CH508582A - Verfahren zur Herstellung von Diaminen - Google Patents
Verfahren zur Herstellung von DiaminenInfo
- Publication number
- CH508582A CH508582A CH581067A CH581067A CH508582A CH 508582 A CH508582 A CH 508582A CH 581067 A CH581067 A CH 581067A CH 581067 A CH581067 A CH 581067A CH 508582 A CH508582 A CH 508582A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogenation
- ammonia
- diamines
- dimethyl
- hydrogen
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 41
- 229910021529 ammonia Inorganic materials 0.000 title claims abstract description 30
- 150000004985 diamines Chemical class 0.000 title claims abstract description 26
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- -1 4,4-dimethyl-7-phenyl-1,7-diaminoheptane Chemical compound 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- GYPBUOTWHLDLNI-UHFFFAOYSA-N 4,4,6-trimethyloctane-1,7-diamine Chemical compound NCCCC(CC(C(C)N)C)(C)C GYPBUOTWHLDLNI-UHFFFAOYSA-N 0.000 description 3
- FWUMWFWUGMEBSG-UHFFFAOYSA-N 4,4-dimethyloctane-1,7-diamine Chemical compound CC(N)CCC(C)(C)CCCN FWUMWFWUGMEBSG-UHFFFAOYSA-N 0.000 description 3
- MIZASJHAUWNJOU-UHFFFAOYSA-N C(#N)CCC(CC(=C)C)(C)C Chemical compound C(#N)CCC(CC(=C)C)(C)C MIZASJHAUWNJOU-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZWIBGDOHXGXHEV-UHFFFAOYSA-N 4,4-dimethylheptane-1,7-diamine Chemical compound NCCCC(C)(C)CCCN ZWIBGDOHXGXHEV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- BJSDWKGJUKJAPA-UHFFFAOYSA-N NCCCC(CCC(C(C)C)N)(C)C Chemical compound NCCCC(CCC(C(C)C)N)(C)C BJSDWKGJUKJAPA-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CWNRYVQFAMHXLM-UHFFFAOYSA-N 2-formylbutanenitrile Chemical compound CCC(C=O)C#N CWNRYVQFAMHXLM-UHFFFAOYSA-N 0.000 description 1
- ZLKUKJGDRJMIEA-UHFFFAOYSA-N 4,4-dimethyl-5-(2-oxocyclohexylidene)pentanenitrile Chemical compound CC(C=C1C(CCCC1)=O)(CCC#N)C ZLKUKJGDRJMIEA-UHFFFAOYSA-N 0.000 description 1
- FNEARBHZFXEPFD-UHFFFAOYSA-N 5-oxopentanenitrile Chemical compound O=CCCCC#N FNEARBHZFXEPFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- IZKZIDXHCDIZKY-UHFFFAOYSA-N heptane-1,1-diamine Chemical compound CCCCCCC(N)N IZKZIDXHCDIZKY-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UNEXJVCWJSHFNN-UHFFFAOYSA-N n,n,n',n'-tetraethylmethanediamine Chemical compound CCN(CC)CN(CC)CC UNEXJVCWJSHFNN-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/26—Amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| DED0049966 | 1966-04-28 | ||
| DED0052547 | 1967-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH508582A true CH508582A (de) | 1971-06-15 |
Family
ID=25972343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH581067A CH508582A (de) | 1966-04-28 | 1967-04-24 | Verfahren zur Herstellung von Diaminen |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT284805B (2) |
| BE (1) | BE697697A (2) |
| CH (1) | CH508582A (2) |
| DE (2) | DE1543516A1 (2) |
| GB (1) | GB1146567A (2) |
| NL (2) | NL6705968A (2) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841585C3 (de) * | 1978-09-25 | 1987-07-30 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen |
| DE2902172C2 (de) * | 1979-01-20 | 1984-05-10 | UOP Inc., 60016 Des Plaines, Ill. | Verfahren zur Herstellung eines N,N'-Dialkylphenylendiamins |
-
1966
- 1966-04-28 DE DE19661543516 patent/DE1543516A1/de not_active Withdrawn
-
1967
- 1967-03-17 DE DE19671593820 patent/DE1593820A1/de not_active Ceased
- 1967-04-24 CH CH581067A patent/CH508582A/de not_active IP Right Cessation
- 1967-04-27 NL NL6705968A patent/NL6705968A/xx unknown
- 1967-04-27 GB GB1956167A patent/GB1146567A/en not_active Expired
- 1967-04-27 BE BE697697D patent/BE697697A/xx unknown
- 1967-04-27 AT AT397267A patent/AT284805B/de not_active IP Right Cessation
-
1978
- 1978-06-07 NL NL7806214A patent/NL7806214A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1146567A (en) | 1969-03-26 |
| NL6705968A (2) | 1967-10-30 |
| BE697697A (2) | 1967-10-02 |
| DE1593820A1 (de) | 1970-12-10 |
| NL7806214A (nl) | 1978-11-30 |
| DE1543516A1 (de) | 1969-10-23 |
| AT284805B (de) | 1970-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH429705A (de) | Verfahren zur Herstellung von Gemischen aus Aminoalkoholen und Diaminen | |
| DE3021955A1 (de) | Verfahren zur herstellung primaerer mono- und diamine aus oxoverbindungen | |
| DE2907869A1 (de) | Verfahren zum herstellen aliphatischer amine | |
| DE3822038A1 (de) | Verfahren zur herstellung von 3(4),8(9)-bis-(aminomethyl)-tricyclo (5.2.1.0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decan | |
| DE69014336T2 (de) | Herstellung von Polyaminen. | |
| DE4446894A1 (de) | Verfahren zur Herstellung von aliphatischen alpha,omega-Aminonitrilen | |
| DE2551055A1 (de) | Verfahren zur herstellung von 1,3- oder 1,4-bis-(aminomethyl)-cyclohexan | |
| DE69010049T2 (de) | Koproduktion von Propandiamin und alkylierten Aminopropylaminen. | |
| DE2626676A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| CH508582A (de) | Verfahren zur Herstellung von Diaminen | |
| EP0452693B1 (de) | Verfahren zur Herstellung von 2,2-disubstituierten Pentan-1,5-diaminen | |
| DE2630562C2 (de) | Verfahren zur katalytischen Hydrierung von Perfluoralkyl-substituierten Anilinen | |
| DE2626675A1 (de) | Verfahren zur herstellung von 2-pyrrolidon | |
| DE1068719B (de) | Verfahren zur Herstellung von Pentamethylendiamin und Piperidin | |
| DE3544510A1 (de) | Verfahren zur herstellung aliphatischer tertiaerer amine | |
| DE2655794A1 (de) | Verfahren zur herstellung von aethylencyanhydrin | |
| DE2430038A1 (de) | Verfahren zur herstellung von acetoxybutanolen | |
| AT237592B (de) | Verfahren zur Herstellung von neuen Cyclohexanderivaten | |
| DE1908466C3 (de) | Aminonitrile und Verfahren zu ihrer Herstellung | |
| DE1618295C3 (de) | Verfahren zur Herstellung von Ketonitrilen | |
| DE4210311A1 (de) | Verfahren zur Herstellung von Aminen aus Azinen | |
| DE875357C (de) | Verfahren zur Herstellung von Polyaminen | |
| DE2940256A1 (de) | N,n-dimethyl-n'-(beta)-hydroxyethyl-propylendiamin und verfahren zu seiner herstellung | |
| DE2319360A1 (de) | Verfahren zur herstellung von epsilonaminocapronsaeureamid | |
| DE2715518C2 (2) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |