The synthesis of butene glycol ethers with aluminium triflate
Bibliographic record
Abstract
The use of aluminium triflate as a ring-opening catalyst for butene oxide (BuO) was evaluated in the presence of different alcohols such as methanol, ethanol, n-propanol, n-butanol, 2-propanol, 2-methyl-1-propanol, and 2-methyl-2-propanol. The reaction with methanol was studied kinetically by varying the temperature, catalyst concentration, and methanol butene oxide molar ratio. These reactions yielded two major products (2-methoxy-1-butanol and 1-methoxy-2-butanol) in a approximate ratio of 1:1. It was noted that at low catalyst concentrations (<5 ppm), low temperatures (<90 °C), and a MeOHBuO molar ratio of 8:1, the selectivity of the reaction could be kinetically manipulated to shift the product ratio towards 1-methoxy-2-butanol, the α-alkoxyalcohol. This result was confirmed by an experimental design program. Statistical calculations using the data from the experimental design identified a feasible region in which reactions with methanol could be carried out, which would lead to slightly higher selectivities to 1-methoxy-2-butanol. This region shows that the methanol butene oxide ratio should be 8:1, the temperature between 80 and 85 °C, and the catalyst concentration between 3.9 and 5 ppm. These reaction conditions were used to carry out a test reaction with methanol and an extended series of alcohols. All the alcohols, except for 2-methyl-2-propanol, reacted with butene oxide under these conditions, with the selectivity to the α-alkoxyalcohol higher than to the β-alkoxyalcohol. To obtain a ring-opening reaction with 2-methyl-2-propanol, it was found that a higher catalyst concentration (approximately 10 ppm) and a lower alcohol butene oxide ratio (6:1) at a temperature of 80 °C were necessary. This reaction led to a mixture of 1-tert-butoxy-2-butanol and 2-tert-butoxy-1-butanol with the selectivity to the α-alkoxyalcohol being somewhat higher because of the steric influence of the bulky tert-butoxy group.Key words: aluminium triflate, alcohols, butene oxide, ring opening, α-alkoxyalcohol, β-alkoxyalcohol.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".