Precision measurement of the growth rate and mechanism of ibuprofen {001}
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1 Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 214 SUPPLEMENTARY INFORMATION Precision measurement of the growth rate and mechanism of ibuprofen {1} and {11} as a function of crystallization environment T. T. H. Nguyen, R. B. Hammond, K. J. Roberts* Institute of Particle Science and Engineering, Institute of Process Research and Development, School of Process, Environmental and Materials Engineering, University of Leeds, Leeds, LS2 9JT, Leeds I. Marziano, G. Nichols Pfizer Worldwide Research and Development, Sandwich, CT13 9NJ, UK (*) Corresponding author s K.J.Roberts@leeds.ac.uk Abstract The crystallisation of ibuprofen under diffusion-limited conditions measured as a function of supersaturation, solvent and reactor scale is described in the main paper and in this supplementary material some additional information is provided. This comprises: Details concerning the raw ATR UV/Vis spectra collected and the associated calibration used to determine the concentration of ibuprofen in 95% ethanol/water, ethyl acetate, and acetonitrile solvents as a function of temperature (section S1.1) Details of the gravimetric calculations used for the determination of the solubility of ibuprofen in toluene solutions (section S1.2) All the raw in-situ microscopy image data and its associated analysis which underpin the determination of face-specific growth rates as presented in the main paper (section S2). 1
2 S1. Data related to solubility determination in 95% ethanol/water, ethyl acetate, and acetonitrile solvents by ATR UV/Vis spectroscopy S1. 1 ATR UV/Vis method development The Beer-Lambert law states that the absorbance of a solution is directly proportional to the concentration of the absorbing species in the solution and the path length. Hence, ATR UV/Vis spectroscopy can be employed to determine the concentration of ibuprofen in a solution for a fixed path length. The calibration curve of ibuprofen was determined by measuring absorbance versus a range of concentrations using the specific absorbance peak of ibuprofen at 264 nm (Figure S1) (a) Absorbance g/ml.8g/ml 1g/ml 1.2g/ml 1.4g/ml Wavelength (nm).8 (b) Absorbance g/ml.6g/ml.8g/ml 1.g/ml Wavelength (nm)
3 Absorbance (c).1g/ml.2g/ml.3g/ml.4g/ml Wavelength (nm) Absorbance (d) Acetonitrile Ethyl acetate Ethanol Concentration (g/ml) Figure S1 Spectra of ibuprofen in 95% ethanol/water (a), ethyl acetate (b) and acetonitrile (c) showing absorbance increase with increasing concentration of solutions and from these absorbances at 264 nm and known concentrations, calibration curves (d) were obtained. Table S1 Calibration line of ibuprofen in 95% ethanol/water, ethyl acetate and acetonitrile at temperature from o C Solvents 95% Ethanol/Water Ethyl acetate Acetonitrile Calibration line y =.818x.172 y =.786x.34 y =.53x
