Ring opening of epoxidized methyl oleate using a novel acid-functionalized iron nanoparticle catalyst
Bibliographic record
Abstract
Hydroxyl soybean oils, also called soy polyols, are biobased chemicals designed to replace petroleum-based polyols mainly for polyurethane (PU) applications. Soy polyols are obtained by acid-catalyzed ring opening of expoxidized soybean oils or other epoxidized plant oils by nucleophilic SN2 attack of methanol. Recyclable heterogeneous catalysts are preferred for the ring-opening reactions over non-recyclable homogeneous catalysts because they minimize environmental impact. The drawbacks of current solid catalysts such as SAC 13 and Amberlite 15 are low production yield and high energy consumption. Here, we demonstrate a greener synthetic pathway of soy polyols with low energy consumption and excellent atom economy and environment (E) factor by using novel sulfamic acid-functionalized iron (iron/iron oxide core shell) nanoparticles (NPs) as a heterogeneous catalyst. The excellent selectivity of the reaction with the recyclable NPs was confirmed by 1H NMR, 1H-1H COSY NMR, and ESI-MS comparable to non-recyclable H2SO4. The synthetic route with the NPs resulted in higher product yield (almost 100%) as H2SO4 at room temperature for 30 min over the SAC 13 (83% yield at 60 °C for 60 min) and Amberlite 15 (87% yield at 60 °C for 100 min). Life cycle assessment (LCA) revealed that the NP synthetic technology for soy polyol production is superior or equal to the competing routes (H2SO4, SAC 13, and Amberlite 15 methods) with respect to 9 environmental impacts (acidification potential, ozone depletion potential, smog formation potential, global warming potential, human toxicity by ingestion, human toxicity by inhalation, persistence, bioaccumulation, and abiotic resource depletion potential).
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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".