Using Two Group-Contribution Methods to Calculate Properties of Liquid Compounds Involved in the Cyclohexanone Production Operations
Abstract
:1. Introduction
2. Two Group-Contribution Methods for Estimating Properties of Pure Substances
2.1. The Joback Method
2.2. Marrero–Gani Method
3. Evaluation of Estimates for the Selected Substances
3.1. Evaluation of Temperatures and Enthalpies of Phase Transition
3.2. Critical Properties
3.3. Estimation of Enthalpies of Formation and Thermal Capacities
4. Conclusions
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
Appendix A. Compounds Present in the Streams of the Cyclohexanone Production Process
- Cyclohexane feeding; cyclohexane, hydrocarbons.
- Oxidant supply; air.
- Entrance to oxidation; cyclohexane, hydrocarbons, cyclohexanone, cyclohexanol, light oxides.
- Nitrogen.
- Oxidation effluent; cyclohexane, cyclohexanone, cyclohexanol, light and heavy oxidized, peroxides, formic acid, acetic acid, other monocarboxylic acids, dicarboxylic acids, esters, butanol, pentanol, cyclopentanone, cyclopentanol, 2-pentanone, 2-cyclo-hexen-1-one, cyclohexene, 2-methylcyclopentanone, methylcyclopentanol, heptanones, 2-methyl-3-heptanone, 1,3-cyclohexanedione, 1,2-cyclohexanediol, methylcyclohexanols, ethers.
- Washing water; water.
- Washing emulsion; water, cyclohexane, cyclohexanone, cyclohexanol, light and heavy oxidized, peroxides, formic acid, acetic acid, other monocarboxylic acids, dicarboxylic acids, esters, butanol, pentanol, cyclopentanone, cyclopentanol, 2-pentanone, 2-cyclo hexen-1-one, cyclohexene, 2-methylcyclopentanone, 1-methylcyclopentanol, heptanones, 2-methyl-3-heptanone, 1,3-cyclohexanedione, 1,2-cyclohexanediol, methylcyclohexanols, ethers.
- Acid water; water, formic acid, acetic acid, other monocarboxylic acids.
- Oxidized product; cyclohexane, cyclohexanone, cyclohexanol, light and heavy oxidized, peroxides, monocarboxylic acids, dicarboxylic acids, esters, butanol, pentanol, cyclopentanone, cyclopentanol, 2-pentanone, 2-cyclohexen-1-one, cyclohexene, 2-methyl cyclopentanone, 1-methylcyclopentanol, heptanones, 2-methyl-3-heptanone, 1,3-cyclo hexanedione, 1,2-cyclohexanediol, methylcyclohexanols, ethers.
- Alkali; water, sodium hydroxide.
- Saponification emulsion; water, sodium hydroxide, cyclohexane, cyclohexanone, cyclohexanol, light and heavy oxidized, peroxides, monocarboxylic acids, dicarboxylic acids, esters, butanol, pentanol, cyclopentanone, cyclopentanol, 2-pentanone, cyclohexenone, cyclohexene, methylcyclopentanone, methylcyclopentanol, heptanones, methylheptanone, cyclohexanedione, cyclohexanediol, methylcyclohexanols, ethers.
- Sodium salts; sodium hydroxide, sodium salts.
- Saponified product; sodium hydroxide, cyclohexanone, cyclohexanol, light oxidized.
- Cx I recycle; cyclohexanone, cyclohexanol, light oxides.
- KA-Oil; cyclohexanone, cyclohexanol, oxides, alcohols, aldehydes and ketones.
- Purified cyclohexanone; butanol, pentanol, cyclopentanol, cyclopentanone, 5-hexenal, hexanal, 2-hexanone, cyclohexanone, cyclohexanol, 2-cyclohexen-1-one, heptanones, methylcyclohexanones, butylcyclohexane, cyclohexyl-butyl-ether.
- Residue from the purification of cyclohexanone; cyclohexanol, 2-cyclohexen-1-one, 2-cyclohexen-1-ol, heptanones, methylcyclohexanones, butylcyclohexane, cyclohexyl-butyl-ether, cyclohexene oxides, cyclohexylidene-cyclohexanone, cyclohexanone oligo mers, pentylcyclohexane, cyclohexyl acetate, other light/heavy condensation products.
- Heavy-residue; cyclohexylidene-cyclohexanone, cyclohexanone oligomers, heavy condensation products.
