CN101703945B - 耐温季铵型阴离子交换树脂相转移催化剂及其制备方法 - Google Patents
耐温季铵型阴离子交换树脂相转移催化剂及其制备方法 Download PDFInfo
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- CN101703945B CN101703945B CN2009102350738A CN200910235073A CN101703945B CN 101703945 B CN101703945 B CN 101703945B CN 2009102350738 A CN2009102350738 A CN 2009102350738A CN 200910235073 A CN200910235073 A CN 200910235073A CN 101703945 B CN101703945 B CN 101703945B
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- Prior art keywords
- exchange resin
- phase transfer
- quaternary ammonium
- polystyrene
- transfer catalyst
- Prior art date
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- 239000003444 phase transfer catalyst Substances 0.000 title claims abstract description 26
- 239000003957 anion exchange resin Substances 0.000 title claims abstract description 25
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 39
- 239000000460 chlorine Substances 0.000 claims abstract description 39
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 230000008961 swelling Effects 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 125000001309 chloro group Chemical class Cl* 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims description 13
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 230000002152 alkylating effect Effects 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 230000003252 repetitive effect Effects 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000005406 washing Methods 0.000 abstract description 13
- 239000004793 Polystyrene Substances 0.000 abstract description 4
- 229920002223 polystyrene Polymers 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 4
- 235000017168 chlorine Nutrition 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- 241000192041 Micrococcus Species 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 239000011324 bead Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 32
- 229920005989 resin Polymers 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 9
- 238000009835 boiling Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 239000004519 grease Substances 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- WBOHXLDSPBIPTP-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-4-amine Chemical compound CN(C1=CC=NC2=NC=CC=C12)C WBOHXLDSPBIPTP-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- -1 quaternary ammonium salt ion Chemical class 0.000 description 2
- 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 1
- KUWBYWUSERRVQP-UHFFFAOYSA-N 3,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1Cl KUWBYWUSERRVQP-UHFFFAOYSA-N 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VRWJOISQKOAUMR-UHFFFAOYSA-N n,n-dibutylpyridin-4-amine Chemical compound CCCCN(CCCC)C1=CC=NC=C1 VRWJOISQKOAUMR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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CN2009102350738A CN101703945B (zh) | 2009-11-13 | 2009-11-13 | 耐温季铵型阴离子交换树脂相转移催化剂及其制备方法 |
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CN2009102350738A CN101703945B (zh) | 2009-11-13 | 2009-11-13 | 耐温季铵型阴离子交换树脂相转移催化剂及其制备方法 |
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CN101703945A CN101703945A (zh) | 2010-05-12 |
CN101703945B true CN101703945B (zh) | 2011-07-27 |
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CN102500430B (zh) * | 2011-10-19 | 2013-07-24 | 厦门大学 | 一种双长碳链改性阴离子交换树脂及其制备方法与应用 |
CN103008007B (zh) * | 2012-12-10 | 2014-11-05 | 厦门大学 | 合成丙二醇醚的树脂型固体碱催化剂及制备方法和应用 |
CN109365009B (zh) * | 2018-11-20 | 2021-04-27 | 杭州多能环保科技有限公司 | 一种用于环丁砜净化的离子交换树脂的制备方法 |
CN112452308B (zh) * | 2020-12-09 | 2022-10-25 | 昆明理工大学 | 一种含吡啶酰胺的吸附聚合物的合成方法及应用 |
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Effective date of registration: 20141203 Address after: 213311 Jiangsu city of Changzhou Province town street Yang Di drift tau 8-2 No. 7 Patentee after: Liyang Chang Technology Transfer Center Co., Ltd. Address before: Gehu Lake Road Wujin District 213164 Jiangsu city of Changzhou province No. 1 Patentee before: Jiangsu Polytechnic University |
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Effective date of registration: 20200107 Address after: 213164 Jiangsu province Changzhou city Hutang District Wujin town Gehu Lake Road No. 21 Patentee after: Changzhou University Address before: 213311 Jiangsu city of Changzhou Province town street Yang Di drift tau 8-2 No. 7 Patentee before: Liyang Chang Technology Transfer Center Co., Ltd. |
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