CN1172906C - 脂环族连伯二胺的氰乙基化 - Google Patents
脂环族连伯二胺的氰乙基化 Download PDFInfo
- Publication number
- CN1172906C CN1172906C CNB011255285A CN01125528A CN1172906C CN 1172906 C CN1172906 C CN 1172906C CN B011255285 A CNB011255285 A CN B011255285A CN 01125528 A CN01125528 A CN 01125528A CN 1172906 C CN1172906 C CN 1172906C
- Authority
- CN
- China
- Prior art keywords
- diamino
- cyclohexane
- cyanoethylation
- amine
- reaction
- 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 abstract description 39
- 125000002723 alicyclic group Chemical group 0.000 title claims description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 19
- 150000004985 diamines Chemical group 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 33
- -1 alicyclic diamines Chemical class 0.000 claims description 24
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical group NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 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 group CCCCC1CCC(N)C(N)C1 PPCNFAQBTKCMOL-UHFFFAOYSA-N 0.000 claims 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical group NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 5
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical class CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 12
- 150000003141 primary amines Chemical class 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003760 magnetic stirring Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000000170 chemical ionisation mass spectrum Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000009466 transformation 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005070 sampling Methods 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
- GNMCGMFNBARSIY-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6,7,8,8a,9,10,10a-tetradecahydrophenanthrene Chemical compound C1CCCC2C3CCCCC3CCC21 GNMCGMFNBARSIY-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- UYLKHKGPQNFZII-UHFFFAOYSA-N 2-butylcyclohexane-1,1-diamine Chemical group C(CCC)C1C(CCCC1)(N)N UYLKHKGPQNFZII-UHFFFAOYSA-N 0.000 description 1
- HPUYBWQXCAQWIT-UHFFFAOYSA-N 2-ethylcyclohexane-1,1-diamine Chemical compound CCC1CCCCC1(N)N HPUYBWQXCAQWIT-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002220 fluorenes Chemical class 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
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- NVGGIRZMSYUNQN-UHFFFAOYSA-N piperidine-4,4-diamine Chemical group NC1(N)CCNCC1 NVGGIRZMSYUNQN-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
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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 (2)
| Publication Number | Publication Date |
|---|---|
| CN1337393A CN1337393A (zh) | 2002-02-27 |
| CN1172906C true CN1172906C (zh) | 2004-10-27 |
Family
ID=24543609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011255285A Expired - Fee Related CN1172906C (zh) | 2000-08-09 | 2001-08-08 | 脂环族连伯二胺的氰乙基化 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108383756A (zh) * | 2018-02-07 | 2018-08-10 | 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 |
Families Citing this family (9)
| 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 |
| WO2007031534A1 (de) * | 2005-09-15 | 2007-03-22 | Basf Aktiengesellschaft | Verfahren zur herstellung von beta-aminopropionsäurederivaten |
| 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 |
| 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108383756A (zh) * | 2018-02-07 | 2018-08-10 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6245932B1 (en) | 2001-06-12 |
| CN1337393A (zh) | 2002-02-27 |
| EP1179526A3 (en) | 2003-07-30 |
| JP4142861B2 (ja) | 2008-09-03 |
| CA2354773A1 (en) | 2002-03-08 |
| JP2002053542A (ja) | 2002-02-19 |
| BR0106826A (pt) | 2003-09-02 |
| EP1179526A2 (en) | 2002-02-13 |
| CA2354773C (en) | 2005-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20041027 Termination date: 20090908 |