Study on the performance of alkali acid modified ZSM-5 catalysts for thiophene alkylation reaction
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摘要: 以SiO2/Al2O3物质的量比为50的HZSM-5分子筛为原粉，经过一定浓度的NaOH溶液处理后再使用柠檬酸溶液进行酸洗以制备微孔-介孔多级孔HZSM-5催化剂，并研究其在模拟油中的噻吩烷基化反应性能。结果表明，使用柠檬酸溶液进行酸洗可以清除碱处理后孔道内残余的杂质。当柠檬酸溶液浓度为0.5 mol/L时，此时得到的HZ（AC-0.5）催化剂具有适宜的孔径和酸性，因而噻吩烷基化转化率最高，达到95.6%。在HZ（AC-0.5）催化剂上以苯并噻吩作为噻吩衍生物模型化合物，异戊二烯作为烯烃模型化合物，苯作为芳烃模型化合物，分别考察噻吩烷基化反应性能，并分析不同组分的模拟油对噻吩烷基化反应转化率和选择性的影响。结果表明，噻吩烷基化的最佳反应温度是120 ℃，在该温度下苯并噻吩烷基化的转化率高于噻吩烷基化的转化率，当异戊二烯作为烯烃模型化合物后噻吩的转化率会升高，当苯作为芳烃模型化合物后噻吩的转化率会降低。Abstract: HZSM-5 zeolites with SiO2/Al2O3 molar ratio of 50 as the raw material were treated by a certain concentration of NaOH and then impregnated with citric acid solution to prepare microporous and mesoporous hierarchical HZSM-5 catalyst. The catalytic performance of the prepared catalysts for thiophene alkylation reaction was investigated using simulated oil. The results show that the residual impurities in the pores after alkali treatment can be eliminated by acid washing with citric acid solution. When the concentration of the citric acid solution is 0.5 mol/L, the HZ(AC-0.5) catalyst has the appropriate pore size and acidity, so the conversion of thiophene alkylation is the highest, which is up to 95.6%. The performance of thiophene alkylation reaction was also investigated by respectively using dibenzothiophene thiophene derivatives as model compounds, olefin isoprene as model compounds, aromatic benzene as model compound on the HZ (AC-0.5) catalyst. And then we analyzed the influence of different components in the simulated oil on the conversion and selectivity of thiophene alkylation reaction. It has been demonstrated that the optimum reaction temperature of thiophene alkylation reaction is 120℃. At the optimum temperature, the conversion of benothiophene alkylation is higher than that of thiophene alkylation. The conversion of thiophene will be increased when the olefin isoprene is used as model compound. The conversion of thiophene will be decreased when benzene is used as aromatic model compound.
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Key words:
- alkali treatment /
- acid washing /
- ZSM-5 /
- desulfurization /
- thiophene alkylation
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图 1 酸洗后HZSM-5催化剂的XRD谱图
Figure 1 XRD patterns of the HZSM-5 catalysts after impregnation
a: HZ; b: HZ(A); c: HZ(AC-0.1); d: HZ(AC-0.5); e: HZ(AC-1.0)
图 2 HZSM-5催化剂的N2吸附-脱附等温线
Figure 2 N2 adsorption desorption isotherms of the HZSM-5 catalysts
a: HZ; b: HZ(A); c: HZ(AC-0.1); d: HZ(AC-0.5); e: HZ(AC-1.0)
图 3 HZSM-5催化剂的SEM照片
Figure 3 SEM images of the HZSM-5 catalysts
(a): HZ; (b): HZ(A); (c): HZ(AC-0.1); (d): HZ(AC-0.5); (e): HZ(AC-1.0)
图 5 HZ(AC-0.5)催化剂上反应前后模拟油的色谱谱图
Figure 5 GC spectra of the simulated oil before reaction over HZ(AC-0.5)
(a): 1.0-3.0 min; (b): 2-16 min
1, 5: 1-henxe; 2: hexane; 3: thiophene; 4: xylene; 6: HT; 7: HX; 8: DHT; 9: 1-henxe polymerization
图 6 不同含量的二甲苯下反应物的转化率
Figure 6 Conversions of reactants at different xylene concentrations
a: thiophene; b: 1-hexene; c: xylene
表 1 HZSM-5催化剂的相对结晶度和n(SiO2)/n(Al2O3)
Table 1 Relative crystallinity and n(SiO2)/n(Al2O3) of the HZSM-5 catalysts
Sample HZ HZ(A) HZ(AC-0.1) HZ(AC-0.5) HZ(AC-1.0) Relative crystallinity/% 100 78.1 71.6 65.4 59.2 SiO2/Al2O3(molar ratio) 50 33 35 36 39 
