NL8001589A - Werkwijze voor het afscheiden van een kobaltverbinding uit een hydroveresteringsreactiemengsel. - Google Patents
Werkwijze voor het afscheiden van een kobaltverbinding uit een hydroveresteringsreactiemengsel. Download PDFInfo
- Publication number
- NL8001589A NL8001589A NL8001589A NL8001589A NL8001589A NL 8001589 A NL8001589 A NL 8001589A NL 8001589 A NL8001589 A NL 8001589A NL 8001589 A NL8001589 A NL 8001589A NL 8001589 A NL8001589 A NL 8001589A
- Authority
- NL
- Netherlands
- Prior art keywords
- pyridine
- reaction mixture
- picoline
- cobalt
- water
- Prior art date
Links
- 239000011541 reaction mixture Substances 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 40
- 150000001869 cobalt compounds Chemical class 0.000 title claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 132
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 66
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 50
- 229910017052 cobalt Inorganic materials 0.000 claims description 46
- 239000010941 cobalt Substances 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 229910001868 water Inorganic materials 0.000 claims description 35
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 29
- 229930195729 fatty acid Natural products 0.000 claims description 29
- 239000000194 fatty acid Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 150000001336 alkenes Chemical class 0.000 claims description 26
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 25
- 150000005846 sugar alcohols Polymers 0.000 claims description 23
- -1 fatty acid ester Chemical class 0.000 claims description 22
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000012188 paraffin wax Substances 0.000 claims description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 4
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 claims description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims description 2
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 2
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 claims description 2
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 claims description 2
- OHFQAZVYTLCHMK-UHFFFAOYSA-N 4-ethenyl-3-methylpyridine Chemical compound CC1=CN=CC=C1C=C OHFQAZVYTLCHMK-UHFFFAOYSA-N 0.000 claims description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 2
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 230000029087 digestion Effects 0.000 claims 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- PBHMHFVAFKKQIA-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] heptanoate Chemical compound CCCCCCC(=O)OCC(CO)(CO)CO PBHMHFVAFKKQIA-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 12
- FDPHDGUADUFPHZ-UHFFFAOYSA-L cobalt(2+);heptanoate Chemical compound [Co+2].CCCCCCC([O-])=O.CCCCCCC([O-])=O FDPHDGUADUFPHZ-UHFFFAOYSA-L 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 8
- 230000032050 esterification Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001868 cobalt Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OPTYCEAUVSDMAT-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) heptanoate Chemical compound CCCCCCC(=O)OCC(C)(C)CO OPTYCEAUVSDMAT-UHFFFAOYSA-N 0.000 description 2
- JEEGBFDQANTYDD-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)(C)CO JEEGBFDQANTYDD-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- ZEUMJGYFKUTAKD-UHFFFAOYSA-L cobalt(2+);nonanoate Chemical compound [Co+2].CCCCCCCCC([O-])=O.CCCCCCCCC([O-])=O ZEUMJGYFKUTAKD-UHFFFAOYSA-L 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4947579A JPS55141440A (en) | 1979-04-21 | 1979-04-21 | Separation of cobalt component from liquid produced by hydroesterification reaction |
| JP4947579 | 1979-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8001589A true NL8001589A (nl) | 1980-10-23 |
Family
ID=12832172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001589A NL8001589A (nl) | 1979-04-21 | 1980-03-18 | Werkwijze voor het afscheiden van een kobaltverbinding uit een hydroveresteringsreactiemengsel. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4322314A (en, 2012) |
| JP (1) | JPS55141440A (en, 2012) |
| CA (1) | CA1135716A (en, 2012) |
| DE (1) | DE3011687C2 (en, 2012) |
| FR (1) | FR2454444B1 (en, 2012) |
| GB (1) | GB2047246B (en, 2012) |
| NL (1) | NL8001589A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7582226B2 (en) * | 2000-12-22 | 2009-09-01 | Exxonmobil Chemical Patents Inc. | Ester-containing fluid compositions |
| WO2002072521A1 (fr) * | 2001-03-08 | 2002-09-19 | Mitsubishi Chemical Corporation | Procede relatif a l'elaboration d'aldehyde |
| RU2188058C1 (ru) * | 2001-04-17 | 2002-08-27 | Иванов Владимир Михайлович | СПОСОБ РАЗДЕЛЕНИЯ АЗЕОТРОПНОЙ СМЕСИ α-ПИКОЛИН - ВОДА |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2047717A5 (en) * | 1969-05-14 | 1971-03-12 | Ici Ltd | Esters from olefins using metal carbonyl - catalysts |
| US3856832A (en) * | 1970-12-07 | 1974-12-24 | Corp Ethyl | Process for recovering cobalt catalyst in an active form from a hydroesterification reaction mixture |
| JPS5062888A (en, 2012) * | 1973-10-06 | 1975-05-29 | ||
| JPS5533380B2 (en, 2012) * | 1973-10-06 | 1980-08-30 | ||
| JPS5239810B2 (en, 2012) * | 1974-02-09 | 1977-10-07 | ||
| US4041057A (en) * | 1975-07-02 | 1977-08-09 | Ethyl Corporation | Hydroesterification process |
-
1979
- 1979-04-21 JP JP4947579A patent/JPS55141440A/ja active Granted
-
1980
- 1980-03-07 US US06/128,149 patent/US4322314A/en not_active Expired - Lifetime
- 1980-03-18 NL NL8001589A patent/NL8001589A/nl not_active Application Discontinuation
- 1980-03-26 DE DE3011687A patent/DE3011687C2/de not_active Expired
- 1980-03-26 FR FR8006727A patent/FR2454444B1/fr not_active Expired
- 1980-03-27 CA CA000348786A patent/CA1135716A/en not_active Expired
- 1980-03-28 GB GB8010530A patent/GB2047246B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3011687A1 (de) | 1980-10-23 |
| FR2454444A1 (fr) | 1980-11-14 |
| DE3011687C2 (de) | 1986-10-30 |
| JPS6228773B2 (en, 2012) | 1987-06-23 |
| FR2454444B1 (fr) | 1985-06-07 |
| US4322314A (en) | 1982-03-30 |
| GB2047246A (en) | 1980-11-26 |
| CA1135716A (en) | 1982-11-16 |
| GB2047246B (en) | 1983-04-20 |
| JPS55141440A (en) | 1980-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1B | A search report has been drawn up | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: LION CORPORATION |
|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |