CN102921414B - 一种苯环烷基酯加氢催化剂及其制备方法 - Google Patents
一种苯环烷基酯加氢催化剂及其制备方法 Download PDFInfo
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- CN102921414B CN102921414B CN201210414775.4A CN201210414775A CN102921414B CN 102921414 B CN102921414 B CN 102921414B CN 201210414775 A CN201210414775 A CN 201210414775A CN 102921414 B CN102921414 B CN 102921414B
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- 239000003054 catalyst Substances 0.000 title claims abstract description 63
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 30
- -1 rare earth metal salt Chemical class 0.000 claims abstract description 29
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 16
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 15
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000005507 spraying Methods 0.000 claims abstract description 5
- 238000011068 loading method Methods 0.000 claims abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical group [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000011833 salt mixture Substances 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000001035 drying Methods 0.000 abstract description 4
- 238000002791 soaking Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- 229910003445 palladium oxide Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NGDQQLAVJWUYSF-UHFFFAOYSA-N 4-methyl-2-phenyl-1,3-thiazole-5-sulfonyl chloride Chemical compound S1C(S(Cl)(=O)=O)=C(C)N=C1C1=CC=CC=C1 NGDQQLAVJWUYSF-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- LFPNMDQJMKJUSM-UHFFFAOYSA-N dimethyl thiane-4,4-dicarboxylate Chemical compound COC(=O)C1(C(=O)OC)CCSCC1 LFPNMDQJMKJUSM-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910001680 bayerite Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- AIACXWOETVLBIA-UHFFFAOYSA-N dimethyl cyclohexane-1,2-dicarboxylate Chemical compound COC(=O)C1CCCCC1C(=O)OC AIACXWOETVLBIA-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000002803 maceration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
催化剂 | 转化率 | 收率 |
A | 99.6 | 98.1 |
B | 97.1 | 96.5 |
C | 99.8 | 98.3 |
D | 99.6 | 97.8 |
E | 99.4 | 97.9 |
F | 95.3 | 94.6 |
G | 99.6 | 97.9 |
H | 99.1 | 98.0 |
I | 97.5 | 96.5 |
原料 | 温度℃ | 压力MPa | 转化率 | 收率 |
DOP | 145 | 3.0 | 99.7 | 98.9 |
DOP | 135 | 4.0 | 99.6 | 99.3 |
DBP | 140 | 3.0 | 99.8 | 99.0 |
DBP | 130 | 5.0 | 99.9 | 99.5 |
Claims (4)
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CN201210414775.4A CN102921414B (zh) | 2012-10-17 | 2012-10-17 | 一种苯环烷基酯加氢催化剂及其制备方法 |
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CN102921414A CN102921414A (zh) | 2013-02-13 |
CN102921414B true CN102921414B (zh) | 2015-01-21 |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107774334B (zh) * | 2016-08-29 | 2020-06-09 | 中国石油化工股份有限公司 | 合成脂肪酸甲酯乙氧基化物的催化剂 |
CN112174777A (zh) * | 2020-11-06 | 2021-01-05 | 本源精化环保科技有限公司 | 一种2,2’-二(4-羟基环己基)丙烷的制备方法 |
CN114315789A (zh) * | 2020-12-15 | 2022-04-12 | 江苏景宏新材料科技有限公司 | 一种l-丙交酯的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3852215A (en) * | 1971-12-13 | 1974-12-03 | Products Pour Catalyse Soc Fr | Catalyst for hydrocarbon conversion |
CN1457923A (zh) * | 2002-12-25 | 2003-11-26 | 南化集团研究院 | 一种苯加氢制环己烷用铂系催化剂及其制备方法 |
CN1138595C (zh) * | 1999-03-02 | 2004-02-18 | 伊斯曼化学公司 | 催化剂载体、负载催化剂和1,2-环氧丁烷的制备方法 |
CN1850330A (zh) * | 2006-05-23 | 2006-10-25 | 上海师范大学 | 一种负载型非晶态合金氢化催化剂及其制备方法 |
CN102408297A (zh) * | 2010-09-21 | 2012-04-11 | 中国石油化工股份有限公司 | 苯加氢制备环己烷的方法 |
-
2012
- 2012-10-17 CN CN201210414775.4A patent/CN102921414B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3852215A (en) * | 1971-12-13 | 1974-12-03 | Products Pour Catalyse Soc Fr | Catalyst for hydrocarbon conversion |
CN1138595C (zh) * | 1999-03-02 | 2004-02-18 | 伊斯曼化学公司 | 催化剂载体、负载催化剂和1,2-环氧丁烷的制备方法 |
CN1457923A (zh) * | 2002-12-25 | 2003-11-26 | 南化集团研究院 | 一种苯加氢制环己烷用铂系催化剂及其制备方法 |
CN1850330A (zh) * | 2006-05-23 | 2006-10-25 | 上海师范大学 | 一种负载型非晶态合金氢化催化剂及其制备方法 |
CN102408297A (zh) * | 2010-09-21 | 2012-04-11 | 中国石油化工股份有限公司 | 苯加氢制备环己烷的方法 |
Non-Patent Citations (1)
Title |
---|
巴豆醛气相选择性加氢催化剂;陈萍 等;《化学进展》;20120131;第24卷(第1期);第17-30页 * |
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