Electronic Supplementary Information for

Green Solvents from Glycerol. Synthesis and PhysicoChemical properties of Alkyl Glycerol Ethers.
José I. García,a Héctor García-Marín,a José A. Mayoral,a,b and Pascual Pérezc
a

Dept. Organic Chemistry, Instituto de Ciencia de Materiales de Aragón, Facultad de Ciencias, Univ. de ZaragozaCSIC, Pedro Cerbuna, 12, E-50009 Zaragoza, Spain. Fax:+34 976762077; Tel: +34 976762271; E-mail:
jig@unizar.es.

b

Instituto Universitario de Catálisis Homogénea, Facultad de Ciencias, Univ. de Zaragoza, Pedro Cerbuna, 12, E50009 Zaragoza, Spain. Fax: 976762077; Tel: 976762077; E-mail: mayoral@unizar.es.

c

Dept. Physical Chemistry and Organic Chemistry, , Facultad de Ciencias, Univ. de Zaragoza, Pedro Cerbuna, 12,
E-50009 Zaragoza, Spain. Fax: 976762077; Tel: 976762271; E-mail: pascual@unizar.es.

Content
1. Table 1S. Physico-chemical properties values

2S–3S

2. List of solvent names abbreviations used in Figures 1, 4, 5, 6, and 7

3S

3. Table 2S. Experimental vapour pressures

4S

4. Figure 1S. Kirkwood function vs. Dielectric function plot

4S

5. Experimental procedures for the physico-chemical properties measurements

5S–6S

6. References

6S

7. Table 3S. Characterization of the glycerol-derived solvents prepared

7S–24S

1S

Table 1S. Physico-chemical properties of glycerol-based solvents.
Solvents

ETN

π*

α

μ (D)

ε

1,0,0
2,0,0
4,0,0
1,0,1
3i,0,1
4,0,1
4i,0,1
4t,0,1
3i,0,4
4,0,4
4t,0,4
4i,0,4
3i,0,2
4,0,2
4t,0,2
4i,0,2
3i,0,3i
4,0,3i
4t,0,3i
4i,0,3i
3i,0,3F
4,0,3F
4t,0,3F
4i,0,3F
3F,0,3F
5F,0,5F
7F,0,5F
1,1,1
3i,1,1
3i,4,1
4t,1,1
4t,4,1
4,1,1
4,4,1
4i,1,1
4i,4,1
3i,2,1
3i,1,2
4t,2,1
4t,1,2
4,2,1
4,1,2
4i,2,1
4i,1,2
3i,2,2

0,71
0,69
0,68
0,61
0,49
0,48
0,49
0,44
0,43
0,45
0,39
0,46
0,45
0,45
0,41
0,46
0,46
0,50
0,37
0,44
0,59
0,60
0,57
0,60
0,70
0,70
0,69

0,86
0,77
0,68
0,73
0,71
0,96
0,62
0,71
0,16
1,09
0,75
0,57
0,75
0,96
0,62
0,71

0,83
0,86
0,91
0,72
0,47
0,27
0,55
0,36
0,77
0,10
0,22
0,50
0,36
0,21
0,36
0,40

3,416
3,424
3,148
2,929
2,508
2,424
2,353
2,359

21,878
18,623
12,553
12,963
7,861
6,945
6,561
6,612

Kirkwood
functiona
0,4664
0,4608
0,4425
0,4443
0,4103
0,3993
0,3938
0,3945

2,393
2,259
2,257
2,541
2,459
2,317
2,33

5,642
5,163
5,149
7,386
6,599
5,965
5,997

0,3779
0,3676
0,3672
0,4049
0,3944
0,3840
0,3846

1,25
0,62
0,57
0,71
0,84
0,53
0,57
0,38
0,56
0,55

0,08
0,29
0,47

2,314

5,614

0,3773

0,70
0,61
0,79
0,82
1,04
1,01

3,361
3,446
3,642
3,431
4,098
3,941
3,903
2,219
1,993

11,986
10,235
11,197
10,013
14,616
10,438
8,629
6,838
4,918

0,4399
0,4301
0,4359
0,4287
0,4504
0,4314
0,4178
0,3978
0,3616

0,15
0,21

-0,06
0,53

0,32
0,02

0,17
0,17

-0,02
0,15

0,35
0,22

0,15
0,16
0,16

-0,23
0,10
0,16

0,47
0,23
0,21

0,16

0,32

0,07

0,18

ΔlogP98
-0,9996
-0,6508
0,3291
-0,5911
0,1352
0,7376
0,6007
0,3402
1,4639
2,0663
1,6689
1,9294
0,4840
1,0864
0,6890
0,9495
0,8615
1,4639
1,0665
1,3270
1,1426
1,7450
1,3476
1,6081
1,4237
2,4069
3,3901
-0,1826
0,5437
1,8724
0,7487
2,0774
1,1461
2,4748
1,0092
2,3379
0,8925
0,8925
1,0975
1,0975
1,4949
1,4949
1,3580
1,3580
1,2413

b.p
(ºC)
222
221
249
170
188
208
200
195
223
248
230
229
187
220
204
214
202
224
202
215
176
210
199
205
197
204
206
150
170
215
180
219
199
234
193
227
161
183
190
193
209
209
198
201
192

AHvap
(kJ/mol)
43,03
45,02
41,11
30,99
38,21
58,34
50,92
55,71
56,93
68,36
44,50
55,69
26,18
44,01
43,68
40,86
40,68
53,32
46,09
47,21
37,03
57,40
45,79
56,77
51,00
43,92
57,57
30,24
39,88
45,89
34,63
46,77
51,82
59,08
51,20
50,63
26,02
48,72
43,99
43,18
51,60
52,78
45,99
51,59
43,90

Kinematic viscosity
(cSt)
34,011
33,251
42,126
3,430
3,567

Dynamic viscosity
(cP)
37,719
35,139
42,030
3,416
3,376

5,053
6,061

4,590
5,525

5,087

6,895

7,748

8,609

5,883

8,140

12,554

19,596

1,144

1,025

density
(g/cm3)
1,109
1,0568
0,99772
1,0092
0,94635
0,93815
0,93029
0,93419

1,4220
1,4394
1,4418
1,4155
1,4176
1,4242
1,4208
1,4212

Dielectric
functionb
0,2026
0,2084
0,2092
0,2004
0,2011
0,2034
0,2022
0,2024

0,91169
0,9024
0,90057
0,93378
0,92774
0,9172
0,91337

1,4271
1,4257
1,4258
1,4176
1,4237
1,4214
1,4214

0,2043
0,2039
0,2039
0,2011
0,2032
0,2024
0,2024

0,90826

1,4238

0,2032

1,35556
1,11406
1,1112
1,09854
1,38367
1,4727
1,5609
0,94275
0,89565

1,3821
1,3903
1,3868
1,3890
1,3522
1,3354
1,3298
1,4032
1,4044

0,1888
0,1917
0,1905
0,1913
0,1779
0,1715
0,1694
0,1962
0,1966

2S

2.2032 0.1762 0.8322 2.87652 1. with some values unusually high in those cases where the π* values are negative.1.37 1.4t.938 9. they are also affected for α the errors in π* determinations.3585 2.7 9.4437 1.7068 1.484 4.1. as α values were estimated from ET(30) and π*.31 0.60 0.2 4.88 0.506 3.4 4i.5511 1.4.07 2.2212 2.17 0.3F 4t.810 2.2 3i.06 39.77 1.4 4.2.4463 1. In general. and cover a wide range of hydrogen-bond donor abilities.316 3.89516 1.21 0. with several superimposed bands. they are higher for alcohols (diethers) than for triethers.23 50.6867 3. from weak to very strong.3476 1.1777 (ε–1)/(2ε+1) b (n2–1)/(2n2+1) Comment on π* and α values: π* values display a somewhat erratic behaviour.3558 0.04 0.1.4748 2.0774 2.4281 0.08 52.15 0.2-Trifluoroethanol THF: tetrahydrofuran Tol: Toluene W: Water 3S .39 0.8 0.3F 3F.175 4. List of solvent names abbreviations used in Figures 1.1886 1.3816 0.41 0. the α values are in line with the observations made for ET(30). but there are some exceptions. and point to the difficult measurement of π* for these systems.15 0. and also higher for those compounds bearing fluoroalkyl substituents.44 0.06 60. and in particular some compounds have negative values.4 4.00 0.39 3. these values are not reasonable.865 1.4 4t.15 0.36 0.3F 3F.23 45.1.2.16 -0.235 4.3F 3F. 6.4 3i.330 1.1.783 0.2. since the UV spectrum of p-NO2-anisole showed a complex structure.2017 3.1. normally associated to a very low polarity (as is the case of perfluoroalkanes).24 0.81 0. 7 Ace: Acetone ACN: Acetonitrile BuOH: n-Butanol DCM: Dichloromethane DE: Diethylether DMF: Dimethylformamide DMSO: Dimethylsulfoxide EA: Ethyl acetate EC: Diethyl carbonate EG: Ethylene glycol Fur: Furan Gly: Glycerol Hx: n-Hexane HxOH: n-Hexanol MeOH: Methanol NM: Nitromethane Naph: Naphtalene OcOH: n-Octanol PCB: Pentachlorobenzene PhOH: Phenol PrOH: n-Propanol p-Xyl: p-Xylene TAC: Triacetin TFE: 2.04 48. Obviously.3516 0.4 4t.4 4i.16 0.39 49.14 0.7561 2.4.1535 1.55 0.3379 2.2.4 3i.8724 2.2.3552 2.3F a 0.4135 0.2.1.1.139 0.68 0.266 0.69 0. Otherwise.42 -0.10 0.2871 1.86 63. 5.4473 0.55 0.2.16 0.3F 4.57 63.24 0.19 42.2 4i.18 61.04 0.57 1.09 0.2266 1.669 0.23 47. which is totally unusual.721 2.744 12. Obviously.8437 1.78 51.87 51.0456 1.4191 0.1609 199 217 210 218 222 234 211 244 226 241 270 180 185 207 178 171 208 37.268 13.0672 1.86358 1.8035 1.93 54.1810 3.4232 4.12 0.1998 4.91 1.4237 1.046 2. in some cases it was impossible even to have an estimation of π*. 4.1862 0.3748 1. In fact.32 77.151 2.184 4.36 0.4262 2.

710 333.400 0.176 0.28 373.75 4.869 8.4 4.944 353.49 37.549 7. T (K) Solvent 1.0.80 60.4t 4.43 363.0.0.46 2.4t 3i.620 1.030 0.153 9.680 1.571 0.285 298.700 0.495 4.09 26.359 323.273 6.084 0.721 2.275 0.15 35.15 4.1.320 3.175 0.130 1.138 0.479 6.480 0.24 36.4t 1.611 5.52 8.199 19.260 2.121 0.15 0.399 1.879 3.76 50.018 0.15 13.24 16.105 0. Kirkwood function vs.546 0.0.3i 3F.442 1.238 343.030 2. Dielectric function plot for a series of common organic solvents and glycerol-derived solvents.060 0.885 2.09 1.055 0.560 13.71 22.15 1.98 10.1.Table 2S. 4S .510 0.15 2.678 11.96 Figure 1S.420 0.0. Experimental vapour pressures P* (mm Hg) of some representative glycerol-based solvents at different temperatures.78 29.3F 3F.15 8.061 13.11 23.311 0.429 303.811 4.3F 293.15 0.751 0.640 313.24 17.270 0.15 0.15 22.335 0.