- Cyclohexanol for dehydrogenation; cyclohexanone, cyclohexanol, 2-cyclohexen-1-one, 2-cyclohexen-1-ol, heptanones, methylcyclohexanones, butylcyclohexane, cyclohexyl-butyl-ether, cyclohexene oxides, cyclohexylidene-cyclohexanone, cyclohexa-none oligomers, n-pentylcyclohexane, cyclohexyl acetate, other light/heavy condensation products.
- Cyclohexanol recycle; cyclopentanol, hexanal, 2-hexanone, cyclohexanone, cyclo-hexanol, cyclohexenone, cyclohexenol, heptanones, methylcyclohexanone, cyclohexyl-butyl ether.
- Hydrogen.
Appendix B. Compounds Involved in the Production Process of Cyclohexanone
No. | Compound | Formula | Chemical Structure | CAS# |
1 | acetic acid | C2H4O2 | 64-19-7 | |
2 | 1,1′-bicyclohexyl | C12H22 | 92-51-3 | |
3 | [1,1′-bicyclohexyl]-2,3′-dione | C12H18O2 | 55265-34-4 | |
4 | 1-butanol | C4H10O | 71-36-3 | |
5 | butoxycyclohexane | C10H20O | 24072-44-4 | |
6 | butylcyclohexane | C10H20 | 1678-93-9 | |
7 | 2-butylcyclohexanone | C10H18O | 1126-18-7 | |
8 | cycloheptanone | C7H12O | 502-42-1 | |
9 | 1,2-cyclohexanediol | C6H12O2 | 931-17-9 | |
10 | 1,3-cyclohexanedione | C6H8O2 | 504-02-9 | |
11 | cyclohexanol | C6H12O | 108-93-0 | |
12 | cyclohexanone | C6H10O | 108-94-1 | |
13 | 2-cyclohexen-1-ol | C6H8O | 822-67-3 | |
14 | 2-cyclohexen-1-one | C6H8O | 930-68-7 | |
15 | 1-(1-cyclohexen-1-yl)-2-propanone | C9H14O | 768-50-3 | |
16 | cyclohexene | C6H10 | 110-83-8 | |
17 | cyclohexyl acetone | C9H16O | 103-78-6 | |
18 | cyclohexyl butanoate | C10H18O2 | 1551-44-6 | |
19 | cyclohexyl ethanone | C8H14O | 823-76-7 | |
20 | cyclohexyl ethanoate | C8H14O2 | 622-45-7 | |
21 | cyclohexyl ether | C12H22O | 4645-15-2 | |
22 | cyclohexyl hexanoate | C12H22O2 | 6243-10-3 | |
23 | cyclohexyl pentanoate | C11H20O2 | 1551-43-5 | |
24 | 2-cyclohexylidencyclohexanone | C12H18O | 1011-12-7 | |
25 | cyclopentanol | C5H10O | 96-41-3 | |
26 | cyclopentanone | C7H8O | 120-92-3 | |
27 | 3,3-dimethylhexane | C8H18 | 563-16-6 | |
28 | 4-(1,1-dimethylpropyl)cyclohexanone | C11H20O | 16587-71-6 | |
29 | 2-ethylidenecyclohexanone | C8H12O | 1122-25-4 | |
30 | formic acid | CH2O2 | 64-18-6 | |
31 | 2-heptanone | C7H14O | 110-43-0 | |
32 | 3-heptanone | C7H14O | 106-35-4 | |
33 | hexanal | C6H12O | 66-25-1 | |
34 | 2-hexanone | C6H12O | 591-78-6 | |
35 | 5-hexenal | C6H10O | 764-59-0 | |
36 | 1-methoxycyclohexane | C7H14O | 931-56-6 | |
37 | 5-methyl-2-isopropylidenecyclohexanone | C10H16O | 15932-80-6 | |
38 | 2-methyl-3-heptanone | C8H16O | 13019-20-0 | |
39 | methylcyclohexane | C7H14 | 108-87-2 | |
40 | 2-methylcyclohexanone | C7H12O | 583-60-8 | |
