CA1056403A - Process for preventing the formation of an emulsion when working up reaction mixtures containing butyraldehydes and cobalt - Google Patents
Process for preventing the formation of an emulsion when working up reaction mixtures containing butyraldehydes and cobaltInfo
- Publication number
- CA1056403A CA1056403A CA218,728A CA218728A CA1056403A CA 1056403 A CA1056403 A CA 1056403A CA 218728 A CA218728 A CA 218728A CA 1056403 A CA1056403 A CA 1056403A
- Authority
- CA
- Canada
- Prior art keywords
- cobalt
- molecular oxygen
- weight
- oxo
- reaction mixture
- 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
- 229910017052 cobalt Inorganic materials 0.000 title claims abstract description 41
- 239000010941 cobalt Substances 0.000 title claims abstract description 41
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 23
- 239000000839 emulsion Substances 0.000 title claims abstract description 11
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 19
- 239000007789 gas Substances 0.000 claims abstract description 12
- 239000011260 aqueous acid Substances 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 8
- 239000008346 aqueous phase Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims 1
- 229960003903 oxygen Drugs 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001868 cobalt Chemical class 0.000 description 3
- WHWBTOCNUBAGRL-UHFFFAOYSA-N cobalt;formaldehyde Chemical compound [Co].O=C WHWBTOCNUBAGRL-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- PFQLIVQUKOIJJD-UHFFFAOYSA-L cobalt(ii) formate Chemical compound [Co+2].[O-]C=O.[O-]C=O PFQLIVQUKOIJJD-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2404855A DE2404855C3 (de) | 1974-02-01 | 1974-02-01 | Verfahren zur Verhinderung von Emulsionsbildung bei der Aufbereitung von Butyraldehyden und Kobalt enthaltenden Reaktionsgemischen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1056403A true CA1056403A (en) | 1979-06-12 |
Family
ID=5906354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,728A Expired CA1056403A (en) | 1974-02-01 | 1975-01-27 | Process for preventing the formation of an emulsion when working up reaction mixtures containing butyraldehydes and cobalt |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3932523A (https=) |
| JP (1) | JPS50106911A (https=) |
| AT (1) | AT336559B (https=) |
| BE (1) | BE824480A (https=) |
| CA (1) | CA1056403A (https=) |
| DE (1) | DE2404855C3 (https=) |
| ES (1) | ES434311A1 (https=) |
| FR (1) | FR2259805A1 (https=) |
| IT (1) | IT1031150B (https=) |
| SE (1) | SE7500972L (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4388476A (en) * | 1981-05-01 | 1983-06-14 | Eastman Kodak Company | Hydroformylation process with rhodium catalyst and oxygen stabilization thereof |
| DE3320648A1 (de) * | 1983-06-08 | 1984-12-13 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von reinem n-butyraldehyd |
| US4822917A (en) * | 1986-12-23 | 1989-04-18 | Mitsubishi Chemical Industries Limited | Process for the hydroformylation of an olefin |
| DE4316180A1 (de) * | 1992-09-16 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| ES2158507T3 (es) | 1996-09-20 | 2001-09-01 | Basf Ag | Procedimiento para el hidroformilacion. |
| DE19939491A1 (de) | 1999-08-20 | 2001-02-22 | Basf Ag | Kontinuierliches Verfahren zur Hydroformylierung von Olefinen mit 6 bis 20 Kohlenstoffatomen |
| EP2136917B1 (en) * | 2007-04-18 | 2011-08-17 | ExxonMobil Chemical Patents Inc. | Improvements in oxidative demetalling |
| JP5859563B2 (ja) | 2010-12-23 | 2016-02-10 | スタイロリューション・ヨーロッパ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 熱可塑性エラストマー組成物及びその製造方法 |
| TWI654177B (zh) | 2013-10-31 | 2019-03-21 | 德商巴斯夫歐洲公司 | 製備羧酸酯的方法及其作爲塑化劑的用途 |
| US9115069B2 (en) | 2013-11-18 | 2015-08-25 | Basf Se | Process for hydroformylation of olefins |
| EP3077453B1 (de) | 2013-12-06 | 2018-03-28 | Basf Se | Weichmacher-zusammensetzung, die tetrahydrofuranderivate und 1,2-cyclohexandicarbonsäureester enthält |
| RU2016132589A (ru) | 2014-01-09 | 2018-02-12 | Басф Се | Композиция пластификатора, которая содержит производные фурана и сложные эфиры 1,2-циклогександикарбоновой кислоты |
| CN106232571B (zh) | 2014-04-22 | 2019-05-28 | 巴斯夫欧洲公司 | 在离子液体和酸性酯化催化剂的存在下制备羧酸酯的方法及其作为塑化剂的用途 |
