CN102476978A - 一种新型乙炔合成炔醇类化合物方法 - Google Patents
一种新型乙炔合成炔醇类化合物方法 Download PDFInfo
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- CN102476978A CN102476978A CN2010105562007A CN201010556200A CN102476978A CN 102476978 A CN102476978 A CN 102476978A CN 2010105562007 A CN2010105562007 A CN 2010105562007A CN 201010556200 A CN201010556200 A CN 201010556200A CN 102476978 A CN102476978 A CN 102476978A
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- water
- ketone
- reaction
- organic phase
- acetylene
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- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 title claims abstract description 19
- 238000010189 synthetic method Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000012074 organic phase Substances 0.000 claims abstract description 29
- 150000002576 ketones Chemical class 0.000 claims abstract description 28
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000012071 phase Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 111
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 235000019270 ammonium chloride Nutrition 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 238000006555 catalytic reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- SVTBMSDMJJWYQN-RXMQYKEDSA-N (4r)-2-methylpentane-2,4-diol Chemical group C[C@@H](O)CC(C)(C)O SVTBMSDMJJWYQN-RXMQYKEDSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 230000000116 mitigating effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- -1 viscosity depressant Substances 0.000 description 2
- 0 *C(*)(C#CC(*)(*)O)N Chemical compound *C(*)(C#CC(*)(*)O)N 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- MEOMYWBRBMUTFW-UHFFFAOYSA-N 6,6-dimethylheptan-2-one Chemical compound CC(=O)CCCC(C)(C)C MEOMYWBRBMUTFW-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000010894 Artemisia argyi Nutrition 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 244000030166 artemisia Species 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N methyl alpha-methylvinyl ketone Natural products CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- PRWVAPJXQCMOFT-UHFFFAOYSA-M potassium;azane;hydroxide Chemical compound N.[OH-].[K+] PRWVAPJXQCMOFT-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002557 soporific effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
重复次数 | 1 | 2 | 3 | 4 |
催化结果 | 85% | 83% | 84% | 82% |
Claims (7)
Priority Applications (1)
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CN201010556200.7A CN102476978B (zh) | 2010-11-24 | 2010-11-24 | 一种乙炔合成炔醇类化合物方法 |
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CN201010556200.7A CN102476978B (zh) | 2010-11-24 | 2010-11-24 | 一种乙炔合成炔醇类化合物方法 |
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CN102476978A true CN102476978A (zh) | 2012-05-30 |
CN102476978B CN102476978B (zh) | 2015-04-08 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102964216A (zh) * | 2012-12-06 | 2013-03-13 | 盘锦科隆精细化工有限公司 | 一种合成癸炔二醇的工艺 |
CN107963960A (zh) * | 2017-12-18 | 2018-04-27 | 王建华 | 一种合成炔二醇的新工艺 |
CN110511113A (zh) * | 2019-08-16 | 2019-11-29 | 袁玮 | 间歇法联产炔醇及烷醇和副产无机盐的工艺 |
CN113698274A (zh) * | 2021-09-27 | 2021-11-26 | 四川众邦制药有限公司 | 一种高收率合成3-丁炔-2-醇的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB580921A (en) * | 1941-04-18 | 1946-09-25 | Charles Weizmann | Improvements in the synthesis of secondary and tertiary ethinyl-carbinols |
US4960959A (en) * | 1987-04-04 | 1990-10-02 | Huels Aktiengesellschaft | Process for the manufacture of alkynediols by reaction of ketones with acetylene |
RU2199519C2 (ru) * | 2001-02-22 | 2003-02-27 | Щелкунов Сергей Анатольевич | СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ α-АЦЕТИЛЕНОВЫХ ДИОЛОВ |
CN1675152A (zh) * | 2002-08-16 | 2005-09-28 | 帝斯曼知识产权资产管理有限公司 | 炔化方法 |
-
2010
- 2010-11-24 CN CN201010556200.7A patent/CN102476978B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB580921A (en) * | 1941-04-18 | 1946-09-25 | Charles Weizmann | Improvements in the synthesis of secondary and tertiary ethinyl-carbinols |
US4960959A (en) * | 1987-04-04 | 1990-10-02 | Huels Aktiengesellschaft | Process for the manufacture of alkynediols by reaction of ketones with acetylene |
RU2199519C2 (ru) * | 2001-02-22 | 2003-02-27 | Щелкунов Сергей Анатольевич | СПОСОБ ПОЛУЧЕНИЯ ТРЕТИЧНЫХ α-АЦЕТИЛЕНОВЫХ ДИОЛОВ |
CN1675152A (zh) * | 2002-08-16 | 2005-09-28 | 帝斯曼知识产权资产管理有限公司 | 炔化方法 |
Non-Patent Citations (2)
Title |
---|
NORMA SHACHAT AND JAMES J. BAGNELL: "Catalytic Ethynylation of Ketones", 《J. ORG. CHEM.》 * |
刘恒军: "片状氢氧化钾生产中废碱的回收工艺", 《氯碱工业》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102964216A (zh) * | 2012-12-06 | 2013-03-13 | 盘锦科隆精细化工有限公司 | 一种合成癸炔二醇的工艺 |
CN107963960A (zh) * | 2017-12-18 | 2018-04-27 | 王建华 | 一种合成炔二醇的新工艺 |
CN110511113A (zh) * | 2019-08-16 | 2019-11-29 | 袁玮 | 间歇法联产炔醇及烷醇和副产无机盐的工艺 |
CN113698274A (zh) * | 2021-09-27 | 2021-11-26 | 四川众邦制药有限公司 | 一种高收率合成3-丁炔-2-醇的方法 |
CN113698274B (zh) * | 2021-09-27 | 2024-04-12 | 四川众邦新材料股份有限公司 | 一种高收率合成3-丁炔-2-醇的方法 |
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CN102476978B (zh) | 2015-04-08 |
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Effective date of registration: 20150326 Address after: 414002 Lingang New District, Yueyang, Hunan, Chenglingji Patentee after: Yueyang Kaimen water additives Co. Ltd. Address before: 430000 49-6-11 village, Wuchang District, Wuhan, Hubei, Nanyuan Patentee before: Yang Chaohui |
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