Instituto Politécnico Nacional

Escuela Superior de Ingeniería Química e

Industrias Extractivas
Departamento de Ingeniería Química Petrolera

Química del petróleo y catálisis

Actividad 2. Estructuras de compuestos orgánicos en

el petróleo y sus productos

Grupo: 2PM51

Alumno:
Borgonio López Andrés Uriel

Profesor:
Sotelo Boyas Rogelio

1
 Índice
1. Dibuja 10 diferentes biomarcadores……………………………………………3
2. Dibuja 10 diferentes hidrocarburos alifáticos………………………………….5
3. Dibuja 5 Isoparafinas que se encuentran en la gasolina…………………….7
4. Dibuja 5 compuestos de nitrógeno que se encuentran en la turbosina……8
5. Dibuja 5 diferentes hidrocarburos aromáticos que se encuentran el diésel y
5 aromáticos que se encuentran en la gasolina………………………………9
6. Dibuja 10 diferentes productos petroquímicos secundarios……………….11
7. Dibuja 5 moléculas de compuestos que conforman un lubricante……….13
8. Para dos hidrocarburos de cada tipo de los incisos 1 a 6: obtenga
(directamente de Chemoffice) sus propiedades físicas y químicas más
relevantes y lístelos en forma de tabla. ……………………………………...15

2
1.- Dibuja 10 diferentes biomarcadores

Hexadecane

OH

3,7,11,15-Tetramethyl-hexadec-2-en-1-ol
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain

2,6,10,14-Tetramethyl-pentadecane
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain

2,6,10,14-Tetramethyl-hexadecane
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain
CH3 CH3
OH
O

17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-
one

3
 H3C

CH3
CH3

CH3 H3C

HO
17-(1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-
1H-cyclopenta[a]phenanthren-3-ol
O H
N

O
HN

O
HN

NH2
(2,5-Dioxo-imidazolidin-4-yl)-urea
HO CH3

HN

H3C OH
5-(1-Hydroxy-2-methylamino-ethyl)-2-methoxy-phenol
CH3 CH3
H3C CH3

OH

CH3
3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol
CH2

H3C

CH3
4-Isopropenyl-1-methyl-cyclohexene

4
2.- Dibuja 10 diferentes hidrocarburos alifáticos
H2 H2 H2
C C C
H3C CH C CH3
H2

H2C
CH3
3-Ethyl-heptane
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain
CH3
H2C
H2 H
C C CH
H3C C C CH3
H2 H
3-Methyl-oct-4-ene
CH3
H2C
H2
CH C C
H3C C C CH3
H2
6-Methyl-oct-3-yne

Cyclopentane

Cyclopentene

Cyclopent-1-yne

5
 Ethyl-cyclopentane

Methyl-cyclobutane

Propyl-cyclohexane
CH3

CH3 CH3

H3C CH3

H3C CH3
3,5-Diethyl-2,6-dimethyl-4-propyl-hept-2-ene
#3: Please note: Alphabetic order of prefixes ignored while selecting
parent chain

6
3.- Dibuja 5 Isoparafinas que se encuentran en la gasolina
CH3 CH3

H3C CH3
2,4-Dimethyl-pentane
#3: Please note: Alphabetic order of prefixes ignored while
selecting parent chain
CH3

H3C
CH3

CH3
2,5-Dimethyl-hexane
#3: Please note: Alphabetic order of prefixes ignored while selecting
parent chain
CH3 CH3
CH3

H3C CH3
2,2,4-Trimethyl-pentane
#3: Please note: Alphabetic order of prefixes ignored while
selecting parent chain
CH3
H3C

CH3
H3C
2,2-Dimethyl-propane
#3: Please note: Alphabetic order of prefixes ignored while
selecting parent chain
H3C CH3

CH3
Isobutane

7
4.- Dibuja 5 compuestos de nitrógeno que se encuentran en la turbosina

Dibenzo[c,h]acridine
NH2

Phenylamine

2,3-Dihydro-1H-indole

H
9H-Carbazole

N
H

11H-Benzo[a]carbazole

8
5.- Dibuja 5 diferentes hidrocarburos aromáticos que se encuentran el diésel

HO
Naphthalen-2-ol

Anthracene

Acenaphthene

Naphthalene

Chrysene

9
5.- 5 aromáticos que se encuentran en la gasolina

Benzene
CH3

Toluene
CH3

H3C
m-Xylene

Benzo[a]anthracene

1,3-Dihydro-benzo[ghi]perylene

10
6.- Dibuja 10 diferentes productos petroquímicos secundarios

CH2
Vinyl-benzene

H3C CH3

p-Xylene
H3C

H3C
o-Xylene
O

H3C
H
Propionaldehyde
OH

H3C CH3
Propan-2-ol

H3C
O
2-Methyl-oxirane
H3C

H3C
Isopropyl-benzene

11
 NO2

Nitro-benzene

Cyclohexane

Cl

Chloro-benzene

12
7.- Dibuja 5 moléculas de compuestos que conforman un lubricante.
Ftalatos
O CH3 CH3
CH3

O CH3

O CH3

CH3
O CH3 CH3

Phthalic acid bis-(3,5,5-trimethyl-hexyl) ester

CH3 H3C

O O

H3C O O CH3

Phthalic acid bis-(2-ethyl-hexyl) ester

Trimelitatos

O O

O O
Benzene-1,2,4-tricarboxylic acid tris-(2-ethyl-hexyl) ester

13
Esteres de poliol
CH3
HO

H3C CH3
2,2-Dimethyl-propan-1-ol
HO

HO

OH
HO
2,2-Bis-hydroxymethyl-propane-1,3-diol

14
8.- Para dos hidrocarburos de cada tipo de los incisos 1 a 6: obtenga
(directamente de Chemoffice) sus propiedades físicas y químicas más
relevantes y lístelos en forma de tabla.

8.1 Biomarcadores
HO CH3

HN

H3C OH
5-(1-Hydroxy-2-methylamino-ethyl)-2-methoxy-phenol
Boiling Point: 705.01 [K]
Melting Point: 473.33 [K] C10H15NO3
Critical Temp: 784.22 [K] Exact Mass: 197.11
Critical Pres: 38.25 [Bar] Mol. Wt.: 197.23
Critical Vol: 569.50 [cm3/mol] m/e: 197.11 (100.0%), 198.11 (11.5%), 199.11 (1.2%)
Gibbs Energy: -173.39 [kJ/mol] C, 60.90; H, 7.67; N, 7.10; O, 24.34
Log P: 0.55
MR: 54.52 [cm3/mol]
Henry's Law: 13.78
Heat of Form: -438.24 [kJ/mol]
CLogP: -0.2384
CMR: 5.3718

CH3 CH3
H3C CH3

OH

CH3
3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-1-ol

Boiling Point: 794.69 [K]

Melting Point: 384.32 [K] C20H30O
Critical Temp: 829.59 [K] Exact Mass: 286.23
Critical Pres: 15.12 [Bar] Mol. Wt.: 286.45
Critical Vol: 1013.50 [cm3/mol] m/e: 286.23 (100.0%), 287.23 (22.3%), 288.24 (2.5%)
Gibbs Energy: 314.14 [kJ/mol] C, 83.86; H, 10.56; O, 5.59
Log P: 4.69
MR: 98.70 [cm3/mol]
Henry's Law: 2.32
Heat of Form: -54.66 [kJ/mol]
CLogP: 6.403
CMR: 9.8341

15
8.2 Hidrocarburos alifáticos
CH3

CH3 CH3

H3C CH3

H3C CH3
3,5-Diethyl-2,6-dimethyl-4-propyl-hept-2-ene
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain

Boiling Point: 568.28 [K] C16H32

Melting Point: 191.58 [K] Exact Mass: 224.25
Critical Temp: 677.20 [K] Mol. Wt.: 224.43
Critical Pres: 14.05 [Bar] m/e: 224.25 (100.0%), 225.25 (17.8%), 226.26 (1.6%)
Critical Vol: 895.50 [cm3/mol] C, 85.63; H, 14.37
Gibbs Energy: 139.64 [kJ/mol]
Log P: 6.11
MR: 77.04 [cm3/mol]
Henry's Law: -2.61
Heat of Form: -291.77 [kJ/mol]
CLogP: 8.024
CMR: 7.5728

CH3
H2C
H2
CH C C
H3C C C CH3
H2
6-Methyl-oct-3-yne
Boiling Point: 414.08 [K] C9H16
Melting Point: 281.79 [K] Exact Mass: 124.13
Critical Temp: 611.09 [K] Mol. Wt.: 124.22
Critical Pres: 27.30 [Bar] m/e: 124.13 (100.0%), 125.13 (10.3%)
Critical Vol: 495.50 [cm3/mol] C, 87.02; H, 12.98
Gibbs Energy: 225.26 [kJ/mol]
Log P: 3.60
MR: 43.26 [cm3/mol]
Henry's Law: -0.26
Heat of Form: 37.93 [kJ/mol]
CLogP: 3.967
CMR: 4.2248

16
8.3 Isoparafinas que se encuentran en la gasolina

CH3 CH3

H3C CH3
2,4-Dimethyl-pentane
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain

Boiling Point: 358.88 [K] C7H16

Melting Point: 138.15 [K] Exact Mass: 100.13
Critical Temp: 501.81 [K] Mol. Wt.: 100.20
Critical Pres: 28.47 [Bar] m/e: 100.13 (100.0%), 101.13 (8.0%)
Critical Vol: 415.50 [cm3/mol] C, 83.91; H, 16.09
Gibbs Energy: 3.18 [kJ/mol]
Log P: 3.24
MR: 34.83 [cm3/mol]
Henry's Law: -1.97
Heat of Form: -198.37 [kJ/mol]
CLogP: 4.137
CMR: 3.424

CH3 CH3
CH3

H3C CH3
2,2,4-Trimethyl-pentane
#3: Please note: Alphabetic order of prefixes ignored while selecting parent chain