41 | 3-methylcyclohexanone | C7H12O | 591-24-2 | |
42 | methylcyclopentane | C6H12 | 96-37-7 | |
43 | 1-methylcyclopentanol | C6H12O | 1462-03-9 | |
44 | (1-methylethyl)cyclohexane | C9H18 | 696-29-7 | |
45 | 2-methylcyclopentanone | C6H10O | 1120-72-5 | |
46 | 1-pentanol | C5H12O | 71-41-0 | |
47 | 2-pentanone | C5H10O | 107-87-9 | |
48 | 3-pentyl-1-cyclohexene | C11H20 | 15232-92-5 | |
49 | pentylcyclohexane | C11H22 | 4292-92-6 | |
50 | phenol | C6H6O | 108-95-2 | |
51 | p-tert-butylcyclohexanol | C10H20O | 98-52-2 | |
52 | 2-tetrahydrofurylmethanol | C5H10O2 | 97-99-4 | |
53 | 1,2,3,4-tetrahydronaphthalene | C10H12 | 119-64-2 | |
54 | toluene | C7H8 | 108-88-3 |
Appendix C. Mathematics of the Joback Method
Property | Parameter | Equation |
---|---|---|
Boiling temperature/K | ||
Melting temperature/K | ||
Critical temperature/K | ||
Critical pressure/bar | ||
Critical volume/cm3·mol−1 | ||
Gibbs energy of formation/kJ·kmol−1 | ||
Enthalpy of formation/kJ·kmol−1 | ||
Enthalpy of vaporization/kJ·kmol−1 | ||
Enthalpy of melting/kJ·kmol−1 | ||
Isobaric thermal capacity/kJ·kmol−1·K−1 | ; ; |
No. | Compound | K | K | Tc K | pc bar | vc m3/kmol | cp (298 K) J/(molK) | ||||
---|---|---|---|---|---|---|---|---|---|---|---|
1 | acetic acid | 390.7 | 272.9 | 587.3 | 57.31 | 0.171 | −434.8 | −377.9 | 40.67 | 11.08 | 65.7 |
2 | 1,1′-bicyclohexyl | 544.3 | 262.8 | 782.6 | 27.35 | 0.587 | −320.5 | 0.8 | 47.85 | 16.39 | 275.0 |
3 | [1,1′-bicyclohexyl]-2,3′-dione | 648.7 | 376.2 | 909.1 | 27.99 | 0.588 | −457.8 | −146.1 | 63.11 | 9.53 | 219.2 |
4 | 1-butanol | 406.7 | 190.1 | 571.1 | 39.76 | 0.344 | −354.6 | −198.0 | 43.25 | 12.87 | 138.0 |
5 | butoxycyclohexane | 470.2 | 232.1 | 665.9 | 25.25 | 0.547 | −327.6 | −47.2 | 40.69 | 14.68 | 238.0 |
6 | butylcyclohexane | 447.8 | 209.8 | 644.6 | 25.69 | 0.529 | −195.4 | 57.8 | 38.28 | 13.49 | 223.0 |
7 | 2-butylcyclohexanone | 515.6 | 278.1 | 729.1 | 26.63 | 0.536 | −333.1 | −64.8 | 42.53 | 13.00 | 228.0 |
8 | cycloheptanone | 455.9 | 245 | 689.2 | 39.46 | 0.361 | −257.0 | −94.5 | 36.33 | 2.06 | 123.0 |
9 | 1,2-cyclohexanediol | 502.8 | 358.9 | 720.4 | 34.8 | 0.342 | −464.9 | −273.6 | 53.77 | 16.55 | 195.0 |
10 | 1,3-cyclohexanedione | 496.5 | 305.4 | 743.3 | 45.29 | 0.319 | −367.9 | −213.3 | 48.19 | 1.08 | 114.7 |
11 | cyclohexanol | 431.9 | 264 | 654.6 | 49.25 | 0.270 | −278.7 | −120.9 | 41.73 | 9.30 | 147.0 |
12 | cyclohexanone | 428.7 | 237.2 | 656.0 | 43.23 | 0.313 | −230.2 | −90.8 | 33.94 | 1.57 | 105.0 |
13 | 2-cyclohexen-1-ol | 431.0 | 264.7 | 656.2 | 62.89 | 0.257 | −220.9 | −90.9 | 42.02 | 10.53 | 140.0 |
