CN104262168A - 一种己二胺的制备方法 - Google Patents
一种己二胺的制备方法 Download PDFInfo
- Publication number
- CN104262168A CN104262168A CN201410488395.4A CN201410488395A CN104262168A CN 104262168 A CN104262168 A CN 104262168A CN 201410488395 A CN201410488395 A CN 201410488395A CN 104262168 A CN104262168 A CN 104262168A
- Authority
- CN
- China
- Prior art keywords
- preparation
- periodate
- quaternary ammonium
- reaction
- hexanedial
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims description 33
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 24
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-UHFFFAOYSA-N 0.000 claims description 19
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 15
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 14
- 229960001866 silicon dioxide Drugs 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000007865 diluting Methods 0.000 claims description 12
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical group [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 12
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000013019 agitation Methods 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- JRRNETAQGVDLRW-UHFFFAOYSA-N 1-hexadecyl-3-methyl-2h-imidazole Chemical compound CCCCCCCCCCCCCCCCN1CN(C)C=C1 JRRNETAQGVDLRW-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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 4
- 238000004176 ammonification Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- -1 gac Substances 0.000 claims description 4
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004904 shortening Methods 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- IUNCEDRRUNZACO-UHFFFAOYSA-N butyl(trimethyl)azanium Chemical compound CCCC[N+](C)(C)C IUNCEDRRUNZACO-UHFFFAOYSA-N 0.000 claims description 3
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000006230 acetylene black Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims description 2
- 150000002815 nickel Chemical class 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- HTKPDYSCAPSXIR-UHFFFAOYSA-N octyltrimethylammonium ion Chemical compound CCCCCCCC[N+](C)(C)C HTKPDYSCAPSXIR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 10
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 239000002699 waste material Substances 0.000 abstract description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 13
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- FSSKHQLGSNCPOG-UHFFFAOYSA-N [Br].C(CCCCCCCCCCCCCCC)N1CN(C=C1)C Chemical compound [Br].C(CCCCCCCCCCCCCCC)N1CN(C=C1)C FSSKHQLGSNCPOG-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000002440 industrial waste Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410488395.4A CN104262168B (zh) | 2014-09-22 | 2014-09-22 | 一种己二胺的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410488395.4A CN104262168B (zh) | 2014-09-22 | 2014-09-22 | 一种己二胺的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104262168A true CN104262168A (zh) | 2015-01-07 |
