JP6657086B2 - オレフィンの高圧ヒドロホルミル化のための反応器中のコバルト付着物を除去する方法 - Google Patents
オレフィンの高圧ヒドロホルミル化のための反応器中のコバルト付着物を除去する方法 Download PDFInfo
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- JP6657086B2 JP6657086B2 JP2016532322A JP2016532322A JP6657086B2 JP 6657086 B2 JP6657086 B2 JP 6657086B2 JP 2016532322 A JP2016532322 A JP 2016532322A JP 2016532322 A JP2016532322 A JP 2016532322A JP 6657086 B2 JP6657086 B2 JP 6657086B2
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- 229910017052 cobalt Inorganic materials 0.000 title claims description 47
- 239000010941 cobalt Substances 0.000 title claims description 47
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 45
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 26
- 150000001336 alkenes Chemical class 0.000 title claims description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 113
- 229910017604 nitric acid Inorganic materials 0.000 claims description 113
- 239000000243 solution Substances 0.000 claims description 74
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 229910001429 cobalt ion Inorganic materials 0.000 claims description 22
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001868 cobalt Chemical class 0.000 claims description 9
- 229910001882 dioxygen Inorganic materials 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 7
- 229940011182 cobalt acetate Drugs 0.000 claims description 5
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 5
- -1 hydroxide ions Chemical class 0.000 claims description 4
- 238000005201 scrubbing Methods 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- VWGMCGRTCLVGQL-UHFFFAOYSA-L cobalt(2+) dihydroxide hydrate Chemical compound [OH-].O.[Co+2].[OH-] VWGMCGRTCLVGQL-UHFFFAOYSA-L 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 1
- DFVOXRAAHOJJBN-UHFFFAOYSA-N 6-methylhept-1-ene Chemical compound CC(C)CCCC=C DFVOXRAAHOJJBN-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 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
- 150000001721 carbon Chemical group 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B23/00—Obtaining nickel or cobalt
- C22B23/04—Obtaining nickel or cobalt by wet processes
- C22B23/0407—Leaching processes
- C22B23/0415—Leaching processes with acids or salt solutions except ammonium salts solutions
- C22B23/0438—Nitric acids or salts thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/002—Avoiding undesirable reactions or side-effects, e.g. avoiding explosions, or improving the yield by suppressing side-reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2455—Stationary reactors without moving elements inside provoking a loop type movement of the reactants
- B01J19/246—Stationary reactors without moving elements inside provoking a loop type movement of the reactants internally, i.e. the mixture circulating inside the vessel such that the upward stream is separated physically from the downward stream(s)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B9/00—Cleaning hollow articles by methods or apparatus specially adapted thereto
- B08B9/08—Cleaning containers, e.g. tanks
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/02—Inorganic compounds
- C11D7/04—Water-soluble compounds
- C11D7/08—Acids
