DE2205958C3 - Verfahren zur Reinigung tertiärer aliphatischer Amine - Google Patents
Verfahren zur Reinigung tertiärer aliphatischer AmineInfo
- Publication number
- DE2205958C3 DE2205958C3 DE2205958A DE2205958A DE2205958C3 DE 2205958 C3 DE2205958 C3 DE 2205958C3 DE 2205958 A DE2205958 A DE 2205958A DE 2205958 A DE2205958 A DE 2205958A DE 2205958 C3 DE2205958 C3 DE 2205958C3
- Authority
- DE
- Germany
- Prior art keywords
- tertiary
- amines
- distillation
- catalyst
- hydrogenation
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 150000003510 tertiary aliphatic amines Chemical class 0.000 title claims 2
- 238000000746 purification Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000003512 tertiary amines Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 150000003138 primary alcohols Chemical class 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000005576 amination reaction Methods 0.000 claims description 4
- 230000009183 running Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims 4
- 239000005909 Kieselgur Substances 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 150000002739 metals Chemical class 0.000 claims 3
- 230000000737 periodic effect Effects 0.000 claims 3
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 150000001241 acetals Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 238000001577 simple distillation Methods 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 2
- 239000004440 Isodecyl alcohol Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 description 1
- YGLJGOMFUHQSBN-UHFFFAOYSA-N 7-methyl-n,n-bis(7-methyloctyl)octan-1-amine Chemical compound CC(C)CCCCCCN(CCCCCCC(C)C)CCCCCCC(C)C YGLJGOMFUHQSBN-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- 239000004439 Isononyl alcohol Substances 0.000 description 1
- 235000003407 Sigesbeckia orientalis Nutrition 0.000 description 1
- 240000003801 Sigesbeckia orientalis Species 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2205958A DE2205958C3 (de) | 1972-02-09 | 1972-02-09 | Verfahren zur Reinigung tertiärer aliphatischer Amine |
| US326182A US3875235A (en) | 1972-02-09 | 1973-01-24 | Process for the preparation of tertiary amines of high purity |
| SU1878317A SU448637A3 (ru) | 1972-02-09 | 1973-01-31 | Способ получени чистых третичных аминов |
| DD168638A DD105205A5 (enExample) | 1972-02-09 | 1973-02-02 | |
| ZA730767A ZA73767B (en) | 1972-02-09 | 1973-02-02 | Process for the preparation of tertiary amines of high purity |
| CA163,213A CA991581A (en) | 1972-02-09 | 1973-02-08 | Process for the preparation of pure tertiary amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2205958A DE2205958C3 (de) | 1972-02-09 | 1972-02-09 | Verfahren zur Reinigung tertiärer aliphatischer Amine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2205958A1 DE2205958A1 (de) | 1973-09-06 |
| DE2205958B2 DE2205958B2 (de) | 1974-01-10 |
| DE2205958C3 true DE2205958C3 (de) | 1974-08-15 |
Family
ID=5835417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2205958A Expired DE2205958C3 (de) | 1972-02-09 | 1972-02-09 | Verfahren zur Reinigung tertiärer aliphatischer Amine |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3875235A (enExample) |
| CA (1) | CA991581A (enExample) |
| DD (1) | DD105205A5 (enExample) |
| DE (1) | DE2205958C3 (enExample) |
| SU (1) | SU448637A3 (enExample) |
| ZA (1) | ZA73767B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082805A (en) * | 1974-11-01 | 1978-04-04 | Mobil Oil Corporation | Production of aliphatic amines utilizing a crystalline aluminosilicate catalyst of zsm-5, zsm-11 or zsm-21 |
| US4922024A (en) * | 1988-04-14 | 1990-05-01 | The Dow Chemical Company | Amination process employing group vib metal catalysts |
| US5030740A (en) * | 1988-10-14 | 1991-07-09 | The Dow Chemical Company | Process for preparing linearly-extended polyalkylenepolyamines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL248643A (enExample) * | 1959-02-27 |
-
1972
- 1972-02-09 DE DE2205958A patent/DE2205958C3/de not_active Expired
-
1973
- 1973-01-24 US US326182A patent/US3875235A/en not_active Expired - Lifetime
- 1973-01-31 SU SU1878317A patent/SU448637A3/ru active
- 1973-02-02 ZA ZA730767A patent/ZA73767B/xx unknown
- 1973-02-02 DD DD168638A patent/DD105205A5/xx unknown
- 1973-02-08 CA CA163,213A patent/CA991581A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA73767B (en) | 1973-10-31 |
| DD105205A5 (enExample) | 1974-04-12 |
| DE2205958B2 (de) | 1974-01-10 |
| SU448637A3 (ru) | 1974-10-30 |
| CA991581A (en) | 1976-06-22 |
| US3875235A (en) | 1975-04-01 |
| DE2205958A1 (de) | 1973-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |