CN108929189A - 一种由α,α-二甲基苄醇氢解制备异丙苯的方法 - Google Patents
一种由α,α-二甲基苄醇氢解制备异丙苯的方法 Download PDFInfo
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- CN108929189A CN108929189A CN201810893308.1A CN201810893308A CN108929189A CN 108929189 A CN108929189 A CN 108929189A CN 201810893308 A CN201810893308 A CN 201810893308A CN 108929189 A CN108929189 A CN 108929189A
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- isopropylbenzene
- hydrogenolysis
- dimethyl benzylalcohol
- nano diamond
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- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 title claims abstract description 95
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000007327 hydrogenolysis reaction Methods 0.000 title claims abstract description 33
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000002113 nanodiamond Substances 0.000 claims abstract description 29
- 229910017518 Cu Zn Inorganic materials 0.000 claims abstract description 16
- 229910017752 Cu-Zn Inorganic materials 0.000 claims abstract description 16
- 229910017943 Cu—Zn Inorganic materials 0.000 claims abstract description 16
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims abstract description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000010949 copper Substances 0.000 claims description 20
- 239000002994 raw material Substances 0.000 claims description 18
- 239000012159 carrier gas Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000007598 dipping method Methods 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 5
- 238000000527 sonication Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002525 ultrasonication Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000003751 zinc Chemical class 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical group [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001354 calcination Methods 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000004880 explosion Methods 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052754 neon Inorganic materials 0.000 claims description 2
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 7
- 238000004064 recycling Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 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 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- FTXJFNVGIDRLEM-UHFFFAOYSA-N copper;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O FTXJFNVGIDRLEM-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- 229910017813 Cu—Cr Inorganic materials 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000010954 commercial manufacturing process Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000007616 round robin method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/647—2-50 nm
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with zinc, cadmium or mercury
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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
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Abstract
本发明公开了一种由α,α‑二甲基苄醇氢解制备异丙苯的方法,采用Cu‑Zn/碳纳米金刚石催化剂,催化α,α‑二甲基苄醇氢解制备异丙苯,α,α‑二甲基苄醇转化率为100%,异丙苯选择性为98.9%以上,取得了较好的技术效果,且产品易于分离,后处理简单等特点,所用的催化剂还可回收重复利用。
Description
技术领域
本发明涉及一种制备异丙苯的方法,特别是关于一种由α,α-二甲基苄醇氢解制备异丙苯的方法。
背景技术
异丙苯(Isopropylbenzene,Cumene,CAS:98-82-8),一种无色有特殊芳香气味的液体,用作有机合成原料及提高发动机燃料辛烷值的添加剂。
工业上由苯与丙烯进行烷基化反应而得。通常采用三氯化铝为催化剂、氯化氢为促进剂,反应在常压和95℃左右进行。除生成异丙苯外,还有二异丙苯、三异丙苯等多烷基副产物生成。为了减少副反应可采用过量的苯,苯与丙烯的摩尔比为3左右;三氯化铝在反应液中的含量为3%-8%;在低的丙烯浓度下进行反应。为提高反应器的生产能力,减少尾气中苯的损失,可将反应压力提高到0.5-0.6MPa。反应所得的烷基化液经冷却、沉淀后分离出的固体(三氯化铝与多异丙苯络合物)循环使用。烷基化液则经水解、中和、精馏而得异丙苯。
另一种气相法工艺过程,是将气态苯和丙烯通过载于氧化铝或硅酸铝上的磷酸催化床层,进行催化烷基化,反应压力1.5-40MPa,温度约250℃。目前工业上生产异丙苯以上述液相法为主。
当前环氧丙烷(简称PO)的商业化生产工艺主要有三种,氯醇法,共氧化法(PO/SM)以及过氧化异丙苯循环法(CHP)。目前采用氯醇化法、共氧化法的环氧丙烷装置占全世界环氧丙烷总生产能力的99%以上,其中氯醇化法约占45%共氧化法约占54%;在共氧化法中,乙苯法为33%,异丁烷法为18%,过氧化氢异丙苯法为3%。过氧化氢路线与直接氧化路线由于丙稀低的转化率相对比较低,导致其经济性不理想,尤其是过氧化氢路线中有水的产生导致原料的损失。日本Sumitomo公司开发的生产PO新工艺,包括异丙苯氧化,丙烯环氧化与α,α-二甲基苄醇氢解三个工序。该工艺转化率高与选择性高,产物只有PO,不受副产物苯乙烯价格波动的影响,可以为生产商带来更稳定的经济效益。然而,其中α,α-二甲基苄醇氢解工序采用的是Cu-Cr催化剂,污染环境严重。
美国专利US6646139B2提出了α,α-二甲基苄醇催化氢解制备异丙苯的工艺过程,该技术以H2为氢源,以Cu-Cr为催化剂。虽然α,α-二甲基苄醇的转化率达到100%,选择性超过97.5%。该催化剂使用中使用了Cr元素,污染环境严重。
目前氢解催化剂主要集中在Raney金属催化剂和Cu基复合催化剂。Raney金属催化剂强度不高,易粉碎且在使用前需强碱处理,对环境污染比较严重,实现工艺化连续生产存在一定困难;因此,Cu基复合氧化物催化剂受到广泛关注,但由于单质Cu熔点低,与载体作用力不强,容易因烧结、团聚而长大、失活,因而在使用过程中,稳定性差较差,使用寿命短。
