CN104190391B - 一种催化剂及其在制备百里香酚方法中的用途 - Google Patents
一种催化剂及其在制备百里香酚方法中的用途 Download PDFInfo
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- CN104190391B CN104190391B CN201410312426.0A CN201410312426A CN104190391B CN 104190391 B CN104190391 B CN 104190391B CN 201410312426 A CN201410312426 A CN 201410312426A CN 104190391 B CN104190391 B CN 104190391B
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- catalyst
- metacresol
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- thymol
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- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 title claims abstract description 116
- 239000003054 catalyst Substances 0.000 title claims abstract description 72
- 239000005844 Thymol Substances 0.000 title claims abstract description 58
- 229960000790 thymol Drugs 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 26
- 229940100630 metacresol Drugs 0.000 claims abstract description 55
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052593 corundum Inorganic materials 0.000 claims abstract description 33
- 229910001845 yogo sapphire Inorganic materials 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 9
- 238000000465 moulding Methods 0.000 claims abstract description 8
- 239000002002 slurry Substances 0.000 claims abstract description 8
- 239000008187 granular material Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 229910003158 γ-Al2O3 Inorganic materials 0.000 claims description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 5
- -1 propylene, propylene Chemical group 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 238000007781 pre-processing Methods 0.000 claims description 2
- 238000004886 process control Methods 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 22
- 238000003786 synthesis reaction Methods 0.000 abstract description 22
- 230000029936 alkylation Effects 0.000 abstract description 19
- 238000005804 alkylation reaction Methods 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000011148 porous material Substances 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 101100494773 Caenorhabditis elegans ctl-2 gene Proteins 0.000 description 6
- 101100112369 Fasciola hepatica Cat-1 gene Proteins 0.000 description 6
- 101100005271 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-1 gene Proteins 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000008859 change Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 101150116295 CAT2 gene Proteins 0.000 description 1
- 101100392078 Caenorhabditis elegans cat-4 gene Proteins 0.000 description 1
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- 101100005280 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cat-3 gene Proteins 0.000 description 1
- 101100126846 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) katG gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000037123 dental health Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N p-menthan-3-ol Chemical compound CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105315133B (zh) * | 2015-11-17 | 2017-12-15 | 安徽海华科技股份有限公司 | 一种百里香酚合成工艺 |
CN107961779B (zh) * | 2017-11-24 | 2020-10-23 | 江西省隆南药化有限公司 | 一种用于合成麝香草酚的催化剂及其制备方法,及应用该催化剂制备麝香草酚的方法 |
CN112939739A (zh) * | 2021-01-11 | 2021-06-11 | 吴樟强 | 一种百里香酚的酸催化制备方法 |
CN113244905B (zh) * | 2021-05-31 | 2023-10-20 | 淮阴工学院 | 一种高效催化剂的制备方法及其在合成百里香酚中的应用 |
CN113896617B (zh) * | 2021-10-18 | 2022-04-05 | 安徽海华科技集团有限公司 | 一种香芹酚的化学合成工艺 |
CN114849769B (zh) * | 2022-04-25 | 2023-06-13 | 安徽海华科技集团有限公司 | 合成百里香酚用催化剂及其制备方法与应用 |
CN115959972A (zh) * | 2022-12-07 | 2023-04-14 | 万华化学集团股份有限公司 | 一种用于制备百里香酚的联苯二酚基铝催化剂和制备方法及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0716886A2 (de) * | 1994-12-15 | 1996-06-19 | Basf Aktiengesellschaft | Verfahren zur Herstellung im wesentlichen SiO2-freier Wabenkörper |
CN1143047A (zh) * | 1995-07-14 | 1997-02-19 | 余忠清 | 高纯超细分散球形al2o3粉末的制备方法 |
CN1762579A (zh) * | 2005-09-09 | 2006-04-26 | 清华大学 | 一种大孔容高比表面积氧化铝的制备方法 |
-
2014
- 2014-07-02 CN CN201410312426.0A patent/CN104190391B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0716886A2 (de) * | 1994-12-15 | 1996-06-19 | Basf Aktiengesellschaft | Verfahren zur Herstellung im wesentlichen SiO2-freier Wabenkörper |
CN1143047A (zh) * | 1995-07-14 | 1997-02-19 | 余忠清 | 高纯超细分散球形al2o3粉末的制备方法 |
CN1762579A (zh) * | 2005-09-09 | 2006-04-26 | 清华大学 | 一种大孔容高比表面积氧化铝的制备方法 |
Non-Patent Citations (2)
Title |
---|
γ-Al2O3催化间甲酚和丙烯烷基化合成百里香酚;何媛媛等;《精细石油化工》;20140531;第31卷(第3期);第5-10页 * |
百里香酚的研究进展;仇昆伦等;《香料香精化妆品》;20080430(第2期);第28-32页 * |
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Denomination of invention: A catalyst and its application in the preparation of thymol Granted publication date: 20160817 Pledgee: Industrial Bank Co.,Ltd. Shanghai Minhang sub branch Pledgor: SHANGHAI JINGWEI CHEMICAL TECHNOLOGY Co.,Ltd. Registration number: Y2024310000409 |