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Record W4406363437 · doi:10.1016/j.cattod.2025.115202

Scaled up epoxidation of terpenes in microemulsion

2025· article· en· W4406363437 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueCatalysis Today · 2025
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Cycloaddition Reactions
Canadian institutionsUniversité Laval
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsTerpeneMicroemulsionCatalysisChemistryOrganic chemistryCombinatorial chemistryBiochemistryPulmonary surfactant

Abstract

fetched live from OpenAlex

The dioxirane epoxidation was traditionally carried out in a two-phase medium: an organic solvent to dilute the olefin to be epoxidised and an aqueous medium in which the peroxymonosulphate oxidant is dissolved. This phase incompatibility generally requires a large quantity of oxidant and oxygen yield does not exceed 25 %. Despite the major advantages of this technique, it is still only used at laboratory scale. The aim of this study is to illustrate a dioxirane epoxidation ability to produce terpene epoxides at the scale of hundreds of milliliters. The technique employs an acetone catalyst that reacts with oxone® to in-situ form dimethyldioxirane, which epoxidizes the terpene. Oxone® is an aqueous oxidant. To remedy its incompatibility with hydrophobic terpene the use of a surfactant at concentration above its critical micelle concentration (cmc) enabled the terpene to be highly dispersed in the aqueous medium in absence of any additional organic solvent by forming a microemulsion, thus improving interface reaction rate and reducing oxygen loss. At 25°C and for a t r of 90 min, several hundred milliliters of limonene, α-pinene, β-pinene, α-terpinene, γ-terpinene, β-myrcene and farnesene were easily epoxidized with both conversion and selectivity of almost 100 %. Oxygen yields of up to 80 % were achieved, against 29 % in absence of microemulsion. The high selectivity of epoxides, the solvent-free aqueous reaction, the ambient conditions, the simple acetone used as catalyst and the easy separation of epoxides from the aqueous medium make this innovative process more appropriate for easy scale-up. • Terpene epoxidation in microemulsion scaled up to hundreds of milliliters. • Epoxidation of limonene, pinenes, terpinenes, myrcene and farnesene. • High yield of oxygen use maintained upon scaling up • CTAHS surfactant confirmed as appropriate. • Epoxidation by dioxirane in aqueous medium whitout organic solvent.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.011
Threshold uncertainty score0.999

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0020.000

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.

Opus teacher head0.004
GPT teacher head0.241
Teacher spread0.236 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it