TWI801789B - 三氰基己烷純化方法 - Google Patents
三氰基己烷純化方法 Download PDFInfo
- Publication number
- TWI801789B TWI801789B TW109146907A TW109146907A TWI801789B TW I801789 B TWI801789 B TW I801789B TW 109146907 A TW109146907 A TW 109146907A TW 109146907 A TW109146907 A TW 109146907A TW I801789 B TWI801789 B TW I801789B
- Authority
- TW
- Taiwan
- Prior art keywords
- stream
- weight
- less
- adiponitrile
- tch
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 218
- 238000000746 purification Methods 0.000 title claims abstract description 39
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims abstract description 209
- 238000004821 distillation Methods 0.000 claims abstract description 182
- 238000009835 boiling Methods 0.000 claims abstract description 143
- 239000012535 impurity Substances 0.000 claims abstract description 62
- 239000007787 solid Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 26
- 238000004064 recycling Methods 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 17
- 239000011552 falling film Substances 0.000 claims description 10
- 239000010408 film Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 abstract description 13
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 description 86
- 238000000354 decomposition reaction Methods 0.000 description 30
- 241001417501 Lobotidae Species 0.000 description 17
- 239000000203 mixture Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 7
- 239000010409 thin film Substances 0.000 description 6
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- FYYPYNRGACGNNN-UHFFFAOYSA-N 3-[bis(2-cyanoethyl)amino]propanenitrile Chemical compound N#CCCN(CCC#N)CCC#N FYYPYNRGACGNNN-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002955 isolation Methods 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- SBAJRGRUGUQKAF-UHFFFAOYSA-N 3-(2-cyanoethylamino)propanenitrile Chemical compound N#CCCNCCC#N SBAJRGRUGUQKAF-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 1
- JRZLXTBWVCJQFZ-UHFFFAOYSA-N 2-cyanopentanamide Chemical compound CCCC(C#N)C(N)=O JRZLXTBWVCJQFZ-UHFFFAOYSA-N 0.000 description 1
- FRMJZJUVLPFLAB-UHFFFAOYSA-N 2-iminocyclopentane-1-carbonitrile Chemical compound N=C1CCCC1C#N FRMJZJUVLPFLAB-UHFFFAOYSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- MZQXEAUWIMFFCG-UHFFFAOYSA-N 3-(propylamino)propanenitrile Chemical compound CCCNCCC#N MZQXEAUWIMFFCG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920006079 Pentamid® Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- -1 adiponitrile Nitrile Chemical class 0.000 description 1
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- SXLDJBWDCDALLM-UHFFFAOYSA-N hexane-1,2,6-tricarbonitrile Chemical compound N#CCCCCC(C#N)CC#N SXLDJBWDCDALLM-UHFFFAOYSA-N 0.000 description 1
- LNLFLMCWDHZINJ-UHFFFAOYSA-N hexane-1,3,6-tricarbonitrile Chemical compound N#CCCCC(C#N)CCC#N LNLFLMCWDHZINJ-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/05—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton containing at least three cyano groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962955086P | 2019-12-30 | 2019-12-30 | |
| US62/955,086 | 2019-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW202138340A TW202138340A (zh) | 2021-10-16 |
| TWI801789B true TWI801789B (zh) | 2023-05-11 |
Family
ID=74347719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW109146907A TWI801789B (zh) | 2019-12-30 | 2020-12-30 | 三氰基己烷純化方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US11560353B2 (https=) |
| EP (1) | EP4085047A1 (https=) |
| JP (1) | JP2023509916A (https=) |
| KR (1) | KR20220119724A (https=) |