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/44—Treatment or purification of solutions, e.g. obtained by leaching by chemical processes
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B7/00—Working up raw materials other than ores, e.g. scrap, to produce non-ferrous metals and compounds thereof; Methods of a general interest or applied to the winning of more than two metals
- C22B7/009—General processes for recovering metals or metallic compounds from spent catalysts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00245—Avoiding undesirable reactions or side-effects
- B01J2219/00247—Fouling of the reactor or the process equipment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00245—Avoiding undesirable reactions or side-effects
- B01J2219/00252—Formation of deposits other than coke
-
- C11D2111/20—
Description
1.5mの内径及び18mの内のり高さを有するヒドロホルミル化反応器を完全に空にし、引き続き高温水を何度か注入し、そして再び空にすることで、有機材料の残分を実質的に除去した。反応器に、コバルト64g/lを含みかつ20℃の温度を有する硝酸水溶液10m3(65gのHNO3/l)を注入した。引き続き、硝酸を反応器の底部でポンプを使って抜き出し、かつ上部で再び反応器中に加える。このようにして、約8m3/hでポンプ循環させた。
1mの内径及び18mの内のり高さを有するヒドロホルミル化反応器を完全に空にし、引き続き高温水を何度か注入し、そして再び空にすることで、有機材料の残分を実質的に除去した。反応器に、コバルト29g/lを含みかつ20℃の温度を有する硝酸水溶液20m3(161gのHNO3/l)を注入し、その際、硝酸の一部が後反応器中に溢流した。引き続き、硝酸を後反応器の底部でポンプを使って抜き出し、反応器の下部に返送した。このようにして、約8m3/hでポンプ循環させた。
1.5mの内径及び18mの内のり高さを有するヒドロホルミル化反応器を、20%の硝酸10m3を用いることによって洗浄した。洗浄が首尾よく行われていることをモニタリングするために、反応器中での内部循環時間を放射性トレーサー(radioaktive Stossmarkierung)によって測定した。指示薬として、ナトリウムの同位体24Naを使用した。
Claims (11)
- コバルト触媒を用いたオレフィンの高圧ヒドロホルミル化のための反応器中のコバルト付着物を、硝酸水溶液による処理によって除去する方法であって、ここで、前記反応器に硝酸水溶液を少なくとも部分的に入れ、前記硝酸水溶液の酸濃度及び/又はコバルトイオン濃度を処理中に測定し、前記酸濃度及び/又は前記コバルトイオン濃度の経時的な変化が所定の限界値を下回る場合に、前記硝酸水溶液の温度を高め、前記コバルト付着物の前記硝酸水溶液中への溶解に伴って発生する窒素酸化物含有オフガスを、分子状酸素を含有するガスと合一し、かつ前記オフガスを洗浄塔中で、水又はアルカリ性水溶液である水性液体に少なくとも部分的に吸収させる、前記方法。
- 前記水性液体を、洗浄塔中で前記オフガスと反対方向に導き、分子状酸素を含有するガスを、前記オフガス中に及び/又は前記洗浄塔内に導入する、請求項1に記載の方法。
- 前記硝酸水溶液を前記処理の間にわたり前記反応器中で循環させる、請求項1または2に記載の方法。
- 前記硝酸水溶液を、前記酸濃度が1l当たりHNO 3 25gを下回る及び/又は前記コバルトイオン濃度が1l当たり85gを上回るとすぐ前記反応器から排出する、請求項1から3までのいずれか1項記載の方法。
- 前記硝酸水溶液の温度を、10〜40℃の範囲の当初温度から60〜80℃の範囲の最終温度に高める、請求項1から4までのいずれか1項記載の方法。
- 前記反応器の外側で運ばれる前記硝酸水溶液の流を加熱する、請求項3から5までのいずれか1項記載の方法。
- 前記コバルト付着物の除去を完了するために、前記反応器を硝酸水溶液による前記処理後にウォータージェットで洗浄する、請求項1から6までのいずれか1項記載の方法。
- 前記反応器を、硝酸水溶液による前記処理後に水又は水蒸気でフラッシングする、請求項1から6までのいずれか1項記載の方法。
- 前記排出された硝酸水溶液からコバルトを回収する、請求項4に記載の方法。
- 前記排出された硝酸水溶液から、水酸化物イオン及び/又は酸化物イオンを含有するコバルト塩を沈殿させ、前記コバルト塩を分離し、かつ前記コバルト塩を酢酸と反応させて酢酸コバルト溶液を生ぜしめる、請求項9に記載の方法。
- 酸濃度の経時的な変化の限界値がHNO31gl−1h−1(リットル毎時)であり、及び/又はコバルトイオン濃度の経時的な変化の限界値が0.5gl−1h−1(リットル毎時)である、請求項1から10までのいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13179688.0 | 2013-08-08 | ||
EP13179688 | 2013-08-08 | ||
PCT/EP2014/066372 WO2015018710A1 (de) | 2013-08-08 | 2014-07-30 | Verfahren zum entfernen von cobaltablagerungen in einem olefin hochdruckhydroformylierung reaktor |
Publications (3)
Publication Number | Publication Date |
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JP2016529247A JP2016529247A (ja) | 2016-09-23 |
JP2016529247A5 JP2016529247A5 (ja) | 2018-10-18 |
JP6657086B2 true JP6657086B2 (ja) | 2020-03-04 |
Family
ID=49000305
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2016532322A Active JP6657086B2 (ja) | 2013-08-08 | 2014-07-30 | オレフィンの高圧ヒドロホルミル化のための反応器中のコバルト付着物を除去する方法 |
