Contents: PTC Tip of the Month, PT Catalyst of the Month, PTC Reaction of the Month, Challenge, Subscribe/Unsubscribe
PTC Tip
of the Month - Guideline
for Using Water-Sensitive Reactants with PTC
Compounds such as PCl3 and CH3SO2Cl ("MSC";
see PTC Reaction of the Month below) are very water sensitive but
surprisingly can be used very
successfully in PTC systems. Unfortunately, often PTC is not even considered (by
non-PTC experts) for
such very water-sensitive reactants due to the obvious potential for hydrolysis.
PTC Organics has developed highly effective PTC reactions of water-sensitive
reactants and we would like to share the following simple guideline. If your reactant
candidate is more stable than MSC at room temperature based on the decomposition curve and
conditions shown below (i.e., in the green region of the graph; one data point is
enough), then expert choice of PTC reaction conditions may deliver impressively high performance.
Contact
PTC Organics about your challenging water-sensitive
applications.
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PT
Catalyst of the Month - Methyl
Tributyl Ammonium Chloride
Advantages
Very high reactivity for PTC T-Reactions with high ionic strength (often 3-10X
vs TBAB); extremely easy separation by extraction into water (often 100-1000X vs
TBAB) greatly minimizing aqueous waste generation; lower cost than TBAB (both
per kg and per mole); overall excellent replacement for TBAB in ~20% of existing
commercial TBAB applications.
Disadvantages
Often low reactivity for PTC I-Reactions with dilute aqueous phase; slightly
less thermally stable than TBAB in the presence of strong base.
Reactivity
Parameters (Contact
PTC Organics for explanation)
Organophilicity
C# = 13; Accessibility q-value = 1.75
Availability, Samples and Competitive Quotes
Available as a 75% aqueous solution (standard) or 98% solid (more expensive).
Request samples and quotes from: Cognis,
Dishman,
Nehachem,
Rutherford,
Sachem
PTC Reaction of the Month - Reaction
of Methanesulfonyl Chloride
To reinforce the guideline for using water-sensitive compounds with PTC
described in this month's "Tip," we share with you
results of a PTC reaction (not commercial) developed in PTC Organics' lab.
Catalysts, solvents and inexpensive inorganic
bases screened are common and commercially available materials.
Challenge -
Production Costs Too High?
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:
Competing with China and India? Too much waste? Working with water-sensitive
compounds?
If you answered "Yes" to even one question above and your
reaction type is one of 35 on the
PTC Reaction
list, then Phase-Transfer Catalysis may help you achieve BREAKTHROUGH process
improvement and improve profit margin (competing with China & India?).
INQUIRY & GIFT
OF APPRECIATION: Contact Marc
Halpern at PTC Organics by E-mail,
website, telephone (+1
856-222-1146) or fax (+1 856-222-1124) to inquire about using PTC to improve
process performance. If your inquiry is for an active commercial process at your
industrial
company in North America, Europe or Japan then we will send you a GIFT
OF APPRECIATION, the CD-ROM
"The Best of Industrial Phase-Transfer Catalysis" (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.
As the world leader in industrial
phase-transfer catalysis, PTC Organics offers PTC
Breakthrough Process Screening for rapid and highly effective evaluation of
breakthrough high-performance low-cost phase-transfer catalysis processes.
PTC
Seminar via Telephone & PowerPoint
PTC Organics is offering to selected
qualified companies a private session of the PTC tele-seminar entitled "Reducing Cost of Manufacture of Organic
Chemicals Using Phase-Transfer Catalysis." If your company qualifies, 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.
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.
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 #12 - September 2003
Copyright 2003 PTC Communications, Inc.
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