Formic Acid → Triethylazanium;formate

To a solution of triethylamine (33.05 g, 326.7 mmol) in toluene (150 mL) was added 96 percent formic acid (13.81 g, 300.1 mmol) slowly over 5 min. The two-phase system was stirred overnight (17 hr) at ambient temperature. The toluene was removed by distillation (maximum bath temperature 120° C., overhead temperature kept above 100° C.) over several hr. The remaining oil was transferred to a graduated cylinder and the contents sparged with a flow of nitrogen until no noticeable odor of toluene remained. The pale yellow triethylammonium formate (25.35 g, 172.2 mmol, 57.4 percent yield) was diluted to 172.2 mL with acetonitrile giving a 1.0 molar solution. The contents were stored in a serum-capped storage bottle under nitrogen. This or similarly prepared material was used in the following examples whenever preformed triethylammonium formate was called for.

1. customThe toluene was removed by distillation (maximum bath temperature 120° C., overhead temperature kept above 100° C.) over several hr
2. customthe contents sparged with a flow of nitrogen until no noticeable odor of toluene

ORD record

ord-a2abaadbec51448ab12e2a2383299a22

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05089653