001. At least three readings of the flow time with variations not exceeding ±0. Dielectric permittivity data were obtained with a WTW (DM01) dipolmeter (Kahlsico) which works at 2 MHz by a beat heterodyne method. Concentration of dyes was between 1·10–2 and 4·10–2 mg·mL–1 for Dimroth dye’s (ET(30) determination) and between 2·10–1 and 6·10–1 mg·mL–1 for p-nitroanisole (π* determination).410 Dielectric permittivity and dipole moment.7 32. the result was 5. certain quantity of solvent (5 g) was dissolved in 20 mL of dry methanol (Hydranal®). Refractive index was determined using a Zeiss refractometer with temperature controlled exchangeable prisms and a sodium lamp as light source.Experimental procedures for the physico-chemical properties measurements Solvatochromic parameters A double beam photometer model Unicam UV-4 was used to determine the spectroscopic parameters. by means of the equation 5S . Hydrophobicity. and then was titrated with Karl-Fisher reagent. the result was 171 mg/L.254 mg H2O/mL reagent.1 nm. Sometimes it was necessary to use sonication to improve the solution process. The cell path was 1 cm. with a resolution of 0. The determination of water in solvents under saturated conditions was carried out after washing those solvents with water during 30 min.4 ν 10 34. The sample holding cells are provided with a water jacket for maintaining the constant temperature of the liquid being measured. was estimated using the Ghose and Crippen atom contribution method through the ΔLogP98 refinement. The viscosities were calculated from the average flow time. First of all exact concentration of Karl–Fisher reagent (Iodine–sulfur dioxide–pyridine. To determine the quantity of water in solvents. refraction indices and densities through the Onsager’s equation: 1S μ2 = ( )( 9kTM ε − n 2 2ε + n 2 2 4π N A ρ ε n2 + 2 ( ) ) where k = Boltzman’s constant T = temperature in ºK M = molar mass NA = Avogadro’s number ρ = density n = refractive index ε = dielectric permittivity Refraction index. Hydrophobicity and water content. solvents were kept in closed bottles under air atmosphere during 6 months. The uncertainty is estimated in ±0. t. using Zn(AcO)2·2H2O (16. The scan speed was 30 nm·min–1.2S To determine water content in solvents under storage conditions.42 % of water) (200 mg) dissolved in 20 mL of dry methanol (Hydranal®. a Karl–Fisher closed volumetric system was used. Spectra were registered between 400 and 800 nm for ET(30) parameter and between 200 and 400 nm for π*.5 mL.17 2. and their volume was 1. measured as logP values.1 s were taken for each liquid. The average dipole moment μ 2 1 2 was calculated from measured dielectric permittivities. The uncertainty is estimated in ± 0. After that three blank measures were done to determine the quantity of water in methanol dry (Hydranal®). from Fluka). ET 30 2.00002. Ubbelohde viscometers (Schott) of relatively long flow times (100 s to 600 s) were used to minimize the kinetic energy corrections. To determine the quantity of water in glycerolbased solvents. from Fluka) was determined. Viscosities.859 10 ν ν 30 30.

61 ºC and ΔHf = 28.cm-3. 64. 1999.00002 g. Crippen. Ghose..pressure cell which was joined to a stainless steel pipe. Viswanadhan and J. Manometer lectures were read with a resolution of 0. Chem. 1971. The Texas A&M University System: College Station. Boiling point temperatures were assigned at offset point of the scanning. K.p. 883. 39.6 ºC. Each liquid were degassed by magnetic stirring under its own vapour pressure and the vapour + air pumped away periodically. covering a range of 188–290 ºC in b. filled with around 10–12 cm3 of liquid degassed was connected to the manometer system.15 K and sample density is calculated from the vibration period with un uncertainty of ±0.005% of full scale.. A and B are the viscometers constants that were determined by using values from literature. (b) S. Wildman and G. Vapour pressures. L. Chem. Comput. Differential scanning calorimetry (DSC) was carried out using Indium as reference (m. 1486. and then the liquid sample was introduced by gravity into the vapour. respectively. 868. 3S. Trans. 3762. Faraday Soc. Inf. based on measurements made on glycerol and three glycerol derivatives. 0–100 torr. Am. J. The vapour pressure measurements were performed by a static method. 68. 1968. 102. The densimeter operates at 298. A glass cell with PTFE junction. Wendoloski. Chem. 1998. previously evacuated. Boiling point. Soc. Dynamic viscosity was calculated according to the equation η = νρ where ν and ρ are the kinematic viscosity and the density. To prevent condensation effects the temperature of the manometers was maintained at 396. (a) A. N. TRC–Thermodynamic Tables–Non Hydrocarbons. J. 2S. TX. The pressure was measured with a set of three Barocell 659 capacitance manometers (Edwards absolute models) each one with a different pressure range (0–10 torr.s-1. 0–1000 torr).71 J·g–1) in a DSC-MDSC TA Instruments 2910. The uncertainty in the kinematic viscosity measurements is not worse than ±2x10-9 m2. K. 4S. N. Three different viscometers were used during the course of this investigation. the most important is the replacement of the mercury manometer by electronic gauges. M. Marsh. 3S The viscometer was held in a water bath whose temperature was controlled to within ±10 mK. Thermodynamic Research Center. The apparatus is similar to that of Marsh4S except for some experimental details. The temperature of the liquid sample was measured by means of a digital Pt 100 thermometer with an uncertainty within ±1 mK. The standard error of the method was estimated in 1. J. Chem. J. References 1S. It was used samples between 1 and 2 mg in aluminium perforated capsules with a heating rate of 20ºC·min–1. 5030. A densimeter (Anton Paar DMA 60/DMA 602) was used for density measurements. Onsager. 6S . B ν = At −   t where ν is the kinematic viscosity.15 ºK. V. Densities. p.p = 156. A. A. Phys. 1936..

4394 33. 1H). 1174.485. 3. 3.469.334 (d. 0. 70.487. 3. 3. 2873.a.131 (t.977. δ ppm.585.553 42. 3. 2976. p.4418 0.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 45.872. δ ppm. 63.580.890 (t.0 Structure O OH 1874-62-0 1.114.565.351 C-RMN 1120. 69. 3390 FT-IR 120. 3.871 (sa.381. 2H). 1H) 13 14. 0. 1. 1H) 13 13.68 3.783 (sa.496 (dd.328 (m.39 0.344 (s.773. 1.841 (sa.a.2092 π* ε le c) f(kirkwoo 0.450. 2868. 1H) 59. 13C-RMN (CDCl3. 3.449.031 (sa.011 0. 3.821 (sa. 3410 FT-IR 148.802 (m. 3.451. η (cP).467.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 56. 1H). b.433. p. 3. 3.2026 π* ε le c) f(kirkwoo 0. 0.371.02 0.03 0.497.502.86 1.88 32. 1H).719 43. 3.356 (d.593 (dd. 2966. 1H) 13 58. 1186.691 C-RMN 1114.750-3.680.338.523 (q. FT-IR (cm-1).030 41.486.27 9.9996 Miscib f(dielectri ∆ 0. 2H).912 (sa.375. 1. 2941. 4. 3. 1.684.747 7S . 1160.879-3943 (m.795.9977 n.71 3. 3.2-propanediol 1. 62. 4.4664 α Name Code CAS d) OH 3-ethoxy-1. 3.088 (sa. 1. 3H).86 21. 1 H-RMN 3. 1H) 3.931. 2874.096. 70. 73.5 Polarity Vaporization Polarizability Hydrophobicity Others 0. log P Miscib f(dielectri ∆ 0. 1.366.1090 n. 0. 2923. 3. 4H). Full characterization of the glycerol-derived solvents prepared 1 H-RMN (CDCl3. 1H).126 µ b.553 (m.587. 1H). 2H). log P 0.95 0. 66. P (mm Hg).775 (sa.98 10. 4. 6H). 3.561. 18.139 45. 3. 1. 1H).430 1 H-RMN (m.362.799.408.0568 n.288.4. 3H).68 12.23 0. 3.1 9. 3.078. log P 0.422.589 (dd.1 Structure O O 623-69-8 2.a.773 (m. 3. 0.0. 3.3-dimethoxy-2-propanol 1.878 37.2-propanediol 4.500.6 Polarity Vaporization Polarizability Hydrophobicity Others 34.551.0 Structure O OH 624-52-2 0.Table 3S. ∆H (kJ·mol-1). ν (cSt).6508 Miscib f(dielectri ∆ 0. 71.00 49. 3.353. 3.730.854. (ºC). 3. 3.11 0. 1.50 45. 1H).83 1. 34.416 222 1. 3. 1H).251 µ b. 2H). 63.3291 42.9 10. 73. 3.294 (s.148 249 1.3. 3. 63. 3.73 10.2-propanediol 2.480.623 35. H O (mg·g-1). 2932. 400 MHz).77 18.851 C-RMN 1111. 1 H-RMN 3. 2H).2084 π* ε le c) f(kirkwoo 0. 3.2 10.674.132.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 49.69 3.87 (dd. 3.0. 2. p.468 (c.4220 µ b.07 39. 3. 3H).4425 α Name Code CAS d) Name Code CAS 1 H-RMN 13 C-RMN OH 1.00 56. 3. 2H).433 (ddd. 1H). 3.91 0.4608 α Name Code CAS d) OH 3-n-butoxy-1. 1H).424 221 1. -3 ρ (g·cm ) OH 3-methoxy-1.415.660. 2974. p. 71.0.00 45. 1H). 400 MHz). 3399 FT-IR 106.0. 70.0 Structure O OH 623-39-2 3. Elemental analysis (%).5 Polarity Vaporization Polarizability Hydrophobicity Others 0. μ (D).