4 Table S1 shows the regression fits obtained from the calibration curves from which the solubility of ibuprofen in these 3 solvents over the temperature range o C was determined. Absorbance Wavelength (nm) Figure S2 An example of spectra of ibuprofen in ethyl acetate at 15, 2, 25, 3 and 35 C showing absorbances increase with increasing temperature of saturated solutions and λmax does not shift with temperature Spectroscopic exanimation of the ibuprofen solutions in the UV region revealed a strong absorbance maximum at about 264 nm. The λmax was not found to shift even in different solvents and concentration nor even as a function of temperature. The ATR-UV/Vis spectroscopy calibration shows a linear correlation between UV/Vis absorbance intensity and the solute concentration for different concentrations of ibuprofen in 4
5 solvents. For a constant solution concentration, absorbance was found to be quite constant as a function of a temperature, as shown in Figure S2. S1.2 Data related to solubility determination toluene solvents by gravimetric methods Table S2 provides the raw gravimetric data together with the associated determination of the solubility of ibuprofen in toluene solutions over the temperature range from C was determined. Table S2 Solubility of ibuprofen in toluene solutions over the temperature range from C T( C) Sample Sample Sample C(g/g) STDEV
6 S2. Crystal growth rate measurement in the.5ml cuvette cell and the 15ml jacketed vessel The data presented comprises plots of growth rate versus time for the {11} and {1} faces for all the crystals measured together with a representative image set for one of these crystals. S2.1 Data from the.5ml cuvette cell S % Ethanol/Water Solutions σ = The {11} face at σ = 1.15 y = 19.3x y = 22.6x y = 22.5x y = 21.7x y = 21.7x The {1} face at σ = 1.15 y = 1.9x y = 14.8x y = 12.2x y = 14.3x y = 14.1x
7 σ = The {11} face at σ =.89 y = 16.1x y = 14.x y = 14.5x y = 12.5x The {1} face at σ =.89 y = 7.4x y = 5.7x y = 5.9x y = 5.8x σ = The {11} face at σ =.79 y = 12.5x y = 1.7x y = 11.2x y = 13.5x y = 9.5x The {1} face at σ =.79 y = 5.1x y = 4.3x y = 4.1x y = 4.4x y = 4.9x
8 σ =.66 Distance from center to faces (μm) The {11} face at σ =.66 y = 7.6x y = 6.6x y = 6.9x y = 1.3x y = 11.2x The {1} face at σ =.66 y = 4.4x y = 3.5x y = 2.5x y = 4.x y = 3.6x S2.1.2 Ethyl Acetate Solutions σ = 1.12 Disntance from center to face (μm) The {11} face at σ = 1.22 y = 55.3x y = 72.2x y = 5.9x y = 62.8x y = 66.5x y = 6x The {1} face at σ = 1.22 y = 15.4x y = 9.3x y = 14.7x y = 13.2x y = 9.7x y = 1.8x
9 σ = The {11} face at σ = 1.6 y = 48.1x y = 55.4x y = 63x y = 48.7x y = 56.7x y = 47.7x y = 47.6x The {1} at σ = 1.6 y = 8.9x y = 1.4x y = 1x y = 9.8x + 74 y = 9.6x y = 9.3x y = 9.9x σ = The {11} face in at σ =.97 y = 54.6x y = 47.7x y = 47.6x y = 52.1x y = 46x y = 45.1x The {1} face at σ =.97 y = 9.5x y = 8.7x y = 8.4x y = 7.3x y = 7.4x