| CN (1) | CN114901632A (https=) |
| BR (1) | BR112022013065A2 (https=) |
| CA (1) | CA3163251A1 (https=) |
| IN (1) | IN202247039538A (https=) |
| MX (1) | MX2022008202A (https=) |
| TW (1) | TWI801789B (https=) |
| WO (1) | WO2021138491A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11780804B2 (en) | 2019-05-24 | 2023-10-10 | Ascend Performance Materials Operations Llc | Tricyanohexane purification methods |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003192631A (ja) * | 2001-12-27 | 2003-07-09 | Asahi Kasei Corp | １，３，６−ヘキサントリカルボン酸の製造方法 |
| TW200301759A (en) * | 2001-12-27 | 2003-07-16 | Asahi Chemical Ind | Polycarboxylic acid mixture |
| TW201728620A (zh) * | 2015-12-01 | 2017-08-16 | 阿散德性能材料營運公司 | 具有均一相對黏度及低凝膠含量之高分子量聚醯胺及共聚醯胺 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3451900A (en) | 1966-06-14 | 1969-06-24 | Vickers Zimmer Ag | Adiponitrile recovery by multistage vacuum distillation |
| US3844911A (en) | 1972-07-27 | 1974-10-29 | Phillips Petroleum Co | Method for producing adiponitrile |
| US4539302A (en) * | 1984-04-30 | 1985-09-03 | E. I. Du Pont De Nemours And Company | Recovery of zerovalent nickel complexes |
| JPH0745440B2 (ja) * | 1986-05-20 | 1995-05-17 | 旭化成工業株式会社 | ４−アミノメチル−１，８−ジアミノオクタンの製造方法 |
| JP2003183239A (ja) * | 2001-12-21 | 2003-07-03 | Asahi Kasei Corp | 低色相トリニトリル混合物及びその製造法 |
| JP2003192630A (ja) * | 2001-12-27 | 2003-07-09 | Asahi Kasei Corp | １，３，６−ヘキサントリカルボン酸の製造法 |
| US6599398B1 (en) | 2002-07-17 | 2003-07-29 | E. I. Du Pont De Nemours And Company | Recovery of adiponitrile from a mixture of adiponitrile, aminocapronitrile and hexamethylenediamine |
| KR101516854B1 (ko) * | 2012-05-22 | 2015-05-04 | 주식회사 엘지화학 | 리튬 이차전지용 비수 전해액 및 이를 포함하는 리튬이차전지 |
| EP4061795A1 (en) * | 2019-11-22 | 2022-09-28 | Ascend Performance Materials Operations LLC | Compositions comprising triscyanohexane |
-
2020
- 2020-12-30 IN IN202247039538A patent/IN202247039538A/en unknown
- 2020-12-30 CA CA3163251A patent/CA3163251A1/en active Pending
- 2020-12-30 MX MX2022008202A patent/MX2022008202A/es unknown
- 2020-12-30 CN CN202080090935.7A patent/CN114901632A/zh active Pending
- 2020-12-30 US US17/138,591 patent/US11560353B2/en active Active
- 2020-12-30 EP EP20848764.5A patent/EP4085047A1/en not_active Withdrawn
- 2020-12-30 WO PCT/US2020/067567 patent/WO2021138491A1/en not_active Ceased
- 2020-12-30 KR KR1020227026065A patent/KR20220119724A/ko not_active Ceased
- 2020-12-30 TW TW109146907A patent/TWI801789B/zh active
- 2020-12-30 JP JP2022540517A patent/JP2023509916A/ja not_active Ceased
- 2020-12-30 BR BR112022013065A patent/BR112022013065A2/pt not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003192631A (ja) * | 2001-12-27 | 2003-07-09 | Asahi Kasei Corp | １，３，６−ヘキサントリカルボン酸の製造方法 |
| TW200301759A (en) * | 2001-12-27 | 2003-07-16 | Asahi Chemical Ind | Polycarboxylic acid mixture |
| US20050010021A1 (en) * | 2001-12-27 | 2005-01-13 | Hideki Date | Polycarboxylic acid mixture |
| TW201728620A (zh) * | 2015-12-01 | 2017-08-16 | 阿散德性能材料營運公司 | 具有均一相對黏度及低凝膠含量之高分子量聚醯胺及共聚醯胺 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20210198186A1 (en) | 2021-07-01 |
| US11560353B2 (en) | 2023-01-24 |
| TW202138340A (zh) | 2021-10-16 |
| MX2022008202A (es) | 2022-10-07 |
| WO2021138491A1 (en) | 2021-07-08 |
| KR20220119724A (ko) | 2022-08-30 |
| CN114901632A (zh) | 2022-08-12 |
| BR112022013065A2 (pt) | 2022-09-06 |
| EP4085047A1 (en) | 2022-11-09 |
| JP2023509916A (ja) | 2023-03-10 |
| CA3163251A1 (en) | 2021-07-08 |
| IN202247039538A (https=) | 2022-07-15 |
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