Chemical Product Design How is it done? Dr. Kevin G. Joback Molecular Knowledge Systems, Inc.

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1 Chemical Product Design How is it done? Dr. Kevin G. Joback

2 O O {1} O C C O CH2 CH2 {1} O O {1} C C O CH2 CH2 O {1} RT a P = V b V ( V + b) + b( V b) B C Z V V RT a P = 2 V b V OH CH 3 CH CH 2 CH Density Viscosity Solubility Melt Point lash Point O O {1} O C C O CH2 CH2 {1} O O {1} C C O CH2 CH2 O {1} A + B B Liquid & Solid wt% Depressant SP, Hydrogen Bonding A + S S A Group SP,p SP,h -CH CH OH >C=O COO Intercept Slope = CH2- # Carbons -CH3 -CH2- -CH2- -COO- Slope = CH2- # Carbons Group SP,p SP,h -CH CH OH >C=O COO Intercept Group SP,p SP,h -CH CH OH >C=O COO Intercept Liquid & Solid wt% Depressant O O {1} O C C O CH2 CH2 {1} O O {1} C C O CH2 CH2 O {1} RT a P = V b V ( V + b) + b( V b) B C Z V V RT a P = 2 V b V OH CH 3 CH CH 2 CH Density Viscosity Solubility Melt Point lash Point O O {1} O C C O CH2 CH2 {1} O O {1} C C O CH2 CH2 O {1} A + B B Liquid & Solid wt% Depressant SP, Hydrogen Bonding A + S S A Slope = CH2- # Carbons -CH3 -CH2- -CH2- -COO- Slope = CH2- # Carbons Group SP,p SP,h -CH CH OH >C=O COO Intercept Liquid & Solid wt% Depressant Molecular Knowledge Systems Located in Bedford, New Hampshire Company Started in 1989 Computer Software Consulting Equations of State Group Contributions Phase Equilibrium = 2 Boiling Point, K Temperature, C Substructure Search Estimate Properties Substructure Search Design Chemical Products Group Contributions T b = Σ n i i SP, Polar Equations of State Group Contributions Phase Equilibrium Substructure Search = 2 Estimate Properties Boiling Point, K Substructure Search Temperature, C Design Chemical Products Group Contributions Group Contributions ormulate Mixtures 15% 20% 31% 34% Boiling Point, K Group Contributions Select Solvents Temperature, C Phase Equilibrium Group Contributions T b = Σ n i i ormulate Mixtures 15% 20% 31% 34% Boiling Point, K Group Contributions SP, Polar Select Solvents Temperature, C Phase Equilibrium SYNAPSE info@molecularknowledge.com CRANIUM info@molecularknowledge.com Emulsifier Phase Oxygen Carrier Continuous Phase Page 2

3 How is it Done? Shaving Cream How did they choose these chemicals? Sodium lauryl sulfate Propylene glycol Diazolidinyl urea Triethanolamine Methylparaben Propylparaben Stearic acid Laureth-23 ragrance Isobutane Propane Water Aloe Page 3

4 How is it Done? Goal The goal of chemical product design is to create chemical structures and mixtures that possess those chemical and physical properties desired by customers. Environmental friendly Skin lubrication Water solubility Pleasant aroma Hair softening Moisturizing oaminess Shaving Cream Sodium lauryl sulfate Laureth-23 Propylene glycol Diazolidinyl urea Methylparaben Propylparaben Triethanolamine Stearic acid ragrance Aloe Isobutane Propane Water Page 4

5 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 5

6 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 6

7 Designing New Refrigerants Next Generation Refrigerants Heat Single Component Condenser H C C Evaporator Heat H Replace R134a Page 7

8 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 8

9 Step 1: Property Constraints Next Generation Refrigerants Heat Condenser Evaporator R134a Replacement Vapor Pressures Match Low Global Warming Not Ozone Depleting P-H Diagrams Match High Oil Solubility Low lammability Low Toxicity Heat Page 9

10 Step 1: Property Constraints 2.50E+3 Which chemicals match R134a Vapor Pressures? Vapor Pressure [kpa] 2.19E E E E E E+2 Pvp(280K) = kpa Pvp(320K) = kpa 3.13E E Temperature [K] Page 10

11 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 11

12 Step 2: Generate Candidates Group Basis CH 3 CH 2 CH C CH 2 CH C O Combinations of 2 ( -CH3 -CH3 ) ( -CH3 -CH2- ) ( -CH3 >CH- ) ( -CH3 =CH2 )... Combinations of 3 ( -CH3 -CH3 -CH3 ) ( -CH3 -CH3 -CH2- ) ( -CH3 -CH3 >CH- )... Page 12