| DE102015207291A1 (de) | 2014-04-24 | 2016-03-10 | Basf Se | Weichmacher-Zusammensetzung, die Furanderivate und 1,2-Cyclohexandicarbonsäureester enthält |
| TW201605945A (zh) | 2014-07-08 | 2016-02-16 | 巴斯夫歐洲公司 | 包含二羧酸的酯及１，２－環己烷二羧酸的酯之模製化合物 |
| TW201609628A (zh) | 2014-07-08 | 2016-03-16 | 巴斯夫歐洲公司 | 包含脂族二羧酸二酯及對苯二甲酸二烷基酯之塑化劑組成物 |
| TWI706979B (zh) | 2014-08-19 | 2020-10-11 | 德商巴斯夫歐洲公司 | 包含聚合二羧酸酯的塑化劑組成物 |
| TWI686444B (zh) | 2014-09-04 | 2020-03-01 | 德商巴斯夫歐洲公司 | 包含聚合二羧酸酯的塑化劑組成物 |
| TW201619120A (zh) | 2014-10-09 | 2016-06-01 | 巴斯夫歐洲公司 | 包含飽和二羧酸之環烷基酯及對苯二甲酯之塑化劑組成物 |
| TW201619119A (zh) | 2014-10-09 | 2016-06-01 | 巴斯夫歐洲公司 | 包含飽和二羧酸之環烷基酯及１，２－環己烷二羧酸酯的塑化劑組成物 |
| EP3250635B1 (de) | 2015-01-30 | 2018-10-24 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und terephthalsäuredialkylester enthält |
| PL3356456T3 (pl) | 2015-09-30 | 2019-11-29 | Basf Se | Kompozycja plastyfikatora zawierająca polimerowe estry kwasu dikarboksylowego i estry dialkilowe kwasu tereftalowego |
| CA2999998A1 (en) | 2015-09-30 | 2017-04-06 | Basf Se | Plasticizer composition containing polymeric dicarboxylic acid esters and 1,2-cyclohexane dicarboxylic acid esters |
| CA2999936A1 (en) | 2015-09-30 | 2017-04-06 | Basf Se | Plasticizer composition containing polymeric dicarboxylic acid esters and dicarboxylic acid diesters |
| US10550242B2 (en) | 2016-01-20 | 2020-02-04 | Basf Se | Plasticiser composition containing aliphatic dicarboxylic acid esters and diesters selected from 1,2-cyclohexane dicarboxylic acid esters and terephthalic acid esters |
| EP3686238A1 (de) | 2016-03-23 | 2020-07-29 | Basf Se | Polymer-zusammensetzung, enthaltend einen cycloalkyl-alkyl-dicarbonsäurediester als weichmacher |
| WO2018024591A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| WO2018024594A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| WO2018024597A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| WO2019185409A1 (de) | 2018-03-29 | 2019-10-03 | Basf Se | Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung |
| EP3747860B1 (de) | 2019-06-04 | 2023-07-26 | Basf Se | Neue weichmacher auf cyclohexanon-basis |
| WO2024133358A1 (de) | 2022-12-21 | 2024-06-27 | Basf Se | Weichmacher-verbindung |
| WO2024153687A1 (de) | 2023-01-19 | 2024-07-25 | Basf Se | Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern |
| DE112024002592A5 (de) | 2023-06-15 | 2026-04-09 | Basf Se | Weichmacher-Zusammensetzung |
| WO2025119725A1 (en) | 2023-12-07 | 2025-06-12 | Basf Se | Process for manufacturing aldehydes and alcohols from plastic waste |
| WO2025119724A1 (en) | 2023-12-07 | 2025-06-12 | Basf Se | Process for manufacturing aldehydes and alcohols from plastic waste |
| WO2026046850A1 (en) | 2024-09-02 | 2026-03-05 | Basf Se | Process for manufacturing aldehydes and alcohols from plastic waste |
| WO2026046859A1 (en) | 2024-09-02 | 2026-03-05 | Basf Se | Process for manufacturing aldehydes and alcohols from plastic waste |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3520937A (en) * | 1966-04-05 | 1970-07-21 | Basf Ag | Processing oxo reaction mixtures |
| BE787274A (fr) * | 1971-08-07 | 1973-02-07 | Basf Ag | Procede de preparation d'aldehydes a structure preponderante lineaire |
-
1974
- 1974-02-01 DE DE2404855A patent/DE2404855C3/de not_active Expired
-
1975
- 1975-01-17 BE BE152452A patent/BE824480A/xx not_active IP Right Cessation
- 1975-01-20 US US05/542,709 patent/US3932523A/en not_active Expired - Lifetime
- 1975-01-24 IT IT19586/75A patent/IT1031150B/it active
- 1975-01-27 CA CA218,728A patent/CA1056403A/en not_active Expired
- 1975-01-29 FR FR7502767A patent/FR2259805A1/fr active Pending
- 1975-01-29 SE SE7500972A patent/SE7500972L/xx unknown
- 1975-01-31 ES ES434311A patent/ES434311A1/es not_active Expired
- 1975-01-31 AT AT71475A patent/AT336559B/de not_active IP Right Cessation
- 1975-02-01 JP JP50012981A patent/JPS50106911A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50106911A (https=) | 1975-08-22 |
| AT336559B (de) | 1977-05-10 |
| DE2404855C3 (de) | 1981-01-22 |
| DE2404855B2 (de) | 1980-05-14 |
| BE824480A (fr) | 1975-07-17 |
| ATA71475A (de) | 1976-09-15 |
| US3932523A (en) | 1976-01-13 |
| FR2259805A1 (https=) | 1975-08-29 |
| IT1031150B (it) | 1979-04-30 |
| DE2404855A1 (de) | 1975-08-21 |
| SE7500972L (https=) | 1975-08-04 |
| ES434311A1 (es) | 1976-11-16 |
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