CN108203387A - 一种由羟基乙腈加氢制备一乙醇胺的方法 - Google Patents
一种由羟基乙腈加氢制备一乙醇胺的方法 Download PDFInfo
- Publication number
- CN108203387A CN108203387A CN201810061376.1A CN201810061376A CN108203387A CN 108203387 A CN108203387 A CN 108203387A CN 201810061376 A CN201810061376 A CN 201810061376A CN 108203387 A CN108203387 A CN 108203387A
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- China
- Prior art keywords
- hydroxyacetonitrile
- reaction
- catalyst
- hydrogenation
- monoethanolamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 title claims abstract description 71
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 17
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 235000019441 ethanol Nutrition 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003426 co-catalyst Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052593 corundum Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 abstract description 10
- 239000012752 auxiliary agent Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 9
- 229940043237 diethanolamine Drugs 0.000 description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 238000007599 discharging Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
- 230000002687 intercalation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
Description
时间h | 羟基乙腈ppm | 一乙醇胺% | 二乙醇胺% | 三乙醇胺% | 乙醇酰胺ppm |
5 | 5 | 98.5 | 1.0 | 0.4 | 50 |
10 | 5 | 98.4 | 1.1 | 0.5 | 60 |
15 | 6 | 98.7 | 0.9 | 0.2 | 40 |
20 | 4 | 98.4 | 1.1 | 0.5 | 50 |
25 | 5 | 98.6 | 1.2 | 0.3 | 40 |
30 | 6 | 98.5 | 1.0 | 0.4 | 60 |
35 | 4 | 98.3 | 0.9 | 0.6 | 50 |
40 | 5 | 98.6 | 1.0 | 0.3 | 40 |
45 | 4 | 98.7 | 1.1 | 0.2 | 60 |
50 | 6 | 98.3 | 1.2 | 0.6 | 50 |
时间h | 羟基乙腈ppm | 一乙醇胺% | 二乙醇胺% | 三乙醇胺% | 乙醇酰胺ppm |
5 | 4 | 98.4 | 1.1 | 0.4 | 60 |
10 | 6 | 98.5 | 1.2 | 0.2 | 50 |
15 | 7 | 98.6 | 1 | 0.3 | 50 |
20 | 4 | 98.5 | 1.1 | 0.3 | 40 |
25 | 5 | 98.5 | 0.9 | 0.5 | 50 |
30 | 6 | 98.6 | 1.1 | 0.2 | 50 |
35 | 8 | 98.4 | 1 | 0.4 | 40 |
40 | 3 | 98.7 | 0.9 | 0.3 | 60 |
45 | 5 | 98.6 | 1.1 | 0.2 | 50 |
50 | 6 | 98.4 | 1.1 | 0.4 | 60 |
时间h | 羟基乙腈ppm | 一乙醇胺% | 二乙醇胺% | 三乙醇胺% | 乙醇酰胺ppm |
5 | 5 | 98.3 | 1.2 | 0.4 | 30 |
10 | 5 | 98.7 | 0.9 | 0.3 | 30 |
15 | 6 | 98.4 | 1.2 | 0.3 | 50 |
20 | 4 | 98.7 | 0.9 | 0.3 | 30 |
25 | 5 | 98.5 | 1.2 | 0.2 | 50 |
30 | 6 | 98.8 | 0.8 | 0.3 | 60 |
35 | 4 | 98.3 | 1.3 | 0.3 | 70 |
40 | 5 | 98.3 | 1.4 | 0.2 | 30 |
45 | 4 | 98.9 | 0.8 | 0.2 | 50 |
50 | 6 | 98.3 | 1.2 | 0.4 | 40 |
时间h | 羟基乙腈ppm | 一乙醇胺% | 二乙醇胺% | 三乙醇胺% | 乙醇酰胺ppm |
5 | 4 | 98.1 | 1.4 | 0.4 | 60 |
10 | 4 | 98.3 | 1.0 | 0.6 | 40 |
15 | 5 | 98.6 | 0.8 | 0.5 | 50 |
20 | 6 | 98.3 | 1.1 | 0.5 | 60 |
25 | 4 | 98.7 | 1.0 | 0.2 | 50 |
30 | 5 | 98.5 | 1.0 | 0.4 | 40 |
35 | 6 | 98.4 | 0.9 | 0.6 | 60 |
40 | 4 | 98.5 | 0.9 | 0.5 | 50 |
45 | 6 | 98.6 | 1.0 | 0.3 | 50 |
50 | 5 | 98.2 | 1.1 | 0.6 | 40 |
