CN107001236B - 一种1,5-戊二胺的纯化方法及1,5-戊二胺 - Google Patents
一种1,5-戊二胺的纯化方法及1,5-戊二胺 Download PDFInfo
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- CN107001236B CN107001236B CN201480083876.5A CN201480083876A CN107001236B CN 107001236 B CN107001236 B CN 107001236B CN 201480083876 A CN201480083876 A CN 201480083876A CN 107001236 B CN107001236 B CN 107001236B
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- pentanediamine
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- piperidine
- tetrahydropyridine
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- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 title claims abstract description 404
- 238000000034 method Methods 0.000 title claims abstract description 45
- 238000000746 purification Methods 0.000 title abstract description 9
- 238000006722 reduction reaction Methods 0.000 claims abstract description 30
- 230000008569 process Effects 0.000 claims abstract description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 92
- 238000006243 chemical reaction Methods 0.000 claims description 39
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical compound C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 claims description 38
- 239000012535 impurity Substances 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000003638 chemical reducing agent Substances 0.000 claims description 18
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 230000009467 reduction Effects 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 33
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 24
- KJOMYNHMBRNCNY-UHFFFAOYSA-N pentane-1,1-diamine Chemical class CCCCC(N)N KJOMYNHMBRNCNY-UHFFFAOYSA-N 0.000 description 24
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- 239000012279 sodium borohydride Substances 0.000 description 7
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- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 6
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- 229910010084 LiAlH4 Inorganic materials 0.000 description 3
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- 229910001220 stainless steel Inorganic materials 0.000 description 3
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- -1 tetralin peroxide Chemical class 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108010048581 Lysine decarboxylase Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 229910021529 ammonia Inorganic materials 0.000 description 2
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- 239000000543 intermediate Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000011701 zinc Substances 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
- 241000894006 Bacteria Species 0.000 description 1
- RKLJSFSLDCKWPH-UHFFFAOYSA-N C(CCCCC(=O)O)(=O)O.C(CCCC)(N)N Chemical compound C(CCCCC(=O)O)(=O)O.C(CCCC)(N)N RKLJSFSLDCKWPH-UHFFFAOYSA-N 0.000 description 1
- 108090000489 Carboxy-Lyases Proteins 0.000 description 1
- 241000186226 Corynebacterium glutamicum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
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- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
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- 238000005265 energy consumption Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
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- 238000001728 nano-filtration Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 229920006118 nylon 56 Polymers 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
纯化的1,5-戊二胺中THP含量 | 尼龙黄色指数 | |
