CN1676215A - 单环芳烃部分加氢生产环烯烃的催化剂、其制备方法及应用 - Google Patents
单环芳烃部分加氢生产环烯烃的催化剂、其制备方法及应用 Download PDFInfo
- Publication number
- CN1676215A CN1676215A CN 200510017311 CN200510017311A CN1676215A CN 1676215 A CN1676215 A CN 1676215A CN 200510017311 CN200510017311 CN 200510017311 CN 200510017311 A CN200510017311 A CN 200510017311A CN 1676215 A CN1676215 A CN 1676215A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- zinc
- weight
- ruthenium
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 102
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- -1 monocyclic aromatic hydrocarbon Chemical class 0.000 title claims abstract description 13
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 20
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 16
- 239000002184 metal Substances 0.000 claims abstract description 16
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 12
- 150000003058 platinum compounds Chemical class 0.000 claims abstract description 9
- 150000003304 ruthenium compounds Chemical class 0.000 claims abstract description 9
- KFZAUHNPPZCSCR-UHFFFAOYSA-N iron zinc Chemical compound [Fe].[Zn] KFZAUHNPPZCSCR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000009467 reduction Effects 0.000 claims abstract description 8
- 238000000975 co-precipitation Methods 0.000 claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052725 zinc Inorganic materials 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229940045985 antineoplastic platinum compound Drugs 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 229910002651 NO3 Inorganic materials 0.000 claims description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 6
- 229960001763 zinc sulfate Drugs 0.000 claims description 6
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 150000003752 zinc compounds Chemical class 0.000 claims description 5
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000003426 co-catalyst Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 17
- 150000001925 cycloalkenes Chemical class 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000011259 mixed solution Substances 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 21
- 238000011156 evaluation Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 230000008859 change Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- SGDMQXAOPGGMAH-UHFFFAOYSA-N phenol;thiophene Chemical compound C=1C=CSC=1.OC1=CC=CC=C1 SGDMQXAOPGGMAH-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- UGYRYNXDEOFIQB-UHFFFAOYSA-N benzene thiophene Chemical compound S1C=CC=C1.C1=CC=CC=C1.C1=CC=CC=C1 UGYRYNXDEOFIQB-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000010148 water-pollination Effects 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
反应时间(分钟) | 苯的转化率(%) | 环己烯的选择率(%) | 环己烯的收率(%) | γ40 | SEL40 | |
实例1 | 5 | 11.45 | 86.46 | 9.9 | 132.5 | 83.4 |
15 | 33.74 | 84.22 | 28.4 | |||
30 | 56.80 | 80.39 | 45.7 | |||
实例2 | 5 | 24.94 | 81.20 | 20.2 | 186.2 | 78.5 |
15 | 68.41 | 72.78 | 49.8 | |||
30 | 92.46 | 61.78 | 57.1 | |||
实例3 | 5 | 20.42 | 82.24 | 16.8 | 162.2 | 77.3 |
15 | 61.06 | 71.53 | 43.7 | |||
30 | 85.48 | 61.62 | 52.7 | |||
实例4 | 5 | 7.97 | 89.23 | 7.1 | 108.5 | 85.7 |
15 | 26.98 | 86.77 | 23.4 | |||
30 | 52.28 | 83.41 | 43.6 |
改变条件 | γ40 | SEL40 | |
对比实例1 | 催化剂0.5克 | 101.5 | 81.5 |
催化剂4.0克 | 190.6 | 80.1 | |
对比实例2 | ZrO2 0.5克 | 145.6 | 77.8 |
ZrO2 20克 | 130.4 | 83.2 | |
对比实例3 | ZnSO4·7H2O 1克 | 156.2 | 70.6 |
ZnSO4·7H2O 60克 | 120.1 | 84.1 | |
对比实例4 | 反应温度120℃ | 70.5 | 80.4 |
噻酚浓度mg/L | 进口催化剂 | 本发明催化剂 | ||
γ40 | SEL40 | γ40 | SEL40 | |
0.00 | 103.3 | 80.6 | 132.5 | 83.4 |
2.48 | 104.5 | 79.5 | 134.3 | 83.1 |
4.29 | 103.4 | 78.0 | 135.1 | 82.2 |
6.24 | 102.3 | 76.2 | 133.8 | 81.9 |
8.55 | 103.6 | 76.0 | 132.9 | 80.9 |
12.91 | 105.4 | 73.5 | 134.7 | 79.8 |
17.31 | 102.9 | 71.3 | 131.4 | 78.4 |
26.76 | 79.4 | 65.8 | 126.9 | 77.0 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200510017311XA CN1315571C (zh) | 2005-01-11 | 2005-01-11 | 单环芳烃部分加氢生产环烯烃的催化剂、其制备方法及应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200510017311XA CN1315571C (zh) | 2005-01-11 | 2005-01-11 | 单环芳烃部分加氢生产环烯烃的催化剂、其制备方法及应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1676215A true CN1676215A (zh) | 2005-10-05 |