13 Step 2: Generate Candidates Structure Enumeration ( -CH3 -CH3 -CH2- >C< >CH ) CH 3 CH 3 CH 2 CH C CH 3 CH 3 CH 2 CH C CH 3 C CH CH 2 CH C CH 3 CH 2 CH CH 3 3 CH 3 CH C CH 2 CH 3 CH 3 CH 3 CH C CH 2 CH 3 CH C CH 2 CH 3 CH 2 CH C CH 3 CH 3 CH 3 C CH 2 CH CH CH C CH CH CH 3 CH C CH 2 CH 3 C CH CH 2 CH 3 CH 3 CH 3 Page 13

14 Step 2: Generate Candidates Possible Candidate Structures Groups to Choose rom Groups in Molecule easible Candidates ,992 72,214 many Page 14

15 Step 2: Generate Candidates Group Basis CH 3 CH 2 CH C CH 2 CH C O 24 Valid Structures of 4 Groups CH3-CH2-CH2-CH3 CH2=C(CH3)- CH3-CH(CH3)-CH3 CH3-CH2-O- CH3-CH2-CH=CH2 CH3-O-CH2- CH3-CH=CH-CH3 CH2=CH-O- CH2=CH-CH=CH2 CH3-O-O- CH2=C(CH3)-CH3 -CH2-CH2- CH3-CH2-O-CH3 CH3-CH()- CH3-O-O-CH3 -CH=CH- CH3-CH2-CH2- CH2=C()- CH3-CH(CH3)- -CH2-O- CH2=CH-CH2- -O-O- CH3-CH=CH- -CH()- Page 15

16 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 16

17 Step 3: Evaluate Properties Need to Screen Thousands of Candidates CH3-CH2-CH2-CH3 CH3-CH(CH3)-CH3 CH3-CH2-CH=CH2 CH3-CH=CH-CH3 CH2=CH-CH=CH2 CH2=C(CH3)-CH3 CH3-CH2-O-CH3 Ozone Depletion Potential Global Warming Potential Vapor Pressures f(t) lammability Limits Rat LC50 4 Hours Enthalpy f(t,p) Oil Solubility Page 17

18 Step 3: Evaluate Properties Physical Property Estimation Techniques Group Contribution Techniques Equation Oriented Techniques orce ield Techniques Connectivity Indices Parameter its Page 18

19 Group Contribution Techniques OH CH CH 3 2 Group -CH3 -CH3 1 Tb CH 2 -CH CH 3 >CH- -OH ) Select Technique 2) Dissect Structure 3) Get Contributions 4) Insert into Model Tb (est) K Tb (lit) K Tb = Σ i 4 Page 19

20 Boiling Point, Estimation Errors 70 Joback s Method Statistics Observations Avg Error K 60 Avg Abs Err 15.1 K Percentage Avg % Error 4.8 % Max Error K Outliers, Errors N-Methylformamide K Acetamide K (Estimate Data) [K] luorine Cyanogen K K Page 20

21 Equation Oriented Techniques Vapor Pressure - Heptane Pvp ln( P c ) 1 ln = T br 1 Pc 1 Tbr Tr Required Properties Tc Critical Temperature Pc Critical Pressure Vapor Pressure [MPa] Tb Boiling point Temperature [K] Page 21

22 Step 3: Evaluate Properties 1.50E+3 C Property Tb C CH 2 Estimate K Vapor Pressure [kpa] 1.31E E E E E E+2 Candidate R 134a Tc K 1.88E+2 Pc Pvp (280 K) 3406 kpa 452 kpa 1.00E Temperature [K] Pvp (320 K) 1291 kpa R134a Pvp(280K) = kpa R134a Pvp(320K) = kpa Page 22

23 Step 3: Evaluate Properties Candidate Refrigerants Candidate Pvp (280K) Pvp (320K) R 134a -CH-CH-CH2- -CH-O-CH- -C=C- -CH2-CH2- -CH-CH2-CH- CH3-C2-CH3 CH2=C-C Page 23

24 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 24

25 Solvents in Chemical Products Solvents Applications Personal Care Products Cosmetics / ragrances Pesticides / Herbicides Cleaning / Degreasing Adhesives / Sealants Process Solvents Paints / Coatings Pharmaceuticals Printing Inks Detergents Property Constraints Evaporation rate Solute solubility Vapor pressure reezing point Boiling point lammability Recyclability Viscosity Irritancy Toxicity Listed Page 25

26 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 26

27 Step 1: Property Constraints Solubility at 25 C Solute = Benzoic Acid Could solvent blends give higher solubility? Solvent Pyridine Dimethyl sulfoxide N,N-Dimethylformamide N,N-Dimethylacetamide N-Methylformamide Methanol Ethanol 2-Propanol wt % A. Beerbower, P. L. Wu and A. Martin. "Expanded Solubility Parameter Approach I: Naphthalene and Benzoic Acid in Individual Solvents." Journal of Pharmaceutical Sciences. Volume 73, number 2, page , Page 27

