CN1883795A - 一种铜锌铝系气相醛加氢催化剂的制备方法及其产品 - Google Patents
一种铜锌铝系气相醛加氢催化剂的制备方法及其产品 Download PDFInfo
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- CN1883795A CN1883795A CN 200610091175 CN200610091175A CN1883795A CN 1883795 A CN1883795 A CN 1883795A CN 200610091175 CN200610091175 CN 200610091175 CN 200610091175 A CN200610091175 A CN 200610091175A CN 1883795 A CN1883795 A CN 1883795A
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- 238000007037 hydroformylation reaction Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000000975 co-precipitation Methods 0.000 claims abstract description 12
- 239000011148 porous material Substances 0.000 claims abstract description 8
- -1 copper-zinc-aluminum Chemical compound 0.000 claims abstract description 7
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 34
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 32
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 31
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 26
- 239000011259 mixed solution Substances 0.000 claims description 22
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 21
- 239000011787 zinc oxide Substances 0.000 claims description 16
- 238000006386 neutralization reaction Methods 0.000 claims description 15
- 230000032683 aging Effects 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 229960004643 cupric oxide Drugs 0.000 claims description 13
- 230000001376 precipitating effect Effects 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- 229910002804 graphite Inorganic materials 0.000 claims description 9
- 239000010439 graphite Substances 0.000 claims description 9
- 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 8
- 239000000463 material Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
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- 239000012452 mother liquor Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000005469 granulation Methods 0.000 claims description 3
- 230000003179 granulation Effects 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 24
- 229910052802 copper Inorganic materials 0.000 abstract description 23
- 239000010949 copper Substances 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 12
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 5
- 238000007086 side reaction Methods 0.000 abstract description 5
- 239000006185 dispersion Substances 0.000 abstract description 4
- 230000032050 esterification Effects 0.000 abstract description 4
- 238000005886 esterification reaction Methods 0.000 abstract description 4
- 230000000630 rising effect Effects 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 20
- 239000011701 zinc Substances 0.000 description 20
- 229910052725 zinc Inorganic materials 0.000 description 20
- 239000007789 gas Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 235000017550 sodium carbonate Nutrition 0.000 description 12
- 239000004411 aluminium Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical class [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000748 compression moulding Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 229910001676 gahnite Inorganic materials 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 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
- VODBHXZOIQDDST-UHFFFAOYSA-N copper zinc oxygen(2-) Chemical compound [O--].[O--].[Cu++].[Zn++] VODBHXZOIQDDST-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000036632 reaction speed Effects 0.000 description 3
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- 229910052596 spinel Inorganic materials 0.000 description 3
- 239000011029 spinel Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- AVERNHDYEFYHIV-UHFFFAOYSA-N dodecan-5-ol Chemical group CCCCCCCC(O)CCCC AVERNHDYEFYHIV-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910018576 CuAl2O4 Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- 239000012018 catalyst precursor Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 208000012839 conversion disease Diseases 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical class [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
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- 235000015320 potassium carbonate Nutrition 0.000 description 1
