Acylation of unprotected lactose with 1,18‐octadec‐9‐enedioyl chloride for the synthesis of monocatenary and bolaform agro‐based surfactants
Bibliographic record
Abstract
Abstract Agro‐based surfactants have one of two hydrophilic or hydrophobic parts of vegetable origin. They can be produced from renewable and readily available resources. Carbohydrate fatty acid esters are non‐toxic, non‐ionic, and biodegradable agro‐based surfactants with applications in the pharmaceutical, cosmetic, and food industries. In this work, the chemical synthesis of agro‐based surfactants through lactose acylation with 1,18‐octadec‐9‐enedioyl chloride (Acyl‐Cl) was investigated at room temperature. The acylation reaction proved to be regioselective to the primary hydroxyl group of the glucose‐moiety in the lactose molecule and was promoted by an excess of lactose to produce higher substituted derivatives. Acyl‐Cl conversion was ∼98 % after 1 h of reaction. The production of monocatenary agro‐based surfactant, mono‐lactose 1,18‐octadec‐9‐enoate, was favoured with a molar ratio lactose/Acyl‐Cl of 1 achieving a yield of 48 % after 20 min. Moreover, production of bolaform agro‐based surfactant, di‐lactose 1,18‐octadec‐9‐enedioate, was favoured with a molar ratio of 3 lactose/Acyl‐Cl with a yield of 33 % after 1 h of reaction. A one‐pot synthesis of agro‐based bolaform surfactant was successfully achieved for the first time in the open literature. Monocatenary and bolaform agro‐based surfactants were isolated by preparative liquid chromatography with high purity according to their chemical structure identification by liquid chromatography coupled to mass spectrometry and 1 H nuclear magnetic resonance. Their critical micellar concentration (12–9 μM) determined by fluorescence spectroscopy with pyrene used as a probe, and hydrophilic:lipophilic balance values (10.7–14.2) indicated that monocatenary and bolaform agro‐based surfactants can act as oils in water emulsion.
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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) | 0.000 | 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".