CN107602419A - 一种基于二氧化碳耦合的1,5‑戊二异氰酸酯制备方法 - Google Patents
一种基于二氧化碳耦合的1,5‑戊二异氰酸酯制备方法 Download PDFInfo
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- CN107602419A CN107602419A CN201710997300.5A CN201710997300A CN107602419A CN 107602419 A CN107602419 A CN 107602419A CN 201710997300 A CN201710997300 A CN 201710997300A CN 107602419 A CN107602419 A CN 107602419A
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- pentanediamine
- carbon dioxide
- penta
- tank
- diisocyanate
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 121
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 61
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 60
- 125000005442 diisocyanate group Chemical group 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 230000008878 coupling Effects 0.000 title claims abstract description 7
- 238000010168 coupling process Methods 0.000 title claims abstract description 7
- 238000005859 coupling reaction Methods 0.000 title claims abstract description 7
- KJOMYNHMBRNCNY-UHFFFAOYSA-N pentane-1,1-diamine Chemical compound CCCCC(N)N KJOMYNHMBRNCNY-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 22
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 20
- DORYCBOQALEKBP-UHFFFAOYSA-N C(O)(O)=O.C(CCCC)(N)N Chemical compound C(O)(O)=O.C(CCCC)(N)N DORYCBOQALEKBP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001556 precipitation Methods 0.000 claims abstract description 15
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000004472 Lysine Substances 0.000 claims abstract description 14
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000003860 storage Methods 0.000 claims description 19
- 238000000746 purification Methods 0.000 claims description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000007599 discharging Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- 238000006552 photochemical reaction Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004807 desolvation Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- -1 o-dichlorohenzene Chemical compound 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 239000000047 product Substances 0.000 description 17
- 229960003646 lysine Drugs 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002773 nucleotide Substances 0.000 description 4
- 125000003729 nucleotide group Chemical group 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
- 150000008422 chlorobenzenes Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002527 isonitriles Chemical class 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 108010048581 Lysine decarboxylase Proteins 0.000 description 2
- 101150063552 cadB gene Proteins 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010353 genetic engineering Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 239000011527 polyurethane coating Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- 101100276041 Mycolicibacterium smegmatis (strain ATCC 700084 / mc(2)155) ctpD gene Proteins 0.000 description 1
- HZUKSQHMCTUZJL-UHFFFAOYSA-N P(=O)(O)(O)OCC=1C(=C(C(=NC1)C)O)C=O.P(=O)(O)(O)OC=1C(=NC=C(C1C=O)CO)C Chemical class P(=O)(O)(O)OCC=1C(=C(C(=NC1)C)O)C=O.P(=O)(O)(O)OC=1C(=NC=C(C1C=O)CO)C HZUKSQHMCTUZJL-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 101150008667 cadA gene Proteins 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000005588 carbonic acid salt group Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229960005337 lysine hydrochloride Drugs 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- VUKOCQOEAISBSD-UHFFFAOYSA-N pentane-1,1-diamine;hydrochloride Chemical compound Cl.CCCCC(N)N VUKOCQOEAISBSD-UHFFFAOYSA-N 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 1
