DE1906850C - - Google Patents
Info
- Publication number
- DE1906850C DE1906850C DE19691906850 DE1906850A DE1906850C DE 1906850 C DE1906850 C DE 1906850C DE 19691906850 DE19691906850 DE 19691906850 DE 1906850 A DE1906850 A DE 1906850A DE 1906850 C DE1906850 C DE 1906850C
- Authority
- DE
- Germany
- Prior art keywords
- hydroformylation
- cobalt
- butanals
- propylene
- synthesis
- 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
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 19
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 229910017052 cobalt Inorganic materials 0.000 claims description 17
- 239000010941 cobalt Substances 0.000 claims description 17
- 238000007037 hydroformylation reaction Methods 0.000 claims description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 5
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical class CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims description 4
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkaline earth metal salt Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- VDHBXQMYKGNZRP-UHFFFAOYSA-N 1-(2-methylpropoxy)butane Chemical compound CCCCOCC(C)C VDHBXQMYKGNZRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 235000011126 aluminium potassium sulphate Nutrition 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000022244 formylation Effects 0.000 claims description 2
- 238000006170 formylation reaction Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940050271 potassium alum Drugs 0.000 claims description 2
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 10
- 238000003786 synthesis reaction Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 238000004064 recycling Methods 0.000 claims 2
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 claims 1
- 229920000049 Carbon (fiber) Polymers 0.000 claims 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims 1
- CODVACFVSVNQPY-UHFFFAOYSA-N [Co].[C] Chemical compound [Co].[C] CODVACFVSVNQPY-UHFFFAOYSA-N 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000004917 carbon fiber Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- 238000009826 distribution Methods 0.000 claims 1
- 230000002349 favourable effect Effects 0.000 claims 1
- 150000004675 formic acid derivatives Chemical class 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 230000017525 heat dissipation Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910000358 iron sulfate Inorganic materials 0.000 claims 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000010517 secondary reaction Methods 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 claims 1
- 229910003452 thorium oxide Inorganic materials 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 150000003738 xylenes Chemical class 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- 239000006286 aqueous extract Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR140024 | 1968-02-15 | ||
| FR140024 | 1968-02-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1906850A1 DE1906850A1 (de) | 1969-11-27 |
| DE1906850C true DE1906850C (enrdf_load_stackoverflow) | 1973-06-20 |
Family
ID=8646039
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691906850 Granted DE1906850A1 (de) | 1968-02-15 | 1969-02-12 | Verfahren zur Herstellung von Butanalen durch Oxosynthese und deren Verwendung fuer die Herstellung von AEthylhexanol |
| DE19691966388 Pending DE1966388A1 (de) | 1968-02-15 | 1969-02-12 | Verfahren zur Herstellung von 2-AEthylhexanol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691966388 Pending DE1966388A1 (de) | 1968-02-15 | 1969-02-12 | Verfahren zur Herstellung von 2-AEthylhexanol |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3763247A (enrdf_load_stackoverflow) |
| AT (2) | AT295484B (enrdf_load_stackoverflow) |
| BE (1) | BE727913A (enrdf_load_stackoverflow) |
| BR (1) | BR6906373D0 (enrdf_load_stackoverflow) |
| DE (2) | DE1906850A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1563043A (enrdf_load_stackoverflow) |
| GB (1) | GB1228348A (enrdf_load_stackoverflow) |
| NL (1) | NL141852B (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4214109A (en) * | 1979-01-29 | 1980-07-22 | Conoco, Inc. | Polymer bound (pentahaptocyclopentadienyl)biscarbonyl rhodium hydroformylation catalyst |
| US4426542A (en) * | 1981-04-22 | 1984-01-17 | Monsanto Company | Synthesis of plasticizer and detergent alcohols |
| US4598162A (en) * | 1981-06-11 | 1986-07-01 | Monsanto Company | Detergent range aldehyde and alcohol mixtures and derivatives, and process therefor |
| US4518809A (en) * | 1981-06-11 | 1985-05-21 | Monsanto Company | Preparation of pentyl nonanols |
| DE3530839A1 (de) * | 1985-08-29 | 1987-03-05 | Ruhrchemie Ag | Verfahren zur herstellung von 2-ethylhexanol |
| US7649112B2 (en) * | 2005-07-25 | 2010-01-19 | Saudi Basic Industries Corporation | Integrated plant for producing 2-ethyl-hexanol and methacrylic acid and a method based thereon |
| US20100226838A1 (en) * | 2007-05-30 | 2010-09-09 | Anand Kumar Bachasingh | Process for the removal of catalyst degradation products |
| DE102009045139A1 (de) | 2009-09-30 | 2011-03-31 | Evonik Oxeno Gmbh | Herstellung von alpha,beta-ungesättigten Aldehyden mittels einer Reaktionsmischpumpe |
| DE102011012846B4 (de) | 2011-03-03 | 2016-08-18 | Oxea Gmbh | Verfahren zur Durchführung von mehrphasigen Aldolkondensationsreaktionen zu gemischten α,β-ungesättigten Aldehyden |
| WO2014178031A1 (en) | 2013-05-03 | 2014-11-06 | Saudi Basic Industries Corporation | Integrated process for simultaneous production of oxo-alcohols and plasticizers |
| US20250196020A1 (en) * | 2023-12-17 | 2025-06-19 | Tianjin Shenlan Chemical Technology Co., Ltd | Equipment for production of butanol and octanol and triple-effect distillation method |
-
1968
- 1968-02-15 FR FR140024A patent/FR1563043A/fr not_active Expired
-
1969
- 1969-02-04 BE BE727913D patent/BE727913A/xx not_active IP Right Cessation
- 1969-02-12 GB GB1228348D patent/GB1228348A/en not_active Expired
- 1969-02-12 DE DE19691906850 patent/DE1906850A1/de active Granted
- 1969-02-12 DE DE19691966388 patent/DE1966388A1/de active Pending
- 1969-02-13 NL NL696902287A patent/NL141852B/xx not_active IP Right Cessation
- 1969-02-13 BR BR206373/69A patent/BR6906373D0/pt unknown
- 1969-02-14 AT AT153569A patent/AT295484B/de active
- 1969-02-14 US US00799279A patent/US3763247A/en not_active Expired - Lifetime
- 1969-02-14 AT AT6707/70A patent/AT304461B/de not_active IP Right Cessation
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