14 | 2-cyclohexen-1-one | 427.9 | 238 | 654.8 | 45.35 | 0.299 | −172.4 | −60.8 | 34.23 | 2.79 | 97.5 |
15 | 1-(1-cyclohexen-1-yl)-2-propanone | 488.6 | 271.8 | 707.4 | 34.04 | 0.458 | −180.8 | 12.0 | 43.46 | 14.40 | 190.0 |
16 | cyclohexene | 360.1 | 169.8 | 566.9 | 43.28 | 0.292 | −34.7 | 61.8 | 29.98 | 3.28 | 92.6 |
17 | cyclohexylacetone | 478.7 | 248.5 | 689.0 | 30.39 | 0.479 | −287.4 | −79.6 | 42.80 | 12.50 | 201.0 |
18 | cyclohexyl butanoate | 506.0 | 252.2 | 708.4 | 25.82 | 0.555 | −512.7 | −252.6 | 45.69 | 17.86 | 239.0 |
19 | cyclohexylethanone | 455.9 | 237.2 | 669.2 | 33.88 | 0.423 | −266.7 | −88.0 | 40.58 | 9.91 | 178.0 |
20 | cyclohexyl ethanoate | 460.2 | 229.1 | 668.4 | 41.52 | 0.443 | −471.4 | −269.4 | 40.94 | 14.44 | 169.0 |
21 | cyclohexyl ether | 544.3 | 262.8 | 782.6 | 26.46 | 0.587 | −320.5 | 0.8 | 47.85 | 16.39 | 275.0 |
22 | cyclohexyl hexanoate | 551.7 | 274.7 | 748.6 | 21.43 | 0.667 | −554.0 | −235.8 | 50.14 | 23.04 | 285.0 |
23 | cyclohexyl pentanoate | 528.9 | 263.4 | 728.5 | 23.47 | 0.611 | −533.3 | −244.2 | 47.92 | 20.45 | 262.0 |
24 | 2-cyclohexylidencyclohexanone | 621.1 | 362.1 | 872.0 | 27.33 | 0.606 | −235.8 | 43.5 | 59.44 | 11.56 | 220.1 |
25 | cyclopentanol | 404.7 | 256.2 | 621.0 | 54.55 | 0.223 | −251.9 | −117.2 | 39.33 | 8.81 | 129.0 |
26 | cyclopentanone | 401.6 | 229.5 | 622.3 | 47.56 | 0.265 | −203.4 | −87.1 | 31.54 | 1.08 | 87.0 |
27 | 3,3-dimethylhexane | 379.2 | 182.3 | 553.4 | 25.85 | 0.473 | −217.2 | 19.3 | 34.77 | 14.67 | 184.0 |
28 | 4-(1,1-dimethylpropyl)cyclohexanone | 535.2 | 291.8 | 758.9 | 24.63 | 0.581 | −362.5 | −53.6 | 46.13 | 13.79 | 251.0 |
29 | 2-ethylidenecyclohexanone | 481.1 | 270.1 | 709.8 | 35.26 | 0.408 | −195.5 | −28.5 | 39.62 | 7.07 | 142.0 |
30 | formic acid | 363.1 | 203.8 | 534.4 | 75.88 | 0.127 | −301.8 | −278.6 | 43.65 | 4.72 | 46.1 |
31 | 2-heptanone | 413.4 | 218.58 | 590.0 | 29.96 | 0.434 | −300.4 | −120.9 | 39.08 | 15.49 | 167.3 |
32 | 3-heptanone | 413.4 | 218.58 | 590.0 | 29.96 | 0.434 | −300.4 | −120.9 | 39.08 | 15.49 | 167.3 |
33 | hexanal | 385.3 | 198.9 | 557.8 | 36.47 | 0.389 | −252.8 | −99.9 | 35.37 | 15.35 | 148.0 |
34 | 2-hexanone | 390.6 | 206.8 | 568.1 | 35.99 | 0.378 | −279.8 | −129.3 | 35.30 | 14.66 | 144.0 |
35 | 5-hexenal | 382.0 | 197.1 | 558.1 | 35.52 | 0.370 | −127.3 | −12.0 | 34.70 | 14.07 | 137.0 |
36 | 1-Methoxycyclohexane | 374.4 | 190.5 | 569.6 | 33.53 | 0.331 | −238.9 | −68.8 | 31.62 | 6.42 | 151.0 |
37 | 5-methyl-2-isopropylidenecyclohexanone | 522.1 | 274.5 | 755.1 | 27.58 | 0.520 | −266.9 | −27.9 | 43.40 | 12.01 | 219.0 |