Boiling Point: 378.97 [K] C8H18

Melting Point: 166.84 [K] Exact Mass: 114.14
Critical Temp: 521.58 [K] Mol. Wt.: 114.23
Critical Pres: 26.06 [Bar] m/e: 114.14 (100.0%), 115.14 (8.9%)
Critical Vol: 466.50 [cm3/mol] C, 84.12; H, 15.88
Gibbs Energy: 16.88 [kJ/mol]
Log P: 3.72
MR: 39.23 [cm3/mol]
Henry's Law: -2.09
Heat of Form: -222.48 [kJ/mol]
CLogP: 4.536
CMR: 3.8878

17
8.4 Compuestos de nitrógeno que se encuentran en la turbosina

Dibenzo[c,h]acridine
Boiling Point: 851.32 [K] C21H13N
Melting Point: 592.25 [K] Exact Mass: 279.10
Critical Temp: 994.55 [K] Mol. Wt.: 279.33
Critical Pres: 25.85 [Bar] m/e: 279.10 (100.0%), 280.11 (23.6%), 281.11 (2.7%)
Critical Vol: 840.50 [cm3/mol] C, 90.29; H, 4.69; N, 5.01
Gibbs Energy: 713.11 [kJ/mol]
Log P: 5.53
MR: 90.51 [cm3/mol]
Henry's Law: 7.58
Heat of Form: 522.42 [kJ/mol]
CLogP: 5.761
CMR: 9.2295

NH2

Phenylamine
Boiling Point: 450.70 [K]
Melting Point: 266.56 [K] C6H7N
Critical Temp: 698.52 [K] Exact Mass: 93.06
Critical Pres: 50.59 [Bar] Mol. Wt.: 93.13
Critical Vol: 292.50 [cm3/mol] m/e: 93.06 (100.0%), 94.06 (6.8%)
Gibbs Energy: 178.50 [kJ/mol] C, 77.38; H, 7.58; N, 15.04
Log P: 0.90
MR: 30.10 [cm3/mol]
Henry's Law: 4.11
Heat of Form: 103.15 [kJ/mol]
CLogP: 0.915
CMR: 3.0573

18
8.5 Hidrocarburos aromáticos que se encuentran el diésel y aromáticos que se
encuentran en la gasolina

HO
Naphthalen-2-ol
Boiling Point: 554.68 [K]
Melting Point: 372.80 [K] C10H8O
Critical Temp: 807.61 [K] Exact Mass: 144.06
Critical Pres: 47.37 [Bar] Mol. Wt.: 144.17
Critical Vol: 425.50 [cm3/mol] m/e: 144.06 (100.0%), 145.06 (11.3%)
Gibbs Energy: 97.76 [kJ/mol] C, 83.31; H, 5.59; O, 11.10
Log P: 2.87
MR: 44.26 [cm3/mol]
Henry's Law: 5.65
Heat of Form: 0.56 [kJ/mol]
CLogP: 2.649
CMR: 4.5297

1,3-Dihydro-benzo[ghi]perylene

Boiling Point: 829.90 [K] C22H14

Melting Point: 589.00 [K] Exact Mass: 278.11
Critical Temp: 912.39 [K] Mol. Wt.: 278.35
Critical Pres: 23.98 [Bar] m/e: 278.11 (100.0%), 279.11 (24.5%), 280.12 (2.9%)
Critical Vol: 843.50 [cm3/mol] C, 94.93; H, 5.07
Gibbs Energy: 700.02 [kJ/mol]
Log P: 3.45
MR: 97.42 [cm3/mol]
Henry's Law: 2.88
Heat of Form: 499.89 [kJ/mol]
CLogP: 6.323
CMR: 9.3066

19
8.6 Productos petroquímicos secundarios

CH2
Vinyl-benzene

Boiling Point: 406.00 [K]

C8H8
Melting Point: 204.08 [K]
Exact Mass: 104.06
Critical Temp: 641.54 [K]
Mol. Wt.: 104.15
Critical Pres: 38.44 [Bar]
m/e: 104.06 (100.0%), 105.07 (9.0%)
Critical Vol: 356.50 [cm3/mol]
C, 92.26; H, 7.74
Gibbs Energy: 216.73 [kJ/mol]
Log P: 2.67
MR: 35.82 [cm3/mol]
Henry's Law: 0.95
Heat of Form: 153.51 [kJ/mol]
CLogP: 2.866
CMR: 3.6668

H3C
O
2-Methyl-oxirane

Boiling Point: 301.93 [K] C3H6O

Melting Point: 167.58 [K] Exact Mass: 58.04
Critical Temp: 486.15 [K] Mol. Wt.: 58.08
Critical Pres: 52.13 [Bar] m/e: 58.04 (100.0%), 59.05 (3.5%)
Critical Vol: 181.50 [cm3/mol] C, 62.04; H, 10.41; O, 27.55
Gibbs Energy: -50.99 [kJ/mol]
Log P: 0.16
MR: 15.61 [cm3/mol]
Henry's Law: 2.19
Heat of Form: -164.45 [kJ/mol]
CLogP: 0.247
CMR: 1.5445

20