Investigation of a Complex Reaction Pathway Network of Isobutane/2-Butene Alkylation by CGC–FID and CGC-MS-DS
Abstract
:1. Introduction
2. Results and Discussion
2.1. Optimization of the CGC-FID Analysis Conditions
2.2. Quantitative Analysis Results of the Peak Area Normalization Method
2.2.1. Relative Correction Factors
2.2.2. Comparison of the Peak Area Normalization Method and the Corrected Peak Area Normalization Method
2.2.3. Precision
2.2.4. Recovery
2.3. Chemical Composition of the C4 Alkylation Products
2.4. Alkylation Reaction Pathway Network
2.4.1. Changes in the Composition of the Reaction Process
2.4.2. Reaction Pathway Network Construction
3. Experimental Section
3.1. Materials
3.2. Experimental Equipment
3.3. Quantitative Analysis
3.3.1. CGC-FID Analysis Conditions
3.3.2. Determination of the Relative Correction Factors
3.3.3. Determining the Mass% of the SAMPLE Components
3.4. Qualitative Analysis
CGC-MS-DS Analysis Conditions
3.5. C4 Alkylation Reaction
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Component | Relative Correction Factors (fis) | |||
---|---|---|---|---|
1 | 2 | 3 | Mean Value | |
2,3-Dimethylbutane | 1.0381 | 1.0243 | 1.0040 | 1.02 |
2-Methylpentane | 1.0193 | 1.0236 | 1.0165 | 1.02 |
3-Methylpentane | 1.0121 | 0.9946 | 1.0057 | 1.00 |
2,4-Dimethylpentane | 1.0048 | 0.9717 | 1.0044 | 0.99 |
2,2,3-Trimethylbutane | 1.0402 | 1.0541 | 1.0479 | 1.05 |
2-Methylhexane | 0.9846 | 0.9856 | 1.0098 | 0.99 |
2,3-Dimethylpentane | 0.9939 | 0.9943 | 0.9846 | 0.99 |
3-Methylhexane | 1.0581 | 1.0351 | 1.0566 | 1.05 |
2,2,4-Trimethylpentane | 1.0000 | 1.0000 | 1.0000 | 1.00 |
2,4-Dimethylhexane | 1.0022 | 1.0076 | 0.9938 | 1.00 |
2,2,3-Trimethylpentane | 1.0070 | 1.0465 | 1.0610 | 1.04 |
2,3,4-Trimethylpentane | 1.0074 | 1.0017 | 1.0399 | 1.02 |
2,3-Dimethylhexane | 1.0389 | 1.0839 | 1.0848 | 1.07 |
3,4-Dimethylhexane | 1.0013 | 1.0356 | 1.0518 | 1.03 |
2,2,5-Trimethylhexane | 0.9701 | 0.9923 | 1.0096 | 0.99 |
Component | Serial Number | Initial Concentration (wt%) | Concentration Measurement for the Quantitative Analytical Method | |||
---|---|---|---|---|---|---|
Peak Area Normalization (wt%) | RD (%) | Corrected Peak Area Normalization (wt%) | RD (%) | |||
2,3-Dimethylbutane | 1 | 3.5872 | 3.5260 | 1.71 | 3.5563 | 1.02 |
2 | 8.0537 | 7.9519 | 1.26 | 8.0048 | 0.61 | |
3 | 4.4130 | 4.3533 | 1.35 | 4.3821 | 0.70 | |
2-Methylpentane | 1 | 5.6946 | 5.6813 | 0.23 | 5.7167 | 0.15 |
2 | 6.6314 | 6.6641 | 0.49 | 6.6959 | 0.93 | |
3 | 5.2425 | 5.1777 | 1.24 | 5.1999 | 0.81 | |
3-Methylpentane | 1 | 7.1512 | 7.0880 | 0.88 | 7.0226 | 1.99 |
2 | 5.0339 | 5.0358 | 0.04 | 5.0005 | 1.02 | |
