CN106117137A - 一种利用微反应装置连续制备防老剂rd单体的方法 - Google Patents
一种利用微反应装置连续制备防老剂rd单体的方法 Download PDFInfo
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- CN106117137A CN106117137A CN201610495393.7A CN201610495393A CN106117137A CN 106117137 A CN106117137 A CN 106117137A CN 201610495393 A CN201610495393 A CN 201610495393A CN 106117137 A CN106117137 A CN 106117137A
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- micro
- acetone
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- aniline
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 24
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- 239000003963 antioxidant agent Substances 0.000 title abstract description 5
- 230000003078 antioxidant effect Effects 0.000 title abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 78
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 239000000376 reactant Substances 0.000 claims abstract description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 12
- 230000003712 anti-aging effect Effects 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910015900 BF3 Inorganic materials 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000010924 continuous production Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 239000007788 liquid Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000357 carcinogen Toxicity 0.000 description 2
- 239000003183 carcinogenic agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
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- 230000018044 dehydration Effects 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- -1 ketone amines Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FEQIKDBPUQIQKY-UHFFFAOYSA-N n-phenyl-n-propan-2-ylaniline Chemical compound C=1C=CC=CC=1N(C(C)C)C1=CC=CC=C1 FEQIKDBPUQIQKY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
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CN201610495393.7A CN106117137A (zh) | 2016-06-29 | 2016-06-29 | 一种利用微反应装置连续制备防老剂rd单体的方法 |
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CN201610495393.7A CN106117137A (zh) | 2016-06-29 | 2016-06-29 | 一种利用微反应装置连续制备防老剂rd单体的方法 |
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CN201610495393.7A Pending CN106117137A (zh) | 2016-06-29 | 2016-06-29 | 一种利用微反应装置连续制备防老剂rd单体的方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106831564A (zh) * | 2016-12-21 | 2017-06-13 | 山东斯递尔化工科技有限公司 | 一种利用微反应装置连续制备抗氧剂224的方法 |
CN106831515A (zh) * | 2017-01-13 | 2017-06-13 | 山东斯递尔化工科技有限公司 | 利用微反应装置连续制备二硫化四苄基秋兰姆的方法 |
CN106995396A (zh) * | 2017-03-30 | 2017-08-01 | 山东斯递尔化工科技有限公司 | 一种利用微反应装置连续制备二甲基二硫代氨基甲酸钠的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101274996A (zh) * | 2007-03-30 | 2008-10-01 | 住友橡胶工业株式会社 | 利用了微生物的防老剂、硫化促进剂或改性天然橡胶的制备方法 |
US20090306431A1 (en) * | 2008-06-10 | 2009-12-10 | Keitaro Fujikura | Process for producing antiaging agent, vulcanization accelerator or modified natural rubber by means of microorganism or plant |
CN202139185U (zh) * | 2011-07-11 | 2012-02-08 | 山东曹县斯递尔化工科技有限公司 | 一种用于生产橡胶防老剂rd缩聚反应的装置 |
CN103694169A (zh) * | 2012-09-28 | 2014-04-02 | 中国石油化工股份有限公司 | 利用微通道反应器合成2,2,4-三甲基-1,2-二氢喹啉及其聚合物的方法 |
-
2016
- 2016-06-29 CN CN201610495393.7A patent/CN106117137A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101274996A (zh) * | 2007-03-30 | 2008-10-01 | 住友橡胶工业株式会社 | 利用了微生物的防老剂、硫化促进剂或改性天然橡胶的制备方法 |
US20090306431A1 (en) * | 2008-06-10 | 2009-12-10 | Keitaro Fujikura | Process for producing antiaging agent, vulcanization accelerator or modified natural rubber by means of microorganism or plant |
CN202139185U (zh) * | 2011-07-11 | 2012-02-08 | 山东曹县斯递尔化工科技有限公司 | 一种用于生产橡胶防老剂rd缩聚反应的装置 |
CN103694169A (zh) * | 2012-09-28 | 2014-04-02 | 中国石油化工股份有限公司 | 利用微通道反应器合成2,2,4-三甲基-1,2-二氢喹啉及其聚合物的方法 |
Non-Patent Citations (1)
Title |
---|
覃光明,等: "《含能化合物合成反应与过程》", 31 May 2011 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106831564A (zh) * | 2016-12-21 | 2017-06-13 | 山东斯递尔化工科技有限公司 | 一种利用微反应装置连续制备抗氧剂224的方法 |
CN106831515A (zh) * | 2017-01-13 | 2017-06-13 | 山东斯递尔化工科技有限公司 | 利用微反应装置连续制备二硫化四苄基秋兰姆的方法 |
CN106995396A (zh) * | 2017-03-30 | 2017-08-01 | 山东斯递尔化工科技有限公司 | 一种利用微反应装置连续制备二甲基二硫代氨基甲酸钠的方法 |
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Inventor after: Guo Kai Inventor after: Wan Li Inventor after: Wang Jincai Inventor after: Fan Bingbing Inventor after: Zhao Xinyuan Inventor after: Ouyang Pingkai Inventor before: Guo Kai Inventor before: Wan Li Inventor before: Fan Bingbing Inventor before: Ouyang Pingkai |
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Effective date of registration: 20170601 Address after: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Applicant after: Nanjing Tech University Applicant after: SHANDONG STAIR CHEMICAL & TECHNOLOGY Co.,Ltd. Address before: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Applicant before: Nanjing Tech University |
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Application publication date: 20161116 |