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Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
Measurement and application of equivalent alkane carbon number
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Measurement and application of equivalent alkane carbon number

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  • 1. Measurement and Application of Equivalent Alkane Carbon Number of Fragrance Oils AOCS Meeting – May, 2014 D.R. Scheuing, Erika Szekeres Clorox
  • 2. Outline Introduce the Fragrance Problem Relate the Problem to Hydrophilic-Lipophilic Difference (HLD) and Equivalent Alkane Carbon Number (EACN) Introduce a Practical Approach to the Problem Example and Watch-Outs
  • 3. The Good News - Chemically Complex Modern Fragrances Drive Consumer Preference
  • 4. The Bad News - Chemically Complex Modern Fragrances Drive Consumer Preference
  • 5. Multiple Fragrances Needed ! Lemon 1.5% Surfactant Lavender 1.7% Surfactant Watery Fresh 1.2% Surfactant Spring Blooms 1.3% Surfactant 4 Fragrances Need 4 Different Minimum Surfactant Levels One Answer = 4 Different Formulations Another Answer = Use 1.7% Surfactant For All Or – Rank the Fragrances in Terms of Polarity with a Simple Method Design One Robust Formulation for All Fragrances Understand that Wide Range in Polarities Will Drive Costs
  • 6. Classic Fish Diagram Shows the Formulation Problem – in terms of Temperature Surfactant concentration Temperature w/o micelle + excess water o/w micelle + excess oil bicontinuous 3 phase w oil oil oil water w oil Product Non-ionic surfactant
  • 7. HLD View of the Problem – What is the Range of Fragrance HLD? Surfactant concentration HLD (oilpolarity) 2 phase 2 phase 3 phase Polar fragrance oil Hydrophobic fragrance oil Single phase (-) (+) 𝑪 𝒔 HLD = hydrophilic-lipophilic difference Varied via oil polarity variation
  • 8. A Wider Range of Fragrance HLD Requires Higher Concentration of a Given Surfactant – Costs Are Increased Surfactant concentration HLD (oilpolarity) 2 phase 2 phase 3 phase (-) (+) 𝑪 𝒔 𝑪 𝒔 Hydrophobic fragrance oil Polar fragrance oil
  • 9. Even Worse for Cost – Selection of the Wrong Surfactant Package for the Range of Fragrances Surfactant concentration HLD (oilpolarity) 2 phase 2 phase 3 phase (-) (+) 𝑪 𝒔 𝑪 𝒔 Surfactant is too hydrophobic for this range of HLD – Higher Concentration Required Polar fragrance oil Hydrophobic fragrance oil
  • 10. Rank Fragrance Oil Polarities Via EACN Measurement Use the HLD equation for anionic surfactant 0 = ln 𝑺∗ − 𝑘 ∙ 𝑬𝑨𝑪𝑵 + 𝐶𝑐 𝐻𝐿𝐷 = ln 𝑆 − 𝑘 ∙ 𝑬𝑨𝑪𝑵 + 𝐶𝑐 − 𝑎 𝑇 ∙ 𝑇 − 25 + 𝑓(𝐴) HLD (reflects overall formulation hydrophobicity): • Electrolyte (S) – vary this experimentally • Oil polarity (EACN) - unknown • Surfactant head/tail (k and Cc) – these are known • Temperature (T) – fix this at 25C • Alcohol – f(A) don’t add alcohol Experimentally determine S* at which optimum formulation is achieved HLD = 0 Calculate EACN 𝐸𝐴𝐶𝑁 = ln 𝑆∗ + 𝐶𝑐 𝑘
  • 11. Salt scan on the SOW phase map Surfactant concentration, wt% NaClwt% w/o micelle + excess water o/w micelle + excess oil HLD =0S* Anionic surfactant
  • 12. Salt scan in the test tubes with SDHS surfactant and Limonene 0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 100% 2.7 3.7 4.7 5.7 6.7 7.8 8.8 9.8 10.8 11.8 12.9 13.9 Relativephasevolume aq. NaCl % Relative phase volumes Excess water Microemulsion Excess oil 0 1 2 3 4 5 2 3 4 5 6 7 8 9 10 11 12 13 14 Volume,ml NaCl % Volume of oil and water in the microemulsion phase Water OIL S* S* = 7% EACN = 6.05 The more positive the EACN the more hydrophobic the oil SDHS= sodium dihexyl sulfosuccinate Water/oil volume ratio = 1
