CN102658162B - 一种用于合成乙撑胺的催化剂及制备乙撑胺的方法 - Google Patents
一种用于合成乙撑胺的催化剂及制备乙撑胺的方法 Download PDFInfo
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- CN102658162B CN102658162B CN201210108743.1A CN201210108743A CN102658162B CN 102658162 B CN102658162 B CN 102658162B CN 201210108743 A CN201210108743 A CN 201210108743A CN 102658162 B CN102658162 B CN 102658162B
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- Prior art keywords
- catalyst
- carrier
- ammonia
- active component
- auxiliary agent
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- 239000003054 catalyst Substances 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 title claims abstract description 34
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 title abstract description 24
- 230000002194 synthesizing effect Effects 0.000 title abstract description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229910004298 SiO 2 Inorganic materials 0.000 claims abstract description 23
- 229910052796 boron Inorganic materials 0.000 claims abstract description 16
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 7
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 6
- 229910052802 copper Inorganic materials 0.000 claims abstract description 5
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 5
- 229910052742 iron Inorganic materials 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 52
- 229910021529 ammonia Inorganic materials 0.000 claims description 23
- 239000012298 atmosphere Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 7
- 238000004176 ammonification Methods 0.000 claims description 6
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 48
- 229910018072 Al 2 O 3 Inorganic materials 0.000 abstract description 42
- 230000000694 effects Effects 0.000 abstract description 13
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 33
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 235000012239 silicon dioxide Nutrition 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 17
- 229910021641 deionized water Inorganic materials 0.000 description 17
- 239000010453 quartz Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000011156 evaluation Methods 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 230000008569 process Effects 0.000 description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 4
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052681 coesite Inorganic materials 0.000 description 3
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- 229910052682 stishovite Inorganic materials 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910017813 Cu—Cr Inorganic materials 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
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
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- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
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- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
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- C—CHEMISTRY; METALLURGY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210108743.1A CN102658162B (zh) | 2012-04-13 | 2012-04-13 | 一种用于合成乙撑胺的催化剂及制备乙撑胺的方法 |
| IN7644DEN2014 IN2014DN07644A (enrdf_load_stackoverflow) | 2012-04-13 | 2012-05-24 | |
| PCT/CN2012/075989 WO2013152548A1 (zh) | 2012-04-13 | 2012-05-24 | 一种用于合成乙撑胺的催化剂及制备乙撑胺的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210108743.1A CN102658162B (zh) | 2012-04-13 | 2012-04-13 | 一种用于合成乙撑胺的催化剂及制备乙撑胺的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102658162A CN102658162A (zh) | 2012-09-12 |