CN1315571C CN1315571C (zh) | 2007-05-16 |
Family
ID=35049052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB200510017311XA Active CN1315571C (zh) | 2005-01-11 | 2005-01-11 | 单环芳烃部分加氢生产环烯烃的催化剂、其制备方法及应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1315571C (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102319562A (zh) * | 2011-09-13 | 2012-01-18 | 北京旭阳化工技术研究院有限公司 | 苯选择加氢制环己烯的催化剂的制备方法及通过该方法制备的催化剂 |
CN113042043A (zh) * | 2021-03-24 | 2021-06-29 | 内蒙古瑞翔拓创新材料有限公司 | 钌基加氢催化剂、钌基加氢催化剂水溶液及制备方法和应用 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4374536A (en) * | 1980-09-05 | 1983-02-22 | Becker Sharon L | Energy saving window screen guide device |
JPH08188542A (ja) * | 1995-01-06 | 1996-07-23 | Mitsubishi Chem Corp | シクロオレフィンの製造方法 |
-
2005
- 2005-01-11 CN CNB200510017311XA patent/CN1315571C/zh active Active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102319562A (zh) * | 2011-09-13 | 2012-01-18 | 北京旭阳化工技术研究院有限公司 | 苯选择加氢制环己烯的催化剂的制备方法及通过该方法制备的催化剂 |
CN104923222A (zh) * | 2011-09-13 | 2015-09-23 | 北京旭阳化工技术研究院有限公司 | 苯选择加氢制环己烯的催化剂的制备方法及通过该方法制备的催化剂 |
CN113042043A (zh) * | 2021-03-24 | 2021-06-29 | 内蒙古瑞翔拓创新材料有限公司 | 钌基加氢催化剂、钌基加氢催化剂水溶液及制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN1315571C (zh) | 2007-05-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1130265C (zh) | 有机化合物转化反应中可使用的载体上的催化剂 | |
CN1046215C (zh) | 一种含有第ⅲa族和第ⅷ族金属的选择加氢催化剂及用途 | |
CN108499564B (zh) | 一种乙醇酸甲酯的合成过程中的催化剂及其制备方法、应用 | |
CN103752305B (zh) | 一种催化剂、其制备方法以及使用该催化剂生产丙烯酸甲酯并联产甲基丙烯酸甲酯的方法 | |
CN105777535B (zh) | 用于制备葡糖二酸的方法 | |
CN106563449B (zh) | 草酸酯加氢合成乙二醇催化剂及其制备方法和开工方法 | |
CN102029160B (zh) | 一种用于制备间苯二甲胺的催化剂及其制备方法 | |
CN1772379A (zh) | 甲基异丁基醇气相催化脱氢铜系催化剂、制备方法及应用方法 | |
CN104190417A (zh) | 一种苯部分加氢制环己烯的钌基双金属催化剂的制备方法 | |
CN112191268A (zh) | 一种Ni-IL/介孔三氧化二铝催化剂及其制备与应用 | |
CN102744085B (zh) | 一种含纳米Ru催化剂和碱式硫酸锌盐的催化体系及其催化苯选择加氢制环己烯方法 | |
CN1156425C (zh) | 环己醇脱氢制环己酮的方法 | |
CN1074631A (zh) | 负载型丁烯氧化脱氢制丁二烯催化剂 | |
CN114716347A (zh) | 一种制备己二腈的方法 | |
CN1315571C (zh) | 单环芳烃部分加氢生产环烯烃的催化剂、其制备方法及应用 | |
CN1420861A (zh) | 将腈官能团氢化为胺官能团的方法 | |
CN113042043A (zh) | 钌基加氢催化剂、钌基加氢催化剂水溶液及制备方法和应用 | |
CN101455962A (zh) | 由环己酮二聚物脱氢制备邻苯基苯酚的催化剂及其制备方法 | |
CN110508290B (zh) | 高分散钯/氢氧化钴催化剂及其制备方法和应用 | |
CN1261212C (zh) | 一种低碳烷烃异构化催化剂及制备方法 | |
CN1234666C (zh) | Ru-B负载型催化剂的制备方法 | |
CN110882696B (zh) | 一种芳烃加氢生产环烷烃的催化剂及其制备方法 | |
CN115197094A (zh) | 一种1-氨基-2-氰基环戊烯的制备方法 | |
CN106423202A (zh) | 一种醋酸加氢制备乙醇的铑钌复合催化剂的制备方法 | |
CN113244918A (zh) | 钌基载体型加氢催化剂及其制备方法和应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: HENAN SHENMA NYLON CHEMICAL Co.,Ltd. Assignor: CHINA SHENMA GROUP Co.,Ltd. Contract fulfillment period: 2009.3.30 to 2015.1.10 Contract record no.: 2009410000022 Denomination of invention: Catalyst for producing cycloolefine by partial hydrogenation of mononuclear aromatics, and its preparing method and use Granted publication date: 20070516 License type: Exclusive license Record date: 20090403 |
|
LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2009.3.30 TO 2015.1.10; CHANGE OF CONTRACT Name of requester: HENAN SHENMA NYLON CHEMICAL CO.,LTD. Effective date: 20090403 |
|
TR01 | Transfer of patent right |
Effective date of registration: 20211222 Address after: 467000 6th floor, building 23, No. 666, high tech torch Park, east section of Shenma Avenue, Pingdingshan City, Henan Province Patentee after: HENAN SHENMA CATALYTIC TECHNOLOGY Co.,Ltd. Address before: 467000 miner Middle Road No. 21, Henan Province, Pingdingshan Patentee before: CHINA PINGMEI SHENMA ENERGY CHEMICAL GROUP Co.,Ltd. Effective date of registration: 20211222 Address after: 467000 miner Middle Road No. 21, Henan Province, Pingdingshan Patentee after: CHINA PINGMEI SHENMA ENERGY CHEMICAL GROUP Co.,Ltd. Address before: 467000 Construction No. 63 Middle Road, Henan, Pingdingshan Patentee before: CHINA SHENMA GROUP Co.,Ltd. |
|
TR01 | Transfer of patent right |