Aliquat 336 (registered trademark of BASF) is a mixture of 4 quat salts, described at http://phasetransfer.com/WhatisAliquat336andAdogen464.pdf, of which 33% is methyl trioctyl ammonium chloride. Aliquat 336 has been reported to enhance the activity of palladium catalysts for Suzuki and other reactions, for more than 20 years.
The point of this PTC Tip of the Month is that if you are using a palladium catalyst for Suzuki coupling or other reactions, you should probably screen Aliquat 336 (after first making sure that the reaction can be done safely such as by running a DSC first to assure no uncontrollable exotherms) to determine if you can achieve advantage using this phase-transfer catalyst. Advantages may be in reaction performance such as control of molecular weight, advantageous reaction conditions, using a less expensive form of palladium (choice of ligands) or even using less of the expensive palladium catalyst.
To illustrate the use of Aliquat 336 in Pd catalyzed PTC reactions, following is a sampling of US Patents that have used the Aliquat 336-Pd combination over the past year.
US Patent 10,403,822 (Sep 2019): Synthesis of thienothiophene isoindigo-based polymer semiconductors
US Patent 10,392,395 (Aug 2019): Synthesis of 4,7-bis-(2-bromo-4-methylpyridin-6-yl)-2,1,3-benzothiadiazole
US Patent 10,364,316 (Jul 2019): Synthesis of 2,5-diphenyl p-xylene
US Patent 10,340,457 (Jul 2019): Synthesis of dithiopentalenes
US Patent 10,290,809 (May 2019): Synthesis of polymer between dithiofluorene and thiobenzimidazole and US Patent 10,059,796 (Aug 2018)
US Patent 10,276,799 (Apr 2019): Synthesis of Iridium phenyl-isoquinoline phenyl-triazole compounds
US Patent 10,273,329 (Apr 2019): Synthesis of carbazole-divinylbenzene copolymers
US Patent 10,199,577 (Feb 2019): Synthesis of triphenyl derivatives and US Patent 10,134,988 (Nov 2018)
US Patent 10,158,079 (Dec 2018): Synthesis of polymers of benzodithiophene
US Patent 10,005,886 (2018): Synthesis of dimethyl 2,2”,4,4”,6,6”-hexamethyl-p-terphenyl-3,3”-diester
If you want to achieve high-performance low-cost PTC processes with efficient utilization of constrained R&D resources, now contact Marc Halpern of PTC Organics to integrate the highly specialized expertise of PTC Organics in industrial phase-transfer catalysis with your company’s commercial goals.