CN104262168B CN104262168B (zh) | 2017-03-15 |
Family
ID=52153788
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410488395.4A Active CN104262168B (zh) | 2014-09-22 | 2014-09-22 | 一种己二胺的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104262168B (zh) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108993589A (zh) * | 2018-07-09 | 2018-12-14 | 湖南师范大学 | 一种高品质四甲基十聚钨酸季铵盐的制备方法 |
CN111056955A (zh) * | 2019-12-16 | 2020-04-24 | 中国科学院大连化学物理研究所 | 一种环己烯制备己二胺的方法 |
CN111056948A (zh) * | 2019-12-16 | 2020-04-24 | 中国科学院大连化学物理研究所 | 制备己二胺的方法 |
CN111072488A (zh) * | 2019-12-16 | 2020-04-28 | 中国科学院大连化学物理研究所 | 一种基于环己烯的己二胺制备工艺 |
CN111072487A (zh) * | 2019-12-16 | 2020-04-28 | 中国科学院大连化学物理研究所 | 基于环己烯的制备己二胺的方法 |
CN111085247A (zh) * | 2019-12-16 | 2020-05-01 | 中国科学院大连化学物理研究所 | 一种碱性分子筛负载的催化剂及其制备方法与应用 |
CN111116376A (zh) * | 2019-12-16 | 2020-05-08 | 中国科学院大连化学物理研究所 | 一种己二胺的制备工艺 |
CN111116377A (zh) * | 2019-12-16 | 2020-05-08 | 中国科学院大连化学物理研究所 | 一种制备己二胺的方法 |
CN111151256A (zh) * | 2020-01-20 | 2020-05-15 | 山东玉皇化工有限公司 | 一种用于合成己二胺的催化剂 |
CN112300008A (zh) * | 2020-10-30 | 2021-02-02 | 宿迁联盛科技股份有限公司 | 一种1,6-己二胺的合成方法 |
CN112939784A (zh) * | 2021-02-04 | 2021-06-11 | 山西铁峰化工有限公司 | 一种己二胺的工业制备方法 |
CN114425347A (zh) * | 2020-10-29 | 2022-05-03 | 中国石油化工股份有限公司 | 选择性氨化加氢催化剂及其制备方法和环己亚胺的合成方法 |
CN115368224A (zh) * | 2022-08-10 | 2022-11-22 | 北京化工大学 | 一种由丁二烯制备己二胺的***装置和方法 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5475141A (en) * | 1993-06-07 | 1995-12-12 | Chemie Linz Gmbh | Process for preparing primary amines from aldehydes |
CN1200370A (zh) * | 1997-05-14 | 1998-12-02 | 可乐丽股份有限公司 | 二胺的制备方法 |
CN1446793A (zh) * | 2002-03-27 | 2003-10-08 | 可乐丽股份有限公司 | 二胺的制造方法 |
CN1939890A (zh) * | 2006-09-27 | 2007-04-04 | 浙江工业大学 | 一种仲胺类化合物的制备方法 |
CN101489979A (zh) * | 2006-07-14 | 2009-07-22 | 巴斯夫欧洲公司 | 生产胺的方法 |
CN102614920A (zh) * | 2012-03-19 | 2012-08-01 | 北京旭阳化工技术研究院有限公司 | 二氧化硅或聚苯乙烯树脂固载化十聚钨酸盐催化剂及其催化氧化环己烯合成己二酸的方法 |
CN102781571A (zh) * | 2009-12-03 | 2012-11-14 | 巴斯夫欧洲公司 | 用于制备胺的催化剂和方法 |
CN103265405A (zh) * | 2013-05-15 | 2013-08-28 | 北京旭阳化工技术研究院有限公司 | 采用相转移催化剂催化氧化环己烯制备1,2-环己二醇的方法 |
-
2014
- 2014-09-22 CN CN201410488395.4A patent/CN104262168B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5475141A (en) * | 1993-06-07 | 1995-12-12 | Chemie Linz Gmbh | Process for preparing primary amines from aldehydes |
CN1200370A (zh) * | 1997-05-14 | 1998-12-02 | 可乐丽股份有限公司 | 二胺的制备方法 |
CN1446793A (zh) * | 2002-03-27 | 2003-10-08 | 可乐丽股份有限公司 | 二胺的制造方法 |
CN101489979A (zh) * | 2006-07-14 | 2009-07-22 | 巴斯夫欧洲公司 | 生产胺的方法 |