3 | 6.7699 | 6.7055 | 0.95 | 6.6308 | 2.06 | |
2,4-Dimethylpentane | 1 | 4.9740 | 5.0375 | 1.28 | 4.9389 | 0.85 |
2 | 5.9555 | 5.9559 | 0.01 | 5.8615 | 2.14 | |
3 | 8.5898 | 8.6865 | 1.13 | 8.4999 | 1.05 | |
2,2,3-Trimethylbutane | 1 | 4.1528 | 4.1006 | 1.26 | 4.2379 | 1.94 |
2 | 5.1249 | 5.0591 | 1.28 | 5.1933 | 1.83 | |
3 | 8.1348 | 8.0010 | 1.64 | 8.2529 | 1.45 | |
2-Methylhexane | 1 | 7.1202 | 7.1621 | 0.59 | 7.0197 | 1.49 |
2 | 4.3302 | 4.4232 | 2.15 | 4.3520 | 0.08 | |
3 | 6.4961 | 6.6022 | 1.63 | 6.4584 | 0.58 | |
2,3-Dimethylpentane | 1 | 7.0737 | 7.1637 | 1.27 | 7.0045 | 1.04 |
2 | 8.3446 | 8.4279 | 1.00 | 8.2767 | 1.44 | |
3 | 7.5703 | 7.7102 | 1.85 | 7.5242 | 0.61 | |
3-Methylhexane | 1 | 5.3537 | 5.2108 | 2.67 | 5.3983 | 0.78 |
2 | 9.7008 | 9.5368 | 1.69 | 9.8088 | 1.65 | |
3 | 8.3076 | 8.1247 | 2.20 | 8.4007 | 1.12 | |
2,2,4-Trimethylpentane | 1 | 13.6205 | 13.8235 | 1.49 | 13.6397 | 0.17 |
2 | 9.7481 | 9.8102 | 0.64 | 9.7042 | 0.89 | |
3 | 11.6904 | 11.8166 | 1.08 | 11.6369 | 0.46 | |
2,4-Dimethylhexane | 1 | 7.5308 | 7.7190 | 2.50 | 7.6254 | 0.95 |
2 | 12.0867 | 12.1274 | 0.34 | 12.0074 | 1.07 | |
3 | 5.2154 | 5.3102 | 1.82 | 5.2357 | 0.39 | |
2,2,3-Trimethylpentane | 1 | 7.0814 | 6.9541 | 1.80 | 7.1235 | 1.17 |
2 | 3.9665 | 3.9703 | 0.10 | 4.0466 | 2.34 | |
3 | 3.6356 | 3.5926 | 1.18 | 3.6729 | 1.03 | |
2,3,4-Trimethylpentane | 1 | 7.9879 | 7.9515 | 0.14 | 7.9739 | 0.06 |
2 | 5.3991 | 5.4484 | 0.91 | 5.4595 | 1.00 | |
3 | 5.9442 | 5.9357 | 0.46 | 5.9409 | 0.04 | |
2,3-Dimethylhexane | 1 | 4.3620 | 4.2262 | 3.11 | 4.4585 | 2.30 |
2 | 4.3818 | 4.2664 | 2.63 | 4.4528 | 2.52 | |
3 | 5.9779 | 5.8033 | 2.92 | 6.1105 | 2.22 | |
3,4-Dimethylhexane | 1 | 6.5313 | 6.5465 | 0.28 | 6.6504 | 1.10 |
2 | 5.0972 | 5.0845 | 0.25 | 5.1479 | 1.14 | |
3 | 4.4632 | 4.4506 | 0.23 | 4.5125 | 1.95 | |
2,2,5-Trimethylhexane | 1 | 7.7787 | 7.8093 | 0.39 | 7.6336 | 1.69 |
2 | 6.1456 | 6.2382 | 1.51 | 6.1248 | 0.97 | |
3 | 7.5493 | 7.7298 | 2.39 | 7.5412 | 0.11 |
Component | Measured Value (wt%) | Mean Value (wt%) | RSD (%) | ||||
---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | |||
2,3-Dimethylbutane | 4.7289 | 4.6799 | 4.6630 | 4.6613 | 4.6298 | 4.6726 | 0.78 |
2-Methylpentane | 7.7475 | 7.6278 | 7.6606 | 7.6680 | 7.6258 | 7.6659 | 0.64 |
3-Methylpentane | 3.5913 | 3.5486 | 3.5586 | 3.5540 | 3.5390 | 3.5583 | 0.56 |
2,4-Dimethylpentane | 6.2783 | 6.2489 | 6.2517 | 6.2546 | 6.2558 | 6.2578 | 0.19 |
2,2,3-Trimethylbutane | 3.9137 | 3.8916 | 3.9033 | 3.9071 | 3.9019 | 3.9035 | 0.21 |
2-Methylhexane | 6.8789 | 6.8749 | 6.8655 | 6.8750 | 6.8775 | 6.8743 | 0.08 |
2,3-Dimethylpentane | 6.4327 | 6.4289 | 6.4326 | 6.4426 | 6.4411 | 6.4356 | 0.09 |
