DE2504005A1 - Verfahren zur herstellung von polyolestern von carbonsaeuren - Google Patents
Verfahren zur herstellung von polyolestern von carbonsaeurenInfo
- Publication number
- DE2504005A1 DE2504005A1 DE19752504005 DE2504005A DE2504005A1 DE 2504005 A1 DE2504005 A1 DE 2504005A1 DE 19752504005 DE19752504005 DE 19752504005 DE 2504005 A DE2504005 A DE 2504005A DE 2504005 A1 DE2504005 A1 DE 2504005A1
- Authority
- DE
- Germany
- Prior art keywords
- cobalt
- reaction
- carbon monoxide
- vinyl pyridine
- carbonyl compound
- 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.)
- Ceased
Links
- -1 polyol carboxylate esters Chemical class 0.000 title claims abstract description 26
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 22
- 229920005862 polyol Polymers 0.000 title claims abstract description 12
- 150000005846 sugar alcohols Polymers 0.000 title claims abstract description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 title claims description 27
- 238000006243 chemical reaction Methods 0.000 title claims description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 33
- 229910017052 cobalt Inorganic materials 0.000 claims description 28
- 239000010941 cobalt Substances 0.000 claims description 28
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-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
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 claims description 2
- 229910021446 cobalt carbonate Inorganic materials 0.000 claims description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 2
- 229910000428 cobalt oxide Inorganic materials 0.000 claims description 2
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 claims description 2
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 claims description 2
- MULYSYXKGICWJF-UHFFFAOYSA-L cobalt(2+);oxalate Chemical compound [Co+2].[O-]C(=O)C([O-])=O MULYSYXKGICWJF-UHFFFAOYSA-L 0.000 claims description 2
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 claims description 2
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-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
- VXEXDVFIZKWHIB-UHFFFAOYSA-N 2-ethenylpyridine Chemical compound C=CC1=CC=CC=N1.C=CC1=CC=CC=N1 VXEXDVFIZKWHIB-UHFFFAOYSA-N 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 239000000314 lubricant Substances 0.000 abstract description 4
- 239000004014 plasticizer Substances 0.000 abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000000080 wetting agent Substances 0.000 abstract description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 150000004665 fatty acids Chemical class 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 13
- 238000005886 esterification reaction Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 230000032050 esterification Effects 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000005691 triesters Chemical class 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000009365 direct transmission Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229910052683 pyrite Inorganic materials 0.000 description 1
- 239000011028 pyrite Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1666174A JPS5331128B2 (enrdf_load_stackoverflow) | 1974-02-09 | 1974-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2504005A1 true DE2504005A1 (de) | 1975-08-21 |
Family
ID=11922508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504005 Ceased DE2504005A1 (de) | 1974-02-09 | 1975-01-31 | Verfahren zur herstellung von polyolestern von carbonsaeuren |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5331128B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2504005A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7500989A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244882A (en) * | 1978-06-22 | 1981-01-13 | The Lion Fat & Oil Co., Ltd. | Process for continuous production of full esters of polyols |
| US4256909A (en) * | 1978-08-30 | 1981-03-17 | Basf Aktiengesellschaft | Preparation of dimethyl butanedicarboxylates |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5928659U (ja) * | 1982-08-18 | 1984-02-22 | 小松ゼノア株式会社 | エンジン |
| JPS5928660U (ja) * | 1982-08-18 | 1984-02-22 | 小松ゼノア株式会社 | 気化器用の取付中間体 |
| JPS63138458U (enrdf_load_stackoverflow) * | 1987-02-28 | 1988-09-12 | ||
| CN115569669B (zh) * | 2021-06-21 | 2024-03-08 | 惠生工程（中国）有限公司 | 用于环氧乙烷氢甲酯化反应的固体多相催化剂及制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5121633B2 (enrdf_load_stackoverflow) * | 1972-11-25 | 1976-07-03 | ||
| JPS5045798A (enrdf_load_stackoverflow) * | 1973-08-29 | 1975-04-24 |
-
1974
- 1974-02-09 JP JP1666174A patent/JPS5331128B2/ja not_active Expired
-
1975
- 1975-01-28 NL NL7500989A patent/NL7500989A/xx not_active Application Discontinuation
- 1975-01-31 DE DE19752504005 patent/DE2504005A1/de not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244882A (en) * | 1978-06-22 | 1981-01-13 | The Lion Fat & Oil Co., Ltd. | Process for continuous production of full esters of polyols |
| US4256909A (en) * | 1978-08-30 | 1981-03-17 | Basf Aktiengesellschaft | Preparation of dimethyl butanedicarboxylates |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7500989A (nl) | 1975-08-12 |
| JPS5331128B2 (enrdf_load_stackoverflow) | 1978-08-31 |
| JPS50108211A (enrdf_load_stackoverflow) | 1975-08-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1293735B (de) | Verfahren zur Herstellung von Aldehyden und Alkoholen | |
| DE3232557C2 (enrdf_load_stackoverflow) | ||
| US3980683A (en) | Process for carboxylation of olefins | |
| DE2462444B2 (de) | Verfahren zur Herstellung von Monocarbonsäureester« | |
| DE69328591T2 (de) | Hydroformylierungsverfahren mit einem bimetallischen Katalysator | |
| DE2531070B2 (de) | Verfahren zur Herstellung von einwertigen und mehrwertigen Alkoholen, deren Ester und Äther sowie Oligomeren | |
| EP0010581B1 (de) | Verfahren zur Herstellung von Butandicarbonsäuredimethylestern | |
| DE2504005A1 (de) | Verfahren zur herstellung von polyolestern von carbonsaeuren | |
| DE2447069C2 (de) | Verfahren zur Herstellung von Carbonsäureestern | |
| DE2361402C3 (de) | Verfahren zur Herstellung von PoIyolestern von Carbonsäuren | |
| DE3331929C2 (enrdf_load_stackoverflow) | ||
| EP0011842B1 (de) | Verfahren zum Abbau von Ameisensäureestern | |
| DE2404955C2 (de) | Verfahren zur Herstellung von Polyolestern von Carbonsäuren | |
| DE2513838C2 (de) | Verfahren zur Herstellung von Polyolestergemischen | |
| DE3725241A1 (de) | Verfahren zur herstellung von pentensaeurealkylestern | |
| DE2003371C3 (de) | Verfahren zur Disproportionierung äthylenisch ungesättigter Verbindungen | |
| US3974194A (en) | Method of separating cobalt catalyst from a liquid polyol ester product | |
| DE2823309A1 (de) | Verfahren zur herstellung von aethanol | |
| EP0352641B1 (de) | Verfahren zur Herstellung von Pentensäurealkylestern | |
| DE1643145C3 (de) | Verfahren zur Herstellung von E-Caprolacton | |
| DE3201665A1 (de) | Verfahren zur herstellung von ethanol und n-propanol aus methanol und synthesegas | |
| DE3034019C2 (de) | Verfahren zur gleichzeitigen Herstellung von Estern von Alkanolen und vicinalen Glykolen | |
| DE2714564A1 (de) | Verfahren zur herstellung von cyclischen estern der undecandisaeure | |
| DE3221172A1 (de) | Verfahren zur herstellung von carbonsaeuren und estern | |
| DE3243386A1 (de) | Verfahren zur herstellung von aethylenglykol und niederen einwertigen alkoholen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8127 | New person/name/address of the applicant |
Owner name: LION CORP., TOKYO, JP |
|
| 8131 | Rejection |