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Tip of the Month
Avoid Overdrying PTC Reactions
US Patent 6,790,981 (Mueller et al. 14-Sep-2004) is a compelling example which notes that even when working with water-sensitive compounds in PTC systems, it is important to avoid overdrying when screening for optimal conditions. In this application, the inventors reacted sodium phenolsulfonate (SPS) with nonanoyl chloride using diethyleneglycol-dimethylether as the complexant phase-transfer catalyst (likely acts as an open crown ether complexing with the sodium) and Isopar G as solvent. When the system is overdried, a yield of 45% is obtained, whereas a 95% yield is obtained with more optimal drying of "lower quality" SPS! An older but good PTC version of this reaction is shown in the PTC Reaction of the Month below.
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Reaction of the Month
Phenol O-Acylation Using Acid Chloride
This patent describes the PTC O-acylation shown below. The inventors note that PTC enhances the rate of reaction for the preparation of alkanoyloxybenzenesulfonate salts of high purity. In addition, the process uses lower temperatures than for similar non-PTC processes, and "the loadings of acid chloride required to carry out the reaction are lower, which, in combination, renders the process very economical." Dumas, D.; Subramanyam, V. (E. I. Du Pont de Nemours) US Patent 5,069,828, 03-Dec-1991
If you can't see the structures, click HERE
Catalyst of the Month
This inexpensive phase-transfer catalyst works as a complexant and can be extremely effective and useful in applications such as that shown in the PTC Tip of the Month above. This catalyst is inert under most PTC conditions (basic and neutral) and has a boiling point attractive for easy separation and recovery.
It is not always obvious which PTC applications will be catalyzed by glymes. However, it is usually worthwhile to screen these catalyst before setting the process in stone.
Availability, Samples and Quotes
Request samples and quotes from: Clariant (click on link)
Other Phase-Transfer Catalysts:
PTC Supplier Directory: choose from a dozen suppliers & 80 PT catalysts and ask for free samples & quotes.
PTC Communications is considering conducting a 1-hour webinar (seminar over the web) in 2005 on a PTC topic(s) of value to our customers. Your input is required to justify this event or series. A PTC Training survey will be sent to you shortly. In the meantime, feel free to suggest specific PTC topics by contacting Marc Halpern by E-mail or telephone (+1 856-222-1146) or fax (+1 856-222-1124). A sponsor has been identified and will absorb almost 100% of the costs including logistics. In case you may be concerned, the webinar will be technical and not a sales pitch.
PTC Option Go/No-Go Consultation
Provide a quick and cost-effective key decision aid during initial project planning, whether to pursue evaluation of phase-transfer catalysis as an option to achieve success or breakthrough performance for an organic reaction/process, consisting of uniquely qualified expert opinion and supported by 28 years of PTC experience and documented evidence.
Benefit & When To Use
Can be crucial to achieve highly effective R&D for organic chemical reactions/processes during:
PTC Organics will deliver a written confidential "PTC Option Opinion" for a specific organic reaction which will include
To initiate project or obtain attractive pricing for 2005 budget planning, contact Marc Halpern at tel +1 856-222-1146, fax: +1 856-222-1124 or E-mail.
patent attorney (United States) familiar with Phase-Transfer Catalysis,
organic chemistry and biochemistry. Contact Mannie Morgenstern by E-mail
or at telephone 818-788-5531 (California).
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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 information provided here 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 #25 - October 2004
Copyright 2004 PTC Communications, Inc.
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