中国专利CN104230640A公开了一种由α,α-二甲基苄醇氢解制备异丙苯的方法,所用催化剂以重量份数计包括以下组分:a)0.1~2.0份Pd金属或氧化物;b)85.0~97.0份SiO2;c)1.0~10.0份选自Ni或其氧化物、Cu或其氧化物、Cu或其氧化物中的至少一种;d)1.0~5.0份选自Mg或其氧化物、Ca或其氧化物、Ba或其氧化物中的至少一种。中国专利CN104230642A一种α,α-二甲基苄醇直接氢解制备异丙苯的方法,所用催化剂以重量份数计包括以下组分:a)0.2~2.0份Pd;b)91.0~98.0份活性炭;c)1.0~10.0份选自Ni或其氧化物、Cu或其氧化物、Cu或其氧化物、Sn或其氧化物中的至少一种;虽然催化剂稳定性有所特高,但还需采用贵金属Pd作为催化剂,催化剂成本较高,容易造成中金属污染不利于工业化生产。
综上所述,现有技术应用于α,α-二甲基苄醇催化氢解制备异丙苯过程中,存在催化剂稳定性差、成本高、环境污染严重的问题。
发明内容
本发明所要解决的技术问题是现有的技术在生产异丙苯的过程中,使用含铬催化剂对环境造成污染,或者使用Pd催化剂时,贵金属的用量大,生产成本高,另外催化剂不稳定的问题,提供一种新的异丙苯生产方法。该方法具有使用催化剂的成本低、催化剂稳定以及对环境友好等优点。
为解决上述技术问题,本发明采用的技术方案如下:
一种由α,α-二甲基苄醇氢解制备异丙苯的方法,以含α,α-二甲基苄醇与氢气为原料,将原料与惰性载气通入氢解反应区,原料气/惰性载气的摩尔比为1:10~20,氢气/α,α-二甲基苄醇的摩尔比为3~15:1,反应温度为100~200℃,反应压力为0.2~0.9MPa,惰性载气的体积空速为1.0~10.0小时-1的条件下,原料与催化剂接触反应生成异丙苯;其中所用催化剂为Cu-Zn/碳纳米金刚石,Cu的摩尔含量为0.5~5%;Zn的摩尔含量为1~10%。
所述催化剂的孔径优选10~15nm,比表面积优选300~400m2/g、总孔体积优选0.1~2.0cm3/g,所述纳米金刚石采用爆炸法生产。
所述惰性载气选自氮气、氦气、氖气、甲烷中的任一种或多种。
上述技术方案中,氢气/α,α-二甲基苄醇的摩尔比优选为5~12;反应温度优选为160~210℃;反应压力优选为0.1~0.4MPa;惰性载气的体积空速优选为2.0~8.0h-1。
上述技术方案中,含α,α-二甲基苄醇烃类物料中以重量百分比计优选含有15~40%的α,α-二甲基苄醇,60~85%的异丙苯。
所述Cu-Zn/碳纳米金刚石的制备方法包括如下步骤:
(1)将纳米金刚石在惰性气体中于900~1200℃焙烧,将纳米金刚石在惰性气体中的焙烧温度优选1000~1200℃;所述的惰性气体优选氮气;焙烧时间优选2~20h、更优选4~18h;
(2)将铜盐和锌盐溶解在溶剂中,制备含有铜和锌的溶液,然后放入步骤(1)所述制备的纳米金刚石,先使用超声波处理,再搅拌浸渍,所述超声处理时间优选0.5~5h,搅拌浸渍时间优选10~50小时;
(3)浸渍负载Cu-Zn后,将纳米金刚石在空气中干燥,干燥温度优选60~150℃,干燥后进行还原,即得Cu-Zn/碳纳米金刚石催化剂。
进一步地,所述步骤(2)中的铜盐为硝酸铜或氯化铜。
进一步地,所述步骤(2)中的锌盐为硝酸锌或氯化锌。
进一步地,所述步骤(2)所用溶剂为N,N-二甲基甲酰胺。
进一步地,步骤(2)中浸渍时的液/固比优选50~70mL/g,浸渍温度优选15~45℃;浸渍所用含铜化合物溶液中铜含量优选0.05~2.0mg/mL、更优选0.3~1.0mg/mL,浸渍所用含锌化合物溶液中铜含量优选0.2~4.0mg/mL、更优选0.8~2.0mg/mL。
进一步地,步骤(3)中所述的还原用氢气还原,还原温度优选500~600℃,还原时间优选0.5~10小时。
采用过氧化异丙苯法制备环氧丙烷过程中,异丙苯首先氧化生成过氧化异丙苯,过氧化异丙苯与丙烯反应生成环氧丙烷和α,α-二甲基苄醇,α,α-二甲基苄醇可通过氢解反应重新生成异丙苯,实现循环使用。α,α-二甲基苄醇氢解过程中,混合原料中存在的胶质、丙二醇醚类聚合物会沉积在催化剂表面,导致氢解活性下降甚至失活,需要严格控制原料胶质及重组分含量。异丙苯过度加氢将生成异丙基环己烷,该反应为放热反应。如果催化剂加氢活性过高,在导致异丙苯的苯环加氢。苯环加氢放热量很大,如果该反应大量发生将导致温升剧烈,甚至造成飞温难以控制。同时较高的反应温度和氢气分压也会促进该副反应的发生。异丙基环己烷从异丙苯中分离极为困难,因此需要采用加氢性能适中的催化剂并且严格控制工艺条件,尽量减少异丙基环己烷的生成。当催化剂活性降低时,反应产物中会有并异丙苯生成。因为并异丙苯是由二甲基α,α-二甲基苄醇或异丙苯生成的,实际上并异丙苯的生成造成了异丙苯的损失。并异丙苯的生成主要是由于催化剂运行过程中活性下降导致的。反应过程中当金属加氢活性降低的时候,产物中会有甲基苯乙烯的生成。为抑制甲基苯乙烯的生成,可以通过适当提高反应温度或者提高氢气分压。在较高的反应高温下会促进有机分子聚合、结焦甚至导致积碳的发生,原料中重组分以及不饱和易聚合化合物越多,聚合、结焦的倾向愈大,虽然在氢气气氛下该反应将会受到抑制。本发明通过采用加入适宜助剂的催化剂及适宜工艺条件进行α,α-二甲基苄醇氢解反应。
采用本发明的技术方案,采用Cu-Zn/碳纳米金刚石催化剂,在反应入口温度180℃,反应压力3.0MPa,H2/α,α-二甲基苄醇的摩尔比10.0,液体体积空速6.0h-1的条件下反应240h,α,α-二甲基苄醇转化率为100%,异丙苯选择性为98.9%以上,取得了较好的技术效果。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动的前提下所获得的所有其他实施例,都属于本发明保护的范围。
