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PTC Tip of the Month - Extremely Short PTC Reactions Using Microwave
What happens when you combine PTC with high molecular kinetic energy using microwave? You get VERY FAST reactions. For example, let's compare two solvent-free solid-liquid PTC esterifications of acetate. The classical PTC patent of all time (US 3,992,432) describes standard PTC for 100% yield of decyl acetate from sodium acetate and decyl bromide in 1hour at 105oC using 10 mole% Aliquat 336. In contrast, using microwave, a similar reaction (shown below) is over in 90 seconds ! Bram, G.; Loupy, A.; Majdoub, M.; Synth. Comm., 1990, 20, 125. A very recent PTC/microwave ring opening with HBr took 5 min (no reaction without PTC). Kad, G.; Kaur, I.; Bahndari, M.; Singh, J.; Kaur, J. Org. Res. Process Dev., 2003 7, 339.
Even though commodity chemicals may not be made using PTC/microwave, you may be surprised to calculate how much specialty organic chemical may be able to be produced in a continuous PTC/microwave reactor with a 90-second residence time, considering that multi-liter microwave reactor systems are commercial.
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Seminar via Telephone & PowerPoint - October
Marc Halpern of PTC Organics will conduct the PTC tele-seminar entitled "Reducing Cost of Manufacture of Organic Chemicals Using Phase-Transfer Catalysis" on October 1, 2003 at 09:00 US eastern standard time. The seminar will be conducted by telephone with a PowerPoint presentation (to be sent prior to the seminar) and can be accessed from anywhere in the world. Register by contacting Marc Halpern at tel 856-222-1146 (US) or by E-mail to receive your passcode, telephone number to call and other instructions for participation.
Registration is free before September 1, 2003 (or $295 thereafter) and is limited to one access point per site. It is highly recommended that you use a speakerphone and projector connected to your computer for effective participation of multiple participants. A total of 20 access points will be available (one is reserved for the PTC Organics' speaker). Preference will be given to multi-participant access points. PTC Organics reserves the right to determine the participating companies which will be selected from the industrial customers or potential industrial customers of PTC Organics.
PTC Reaction of the Month - C-Alkylation
of Low Acidity C-H Groups
PTC excels in nucleophilic C-alkylation but also excels in dehydrohalogenation of alkyl halides. Which wins? Even though  fluorene derivatives are not very acidic,  the carbanion from the monobutyl fluorene derivative is sterically hindered and  butyl bromide can undergo dehydrobromination, PTC can still be used to achieve high yield as shown in the figure. Woo, E.; Shiang, W.; Inbasekaran, M.; Roof, G.; (Dow Global Technologies) 2003 US Patent 6,593,450
Can PTC Improve Your Process?
If you answer "Yes" to any one of the following questions and your reaction is one of > 35 categories on this list, then Phase-Transfer Catalysis may help you achieve significant process improvement. We will send you a gift of appreciation, the CD-ROM "The Best of Industrial Phase-Transfer Catalysis," if you inquire about any of the process improvements shown below for your company (DO NOT DISCLOSE PROPRIETARY SPECIFIC REACTION INFORMATION WITHOUT A SECRECY AGREEMENT) - see instructions and conditions below.
Increase Yield: Could a 5-10% yield increase significantly increase profit (e.g., is your current yield < 88%)?
Reduce Cycle Time: Does your current process take > 8 hours? Want to eliminate isolation of intermediates?
Replace Strong Base with NaOH: Are you using alkoxides (e.g., methylate, t-butoxide), Na hydride, Na amide?
Improve Selectivity: Do you need to improve product assay or simplify workup? Too much hydrolysis?
Reduce Excess Reactants: Are you using > 10% excess of any expensive and/or hazardous reactant?
Replace Solvent for Easier Workup: Are you using DMSO, NMP, DMF, DMAC or undesirable solvent?
Increase Reactor Volume Efficiency: Does solvent and/or water take up > 50% of your reactor volume?
Other Challenges: Too much waste? Working with water-sensitive compounds? Any other challenges?
To send your non-proprietary inquiry, contact Marc Halpern at PTC Organics by E-mail, website, telephone (+1 856-222-1146) or fax (+1 856-222-1124). To receive "The Best of Industrial Phase-Transfer Catalysis" CD-ROM, your inquiry must be from an industrial company in North America, Europe or Japan. Offer valid while quantities last (100 as of August 2003). PTC Organics reserves the right to distribute "The Best of Industrial Phase-Transfer Catalysis" to selected industrial chemists, engineers and managers. DO NOT DISCLOSE PROPRIETARY SPECIFIC REACTION INFORMATION WITHOUT A SECRECY AGREEMENT.
PTC Organics offers PTC Breakthrough Process Screening for rapid and highly effective evaluation of breakthrough phase-transfer catalysis processes. As the world leader in industrial phase-transfer catalysis, PTC Organics develops breakthrough high-performance low-cost PTC processes.
Catalysts - Samples
Find suppliers for > 80 phase-transfer catalysts at the Phase-Transfer Catalyst Supplier Directory. Full contact information & websites for multiple suppliers for N-quats, P-quats, PEG's, crowns, chiral PTC, hi-temp PTC's, ionic liquids, resins.
- Meet PTC Organics
Informex Corporate Excellence Conference - September 15-16, 2003 in Cambridge, Maryland, USA
CPhI - October 27-29, 2003 in Frankfurt, Germany
Informex 2004 - January 19-22, 2004 in Las Vegas, Nevada, USA
PTC Organics is a member of SOCMA
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performing any PTC reactions read this important message
Organic chemical reactions are inherently dangerous. Moreover, phase-transfer catalysis may provide rate and other enhancements which can intensify associated hazards. Under no circumstances should anyone perform any procedure on any scale based in whole or in part on any of the contents of this E-mail before thoroughly establishing safe operating procedures and performing a full and competent hazardous operations analysis with the participation of qualified technical personal trained in chemical, engineering, safety, industrial hygiene and environmental disciplines and sciences.
The list of PTC Tip of the Month subscribers will not be sold, rented or transferred and will be used only by PTC Communications, Inc. and PTC Organics, Inc. to provide information related to Phase-Transfer Catalysis. PTC Communications, Inc. reserves the right to distribute the PTC Tip of the Month to selected industrial chemists, engineers and managers.
PTC Tip of the Month #11 - August 2003
Copyright 2003 PTC Communications, Inc.
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