CN102285867B - 3-己炔-2,5-二醇的合成方法 - Google Patents
3-己炔-2,5-二醇的合成方法 Download PDFInfo
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- CN102285867B CN102285867B CN2011101521178A CN201110152117A CN102285867B CN 102285867 B CN102285867 B CN 102285867B CN 2011101521178 A CN2011101521178 A CN 2011101521178A CN 201110152117 A CN201110152117 A CN 201110152117A CN 102285867 B CN102285867 B CN 102285867B
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- KDOWHHULNTXTNS-UHFFFAOYSA-N hex-3-yne-2,5-diol Chemical compound CC(O)C#CC(C)O KDOWHHULNTXTNS-UHFFFAOYSA-N 0.000 title abstract 4
- 238000001308 synthesis method Methods 0.000 title abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 106
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 239000007864 aqueous solution Substances 0.000 claims abstract description 35
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 23
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 76
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 45
- 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 30
- 238000010189 synthetic method Methods 0.000 claims description 26
- PPNKDDZCLDMRHS-UHFFFAOYSA-N dinitrooxybismuthanyl nitrate Chemical compound [Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PPNKDDZCLDMRHS-UHFFFAOYSA-N 0.000 claims description 24
- 229910052802 copper Inorganic materials 0.000 claims description 17
- 238000001514 detection method Methods 0.000 claims description 17
- 238000001802 infusion Methods 0.000 claims description 17
- 239000011259 mixed solution Substances 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 17
- 238000010792 warming Methods 0.000 claims description 17
- 229910052759 nickel Inorganic materials 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 13
- 229910052797 bismuth Inorganic materials 0.000 claims description 12
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 8
- 229910001981 cobalt nitrate Inorganic materials 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 8
- 238000010298 pulverizing process Methods 0.000 claims description 5
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 20
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000010412 oxide-supported catalyst Substances 0.000 abstract 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 abstract 3
- 239000000047 product Substances 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 238000005815 base catalysis Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- -1 mantoquita Chemical class 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
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CN2011101521178A CN102285867B (zh) | 2011-06-08 | 2011-06-08 | 3-己炔-2,5-二醇的合成方法 |
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CN2011101521178A CN102285867B (zh) | 2011-06-08 | 2011-06-08 | 3-己炔-2,5-二醇的合成方法 |
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CN102285867A CN102285867A (zh) | 2011-12-21 |
CN102285867B true CN102285867B (zh) | 2013-11-27 |
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102633602A (zh) * | 2012-04-26 | 2012-08-15 | 江苏泰特尔化工有限公司 | 一种常压制备3-己炔-2,5-二醇的方法 |
CN102875332B (zh) * | 2012-10-12 | 2014-08-13 | 隆昌天康精细化工有限公司 | 淤浆床低压法合成3-己炔-2,5-二醇的工艺 |
CN105061143B (zh) * | 2015-07-31 | 2017-03-08 | 四川隆桥化工集团有限公司 | 淤浆床酸度控制法合成3‑己炔‑2,5‑二醇的工艺 |
CN113019369B (zh) * | 2021-03-23 | 2023-05-23 | 浙江皇马科技股份有限公司 | 一种铜钴复合氧化物负载型催化剂及其制备方法和应用 |
CN113666802B (zh) * | 2021-08-30 | 2023-09-01 | 四川众邦新材料股份有限公司 | 一种合成和萃取纯化3-己炔-2,5-二醇的方法 |
CN115594566B (zh) * | 2022-09-22 | 2023-12-29 | 山东阳谷华泰化工股份有限公司 | 一种2,5-二甲基-2,5-己二醇的合成方法 |
CN116060001A (zh) * | 2022-12-21 | 2023-05-05 | 四川众邦新材料股份有限公司 | 一种乙炔氛围下低压合成3-己炔-2,5-二醇的方法及催化剂 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3723545A (en) * | 1969-02-07 | 1973-03-27 | Basf Ag | Production of alkynols and alkynediols |
US4002694A (en) * | 1972-04-24 | 1977-01-11 | Gaf Corporation | Ethynylation catalyst and process for producing alkynols |
US4584418A (en) * | 1985-03-15 | 1986-04-22 | E. I. Du Pont De Nemours And Company | Preparation of butynediol |
-
2011
- 2011-06-08 CN CN2011101521178A patent/CN102285867B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3723545A (en) * | 1969-02-07 | 1973-03-27 | Basf Ag | Production of alkynols and alkynediols |
US4002694A (en) * | 1972-04-24 | 1977-01-11 | Gaf Corporation | Ethynylation catalyst and process for producing alkynols |
US4584418A (en) * | 1985-03-15 | 1986-04-22 | E. I. Du Pont De Nemours And Company | Preparation of butynediol |
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Owner name: SICHUAN ZHIJIANG ADVANCED MATERIALS CO., LTD. Free format text: FORMER NAME: SICHUAN ZHIJIANG CHEMICAL NEW MATERIAL CO., LTD. |
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Address after: 629100 Jinqiao New District, Sichuan, Suining Patentee after: SICHUAN ZHIJIANG ADVANCED MATERIALS CO., LTD. Patentee after: Zhejiang University Address before: 629128 No. 1 Jinqiao Industrial Port, Pengxi County, Suining, Sichuan Patentee before: Sichuan Zhijiang Chemical New Material Co., Ltd. Patentee before: Zhejiang University |