CN109776314A - 一种肉桂酸酯的制备方法 - Google Patents
一种肉桂酸酯的制备方法 Download PDFInfo
- Publication number
- CN109776314A CN109776314A CN201910094869.XA CN201910094869A CN109776314A CN 109776314 A CN109776314 A CN 109776314A CN 201910094869 A CN201910094869 A CN 201910094869A CN 109776314 A CN109776314 A CN 109776314A
- Authority
- CN
- China
- Prior art keywords
- cinnamate
- preparation
- esterification
- alcohol
- infiltration
- 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.)
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title claims abstract description 68
- 229940114081 cinnamate Drugs 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- 230000008595 infiltration Effects 0.000 claims abstract description 49
- 238000001764 infiltration Methods 0.000 claims abstract description 49
- 230000032050 esterification Effects 0.000 claims abstract description 41
- 238000005886 esterification reaction Methods 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 229930016911 cinnamic acid Natural products 0.000 claims abstract description 39
- 235000013985 cinnamic acid Nutrition 0.000 claims abstract description 39
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000001704 evaporation Methods 0.000 claims abstract description 36
- 230000008020 evaporation Effects 0.000 claims abstract description 36
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims abstract description 35
- 238000000066 reactive distillation Methods 0.000 claims abstract description 17
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 238000010992 reflux Methods 0.000 claims description 34
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 17
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 15
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 15
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 15
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 15
- 239000012528 membrane Substances 0.000 claims description 11
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 claims description 9
- 239000000919 ceramic Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 230000014759 maintenance of location Effects 0.000 claims description 8
- OLLPXZHNCXACMM-CMDGGOBGSA-N Propyl cinnamate Chemical compound CCCOC(=O)\C=C\C1=CC=CC=C1 OLLPXZHNCXACMM-CMDGGOBGSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000001819 propan-2-yl (E)-3-phenylprop-2-enoate Substances 0.000 claims description 7
- RGACABDFLVLVCT-UHFFFAOYSA-N propan-2-yl 3-phenylprop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC=CC=C1 RGACABDFLVLVCT-UHFFFAOYSA-N 0.000 claims description 7
- 239000001572 propyl (E)-3-phenylprop-2-enoate Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 230000008016 vaporization Effects 0.000 claims description 6
- 235000013372 meat Nutrition 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 5
- 235000011007 phosphoric acid Nutrition 0.000 claims description 4
- 238000009834 vaporization Methods 0.000 claims description 4
- 230000035515 penetration Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 150000002148 esters Chemical class 0.000 abstract description 14
- 238000005265 energy consumption Methods 0.000 abstract description 8
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 description 22
- 239000007789 gas Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 238000004064 recycling Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 11
- 239000012466 permeate Substances 0.000 description 11
- 239000012530 fluid Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 230000000149 penetrating effect Effects 0.000 description 9
- 230000036632 reaction speed Effects 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 8
- 238000013461 design Methods 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- -1 Cinnamic acid ester Chemical class 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- 239000001657 2-methylpropyl (E)-3-phenylprop-2-enoate Substances 0.000 description 3