38 | 2-methyl-3-heptanone | 435.8 | 214.8 | 615.2 | 27.27 | 0.483 | −326.3 | −114.8 | 40.96 | 14.55 | 189.2 |
39 | Methylcyclohexane | 379.1 | 176 | 581.6 | 35.22 | 0.361 | −133.5 | 32.5 | 31.61 | 5.72 | 155.0 |
40 | 2-methylcyclohexanone | 352.0 | 168.28 | 546.9 | 38.39 | 0.313 | −106.7 | 36.2 | 29.40 | 5.23 | 112.6 |
41 | 3-methylcyclohexanone | 352.0 | 168.28 | 546.9 | 38.39 | 0.313 | −106.7 | 36.2 | 29.40 | 5.23 | 112.6 |
42 | 1-methylcyclopentanol | 427.8 | 291.4 | 651.6 | 50.66 | 0.277 | −257.3 | −114.3 | 40.41 | 5.11 | 121.0 |
43 | 2-methylcyclopentanone | 419.8 | 236.5 | 637.4 | 40.11 | 0.320 | −244.4 | −86.4 | 37.61 | 4.74 | 117.5 |
44 | (1-methylethyl)cyclohexane | 424.4 | 183.6 | 628.2 | 28.63 | 0.467 | −180.1 | 46.9 | 35.67 | 7.38 | 200.0 |
45 | methylcyclopentanone | 351.9 | 168.2 | 546.9 | 38.39 | 0.312 | −106.6 | 36.1 | 29.40 | 5.23 | 111.7 |
46 | 1-pentanol | 406.0 | 206.9 | 567.6 | 38.77 | 0.335 | −298.8 | −145.6 | 43.40 | 12.79 | 131.0 |
47 | 2-pentanone | 367.6 | 196 | 545.9 | 37.41 | 0.321 | −259.1 | −137.7 | 33.96 | 10.30 | 120.7 |
48 | 3-pentyl-1-cyclohexene | 469.8 | 221.9 | 666.3 | 24.19 | 0.571 | −158.3 | 96.2 | 40.80 | 17.30 | 239.0 |
49 | pentylcyclohexane | 470.6 | 221.1 | 665.2 | 23.36 | 0.585 | −216.1 | 66.2 | 40.51 | 16.08 | 246.0 |
50 | phenol | 439.0 | 283 | 671.0 | 59.26 | 0.230 | −96.5 | −32.9 | 43.58 | 11.51 | 95.2 |
51 | p-tert-butylcyclohexanol | 523.6 | 271.8 | 729.8 | 25.77 | 0.576 | −270.8 | −32.7 | 50.04 | 18.90 | 214.3 |
52 | 2-tetrahydrofurylmethanol | 449.3 | 235.8 | 635.2 | 48.29 | 0.315 | −399.6 | −227.7 | 48.45 | 14.06 | 125.0 |
53 | 1,2,3,4-tetrahydronaphthalene | 475.5 | 260.1 | 708.1 | 35.69 | 0.438 | 62.3 | 192.5 | 41.19 | 10.27 | 144.0 |
54 | toluene | 386.2 | 195.1 | 597.8 | 41.14 | 0.320 | 48.7 | 120.5 | 33.45 | 7.93 | 102.0 |
Appendix D. Mathematics of the Marrero–Gani Method
Property | f= | Right-Hand Side of Equation (A1) |
---|---|---|
Melting temperature/K | ||
Boiling temperature/K | ||
Critical temperature/K | ||
Critical pressure/bar | ||
Critical volume/cm3·mol−1 | ||
Gibbs energy of formation/kJ·kmol−1 | ||
Enthalpy of formation/kJ·kmol−1 | ||
Enthalpy of vaporization/kJ·kmol−1 | ||
Enthalpy of melting/kJ·kmol−1 |
Generic Constants | |
---|---|
/K | 147.450 |
/K | 222.543 |
Tc0/K | 231.239 |
pc1/bar | 5.9827 |
pc2/bar−0.5 | 0.108998 |
vc0/cm3·mol−1 | 7.95 |
/kJ·mol−1 | −34.967 |
/kJ·mol−1 | 5.549 |
/kJ·mol−1 | 11.733 |
/kJ·mol−1 | −2.806 |
No. | Compound | K | Tc K | pc bar | vc m3/kmol | |||||
---|---|---|---|---|---|---|---|---|---|---|
