CN1094789C - 1，4－丁二醇脱氢制备γ－丁内酯催化剂及其用途 - Google Patents
1，4－丁二醇脱氢制备γ－丁内酯催化剂及其用途 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 35
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000006356 dehydrogenation reaction Methods 0.000 title claims abstract description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 230000004913 activation Effects 0.000 claims abstract description 3
- 230000009467 reduction Effects 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 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 description 4
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- -1 pyrrolidine ketone Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
一种1，4-丁二醇脱氢制备γ-丁内酯催化剂其组成为：CuO 30-70% ZnO15-40% Al2O3 2-24%助剂0.001-9%，其中助剂由BaO、Pd两种物质中的至少一种制备而成。该催化剂在氢气气氛中还原活化，然后装入固定床反应器内，反应温度200-260℃，反应压力小于0.05MPa，液体空速0.1-1.2hr-1下应用。本发明具有较高的活性和选择性，1，4-丁二醇转化率100%，γ-丁内酯选择性大于96%，催化剂中不含Cr的优点。
Description
本发明属于一种催化剂及其用途，具体涉及一种用于1，4-丁二醇脱氢制备γ-丁内酯催化剂及其用途。
γ-丁内酯又称1，4-丁内酯，是一种重要的有机化工产品，广泛应用石油化工、医药、染料、农药及精细化工方面，近年来尤其在合成吡咯烷酮、N-甲基吡咯烷酮、乙烯基吡咯烷酮、α-乙酰基丁内酯等重要产品中应用量较大。另外γ-丁内酯还是高沸点溶剂，溶解力强，导电性和稳定性好，使用和管理安全方便。
目前世界上主要有两种原料路线生产γ-丁内酯，即1，4-丁二醇脱氢法和顺酐加氢法。而1，4-丁二醇路线是工业上主要采用的方法。
日本专利JP0525,151，报导1，4-丁二醇气相脱氢制备γ-丁内酯，其催化剂由Cu、Cr、Na或K组成。在230℃，空速3.0hr-1条件下，转化率87.28％，选择性98.75％。
欧州专利EP523,774，介绍使用Cu-Cr-Ba或Cu-Cr-Mn-Ba，其中加入碱金属Na或K。在固定床反应器中，催化剂组成为Cu 33.5％，Cr28.6％，Mn 4.0％和Na 2.2％，在温度为230℃，压力0.4MPa，氢醇比4，空速3.0hr-1条件下，1，4-丁二醇转化率91.39％，γ-丁内酯选择性93.98％。
日本专利JP03,232,874，公开的催化剂组成为CuO 47％，Cr2O342％，BaO 6％，在230℃，0.3MPa条件下，1，4-丁二醇脱氢制γ-丁内酯转化率为96.1％，选择性为95.1％。
中国专利CN1221000A报导其催化剂具有如下通式组成：CuCraMnbAcOx
其中A选自Ti、Al、Zr、Zn，a＝0.5-2.0，b＝0.01-1.5，c＝0.01-2.0，x为满足各金属元素化合价的氧原子数。1，4-丁二醇转化率96％以上，γ-丁内酯选择性在98％以上。
以上这些专利催化剂中均含有Cr元素，易造成环境污染，对人体健康有害。
本发明的目的在于提供一种具有活性高，选择性好，不含Cr的1，4-丁二醇脱氢制γ-丁内酯催化剂及其用途。
本发明的催化剂，各组份重量百分比为：
CuO 30-70％ ZnO 15-40％
Al2O3 2-24％ 助剂 0.001-9％
其中助剂由BaO、Pd两种物质中的至少一种制备而成。
如上所述的Al2O3最好为5-16％。
本发明的催化剂是采用沉淀法制备的，具体步骤如下：
(1)按催化剂的组成配制硝酸盐混合液，浓度为1-2M；
(2)将硝酸盐混合液和碱性沉淀剂在搅拌下混合，得到沉淀，搅拌混合的温度为50-60℃，时间为1小时，然后老化1小时；
(3)沉淀后经洗涤过滤，在100-110℃干燥12小时，并在350℃下焙烧4小时，最后加入少于2％的石墨粉成型，制得催化剂。
本催化剂用于1，4-丁二醇气相常压脱氢制γ-丁内酯，催化剂装填在固定床反应器内，反应条件是：反应温度200-260℃，反应压力小于0.05MPa，氢醇摩尔比3-35，1，4-丁二醇重量空速0.1-1.2hr-1。催化剂使用前需在氢气气氛中还原活化。反应结果是：1，4-丁二醇转化率约100％，γ-丁内酯选择性大于96％。
本发明的催化剂与现有技术相比具有如下优点：
1.催化剂具有较高的活性和选择性，1，4-丁二醇转化率100％，γ-丁内酯选择性大于96％。
2.催化剂中不含Cr，降低了环境污染。
本发明的实施例如下：
实施例1
(1)制备过程：称取硝酸铜126.2g，硝酸锌124.3g，硝酸铝117.7g，硝酸钡13.6g，将硝酸盐溶于蒸馏水中，配制成约1400ml溶液，该溶液和碱性沉淀剂在50-60℃下搅拌，混合得到沉淀，然后老化1hr。沉淀物经洗涤过滤，在110℃干燥12小时，并在350℃焙烧4小时，得约100g催化剂，最后加入少量石墨(一般小于2％)成型；
(2)催化剂(焙烧后)组成wt％为：CuO 41.5％，ZnO 34％，Al2O316％，助剂BaO 8％；
(3)反应性能：催化剂(20-40目)装填于反应器(Φ12×600mm)内，常压，温度205℃，空速0.2hr-1，氢醇摩尔比12条件下，1，4-丁二醇转化率约100％，γ-丁内酯选择性96.8％。
实施例2
(1)催化剂(焙烧后)组成wt％为：CuO 48％，ZnO 31％，Al2O315％，助剂BaO 5％，Pd 0.005％；
(2)制备过程：称取硝酸铜145.9g，硝酸锌113.3g，硝酸铝110.4g，硝酸钡8.5g，1.0mg/ml钯溶液5ml，其余同实施例1。
