Table 9 Performance of different hydroalkylation catalysts described in the literature
Sr.
no. Catalyst
Operating conditions
Conversion of
benzene (%) Selectivity (%)
Ref. no
Remarks
1
5 wt%Ni/ SiO
2 -Al
2 O
3
473 K, 58 bar, 0.6 h
35%
64% CHB
[136]
Batch process
2
Pt/Ni/Re-13X
443 K, pressure = 35 bar, H
2 /
HC = 1:1 LHSV(h
−1
) = 16
20%
CH 20%
CHB 75%
Others 5%
[127]
Low benzene conversion with tri-metallic/bifunctional catalyst and 50% drop
in activity in 500 min of operation
3
0.2%Pd/Hβ25
473 K, pressure = 50 bar, H
2 /
HC = 1:1
28.1%
CH 24.9% CHB 67.2%
DCHB 7.9%
[126]
Low benzene conversion under batch conditions
4
0.2%Ru/Hβ25
443 K, pressure = 10 bar
28%
CH 50%
CHB 40%
DCHB 10%
[137]
Low benzene conversion under batch conditions
5
0.3%Ru/0.3%
Sn/MCM-22
393 K, Pressure = 8 bar, H
2 /
HC = 1:1, WHSV(h
−1
) = 1
43.9%
CH 12.8% CHB 71.4%
DCHB15.2%
Others 0.6%
[119]
Bimetallic-functional catalyst comprising proprietary zeolite
6
0.3%Pd/MCM-22
423 K, pressure = 10 bar,
WHSV(h
−1
) = 2, H
2 /HC = 1:1
48.6%
CH 10.5% CHB 70.3%
DCHB 17.5%
Others 1.7%
[144]
Catalyst comprising patented zeolite
7
1.63%Ni/0.79%F/
7.3%W/Al
2 O
3 -SiO
2
423 K, pressure = 55 bar,
0.09 L of H
2 /cc of benzene
26.1%
CH 15.4% CHB 62.6%
DCHB 18.3%
Others 3.6%
[132]
Multi metal/functional catalyst with batch process
8
0.3%Pd/MCM-49
423 K, pressure = 10 bar,
WHSV(h
−1
) = 0.52,
H
2 /HC = 0.64
33.6%
CH 4.2%
CHB 75.8%
DCHB 15.5%
Others 4.5%
[144]
Catalyst comprising patented zeolite
9
0.3%Pd/HBeta
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
64.1%
CH 69.2% CHB 24.3%
Others 6.5%
[138]
Batch process with powder catalyst
10 0.2%Pd/HY
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
83.7%
CH 71.8%
CHB 21.4%
Others 6.7%
[138]
Batch process with powder catalyst
11 0.2%Rh/HBeta
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
86.3%
CH 59.6%
CHB 18.3%
Others 21.9%
[138]
Batch process with powder catalyst
12 0.2%Pd@HBeta
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
85.6%
CH 49.8% CHB 44%
Others 6.2%
[138]
Batch process with powder catalyst employing zeolite prepared by complex
procedure of coating silica-alumina framework outside the conventional Pd/HBeta
Sr.
no. Catalyst
Operating conditions
Conversion of
benzene (%) Selectivity (%)
Ref. no
Remarks
1
5 wt%Ni/ SiO
2 -Al
2 O
3
473 K, 58 bar, 0.6 h
35%
64% CHB
[136]
Batch process
2
Pt/Ni/Re-13X
443 K, pressure = 35 bar, H
2 /
HC = 1:1 LHSV(h
−1
) = 16
20%
CH 20%
CHB 75%
Others 5%
[127]
Low benzene conversion with tri-metallic/bifunctional catalyst and 50% drop
in activity in 500 min of operation
3
0.2%Pd/Hβ25
473 K, pressure = 50 bar, H
2 /
HC = 1:1
28.1%
CH 24.9% CHB 67.2%
DCHB 7.9%
[126]
Low benzene conversion under batch conditions
4
0.2%Ru/Hβ25
443 K, pressure = 10 bar
28%
CH 50%
CHB 40%
DCHB 10%
[137]
Low benzene conversion under batch conditions
5
0.3%Ru/0.3%
Sn/MCM-22
393 K, Pressure = 8 bar, H
2 /
HC = 1:1, WHSV(h
−1
) = 1
43.9%
CH 12.8% CHB 71.4%
DCHB15.2%
Others 0.6%
[119]
Bimetallic-functional catalyst comprising proprietary zeolite
6
0.3%Pd/MCM-22
423 K, pressure = 10 bar,
WHSV(h
−1
) = 2, H
2 /HC = 1:1
48.6%
CH 10.5% CHB 70.3%
DCHB 17.5%
Others 1.7%
[144]
Catalyst comprising patented zeolite
7
1.63%Ni/0.79%F/
7.3%W/Al
2 O
3 -SiO
2
423 K, pressure = 55 bar,
0.09 L of H
2 /cc of benzene
26.1%
CH 15.4% CHB 62.6%
DCHB 18.3%
Others 3.6%
[132]
Multi metal/functional catalyst with batch process
8
0.3%Pd/MCM-49
423 K, pressure = 10 bar,
WHSV(h
−1
) = 0.52,
H
2 /HC = 0.64
33.6%
CH 4.2%
CHB 75.8%
DCHB 15.5%
Others 4.5%
[144]
Catalyst comprising patented zeolite
9
0.3%Pd/HBeta
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
64.1%
CH 69.2% CHB 24.3%
Others 6.5%
[138]
Batch process with powder catalyst
10 0.2%Pd/HY
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
83.7%
CH 71.8%
CHB 21.4%
Others 6.7%
[138]
Batch process with powder catalyst
11 0.2%Rh/HBeta
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
86.3%
CH 59.6%
CHB 18.3%
Others 21.9%
[138]
Batch process with powder catalyst
12 0.2%Pd@HBeta
1 g cat, 3.6 mg of benzene,
40 bar, T = 473 K t = 180 min
85.6%
CH 49.8% CHB 44%
Others 6.2%
[138]
Batch process with powder catalyst employing zeolite prepared by complex
procedure of coating silica-alumina framework outside the conventional Pd/HBeta