Country Status (7)
Country | Link |
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US (1) | US10385422B2 (ja) |
EP (1) | EP3030542B1 (ja) |
JP (1) | JP6657086B2 (ja) |
KR (1) | KR20160041959A (ja) |
CN (1) | CN105636927B (ja) |
MY (1) | MY183447A (ja) |
WO (1) | WO2015018710A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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TW201726242A (zh) | 2015-12-22 | 2017-08-01 | 巴斯夫歐洲公司 | 圓柱形反應器及其用於連續氫甲醯化反應的用途 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE750498C (de) | 1942-06-04 | 1953-05-11 | Ig Farbenindustrie Ag | Verfahren zur Entfernung von Eisenverbindungen aus Gemischen von Kohlenwasserstoffenund sauerstoffhaltigen Stoffen |
FR1089983A (fr) * | 1953-06-20 | 1955-03-25 | Ets Kuhlmann | Procédé de récupération du cobalt contenu dans les produits de la synthèse oxo |
FR2053177B1 (ja) | 1969-07-26 | 1973-03-16 | Basf Ag | |
JPS5031858B1 (ja) | 1970-12-25 | 1975-10-15 | ||
JPS5438297A (en) * | 1977-09-01 | 1979-03-22 | Nippon Mining Co Ltd | Production of cobalt oxide |
US4139461A (en) | 1977-12-27 | 1979-02-13 | Sterling Drug Inc. | Removal of solids from a wet oxidation reactor |
JPS5585534A (en) | 1978-12-25 | 1980-06-27 | Kuraray Co Ltd | Carbonylation of olefinic compound |
EP0024761A1 (en) | 1979-08-29 | 1981-03-11 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of alcohols or aldehydes, alcohols or aldehydes prepared by this process and stabilized compositions suitable for use in the said process |
JPS5658545A (en) | 1979-10-19 | 1981-05-21 | Mitsubishi Petrochem Co Ltd | Separating method of oxo reaction catalyst |
GB8907577D0 (en) * | 1989-04-04 | 1989-05-17 | Exxon Chemical Patents Inc | Catalyst recovery in the production of alcohols |
JP2985647B2 (ja) * | 1993-02-26 | 1999-12-06 | 住友金属鉱山株式会社 | 使用済み触媒の溶解方法 |
JP4392537B2 (ja) | 2005-01-17 | 2010-01-06 | 新第一塩ビ株式会社 | スケール付着防止剤の塗布方法 |
US7329783B2 (en) | 2005-06-30 | 2008-02-12 | Shell Oil Company | Hydroformylation process |
GB0706887D0 (en) * | 2007-04-10 | 2007-05-16 | Exxonmobil Chem Patents Inc | Cobalt recovery from cobalt catalysed hydroformylation reactions |
JP2012246519A (ja) | 2011-05-26 | 2012-12-13 | Nippon Telegr & Teleph Corp <Ntt> | 金属の浸出方法 |
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2014
- 2014-07-30 US US14/909,852 patent/US10385422B2/en active Active
- 2014-07-30 JP JP2016532322A patent/JP6657086B2/ja active Active
- 2014-07-30 CN CN201480055335.1A patent/CN105636927B/zh active Active
- 2014-07-30 MY MYPI2016000194A patent/MY183447A/en unknown
- 2014-07-30 WO PCT/EP2014/066372 patent/WO2015018710A1/de active Application Filing
- 2014-07-30 EP EP14744585.2A patent/EP3030542B1/de active Active
- 2014-07-30 KR KR1020167005724A patent/KR20160041959A/ko not_active Application Discontinuation
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US20160265084A1 (en) | 2016-09-15 |
EP3030542A1 (de) | 2016-06-15 |
EP3030542B1 (de) | 2017-06-21 |
MY183447A (en) | 2021-02-18 |
WO2015018710A1 (de) | 2015-02-12 |
KR20160041959A (ko) | 2016-04-18 |
CN105636927A (zh) | 2016-06-01 |
CN105636927B (zh) | 2018-10-09 |
US10385422B2 (en) | 2019-08-20 |
JP2016529247A (ja) | 2016-09-23 |
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