(3)反应性能：在常压，温度225℃，空速0.43hr-1，氢醇摩尔比25条件下，1，4-丁二醇转化率约100％，γ-丁内酯选择性98.3％。
实施例3
(1)催化剂(焙烧后)组成wt％为：CuO 51％，ZnO 30％，Al2O318％，助剂Pd 0.05％；
(2)制备过程：称取硝酸铜155.1g，硝酸锌109.7g，硝酸铝132.4g，1.0mg/ml钯溶液50ml，其余同实施例1；
(3)反应性能：在常压，温度247℃，空速0.7hr-1，氢醇摩尔比30条件下，转化率约100％，γ-丁内酯选择性97.8％。
实施例4
(1)催化剂(焙烧后)组成wt％为：CuO 62％，ZnO 28％，Al2O3 8％，助剂BaO 2％，Pd 0.04％；
(2)制备过程：称取硝酸铜188.5g，硝酸锌102.3g，硝酸铝58.9g，硝酸钡3.4g，1.0mg/ml(钯溶液)40ml，其余同实施例1；
(3)反应性能：常压，温度258℃，空速0.95hr-1，氢醇摩尔比34条件下，转化率约100％，γ-丁内酯选择性98.7％。
Claims (3)
1. 1，4-丁二醇脱氢制备γ-丁内酯催化剂，催化剂的各组份重量百分比为：
CuO 30-70％ ZnO 15-40％
Al2O3 2-24％ 助剂 0.001-9％
其中助剂由BaO、Pd两种物质中的至少一种制备而成。
2.根据权利要求1所述的一种1，4-丁二醇脱氢制备γ-丁内酯催化剂，其特征在于所述的Al2O3为5-16％。
3.一种1，4-丁二醇脱氢制备γ-丁内酯催化剂的用途，其特征在于催化剂在氢气气氛中还原活化，然后装入固定床反应器内，反应温度200-260℃，反应压力小于0.05MPa，液体空速0.1-1.2hr-1。
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| CN00121572A CN1094789C (zh) | 2000-08-14 | 2000-08-14 | 1，4－丁二醇脱氢制备γ－丁内酯催化剂及其用途 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102380391A (zh) * | 2010-08-26 | 2012-03-21 | 中科合成油技术有限公司 | 选择性脱酸催化剂及其制备方法、以及其在对费托合成油进行选择性加氢脱酸处理中的应用 |
| CN103044367B (zh) * | 2011-10-17 | 2014-12-31 | 中国石油化工股份有限公司 | 一种γ-丁内酯的生产方法 |
| CN103657658B (zh) * | 2012-09-18 | 2015-11-25 | 中国石油化工股份有限公司 | 羧酸酯加氢催化剂及制备环己醇和乙醇的方法 |
| CN103769110B (zh) * | 2012-10-24 | 2016-11-09 | 中国石油化工股份有限公司 | 一种1，4-丁二醇脱氢制γ-丁内酯催化剂及其制备方法和应用 |
| CN115367702A (zh) * | 2022-07-25 | 2022-11-22 | 朱义峰 | 一种用于氢燃料电池的在线供氢系统及方法 |
| CN115779957B (zh) * | 2022-12-10 | 2024-03-19 | 南通格瑞凯泰工程技术有限公司 | 1,4-丁二醇低压脱氢制γ-丁内酯用催化剂及其应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1058400A (zh) * | 1991-08-28 | 1992-02-05 | 复旦大学 | 顺酐常压气相加氢合成γ-丁内酯 |
| US5196602A (en) * | 1991-12-30 | 1993-03-23 | The Standard Oil Company | Two-stage maleic anhydride hydrogenation process for 1,4-butanediol synthesis |
| CN1111167A (zh) * | 1994-05-05 | 1995-11-08 | 化学工业部北京化工研究院 | 顺酐气相加氢制γ-丁内酯的催化剂 |
| US5478952A (en) * | 1995-03-03 | 1995-12-26 | E. I. Du Pont De Nemours And Company | Ru,Re/carbon catalyst for hydrogenation in aqueous solution |
| CN1298759A (zh) * | 1999-12-08 | 2001-06-13 | 中国科学院山西煤炭化学研究所 | 顺酐气相常压加氢制γ－丁内酯催化剂及其用途 |
-
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- 2000-08-14 CN CN00121572A patent/CN1094789C/zh not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1058400A (zh) * | 1991-08-28 | 1992-02-05 | 复旦大学 | 顺酐常压气相加氢合成γ-丁内酯 |
| US5196602A (en) * | 1991-12-30 | 1993-03-23 | The Standard Oil Company | Two-stage maleic anhydride hydrogenation process for 1,4-butanediol synthesis |
| CN1111167A (zh) * | 1994-05-05 | 1995-11-08 | 化学工业部北京化工研究院 | 顺酐气相加氢制γ-丁内酯的催化剂 |
| US5478952A (en) * | 1995-03-03 | 1995-12-26 | E. I. Du Pont De Nemours And Company | Ru,Re/carbon catalyst for hydrogenation in aqueous solution |
| CN1298759A (zh) * | 1999-12-08 | 2001-06-13 | 中国科学院山西煤炭化学研究所 | 顺酐气相常压加氢制γ－丁内酯催化剂及其用途 |
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