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表 2 HZSM-5催化剂的结构性质变化
Table 2 Pore structural parameters of the HZSM catalysts
Sample ABET/
(m2·g-1)Aext/
(m2·g-1)vmicro/
(mL·g-1)vmeso/
(mL·g-1)daver/
nmHZ 317.9 78.70 11.9 5.4 2.1 HZ(A) 400.6 150.6 9.0 36.4 5.6 HZ(AC-0.1) 412.5 164.7 10.3 37.7 5.7 HZ(AC-0.5) 423.3 173.1 11.1 40.3 5.7 HZ(AC-1.0) 425.4 184.3 10.8 42.8 6.1
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表 3 HZSM-5催化剂的噻吩烷基化反应物的转化率
Table 3 Conversion of the thiophene alkylation reaction on the HZAM-5 catalysts
Sample Conversation x/% HZ HZ(A) HZ(AC-0.1) HZ(AC-0.5) HZ(AC-1.0) Thiophene 47.2 82.4 89.3 95.6 70.1 1-hexene 6.3 9.6 15.7 18.1 16.3 Xylene 8.9 11.4 18.3 20.5 15.4 reaction conditions: t=120 ℃, p=1.0 MPa, GHSV=1.0 h-1, t=6 h
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表 4 反应温度对原料油各组分的转化率
Table 4 Effect of reaction temperature on convertion of components in the raw oil
Temperature
t/℃Conversion x/% HTS distribution w/% ITS distribution w/% thiophene 1-hexene xylene HT DHT DIT TIT 60 64.8 6.7 13.2 43.2 52.4 93.2 6.8 90 78.2 13.6 15.4 35.4 57.3 89.1 10.9 120 89.6 18.2 20.5 30.3 60.9 87.7 12.3 150 85.4 20.5 28.9 22.6 68.2 75.8 24.2 HTS: thiophene alkyl products; HT: monosubstitutedproducts; DHT; disubstitutedproducts; THT; trisubstitution product;
ITS: olefinicpolymerization; DIT: two polymerization product; TIT: three polymerization product; FIT: four polymerization product; reaction conditions: p=1.0 MPa, GHSV=1.0 h-1, t=6 h
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表 5 噻吩烷基化反应物转化率及产物分布
Table 5 Conversion and product distribution of the thiophene alkylation reaction on the catalyst
Model oil Conversion x/% HTS distribution w/% HXS distribution w/% thiophene and its derivatives 1-hexene xylene HT DHT THT HX DHX 1# 95.6 18.1 20.5 30.3 60.9 8.8 89.2 10.8 2# 98.6 14.6 16.9 59.8 37.2 3.0 74.6 25.4 3# 90.3 11.5 12.9 47.4 49.5 3.1 64.8 35.2 4# 86.5 9.6 7.5 42.1 56.1 1.6 50.3 49.7 HTS: thiophene alkyl products; HT: mo nosubstituted products; DHT; disubstituted products; THT; trisubstitution product;
HXS: aromatic alkyl products; HX: single substitution products; DHX: two substitution products; FHT: four substitution products; reaction conditions: t=120 ℃, p=1.0 MPa, GHSV=1.0 h-1, t=6 h
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表 6 噻吩烷基化反应物转化率及产物分布
Table 6 Conversion and product distribution of the thiophene alkylation reaction on the catalysts
Modeloil Conversion x/% HTS distribution w/% ITS distribution w/% thiophene olefin xylene HT DHT THT FHT DIT TIT FIT 1# 95.6 18.1 20.5 30.3 60.9 8.8 0 87.7 12.3 0 5# 96.6 25.4 26.1 47.5 27.2 20.5 4.8 74.3 23.8 1.9 6# 97.2 28.9 28.9 50.6 21.7 22.3 5.4 70.1 27.5 2.4 7# 98.3 33.4 32.4 57.4 16.3 29.4 6.9 64.9 30.8 4.3 reaction conditions: t=120℃, p=1.0 MPa, GHSV=1.0 h-1, t=6 h
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表 7 噻吩烷基化反应物转化率及产物分布
Table 7 Conversion and product distribution of the thiophene alkylation reaction on the
Model oil Conversion x/% HTS distribution w/% HXS distribution w/% thiophene 1-hexene aromatics HT DHT THT HX DHX 1# 95.6 18.1 20.5 30.3 60.9 8.8 89.2 10.8 8# 90.3 27.4 25.7 21.7 75.7 2.6 50.3 49.7 reaction condition: t=120 ℃, p=1.0 MPa, GHSV=1.0 h-1, t=6 h
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