【实施例1】
S1、催化剂的制备
(1)取粒径为30nm的纳米金刚石ND-30,在N2中于1100℃焙烧18小时。
(2)称取0.5471g六水硝酸铜[Cu(NO3)2·6H2O]和0.5593g六水硝酸锌[Zn(NO3)2·6H2O]全溶解于30mLN,N-2甲基甲酰胺(DMF)中,然后放入0.7g步骤(1)所述制备的纳米金刚石,先使用超声波处理,再搅拌浸渍,所述超声处理时间为0.6h,搅拌浸渍时间优选15小时。
(3)浸渍负载Cu-Zn后,将纳米金刚石在空气中干燥,干燥温度为80℃,干燥后进行还原,还原用氢气还原,还原温度为550℃,还原时间优选8小时,即得Cu-Zn/碳纳米金刚石催化剂。
S2、氢解反应
将40.0ml步骤S1所制备的催化剂装入固定床反应器,以α,α-二甲基苄醇与氢气为原料,将原料与氮气通入氢解反应区,原料气/氮气的摩尔比为1:15,氢气/α,α-二甲基苄醇的摩尔比为5:1,反应温度为120℃,反应压力为0.5MPa,惰性载气的体积空速为3.0小时-1的条件下,原料与催化剂接触反应生成异丙苯,经检测α,α-二甲基苄醇转化率为100%,异丙苯的选择性为99.3%。
【实施例2】
S1、催化剂的制备
(1)取粒径为30nm的纳米金刚石ND-30,在N2中于1100℃焙烧18小时。
(2)首先称取0.0274g六水硝酸铜[Cu(NO3)2·6H2O]和0.5593g六水硝酸锌[Zn(NO3)2·6H2O]全溶解于30mLN,N-2甲基甲酰胺(DMF)中,然后放入0.7g步骤(1)所述制备的纳米金刚石,先使用超声波处理,再搅拌浸渍,所述超声处理时间为0.6h,搅拌浸渍时间优选15小时。
(3)浸渍负载Cu-Zn后,将纳米金刚石在空气中干燥,干燥温度为80℃,干燥后进行还原,还原用氢气还原,还原温度为550℃,还原时间优选8小时,即得Cu-Zn/碳纳米金刚石催化剂。
S2、氢解反应
将40.0ml步骤S1所制备的催化剂装入固定床反应器,以α,α-二甲基苄醇与氢气为原料,将原料与氮气通入氢解反应区,原料气/氮气的摩尔比为1:15,氢气/α,α-二甲基苄醇的摩尔比为5:1,反应温度为120℃,反应压力为0.5MPa,惰性载气的体积空速为3.0小时-1的条件下,原料与催化剂接触反应生成异丙苯,经检测α,α-二甲基苄醇转化率为100%,异丙苯的选择性为98.9%。
【实施例3】
(1)取粒径为50nm的纳米金刚石ND-30,在N2中于1000℃焙烧16小时。
(2)首先称取0.0547g六水硝酸铜[Cu(NO3)2·6H2O]和0.5593g六水硝酸锌[Zn(NO3)2·6H2O]全溶解于30mLN,N-2甲基甲酰胺(DMF)中,然后放入0.5g步骤(1)所述制备的纳米金刚石,先使用超声波处理,再搅拌浸渍,所述超声处理时间为0.6h,搅拌浸渍时间优选15小时。
(3)浸渍负载Cu-Zn后,将纳米金刚石在空气中干燥,干燥温度为80℃,干燥后进行还原,还原用氢气还原,还原温度为550℃,还原时间优选8小时,即得Cu-Zn/碳纳米金刚石催化剂。
S2、氢解反应
将40.0ml步骤S1所制备的催化剂装入固定床反应器,以α,α-二甲基苄醇与氢气为原料,将原料与氮气通入氢解反应区,原料气/氮气的摩尔比为1:15,氢气/α,α-二甲基苄醇的摩尔比为5:1,反应温度为120℃,反应压力为0.5MPa,惰性载气的体积空速为3.0小时-1的条件下,原料与催化剂接触反应生成异丙苯,经检测α,α-二甲基苄醇转化率为100%,异丙苯的选择性为99.2%。
上述说明已经充分揭露了本发明的具体实施方式。需要指出的是,熟悉该领域的技术人员对本发明的具体实施方式所做的任何改动均不脱离本发明的权利要求书的范围。相应地,本发明的权利要求的范围也并不仅仅局限于前述具体实施方式。
Claims (9)
1.一种由α,α-二甲基苄醇氢解制备异丙苯的方法,以含α,α-二甲基苄醇与氢气为原料,将原料与惰性载气通入氢解反应区,原料气/惰性载气的摩尔比为1:10~20,氢气/α,α-二甲基苄醇的摩尔比为3~15:1,反应温度为100~200℃,反应压力为0.2~0.9MPa,惰性载气的体积空速为1.0~10.0小时-1的条件下,原料与催化剂接触反应生成异丙苯;其中所用催化剂为Cu-Zn/碳纳米金刚石,Cu的摩尔含量为0.5~5%;Zn的摩尔含量为1~10%;所述催化剂的孔径优选10~15nm,比表面积优选300~400m2/g、总孔体积优选0.1~2.0cm3/g,所述纳米金刚石采用爆炸法生产。
2.根据权利要求1所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于,所述惰性载气选自氮气、氦气、氖气、甲烷中的任一种或多种。
3.根据权利要求1所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于,氢气/α,α-二甲基苄醇的摩尔比优选为5~12;反应温度优选为160~210℃;反应压力优选为0.1~0.4MPa;惰性载气的体积空速优选为2.0~8.0h-1。