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- 238000003672 processing method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 238000005245 sintering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Catalysts (AREA)
Abstract
Description
比表面积,m2/g | 孔容,ml/g | 平均孔半径,nm | 侧压强度,N/cm | |
对比例1 | 40.4 | 0.17 | 8.40 | 156 |
对比例2 | 46.3 | 0.22 | 9.65 | 176 |
实施例1 | 69.4 | 0.22 | 6.35 | 238 |
实施例2 | 69.8 | 0.23 | 6.33 | 240 |
实施例3 | 69.3 | 0.21 | 6.35 | 245 |
对比例1 | 对比例2 | 实施例1 | 实施例2 | 实施例3 | |
辛烯醛转化率,wt% | 99.67 | 99.82 | 99.99 | 99.99 | 99.98 |
辛醇选择性,% | 97.62 | 99.63 | 99.75 | 99.80 | 99.84 |
对比例1 | 对比例2 | 实施例1 | 实施例2 | 实施例3 | |
正丁醛转化率,wt% | 99.87 | 99.94 | 99.99 | 99.99 | 99.98 |
正丁醇选择性,% | 99.78 | 99.76 | 99.80 | 99.81 | 99.78 |
对比例1 | 对比例2 | 实施例1 | 实施例2 | 实施例3 | |
辛烯醛转化率,重量% | 98.78 | 99.93 | 99.97 | 99.97 | 99.96 |
辛醇选择性,% | 96.89 | 99.12 | 99.32 | 99.33 | 99.29 |
正丁醛转化率,重量% | 99.82 | 99.90 | 99.98 | 99.98 | 99.96 |
丁醇选择性,% | 98.92 | 99.70 | 99.72 | 99.73 | 99.71 |
实施例5 | 实施例6 | 实施例7 | 实施例8 | 实施例9 | 实施例10 | ||
反应条件 | 中和时间 | 50min | 70min | 60min | 55min | 65min | 68min |
PH值 | 7.0 | 8.0 | 7.5 | 7.3 | 7.8 | 7.6 | |
老化时间 | 20min | 30min | 25min | 22min | 26min | 28min | |
产品中各物质的百分含量 | 氧化铜 | 10% | 50% | 60% | 40% | 30% | 35% |
氧化锌 | 20% | 75% | 80% | 60% | 55% | 65% | |
氧化铝 | 0.1% | 20% | 1% | 5% | 8% | 10% |
Claims (7)
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CNB2006100911753A CN100398202C (zh) | 2006-07-05 | 2006-07-05 | 一种铜锌铝系气相醛加氢催化剂的制备方法及其产品 |
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CN1883795A true CN1883795A (zh) | 2006-12-27 |
CN100398202C CN100398202C (zh) | 2008-07-02 |
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Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102350360A (zh) * | 2011-08-17 | 2012-02-15 | 中国石油化工集团公司 | 一种醛气相加氢催化剂及其制备方法 |
CN102407122A (zh) * | 2011-10-19 | 2012-04-11 | 西北化工研究院 | 一种辛烯醛气相加氢制辛醇的催化剂的制备方法 |
CN103100393A (zh) * | 2011-11-09 | 2013-05-15 | 中国石油化工股份有限公司 | 一种加氢催化剂及其制备方法 |
CN104275186A (zh) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | 4-甲基-2-戊醇脱氢催化剂及其制备方法和应用 |
CN104907071A (zh) * | 2014-03-13 | 2015-09-16 | 中国石油化工股份有限公司 | 酯加氢催化剂及其制备方法和酯加氢反应的方法 |
CN105562115A (zh) * | 2016-01-06 | 2016-05-11 | 中自环保科技股份有限公司 | 一种尾气净化催化剂载体材料及其制备方法 |
CN106582660A (zh) * | 2016-12-05 | 2017-04-26 | 万华化学集团股份有限公司 | 一种醛加氢制备醇的催化剂的制备方法 |
CN106732618A (zh) * | 2017-01-17 | 2017-05-31 | 西南化工研究设计院有限公司 | 一种水相分解制备铜基催化剂的方法 |
CN107519881A (zh) * | 2016-06-20 | 2017-12-29 | 中国石油化工股份有限公司 | 一种醋酸环己酯加氢催化剂的制备方法及所制备的加氢催化剂和醋酸环己酯的加氢方法 |
CN110624553A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 环己醇脱氢制环己酮催化剂的制备方法 |
CN112138669A (zh) * | 2020-09-30 | 2020-12-29 | 广东石油化工学院 | 一种连续化制备铜锌铝催化剂的方法 |
CN112791725A (zh) * | 2019-11-13 | 2021-05-14 | 中国石油天然气股份有限公司 | 一种气相醛加氢催化材料模块的制备方法及应用 |
CN114433098A (zh) * | 2020-10-20 | 2022-05-06 | 中国石油化工股份有限公司 | 一种催化剂及其制备方法和降低聚醚多元醇中醛含量的方法 |
CN114870847A (zh) * | 2022-04-28 | 2022-08-09 | 广东石油化工学院 | 铜锌铝系气相加氢催化剂的制备方法及制得催化剂与应用 |
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- 2006-07-05 CN CNB2006100911753A patent/CN100398202C/zh active Active
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102350360A (zh) * | 2011-08-17 | 2012-02-15 | 中国石油化工集团公司 | 一种醛气相加氢催化剂及其制备方法 |
CN102407122A (zh) * | 2011-10-19 | 2012-04-11 | 西北化工研究院 | 一种辛烯醛气相加氢制辛醇的催化剂的制备方法 |
CN103100393A (zh) * | 2011-11-09 | 2013-05-15 | 中国石油化工股份有限公司 | 一种加氢催化剂及其制备方法 |
CN103100393B (zh) * | 2011-11-09 | 2014-12-31 | 中国石油化工股份有限公司 | 一种加氢催化剂及其制备方法 |
CN104275186A (zh) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | 4-甲基-2-戊醇脱氢催化剂及其制备方法和应用 |
CN104907071B (zh) * | 2014-03-13 | 2017-07-25 | 中国石油化工股份有限公司 | 酯加氢催化剂及其制备方法和酯加氢反应的方法 |
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CN107519881A (zh) * | 2016-06-20 | 2017-12-29 | 中国石油化工股份有限公司 | 一种醋酸环己酯加氢催化剂的制备方法及所制备的加氢催化剂和醋酸环己酯的加氢方法 |
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CN106582660B (zh) * | 2016-12-05 | 2019-04-23 | 万华化学集团股份有限公司 | 一种醛加氢制备醇的催化剂的制备方法 |
CN106732618A (zh) * | 2017-01-17 | 2017-05-31 | 西南化工研究设计院有限公司 | 一种水相分解制备铜基催化剂的方法 |
CN110624553A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 环己醇脱氢制环己酮催化剂的制备方法 |
CN110624553B (zh) * | 2018-06-25 | 2022-08-23 | 中国石油化工股份有限公司 | 环己醇脱氢制环己酮催化剂的制备方法 |
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