JP4142861B2 - 環状脂肪族の第１級ビシナルジアミンのシアノエチル化 - Google Patents
環状脂肪族の第１級ビシナルジアミンのシアノエチル化 Download PDFInfo
- Publication number
- JP4142861B2 JP4142861B2 JP2001240131A JP2001240131A JP4142861B2 JP 4142861 B2 JP4142861 B2 JP 4142861B2 JP 2001240131 A JP2001240131 A JP 2001240131A JP 2001240131 A JP2001240131 A JP 2001240131A JP 4142861 B2 JP4142861 B2 JP 4142861B2
- Authority
- JP
- Japan
- Prior art keywords
- diaminocyclohexane
- acrylonitrile
- amine
- reaction
- cyanoethylation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000007278 cyanoethylation reaction Methods 0.000 title claims description 24
- 150000004985 diamines Chemical group 0.000 title claims description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 12
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical group NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims description 6
- -1 t-butyl-2,3-diaminocyclohexane Chemical compound 0.000 claims description 6
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 5
- AKQPXKGNPMHWBZ-UHFFFAOYSA-N 3-methylcyclohexane-1,2-diamine Chemical compound CC1CCCC(N)C1N AKQPXKGNPMHWBZ-UHFFFAOYSA-N 0.000 claims description 3
- KKYGOXSPNXROTG-UHFFFAOYSA-N 4-methylcyclohexane-1,2-diamine Chemical compound CC1CCC(N)C(N)C1 KKYGOXSPNXROTG-UHFFFAOYSA-N 0.000 claims description 3
- PPCNFAQBTKCMOL-UHFFFAOYSA-N 4-butylcyclohexane-1,2-diamine Chemical compound CCCCC1CCC(N)C(N)C1 PPCNFAQBTKCMOL-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000003141 primary amines Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 7
- 150000003335 secondary amines Chemical class 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 4
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BDYVWDMHYNGVGE-UHFFFAOYSA-N [2-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCCC1CN BDYVWDMHYNGVGE-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HPUYBWQXCAQWIT-UHFFFAOYSA-N 2-ethylcyclohexane-1,1-diamine Chemical compound CCC1CCCCC1(N)N HPUYBWQXCAQWIT-UHFFFAOYSA-N 0.000 description 1
- RYJJTKMZAVWCCN-UHFFFAOYSA-N 2-propan-2-ylcyclohexane-1,1-diamine Chemical compound CC(C)C1CCCCC1(N)N RYJJTKMZAVWCCN-UHFFFAOYSA-N 0.000 description 1
- ABOJMOBJFAQTAL-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-2h-quinoxaline-1,2-diamine Chemical compound C1CCCC2N(N)C(N)CNC21 ABOJMOBJFAQTAL-UHFFFAOYSA-N 0.000 description 1
- OEUIIRAAMHTABH-UHFFFAOYSA-N 3-[(2-aminocyclohexyl)amino]propanenitrile Chemical compound NC1CCCCC1NCCC#N OEUIIRAAMHTABH-UHFFFAOYSA-N 0.000 description 1
- LDVABWTVBMZKHB-UHFFFAOYSA-N 3-[[2-(2-cyanoethylamino)cyclohexyl]amino]propanenitrile Chemical compound N#CCCNC1CCCCC1NCCC#N LDVABWTVBMZKHB-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- JXBPSENIJJPTCI-UHFFFAOYSA-N ethyl cyanate Chemical compound CCOC#N JXBPSENIJJPTCI-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- UQZMEMXNAABHEG-UHFFFAOYSA-N piperidine-1,2-diamine Chemical compound NC1CCCCN1N UQZMEMXNAABHEG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/634398 | 2000-08-09 | ||
| US09/634,398 US6245932B1 (en) | 2000-08-09 | 2000-08-09 | Cyanoethylation of cycloaliphatic vicinal primary diamines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002053542A JP2002053542A (ja) | 2002-02-19 |
| JP2002053542A5 JP2002053542A5 (enExample) | 2005-04-14 |
| JP4142861B2 true JP4142861B2 (ja) | 2008-09-03 |
Family
ID=24543609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001240131A Expired - Fee Related JP4142861B2 (ja) | 2000-08-09 | 2001-08-08 | 環状脂肪族の第１級ビシナルジアミンのシアノエチル化 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6245932B1 (enExample) |
| EP (1) | EP1179526A3 (enExample) |
| JP (1) | JP4142861B2 (enExample) |
| CN (1) | CN1172906C (enExample) |
| BR (1) | BR0106826A (enExample) |
| CA (1) | CA2354773C (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6433212B1 (en) * | 2001-01-31 | 2002-08-13 | Air Products And Chemicals, Inc. | Synthesis of new polynitriles from cycloaliphatic vicinal primary diamines |
| ATE427297T1 (de) * | 2005-09-15 | 2009-04-15 | Basf Se | Verfahren zur herstellung von beta- aminopropionsaurederivaten |
| US20080194857A1 (en) | 2007-02-12 | 2008-08-14 | Air Products And Chemicals, Inc. | Selective Manufacture of N,N'-BIS(Cyanoethyl)-1,2-Ethylenediamine and N, N'-BIS(3-aminopropyl)-1,2-Ethylenediamine |