3-Methylhexane | 10.9570 | 10.9688 | 10.9536 | 10.9686 | 10.9730 | 10.9642 | 0.08 |
2,2,4-Trimethylpentane | 23.2735 | 23.3669 | 23.3195 | 23.3433 | 23.3566 | 23.3320 | 0.16 |
2,4-Dimethylhexane | 4.3548 | 4.3370 | 4.3977 | 4.3747 | 4.3748 | 4.3678 | 0.53 |
2,2,3-Trimethylpentane | 2.9461 | 2.9966 | 2.9515 | 2.9656 | 2.9797 | 2.9679 | 0.70 |
2,3,4-Trimethylpentane | 5.8892 | 5.9298 | 5.9284 | 5.9132 | 5.9313 | 5.9184 | 0.30 |
2,3-Dimethylhexane | 6.1666 | 6.2031 | 6.2007 | 6.1866 | 6.2028 | 6.1919 | 0.25 |
3,4-Dimethylhexane | 2.6111 | 2.6291 | 2.6386 | 2.6291 | 2.6371 | 2.6290 | 0.42 |
2,2,5-Trimethylhexane | 4.2305 | 4.2682 | 4.2747 | 4.2564 | 4.2741 | 4.2608 | 0.43 |
Component | Initial Value (g) | Spiked Value (g) | Measured Value (g) | Recovery (%) |
---|---|---|---|---|
2,3-Dimethylbutane | 0.1488 | 0.1091 | 0.2563 | 98.53 |
2-Methylpentane | 0.0926 | 0.0637 | 0.1555 | 98.74 |
3-Methylpentane | 0.0933 | 0.0946 | 0.1868 | 98.76 |
2,4-Dimethylpentane | 0.1085 | 0.1571 | 0.2688 | 102.05 |
2,2,3-Trimethylbutane | 0.1404 | 0.0613 | 0.2012 | 99.22 |
2-Methylhexane | 0.1179 | 0.1320 | 0.2498 | 99.86 |
2,3-Dimethylpentane | 0.1277 | 0.1836 | 0.3129 | 100.85 |
3-Methylhexane | 0.1163 | 0.1526 | 0.2670 | 98.76 |
2,2,4-Trimethylpentane | 0.1916 | 0.1208 | 0.3136 | 100.99 |
2,4-Dimethylhexane | 0.0746 | 0.0814 | 0.1584 | 102.85 |
2,2,3-Trimethylpentane | 0.0553 | 0.0277 | 0.0836 | 101.97 |
2,3,4-Trimethylpentane | 0.0883 | 0.0773 | 0.1647 | 98.86 |
2,3-Dimethylhexane | 0.0759 | 0.0755 | 0.1505 | 98.77 |
3,4-Dimethylhexane | 0.1003 | 0.0739 | 0.1731 | 98.53 |
2,2,5-Trimethylhexane | 0.0895 | 0.0928 | 0.1825 | 100.20 |
Serial Number | Retention Time (min) | Peak Area (%) | Similarity (%) | Alkylate Components | Molecular Weight | Molecular Formula |
---|---|---|---|---|---|---|
1 | 7.150 | 0.4114 | 95 | Isobutane | 58 | C4H10 |
2 | 8.292 | 1.4791 | 88 | 2-Methylbutane | 72 | C5H12 |
3 | 10.392 | 1.3210 | 90 | 2,3-Dimethylbutane | 86 | C6H14 |
4 | 10.470 | 1.2597 | 88 | 2,2-Dimethylbutane | 86 | C6H14 |
5 | 10.975 | 0.5609 | 95 | 3-Methylpentane | 86 | C6H14 |
6 | 12.95 | 2.1885 | 91 | 2,4-Dimethylpentane | 100 | C7H16 |
7 | 13.359 | 0.3170 | 95 | 2,2-Dimethylpentane | 100 | C7H16 |
8 | 14.998 | 0.8880 | 89 | 2-Methylhexane | 100 | C7H16 |
9 | 15.217 | 1.2700 | 93 | 2,3-Dimethylpentane | 100 | C7H16 |
10 | 15.578 | 0.6173 | 94 | 3-Methylhexane | 100 | C7H16 |
11 | 16.734 | 16.4986 | 90 | 2,2,4-Trimethylpentane | 114 | C8H18 |
12 | 19.879 | 4.4194 | 86 | 2,5-Dimethylhexane | 114 | C8H18 |
13 | 20.112 | 3.6922 | 88 | 2,4-Dimethylhexane | 114 | C8H18 |
14 | 20.255 | 2.2556 | 88 | 2,2,3-Trimethylpentane | 114 | C8H18 |
