DE2133650A1 - Verfahren zur Herstellung langketü ger alpha omega Diamino alkane - Google Patents
Verfahren zur Herstellung langketü ger alpha omega Diamino alkaneInfo
- Publication number
- DE2133650A1 DE2133650A1 DE19712133650 DE2133650A DE2133650A1 DE 2133650 A1 DE2133650 A1 DE 2133650A1 DE 19712133650 DE19712133650 DE 19712133650 DE 2133650 A DE2133650 A DE 2133650A DE 2133650 A1 DE2133650 A1 DE 2133650A1
- Authority
- DE
- Germany
- Prior art keywords
- diamino
- diamine
- long
- reaction
- melting point
- 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
- 238000000034 method Methods 0.000 title claims description 17
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 6
- 230000007774 longterm Effects 0.000 title 1
- 150000004985 diamines Chemical class 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000001924 cycloalkanes Chemical class 0.000 claims description 4
- QFMSQSOYTFZACB-UHFFFAOYSA-N docosane-1,22-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCN QFMSQSOYTFZACB-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- IAFYEFQPNIPAGF-UHFFFAOYSA-N tetracosane-1,24-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCCCN IAFYEFQPNIPAGF-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- OCJLSVQJNZKGKL-UHFFFAOYSA-N tricosane-1,23-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCCN OCJLSVQJNZKGKL-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 238000004455 differential thermal analysis Methods 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 241000786363 Rhampholeon spectrum Species 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- -1 ammonium halide Chemical class 0.000 description 4
- 238000005915 ammonolysis reaction Methods 0.000 description 4
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- SLATUJZSZLORHE-UHFFFAOYSA-N 1,22-dibromodocosane Chemical compound BrCCCCCCCCCCCCCCCCCCCCCCBr SLATUJZSZLORHE-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- AYGKJDVBWSEQHQ-UHFFFAOYSA-N 1,20-dibromoicosane Chemical compound BrCCCCCCCCCCCCCCCCCCCCBr AYGKJDVBWSEQHQ-UHFFFAOYSA-N 0.000 description 2
- WRVHHHGSTXFVPY-UHFFFAOYSA-N 1,21-dibromohenicosane Chemical compound BrCCCCCCCCCCCCCCCCCCCCCBr WRVHHHGSTXFVPY-UHFFFAOYSA-N 0.000 description 2
- HJTAVKDWOKPGGJ-UHFFFAOYSA-N 1,23-dibromotricosane Chemical compound BrCCCCCCCCCCCCCCCCCCCCCCCBr HJTAVKDWOKPGGJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PBIMVRFZYCALIB-UHFFFAOYSA-N 1,25-dibromopentacosane Chemical compound BrCCCCCCCCCCCCCCCCCCCCCCCCCBr PBIMVRFZYCALIB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MJRRINQFAYPVEL-UHFFFAOYSA-N docosane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCC(N)CN MJRRINQFAYPVEL-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- CYBQOEBIIKKSSY-UHFFFAOYSA-N henicosane-1,21-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCN CYBQOEBIIKKSSY-UHFFFAOYSA-N 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
- POIZGMCHYSVWDU-UHFFFAOYSA-N icosane-1,20-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCN POIZGMCHYSVWDU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7025506A FR2097517A5 (enExample) | 1970-07-09 | 1970-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2133650A1 true DE2133650A1 (de) | 1972-01-20 |
Family
ID=9058516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712133650 Pending DE2133650A1 (de) | 1970-07-09 | 1971-07-06 | Verfahren zur Herstellung langketü ger alpha omega Diamino alkane |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE769721A (enExample) |
| CH (1) | CH528474A (enExample) |
| DE (1) | DE2133650A1 (enExample) |
| FR (1) | FR2097517A5 (enExample) |
| GB (1) | GB1326985A (enExample) |
| LU (1) | LU63482A1 (enExample) |
| NL (1) | NL7109295A (enExample) |
| SU (1) | SU465781A3 (enExample) |
-
1970
- 1970-07-09 FR FR7025506A patent/FR2097517A5/fr not_active Expired
-
1971
- 1971-07-06 NL NL7109295A patent/NL7109295A/xx unknown
- 1971-07-06 DE DE19712133650 patent/DE2133650A1/de active Pending
- 1971-07-06 CH CH990271A patent/CH528474A/fr not_active IP Right Cessation
- 1971-07-06 LU LU63482D patent/LU63482A1/xx unknown
- 1971-07-07 GB GB3193471A patent/GB1326985A/en not_active Expired
- 1971-07-08 BE BE769721A patent/BE769721A/xx unknown
- 1971-07-09 SU SU1675712A patent/SU465781A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2097517A5 (enExample) | 1972-03-03 |
| BE769721A (fr) | 1971-11-16 |
| CH528474A (fr) | 1972-09-30 |
| SU465781A3 (ru) | 1975-03-30 |
| GB1326985A (en) | 1973-08-15 |
| LU63482A1 (enExample) | 1971-11-15 |
| NL7109295A (enExample) | 1972-01-11 |
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