  • 13. Adaptation to Fragrance Oil Ranking Problem • Fragrance oils are quite polar • The Winsor I-III-II phase sequence might be impossible to find Solution • Run salt scan with fragrance oil/limonene mixture rather than with pure fragrance oil and determine the EACN of the oil mixture; • Run a limonene salt scan control to determine limonene EACN • Use linear mixing rule by volume to calculate fragrance oil EACN from oil mixture EACN and limonene EACN data
  • 14. Salt scan with fragrance/limonene mixture 0 0.5 1 1.5 2 2.5 3 3.5 4 4.5 5 2 3 4 5 6 7 8 9 10 11 12 13 14 Volume,ml NaCl % Volume of oil and water in the microemulsion phase W… O… 0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 100% 2.69 3.71 4.74 5.72 6.74 7.77 8.80 9.82 10.8511.8312.8513.88 Relativephasevolume aq. NaCl t% Relative phase volumes Excess water Microemulsion Excess oil S* oil mixture = 4.8% EACN fragrance = - 5.05 S* mix  calculate EACN mix using HLD  calculate EACN fragrance with linear mixing rule Oil mixture = 0.2 vol fraction fragrance/limonene mixture
  • 15. Watch-outs Limonene oxidation – polar shift possible Run SDHS +limonene control scan SDHS solution from Aldrich seems reproducible Ester hydrolysis/residual alcohol ? Room temperature is usually good enough Use water/oil ratio = 1 Always add fragrance oil at 0.2 volume fraction
  • 16. Calculated fragrance EACN depends on mixing ratio ! Oil mixture EACN is a nonlinear function of mixing ratio -4 -3 -2 -1 0 1 2 3 4 5 6 7 0 0.2 0.4 0.6 0.8 1 EACNofoilmixture Fragrance oil volume fraction Limonene + fragrance oil mixture, 10% SDHS, salinity scan using NaCl -14 -12 -10 -8 -6 -4 -2 0 0 0.2 0.4 0.6 0.8 1 EACNofpurefragrance Fragrance oil volume fraction EACN of fragrance oil calculated using linear mixing rule Stick to a fixed 0.2 volume fraction for all EACN measurements
  • 17. Measured EACN of Fragrances and Solvents 0 1 2 3 4 5 6 7 8 9 10 -14 -12 -11 -10 -9 -8 -6 -5 -4 -3 0 1 5 Frequency Fragrance EACN value Typical fragrance EACN values -28 -26 -24 -22 -20 -18 -16 -14 -12 -10 solvent 1 solvent 2 solvent 3 solvent 4 solvent 5 Solvent EACN values
  • 18. Example - Individual Fragrance Components Nerol – 97% from Acros EACN measured with current approach = -21.9 Linalool – 97% from Acros EACN measured with current approach = -14.5 Empirical Formula = C10H18O
  • 19. Summary Complex Modern Fragrances Exhibit a Wide Range of Polarity Formulation Costs Can Be Driven By Range of Polarity – Equivalent to a Range in HLD Ranking of Fragrance Polarities Via EACN Drives Rapid Formulation Optimization Simple Approach – Measure EACN of Limonene/Fragrance Oil Mixtures to Rank Fragrances Rankings Will Be Correct – Even if the Measured EACNs are Not the Real Ones Approach Is Practical – And Could Drive Inter-Lab Collaboration
  • 20. Thanks ! AOCS – S&D Division Clorox And – You – The Audience and Consumer !
  • 21. References The EACN scale for oil classification revisited thanks to fish diagrams Journal of Colloid and Interface Science 312 (2007) 98–107 S. Queste, J.L. Salager, R. Strey, J.M. Aubry Classification of terpene oils using the fish diagrams and the Equivalent Alkane Carbon (EACN) scale Colloids and Surfaces A: Physicochem. Eng. Aspects 338 (2009) 142–147 Francois Bouton, Morgan Durand, Véronique Nardello-Rataj, Marie Serry, Jean-Marie Aubry A Two-State Model for Selective Solubilization of Benzene-Limonene Mixtures in Sodium Dihexyl Sulfosuccinate Microemulsions Langmuir 2004, 20, 6560-6569 Erika Szekeres, Edgar Acosta, David A. Sabatini, Jeffrey H. Harwell

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