519 (sa. 1.1 9. 6H).562. 2957. log P Miscib f(dielectri ∆ 0.593. 0.48 2. 1. 69.49 2.98 Theoretical H 10. p.5 10. 3.131.897. 2923. 1.00 50.2011 π* ε le c) f(kirkwoo 0.219.376 38.813.923.491 (m.9 11. 78.310. 2876. 3H). 19.890 (d. µ b. 1. 1.9 Polarity Vaporization Polarizability Hydrophobicity Others 0.3938 α Name Code CAS d) Name 1-tert-butoxy-3-methoxy-2-propanol Structure OH 8S . 3.341 (s.0092 n. 1. log P 0.224.385-3.47 n. 3.169.4443 1.1 Structure O O 13021-51-7 0.329. 4H).553 (q. 1.646.854.1 11. 1H). 3.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 56. 3H). 1H) 13 13. 3. 3.18 29.59 0.23 11.4176 0. 1. 1.59 0. 58.292. 4H). µ b.1 Structure O O 635315-52-5 0. 3.881. 3. 3.72 µ ε 1191. p. 1H) 13 19.077.430 1. 1H) 13 21.578.07 Polarity 0.798 C-RMN 1114.487 (m.499. 69. 0.891 (t.250. 3440 120.4208 0.39 0. log P Miscib f(dielectri ∆ 0. 2874.402-3. p.547. 6H). 1126.011. 69. log P Miscib f(dielectri ∆ 0. 3. 3. 1. 2.826. 3.4242 0.00 58.745 (sa. 58.830. 1460.455 (m.5 Polarity Vaporization Polarizability Hydrophobicity Others 0. 1H). 1.88 32.0. 1 H-RMN 2H).4155 b. 3H).a.0 Polarity Vaporization Polarizability Hydrophobicity Others 0.231 (dd. 1. 3. 2H).194. 31.3993 α Name Code CAS d) OH 1-iso-butoxy-3-methoxy-2-propanol 4i.805.4103 α 1 H-RMN d) OH 1-n-butoxy-3-methoxy-2-propanol 4. 73.264 C-RMN 1195.23 11.561 50.424 208 1. 3.9382 0.960.863.55 n. 2. 3. 73.00 56.929 170 3.861 3.817 C-RMN 1075. 2969.34 0.2034 π* ε le c) f(kirkwoo 0. 3.364-3.353 200 1. 3.949.214.367 (m. 71. 3.061.362 (s. 1. 3.a. 1H).21 0. 3. 2870. 2973.975 (q. 1. 71. 1. 1H). 2929.348.61 π* α 0. 3.846. 1. 1H).73 10.92 n. 0.00 59. 0.878.274. 71. 3.930 (m. 1.FT-IR m/z C 49.9303 0.a.0. 0. p. 3437 FT-IR 162.27 n. 1.96 6. 1.922.068.416 0.889 (m. 2870. 59.567 µ b. 1H).883. 69. 2926.a. 3446 FT-IR 162.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 59.0.904.897. 1 H-RMN 3.945 n.508 188 1.208. 6H).623 (sa.62 6. 71.2004 le c) f(kirkwoo d) 0. 2. 3460 FT-IR 148. 3.99 3. 2971.937.483.608 (q.a.796.880.a. 1. 0.73 0.916.1 CAS 53146-34-2 OH Structure O O 1.931 (q.147 (d. 73. 3. Name Code 1-iso-propoxy-3-methoxy-2-propanol 3i.a.71 7.9464 0.059.536. 0.6007 n.a. 2930.913. 1.9 Vaporization Polarizability Hydrophobicity Others 2.672.2022 π* ε le c) f(kirkwoo 0.18 29. 3.873.95 0.519.963 30.1 elemental analysis Experimental elemental analysis O F C H O F 39.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 59.7376 n.5911 Miscib f(dielectri ∆ 12.1352 3.410.49 2. 2H). 28. 58.776.381 (s.891.

2869.8 Polarity Vaporization Polarizability Hydrophobicity Others 0. 69.562.a.187.330.0. log P f(dielectri ∆ 1.816.379 (m. 69. 73.530. 1 H-RMN 1.229. 1462. 0.295. 59. 223 5.36 44. 71. 2H).9084 n. 3.1 13021-53-9 1.71 0. 1.642 68.193. 1. 4H).2043 π* ε Name Code CAS c) α Name Code 0. log P f(dielectri ∆ 0. 6H). 9H).467 (m. 62.574 (q. 3. 31.857. 1.372 (s. 1. 72.180. 3452 FT-IR 204.520.884. 69. 1. 1. 3.582. 9H). 1. 1. 1126.323.805.4212 0. 1116. 62.820.a.327-3. 1. 3.23 0.65 25.93 n.7 11.902 (t.7 5. 1364.147 (d.875.8 11.12 11.540.0. 2931. 1463.36 ε 4t.a. 1.492 (m.5 Polarity Vaporization Polarizability Hydrophobicity Others 6.a. 2956.558.595 (d. 55.919 (m. 2866.845.891.342.3-di-n-butoxy-2-propanol O O 4. 2931. 1H) 27.801.149. 1.345. 4H). 2H).360.Code CAS 1 H-RMN 13 C-RMN FT-IR m/z C 59.9342 0. n.547.286.09 5.7 Polarity Vaporization Polarizability Hydrophobicity Others 9S .388 (m.000 1078. 1H) 13 13. 1.501.590 n. 1.132.312. 19.4 Name Code OH O O Structure 53146-43-3 CAS 0.540. 3. 1H).537. 1374.821. 1.346.45 2.2024 le c) f(kirkwoo d) 0.3402 b.571 (q. 4H). 73. 1. 3.a. 4. 2953. 8H). 71.0.18 Polarity 0. 1.859 (m.4 OH O O Structure CAS 1 H-RMN 13 C-RMN FT-IR m/z C 64.554. 1.313. 2. 1461. 2866.538.3945 0. 2924.788.933 (q. 31.a. π* ε 1 H-RMN c) α 0. 0. 3. 3440 162.16 n. p.0663 µ b.493.186.907.577.608 (q.331. 3H). 1.585 (sa.3779 0.578 (sa. 71.630 (sa. log P Miscib f(dielectri ∆ 6. 1.912 (t.a. 1. 1114. 3. 31.0 Theoretical elemental analysis Experimental elemental analysis H O F C H O F 11.0.350. 69. 1. 1H). 2971. 3. 2H). 1. 71.379-3.525 0. p. 0. 2. 1465.872. 0. 0. 1.10 f(kirkwoo d) 0. 71. 3. 2. 73.180 (s.9117 0.510. 1.895. 6H).369. 3.1H).808. 1H).053 n.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64. 19.349.304.84 23.23 π* α Theoretical H 11.030 3-n-butoxy-1-tert-butoxy-2-propanol 4t.548.837.420 1-n-butoxy-3-iso-propoxy-2-propanol 3i. 2H).893. 3H).387 (m.77 f(kirkwoo d) 0.665. 3H).71 0.564 (q.00 64. 3.381-3. 2871. 2. 3.43 n.0 11.032. 3. OH 1.4 Structure 2216-77-5 0.873 1114.00 58.a.a. 19. 3448 FT-IR 190.503.393 248 1. 1.472 (m.359 195 1.4 11.834. 1.1 elemental analysis Experimental elemental analysis O F C H O F 29. 1.368. 2.585.061 0.479.00 64.167 (s. 71.042. 1.49 0. 6H). 1. 3457 204. 56.67 42910-65-6 0.4639 µ b.479 (m.592. 0.84 23.822. 27.294.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63. 2965. 2933. 1. 1.612 n.67 11.00 63.871 (m.856-3.49 0.518.882. 1.791 C-RMN 1078. 1H). 3.909 (t.603. 1. p.018 C-RMN 1075.2 Vaporization Polarizability Hydrophobicity Others n. 3. 1H) 13. 3. 1.44 µ 0. 3. 3H). 3. 1.4271 2.59 0.865.557.324-3. 69. 3. 1.919.386. 1H) 13 13.179. 3. 2. 1. 3. 3.

0.131.5 Polarity Vaporization Polarizability Hydrophobicity Others 0.913. 1. 1. 1. 71.9338 OH Structure O O 0.589.655.929 (sa.681. 71.902.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64.919 (t. 2931. 1. Name Code 1-n-butoxy-3-ethoxy-2-propanol 4.973. 69. 2. 3.821. 1.580 (q.a. 0. 1.854.2039 π* ε Name Code CAS c) α 0. 21.547.304.376.0. 78. 69.1H) 13 13.0 Polarity Vaporization Polarizability Hydrophobicity Others 0.890.395 (m.339. 71.177 (s.210 (t. 1H). 2868. log P f(dielectri ∆ 0.583. 3.396 (m. 0.386 26.931 (sa. 3.302. 3.4 Structure 113560-35-3 0.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 59. 3.920 (t.208 (t. 3.340. 3441 FT-IR 176. 1. 4H). 6H). 1. 3. 1.564. 1.22 2. log P f(dielectri ∆ 0.0.425.943 C-RMN 1076. 0. p. p. p.00 59. p.46 2. 2H).23 11.199.535 (m.200 (t. 3.357.338.563.900. 1. 1. 2929.507. ∆ 0.146 (d.21 f(kirkwoo d) 0. 3.a.646.235.84 23.561.359. 3.01 n.0864 µ b. 71. 0.593.36 f(kirkwoo d) 0. 2973.558. 3437 FT-IR 185. 1460.881. 1H).500 (m. 55.191. 3. 38.a. 1. 1 1.143.544 (sa.378.498 (m. 3H). 69.524.458-3. µ b.815. 1126. 71. 1. 3.9294 n. 0.4237 1. 2868.3672 n.332.2039 1.183. 1. 14. 3452 FT-IR 204. 1H) 10S .96 6. 1. 2956. 1H).609 (q.548.511.105 OH 3-n-butoxy-1-iso-butoxy-2-propanol O O 4i. 1.2011 π* ε 1 H-RMN c) α 0. 1465.885 (m. 3H).0 11. 2H).885 (m. n. 1.883.00 64.871.149 n.0. 1. 1H) 13 14. 2. 1-tert-butoxy-3-ethoxy-2-propanol 4t.218 (d. 9H). 66.417.9024 0.6689 n. 31.175.257 229 1.163 ε f(kirkwoo d) b.796.407-3. 1. 1379.3944 0.18 n.49 0. 1. 3H).75 α 0. 6H). 3. 4H). 2H).541 187 1.403-3.a. 2931.59 0. log P f(dielectri ∆ 0.4176 0.873. 1. 19. µ b.804.578.a. 1.45 2.4049 n. 1H) 13 13. 2. 3. 1.a.45 2.840.888.a. 1H).a.191.177.39 π* 0.3676 230 44.528.9006 OH Structure O O 1.1 11. 3.4840 n.555 (sa. 1.4258 1.571 (d.18 29. 1.541 (c.a.201. 2H).259 µ 5. 1. 28. 1H). 2869. 1.193.2 OH Structure O O 42910-64-5 1.820-3.332-3.165. 71.459 220 n. 1. 1.2032 π* ε 1 H-RMN c) α Name Code CAS 1 H-RMN 0. 71.439 (c.75 7. 2H).9277 n.4 11.582 (q. 1. 71. 0.00 61.2 CAS 13021-50-6 0. 3. 1. 1117.a.a. 3.565. 6H). 19.57 5. n. 1. Name Code 1-ethoxy-3-iso-propoxy-2-propanol 3i. 3. 0.322. 3.2 CAS 13021-52-8 0.510. 1.a. 3.904 (m.4257 f(dielectri c) log P 0.219. 1.0. 2958.547. H-RMN 2H). 1115.44 27. 66. 2. 19.377. 0. 3. 3.320.67 11. 2.69 n.50 f(kirkwoo d) 0. 0.838.33 11.277 C-RMN 1077.488. 3. 1.545 (m.401. 1.23 0.a. 3H). 69. 1H). 2H).889 (d. 8H).599 44.50 1. 1.174.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 61.608 (s. 31.a. 3H).201.818 C-RMN 1077.762.0.527.9 Polarity Vaporization Polarizability Hydrophobicity Others 0. 1.5 n.

