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1,2-Hexanediol (C₆H₁₄O₂) is a clear, colorless synthetic liquid diol widely used in cosmetics and industrial applications. Key points:
Dual Solubility:
Soluble in water and oils (unlike shorter-chain diols), making it versatile.
Humectant:
Binds moisture in skincare (serums, creams) to prevent dryness.
Preservative Booster:
Enhances efficacy of antimicrobials (e.g., phenoxyethanol) against bacteria/fungi.
Solvent & Carrier:
Dissolves actives (vitamins, pigments) and improves product texture.
Cosmetics: Moisturizers, sunscreens, makeup (replaces glycerin for lighter feel).
Cleansers: Lowers surface tension for better oil removal.
Industrial: Coatings, inks, antifreeze.
Low Irritation: Safe for sensitive skin (OECD-tested).
Biodegradable: Environmentally compliant.
Labeling: Often listed as "1,2-Hexanediol" in INCI.
Why Formulators Use It:
Multifunctional (reduces need for multiple additives).
Extends shelf life without parabens.
Improves spreadability without stickiness.
1,2-Hexanediol (C₆H₁₄O₂) is a saturated vicinal diol (a 6-carbon chain with two adjacent hydroxyl groups). Here are its key chemical characteristics:
IUPAC Name: *Hexane-1,2-diol*
Molecular Formula: C₆H₁₄O₂
Structural Formula:
HO−CH₂−CH(OH)−CH₂−CH₂−CH₂−CH₃
Vicinal diol (OH groups on C1 and C2).
Chiral center at C2 (exists as R/S enantiomers; typically used as racemate).
Physical State: Colorless, viscous liquid (mp: −10°C; bp: 223°C).
Solubility:
Miscible in water (forms H-bonds).
Soluble in organic solvents (ethanol, acetone) and oils (log P: −0.25).
Hydrophilic-Lipophilic Balance (HLB): ~5.3 (moderate surfactant properties).
Hydrogen Bonding: Strong H-bond donor/acceptor → humectancy.
Reactivity:
Dehydration: Forms aldehydes/ketones under acid catalysis.
Esterification: Reacts with acids to yield esters (e.g., in polymer synthesis).
Coordination Chemistry: Binds metal ions (e.g., as a chelator).
Preservative Mechanism: Disrupts microbial membranes via OH group interactions.
Industrial Route:
Hydroxylation of 1-Hexene with peracetic acid:
CH2=CH−CH2CH2CH2CH3+CH3COOOH→HO−CH2−CH(OH)−CH2CH2CH2CHCHX2=CH−CHX2CHX2CHX2CHX3+CHX3COOOH ——>
HO−CHX2−CH(OH)−CHX2CHX2CHX2CHX3
| Role | Chemical Basis |
|---|---|
| Humectant | H-bonding with water → retains moisture |
| Solvent/Carrier | Dual solubility (polar/non-polar) |
| Preservative Aid | Disrupts microbial membrane integrity |
| Viscosity Modifier | H-bonding network → thickens solutions |
IR: Broad O−H stretch (3200–3400 cm⁻¹); C−O stretch (1050–1100 cm⁻¹).
NMR (¹H):
C1−OH: δ 3.5–3.7 ppm (t, 2H)
C2−OH: δ 3.3–3.5 ppm (m, 1H)
C2−H: δ 3.4–3.6 ppm (m, 1H)
Low Toxicity: LD₅₀ (oral, rat) >2000 mg/kg.
Biodegradable: Readily metabolized via β-oxidation.
Non-Irritating: Safe for cosmetic use (OECD 439).
Why Chemists Value It: Combines water solubility (from vicinal OH) with lipophilic compatibility (C4-C6 alkyl chain), enabling versatile formulations. Its dual functionality reduces the need for multiple additives, aligning with "clean chemistry" trends.
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