CN102744084B - 一种苯选择加氢制环己烯的催化体系及其催化苯选择加氢制环己烯的方法 - Google Patents
一种苯选择加氢制环己烯的催化体系及其催化苯选择加氢制环己烯的方法 Download PDFInfo
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- CN102744084B CN102744084B CN201210255301XA CN201210255301A CN102744084B CN 102744084 B CN102744084 B CN 102744084B CN 201210255301X A CN201210255301X A CN 201210255301XA CN 201210255301 A CN201210255301 A CN 201210255301A CN 102744084 B CN102744084 B CN 102744084B
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 150
- 239000003054 catalyst Substances 0.000 title claims abstract description 131
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003751 zinc Chemical class 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 6
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 4
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 4
- 150000003624 transition metals Chemical class 0.000 claims abstract description 4
- 239000011592 zinc chloride Substances 0.000 claims abstract description 3
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims abstract description 3
- 229960001763 zinc sulfate Drugs 0.000 claims abstract description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims abstract description 3
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- 239000002184 metal Substances 0.000 claims description 24
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 238000003556 assay Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000010606 normalization Methods 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 238000005070 sampling Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 5
- 238000000975 co-precipitation Methods 0.000 abstract description 2
- 229910019891 RuCl3 Inorganic materials 0.000 abstract 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
- 229940043237 diethanolamine Drugs 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- -1 Li 2Among O Inorganic materials 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 230000010148 water-pollination Effects 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
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- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
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- 238000006703 hydration reaction Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
碱性物质M及用量 | ZnSO4浓度/mol/L | 时间/min | 苯转化率/% | 环己烯选择性/% | 环己烯收率/% | |
实施例1 | 无 | 0.6 | 5 | 46.4 | 74.5 | 34.6 |
实施例2 | 0.32g NaOH | 0.6 | 15 | 43.3 | 81.0 | 35.0 |
实施例3 | 5.70g NaOH | 0.6 | 25 | 29.4 | 87.3 | 25.7 |
实施例4 | 0.31g Fe2O3 | 0.6 | 20 | 55.8 | 80.3 | 44.8 |
实施例5 | 0.59g MnO2 | 0.6 | 25 | 51.6 | 79.9 | 41.3 |
实施例6 | 10.00g MnO2 | 0.6 | 25 | 34.3 | 85.2 | 29.2 |
实施例7 | 0.32g ZnO | 0.6 | 25 | 51.3 | 85.6 | 43.9 |
实施例8 | 5.77g ZnO | 0.6 | 25 | 52.2 | 85.2 | 44.5 |
实施例9 | 10.00g ZnO | 0.6 | 25 | 52.4 | 82.2 | 43.1 |
实施例10 | 0.32g ZnO | 0.3 | 25 | 19.1 | 89.5 | 17.1 |
实施例11 | 0.32g ZnO | 0.7 | 25 | 78.8 | 69.2 | 54.6 |
实施例12 | 0.46g La2O3 | 0.6 | 15 | 58.5 | 77.3 | 45.2 |
实施例13 | 0.87g La2O3 | 0.6 | 25 | 62.5 | 80.7 | 50.4 |
实施例14 | 0.51g Ce(OH)3 | 0.6 | 10 | 44.1 | 80.0 | 35.3 |
实施例15 | 0.6g 乙二胺 | 0.6 | 20 | 52.9 | 79.3 | 41.9 |
实施例16 | 0.4g 乙醇胺 | 0.6 | 10 | 49.2 | 78.5 | 38.6 |
实施例17 | 0.8g 二乙醇胺 | 0.6 | 25 | 57.7 | 80.5 | 46.4 |
实施例18 | 1.00g 二乙醇胺 | 0.6 | 25 | 29.1 | 88.5 | 25.8 |
实施例19 | 1.0g 三乙醇胺 | 0.6 | 20 | 60.8 | 78.0 | 47.4 |
实施例20 | 0.42g Na2CO3 | 0.6 | 25 | 65.0 | 77.6 | 50.4 |
实施例21 | 3.06g Na2SiO3 | 0.6 | 25 | 58.2 | 76.2 | 44.3 |
实施例22 | 4.43g Na2SiO3 | 0.6 | 25 | 69.4 | 76.6 | 53.1 |
实施例23 | 12.34g Na2SiO3 | 0.6 | 25 | 99.6 | 18.4 | 18.3 |
Claims (7)
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CN201210255301XA CN102744084B (zh) | 2012-07-23 | 2012-07-23 | 一种苯选择加氢制环己烯的催化体系及其催化苯选择加氢制环己烯的方法 |
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CN103785386B (zh) * | 2012-10-31 | 2016-04-06 | 湖南长岭石化科技开发有限公司 | 苯选择性加氢制备环己烯的催化剂及其制备方法和应用和苯选择性加氢制备环己烯的方法 |
CN103785387B (zh) * | 2012-10-31 | 2016-09-07 | 湖南长岭石化科技开发有限公司 | 苯选择性加氢制备环己烯的催化剂及其制备方法和应用和苯选择性加氢制备环己烯的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1489574A (zh) * | 2001-01-31 | 2004-04-14 | ������������ʽ���� | 生产环己酮肟的方法 |
CN1795983A (zh) * | 2004-12-23 | 2006-07-05 | 中国科学院大连化学物理研究所 | 用于苯选择加氢反应的催化剂及制备方法和应用 |
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 |
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CN1489574A (zh) * | 2001-01-31 | 2004-04-14 | ������������ʽ���� | 生产环己酮肟的方法 |
CN1795983A (zh) * | 2004-12-23 | 2006-07-05 | 中国科学院大连化学物理研究所 | 用于苯选择加氢反应的催化剂及制备方法和应用 |
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 |
Non-Patent Citations (2)
Title |
---|
单层分散型Ru-Zn催化剂及其催化苯选择加氢制环己烯的性能;孙海杰等;《催化学报》;20111231;第32卷(第2期);224-230页 * |
孙海杰等.单层分散型Ru-Zn催化剂及其催化苯选择加氢制环己烯的性能.《催化学报》.2011,第32卷(第2期), |
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