1. 1. 1116.a.a. 1364.3 Polarity Vaporization Polarizability Hydrophobicity Others 0. 1371.899.208 (d. 3.126.3846 n. 1. 1468.388-3. 69.860. 71. 3. 3455 176.892 (m.475 (ddd. 2H). 3450 FT-IR 176. 71. 1459. n. 3.a.997. n.396.0 11. 62.41 µ 0.a. 2974.8 n.71 5.50 2.134 (d.317 204 1.86 0. 1H). 2929. Name Code 1. 1. 3450 FT-IR 176.301.638 (sa.965 n. 1.a.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63.579 (q. 3. 3. 2864.851. 71.44 27.314 224 1. 2927. 2H).320.62 0. 27.583 (sa. 1.338.614 (q.123. 1467.4639 µ b. 2962.526.44 Polarity 0.348. 3.792. 2869. 6H). 3.08 f(kirkwoo 0. 6H).918 (t. f(kirkwoo d) 0.00 61.a. 3. 3.614 n. 53.987. 69.2 Polarity Vaporization Polarizability Hydrophobicity Others 0.394 (m. 71.813.605.842. 3. 1. 69. 1.1 elemental analysis Experimental elemental analysis O F C H O F 27.118.d 0.00 63.881. 1118.4238 1. 66. 0.6890 n.d 1-n-butoxy-3-iso-propoxy-2-propanol 4. 1. 40. 3.2032 π* ε 1 H-RMN c) α 0. 1.152 (d.635 (sa. 6H).8615 n.518 (m. 1. p.0.23 0. 3.948 (q.909. 3.161.411.23 0.839. 1. log P f(dielectri ∆ 0.13 C-RMN FT-IR m/z C 61. 0.177. 1. 3.859. 3.a.357.a.904. 1.330 214 1.a.32 0.568. 69. 3. 1H) 13 21. 66.962.00 61. 3.a. 2870. 3. 3.534. 3.931. 3.825.46 2.9172 n.00 61. 3.331. 3.682 1076.4214 0. µ b. 3. 6H).388.663.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 61.a. 1.46 n.9083 11S . p.595.0. 3. p. 4H).895.25 5. 1H).504.23 0.480 n. 3. 3. µ b. 69.3773 n.825 C-RMN 1071. 2. n.1 11.6 Polarity Vaporization Polarizability Hydrophobicity Others n. 71.9134 OH Structure O O 1. 0. 2H). 2972.a. 1.9495 n.816 C-RMN 1076. 3. 2. 31. 1H).a. 1120.68 120.d π* ε 1 H-RMN c) α n. 3. n. 21. log P f(dielectri ∆ 1. 1 H-RMN 1H).694.12 11. 2956.580.935.876 (d.741.278 C-RMN 1076.545.3i CAS 13021-54-0 0.848.808. 71.735. 2. 3433 FT-IR 290.86 n. 70.997 n.a. 3.23 0.33 11.a. 1370. 12H). 1. 1129. 2871. 3.562. 28. 3.921. 69.5 11. 1H) 13 14. 1. n.1 11.549. log P f(dielectri ∆ 5. 3. 3H).996. 40.564.440.a.386-3.a.411. 3. 3.826.865.3i Name Code OH O O Structure 53146-43-3 CAS 0.863 (q.2 Vaporization Polarizability Hydrophobicity Others 2.892. 1.509.783. b.36 ε 14. 71.372.307.011.599. 78.4214 0.463.875. log P f(dielectri ∆ n.229.0 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 61. 1. 0.0.3840 0.531 (m. 1.a.451.2024 c) f(kirkwoo d) 0. 1.918 (q. 2H).553.33 π* α Theoretical H 11. 1. 1H) 13 13.33 11.178. 2927. 0. OH 1-iso-butoxy-3-ethoxy-2-propanol 4i.595 (q.376. 3H).65 25. 18.a.40 f(kirkwoo d) 0. 3.2024 π* ε Name Code CAS c) α 0. 73. 19. 0.880.2 Structure O O 382601-20-9 (patent uses) 0. 202 n.583.137. 1.196 (t.3-di-iso-propoxy-2-propanol 3i.191.638.44 27. 1H). 3. p.

1371. 3442 FT-IR 290.146 (d.452.493. 3. n. 3. 3. 3. 3. (68.156 (d.410 (m. 3. 3.1 7. H-RMN 1.0 11. OH Structure O O 0. 3.577.623.130.475.592. 0. 1364. 3.576.65 25.595 (sa. p.8 Polarity Vaporization Polarizability Hydrophobicity Others 0. 1H).612 (sa. 3. 72.169 (s.212 (d.a. 3.1426 µ b. 3. 2. 62. 1.a.691. 2H).614. Name Code 1-iso-butoxy-3-iso-propoxy-2-propanol 4i.2.355. 3.607. 3.447. 13 C-RMN 128.648.668.318. 6. 1.653.644.a. 2. 2870. µ b.7 11. 1.a. 3. log P f(dielectri ∆ 0. 2877. 2H).148. log P f(dielectri ∆ 0. 1. 3.797. 3. 2869.561.431. 1. Name Code 1-iso-propoxy-3-(2. 3.23 0. 1. 1H). 3. 3.a.2-trifluoroethoxy)-2-propanol 4.901.658. 2H). 3438 FT-IR 216. π* ε c) α 0.459. 3. 71. 1. n. 3. 202 n.44 6.814.705. 1. p.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63.425.44 n. 72. 3. n. H-RMN 3. 0.693. 3.486.578 (q.a. 3.59 3.a.860. 3.706. 3.620 (q.885.a.393 (m.620.2. 3. 1.37 n.a. 1. n.708.a. 1.510 (ddd.65 25.3F CAS n.12 11.12 11.a. 68.546.680.860. 1.00 63.388-3. 6H).169 (c)). n.a.0.577. 3. 3.681.336. 2H). 1195.717 (ddd.213.2-trifluoroethoxy)-2-propanol 3i. 2H).561. 3. 3.607 (q.a. 3.592.882 (d. 3. 3. 1280. 2H). 1125.525. 1. log P f(dielectri ∆ 0. 68. 1H) 13 19.300. 3.864.414-3.3i CAS 286957-56-0 OH Structure O O 1.059.788.508.082. 2H).895 0. 3.743.195.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63. 1.471.3556 n.544.143. 2975. 21. 3.03 n.54 f(kirkwoo d) Name Code 1-n-butoxy-3-(2. 1468. 3. 3.846. 122. 1.986 37. 3.805 (m. 1 3. 6H). 3.634.a. 47. 3. 3.831.3i CAS n.a. 69.591 (sa.3821 1. 1H). 71.897 (m.483 (ddd. 1.887.401. 1369.00 62. 3. 3. 1H).561.638. 1. 1. 3. 3.874.921 (t.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 44.916 (c.a. 1H) 21. 1H).223. 69.124 C-RMN 1075. 9H).785.573.851. 3.001 (c)) 19 -74.447. 2927.a.09 n. 1H). 3. 2933.a.23 0.21 n. 3. 1H) 13 21. 68.389. π* ε c) α 0.903. 46.3F CAS n.a. 1.3270 n.408.130.0.1H). 3.413. 71.145 (d. 3873.a. 27. 0. 215 n.36 44.d) Name Code 1-tert-butoxy-3-iso-propoxy-2-propanol 4t.690 C-RMN 1073. 1H). 0. 28. 3.847. p.446. OH F F Structure O O F 1. 12S .0665 n. 1. 2H).922 (m.4H).865. 6H).5 Polarity Vaporization Polarizability Hydrophobicity Others 0. 2. 69. 1.629. 73.0.830.141.28 (t) F-RMN 1152.337.895.29 f(kirkwoo d) n. 2927.a.a. (119. 3.2 26.844. 69.607 (q.a.71 11. µ b.881. 1467. 1. 3. 2. 78.497 (m.0. 4H).155.423.47 f(kirkwoo d) n.62 n. n.330-3.0 Polarity Vaporization Polarizability Hydrophobicity Others 0.20 26.4399 OH Structure O F O 0. 6H). 3.591. 3H).120.914 (q.57 n. 1 H-RMN 3. 2971. 3.a. 125.562.587 (sa. 2967. 1. 1.499. 3.730.546. 69.361 176 5.2H). 1.716 (ddd. 3436 FT-IR 290.99 22.500 (m. 3. 3.374. n. 69.087 1.1888 π* ε 1 H-RMN c) α 1 0.

73. 3.928.3476 7.716 (ddd.a.919 (c.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 46.1112 Name Code 1-iso-butoxy-3-(2. 3.181 (c)). 122.921.654.85 24. 3. 19. 3. 2932. 3473 256.197 45.61 f(kirkwoo d) n. 3. 69. 128. 128.868.514. (c.314 (c)). 3.0 Theoretical elemental analysis Experimental elemental analysis 13S .214.a.3868 1.641.2.223. (68. 69.79 F OH F F Structure O O F 2.44 20. 3432 FT-IR 230. 73. 78.649. 1466.995.897.6081 µ b.7450 µ b. 2H). 3. log P f(dielectri ∆ 0.3 24. 3. 1278.237. 3.896. 69. 69.2-trifluoroethoxy)-2-propanol 4i. 2929.4 Polarity Vaporization Polarizability Hydrophobicity Others 0.625.0. 2H) 27. 2H). 1. 3.a. 69. 122. 0. 3.460.235 57. 71. 2956. 3. 1461.1905 π* ε 1 H-RMN c) α 0.701. 2957.5 24.430.0.669. 68. 68. 9H). 68. 3.0985 n. 1. 1.693. 3.933. 1466. 69.53 11.556.942. 3.a. 1H).015 (c)) 19 -74. 13 C-RMN 128.665. 3. 3. log P f(dielectri ∆ 0. 1278. 3. C-RMN 122. 3.947.968.647. 3. 3.872.85 24.716.641. 0.918 (c. 3. 1278.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 46.894.3F CAS n. 3.218.95 7.431 205 n.646.805. 1.853. (119.419. 13 C-RMN 125.081.218. 73. 3.036 (c)) 19 -74.3. 0.44 20. 3.505.3903 1.263. 3.57 10.972 (q.a. 3. 2874.854. 3. 1H). 3.070 (c)) 19 -74. 3.328 (m) 1157. 69. 3. OH F F Structure O O F 0.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 46.382. 0. 3. 1H).231 (dd.691. 73.071. p.000 (c)) -74.297.347. 1. 3. 1H). (68. 3.28 (t) F-RMN 1161.727 (ddd.968.889.703.1141 n.007. 6H).95 7.2-trifluoroethoxy)-2-propanol 3F.850.3F CAS 691-26-9 C-RMN F-RMN FT-IR m/z 19 f(kirkwoo Name Code H-RMN 13 0.736. 2930. 3.a. 3. 3. 1H) 19.838. 2.302 (119.9 7.0.397.2.85 24. 2H).480. 3. 125.204. p. 3.359. 3.442 (ddd. n.1913 π* ε 1 H-RMN c) α 1 d) 1. 3.232 (c)).553.1917 π* ε 13 c) α 0. 1.77 n.229 (c)). 4.013 56.4301 Name Code 1-tert-butoxy-3-(2. 2H). (68.076. 3. 2870.843.463 (m.855.5 7.76 46.3-bis(2.727. 125.60 3.943. 3.206. 68. 1. 3. 3. 3.905 (m. 3.76 46. 71.a. 68. 3.678. 125. 73. 2H).2-trifluoroethoxy)-2-propanol 4t.3890 1.598 (sa. 3. n.5 Polarity Vaporization Polarizability Hydrophobicity Others 0. 68.a.292. 3. 8.a.166.303.912 (c.507 (sa. 68. 3440 FT-IR 230.a.3F CAS n. 2872.408. log P f(dielectri ∆ 0.894 (d. 1. 62. 1276.44 20.465. 3. 3. 3. 4.616.872. OH F F Structure O O F 1.739 (ddd.29 (m) F-RMN 1159. 122.6 Polarity Vaporization Polarizability Hydrophobicity Others 0.40 n. 1. 128.1 7. 4H).258.446 210 n. 3. 3. 4H).714. 3. 0.021 (m.567 (sa.875.84 10. (119.656.890. 1H) 13. 3.891. 2971.877.70 f(kirkwoo d) 1.4287 1. 3.57 3.748 µ b.28 (t) F-RMN 1152. 3. 3. 2H). 71.875.956. 3.640.205.959. 0. 2938.313.4359 1.642 199 1.981 (q.704.181 (s.79 n.76 47.679. 69.375.609 0.267.670. 2.692. 3441 FT-IR 230.664. 2891.a. 68. 1460.894. 2H).224.603. p. 3. 1H) (68.916.3 24.681. 3. 3. 3. 3.822.885 (m.60 3. 28.703.631.214. (119.95 7.957.a.617.206.447. 1H).2.982.226. 31.

