CN104961650B - 一种空气氧化法合成丁酮连氮的方法 - Google Patents
一种空气氧化法合成丁酮连氮的方法 Download PDFInfo
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- CN104961650B CN104961650B CN201510471931.4A CN201510471931A CN104961650B CN 104961650 B CN104961650 B CN 104961650B CN 201510471931 A CN201510471931 A CN 201510471931A CN 104961650 B CN104961650 B CN 104961650B
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- Prior art keywords
- butanone
- air
- ketazine
- ammonia
- reactant liquor
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- 238000000034 method Methods 0.000 title claims abstract description 39
- 230000003647 oxidation Effects 0.000 title claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 10
- LAWAERKRWYQEEN-FKJILZIQSA-N (e)-n-[(z)-butan-2-ylideneamino]butan-2-imine Chemical compound CC\C(C)=N/N=C(\C)CC LAWAERKRWYQEEN-FKJILZIQSA-N 0.000 title abstract 6
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 82
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000007788 liquid Substances 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 22
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910002666 PdCl2 Inorganic materials 0.000 claims abstract description 13
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims abstract description 11
- 239000007800 oxidant agent Substances 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
- 239000000376 reactant Substances 0.000 claims description 23
- 208000035126 Facies Diseases 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 13
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 230000004044 response Effects 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000001186 cumulative effect Effects 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 abstract description 16
- 238000005265 energy consumption Methods 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- VQSIVLYYQQCXAF-UHFFFAOYSA-N n-(benzhydrylideneamino)-1,1-diphenylmethanimine Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)=NN=C(C=1C=CC=CC=1)C1=CC=CC=C1 VQSIVLYYQQCXAF-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- -1 there are four kinds Chemical compound 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PDNNQADNLPRFPG-UHFFFAOYSA-N N.[O] Chemical compound N.[O] PDNNQADNLPRFPG-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- CVTZKFWZDBJAHE-UHFFFAOYSA-N [N].N Chemical class [N].N CVTZKFWZDBJAHE-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910001902 chlorine oxide Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- YRWWOAFMPXPHEJ-OFBPEYICSA-K sodium L-ascorbic acid 2-phosphate Chemical compound [Na+].[Na+].[Na+].OC[C@H](O)[C@H]1OC(=O)C(OP([O-])([O-])=O)=C1[O-] YRWWOAFMPXPHEJ-OFBPEYICSA-K 0.000 description 1
- 229940048058 sodium ascorbyl phosphate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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CN104961650A CN104961650A (zh) | 2015-10-07 |
CN104961650B true CN104961650B (zh) | 2017-03-22 |
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CN107381523A (zh) * | 2017-09-07 | 2017-11-24 | 盐城顺恒化工有限公司 | 一种硫酸肼的制备方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5466608A (en) * | 1977-11-02 | 1979-05-29 | Mitsui Toatsu Chem Inc | Preparation of azines |
CN101234996B (zh) * | 2008-02-29 | 2012-01-25 | 浙江工业大学 | 一种酮连氮的绿色合成方法 |
CN103044285A (zh) * | 2013-01-17 | 2013-04-17 | 重庆蓝苗生物科技开发有限公司 | 过氧化氢法制备丁酮连氮 |
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Effective date of registration: 20180813 Address after: 233010 409 Wu Wan Road, Yuhui District, Bengbu, Anhui Patentee after: Bengbu Jinshi New Material Co., Ltd. Address before: 230000 Anhui Hefei high tech Zone Innovation Industrial Park two phase J2 District C block 18 floor. Patentee before: Hefei dragon totem Information Technology Co., Ltd. |
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Effective date of registration: 20190520 Address after: 230000 B-1512, west of Ganquan Road, Shushan District, Hefei, Anhui. Patentee after: Anhui Eagle Dragon Industrial Design Co., Ltd. Address before: 233010 409 Wu Wan Road, Yuhui District, Bengbu, Anhui Patentee before: Bengbu Jinshi New Material Co., Ltd. |
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Effective date of registration: 20190605 Address after: 311200 Zidong Village, Heshang Town, Xiaoshan District, Hangzhou City, Zhejiang Province Patentee after: Hangzhou Sangjiefei Technology Co., Ltd. Address before: 230000 B-1512, west of Ganquan Road, Shushan District, Hefei, Anhui. Patentee before: Anhui Eagle Dragon Industrial Design Co., Ltd. |