时间h | 羟基乙腈% | 一乙醇胺% | 二乙醇胺% | 三乙醇胺% | 乙醇酰胺% |
5 | 0.05 | 97.5 | 1.9 | 0.4 | 0.006 |
10 | 0.2 | 94.9 | 3.1 | 1.5 | 0.05 |
15 | 2.5 | 90.7 | 3.9 | 2.2 | 0.4 |
20 | 16.5 | 78 | 3.2 | 1.4 | 0.8 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201810061376.1A CN108203387B (zh) | 2018-01-23 | 2018-01-23 | 一种由羟基乙腈加氢制备一乙醇胺的方法 |
Applications Claiming Priority (1)
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CN201810061376.1A CN108203387B (zh) | 2018-01-23 | 2018-01-23 | 一种由羟基乙腈加氢制备一乙醇胺的方法 |
Publications (2)
Publication Number | Publication Date |
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CN108203387A true CN108203387A (zh) | 2018-06-26 |
CN108203387B CN108203387B (zh) | 2021-01-15 |
Family
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Family Applications (1)
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CN201810061376.1A Active CN108203387B (zh) | 2018-01-23 | 2018-01-23 | 一种由羟基乙腈加氢制备一乙醇胺的方法 |
Country Status (1)
Country | Link |
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CN (1) | CN108203387B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112608244A (zh) * | 2020-12-22 | 2021-04-06 | 山东华鲁恒升化工股份有限公司 | 一种新型制备一乙醇胺的方法 |
CN115193436A (zh) * | 2022-08-22 | 2022-10-18 | 山东明化新材料有限公司 | 一种镍钴金属骨架催化剂、制备方法及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB598984A (en) * | 1944-07-14 | 1948-03-02 | Du Pont | Improvements in and relating to alkanolamines |
US2586325A (en) * | 1947-08-01 | 1952-02-19 | Du Pont | Production of ethanolamine |
CN101434551A (zh) * | 2008-12-13 | 2009-05-20 | 江苏远洋化学有限公司 | 一种一乙醇胺的合成方法 |
-
2018
- 2018-01-23 CN CN201810061376.1A patent/CN108203387B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB598984A (en) * | 1944-07-14 | 1948-03-02 | Du Pont | Improvements in and relating to alkanolamines |
US2586325A (en) * | 1947-08-01 | 1952-02-19 | Du Pont | Production of ethanolamine |
CN101434551A (zh) * | 2008-12-13 | 2009-05-20 | 江苏远洋化学有限公司 | 一种一乙醇胺的合成方法 |
Non-Patent Citations (3)
Title |
---|
MASAHIKO ARAI等: "Selective hydrogenation of benzyl cyanide to 2-phenylethylamine over a Pd/Al2O3 catalyst promoted by synergistic effects of CO2 and water", 《GREEN CHEM.》 * |
MATTHESSEN, ROMAN等: "Decarboxylation of a Wide Range of Amino Acids with Electrogenerated Hypobromite", 《EUR. J. ORG. CHEM.》 * |
REGGIE L. HUDSON等: "Amino Acids from Ion-Irradiated Nitrile-Containing Ices", 《ASTROBIOLOGY》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112608244A (zh) * | 2020-12-22 | 2021-04-06 | 山东华鲁恒升化工股份有限公司 | 一种新型制备一乙醇胺的方法 |
CN112608244B (zh) * | 2020-12-22 | 2022-11-11 | 山东华鲁恒升化工股份有限公司 | 一种新型制备一乙醇胺的方法 |
CN115193436A (zh) * | 2022-08-22 | 2022-10-18 | 山东明化新材料有限公司 | 一种镍钴金属骨架催化剂、制备方法及其应用 |
CN115193436B (zh) * | 2022-08-22 | 2024-01-26 | 山东明化新材料有限公司 | 一种镍钴金属骨架催化剂、制备方法及其应用 |
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