CN1939890A (zh) * | 2006-09-27 | 2007-04-04 | 浙江工业大学 | 一种仲胺类化合物的制备方法 |
CN102781571A (zh) * | 2009-12-03 | 2012-11-14 | 巴斯夫欧洲公司 | 用于制备胺的催化剂和方法 |
CN102614920A (zh) * | 2012-03-19 | 2012-08-01 | 北京旭阳化工技术研究院有限公司 | 二氧化硅或聚苯乙烯树脂固载化十聚钨酸盐催化剂及其催化氧化环己烯合成己二酸的方法 |
CN103265405A (zh) * | 2013-05-15 | 2013-08-28 | 北京旭阳化工技术研究院有限公司 | 采用相转移催化剂催化氧化环己烯制备1,2-环己二醇的方法 |
Non-Patent Citations (4)
Title |
---|
张永江等: "加氢脱硫催化剂活性影响因素的研究进展", 《精细石油化工进展》 * |
徐亚琳: ""高水热稳定Ni/γ-Al2O3催化剂的制备及丁炔二醇加氢研究"", 《山西大学硕士学位论文》 * |
武晓剑等: "1,6-己二醛合成工艺研究", 《香料香精化妆品》 * |
马世昌: "《化工物质词典》", 30 April 1999 * |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108993589A (zh) * | 2018-07-09 | 2018-12-14 | 湖南师范大学 | 一种高品质四甲基十聚钨酸季铵盐的制备方法 |
CN111056955B (zh) * | 2019-12-16 | 2021-05-25 | 中国科学院大连化学物理研究所 | 一种环己烯制备己二胺的方法 |
CN111056955A (zh) * | 2019-12-16 | 2020-04-24 | 中国科学院大连化学物理研究所 | 一种环己烯制备己二胺的方法 |
CN111056948A (zh) * | 2019-12-16 | 2020-04-24 | 中国科学院大连化学物理研究所 | 制备己二胺的方法 |
CN111072488A (zh) * | 2019-12-16 | 2020-04-28 | 中国科学院大连化学物理研究所 | 一种基于环己烯的己二胺制备工艺 |
CN111072487A (zh) * | 2019-12-16 | 2020-04-28 | 中国科学院大连化学物理研究所 | 基于环己烯的制备己二胺的方法 |
CN111085247A (zh) * | 2019-12-16 | 2020-05-01 | 中国科学院大连化学物理研究所 | 一种碱性分子筛负载的催化剂及其制备方法与应用 |
CN111116376A (zh) * | 2019-12-16 | 2020-05-08 | 中国科学院大连化学物理研究所 | 一种己二胺的制备工艺 |
CN111116377A (zh) * | 2019-12-16 | 2020-05-08 | 中国科学院大连化学物理研究所 | 一种制备己二胺的方法 |
CN111151256A (zh) * | 2020-01-20 | 2020-05-15 | 山东玉皇化工有限公司 | 一种用于合成己二胺的催化剂 |
CN111151256B (zh) * | 2020-01-20 | 2023-03-24 | 山东玉皇化工有限公司 | 一种用于合成己二胺的催化剂 |
CN114425347A (zh) * | 2020-10-29 | 2022-05-03 | 中国石油化工股份有限公司 | 选择性氨化加氢催化剂及其制备方法和环己亚胺的合成方法 |
CN114425347B (zh) * | 2020-10-29 | 2023-08-08 | 中国石油化工股份有限公司 | 环己亚胺的合成方法 |
CN112300008A (zh) * | 2020-10-30 | 2021-02-02 | 宿迁联盛科技股份有限公司 | 一种1,6-己二胺的合成方法 |
CN112300008B (zh) * | 2020-10-30 | 2022-04-01 | 宿迁联盛科技股份有限公司 | 一种1,6-己二胺的合成方法 |
CN112939784A (zh) * | 2021-02-04 | 2021-06-11 | 山西铁峰化工有限公司 | 一种己二胺的工业制备方法 |
CN115368224A (zh) * | 2022-08-10 | 2022-11-22 | 北京化工大学 | 一种由丁二烯制备己二胺的***装置和方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104262168B (zh) | 2017-03-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104262168A (zh) | 一种己二胺的制备方法 | |
CN106554286B (zh) | 一种贵金属催化剂连续制备对苯二胺类防老剂的方法 | |
CN103265405B (zh) | 采用相转移催化剂催化氧化环己烯制备1,2-环己二醇的方法 | |
CN103880779B (zh) | 一种杂多酸季铵盐催化烯烃环氧化的方法 | |
CN100594210C (zh) | 从硝基苯催化加氢合成对氨基苯酚的工艺 | |
CN103962150B (zh) | 一种用于制备氯代芳香胺的催化剂及其制备方法 | |
CN100431704C (zh) | 壳聚糖磁微球金属钯配合物催化剂的制备方法 | |
CN104628597A (zh) | 一种制备乙醛肟的方法 | |
CN105032428A (zh) | 一种微波加热合成催化剂的制备方法及基于该制备方法制得催化剂一步法合成环己胺的方法 | |
CN101381315A (zh) | 一种制备对氨基二苯胺的方法 | |
CN102584624A (zh) | 环己酮氨肟化制备环己酮肟的方法 | |
CN103521256A (zh) | 一种用于催化甘油脱水制备丙烯醛的分子筛催化剂及其制备方法 | |
CN104971740A (zh) | 连续制备n-异丙基-4-氟苯胺的催化剂及制备方法和应用 | |