10 σ = The {11} face at σ =.85 y = 37.9x y = 43.1x y = 48.7x y = 42x y = 41.8x y = 43.9x y = 43.5x y = 39.1x The {1} face at σ =.85 y = 6.6x y = 6.5x y = 5.7x y = 6.8x y = 5.9x y = 6x σ = The {11} face at σ =.76 y = 34.7x y = 34.5x y = 37.6x y = 36.3x y = 42.8x y = 38.9x The {1} face at σ =.76 y = 3.3x y = 4.2x y = 4.1x y = 4.8x y = 5.x y = 4.8x
11 σ = The {11} face at σ =.69 y = 3.8x y = 33.6x y = 31.6x y = 31.4x y = 29.3x Distance from center to faces (μm) The {1} face at σ =.69 y = 4.2x y = 3.3x y = 3.4x y = 3.2x + 22 y = 3.2x σ = The {11} face at σ =.54 y = 15.9x y = 18.9x y = 2.7x y = 16.6x y = 16.x The {1} face at σ =.54 y = 2.2x y = 1.4x y = 1.6x + 3 y = 1.9x y = 1.7x
12 S2.1.3 Acetonitrile Solutions σ = The {11} at σ = 1.31 y = 113.4x y = 136x y = 19.2x y = 11x y = 99.5x y = 13.9x The {1} face at σ = 1.31 y = 17.3x y = 13.4x y = 17.3x y = 12.5x y = 16.1x σ = The {11} face at σ = The {1} face at σ = y = 9.4x y = 8.5x y = 94x y = 93.5x y = 99.6x y = 96.5x y = 1.5x y = 11.8x y = 1.5x y = 13x + 36 y = 7.9x
13 σ = The {11} face at σ = 1.3 y = 77.8x y = 88.2x y = 98.4x y = 7.2x y = 67.7x y = 77.x The {1} face at σ = 1.3 y = 1.7x y = 6.3x y = 6.3x y = 5.9x y = 7.7x σ = The {11} face at σ =.93 y = 71x y = 61.3x y = 55.7x y = 55.7x y = 55.5x Distant from cneter to face (μm) The {1} face at σ =.93 y = 5.1x y = 5.5x y = 4.6x y = 4.8x y = 4.9x
14 σ = The {11} face at σ =.79 y = 6.5x y = 49.8x y = 48.7x y = 48x y = 5.3x The {1} face at σ =.79 y = 3.2x y = 3.3x y = 3.4x y = 3.7x y = 4.8x y = 2.9x S2.1.4 Toluene Solutions σ = The {11} face at σ =.86 y = 32.6x y = 38.5x y = 38.9x y = 29.2x y = 37.4x y = 29.7x The {1} face at σ =.86 y = 3.1x y = 3.3x y = 3.4x y = 3.x y = 3.1x y = 2.x
15 σ = The {11} face at σ =.78 y = 29.x y = 27.5x y = 31x y = 3.5x y = 34.4x The {1} face at σ =.78 y = 2.1x y = 2.5x y = 2.2x y = 2.4x + 22 y = 2.2x σ = The {11} face at σ =.7 y = 25.6x y = 27x y = 28.9x y = 28.9x y = 3.8x y = 26.4x The {1} face at σ =.7 y = 2.x y = 1.5x y = 2.x + 23 y = 1.9x y = 1.7x
16 S2.2 Data from the 15ml jacketed vessel S % Ethanol /Water Solutions σ = The {11} face at σ = 1.15 y = 21.6x y = 31.5x y = 25.6x y = 22.1x y = 22.4x Distance from center face (μm) The {1} face at σ = 1.15 y = 13.4x y = 14.4x y = 12.8x y = 12.9x y = 12.6x σ = The {11} face at σ =.97 y = 26.6x y = 2.9x y = 25.5x y = 28.3x y = 27x y = 25.8x y = 22.5x The {1} face at σ =.97 y = 17.8x y = 13.3x y = 15.8x y = 14x y = 14.8x y = 16x
17 σ = The {11} face at σ =.89 y = 18.3x y = 16.9x y = 16.4x y = 16.6x y = 16.1x Distance from cneter to face (μm) The {1} face at σ =.89 y = 7.9x y = 6.6x y = 6.2x y = 8.1x y = 7.2x σ = The {11} face at σ =.66 y = 1.3x y = 9.9x y = 11.7x y = 12.2x y = 11.3x Distance from center face (μm) The {1} face at σ =.66 y = 4.2x y = 3.6x y = 4.5x y = 4.2x y = 3.4x
