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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.
Please
forward this PTC Tip of the Month to your colleagues and encourage them
to
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PTC
Seminar via Telephone & PowerPoint - October
1, 2003
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 [1] fluorene derivatives are not very
acidic, [2] the carbanion from the monobutyl fluorene derivative is sterically
hindered and [3] 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
Challenge -
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.
Phase-Transfer
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.
Conferences
- 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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Before
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.
Policy
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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