8 2.4 Others 5.098 F 44. 72.473. 115.616 ∆ α 0.4237 log P F 44.378 (t)). 119. 78. -120.70 3.227. 1H).4. (115. 3.115. 4H).080.31 28. 2941.a. µ π* n.950.1962 f(kirkwoo d) 0.82 ε f(kirkwoo d) 0.1694 π* ε H-RMN 13 c) α 1.1 2. C-RMN 116.4069 n. 6H).7F CAS 1598-17-0 F F F OH F F O Structure F F O F F F F F 2.74 4.9 10.862.4-heptafluorobutoxy)-2-propanol 7F.146.405-3. 2.674.421 (s. 112.517 (sa.890(c)). 3480 FT-IR 456.5F CAS 935273-12-4 F OH F F F O F Structure O F F F 2.5 Polarizability 1.3978 0.a. π* ε H-RMN 13 C-RMN c) α 1 1.140 1. 3.3-bis(2.838 30.596 57.69 3. 59.941 204 1. Name Code 1. 114. 3.998 950.1 elemental analysis Experimental elemental analysis O F C H O F 35.92 0.434.52 Polarity n.719. 1142.903 206 1.a. π* 0. (118.1779 8.3522 f(dielectri c) H O 3.5 Polarity Vaporization Polarizability Hydrophobicity Others 0.174 (t) F-RMN 1220.01 f(kirkwoo d) Name Code CAS 1 H-RMN 13 C-RMN FT-IR m/z C 53.4178 c) 0. ε α n.741.9428 n.56 10. 3. 3. 3. 69.738.160. 43.1826 f(dielectri ∆ 6.a. 1457.04 f(kirkwoo d) 0.1 Structure O O 20637-49-4 3. µ b.a. p.0.1715 n.4032 b.4 0.416 (t)) 19 -127.50 Vaporization 197 b. 67.562.892. 2943.3354 2.671. 120. 3490 FT-IR 356. 1H).120. 3.438 n.a. 3.35 2. 3. 3. 3. 113. 1-iso-propoxy-2.329 (s.0.4504 51. (114.883 28. 4.417 (t)) 19 -123. 1250.723. log P f(dielectri ∆ 0.918.3837 0.3901 12.026 (t.00 C 32.747. 2899. 116. 116.21 10.248. 69.2.3-bis(2.a.629 19. 68.8 Hydrophobicity 1.3. 3.247.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 30.479 (c)).992. 2888.3.958.3-dimethoxypropane Structure O 14S . (119.48 53. 2987 134.a.3. 0.3-pentafluoropropoxy)-2-propanol 5F. 1.224 (t)). p.55 8.757.2.460 (m.219 150 n. 119. 113.740 (m). 1440.77 0.983 (t.909 (m).039 (t)).5609 1.96 2.400 Name Code 1.1.24 n.3. -83. -81.483 (d.71 Theoretical H 10.94 Polarity 0. 3.a. Name n. 4H).3-trimethoxypropane O 1. 3.7 53.370.70 µ O 18.3 58.C 32. log P f(dielectri ∆ 0.a. 1H).687. 68. 68.4314 1.981.289.4.4 Vaporization Polarizability Hydrophobicity Others 2.111.57 n. 1. 3. n.804 (m) F-RMN 1160.a. (112.52 58.a. 73.3298 3.1 Polarity Vaporization Polarizability Hydrophobicity Others 0. 5H) 57. p.34 30. 0.83 13. 120.878 (m).2.84 1 H 3. 73. 1H).681 (t. log P 0.00 53. 4H) (67.970 (m. 2890.070. p.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 28.554 µ b.a. 3H).969 (m.698 (t.3354 n. 4H) (67.38 14.657.

3.892. 50. 1. 1.953.353 C-RMN 923. 72.952. 3.397 (m. 1. 1.851. 2H). 1.49 0.189. 2966 FT-IR 204.341.00 65.932. 2929. 2872.533 (m.3 Polarity Vaporization Polarizability Hydrophobicity Others n.448-3.349 (s. 1. 1.a.a. 1.730 µ b.811. 3.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64.02 ε f(kirkwoo d) Structure O O n. 3.344 (s.182. 72. 1H) 13 21.a.122.1. 1.028.a. 6H). 77. 45.371.499.a. 2904. 2H) 13.516.540. 3. 2H). 70.304.086. 1.417 (s.23 0.0 11.877.3-dimethoxypropane 4t. 1. 2974 176.a.2 Theoretical elemental analysis Experimental elemental analysis H O F C H O F 12. 1.831. p. 3H). 72.333.357 (s. 2929.867.505.a.544.416 (sa.179. 3. µ b.1 Name Code O Structure O O n. 1.63 21. 1. n.301. 1. 0. log P f(dielectri ∆ -0. 57. 3. 9H).01 O c) 2-n-butoxy-1-tert-butoxy-3-methoxypropane 4t.536. 3. 67.114. 3.515.44 Polarity 0.a.00 59. n.104.06 n.362. 72.163 (s.957. 2H). 1.114. 3H). 2893. 0.a.395-3. O Structure O O 0. 27. 6H).1.1 C-RMN FT-IR m/z n. 3H).586 (m.553.241. 1.327 (s. C 66. 1.4044 2-n-butoxy-3-methoxy-1-iso-propoxypropane 3i. Name Code H-RMN 13 n.885.476 (m.873.15 n.414.570 (q.8724 n.1 elemental analysis Experimental elemental analysis O F C H O F 27.a. 1.a.a.188 1106. 180 b. 3.204.1966 π* ε Code CAS c) α n. 21.390-3.a. 61. 70.4044 0. p.108.559.98 0. 1. 2H).518 (m.910 (t.a. 79.918 1.a. 1. 180 n.393. 78. 32. 3.a. 0.1 CAS 172888-77-6 H-RMN C-RMN FT-IR m/z 13 C 61. f(kirkwoo d) n. 1.9 Polarity Vaporization Polarizability Hydrophobicity Others 15S .934 C-RMN 1126.865. 2972 FT-IR 162. 3. 3H). 57.578 (t. 1.3616 1. 19.136 (dd.a.a. 67. 1. 3H). 2970 218. 1. 3. 59. 3.0 11.297. 961. 22.00 21. 34.a.88 n.450 (s.546. 1 H-RMN 3. 1.728 1098 2877. 3.59 0.390 (m. 0.531.21 µ 0. CAS n. 59. 72.33 π* α 1 Theoretical H 11. 4.032 f(kirkwoo d) Name Code 1-tert-butoxy-2.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 59.352.67 11. 3H). 0.119 (dd. 8H) 13 13.5437 0.00 61. 9H). 215 n.1 n.798.3i. 1.360. 1H) 27. n. 2929.84 23.a. 21.993 170 1. 2871.576 (q. 5H).386-3. 72.322.521.18 29.904 (t.a.751 n. 3. log P f(dielectri ∆ n.315.500.8 11. 1.2 n. 1. 0. 32. CAS 0. 1. 3. n.1 Vaporization Polarizability Hydrophobicity Others n. 0.1 11.a.4.025 39.195.53 0.a.4.120.541.a. 1. 59. 3H). 1.929.6 Polarity Vaporization Polarizability Hydrophobicity Others 0. p.012.561 (m.893.190.054.099. 1. 1128.a.378.129. 79. 3H). 3.487-3. 72. log P f(dielectri ∆ n. π* ε 1 H-RMN c) α 1 0.23 11.a. 19. 60.171 (s.89 n. 3H).417.561. 4H).419 (m. 1. 3.00 64. 2H). n.

