DE1949296B2 - Verfahren zur Herstellung von 2Äthylhexanol - Google Patents
Verfahren zur Herstellung von 2ÄthylhexanolInfo
- Publication number
- DE1949296B2 DE1949296B2 DE19691949296 DE1949296A DE1949296B2 DE 1949296 B2 DE1949296 B2 DE 1949296B2 DE 19691949296 DE19691949296 DE 19691949296 DE 1949296 A DE1949296 A DE 1949296A DE 1949296 B2 DE1949296 B2 DE 1949296B2
- Authority
- DE
- Germany
- Prior art keywords
- ethylhexanol
- crude
- hydrogenation
- catalysts
- zone
- 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
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- 239000007789 gas Substances 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- -1 2-ethyl Chemical group 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
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 (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE756877D BE756877A (fr) | 1969-09-30 | Procede de preparation du 2-ethylhexanol | |
| DE19691949296 DE1949296B2 (de) | 1969-09-30 | 1969-09-30 | Verfahren zur Herstellung von 2Äthylhexanol |
| FR7033952A FR2062354A5 (enExample) | 1969-09-30 | 1970-09-18 | |
| SE1313970A SE379192B (enExample) | 1969-09-30 | 1970-09-28 | |
| NL7014253A NL7014253A (enExample) | 1969-09-30 | 1970-09-28 | |
| ES384082A ES384082A1 (es) | 1969-09-30 | 1970-09-29 | Procedimiento para la obtencion de 2-etilhexanol. |
| AT877470A AT299141B (de) | 1969-09-30 | 1970-09-29 | Verfahren zur Herstellung von 2-Äthylhexanol |
| GB4616170A GB1315217A (en) | 1969-09-30 | 1970-09-29 | Production of 2-ethylhexanol |
| JP8523570A JPS4911364B1 (enExample) | 1969-09-30 | 1970-09-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691949296 DE1949296B2 (de) | 1969-09-30 | 1969-09-30 | Verfahren zur Herstellung von 2Äthylhexanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1949296A1 DE1949296A1 (de) | 1971-04-08 |
| DE1949296B2 true DE1949296B2 (de) | 1974-08-15 |
Family
ID=5746916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691949296 Pending DE1949296B2 (de) | 1969-09-30 | 1969-09-30 | Verfahren zur Herstellung von 2Äthylhexanol |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4911364B1 (enExample) |
| AT (1) | AT299141B (enExample) |
| BE (1) | BE756877A (enExample) |
| DE (1) | DE1949296B2 (enExample) |
| ES (1) | ES384082A1 (enExample) |
| FR (1) | FR2062354A5 (enExample) |
| GB (1) | GB1315217A (enExample) |
| NL (1) | NL7014253A (enExample) |
| SE (1) | SE379192B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2628987C3 (de) * | 1976-06-28 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von C↓3↓-C↓5↓-Alkanolen |
| DE3264280D1 (en) * | 1981-08-20 | 1985-07-25 | Davy Mckee London | Hydrogenation process |
| JP2724001B2 (ja) * | 1989-01-17 | 1998-03-09 | 三井化学株式会社 | イソプロパノールの製造方法 |
| US5059718A (en) * | 1990-09-24 | 1991-10-22 | Exxon Chemical Patents Inc. | Oxo process for increasing yield of oxo alcohol |
| DE102004029732A1 (de) | 2004-06-21 | 2006-01-19 | Basf Ag | Hilfsmittel enthaltend Cyclohexanpolycarbonsäurederivate |
| EP2496637B1 (de) | 2009-11-03 | 2015-10-07 | Styrolution Europe GmbH | THERMOPLASTISCHE ZUSAMMENSETZUNGEN MIT VERBESSERTER FLIEßFÄHIGKEIT |
| BR112012030589A2 (pt) | 2010-06-01 | 2016-08-16 | Basf Se | composição, processo para produzir composições poliméricas de estireno expansível, e um material de espuma, material de espuma, método para usar um material de espuma e um éster ciclo-hexanocarboxílico |
| GB201102551D0 (en) | 2011-02-14 | 2011-03-30 | Davy Process Techn Ltd | Reactor |
| US11673125B2 (en) | 2016-08-18 | 2023-06-13 | The University Of Chicago | Metal oxide-supported earth-abundant metal catalysts for highly efficient organic transformations |
-
0
- BE BE756877D patent/BE756877A/xx unknown
-
1969
- 1969-09-30 DE DE19691949296 patent/DE1949296B2/de active Pending
-
1970
- 1970-09-18 FR FR7033952A patent/FR2062354A5/fr not_active Expired
- 1970-09-28 SE SE1313970A patent/SE379192B/xx unknown
- 1970-09-28 NL NL7014253A patent/NL7014253A/xx unknown
- 1970-09-29 GB GB4616170A patent/GB1315217A/en not_active Expired
- 1970-09-29 AT AT877470A patent/AT299141B/de not_active IP Right Cessation
- 1970-09-29 ES ES384082A patent/ES384082A1/es not_active Expired
- 1970-09-30 JP JP8523570A patent/JPS4911364B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE379192B (enExample) | 1975-09-29 |
| ES384082A1 (es) | 1972-12-16 |
| NL7014253A (enExample) | 1971-04-01 |
| FR2062354A5 (enExample) | 1971-06-25 |
| DE1949296A1 (de) | 1971-04-08 |
| BE756877A (fr) | 1971-03-30 |
| AT299141B (de) | 1972-06-12 |
| GB1315217A (en) | 1973-05-02 |
| JPS4911364B1 (enExample) | 1974-03-16 |
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