of the Month - q-value
and C# for Catalyst Structure-Activity
The "q-value" and "C#" are two empirical parameters which are used to characterize the structure of quaternary ammonium salts for structure-activity relationships. C# is simply the total number of carbons on the 4 alkyl chains. Thus, the C# for methyl tributyl ammonium is 1 + 4 + 4 + 4 = 13. As the C# increases, the organophilicity increases and usually results in a higher concentration of the quat-anion pair in the organic phase. When the rate determining step is the organic phase reaction ("I-Reaction"), C#'s in the range of 16 to 32 often provide desirable reactivity. The "q-value" parameter is often useful when the rate determining step is mass transfer ("T-reaction"), especially when using hydrophilic anions such as hydroxide (about half of PTC applications fall in this category). The q-value is calculated by adding the reciprocals of the number of carbons on each of the four chains of the quat. Thus, the q-value for methyl tributyl ammonium is 1/1 + 1/4 + 1/4 + 1/4 = 1.75. For T-reactions, quats with q-values in the range of 1 to 2 often promote desirable reactivity, with q-values of 1.5 to 1.75 often being the best. For more information, please contact Marc Halpern at tel +1 856-222-1146 or by E-mail.
Please forward this PTC Tip of the Month to your colleagues and encourage them to subscribe
Consulting - Stop Wasting
Precious R&D Resources & Improve Performance
What if you could achieve PTC breakthrough processes in your lab in weeks instead of months (if at all)? PTC Organics' dedicated industrial phase-transfer catalysis experts have provided highly specialized PTC consulting and other PTC services at 189 sites in the US, Europe and Japan and have helped companies save > $150 million and improve overall R&D effectiveness.
To improve route selection, process improvement, process development and overall reaction performance, contact Marc Halpern at tel +1 856-222-1146 or by E-mail.
Training - Plan
your training budget - November
2004 and May 2005 in Chicago and Newark
The course "Practical Phase-Transfer Catalysis" will be conducted in Chicago and Newark later in 2004 and 2005. Can't come to the course? Soon you will be able to purchase just the manual or the manual with a transcript of the course. "Practical Phase-Transfer Catalysis" can also be conducted at your company anytime (North America, Europe or Japan) as a private in-house course. More than 530 chemists, engineers and managers at nearly 100 companies have participated in this highly rated course from 1996 to 2004. Click here for details and agenda or contact us by E-mail or telephone (+1 856-222-1146) or fax (+1 856-222-1124).
Inexpensive 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).
Reaction of the Month - Secondary
Alcohol to Secondary Alkyl Chloride
It can be challenging to convert secondary alcohols to secondary alkyl chlorides in high purity and avoiding the use of thionyl chloride with stoichiometric pyridine. This patent uses tetrabutyl ammonium chloride to significantly reduce the reaction time (36 h to 8 h) in the selective reaction of secondary alcohols with cyanuric chloride, e.g., to form 6-undecyl chloride. At 99% conversion of 6-undecyl alcohol, the key byproducts are undecene (20%) and diundecyl ether (4%). Extremely low isomerization is observed. Neumann, M.; Osterholt, C. (Degussa) US Patent 6,756,513 29-June-2004
Catalyst of the Month - Tetrapropyl
Usually works well in T-reactions due to q-value of 1.33. Easier to extract into water than TBAB (less residual catalyst in product while generating less aqueous waste). Usually much more stable than quats with ethyl groups in the presence of NaOH. Also used as a template for zeolites.
Usually less reactive than TBAB in I-Reactions due to lower C#.
q-value = 1.33; C# = 12
Availability, Samples and Quotes from Competitors
Request samples and quotes from:
Delta Finochem, Dishman Pharmaceuticals & Chemicals, GFS Chemicals, Lion Akzo, Nehachem, SACHEM, Tatva Chintan (click on link)
Other Phase-Transfer Catalysts:
PTC Supplier Directory: choose from a dozen suppliers & 80 PT catalysts and ask for free samples & quotes.
Technology for Licensing
For details, contact Marc Halpern at tel +1 856-222-1146 or by E-mail.
Pharma - for PTC options during route selection, contact Marc Halpern by E-mail, website or telephone (+1 856-222-1146).
To stop receiving the "PTC Tip of the Month," contact us by E-mail at email@example.com or by telephone at +1 856-222-1146.
To receive the "PTC Tip of the Month," contact us at www.ptcorganics.com/ContactUs.htm and note "Subscribe to Tip" in the Comments or by telephone at +1 856-222-1146.
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 #22 - July 2004
Copyright 2004 PTC Communications, Inc.
Go to PTC Tip of the Month index