| CN102658162B true CN102658162B (zh) | 2013-10-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201210108743.1A Active CN102658162B (zh) | 2012-04-13 | 2012-04-13 | 一种用于合成乙撑胺的催化剂及制备乙撑胺的方法 |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN102658162B (enrdf_load_stackoverflow) |
| IN (1) | IN2014DN07644A (enrdf_load_stackoverflow) |
| WO (1) | WO2013152548A1 (enrdf_load_stackoverflow) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106607060B (zh) * | 2015-10-26 | 2019-08-20 | 中国石油化工股份有限公司 | 催化剂及其制备方法和应用以及乙二醇临氢胺化制乙二胺的方法 |
| CN106669824A (zh) * | 2015-11-05 | 2017-05-17 | 南通市永顺化工有限公司 | 一种用于制备乙撑胺的催化剂 |
| CN106669826A (zh) * | 2015-11-05 | 2017-05-17 | 南通市永顺化工有限公司 | 一种用于制备乙撑胺的催化剂 |
| CN106669835A (zh) * | 2015-11-05 | 2017-05-17 | 南通市永顺化工有限公司 | 一种用于制备乙撑胺的催化剂 |
| CN106669836A (zh) * | 2015-11-05 | 2017-05-17 | 南通市永顺化工有限公司 | 一种用于制备乙撑胺的催化剂 |
| CN106669825A (zh) * | 2015-11-05 | 2017-05-17 | 南通市永顺化工有限公司 | 一种用于制备乙撑胺的催化剂 |
| CN106807395A (zh) * | 2015-11-27 | 2017-06-09 | 中国科学院大连化学物理研究所 | 一种用于合成己二胺的催化剂 |
| CN106807377A (zh) * | 2015-11-27 | 2017-06-09 | 中国科学院大连化学物理研究所 | 一种用于合成己二胺的催化剂 |
| CN105801436A (zh) * | 2016-04-13 | 2016-07-27 | 四川之江高新材料股份有限公司 | N,n,n’-三甲基-n’-羟乙基-乙二胺的合成方法 |
| CN109569631A (zh) * | 2017-09-29 | 2019-04-05 | 中国科学院大连化学物理研究所 | 一种用于己炔二醇加氢制备己二醇的催化剂及制备和应用 |
| CN107913694A (zh) * | 2017-10-31 | 2018-04-17 | 山东玉皇化工有限公司 | 一种胺化催化剂载体的调变方法及其应用 |
| CN109908900B (zh) * | 2017-12-12 | 2022-05-06 | 中国科学院大连化学物理研究所 | 一种负载型催化剂及其制备方法与应用 |
| CN108311159A (zh) * | 2018-04-15 | 2018-07-24 | 陕西理工大学 | 一种用于合成三乙烯四胺的催化剂及其合成方法 |
| CN111018727A (zh) * | 2018-10-10 | 2020-04-17 | 中国石油化工股份有限公司 | 甘氨酸的生产方法 |
| CN110116004B (zh) * | 2019-06-11 | 2022-02-25 | 吉林化工学院 | 一种硝酸盐制备的一乙醇胺和液氨还原胺化合成乙撑胺的催化剂及其制备和使用方法 |
| CN112044447B (zh) * | 2020-08-18 | 2023-02-14 | 西安近代化学研究所 | 一种用于合成一乙胺的催化剂、制备方法及应用 |
| CN114433113B (zh) * | 2020-10-30 | 2023-07-21 | 中国石油化工股份有限公司 | 具有催化醇氨化功能的催化剂和载体及其制备方法和应用 |
| CA3200306A1 (en) | 2020-10-30 | 2022-05-05 | China Petroleum & Chemical Corporation | Amination catalyst and preparation and use thereof |
| US20230381757A1 (en) | 2020-10-30 | 2023-11-30 | China Petroleum & Chemical Corporation | Amination catalyst and preparation and use thereof |
| CN114436993B (zh) * | 2020-11-05 | 2023-10-13 | 中国石油化工股份有限公司 | 制备哌嗪的方法 |
| CN113713853B (zh) * | 2021-09-16 | 2024-03-22 | 中触媒新材料股份有限公司 | 一种环状亚胺制备脂肪二胺的方法及所用催化剂 |
| CN116410156B (zh) * | 2021-12-29 | 2025-05-02 | 中国科学院过程工程研究所 | 一种草酸酯氢氨化制备乙撑胺的方法 |
| CN114605268B (zh) * | 2022-03-22 | 2023-02-28 | 中国科学院大连化学物理研究所 | 一种催化合成多乙烯多胺的方法 |
| CN114713224B (zh) * | 2022-04-02 | 2023-06-23 | 厦门大学 | 一种用于催化乙醇胺化制备乙基胺的催化剂及其制备方法和应用 |
| CN118253311A (zh) * | 2024-04-08 | 2024-06-28 | 卫星化学股份有限公司 | 一种用于乙二胺和哌嗪制备的催化剂及其制备方法和应用 |
| CN119241366A (zh) * | 2024-11-28 | 2025-01-03 | 卫星化学股份有限公司 | 双金属催化剂在乙烯胺合成中的应用以及乙烯胺的合成方法 |
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| CN101875014B (zh) * | 2009-11-17 | 2012-10-03 | 中国科学院大连化学物理研究所 | 一种在临氢条件下一乙醇胺和氨转化为乙二胺的催化剂 |
| CN101704753A (zh) * | 2009-11-17 | 2010-05-12 | 中国科学院大连化学物理研究所 | 以乙醇胺和氨为原料在临氢条件下制备为乙二胺的方法 |
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| US4209424A (en) * | 1977-12-12 | 1980-06-24 | Societe Chimique de la Grande Paroisse, Azote et Products Chimiques | Catalyst for manufacturing amines from alcohols |
| CN101406845A (zh) * | 2008-12-08 | 2009-04-15 | 西安近代化学研究所 | 胺化催化剂及其制备方法 |
| CN101829581A (zh) * | 2010-05-11 | 2010-09-15 | 广西壮族自治区化工研究院 | 用于乙醇胺胺化合成乙二胺的催化剂及其制备方法 |
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| IN2014DN07644A (enrdf_load_stackoverflow) | 2015-05-15 |
| CN102658162A (zh) | 2012-09-12 |
| WO2013152548A1 (zh) | 2013-10-17 |
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