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN201710997300.5A CN107602419B (zh) | 2017-10-23 | 2017-10-23 | 一种基于二氧化碳耦合的1,5-戊二异氰酸酯制备方法 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108997130A (zh) * | 2018-08-29 | 2018-12-14 | 南京工业大学 | 一种1,5-戊二胺萃取和成盐耦合的方法 |
CN109810024A (zh) * | 2019-03-28 | 2019-05-28 | 南京工业大学 | 一种用于制备戊二异氰酸酯的喷射回路反应器及其使用方法 |
CN114507160A (zh) * | 2021-12-06 | 2022-05-17 | 甘肃银光聚银化工有限公司 | 一种成盐光气化法合成1,5-戊二异氰酸酯的方法 |
CN115282887A (zh) * | 2022-07-05 | 2022-11-04 | 中国科学院过程工程研究所 | 一种二氧化碳制备1,5-戊二氨基甲酸甲酯的装置及利用其的制备方法 |
CN115850116A (zh) * | 2022-11-30 | 2023-03-28 | 摩珈(上海)生物科技有限公司 | 一种无溶剂超临界催化合成1,5-戊二异氰酸酯的方法 |
CN115850116B (zh) * | 2022-11-30 | 2024-06-28 | 摩珈(上海)生物科技有限公司 | 一种无溶剂超临界催化合成1,5-戊二异氰酸酯的方法 |
Citations (6)
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CN1926096A (zh) * | 2004-03-05 | 2007-03-07 | 日本曹达株式会社 | 异氰酸酯化合物的制造方法 |
EP2011782A1 (en) * | 2007-07-02 | 2009-01-07 | Huntsman International Llc | Process for the synthesis of carbamates using co2 |
CN101495643A (zh) * | 2006-08-01 | 2009-07-29 | 巴斯夫欧洲公司 | 制备五亚甲基1,5-二异氰酸酯的方法 |
CN102782146A (zh) * | 2010-03-01 | 2012-11-14 | 三井化学株式会社 | 1,5-戊二胺的制造方法、1,5-戊二胺、1,5-戊二异氰酸酯、1,5-戊二异氰酸酯的制造方法、聚异氰酸酯组合物、及聚氨酯树脂 |
CN104498519A (zh) * | 2014-12-19 | 2015-04-08 | 南京工业大学 | 一种表达重组载体及其应用 |
CN106045882A (zh) * | 2016-06-03 | 2016-10-26 | 山东崇舜化工有限公司 | 一种合成五亚甲基二异氰酸酯的方法 |
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2017
- 2017-10-23 CN CN201710997300.5A patent/CN107602419B/zh active Active
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CN1926096A (zh) * | 2004-03-05 | 2007-03-07 | 日本曹达株式会社 | 异氰酸酯化合物的制造方法 |
CN101495643A (zh) * | 2006-08-01 | 2009-07-29 | 巴斯夫欧洲公司 | 制备五亚甲基1,5-二异氰酸酯的方法 |
EP2011782A1 (en) * | 2007-07-02 | 2009-01-07 | Huntsman International Llc | Process for the synthesis of carbamates using co2 |
CN102782146A (zh) * | 2010-03-01 | 2012-11-14 | 三井化学株式会社 | 1,5-戊二胺的制造方法、1,5-戊二胺、1,5-戊二异氰酸酯、1,5-戊二异氰酸酯的制造方法、聚异氰酸酯组合物、及聚氨酯树脂 |
CN104498519A (zh) * | 2014-12-19 | 2015-04-08 | 南京工业大学 | 一种表达重组载体及其应用 |
CN106045882A (zh) * | 2016-06-03 | 2016-10-26 | 山东崇舜化工有限公司 | 一种合成五亚甲基二异氰酸酯的方法 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108997130A (zh) * | 2018-08-29 | 2018-12-14 | 南京工业大学 | 一种1,5-戊二胺萃取和成盐耦合的方法 |
CN109810024A (zh) * | 2019-03-28 | 2019-05-28 | 南京工业大学 | 一种用于制备戊二异氰酸酯的喷射回路反应器及其使用方法 |
CN114507160A (zh) * | 2021-12-06 | 2022-05-17 | 甘肃银光聚银化工有限公司 | 一种成盐光气化法合成1,5-戊二异氰酸酯的方法 |
CN115282887A (zh) * | 2022-07-05 | 2022-11-04 | 中国科学院过程工程研究所 | 一种二氧化碳制备1,5-戊二氨基甲酸甲酯的装置及利用其的制备方法 |
CN115282887B (zh) * | 2022-07-05 | 2024-02-09 | 中国科学院过程工程研究所 | 一种二氧化碳制备1,5-戊二氨基甲酸甲酯的装置及利用其的制备方法 |
CN115850116A (zh) * | 2022-11-30 | 2023-03-28 | 摩珈(上海)生物科技有限公司 | 一种无溶剂超临界催化合成1,5-戊二异氰酸酯的方法 |
CN115850116B (zh) * | 2022-11-30 | 2024-06-28 | 摩珈(上海)生物科技有限公司 | 一种无溶剂超临界催化合成1,5-戊二异氰酸酯的方法 |
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Inventor after: Xu Cheng Inventor after: Chen Kequan Inventor after: Tian Weilong Inventor after: He Yumei Inventor after: Wang Jing Inventor after: Wei Guoguang Inventor after: Cheng Qi Inventor after: OuYang Pingkai Inventor before: Chen Kequan Inventor before: Xu Cheng Inventor before: Tian Weilong Inventor before: He Yumei Inventor before: Wang Jing Inventor before: Wei Guoguang Inventor before: Cheng Qi Inventor before: OuYang Pingkai |