Halocarbon

Fluorine Innovator Halocarbon Products Corporation Advances Capabilities with Grignard Reactions

February 15, 2006 - Orlando, FL - Halocarbon Products Corp., the award-winning global pioneer in specialty fluorochemicals production, has added Grignard reactions to its capabilities. The Grignard Reaction is a powerful tool to make advanced fluorinated intermediates for pharmaceuticals and agricultural chemicals and specialty fluorinated monomers useful to the semiconductor industry. Several compounds are now actively being developed.

"The use of the Grignard Reaction allows us to make more sophisticated fluorinated building blocks from our existing products," said Peter Murin, Chief Executive Officer, Halocarbon Products Corporation. "We’ve been asked to supply several molecules that are most efficiently made via this reaction and are seeing interest in other compounds."

A Grignard reaction is the addition of an organomagnesium halide (Grignard reagent) to a carbonyl compound to form an alcohol. More generally, Grignard reagents enable the formation of carbon-carbon bonds with a large number of functional groups, typically without the addition of heat or catalysts. This approach is particularly useful when a strong carbon nucleophile is needed.

Grignard reagents are air- and moisture-sensitive species that react violently with many compounds. Formation of the reagent itself is often even more hazardous, and some fluorinated species are unstable under these conditions. Grignard reagents and reactions typically use highly flammable solvents. "Doing such reactions on a small scale in a laboratory demands great care and attention. On an industrial scale, the skills required are considerable," noted Barry Jones, Technical Director, Halocarbon Products.

"Halocarbon has the resources and core expertise in fluorine chemistry to use Grignard reagents from lab scale to multi-ton production in a rapid, efficient manner since our chemistry and chemical engineering are so well coordinated through the development process," continued Jones. "We routinely produce fluorinated molecules that are often used in Grignard reactions. We can produce the fluorinated starting materials in any quantity needed and can do additional fluorination after the Grignard reaction, if necessary."

More Halocarbon innovations
Halocarbon continues its development of novel compounds, notably trifluoroacetone and its corresponding bromide, trifluorobromoacetone. Trifluorobromoacetone can serve as an electrophile at both carbons, as well as being used as a nucleophile. This versatility has made it useful in the synthesis of a variety of biologically active molecules including fungicides, anti-inflammatory drugs and hormone therapies.

Halocarbon has also increased its production of trifluoroacetaldehyde, an unstable gas that, due to its high degree of fluorination, is a very reactive electrophilic agent. It can be used to form alpha-trifluoromethylated alcohols that are useful in the production of pharmaceutical and agricultural chemicals, and as a building block in the synthesis of a variety of fluorinated molecules. Commercially, trifluoroacetaldehyde is often converted to the more easily handled methyl- or ethyl-hemiacetal. These compounds are much more stable liquids that have been used in the synthesis of biologically active molecules that are used as antifungals, antitumor drugs and chemotherapeutic agents.

Trifluoroethylamine, another specialty intermediate available in commercial quantities from Halocarbon, is a weakly basic/nucleophilic amine that has been used to generate many commercially useful compounds. It is used in the synthesis of many drugs and agricultural chemicals, and has been used industrially to make polymerization catalysts and mordants for ink-jet printing. Halocarbon also produces the related trifluoroacetamides, including trifluoroacetamide itself, as well as N-alkylated analogues. Among other applications, these compounds are used to make a variety of neutral silylating agents and as peroxide activators.

About Halocarbon
With headquarters in River Edge, New Jersey, and a state-of-the-art manufacturing plant in North Augusta, South Carolina, USA, Halocarbon is one of the world’s leading producers of specialty fluorochemicals. Halocarbon products include inert lubricants, aliphatic fluorochemicals for pharmaceutical and agricultural chemical manufacturing, inhalation anesthetics and other specialty products. For more information, please contact the company at +1-201-262-8899 or at www.halocarbon.com.