CN1907955A - 丙烯腈装置副产氢氰酸工业规模制备苯胺基乙酸钾的方法 - Google Patents
丙烯腈装置副产氢氰酸工业规模制备苯胺基乙酸钾的方法 Download PDFInfo
- Publication number
- CN1907955A CN1907955A CN 200610048134 CN200610048134A CN1907955A CN 1907955 A CN1907955 A CN 1907955A CN 200610048134 CN200610048134 CN 200610048134 CN 200610048134 A CN200610048134 A CN 200610048134A CN 1907955 A CN1907955 A CN 1907955A
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- CN
- China
- Prior art keywords
- hydrocyanic acid
- aniline
- potassium
- formaldehyde
- potassium hydroxide
- 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
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 title claims abstract description 219
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000006227 byproduct Substances 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 23
- JINONCVJYBHUCP-UHFFFAOYSA-M potassium;2-anilinoacetate Chemical compound [K+].[O-]C(=O)CNC1=CC=CC=C1 JINONCVJYBHUCP-UHFFFAOYSA-M 0.000 title claims abstract description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 183
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 152
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 148
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 30
- KAXCEFLQAYFJKV-UHFFFAOYSA-N 2-anilinoacetonitrile Chemical compound N#CCNC1=CC=CC=C1 KAXCEFLQAYFJKV-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000047 product Substances 0.000 claims abstract description 28
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 4
- CZNJCUMJHDYOHK-UHFFFAOYSA-N 2-anilinoacetic acid;potassium Chemical compound [K].OC(=O)CNC1=CC=CC=C1 CZNJCUMJHDYOHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 23
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- -1 low production cost Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002351 wastewater Substances 0.000 abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 230000035484 reaction time Effects 0.000 abstract 2
- XERIOACPRZDXLY-UHFFFAOYSA-N N(C1=CC=CC=C1)C(C#N)=C.[K] Chemical compound N(C1=CC=CC=C1)C(C#N)=C.[K] XERIOACPRZDXLY-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 description 25
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 7
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 5
- 229940097275 indigo Drugs 0.000 description 5
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 239000011790 ferrous sulphate Substances 0.000 description 2
- 235000003891 ferrous sulphate Nutrition 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BJKZXRGDVGYJTP-UHFFFAOYSA-N anilino acetate Chemical compound CC(=O)ONC1=CC=CC=C1 BJKZXRGDVGYJTP-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 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
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- GZWNUORNEQHOAW-UHFFFAOYSA-M potassium;2-aminoacetate Chemical compound [K+].NCC([O-])=O GZWNUORNEQHOAW-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CNB2006100481346A CN100467442C (zh) | 2006-08-09 | 2006-08-09 | 丙烯腈装置副产氢氰酸工业规模制备苯胺基乙酸钾的方法 |
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CNB2006100481346A CN100467442C (zh) | 2006-08-09 | 2006-08-09 | 丙烯腈装置副产氢氰酸工业规模制备苯胺基乙酸钾的方法 |
Publications (2)
Publication Number | Publication Date |
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CN1907955A true CN1907955A (zh) | 2007-02-07 |
CN100467442C CN100467442C (zh) | 2009-03-11 |
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CNB2006100481346A Expired - Fee Related CN100467442C (zh) | 2006-08-09 | 2006-08-09 | 丙烯腈装置副产氢氰酸工业规模制备苯胺基乙酸钾的方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102115271A (zh) * | 2009-12-30 | 2011-07-06 | 川化股份有限公司 | 一种高浓度含氰或腈有机废水的处理方法 |
CN108794346A (zh) * | 2017-05-05 | 2018-11-13 | 抚顺顺特化工有限公司 | 羟基乙腈的工业制备方法 |
CN113694838A (zh) * | 2021-09-02 | 2021-11-26 | 上海蓝科石化环保科技股份有限公司 | 一种液相氢氰酸连续法生产羟基乙腈的装置和工艺 |
CN114957028A (zh) * | 2022-05-26 | 2022-08-30 | 上海东庚化工技术有限公司 | 一种苯胺基乙酸盐的快速合成方法 |
-
2006
- 2006-08-09 CN CNB2006100481346A patent/CN100467442C/zh not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102115271A (zh) * | 2009-12-30 | 2011-07-06 | 川化股份有限公司 | 一种高浓度含氰或腈有机废水的处理方法 |
CN108794346A (zh) * | 2017-05-05 | 2018-11-13 | 抚顺顺特化工有限公司 | 羟基乙腈的工业制备方法 |
CN113694838A (zh) * | 2021-09-02 | 2021-11-26 | 上海蓝科石化环保科技股份有限公司 | 一种液相氢氰酸连续法生产羟基乙腈的装置和工艺 |
CN113694838B (zh) * | 2021-09-02 | 2023-09-01 | 上海蓝科石化环保科技股份有限公司 | 一种液相氢氰酸连续法生产羟基乙腈的装置和工艺 |
CN114957028A (zh) * | 2022-05-26 | 2022-08-30 | 上海东庚化工技术有限公司 | 一种苯胺基乙酸盐的快速合成方法 |
CN114957028B (zh) * | 2022-05-26 | 2024-01-02 | 上海东庚化工技术有限公司 | 一种苯胺基乙酸盐的快速合成方法 |
Also Published As
Publication number | Publication date |
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CN100467442C (zh) | 2009-03-11 |
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Owner name: ZIBO WANCHANG SCIENCE AND TECHNOLOGY CO., LTD. Free format text: FORMER NAME: ZIBO WANCHANG SCIENCE AND TECHNOLOGY DEVELOPMENT CO., LTD. |
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CP01 | Change in the name or title of a patent holder |
Address after: 255068 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee after: ZIBO WANCHANG SCIENCE & TECHNOLOGY Co.,Ltd. Address before: 255068 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee before: ZIBO WANCHANG TECHNOLOGY DEVELOPMENT Co.,Ltd. |
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C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 255068 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee after: SHANDONG SINOBIOWAY BIOMEDICINE Co.,Ltd. Address before: 255068 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee before: ZIBO WANCHANG SCIENCE & TECHNOLOGY Co.,Ltd. |
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C41 | Transfer of patent application or patent right or utility model | ||
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Effective date of registration: 20170215 Address after: 255000 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee after: Shandong Weiming Tianyuan Biotechnology Co.,Ltd. Address before: 255068 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee before: SHANDONG SINOBIOWAY BIOMEDICINE Co.,Ltd. |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20201127 Address after: No.1, Xinlian Street East, coastal industrial base, Xisheng District, Yingkou City, Liaoning Province, 115000 Patentee after: YINGKOU YINGXIN CHEMICAL TECHNOLOGY Co.,Ltd. Address before: 255000 Chaoyang Road, Zhangdian District, Shandong, Zibo, China Patentee before: Shandong Weiming Tianyuan Biotechnology Co.,Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
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Granted publication date: 20090311 |