JPH0137409B2 - - Google Patents
Info
- Publication number
- JPH0137409B2 JPH0137409B2 JP2487687A JP2487687A JPH0137409B2 JP H0137409 B2 JPH0137409 B2 JP H0137409B2 JP 2487687 A JP2487687 A JP 2487687A JP 2487687 A JP2487687 A JP 2487687A JP H0137409 B2 JPH0137409 B2 JP H0137409B2
- Authority
- JP
- Japan
- Prior art keywords
- residue
- group
- compound
- aliphatic hydrocarbon
- aromatic
- 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
Links
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000004952 Polyamide Substances 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229920002647 polyamide Polymers 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005219 aminonitrile group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000004985 diamines Chemical class 0.000 claims description 11
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 6
- 239000005749 Copper compound Substances 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000005078 molybdenum compound Substances 0.000 claims description 3
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 3
- 150000002816 nickel compounds Chemical class 0.000 claims description 3
- 150000002908 osmium compounds Chemical class 0.000 claims description 3
- 150000003284 rhodium compounds Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 7
- 229920002302 Nylon 6,6 Polymers 0.000 description 5
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical class N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000002825 nitriles Chemical class 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
- 150000001412 amines Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920000299 Nylon 12 Polymers 0.000 description 2
- 229920003188 Nylon 3 Polymers 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- -1 Polyhexamethylene terephthalamide Polymers 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 2
- BVJKISUCBKDPOW-UHFFFAOYSA-N 12-aminododecanenitrile Chemical compound NCCCCCCCCCCCC#N BVJKISUCBKDPOW-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- MLIYPCQSOXNTLJ-UHFFFAOYSA-N carbon monoxide;ruthenium dihydride;triphenylphosphane Chemical compound [RuH2].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MLIYPCQSOXNTLJ-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000232 polyglycine polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
Landscapes
- Polyamides (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2487687A JPS62223227A (ja) | 1985-03-08 | 1987-02-06 | ジニトリルとジアミン又はアミノニトリルからのポリアミドの製造方法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044939A JPS61205221A (ja) | 1985-03-08 | 1985-03-08 | ニトリルとアミンからのアミドの製造方法 |
| JP2487687A JPS62223227A (ja) | 1985-03-08 | 1987-02-06 | ジニトリルとジアミン又はアミノニトリルからのポリアミドの製造方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60044939A Division JPS61205221A (ja) | 1985-03-08 | 1985-03-08 | ニトリルとアミンからのアミドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62223227A JPS62223227A (ja) | 1987-10-01 |
| JPH0137409B2 true JPH0137409B2 (enrdf_load_html_response) | 1989-08-07 |
Family
ID=26362449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2487687A Granted JPS62223227A (ja) | 1985-03-08 | 1987-02-06 | ジニトリルとジアミン又はアミノニトリルからのポリアミドの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62223227A (enrdf_load_html_response) |
-
1987
- 1987-02-06 JP JP2487687A patent/JPS62223227A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62223227A (ja) | 1987-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0197657B1 (en) | A novel process for preparing amides from nitriles and amines | |
| US3158635A (en) | Bis-adduction products and methods of preparing same | |
| US4082811A (en) | Recovery of metal and triarylborane catalyst components from olefin hydrocyanation residue | |
| JP2010006831A (ja) | アモナフィド塩 | |
| US4254059A (en) | Process for hydrogenation of nitriles | |
| JPS61183251A (ja) | ４‐ニトロジフエニルアミン類の製造方法 | |
| JPH03240757A (ja) | ポリアミンとそれらの生成方法 | |
| EP0372922B1 (en) | Preparation process of N-substituted maleimides | |
| US6245932B1 (en) | Cyanoethylation of cycloaliphatic vicinal primary diamines | |
| JPS6257193B2 (enrdf_load_html_response) | ||
| JPH04221325A (ja) | ２−ペンテンニトリルを用いたアミン類のシアノブチル化 | |
| JPH0137409B2 (enrdf_load_html_response) | ||
| SE469130B (sv) | Foerfarande foer framstaellning av glyoxylylspermidin och anvaendningen daerav foer framstaellning av 15-deoxispergualin- beslaektade foereningar | |
| SU461504A3 (ru) | Способ получени производных изотиазола | |
| US6433212B1 (en) | Synthesis of new polynitriles from cycloaliphatic vicinal primary diamines | |
| JP4605328B2 (ja) | アルキレンビスメラミンの製造方法 | |
| JP4643567B2 (ja) | アミドカルボニル化反応方法 | |
| US20080177050A1 (en) | Alpha, omega-difunctional aldaramides | |
| HU214942B (hu) | Eljárás N-helyettesített glicin-észterek és glicin, továbbá ezekből indoxil- és indigószármazékok előállítására | |
| US4940796A (en) | 2,6-substituted-4-aminopyridines and their corresponding intermediates | |
| JP2699181B2 (ja) | テトラヒドロピリミジン化合物の製造法 | |
| US5025107A (en) | Process for coproduction of arylene diamine dihalides and alkyl halides | |
| US5902883A (en) | Cyanobutylation of ammonia, alkylamines and hydrazine with 3-pentenenitrile, 4-pentenenitrile or mixtures thereof | |
| WO2000071542A1 (en) | Improved synthesis of a tetraamido macrocycle ligand | |
| EP0134889B1 (en) | Cyclohexane carboxylic acids and derivatives thereof as antidysrhythmic agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |