DE2041772A1 - Amidgruppen enthaltende aliphatische Diamine und ein Verfahren zu ihrer Herstellung - Google Patents
Amidgruppen enthaltende aliphatische Diamine und ein Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2041772A1 DE2041772A1 DE19702041772 DE2041772A DE2041772A1 DE 2041772 A1 DE2041772 A1 DE 2041772A1 DE 19702041772 DE19702041772 DE 19702041772 DE 2041772 A DE2041772 A DE 2041772A DE 2041772 A1 DE2041772 A1 DE 2041772A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- radical
- diphenylene
- naphthylene
- weight
- 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.)
- Pending
Links
- -1 aliphatic diamines Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 8
- 125000003368 amide group Chemical group 0.000 title claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 12
- 239000005457 ice water Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZDBWYUOUYNQZBM-UHFFFAOYSA-N 3-(aminomethyl)aniline Chemical compound NCC1=CC=CC(N)=C1 ZDBWYUOUYNQZBM-UHFFFAOYSA-N 0.000 description 1
- VYUNCHWZPFLDAP-UHFFFAOYSA-N 3-(aminomethyl)aniline;dihydrochloride Chemical compound Cl.Cl.NCC1=CC=CC(N)=C1 VYUNCHWZPFLDAP-UHFFFAOYSA-N 0.000 description 1
- LNPMZQXEPNWCMG-UHFFFAOYSA-N 4-(2-aminoethyl)aniline Chemical compound NCCC1=CC=C(N)C=C1 LNPMZQXEPNWCMG-UHFFFAOYSA-N 0.000 description 1
- JQVYAXXCWXIJHB-UHFFFAOYSA-N 4-(2-aminoethyl)aniline;dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=C(N)C=C1 JQVYAXXCWXIJHB-UHFFFAOYSA-N 0.000 description 1
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 1
- CNEPNGNLZCESMV-UHFFFAOYSA-N 4-[3-(aminomethyl)phenoxy]aniline Chemical compound NCC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 CNEPNGNLZCESMV-UHFFFAOYSA-N 0.000 description 1
- SAORQTWFXWLIFA-UHFFFAOYSA-N 4-[4-(aminomethyl)phenoxy]aniline Chemical compound C1=CC(CN)=CC=C1OC1=CC=C(N)C=C1 SAORQTWFXWLIFA-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical compound ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702041772 DE2041772A1 (de) | 1970-08-22 | 1970-08-22 | Amidgruppen enthaltende aliphatische Diamine und ein Verfahren zu ihrer Herstellung |
| FR7130474A FR2103453A1 (enExample) | 1970-08-22 | 1971-08-20 | |
| NL7111529A NL7111529A (enExample) | 1970-08-22 | 1971-08-20 | |
| GB3912371A GB1341417A (en) | 1970-08-22 | 1971-08-20 | Diamines containing amide groups and a process for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702041772 DE2041772A1 (de) | 1970-08-22 | 1970-08-22 | Amidgruppen enthaltende aliphatische Diamine und ein Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2041772A1 true DE2041772A1 (de) | 1972-02-24 |
Family
ID=5780484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702041772 Pending DE2041772A1 (de) | 1970-08-22 | 1970-08-22 | Amidgruppen enthaltende aliphatische Diamine und ein Verfahren zu ihrer Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2041772A1 (enExample) |
| FR (1) | FR2103453A1 (enExample) |
| GB (1) | GB1341417A (enExample) |
| NL (1) | NL7111529A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH650767A5 (de) * | 1981-12-17 | 1985-08-15 | Ciba Geigy Ag | Amingruppenhaltige carbonsaeureamide und ihre verwendung als haerter fuer epoxidharze. |
-
1970
- 1970-08-22 DE DE19702041772 patent/DE2041772A1/de active Pending
-
1971
- 1971-08-20 GB GB3912371A patent/GB1341417A/en not_active Expired
- 1971-08-20 NL NL7111529A patent/NL7111529A/xx unknown
- 1971-08-20 FR FR7130474A patent/FR2103453A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL7111529A (enExample) | 1972-02-24 |
| FR2103453A1 (enExample) | 1972-04-14 |
| GB1341417A (en) | 1973-12-19 |
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