08 n.221. 5H) 19.00 65. 2H).205.a.18 n.932. 1.222. 1.a.08 n.491. 3. 1. 57. 1.1 11.1 CAS n. 71. 3. 1.203 (dd.a.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 66.180. n.290.a. H-RMN 3. 234 n. f(dielectri ∆ n.242. n.869.511. 1. n.548. 28.421.84. 3H).530. 3.584 (q.a.a. 2868.a. 70. n. 1.308. 3.a.871.917.519.410-3.568.344. 0. 3H).01 12. 4H). f(dielectri c) log P n.a.a. 193 µ b. 1. 1.797.524 (m.402 (m.327. 1. 32.358 (s. 1.4. 1.a.582 (m. 0. 72. 31. 1.886. 1H). µ ε f(kirkwoo d) n. p.a. Name Code 2-n-butoxy-1-iso-butoxy-3-methoxypropane 4i. 1.187. 1.405-3. 1.364. 1.a.n. 2H).365.117. n. p. 3H) 16S . 1.a. 19.0092 n. 2932.887.a.327. n. 2.556. 1. 4H). 1. 59. n. 79. 3.566 (q. 2872. 3H). 1H). 2871. p. 6H). 3. 3. 3. 1.a.718 C-RMN 1115. π* ε Name Code CAS c) α n.23 0.a. α n. f(kirkwoo d) n. 2955 FT-IR 218.a. 3. ε f(kirkwoo d) n.a.432 (t. p.562. b.442. 0.503.a. 70. 2H). 1. 2930. 0.0774 n.248.346.184.914 (m.439 (s. n.830.383 (m. 1.186.879.a. 3H). H-RMN c) n. 1-iso-butoxy-2. 1. n. 1. 1 H-RMN 2H).a.a.a. 0. n.a. 1. 2956 FT-IR 176. 31.326. 1-n-butoxy-2.260. 0.1 Structure O O n.579 (t.2 n. ∆ 51. 2H) 13 13.a.1. 0. 1. 1.567. 2926.835.359 (s. 3. 1. 3.532. 2894.a. 0. 1. 1.78. 1H).857.819.5 Polarizability Hydrophobicity Others n. 199 log P µ b. 1. 1. 3.20 Experimental elemental analysis C H O F 61.219. 6H).460-3.852.a.489 (m.531-3.505 (m. 1. 1. 1. 1.4748 f(dielectri ∆ n. 77.a.530.407. π* ε Name Code CAS c) α n. 1.306. 0. 1. 1. 3.a. µ b. 59.a.44 27. 19.a. Structure O O O 0.889 (d. π* n.a.00 Polarity Vaporization n.454 (s. 6H).514 (m. 59.332.a. 71.886.a.550.269. 1.830.382.922 (dt. 1.383.3-dimetoxypropane O 4. 1.394. 59.309. 3H).77 n. 3. n. n.a. n. n.864.899.4. 2H).880. 79.a.9 11. H-RMN 13 C-RMN FT-IR m/z C 61.3-dimethoxypropane O 4i.847.a. 3.388 (m.904. log P 2.a.813.1 Structure O O n.401 (m. 1. 1. 1.197 1112. 70.00 60.a. 19.8 12. 0.905 (t. 2H). 3.345. 3H).33 π* α 1 d) n. 72.08 0.869.254.513.881.438-3.351. log P f(dielectri n.a. 1H). 1. 1. 1. n. 3. ∆ 219 46.2-di-n-butoxy-3-methoxypropane O 4.1 Structure O O n.a.a.888 (dd.1. 1. 70. 0898. n.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 61.916 (t. n.872.308.346 (s.612.363. 0.23 0.a. 1. 0. 3H).546. 3. 4H).357 (s. 1. 12.869.a.a.197. n. 1. n.a.289.00 21. 1 1.902 (m.304 (d. 0.a. 0.a. n. 3.586 (q.a. 1.a. 59.072. 2953 Name Code CAS 1 f(kirkwoo Theoretical elemental analysis H O F 11. 3.2 Polarity Vaporization Polarizability Hydrophobicity Others n.a. n.44 27.802. n.897. 3. 0.a.885. 3. 72. 2900.704.551.174 C-RMN 1194. 57. 0.780.a. n. n.6 Polarity Vaporization Polarizability Hydrophobicity Others n. 7H).369. 1.a.33 11. 3H) 13 13. 0.397. n. 5H).887.

33 c) f(kirkwoo d) n. 3.2 CAS n.1 CAS n.a. 3H). p. O Structure O O 1. n.134 (dd. 59. 17S .a. 9H).130.605. n. 3H).a.a.a. 190 n.a. 1. 3.858. n.671 (dc. 3.01 π* α 13.170.a. Name Code 3-ethoxy-2-methoxy-1-iso-propoxypropane 3i.636. 78.188 (t.400-3.098. n. 1. 27. 1.a.23 0.098.611. 70. 3. µ b. 3.a.981 C-RMN 1114.886.460-3.a. 3H).2 Polarity Vaporization Polarizability Hydrophobicity Others n.646.280.648. 1.98 0. 48.185. 72.a.440 (m. 1.136.152. 32.653. 183 n.72 n.659. 66. 3.a.00 61. 21.2 Theoretical elemental analysis Experimental elemental analysis H O F C H O F 12. n.a.a.259. 3. 72.00 65.2. 3H). 19.219. 65.a. 67. n. n. 2867. 50.35 f(kirkwoo d) n. 65. 59.919. 227 n.13 C-RMN FT-IR m/z C 66.646.2.535 (m. n.65 25.a.733. 1. 3.a.a. 72. 3.a. 72.a.a.1. 26. 1.99 n.a.a. 161 n. p.392. 61.1 Theoretical elemental analysis Experimental elemental analysis H O F C H O F 11.a.721. µ b. n. 2H). 3.5 Polarity Vaporization Polarizability Hydrophobicity Others 0.120.33 11. log P 0. n.a.02 n.a. f(kirkwoo d) n. 72. 59. 1.579 (m.44 27. 70. 2925.654 (dd.a. 3.23 0.a. 43. 70. f(kirkwoo n.a. 2900.a.a. n. n. 67. n. 3.158 (dd.00 62. 77.629. 2901.00 61. O Structure O O 1.434 (s.17 n.17 n. ε α 0. µ b. n. n. 2H) 13 15.1 CAS n. 3.a. log P f(dielectri ∆ n. Name Code 2-ethoxy-3-methoxy-1-iso-propoxypropane 3i.a.a.637.533 1127.215 (t.63 n.930. 72. 2870. 2956 218.181-3.23 0. n. 1. 79.115.3379 f(dielectri ∆ n.618. 19. 3H). n. n.02 n.095.12 11.320.481. 1. 1.238.363 (s. 3.174 (s.368 (s. n. n.1 Polarity Vaporization Polarizability Hydrophobicity Others 0.234. 2H) 13 15.a.202.870.8925 f(dielectri ∆ 0. 1.a. log P 2.666. 28.197.631.a. 1.401 1114.966.142.613.988.435. 3.051. ε c) n.850.9 Polarity Vaporization Polarizability Hydrophobicity Others n.922. 3.a.153. 6H). 1.00 21. p.a.0975 n.5 11.697.a. p.44 27. 2971 FT-IR 176. 2973 FT-IR 190. 3.179. 3.a.a.220 (t. π* ε 1 H-RMN c) α 1 0.a.1 11. 2873.a.592 (m.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63.15 n.8925 f(dielectri ∆ -0. 2929. 2931.a.a. 2873.759 C-RMN 1111. 6H). 77. π* ε 1 H-RMN c) α n. log P 0. 3H). 2973 176.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 61.224. 3. 8H) 15. 57. 1. 22. O Structure O O π* 1. 21.119.978.a. n. 3H). n.0 11. n. µ b.032.a.22 H-RMN C-RMN FT-IR m/z 13 C 61. 21.415-3. 1. 6H). 77.9 12.a. Name Code 1-tert-butoxy-2-ethoxy-3-methoxypropane 4t.

0 11. n. p.23 α f(kirkwoo d) n. 1.a.550 (m.652 (dd. 1.16 n.a. 72.23 0.659. 2970.617. 1. H-RMN C-RMN FT-IR m/z 13 C 63.a. 3. 3.877.097. 2929. 70.a.795.a. 1.910. 2959 FT-IR 190. 3.819.163. 71.12 11. 59.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63. 57.560 (m. 1.873. 3. 71.601.1 Structure O O n. 1. 3H). 27.551. 3H).415-3. 3.4949 µ b.596.280. n.a.a. 3. 70. 79.78 n.18 n.165 (s. 1. 3. 2811. 2973 190.841.886 (m. n.1. 1. 3H).2 elemental analysis Experimental elemental analysis O F C H O F 25.571.528.360.a. µ b.a.170. 28.595 (c.60 n. 3.496.391 (m. Name Code 1-n-butoxy-3-ethoxy-2-methoxypropane 4.877. 2929. 1-iso-butoxy-2-ethoxy-3-methoxypropane O 4i.630. 2900. 66. 6H).1 Structure O O n. 1.23 0.836.627.1.575 (c.298.350 (s.2 CAS n.285. n. 19.563. 60. 4H). 1.a.8 11. 0. 31.0975 b.552.648.894 (d.652 (dc. f(kirkwoo d) c) n.317.21 α Name Code CAS 1 H-RMN 13 C-RMN FT-IR m/z C f(kirkwoo d) n.235.892.209.784 1117.725. 3H). 3. 65.472 C-RMN 1121. 3. 77.209 (d.363 (s. 3. 0. 1. 0. 2H). 31. 0.65 Polarity 0. log P f(dielectri ∆ n. 1. 3H).328. 70. 0.443 (s.188. 1.341.379.205 (t. 3H) 13 13. 1. 1.596. 9H).420-3.095. 2H). 3.a. 1. 0.a. n.7 Polarity Vaporization Polarizability Hydrophobicity Others n. 6H). 1H). 3.584.a.180.403-3. 72. 3. n.248. 3. 2869.354 C-RMN 1117.a.a. 79. 3.2 CAS 346705-85-9 O Structure O O 0.305. n.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63. 2H).172.941.10 n.354.895.12 11.a. 78.a.373. 1.557.2 Polarity Vaporization Polarizability Hydrophobicity Others 0.15 µ π* -0.914 (t.2. 15. 2893.12 Theoretical H 11. 193 n. 1. 1.189. π* ε Name Code CAS c) 0. 3. 2932.246. 59.8 11.47 ε O Structure O O 1. 1. 2958 FT-IR 190. 1. 3.564.513. n.00 63. 1.654.378.2.44 1115.23 0.a. 2H). 3.65 25.925. 1. 3.919 (t.23 α 0.a. 3.197 (t.635. n.a.645. π* ε 1 H-RMN c) 0. 1-n-butoxy-2-ethoxy-3-methoxypropane O 4.927.9 Vaporization Polarizability Hydrophobicity Others n.335.16 n.207 (t.00 62. 3H).a. 57.526. 43.a.470.581 (q.510. 3.853.564. 3. 9H).882. 1. 2970 190. H-RMN 3. n.668. 1. 3.a.65 25.901. 2H) 15.538. 19.a.a. 1. 1.217 (t. 65.d) 1 Name Code 1-tert-butoxy-3-ethoxy-2-methoxypropane 4t.613. 72. 2928. 77. 1. 3H).a.502 (m.533.a. 1. 1H). 0. 1. n. 2H).199. 3.421-3.510 (m. n.567 (q.869. 3H). 15. 1. 1. 1.0975 n. 2957. log P f(dielectri ∆ 0. 51. 1. 70.635. 52. 66. n. 1. 1 1.a. 7H) 15.182.16 n. 1. 209 n. 1.547.a.599. 2868. 209 n. 0.a. 1. 3H). 3.858.278. 2H) 13 13. 3. 70.323. p.398 (m.2 Theoretical elemental analysis Experimental elemental analysis H O F C H O F 18S .a. 1.a.455 (s.705.192. 1H). 3. 19.142. 1.160.00 62. 3.311. 1. log P f(dielectri ∆ 0. p. 2905.a.

169. 7H) 13 15.65 25.00 Vaporization 198 b.a.00 62. 1.a.65 25.643. 1. 3. 66. 70. ∆ α n. 2929. 65.0 Polarity Vaporization Polarizability Hydrophobicity Others n. n.428-3. n. 22.a.158.39 n. O Structure O O 1.44 f(kirkwoo d) n.a. log P f(dielectri ∆ n. 1.a.022.32 n. n.23 n.2. 27.3-diethoxypropane 4. 3.90 n.a.a. 2929. 3. 1. 19.174 (t. 1. 3. CAS 1. 78. 1.609.0 Polarity Vaporization Polarizability Hydrophobicity Others 0.a.644.84 23. π* ε 1 H-RMN c) α Name Code 0.158.867.2413 n.641.361.824. 2H). 1.a. 3. 3. 2869. 67. ε f(kirkwoo d) 45. 3. π* ε 1 H-RMN c) α 0. 70.a.550.2 Structure O 19S . 57.128.355.16 n. 37. n. 3.a. log P f(dielectri ∆ -0. 1.180. 72.12 11. 2H) 13 15.608. 2H).866.186. 15. 1. 15.a. 3.a.160.589.198 (dt. n.857.17 n.a. 2900.07 f(kirkwoo d) n. n.a. 61.12 11.967.2.a. 77. n. 70.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63. n.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64. n. 6H). 21.a. 201 n.660 (c.525 (m.a.625.a.a.661 (c.a. 1-tert-butoxy-2.3580 µ b.684.277 C-RMN 1117.a. 2867.569. n.a. Name Code 2. n. 9H). 3H). 1.a. 1.193.626. 3.874 (m.729. 2H) 13 15. f(kirkwoo d) n.068. 2869. 65. 79.438-3.392-3.202 (dt.559 (m. 78.580. 1.a.139.a. 3.123. n.207. 1.1.a. 1. p.2 Name Code O Structure O O n. 1.a. 3H).2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 63. 0.129.790.a.152. n.987.854 C-RMN 1120. n.a. 43.12 11.077 C-RMN 1114. 3.535.422. 1.1 11.2 CAS n. n. 1. p.a. 1H).a.23 0.67 11. 1.702. f(dielectri c) 11. 3.623. 3. n. n.184.533 (m. p. 6H).a. p.840. 3.a.4463 µ b. 2973 FT-IR 204. 1. 1. 1.138. 1.3580 log P n. 3.a. 1.162 (s.a.520.0 Hydrophobicity 1.581.144 (dd.a. 1.a. 6H).596 (m.a. 3.157.00 63.0 11.00 64.167. O Structure O O 0.176.0 Polarity Vaporization Polarizability Hydrophobicity Others 0. 2973 FT-IR 190.a. µ b. n.195.a.807. n. 3. 1-n-butoxy-2.774. n. 1.59 n.0 Polarizability n.115.a. 3. Others n. n. 66.175 (dd. n. µ 25.566.49 0.16 n.a.163. 2955 FT-IR 190. 28.841. π* n.a.424 (s. 70. 1.23 0.506. 1. 3. 0. log P f(dielectri ∆ 0.a.a. π* ε 1 H-RMN c) α n. 6H). 51. 2895.a.178.63.a. 72. 3.011. 6H).1 12.3-diethoxy-1-iso-propoxypropane 3i.629.2 CAS n.2.65 Polarity n. 1192 n.3-diethoxypropane 4t.857 (d. 7H). 1. 3. Name Code 1-iso-butoxy-3-ethoxy-2-methoxypropane 4i. 199 n.99 63.a.154. 66.

1.16 n.4135 1. 19.676 (c. 54.095. n. 2H).a.a.574 (c.599 (c.293.874. n. 2H).862. 3.a. 0.890.546.67 11.3-diethoxypropane O 4i. 6H).215 (dd.181. 2H) 13 13. 1H).511.175 218 1. 1.308. 3.577. 15. 15.098.326.612.093. 31. 1.602.140. 1. 1-n-butoxy-2-methoxy-3-iso-propoxypropane 3i. 3.a.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64.31 4. 3.a.778.987.674.314.a.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64. 1. 1. 2931. 77. 8H).181. 3H). p. 31. 1. 1.536. 65. 210 n.a.619.564 (q. 1. 1. 1H). 1. 71.931. 2H) 13 15. H-RMN 3. 1 1. 1.8724 µ b.1998 π* ε 1 H-RMN c) α Name Code 0. 1.173. 2H). 8H). n. 65. µ b. 57. 2869.807. 3. 2973 FT-IR 204. 67.1.208. 3. 15. 70.0 11.472.861. µ b. 1.623.216 (dt.a.171. 2861.a.800 61. 1 1.4 O Structure CAS 1 H-RMN 13 C-RMN FT-IR m/z O O n.413-3.332. 1.382601-24-3 0.a.15 n. 1. 78. 3.a. 19.694.840.370.493. 1. 2927.07 f(kirkwoo d) 0.7068 n.910 (t.296. 0. n.00 64. 6H).252. n.2 Polarity Vaporization Polarizability Hydrophobicity Others 0. 3.544 (q. 2909.587. 1.250. 3.756.a.613. 1H).562. 1.618. 70. 71.410 (s.658.2.548.198.541 (q. 70.510.316. 1. 1. 1. 3. 66. log P f(dielectri ∆ 0.873.173. π* ε Name Code CAS c) α n.190.781.390-3.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 64. 1.a.1 1. 3H) 13 13. 1. 1. 3H).606 C-RMN 1114.637. 21. 1.169 (t.640. 1.3585 1-n-butoxy-2-ethoxy-3-iso-propoxypropane 3i. 1. 1.098.383-3.203. n.211 f(kirkwoo d) n.108. 1. 2H). 0.93 n. 21.362 (m. 31.831.907 (m. 1.490 C-RMN 1122.641.488.16 2.49 0.472. 2H).49 0.669 0. 2H). p. 1.8437 n.49 0.164. 3.933.522 (m. 1.67 11. 21. 1.4 Name Code O Structure O O n.113 (d. 3. 70. 6H).595.155.516.877.170. 6H). 1.a.a.a. 19. H-RMN 3. 3. log P f(dielectri ∆ 0. n.274.a.892.194. 2959 FT-IR 204. 1.a.799.a. 1.311.886 (t.970. 1. 49. 1.198.235.84 23.510. 65. 3H). 1.849.547 (m.00 65.a.a. 2931. 8H). 2H) 13. 1. 1. 3. 1.344.598.857. 2897. 28. 0. 71.868.5 11.a. 1.734. 1-iso-butoxy-2. 1.67 11.531. 2H). 3H). 77. 1. 1. 21. n. 3.549. 3.574. 70.844.574. 1. 71.211. 1. 1.134.190. 3.796 1122.891. 2905. 1.406 C-RMN 1114. 1.630 (c.304. 2867. CAS 0. 1.a. 19. 1. 3.716.151. 3. 1. 1.349. 77. 0.8952 n.00 Polarity Vaporization Polarizability Hydrophobicity Others 0.a. 1. 1.543 (m. 217 n.494.113 (dd.288.389 (m. 0. 67. log P f(dielectri ∆ 0. π* ε CAS c) α 0. 71.199 (dt. 3.623.190.269. 3.351. 0. 2958. 3. 1. 66.a.561. 3. 0.527. 2968 FT-IR 204. 3. p.507. 0.644. 1.2.84 23.330.41 n.a.865 1. 6H). 0. n. 6H).2 Theoretical elemental analysis Experimental elemental analysis 20S .525. 3.823.367 (m.894 (d.880 (t.9 Polarity Vaporization Polarizability Hydrophobicity Others n.654 (c.570. 3. 15.440-3.84 23.548 (m. f(kirkwoo d) n.931. 1.2 Structure O O n. 70.18 n. 2969 218. 79.996. 3.87 8.877.

2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 66. n. 1. CAS 0. 70.295. n. 2H). ε f(kirkwoo d) 51. n. 1.783 48.06 5. 9H).4 Name Code O Structure O O n.539. 3. 3. n. π* ε 1 H-RMN c) α -0.045 C-RMN 1119.553 (q. 79.15 20. 0.a.564 (q. 1.a.01 12.a. 1H) 13 13. 63.893.a.a. 1. 1. 9H) 13 13.607. n. π* ε 1 H-RMN c) α n.903 (t.375 (m.327. 2866.00 Vaporization 222 b. 1.522 (m.613. 6H).0 12.375-3.a.497. 70. log P f(dielectri ∆ n.184 244 1.4748 µ b. 1.435 (s. 2869.402-3.a. 1.00 21.a.353.314. 2972 FT-IR 232.139. 2956 FT-IR 218. 7H).149 (s. 0. 61.a.a.00 67.844.a. 1.1. 1.140 (s. n.589. 31.3 n. 72.302. n. 2H) 13 13. 1.157. 27.338.2017 π* ε 1 H-RMN c) α 0.3-di-n-butoxy-2-methoxypropane 4.624. 1. F 0. 3H). log P f(dielectri ∆ 0.a.00 65.3552 0. 2869.4 Name Code O Structure O O n.a.8 12. n.536.857. n.3 12. 1. µ O 21. n. 3.a. 1. 1. 2931.511. 1. 6H). n. 3H).a.a.57 C 66. 3. p. 2931. 3. ∆ α n. 2H). 70. 0. 1.198. n.2 Hydrophobicity 2.006.563.a. 0. 3-n-butoxy-1-tert-butoxy-2-methoxypropane 4t.a.357.20 12. 31. n. 4H).316 0. 19.00 21. 1.24 4. 1.a.a.4262 µ b.810.645.519. 27. 2. 1. p. 2957 FT-IR 218. p.66 0.a.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 67. 1.907.529.a. log P f(dielectri ∆ 0.383 (m.498.276.632.a.a.0 Polarity Vaporization Polarizability Hydrophobicity Others 4.a.98 0.277.42 n.333.1.01 12. 19.00 65. 61. 57. 0.282.a.369 (m. CAS 0. 3.214.179.868. π* n. 3H).519. 9H).98 0.494. 211 n.553 (q.a. 1. 31.175 (t.a.490-3.a.98 n.481.04 f(kirkwoo d) n. 57.692.2.a. 1. 2903.775. 1. 60.0 Polarity Vaporization Polarizability Hydrophobicity Others n. C-RMN 1118.300.a. 1.894 (t.331.15 2. 15.a.0774 µ b.8765 21S .525 (m. 1. 3H). 1. 1.547.221. n.4 Polarity Vaporization Polarizability Hydrophobicity Others 0. 1.6 Polarizability n.875. 1.4 3. 3.2212 log P n. 1. 71. 3-n-butoxy-1-tert-butoxy-2-ethoxypropane 4t. CAS 0.345. 1. 1. 3. n. n.521 (m.878.767 C-RMN 1118. 72.a.828. 71. p. 2. 3H).01 H 12.314.850.642 (c. 1. 2931. 78.437 (m.536.04 n. 3.887 (t.194.885.364. f(dielectri c) H O 12.367-3.308.a.417 (s.290.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 66. 0.a.866. 1. 65.4191 2. f(kirkwoo d) n. 2H).14 n. 19. 4H). 71.319. Others n.482. 234 n.377.78 0.4 Name Code F O Structure O O n.a. 1. 1.C 66.351. 1. 79. 2H).a.00 Polarity n.680 4.780.10 f(kirkwoo d) 0. 1. 3.

319.721 0. 3H). 2930.326. 1. 125.449.4 CAS n. 3. 2H).395-3. 2867. 32. 3. 1.237. 70.288. 1. 2.344.a.448 (sa.251.544. 57. 3. 1. 1. 1.844.32 n.540. 1. π* ε 1 H-RMN c) α 0. 2925. 3.a. 6H). 6H). 3.623. 3. 3.12 4.808. 19. 1116. (119. 71. n.540. µ b. 122.2. log P f(dielectri ∆ 0. 1H).5 Polarity Vaporization Polarizability Hydrophobicity Others 0.a. 1. 1.528. 1H). 2H). 2931. 3.895.655 (dd.4 CAS n.591. 77.a. 1. 2867.a.4.a.357. 71.231.a.273.585 (m. 1. log P f(dielectri ∆ 1.123. 28.739.a.855.128. 2890. 3H). 1. 1.a. 1. C-RMN 19 d) n. 0. 1. n.776. 3. Name Code 1.852.882 (m. 3. (68. 0. 1.558. 1.816.a.728. 2869.a.816. 0.826. 1.139.862 (t.832. log P f(dielectri ∆ n.464. 0.743.334 (m) 1120. 2957 FT-IR 232.915.39 n.a.110 (d.a.467 (m.273.812.903. 0. O Structure O O 0. 3.2. 1.a.501. p. 2H) 13 13. 2973 22S .00 21. 19. O Structure O O 0. 2971 FT-IR 218. 1H).8035 3. 3.095.146 (t.15 n. 1. 7H).250.380.517 (q. 2H). 1.310.00 67. 3.590. 69. 3. 3. 3H). 1. 1. n.518.496.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 67. 1. 2H).6867 n.792.a.089 (c)) -74. 3. 1. 72.799. 226 n. 68. 3H). 3. 3.06 2. 1. 63.3-tri-n-butoxypropane 4. 1. 1. 3. 3H) 13 13. 1.858.447.899.557 (q. 2901.574 (q. 0. 2.866. p.2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 69. 1. 19. 1H). 31.556. 2H) 21.782.503.a.a.842 (m.486. 68. 77. 72. 57. 3.1.833 (d. 3.a. 6H).2 Polarity Vaporization Polarizability Hydrophobicity Others n. 31.921 (t.a.510.520.880. 1. 3H).531.430 (s.867 (d. 1.8636 O F F Structure O O F 1.4 CAS 131570-29-1 O Structure O O 0.2.844. 70.3558 Code H-RMN 13 f(kirkwoo 3-iso-propoxy-2-methoxy-1-(2. 241 n. 2H).370.2032 π* ε 1 H-RMN c) α CAS n. 70. 3H).244.727. 1H).962.837. n.151 µ b.877. 65.4237 3.618.0 12.a.39 18.146 (d. 3. 3.540. 3. 11H) 13 13. F-RMN FT-IR 0. 3.a. C-RMN 1122.363-3. 78.494. 6H).3F Name 1 n.505. 1. 21. 0. 1.800.299 (c)).98 0.39 270 1.164.339. 70. 79.287. 3.5 Polarity Vaporization Polarizability Hydrophobicity Others n.a. 71.822.483. p. 0. 128. 1.531 (c. 1.1. 3. 0. 3. 15. Name Code 3-n-butoxy-1-iso-butoxy-2-ethoxypropane 4i.a.Name Code 3-n-butoxy-1-iso-butoxy-2-methoxypropane 4i. 6H).700 77. 0.3 2.866 (c.a. 0. 78.a.325.759.895 (t. 0.3 11.142.15 20. 0. 1. 6H).a.344 (m. 2957 FT-IR 260.766.644. 19.506 (m.158. 1281.00 69. 3.209. 1H).624. n.525.226.420-3.3379 µ b. 2932. 28.609 (c. 1. 1. n.2-trifluoroethoxy)propane 3i.749 (d. n.826. 1. 2H).752. C-RMN 1116.307. 6H).2 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 66.43 0. 0. 66.493.129.809.376 (m. n.269. π* ε 1 H-RMN c) α n.400 (m.305 C-RMN 1098. n.723.574.01 12. 1. 3. 1. 3. 1. 70.503.181 (dd. 1.522. 1.66 0. n. 1.363.445.a.86 n.555 (q. 3. 3. 1. f(kirkwoo d) n. 2. 1.858.849.408 (sa.00 f(kirkwoo d) n.0 12. 31.257.18 12.628.307.175.00 66.a.283.382. 1. 1. 1. n. 70. 79.301. 3.20 12.458.917 (t.195. 3.850.885.123.111. 51.a.

905 (dd. -74.643.2. 1.2-trifluoroethoxy)propane 3F.574.2-trifluoroethoxy)propane 4. 2H). 0.668 (dd.763.1862 O F F Structure O O F 1.128. p. 69.84 19. log P 1 H-RMN 23S .734. 69.95 Theoretical elemental analysis H O F 7. 1H).2. -74.5 7. 1277.a. 1.756. 125.359 (c)).662.779. 70.353.335-3.278. 42.3816 1. 2.17 7.1 n. 1298. (119. 2950 FT-IR 244.0672 Code 3-tert-butoxy-2-methoxy-1-(2. 57. 3.867. 3H).455 (3H).729.834. 3. 0.8322 µ b. 79.518. 3.77 42. 9H).2 Polarity Vaporization Polarizability Hydrophobicity Others n. 1H). 1. 68. 1. 2H).a.785 (dd. 3.a. 3. 3. 57.893 (c.8 23. 128. 9H). 19. 2H) 27.19 35.158 (s. 3. 2938 FT-IR 270.6 24.435 (s.544 (q. 3.878. 82.632.883.237 (s.55 4. -74.370 (m. 3.301. 3. 1H). 70.364 (c)). 3.a. 3. µ b.856. 2930. π* 0. O Structure O F O 0. 79.3F CAS n. log P f(dielectri ∆ n.480.4281 1. 2881. n. n.705. 13 C-RMN 122.a.337 F-RMN 1126. 128. 3. f(kirkwoo d) n. 69.690. 3.848. 3.7561 2.a. n. 69.5511 n.285.980. 13 C-RMN 125.44 20. (119.701. 3. 207 n.893. 3. (68.85 24. 1.749.063 (c)) C-RMN 19 -74.4 4.849.507. 1.2 42. 3.020. 3.122 (c)) 19 -74. 72. 3H).760.37 3.a.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 35. 68.3F CAS n.23 4.506. 3. F Structure O F F O O F 3.027.24 f(kirkwoo d) 1. 3.351 F-RMN 1120.217 (c)) 19 -74. 3.495 1.1 Polarity Vaporization Polarizability Hydrophobicity Others 1.730. 3.312.384.a. 122.350. (68. 3.361. 2H).1 Polarity Vaporization Polarizability Hydrophobicity Others 0.56 4.345. 2972 FT-IR 244. 71.886 (t. 3. 3.679. n.33 49. 31.849 (c)).4232 Name Code 3-n-butoxy-2-methoxy-1-(2. 1.550 (q.3-bis(2.495. 0.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 49. 2H).7 7.1 m/z C 46.1.415 (sa.938 ∆ 39.9 23. 3.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 49.772 (dd. 60. 1.900.537 (m.3F CAS n. -74.76 Polarity Vaporization n. 3.883.133. 3.a. 1.334. 122. ε f(kirkwoo d) 9. 3.33 49.827.a.65 23.346.385.235 178 1.23 Experimental elemental analysis C H O F 46. 2H) 13 58.a. (69.362. 2865.512.139 47.a.484 185 1. 0.285.810 0.1886 4.3476 1.210.4 π* ε 1 H-RMN c) α 0. 71.1535 n.059.69 9.48 17.4 Polarizability Hydrophobicity Others 1.a.692.682.353.1. 3. n. 3. 125. 1279. Name Code 2-methoxy-1.a.506 180 µ b.532.2-trifluoroethoxy)propane 4t.534.849.052.a. 3H).755. 3. Name 4.046 µ b. p.175. log P f(dielectri ∆ 0. 3H) 13.746. 3.a.838. 3.0456 n.262.3748 1. p. n.230. log P f(dielectri c) n.042.861 (dd.2. π* ε 1 H-RMN c) α n. 3.84 19.266 2.871.65 23. 2H).a.1. 70.020.5 0.19 0.a. 73.298.a.718 (dd. 3.269. (119. p. 128.17 7. 72.3 7. 2922. 1.520.88 α n.482.a.a. 3.339 F-RMN 1162.

147.36 f(kirkwoo d) n. n.901.268 171 1.873.678.2 4.2871 F Structure n.77 n. 3.692. 3.592. (68. 3. 3. 3.325.653.554. 65.a.3516 2.a. 2H).1777 π* ε 1 H-RMN c) α 0. µ b.502. 1.320. 3.662.813.a.4.534. 3.3F Name Code Structure n. 50. 2H). 73. 3. 3. 125.550. 122. log P f(dielectri ∆ 0. 69.a. 3. 1. 77.835 (dd.883. 3. n. 3. n.830. 3.3-bis(2.11 38.7 5.822.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 38.a.666.08 n.2. 77.377. 1H). 69.0 Polarity Vaporization Polarizability Hydrophobicity Others 0. 128.a.850.57 n.703.608 (d.518.688.81 15.a. 3.715. 3.857.714. n. (dd. 24S . 3.806.09 n. 13 C-RMN 122. 3.770.567 (t.382. CAS 2. 3. 2H).590. 3. 2936.895 (dd.305.31 5. 3H).538.2-trifluoroethoxy)propane 3F.701. 1.7 36. 1. n. 3. 3. 3. µ b. 71.330 0. 3.691.101 (c)) C-RMN 19 -74.2.a. 68. 2H).153.23 f(dielectri c) 1.a. 32.579. 2935.309.363.555. 2960 FT-IR 312.674 (dd.91 12. 1.866. 2H).4 Polarity Vaporization Polarizability Hydrophobicity Others 0.3F Name Code 3. 1. 3. 1.51 42.307.401 F-RMN 1166.573 (m. 3.2-trifluoroethoxy)propane 3F. 68.7 39.3-bis(2. 70. 2H) 13.658.a.188 (t.60 4. 2H).844.888.531.604 (q.044. 52. 3. 1H).547.1609 f(dielectri ∆ 1. (119.678. 3.744 ∆ 45.423 F-RMN 1162. 68. 3. 3. 3.712.386.625. 2H).039.a.1 m/z Theoretical elemental analysis Experimental elemental analysis C H O F C H O F 42.36 ε f(kirkwoo d) 13.729.37 36.π* 1. 0.97 16.828. 3. (68. 3. 2H). 3.872. 3.81 n. 0. 2978 FT-IR 284.400 (m. 3.a.726 (dd.475 (c)). 1. 2882. 2H). 3. 3.920 (t. 0.324.741 (dd. 2H) 13 15.429 0.2.363. 3.000.170. CAS F O F F O O F 0. p. 1.4473 2-ethoxy-1.343. 1. 1280. (119.958. 125.087 (c)) 19 -74. 1. 1.566. 3.852 (dd. 3.89 40.2 0. 3.33 (c)) 71. 208 n.a. 3H). 0.996.636. 3. 1.04 4.752.4437 1. 2H).1810 n. 1279.04 α 0.2266 2-n-butoxy-1. 128. 3. 69. 19. log P 3.a.55 f(kirkwoo d) n.1762 O F F O O F 1.700. p.879 8dd.648. 2876. π* ε 1 H-RMN c) α 0.a.572 (q.a.

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