CN102584575A - 通过双回流精制乙酸仲丁酯粗产品的方法和乙酸仲丁酯的制备方法 - Google Patents
通过双回流精制乙酸仲丁酯粗产品的方法和乙酸仲丁酯的制备方法 Download PDFInfo
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- CN102584575A CN102584575A CN2011100234852A CN201110023485A CN102584575A CN 102584575 A CN102584575 A CN 102584575A CN 2011100234852 A CN2011100234852 A CN 2011100234852A CN 201110023485 A CN201110023485 A CN 201110023485A CN 102584575 A CN102584575 A CN 102584575A
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- butyl acetate
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 title claims abstract description 243
- 238000000034 method Methods 0.000 title claims abstract description 90
- 238000002360 preparation method Methods 0.000 title claims abstract description 45
- 238000010992 reflux Methods 0.000 title claims abstract description 30
- 238000007670 refining Methods 0.000 title abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 144
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 238000000926 separation method Methods 0.000 claims abstract description 17
- 239000012535 impurity Substances 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims description 185
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 90
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 45
- 238000010533 azeotropic distillation Methods 0.000 claims description 43
- 241000282326 Felis catus Species 0.000 claims description 39
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 38
- 229930195733 hydrocarbon Natural products 0.000 claims description 31
- 150000002430 hydrocarbons Chemical class 0.000 claims description 31
- 239000012071 phase Substances 0.000 claims description 30
- 239000004215 Carbon black (E152) Substances 0.000 claims description 27
- 150000001336 alkenes Chemical class 0.000 claims description 24
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 17
- 230000009977 dual effect Effects 0.000 claims description 16
- 238000007259 addition reaction Methods 0.000 claims description 12
- 239000011964 heteropoly acid Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 238000001816 cooling Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 15
- 238000002479 acid--base titration Methods 0.000 description 13
- 238000009835 boiling Methods 0.000 description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000007701 flash-distillation Methods 0.000 description 4
- 239000008398 formation water Substances 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000008369 fruit flavor Substances 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PCWZHTGDXLRULT-UHFFFAOYSA-N buta-1,3-dienylbenzene styrene Chemical compound C(=C)C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 PCWZHTGDXLRULT-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
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CN 201110023485 CN102584575B (zh) | 2011-01-17 | 2011-01-17 | 通过双回流精制乙酸仲丁酯粗产品的方法和乙酸仲丁酯的制备方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103980115A (zh) * | 2014-06-03 | 2014-08-13 | 湖南瑞源石化股份有限公司 | 一种以高收率从制备乙酸仲丁酯的反应产物中回收乙酸仲丁酯的方法 |
CN107226771A (zh) * | 2016-03-24 | 2017-10-03 | 中国石油化工股份有限公司 | 含有环己烷和乙酸的物流的分离方法及乙酸环己酯的生产方法及联产环己醇和乙醇的方法 |
CN113717051A (zh) * | 2021-09-16 | 2021-11-30 | 泰兴金江化学工业有限公司 | 一种乙酸丁酯的制备方法 |
CN113880712A (zh) * | 2021-09-16 | 2022-01-04 | 泰兴金江化学工业有限公司 | 一种乙酸乙酯的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2199521C1 (ru) * | 2001-09-10 | 2003-02-27 | Закрытое акционерное общество фирма "Альен" | Способ получения втор-бутилацетата |
CN101007761A (zh) * | 2007-02-02 | 2007-08-01 | 胡先念 | 一种从乙酸与混合c4反应后的混合物中分离乙酸仲丁酯的方法 |
CN101481307A (zh) * | 2009-01-13 | 2009-07-15 | 湖南瑞源石化股份有限公司 | 一种从反应产物中分离出乙酸和乙酸仲丁酯的方法 |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2199521C1 (ru) * | 2001-09-10 | 2003-02-27 | Закрытое акционерное общество фирма "Альен" | Способ получения втор-бутилацетата |
CN101007761A (zh) * | 2007-02-02 | 2007-08-01 | 胡先念 | 一种从乙酸与混合c4反应后的混合物中分离乙酸仲丁酯的方法 |
CN101481307A (zh) * | 2009-01-13 | 2009-07-15 | 湖南瑞源石化股份有限公司 | 一种从反应产物中分离出乙酸和乙酸仲丁酯的方法 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103980115A (zh) * | 2014-06-03 | 2014-08-13 | 湖南瑞源石化股份有限公司 | 一种以高收率从制备乙酸仲丁酯的反应产物中回收乙酸仲丁酯的方法 |
CN107226771A (zh) * | 2016-03-24 | 2017-10-03 | 中国石油化工股份有限公司 | 含有环己烷和乙酸的物流的分离方法及乙酸环己酯的生产方法及联产环己醇和乙醇的方法 |
CN107226771B (zh) * | 2016-03-24 | 2020-08-18 | 中国石油化工股份有限公司 | 含有环己烷和乙酸的物流的分离方法及乙酸环己酯的生产方法及联产环己醇和乙醇的方法 |
CN113717051A (zh) * | 2021-09-16 | 2021-11-30 | 泰兴金江化学工业有限公司 | 一种乙酸丁酯的制备方法 |
CN113880712A (zh) * | 2021-09-16 | 2022-01-04 | 泰兴金江化学工业有限公司 | 一种乙酸乙酯的制备方法 |
CN113717051B (zh) * | 2021-09-16 | 2023-08-04 | 泰兴金江化学工业有限公司 | 一种乙酸丁酯的制备方法 |
CN113880712B (zh) * | 2021-09-16 | 2023-08-04 | 泰兴金江化学工业有限公司 | 一种乙酸乙酯的制备方法 |
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