15 | 21.804 | 5.5302 | 89 | 2,3,4-Trimethylpentane | 114 | C8H18 |
16 | 22.407 | 8.5216 | 89 | 2,3,3-Trimethylpentane | 114 | C8H18 |
17 | 22.678 | 1.6362 | 90 | 2,3-Dimethylhexane | 114 | C8H18 |
18 | 23.130 | 0.6178 | 92 | 2-Methylheptane | 114 | C8H18 |
19 | 23.298 | 0.1607 | 88 | 4-Methylheptane | 114 | C8H18 |
20 | 23.610 | 0.4025 | 94 | 3,4-Dimethylhexane | 114 | C8H18 |
21 | 23.892 | 0.4454 | 90 | 3-Methylheptane | 114 | C8H18 |
22 | 25.049 | 13.3359 | 94 | 2,2,5-Trimethylhexane | 128 | C9H20 |
23 | 25.748 | 0.2054 | 96 | 2,2,4-Trimethylhexane | 128 | C9H20 |
24 | 27.218 | 0.2218 | 90 | 2,4,4-Dimethylhexane | 128 | C9H20 |
25 | 27.894 | 1.6321 | 87 | 2-Methyloctane | 128 | C9H20 |
26 | 28.433 | 0.4001 | 91 | 4,4-Dimethylheptane | 128 | C9H20 |
27 | 28.954 | 0.7304 | 93 | 2-Methyloctane | 128 | C9H20 |
28 | 29.530 | 1.3327 | 88 | 2,5-Dimethylheptane | 128 | C9H20 |
29 | 29.655 | 0.1551 | 88 | 2,2,3-Trimethylhexane | 128 | C9H20 |
30 | 30.606 | 0.0958 | 92 | 2,3,4-Trimethylhexane | 128 | C9H20 |
31 | 30.971 | 0.1409 | 92 | 1,3,5-Trimethylcyclohexane | 126 | C9H18 |
32 | 31.194 | 0.2355 | 90 | 2,3-Dimethylheptane | 128 | C9H20 |
33 | 31.423 | 0.0970 | 92 | 3,4-Dimethylheptane | 128 | C9H20 |
34 | 32.305 | 0.1495 | 95 | 2-Methyloctane | 128 | C9H20 |
35 | 32.665 | 0.3004 | 92 | 4,4-Dimethyloctane | 142 | C10H22 |
36 | 32.791 | 0.3195 | unknown | C10H22 | ||
37 | 32.952 | 2.3452 | 87 | 2,2-Dimethyloctane | 142 | C10H22 |
38 | 33.089 | 0.3087 | 96 | 2,2,4-Trimethylheptane | 142 | C10H22 |
39 | 33.461 | 2.0970 | 87 | 3,4-Dimethyloctane | 142 | C10H22 |
40 | 34.393 | 1.1930 | 88 | 2,5,5-Trimethylheptane | 142 | C10H22 |
41 | 35.018 | 0.0851 | 87 | 1,1,3,5-Tetramethylcyclohexane | 140 | C10H22 |
42 | 35.269 | 0.1540 | 87 | 2,4,6-Trimethylheptane | 142 | C10H22 |
43 | 35.550 | 0.7600 | 90 | 2,3-Dimethyloctane | 142 | C10H22 |
44 | 35.706 | 0.1259 | 91 | 2,3,5-Trimethylheptane | 142 | C10H22 |
45 | 36.064 | 0.1843 | 87 | 2,5-Dimethyloctane | 142 | C10H22 |
46 | 36.556 | 0.1462 | 86 | 2,7-Dimethyloctane | 142 | C10H22 |
47 | 36.661 | 0.2365 | 94 | 3,6-Dimethyloctane | 142 | C10H22 |
48 | 37.957 | 0.0768 | 92 | 2,3-Dimethyloctane | 142 | C10H22 |
49 | 38.536 | 1.8619 | 90 | 3,8-Dimethylnonane | 156 | C11H24 |
50 | 39.154 | 0.4097 | 92 | 2,2,6,6-Tetramethylheptane | 156 | C11H24 |
51 | 39.320 | 0.7298 | 87 | 2,2,3,5-Tetramethylheptane | 156 | C11H24 |
52 | 39.463 | 0.1995 | 89 | 2,4,6-Trimethyloctane | 156 | C11H24 |
53 | 39.592 | 0.6486 | 88 | 3,6-Dimethyldecane | 170 | C12H24 |
54 | 39.679 | 0.4938 | 86 | 3-Methylundecane | 170 | C12H24 |
55 | 40.377 | 0.4704 | 86 | 3,8-Dimethyldecane | 170 | C12H24 |
56 | 40.503 | 0.1684 | 83 | 5-Methylundecane | 170 | C12H24 |