18 S2.2.2 Ethyl Acetate Solutions σ = 1.22 The {11} face at σ = y = 61.7x y = 7.6x y = 59.5x y = 67.3x y = 65.2x y = 68.5x y = 67.1x y = 63.5x σ = The {1} face at σ = 1.22 y = 13.7x y = 15.3x + 9. y = 15.8x y = 13.2x y = 13.6x y = 14.1x y = 12.7x y = 12.3x The {11} face at σ = 1.6 y = 58.6x y = 56.5x y = 53.8x y = 58.1x y = 59.1x y = 62.1x y = 62.3x The {1} face at σ = 1.6 y = 12.4x y = 13.x y = 12.9x y = 12.9x y = 11.8x y = 12.7x y = 12.2x
19 σ =.97 The {11} face at σ =.97 The {1} face at σ = y = 55.3x y = 5.1x y = 51.3x y = 54.3x y = 55.1x y = 52.1x y = 11.4x y = 9.2x y = 9.4x y = 1.8x y = 1.1x y = 9.8x σ = The {11} face at σ =.85 y = 51.9x y = 51.8x y = 44.9x y = 46.2x y = 46x y = 41.3x The {1} face at σ =.85 y = 7.1x y = 6.9x y = 6x + 51 y = 5.8x y = 5.3x
20 σ = The {11} face at σ =.76 y = 44.2x y = 41.7x y = 43.7x y = 39.7x y = 39x The {1} face at σ =.76 y = 6.1x y = 5.8x y = 5.9x y = 6.1x y = 5.1x σ = The {11} face at σ =.69 y = 36.6x y = 37.3x y = 4.3x y = 33.3x y = 38.76x y = 38.1x y = 31.84x The {1} face at σ =.69 y = 4.32x + 4 y = 4.4x y = 4.4x y = 2.5x
21 σ =.54 Distance from center to face(μm) The {11} face at σ =.54 y = 24.8x y = 15.4x y = 16.6x y = 2.3x y = 18.6x The {1} face at σ =.54 y = 1.9x y = 1.9x + 51 y = 1.5x y = 2.2x y = 1.8x S2.2.3 Acetonitrile Solutions σ = The {11} face at σ = 1.31 y = 137.7x y = 121.5x y = 115.5x y = 128.7x y = 11.3x y = 126x y = 115.2x y = 141.9x y = 129x y = 12x y = 13x The {1} face at σ = 1.31 y = 17.9x y = 18x + 93 y = 18.3x y = 16.x y = 16.5x y = 14.5x
22 σ = 1.12 The {11} at σ = 1.12 The {1} face at σ = y = 117x y = 18.7x y = 12.5x y = 93.x y = 13.5x y = 13.8x y = 13.4x y = 12.9x y = 12.5x y = 1.8x σ = The {11} face at σ = 1.3 y = 98.7x y = 83.1x y = 84.8x y = 86.2x y = 74.6x y = 91.6x y = 78.8x The {1} face at σ = 1.3 y = 1.2x y = 9.8x y = 9.9x y = 9.5x y = 9.3x y = 9.2x y = 8.1x
23 σ = The {11} face at σ =.93 y = 7.7x y = 75.6x y = 77.7x y = 7.2x y = 7.4x The {1} face at σ =.93 y = 5.9x y = 5.6x y = 6.3x y = 5.6x y = 5.7x σ = The {11} face at σ =.75 y = 47.5x y = 57.5x y = 54x y = 6.3x y = 62.2x y = 55.9x y = 61x y = 51.8x The {11} face at σ =.75 y = 5.5x + 36 y = 2.875x y = 5.7x y = 5x y = 5.35x y = 5.425x y = 4.65x
24 S2.2.4 Toluene Solutions σ = The {11} face at σ = 1.17 y = 42.3x y = 46.6x y = 43.1x y = 46x y = 41x The {1} face at σ = 1.17 y = 4.8x y = 5.5x y = 4.4x y = 5.3x + 35 y = 5.1x σ =.86 Distance form center to face (μm) The {11} face at σ =.86 y = 34.5x y = 36.6x y = 4.1x y = 43.3x y = 4.1x y = 37.4x The {1} face at σ =.86 y = 3.3x + 57 y = 4.4x y = 4.5x y = 3.4x y = 2.3x y = 3.2x
25 σ =.78 Distance from center to face (µm) The {11} face at σ =.78 y = 34.7x y = 38.6x y = 27.9x y = 34.5x y = 37.4x y = 28.7x Distance from center to face (µm) The {1} face at σ =.78 y = 3.1x y = 2.9x y = 2.2x y = 2.9x σ =.7 Distance from center to face (µm) The {11} face at σ =.7 y = 35.4x y = 32.9x y = 31.4x y = 29.1x y = 31.4x Distance from center to face (µm) The {1} face at σ =.7 y = 2.9x y = 1.9x y = 2.9x y = 2.2x y = 2.x
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