- YIDCITOHTLPMMZ-UHFFFAOYSA-N 5-tert-butyl-1h-pyrazole Chemical compound CC(C)(C)C1=CC=NN1 YIDCITOHTLPMMZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007792 gaseous phase Substances 0.000 description 3
- 239000011964 heteropoly acid Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 2
- QDSSWFSXBZSFQO-UHFFFAOYSA-N 2-amino-6-ethyl-1h-pyrimidin-4-one Chemical compound CCC1=CC(=O)N=C(N)N1 QDSSWFSXBZSFQO-UHFFFAOYSA-N 0.000 description 2
- JFHCDEYLWGVZMX-CMDGGOBGSA-N Isoamyl cinnamate Chemical compound CC(C)CCOC(=O)\C=C\C1=CC=CC=C1 JFHCDEYLWGVZMX-CMDGGOBGSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- MWRJCEDXZKNABM-UHFFFAOYSA-N germanium tungsten Chemical compound [Ge].[W] MWRJCEDXZKNABM-UHFFFAOYSA-N 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QDRJCWZGTMRXCL-ZHACJKMWSA-N pentyl (e)-3-phenylprop-2-enoate Chemical compound CCCCCOC(=O)\C=C\C1=CC=CC=C1 QDRJCWZGTMRXCL-ZHACJKMWSA-N 0.000 description 2
- NFIYTPYOYDDLGO-UHFFFAOYSA-N phosphoric acid;sodium Chemical group [Na].OP(O)(O)=O NFIYTPYOYDDLGO-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- NAORGNSYBDQEPT-UHFFFAOYSA-N 3-phenylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC=C1.OC(=O)C=CC1=CC=CC=C1 NAORGNSYBDQEPT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001405 butyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- OHHIVLJVBNCSHV-KTKRTIGZSA-N butyl cinnamate Chemical compound CCCCOC(=O)\C=C/C1=CC=CC=C1 OHHIVLJVBNCSHV-KTKRTIGZSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VIKVSUVYUVJHOA-UHFFFAOYSA-N octyl 3-phenylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C=CC1=CC=CC=C1 VIKVSUVYUVJHOA-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN109776314A true CN109776314A (zh) | 2019-05-21 |
CN109776314B CN109776314B (zh) | 2021-11-12 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111253236A (zh) * | 2020-03-10 | 2020-06-09 | 宿迁科思化学有限公司 | 一种高品质对位铃兰醛的制备方法 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101289389A (zh) * | 2008-05-30 | 2008-10-22 | 南京工业大学 | 一种乙酸乙酯的生产工艺 |
CN101402568A (zh) * | 2008-11-18 | 2009-04-08 | 南京工业大学 | 反应精馏与渗透汽化耦合生产乙酸乙酯的方法 |
CN201454511U (zh) * | 2009-07-03 | 2010-05-12 | 中国石油天然气股份有限公司 | 一种制备己二酸二甲酯的渗透汽化-反应耦合装置 |
CN102249916A (zh) * | 2011-05-26 | 2011-11-23 | 南京化工职业技术学院 | 柠檬酸三丁酯的连续化生产工艺 |
CN202289520U (zh) * | 2011-10-19 | 2012-07-04 | 华东理工大学 | 一种含有催化与渗透汽化膜组件的精馏耦合过程设备 |
CN103012149A (zh) * | 2012-12-06 | 2013-04-03 | 南昌大学 | 酯化反应-渗透汽化膜分离集成生产3-羟基丙酸甲酯的方法 |
CN203648396U (zh) * | 2013-12-10 | 2014-06-18 | 华东理工大学工程设计研究院有限公司 | 一种用于合成酯类化合物的渗透汽化膜反应装置 |
CN204211671U (zh) * | 2014-09-22 | 2015-03-18 | 江苏九天高科技股份有限公司 | 一种精馏-蒸汽渗透耦合生产马来酸二乙酯的装置 |
CN104926653A (zh) * | 2015-06-11 | 2015-09-23 | 江苏九天高科技股份有限公司 | 一种反应与蒸汽渗透脱水耦合的己酸乙酯合成工艺及装置 |
CN107185265A (zh) * | 2017-06-21 | 2017-09-22 | 武汉智宏思博化工科技有限公司 | 一种精馏塔与渗透气化膜***耦合的有机溶剂脱水设备 |
-
2019
- 2019-01-31 CN CN201910094869.XA patent/CN109776314B/zh active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101289389A (zh) * | 2008-05-30 | 2008-10-22 | 南京工业大学 | 一种乙酸乙酯的生产工艺 |
CN101402568A (zh) * | 2008-11-18 | 2009-04-08 | 南京工业大学 | 反应精馏与渗透汽化耦合生产乙酸乙酯的方法 |
CN201454511U (zh) * | 2009-07-03 | 2010-05-12 | 中国石油天然气股份有限公司 | 一种制备己二酸二甲酯的渗透汽化-反应耦合装置 |
CN102249916A (zh) * | 2011-05-26 | 2011-11-23 | 南京化工职业技术学院 | 柠檬酸三丁酯的连续化生产工艺 |
CN202289520U (zh) * | 2011-10-19 | 2012-07-04 | 华东理工大学 | 一种含有催化与渗透汽化膜组件的精馏耦合过程设备 |
CN103012149A (zh) * | 2012-12-06 | 2013-04-03 | 南昌大学 | 酯化反应-渗透汽化膜分离集成生产3-羟基丙酸甲酯的方法 |
CN203648396U (zh) * | 2013-12-10 | 2014-06-18 | 华东理工大学工程设计研究院有限公司 | 一种用于合成酯类化合物的渗透汽化膜反应装置 |
CN204211671U (zh) * | 2014-09-22 | 2015-03-18 | 江苏九天高科技股份有限公司 | 一种精馏-蒸汽渗透耦合生产马来酸二乙酯的装置 |
CN104926653A (zh) * | 2015-06-11 | 2015-09-23 | 江苏九天高科技股份有限公司 | 一种反应与蒸汽渗透脱水耦合的己酸乙酯合成工艺及装置 |
CN107185265A (zh) * | 2017-06-21 | 2017-09-22 | 武汉智宏思博化工科技有限公司 | 一种精馏塔与渗透气化膜***耦合的有机溶剂脱水设备 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111253236A (zh) * | 2020-03-10 | 2020-06-09 | 宿迁科思化学有限公司 | 一种高品质对位铃兰醛的制备方法 |
CN111253236B (zh) * | 2020-03-10 | 2022-11-18 | 宿迁科思化学有限公司 | 一种高品质对位铃兰醛的制备方法 |
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CN109776314B (zh) | 2021-11-12 |
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