1 | acetic acid | 397.3 | 308.4 | 646.20 | 58.88 | 0.159 | −369.2 | −426.9 | 28.95 | 9.55 |
2 | 1,1′-bicyclohexyl | 511.7 | 271.7 | 727.00 | 25.60 | 0.598 | 42.6 | −272.0 | 57.98 | 12.91 |
3 | [1,1′-bicyclohexyl]-2,3′-dione | 579.8 | 354.2 | 867.22 | 30.29 | 0.599 | −528.3 | −229.8 | 85.54 | 23.04 |
4 | 1-butanol | 381.7 | 213.0 | 553.80 | 43.70 | 0.276 | −277.8 | −151.9 | 50.83 | 10.93 |
5 | Butoxycyclohexane | 464.5 | 231.5 | 676.94 | 22.89 | 0.610 | −40.9 | −357.0 | 59.80 | 19.52 |
6 | butylcyclohexane | 454.1 | 199.4 | 650.20 | 25.40 | 0.533 | 70.0 | −200.3 | 49.37 | 13.49 |
7 | 2-Butylcyclohexanone | 493.3 | 286.4 | 762.27 | 27.58 | 0.544 | −105.3 | −366.3 | 63.58 | 19.70 |
8 | cycloheptanone | 451.7 | 278.9 | 734.20 | 41.37 | 0.361 | −111.9 | −286.1 | 48.90 | 9.75 |
9 | 1,2-cyclohexanediol | 504.2 | 349.0 | 714.14 | 44.00 | 0.341 | −263.8 | −466.5 | 90.63 | 16.06 |
10 | 1,3-cyclohexanedione | 493.4 | 331.6 | 807.20 | 51.56 | 0.312 | −295.2 | −429.1 | 58.73 | 13.74 |
11 | cyclohexanol | 434.0 | 287.8 | 650.00 | 42.60 | 0.322 | −109.5 | −286.2 | 61.20 | 9.84 |
12 | cyclohexanone | 431.2 | 265.7 | 715.26 | 45.93 | 0.312 | −125.2 | −267.5 | 45.56 | 8.68 |
13 | 2-cyclohexen-1-ol | 437.2 | 288.9 | 648.32 | 45.39 | 0.307 | −49.6 | −189.2 | 62.29 | 8.88 |
14 | 2-cyclohexen-1-one | 443.2 | 267.8 | 714.00 | 49.12 | 0.297 | −59.2 | −183.0 | 53.06 | 10.23 |
15 | 1-(1-cyclohexen-1-yl)-2-propanone | 470.7 | 262.3 | 685.83 | 31.52 | 0.460 | −27.4 | −205.9 | 52.37 | 14.73 |
16 | cyclohexene | 356.1 | 183.6 | 558.00 | 43.92 | 0.289 | 104.7 | −8.9 | 32.86 | 2.66 |
17 | cyclohexylacetone | 473.7 | 266.4 | 679.01 | 29.83 | 0.483 | −75.0 | −301.2 | 54.96 | 15.75 |
18 | cyclohexyl butanoate | 486.2 | 237.2 | 683.41 | 25.83 | 0.545 | −245.5 | −543.1 | 61.08 | 18.83 |
19 | cyclohexylethanone | 453.7 | 278.5 | 662.05 | 33.33 | 0.427 | −83.1 | −280.4 | 49.43 | 13.11 |
20 | cyclohexyl ethanoate | 441.0 | 225.4 | 639.90 | 31.20 | 0.448 | −481.9 | −267.1 | 53.53 | 12.88 |
21 | cyclohexyl ether | 515.7 | 281.6 | 732.56 | 26.16 | 0.608 | −3.9 | −342.5 | 64.85 | 16.71 |
22 | cyclohexyl hexanoate | 515.7 | 257.9 | 727.13 | 20.21 | 0.713 | −221.3 | −605.5 | 75.81 | 26.75 |
23 | cyclohexyl pentanoate | 497.7 | 244.4 | 698.92 | 23.63 | 0.601 | −237.4 | −563.9 | 65.99 | 21.47 |
24 | 2-cyclohexylidencyclohexanone | 565.4 | 323.2 | 783.20 | 31.56 | 0.501 | −72.1 | −341.8 | 58.93 | 12.95 |
25 | cyclopentanol | 413.4 | 275.3 | 622.23 | 47.41 | 0.273 | −122.8 | −267.6 | 57.86 | 11.73 |
26 | cyclopentanone | 403.8 | 251.1 | 694.64 | 51.44 | 0.262 | −138.5 | −248.9 | 42.22 | 7.61 |
27 | 3,3-dimethylhexane | 385.1 | 187.3 | 555.14 | 25.68 | 0.466 | 17.2 | −217.9 | 38.06 | 10.52 |
28 | 4-(1,1-dimethylpropyl)cyclohexanone | 503.9 | 298.3 | 776.91 | 27.06 | 0.575 | −90.3 | −392.6 | 65.55 | 16.86 |
29 | 2-ethylidenecyclohexanone | 478.4 | 276.7 | 737.22 | 33.74 | 0.448 | −47.1 | −211.7 | 63.55 | 11.38 |
30 | formic acid | 362.8 | 259.4 | 554.90 | 83.20 | 0.102 | −279.9 | −303.6 | 48.32 | 13.31 |
31 | 2-heptanone | 426.7 | 223.8 | 611.13 | 29.34 | 0.417 | −300.8 | −122.0 | 46.38 | 17.58 |
32 | 3-heptanone | 417.1 | 227.2 | 596.91 | 29.44 | 0.418 | −305.0 | −125.4 | 46.29 | 17.26 |
33 | hexanal | 407.6 | 228.8 | 591.00 | 33.10 | 0.373 | −251.1 | −100.7 | 43.90 | 20.10 |
34 | 2-hexanone | 400.8 | 215.1 | 589.20 | 32.47 | 0.373 | −278.6 | −127.6 | 41.82 | 14.20 |
35 | 5-hexenal | 405.6 | 232.5 | 594.10 | 34.76 | 0.359 | −128.8 | −14.9 | 42.80 | 17.07 |
36 | 1-Methoxycyclohexane | 408.2 | 203.4 | 607.23 | 32.33 | 0.406 | −63.2 | −279.8 | 37.51 | 10.73 |
37 | 5-methyl-2-isopropylidenecyclohexanone | 497.2 | 299.0 | 753.09 | 28.05 | 0.558 | −33.8 | −255.2 | 77.19 | 11.98 |
38 | 2-methyl-3-heptanone | 431.2 | 233.0 | 613.20 | 26.78 | 0.470 | −122.8 | −334.2 | 49.16 | 16.81 |
39 | Methylcyclohexane | 374.2 | 182.4 | 577.23 | 35.07 | 0.370 | 44.6 | −137.8 | 35.17 | 6.74 |
40 | 2-methylcyclohexanone | 448.3 | 266.3 | 723.99 | 38.52 | 0.370 | −299.4 | −125.3 | 48.95 | 11.81 |
41 | 3-methylcyclohexanone | 448.3 | 266.3 | 723.99 | 38.52 | 0.370 | −299.4 | −125.3 | 48.95 | 11.81 |
42 | 1-methylcyclopentanol | 409.2 | 283.5 | 580.05 | 44.29 | 0.325 | −142.0 | −313.4 | 57.35 | 5.99 |
43 | 2-methylcyclopentanone | 422.4 | 251.8 | 704.16 | 42.52 | 0.321 | −280.8 | −138.6 | 45.61 | 10.74 |
44 | (1-methylethyl)cyclohexane | 427.9 | 191.4 | 621.05 | 28.42 | 0.481 | 57.3 | −196.4 | 43.00 | 11.32 |
45 | methylcyclopentanone | 340.4 | 155.8 | 538.30 | 38.44 | 0.313 | 31.3 | −119.2 | 31.83 | 5.64 |
46 | 1-pentanol | 410.9 | 221.5 | 580.32 | 38.12 | 0.332 | −143.9 | −298.6 | 55.80 | 14.20 |
47 | 2-pentanone | 362.1 | 210.4 | 544.80 | 37.06 | 0.306 | −141.6 | −263.3 | 36.47 | 11.98 |
48 | 3-pentyl-1-cyclohexene | 473.2 | 180.7 | 652.99 | 25.51 | 0.559 | 128.8 | −109.7 | 59.95 | 16.49 |
49 | pentylcyclohexane | 476.9 | 208.7 | 668.01 | 23.27 | 0.590 | 78.0 | −221.2 | 54.28 | 16.13 |
50 | phenol | 455.0 | 308.0 | 687.06 | 59.65 | 0.271 | −32.6 | −94.3 | 64.25 | 15.36 |
51 | p-tert-butylcyclohexanol | 494.8 | 240.6 | 694.60 | 24.12 | 0.595 | 216.4 | −43.5 | 58.23 | 13.72 |
52 | 2-tetrahydrofurylmethanol | 451.2 | 258.3 | 641.69 | 48.15 | 0.305 | −239.0 | −399.2 | 64.17 | 14.14 |
53 | 1,2,3,4-tetrahydronaphthalene | 480.8 | 241.7 | 664.03 | 31.37 | 0.521 | 110.1 | −61.3 | 77.10 | 11.86 |
54 | toluene | 383.8 | 202.1 | 604.05 | 42.18 | 0.317 | 123.6 | 50.6 | 38.43 | 9.90 |
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Compounds | Groups | Nk | |||
---|---|---|---|---|---|
Cyclohexene | –CH2– | 4 | 0.0100 | 0.0025 | 48 |
=CH– | 2 | 0.0082 | 0.0011 | 41 | |
total: | 0.0564 | 0.0122 | 274 | ||
estimated→ | Tc/K = 567 | pc/bar = 43.3 | vc/cm3·mol−1 = 291 | ||
from ref. [16] | Tc/K = 560.4 | pc/bar = 48.41 | vc/cm3·mol−1 = 377.4 | ||
2-Cyclohexen-1-one | –CH2– | 3 | 0.0100 | 0.0025 | 48 |
=CH– | 2 | 0.0082 | 0.0011 | 41 | |
>C=O | 1 | 0.0284 | 0.0028 | 55 | |
total: | 0.0784 | 0.0125 | 281 | ||
estimated→ | Tc/K = 655 | pc/bar = 45.3 | vc/cm3·mol−1 = 298 | ||
from ref. [17] | Tc/K = 685.0 | pc/bar = 45.30 | vc/cm3·mol−1 = 304.9 |
Compounds | Groups | j | Nk | |||
---|---|---|---|---|---|---|
Cyclohexene | CH2 (cyc) | 1º | 4 | 1.8815 | 0.009884 | 49.24 |
CH=CH (cyc) | 1º | 1 | 3.6426 | 0.013815 | 83.91 | |
total: | 11.1686 | 0.053351 | 280.87 | |||
estimated→ | Tc/K = 558 | pc/bar = 43.9 | vc/cm3·mol−1 = 289 | |||
from ref. [16] | Tc/K = 560.4 | pc/bar = 48.41 | vc/cm3·mol−1 = 377.4 | |||
2-Cyclohexen-1-one | CH2 (cyc) | 1º | 3 | 1.8815 | 0.009884 | 49.24 |
CH=CH (cyc) | 1º | 1 | 3.6426 | 0.013815 | 83.91 | |
CO (cyc) | 1º | 1 | 12.6396 | −0.000207 | 57.38 | |
total: | 21.9267 | 0.043260 | 289.01 | |||
estimated→ | Tc/K = 714 | pc/bar = 49 | vc/cm3·mol−1 = 297 | |||
from ref. [17] | Tc/K = 685.0 | pc/bar = 45.30 | vc/cm3·mol−1 = 304.9 |
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Fernández, L.; Ortega, J.; Domínguez, L.; Lorenzo, D.; Santos, A.; Romero, A. Using Two Group-Contribution Methods to Calculate Properties of Liquid Compounds Involved in the Cyclohexanone Production Operations. Liquids 2022, 2, 413-431. https://doi.org/10.3390/liquids2040024
Fernández L, Ortega J, Domínguez L, Lorenzo D, Santos A, Romero A. Using Two Group-Contribution Methods to Calculate Properties of Liquid Compounds Involved in the Cyclohexanone Production Operations. Liquids. 2022; 2(4):413-431. https://doi.org/10.3390/liquids2040024
Chicago/Turabian StyleFernández, Luis, Juan Ortega, Leandro Domínguez, David Lorenzo, Aurora Santos, and Arturo Romero. 2022. "Using Two Group-Contribution Methods to Calculate Properties of Liquid Compounds Involved in the Cyclohexanone Production Operations" Liquids 2, no. 4: 413-431. https://doi.org/10.3390/liquids2040024