28 Step 1: Property Constraints Solubility at 25 C Solute = Benzoic Acid Could solvent blends give higher solubility? Solvent wt % Pyridine 64.0 Dimethyl sulfoxide 61.9 N,N-Dimethylformamide 61.7 N,N-Dimethylacetamide 60.7 N-Methylformamide 51.9 Solubility > 50.0 wt% A. Beerbower, P. L. Wu and A. Martin. "Expanded Solubility Parameter Approach I: Naphthalene and Benzoic Acid in Individual Solvents." Journal of Pharmaceutical Sciences. Volume 73, number 2, page , Page 28

29 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 29

30 Step 2: Generate Candidates 62 Common Solvents Generate all Combinations 1,891 Binary Solvent Blends Solute + 1,1,1-Trichloroethane + 1,2-Dichloroethane Solute + 1,1,1-Trichloroethane + 1,2-Propylene glycol Solute + 1,1,1-Trichloroethane + 1,4-Dioxane Solute + 1,1,1-Trichloroethane + 1-Butanol Solute + Water + n-octane Solute + Water + n-pentane Solute + Water + o-xylene Solute + Water + p-xylene Page 30

31 Step 2: Generate Candidates 34,596 compositions Solute Solvent1 Solvent Solvent Ratio 1 : Solvent Ratio 3 : 1 Page 31

32 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 32

33 Step 3: Evaluate Properties 70.0 Benzoic acid + Chloroform Temperature, C UNIAC VLE Data Values ln x + lnγ = Benzoic Acid, wt% H R fus 1 T 1 T m Data from: Thati, Nordström and Rasmuson. Journal of Chemical and Engineering Data. Volume 55, number 11, page , Page 33

34 Step 3: Evaluate Properties Candidate Binary Blends Solvent 1 wt % Solvent 2 wt % BA wt % Ethanol 15.0 Methanol Ethylene glycol 54.4 Methyl acetate Butanone Propanol Acetone 54.7 Butyl acetate BA Solubility in Pure Solvents Acetone (32.41 wt%) Butyl acetate (17.7 wt%) Page 34

35 Designing an Anti-icing luid Aircraft Wing Page 35

36 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 36

37 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 37

38 Anti-icing luid Design Anti-icing luid Aircraft Wing Biological Oxygen Demand reezing Point Depression Viscous Shear Thinning Aquatic Toxicity lammability Corrosivity Wettability Color Page 38

39 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 39

40 Step 2: Generate Candidates reezing Point Depressants: 419 Corrosion Inhibitors: 17 Surfactants: 19 Thickeners: 5 Antifoams: 2 Dyes: 1 Water Aircraft Anti-icing luid (after preliminary screening) (generate independent sub-formulations) Page 40

41 Design Steps Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 41

42 Anti-icing luid Design Anti-icing luid Aircraft Wing Biological Oxygen Demand reezing Point Depression Viscous Shear Thinning Aquatic Toxicity lammability Corrosivity Wettability Color Page 42

43 Step 3: Evaluate Properties Estimate reezing Point Depression Assume a Simple Eutectic Property Model Temp, C Liquid ln x + lnγ = H R fus 1 T Need γ, H fus, T m 1 T m Solid for each candidate Weight % Page 43

44 Step 3: Evaluate Properties Estimate Mixture lash Points Le Chatelier s Method LL mix = 1 yi LL VLE Calculation LL = mix yi y i = x γ P i i vp i ( T f i ) lash Point [K] Decane - Squalane Data Values Estimates Wt frac Squalane Page 44

45 Step 3: Evaluate Properties DEG without Antifoam DEG with Antifoam ormulation remained on surface for more than 30 minutes without draining ACRP 02-01

46 Step 3: Evaluate Properties Niagara alls, ebruary 2006 Page 46

47 Anti-icing luid Design Aircraft Wing Anti-icing luid Biological Oxygen Demand reezing Point Depression Viscous Shear Thinning Aquatic Toxicity lammability Corrosivity Wettability Color inal ormulation 1. Diethylene glycol 2. Tergitol TMN Triethanolamine 4. Carbopol Shilling Green 6. Water Page 47

48 How is it Done? Chemical Product Design (3 Steps) 1. Compile Property Constraints: analysis 2. Generate Candidates: combination 3. Evaluate Properties: estimation (refrigerants, solvents, anti-icing fluids) Page 48

49 Questions? Michael Hill Kevin G. Joback Page 49

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