Upgrading bio-based acetone to diacetone alcohol by aldol reaction using Amberlyst A26-OH as catalyst

Abstract

The aldol reaction of bio acetone in presence of a strongly basic ion exchange resin was carried out with and without the addition of water in a temperature range between − 30 °C and 45 °C. The conversion, selectivity and service time of the ion exchange resins were investigated in a stirred batch reactor and a continuous fixed bed reactor. For the batch experiments, both conversion and selectivity increased with decreasing temperature. Furthermore, the addition of water to the reaction medium has a positive effect on selectivity and catalyst service time of the resins. For the continuous flow experiments carried out in a fixed bed reactor, the selectivity towards diacetone alcohol is higher than in a batch reactor. This high selectivity is favored by a short contact time which inhibits as expected most of the consecutive reactions.

The Production of Isophorone

“…To alternatively produce renewable products from isophorone, bio-based acetone is used for the manufacturing of Encyclopedia 2023, 3 227 isophorone [1]. The production of bio-based acetone is carried out through fermentation, e.g., the acetone-butanol-ethanol (ABE) fermentation [97][98][99][100].…”

“…The acetone condensation has a complex reaction mechanism with multiple possible reaction products, including mesityl oxide, phorone, mesitylene, isoxylitones, and ketonic resins [5,99,[109][110][111][112]. In 1989, Salvapati et al described the three-step reaction mechanism of acetone to isophorone shown in Figure 2 as the most likely reaction mechanism for the formation of isophorone [5].…”

“…Based on the published literature, the reaction network shown in Figure 3 is proposed, excluding the formation of higher condensation products such as polymers [110,124,125] or oligomers of acetone and isophorone [4,111,[126][127][128][129][130][131]. The reaction starts with acetone (1), which forms diacetone alcohol (4) through aldol reaction [5,99,132,133]. From diacetone alcohol (4), mesityl oxide (3) and iso-mesityl oxide (2) are formed via dehydration [5,99,[134][135][136].…”

“…The reaction starts with acetone (1), which forms diacetone alcohol (4) through aldol reaction [5,99,132,133]. From diacetone alcohol (4), mesityl oxide (3) and iso-mesityl oxide (2) are formed via dehydration [5,99,[134][135][136]. The aldol reaction of diacetone alcohol (4) and acetone yields triacetone dialcohol (9) [5,99,132,137].…”

“…From diacetone alcohol (4), mesityl oxide (3) and iso-mesityl oxide (2) are formed via dehydration [5,99,[134][135][136]. The aldol reaction of diacetone alcohol (4) and acetone yields triacetone dialcohol (9) [5,99,132,137]. Triacetone dialcohol (9) mostly reverts to acetone (1) but can also form semiphorone (8) or 2,2,6,6-tetramethylpyron-4-one ( 14) through dehydration [137][138][139].…”