实施例1 | 0.06% | 6 |
实施例2 | 0.05% | 5 |
实施例3 | 0.04% | 5 |
实施例4 | 0.05% | 6 |
实施例5 | 0.03% | 4 |
实施例6 | 0.006% | 2 |
实施例7 | 0.003% | 1 |
实施例8 | 0.004% | 1 |
实施例9 | 0.01% | 3 |
实施例10 | 0.007% | 2 |
对比例1 | 0.2% | 15 |
Claims (5)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2014/094124 WO2016095136A1 (zh) | 2014-12-17 | 2014-12-17 | 一种1,5-戊二胺的纯化方法及1,5-戊二胺 |
Publications (3)
Publication Number | Publication Date |
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CN107001236A CN107001236A (zh) | 2017-08-01 |
CN107001236A8 CN107001236A8 (zh) | 2017-11-07 |
CN107001236B true CN107001236B (zh) | 2020-03-17 |
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CN201480083876.5A Active CN107001236B (zh) | 2014-12-17 | 2014-12-17 | 一种1,5-戊二胺的纯化方法及1,5-戊二胺 |
Country Status (6)
Country | Link |
---|---|
US (2) | US10538481B2 (zh) |
EP (1) | EP3235804B1 (zh) |
JP (1) | JP6593812B2 (zh) |
CN (1) | CN107001236B (zh) |
ES (1) | ES2907261T3 (zh) |
WO (1) | WO2016095136A1 (zh) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6744808B2 (ja) * | 2016-11-29 | 2020-08-19 | 三井化学株式会社 | ペンタメチレンジイソシアネートの製造方法 |
CN110787472B (zh) * | 2018-08-01 | 2024-02-13 | 上海凯赛生物技术股份有限公司 | 戊二胺浓缩系统及浓缩方法 |
CN108997141B (zh) * | 2018-08-28 | 2021-10-19 | 河北美邦工程科技股份有限公司 | 一种1,5-戊二胺的制备方法 |
KR102352784B1 (ko) | 2020-03-19 | 2022-01-18 | 씨제이제일제당 주식회사 | 탄산 함유 디아미노알칸 용액의 분리막 분리 공정 |
EP3939960A1 (de) | 2020-07-15 | 2022-01-19 | Covestro Deutschland AG | Verfahren zur gewinnung von diaminen aus wässrigen mischungen |
CN114315603B (zh) * | 2020-09-30 | 2024-04-05 | 上海凯赛生物技术股份有限公司 | 一种1,5-戊二胺的提取方法及其所得的1,5-戊二胺产品 |
EP4151618A1 (en) | 2021-09-20 | 2023-03-22 | Covestro Deutschland AG | Obtaining aliphatic amines from compositions |
CN116410094A (zh) * | 2021-12-31 | 2023-07-11 | 惠州市绿色能源与新材料研究院 | 一种聚合级生物基戊二胺精制提纯工艺 |
CN116041278A (zh) * | 2022-12-30 | 2023-05-02 | 摩珈(上海)生物科技有限公司 | 一种使用微反应器装置和含钌催化剂制备哌啶的方法 |
CN116041279A (zh) * | 2022-12-30 | 2023-05-02 | 摩珈(上海)生物科技有限公司 | 一种使用高压釜装置和含钌催化剂制备哌啶的方法 |
CN116354829A (zh) * | 2023-04-07 | 2023-06-30 | 中国科学院长春应用化学研究所 | 一种戊二胺己二酸盐的制备方法及其应用 |
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2014
- 2014-12-17 ES ES14908171T patent/ES2907261T3/es active Active
- 2014-12-17 US US15/537,168 patent/US10538481B2/en active Active
- 2014-12-17 EP EP14908171.3A patent/EP3235804B1/en active Active
- 2014-12-17 JP JP2017550967A patent/JP6593812B2/ja active Active
- 2014-12-17 WO PCT/CN2014/094124 patent/WO2016095136A1/zh active Application Filing
- 2014-12-17 CN CN201480083876.5A patent/CN107001236B/zh active Active
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2019
- 2019-12-05 US US16/704,000 patent/US11008279B2/en active Active
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CN102449029A (zh) * | 2009-03-30 | 2012-05-09 | 东丽株式会社 | 聚酰胺树脂、聚酰胺树脂组合物和由它们形成的成型品 |
CN103347852A (zh) * | 2011-03-09 | 2013-10-09 | 三井化学株式会社 | 戊二异氰酸酯、戊二异氰酸酯的制造方法、多异氰酸酯组合物、聚氨酯树脂及聚脲树脂 |
CN104098508A (zh) * | 2013-04-15 | 2014-10-15 | 上海凯赛生物技术研发中心有限公司 | 2, 3, 4, 5-四氢吡啶及其衍生物的制备方法 |
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EP3235804B1 (en) | 2022-01-19 |
US10538481B2 (en) | 2020-01-21 |
EP3235804A4 (en) | 2018-09-05 |
WO2016095136A1 (zh) | 2016-06-23 |
CN107001236A8 (zh) | 2017-11-07 |
ES2907261T3 (es) | 2022-04-22 |
CN107001236A (zh) | 2017-08-01 |
US20200109104A1 (en) | 2020-04-09 |
JP2018501308A (ja) | 2018-01-18 |
JP6593812B2 (ja) | 2019-10-23 |
US11008279B2 (en) | 2021-05-18 |
US20180002272A1 (en) | 2018-01-04 |
EP3235804A1 (en) | 2017-10-25 |
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