57 | 40.763 | 0.3103 | 81 | 2,8,8-Trimethyldecane | 184 | C13H28 |
58 | 41.564 | 0.1575 | 90 | 6,6-Dimethylundecane | 184 | C13H28 |
59 | 42.015 | 1.9689 | 86 | 3,9-Dimethylundecane | 184 | C13H28 |
60 | 42.447 | 0.4732 | 87 | 3,3-Dimethylundecane | 184 | C13H28 |
61 | 42.789 | 0.9040 | 89 | 3,6-Dimethylundecane | 184 | C13H28 |
62 | 43.579 | 0.3784 | 87 | 6-Methyldodecane | 184 | C13H28 |
63 | 43.765 | 0.5435 | 88 | 2,9-Dimethylundecane | 184 | C13H28 |
64 | 44.010 | 1.0890 | 86 | 5-Methyldodecane | 184 | C13H28 |
65 | 44.283 | 0.2509 | 90 | 2,5-Dimethylundecane | 184 | C13H28 |
66 | 44.699 | 1.2211 | 87 | 4,4-Dimethylundecane | 184 | C13H28 |
67 | 44.986 | 0.2573 | 90 | 5-Methyl-5-propylnonane | 184 | C13H28 |
68 | 45.138 | 0.2227 | 94 | 3-Methyldodecane | 184 | C13H28 |
69 | 45.311 | 0.2427 | 92 | 2,2,4-Trimethyldecane | 184 | C13H28 |
70 | 45.576 | 0.4157 | 93 | 2,6-Dimethylundecane | 184 | C13H28 |
71 | 46.537 | 0.2544 | 88 | 4,6-Dimethyldodecane | 198 | C14H30 |
72 | 46.713 | 0.7725 | 87 | unknown | ||
73 | 47.060 | 0.1439 | 92 | 5-Methyltridecane | 198 | C14H30 |
74 | 47.242 | 0.2518 | 90 | 2,6,10-Trimethyldodecane | 212 | C15H32 |
75 | 48.230 | 0.4782 | 92 | 4-Methyltetradecane | 212 | C15H32 |
76 | 48.714 | 0.8915 | 90 | 2,6,11-Trimethyldodecane | 212 | C15H32 |
77 | 48.779 | 0.6753 | 90 | 3-Methyltetradecane | 212 | C15H32 |
78 | 49.045 | 0.2249 | 86 | n-pentadecane | 212 | C15H32 |
79 | 49.355 | 0.1177 | 92 | 2,2-Dimethyltetradecane | 226 | C16H34 |
80 | 49.986 | 0.1678 | 92 | n-Hexadecane | 226 | C16H34 |
81 | 50.404 | 0.2211 | 92 | 2,2,11,11-Tetramethyldodecane | 226 | C16H34 |
82 | 51.043 | 0.1408 | unknown | |||
83 | 52.963 | 0.2317 | unknown | |||
84 | 53.307 | 0.2980 | unknown | |||
85 | 53.987 | 0.0631 | unknown | |||
86 | 54.134 | 0.0924 | unknown |
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Fu, K.; Liu, B.; Chen, X.; Chen, Z.; Liang, J.; Zhang, Z.; Wang, L. Investigation of a Complex Reaction Pathway Network of Isobutane/2-Butene Alkylation by CGC–FID and CGC-MS-DS. Molecules 2022, 27, 6866. https://doi.org/10.3390/molecules27206866
Fu K, Liu B, Chen X, Chen Z, Liang J, Zhang Z, Wang L. Investigation of a Complex Reaction Pathway Network of Isobutane/2-Butene Alkylation by CGC–FID and CGC-MS-DS. Molecules. 2022; 27(20):6866. https://doi.org/10.3390/molecules27206866
Chicago/Turabian StyleFu, Kaiwei, Bei Liu, Xiaopeng Chen, Zhiyu Chen, Jiezhen Liang, Zhongyao Zhang, and Linlin Wang. 2022. "Investigation of a Complex Reaction Pathway Network of Isobutane/2-Butene Alkylation by CGC–FID and CGC-MS-DS" Molecules 27, no. 20: 6866. https://doi.org/10.3390/molecules27206866