4.根据权利要求1所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于,所述Cu-Zn/碳纳米金刚石的制备方法包括如下步骤:
(1)将纳米金刚石在惰性气体中于900~1200℃焙烧,将纳米金刚石在惰性气体中的焙烧温度优选1000~1200℃;所述的惰性气体优选氮气;焙烧时间优选2~20h、更优选4~18h;
(2)将铜盐和锌盐溶解在溶剂中,制备含有铜和锌的溶液,然后放入步骤(1)所述制备的纳米金刚石,先使用超声波处理,再搅拌浸渍,所述超声处理时间优选0.5~5h,搅拌浸渍时间优选10~50小时;
(3)浸渍负载Cu-Zn后,将纳米金刚石在空气中干燥,干燥温度优选60~150℃,干燥后进行还原,即得Cu-Zn/碳纳米金刚石催化剂。
5.根据权利要求4所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于:所述铜盐为硝酸铜或氯化铜。
6.根据权利要求4所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于:所述锌盐为硝酸锌或氯化锌。
7.根据权利要求4所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于:步骤(2)所用溶剂为N,N-二甲基甲酰胺。
8.根据权利要求4所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于:步骤(2)中浸渍时的液/固比优选50~70mL/g,浸渍温度优选15~45℃;浸渍所用含铜化合物溶液中铜含量优选0.05~2.0mg/mL、更优选0.3~1.0mg/mL,浸渍所用含锌化合物溶液中铜含量优选0.2~4.0mg/mL、更优选0.8~2.0mg/mL。
9.根据权利要求4所述的由α,α-二甲基苄醇氢解制备异丙苯的方法,其特征在于:步骤(3)中所述的还原用氢气还原,还原温度优选500~600℃,还原时间优选0.5~10小时。
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110075857A (zh) * | 2019-05-09 | 2019-08-02 | 万华化学集团股份有限公司 | 一种二甲基苄醇氢解催化剂及其制备方法 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004203753A (ja) * | 2002-12-24 | 2004-07-22 | Sumitomo Chem Co Ltd | クメンの製造方法 |
CN1553886A (zh) * | 2001-09-13 | 2004-12-08 | ס�ѻ�ѧ��ҵ��ʽ���� | 异丙苯的制造方法 |
CN101992098A (zh) * | 2009-08-31 | 2011-03-30 | 中国石油化工股份有限公司 | α,α-二甲基苄醇氢解制异丙苯的铜催化剂及其制备方法 |
CN104411404A (zh) * | 2012-06-22 | 2015-03-11 | 克拉里安特国际有限公司 | 含石墨的催化剂成型体 |
-
2018
- 2018-08-07 CN CN201810893308.1A patent/CN108929189B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1553886A (zh) * | 2001-09-13 | 2004-12-08 | ס�ѻ�ѧ��ҵ��ʽ���� | 异丙苯的制造方法 |
JP2004203753A (ja) * | 2002-12-24 | 2004-07-22 | Sumitomo Chem Co Ltd | クメンの製造方法 |
CN101992098A (zh) * | 2009-08-31 | 2011-03-30 | 中国石油化工股份有限公司 | α,α-二甲基苄醇氢解制异丙苯的铜催化剂及其制备方法 |
CN104411404A (zh) * | 2012-06-22 | 2015-03-11 | 克拉里安特国际有限公司 | 含石墨的催化剂成型体 |
Non-Patent Citations (2)
Title |
---|
王春雷等: "碳纳米材料及其在多相催化中的应用 ", 《化学进展》 * |
马静萌等: "CuO-ZnO-MnOx/Al2O3催化剂上α,α-二甲基苄醇氢解制备异丙苯", 《石油化工》 * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2809251C2 (ru) * | 2019-08-09 | 2023-12-08 | Сумитомо Кемикал Компани, Лимитед | Способ получения кумола |
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