CN104961650A - 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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- CN104961650A CN104961650A CN201510471931.4A CN201510471931A CN104961650A CN 104961650 A CN104961650 A CN 104961650A CN 201510471931 A CN201510471931 A CN 201510471931A CN 104961650 A CN104961650 A CN 104961650A
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- CN
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- Prior art keywords
- butanone
- air
- reaction
- reaction solution
- ketazine
- Prior art date
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Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 230000003647 oxidation Effects 0.000 title claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 13
- 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 88
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000007788 liquid Substances 0.000 claims abstract description 39
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims abstract description 24
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 17
- 239000012074 organic phase Substances 0.000 claims description 16
- 239000008346 aqueous phase Substances 0.000 claims description 15
- -1 methane amide Chemical class 0.000 claims description 13
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 12
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 101150003085 Pdcl gene Proteins 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 230000001186 cumulative effect Effects 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 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
- 239000007800 oxidant agent Substances 0.000 abstract description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 4
- 229910021592 Copper(II) chloride Inorganic materials 0.000 abstract 2
- 229910002666 PdCl2 Inorganic materials 0.000 abstract 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract 2
- 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
- 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
- 230000008859 change Effects 0.000 description 3
- 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
- 239000000047 product Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CVTZKFWZDBJAHE-UHFFFAOYSA-N [N].N Chemical class [N].N CVTZKFWZDBJAHE-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001408 amides Chemical class 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
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- 230000006872 improvement Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 230000001590 oxidative effect Effects 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000002760 rocket fuel Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
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CN201510471931.4A CN104961650B (zh) | 2015-08-05 | 2015-08-05 | 一种空气氧化法合成丁酮连氮的方法 |
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CN201510471931.4A CN104961650B (zh) | 2015-08-05 | 2015-08-05 | 一种空气氧化法合成丁酮连氮的方法 |
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CN104961650A true CN104961650A (zh) | 2015-10-07 |
CN104961650B CN104961650B (zh) | 2017-03-22 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5466608A (en) * | 1977-11-02 | 1979-05-29 | Mitsui Toatsu Chem Inc | Preparation of azines |
CN101234996A (zh) * | 2008-02-29 | 2008-08-06 | 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 |
-
2015
- 2015-08-05 CN CN201510471931.4A patent/CN104961650B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5466608A (en) * | 1977-11-02 | 1979-05-29 | Mitsui Toatsu Chem Inc | Preparation of azines |
CN101234996A (zh) * | 2008-02-29 | 2008-08-06 | 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 |
Non-Patent Citations (1)
Title |
---|
HIROMU HAYASHI ET AL.: "NH4Cl-CuCl AS A CATALYST FOR THE SYNTHESIS OF KETAZINE DIRECTLY FROM BENZOPHENONE, AMMONIA AND OXYGEN", 《CHEMISTRY LETTERS》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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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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. |