CN104557422A (zh) | 甲苯甲醇侧链烷基化方法 | |
Ghosh et al. | Hybrid cobalt doped-cerium oxide as a multifunctional nanocatalyst for various organic transformations | |
CN111943866A (zh) | 一种采用固定床连续生产乙醛肟的方法 | |
CN104447353B (zh) | 一种苯与羟胺盐反应直接制备苯胺的方法 | |
CN104418752A (zh) | 一种在微反应器中催化硝化合成单硝基邻二甲苯的方法 | |
CN104525240A (zh) | 硝酸铁作为催化剂在苯与羟胺盐反应一步法制苯胺反应中的应用方法 | |
CN103041834B (zh) | 甲基叔戊基醚裂解制备异戊烯的催化剂及制备方法与应用 | |
CN103450010B (zh) | 一种制备环己基甲酸的方法 | |
CN105618143A (zh) | 一种七元氮杂镁金属催化剂及其制备方法和应用 | |
CN107628957A (zh) | 一种环己烯直接氨化合成环己胺的新方法研究 | |
CN109748817B (zh) | 一种由脂肪醛合成脂肪腈的方法 | |
CN104311404A (zh) | 一种肉桂醛的生产方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information |
Address after: 100070 Beijing city Fengtai District Haiying Road No. 6 Building No. 6 hospital Applicant after: BEIJING RISUN TECHNOLOGY CO., LTD. Address before: 100070 Beijing city Fengtai District Haiying Road No. 6 Building No. 6 hospital Applicant before: Beijing Xuyang Chemical Technology Research Institute Co., Ltd. |
|
CB03 | Change of inventor or designer information |
Inventor after: Zhang Yingwei Inventor after: Su Sizheng Inventor after: Zhang Minsheng Inventor after: Cao Yalin Inventor after: Cui Bingbing Inventor before: Zhang Yingwei Inventor before: Zhang Xinzhi Inventor before: Wei Xiaolin Inventor before: Yin Wenya Inventor before: Pang Weiwei Inventor before: Xu Chen Inventor before: Zhou Jun |
|
COR | Change of bibliographic data | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CB03 | Change of inventor or designer information |
Inventor after: Zhang Yingwei Inventor after: Zhang Xinzhi Inventor after: Wei Xiaolin Inventor after: Yin Wenya Inventor after: Pang Weiwei Inventor after: Xu Chen Inventor after: Zhou Jun Inventor after: Cui Bingbing Inventor before: Zhang Yingwei Inventor before: Su Sizheng Inventor before: Zhang Minsheng Inventor before: Cao Yalin Inventor before: Cui Bingbing |
|
CB03 | Change of inventor or designer information | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180525 Address after: 061113 west side of Xu Yang Street, north of Bohai Road, Bohai New District, Hebei Patentee after: Cangzhou Xu Yang science and Technology Co., Ltd. Address before: 100070 Building No. 6, No. 6, Haiying Road, Fengtai District, Beijing Patentee before: BEIJING RISUN TECHNOLOGY CO., LTD. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190513 Address after: 100070 301, 3 floor, 21 building, 188 District, South Fourth Ring Road, Fengtai District, Beijing. Patentee after: BEIJING RISUN TECHNOLOGY CO., LTD. Address before: 061113 west side of Xu Yang Street, north of Bohai Road, Bohai New District, Hebei Patentee before: Cangzhou Xu Yang science and Technology Co., Ltd. |
|
TR01 | Transfer of patent right |