| CN107417888B (zh) * | 2017-05-02 | 2019-11-26 | 武汉理工大学 | 一种耐低温环氧树脂及其制备方法 |
| CN108383756B (zh) * | 2018-02-07 | 2021-04-20 | 万华化学集团股份有限公司 | 一种氰乙基胺类化合物的制备方法 |
| CN110467535A (zh) * | 2018-05-10 | 2019-11-19 | 岳阳昌德环境科技有限公司 | 改性环己二胺组合物及其制备方法 |
| CN113372241B (zh) * | 2020-03-09 | 2023-01-13 | 万华化学集团股份有限公司 | 脂肪族伯胺一步法合成双腈乙基叔胺的方法 |
| CN112920614A (zh) * | 2021-01-28 | 2021-06-08 | 金闻闻 | 一种耐高温防水型环氧沥青及其制备方法 |
| CN114853633B (zh) * | 2022-03-28 | 2023-05-30 | 万华化学集团股份有限公司 | 一种双氨丙基脂环叔胺的制备方法 |
| CN114890913B (zh) * | 2022-06-07 | 2023-05-26 | 万华化学集团股份有限公司 | 一种制备双氰乙基环己胺的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2372895A (en) * | 1943-04-27 | 1945-04-03 | Monsanto Chemicals | Vulcanization of rubber |
| CH397712A (de) | 1961-08-04 | 1965-08-31 | Geigy Ag J R | Verfahren zur Cyanäthylierung primärer und sekundärer aromatischer Amine |
| US3496213A (en) | 1967-07-11 | 1970-02-17 | Du Pont | Mono-cyanoethylation of aromatic amines with an aqueous zinc chloride catalyst |
| US4153567A (en) | 1977-11-10 | 1979-05-08 | Milliken Research Corporation | Additives for lubricants and fuels |
| US4321354A (en) | 1978-07-17 | 1982-03-23 | Milliken Research Corporation | Polyamine substituted cycloaliphatic compounds |
| US6433212B1 (en) * | 2001-01-31 | 2002-08-13 | Air Products And Chemicals, Inc. | Synthesis of new polynitriles from cycloaliphatic vicinal primary diamines |
-
2000
- 2000-08-09 US US09/634,398 patent/US6245932B1/en not_active Expired - Fee Related
-
2001
- 2001-08-02 CA CA002354773A patent/CA2354773C/en not_active Expired - Fee Related
- 2001-08-03 BR BR0106826-1A patent/BR0106826A/pt not_active IP Right Cessation
- 2001-08-08 CN CNB011255285A patent/CN1172906C/zh not_active Expired - Fee Related
- 2001-08-08 EP EP01118766A patent/EP1179526A3/en not_active Withdrawn
- 2001-08-08 JP JP2001240131A patent/JP4142861B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1179526A3 (en) | 2003-07-30 |
| CN1172906C (zh) | 2004-10-27 |
| US6245932B1 (en) | 2001-06-12 |
| BR0106826A (pt) | 2003-09-02 |
| JP2002053542A (ja) | 2002-02-19 |
| CN1337393A (zh) | 2002-02-27 |
| EP1179526A2 (en) | 2002-02-13 |
| CA2354773A1 (en) | 2002-03-08 |
| CA2354773C (en) | 2005-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0229066B2 (enExample) | ||
| JP5377335B2 (ja) | テトラエチレンペンタアミンの製造方法 | |
| JPS6233211B2 (enExample) | ||
| JP4142861B2 (ja) | 環状脂肪族の第１級ビシナルジアミンのシアノエチル化 | |
| JPH03240757A (ja) | ポリアミンとそれらの生成方法 | |
| EP3652144A1 (en) | Process for making higher ethylene amines | |
| JP6130298B2 (ja) | 高分子量ポリアルキレンアミンへの窒素含有化合物のアミノ基転移 | |
| JP2014503490A5 (enExample) | ||
| US5070202A (en) | Cyanobutylation of amines with 2-pentenitrile | |
| US6433212B1 (en) | Synthesis of new polynitriles from cycloaliphatic vicinal primary diamines | |
| US4642344A (en) | Polyamines | |
| US4845297A (en) | Process for producing polyamines | |
| US5247078A (en) | Synthesis of diaza crown ethers | |
| JPH06184063A (ja) | ヘキサメチレンテトラミンとアミン又はニトリルとの反応によるメチル化第３級アミンの製造方法 | |
| JP4001937B2 (ja) | アミノプロピオニトリルの製法 | |
| CN100352799C (zh) | 由伯胺和腈制备叔胺的方法 | |
| US5902883A (en) | Cyanobutylation of ammonia, alkylamines and hydrazine with 3-pentenenitrile, 4-pentenenitrile or mixtures thereof | |
| JP4822649B2 (ja) | ３−ヒドロキシアルカンニトリルおよびヒドロキシアミノアルカンの製造方法 | |
| US5237088A (en) | Transfer hydrogenation of nitriles using amine donors | |
| JPS5835179A (ja) | ピペラジンおよびピペラジン誘導体の製造方法 | |
| US5449780A (en) | Process for the preparation of 1,3- and 1,5-dialkylpiperidone-2 | |
| JPS63287752A (ja) | Ｎ−メチル化第３級アミンの製造方法 | |
| TW200800865A (en) | Process of making 3-aminopentanenitrile | |
| CZ120993A3 (en) | Process for preparing aminopropionitriles | |
| JPH02306966A (ja) | イミダゾリン誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040604 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040604 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070625 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20071106 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080125 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080610 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080613 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110620 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |