AU612528B2 - Two phase oxime synthesis - Google Patents
Two phase oxime synthesis Download PDFInfo
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- AU612528B2 AU612528B2 AU44515/89A AU4451589A AU612528B2 AU 612528 B2 AU612528 B2 AU 612528B2 AU 44515/89 A AU44515/89 A AU 44515/89A AU 4451589 A AU4451589 A AU 4451589A AU 612528 B2 AU612528 B2 AU 612528B2
- Authority
- AU
- Australia
- Prior art keywords
- oxime
- ketone
- aldehyde
- phase
- conversion
- 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
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- 150000002923 oximes Chemical class 0.000 title claims description 53
- 230000015572 biosynthetic process Effects 0.000 title description 9
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 150000002576 ketones Chemical class 0.000 claims description 31
- 239000012074 organic phase Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 150000001299 aldehydes Chemical class 0.000 claims description 18
- 239000012071 phase Substances 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 238000000638 solvent extraction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003350 kerosene Substances 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- -1 phenolic ketone Chemical class 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 description 21
- 239000007857 degradation product Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 11
- 238000011069 regeneration method Methods 0.000 description 10
- 230000008929 regeneration Effects 0.000 description 9
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229940087291 tridecyl alcohol Drugs 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000006053 organic reaction Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002443 hydroxylamines Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- IMUPGIMWAVJNES-UHFFFAOYSA-N 3-butyl-6-hydroxy-1-phenylheptan-1-one Chemical compound CCCCC(CCC(C)O)CC(=O)C1=CC=CC=C1 IMUPGIMWAVJNES-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012142 reagent concentrate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
I
17.1:-rllili e~L~ YC r -~ar;deD-L- e i
~Y
6125 2 8
AUSTRALIA
Patents Act COMPLETE SPECIFICATION
(ORIGINAL)
Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority: Related Art: Int. Class APPLICANT'S REF.: 04/TEC/AVO/MJP/BC Name(s) of Applicant(s): MEQ NICKEL PTY. LTD.
Address(es) of Applicant(s): Bentley Co., 23rd Floor, 127 Creek Street, Brisbane, Queensland 4000, Australia Actual Inventor(s): EDWARD STANLEY FERGUSSON MALCOLM JOHN PRICE JOHN GRAHAM REID Address for Service is: PHILLIPS, ORMONDE FITZPATRICK Patent and Trade Mark Attorneys 367. Collins Street Melbourne, Australia, 3000 Complete Specification for the invention entitled: TWO PHASE OXIME SYNTHESIS The following statement is a full description of this invention, including the best method of performing it known to applicant(s): P 19/11/77 vu 1%s J *r raten ana iraae MarK Attorneys 367 Collins Street Melbourne, Australia P17/2/83 2 TWO PHASE OXIME SYNTHESIS The present invention relates to an organic reagent synthesis procedure which enables organic reagent degradation products to be converted back to the parent compound. More specifically it relates to the conversion of ketones and aldehydes to oximes.
The use of organic reagents for the isolation and purification of metals in the mineral industry is widespread. Oxime type compounds in particular have been used for a number of years in the copper industry and also So in the nickel and cobalt industries.
o 0o o During the course of use of an oxime reagent in an industrial situation it may be subjected to both low and 0 0 high pH solutions. These extremes of pH may be encountered a o 0 during the extraction and stripping cycles of a continuously o.o operating solvent extraction plant. Continued exposure to either high or low pH solutions, particularly at higher than ambient temperatures, will result in degradation or hydrolysis of the oxime resulting in the formation of a 00oooo °oo° ketone or aldehyde product. These ketone and aldehyde o°o°o degradation products accumulate in the organic phase and do not take part in the recovery of metals since they have no o.o0- metal complexing ability.
0The various oxime type reagents used in solvent extraction systems are relatively expensive. Consequently, any procedure to convert the degradation product back to the parent oxime should result in reduced operating costs in the solvent extraction circuit.
The continued accumulation of the organic reagent degradation products in the solvent phase may impair the 1 physical properties of the reagent mixture. As the degradation products cannot extract metals, new oxime reagent has to be added to the organic phase to maintain the design metal loading power of the organic reagent mixture,, This continued addition of reagent concentrate will result in viscosity and density changes which may have a significant deleterious effect on metal transfer kinetics
AP
I
Melbourne, Australia 3 and phase separation.
Commercial solvent extraction plants are designed using both metal transfer kinetic data and phase separation rate information. It is important that the properties of the organic phase are maintained as similar as possible to those of the mixture used for design purposes. Clearly, if metal transfer kinetics are slowed due to the development of a more viscous organic phase because of the accumulation of unwanted degradation products then the throughput for a given design will decrease. The same. end result will occur if the phase separation rate decreases.
oo The present invention enables both physical and chemical properties of the organic reaction mixture to be S controlled and maintained in a condition similar to that used for design purposes, It will be recognised by those skilled in the art of 4 solvent extraction that the above physical problems, associated with the accumulation of degradation products, would be corrected if the specific degradation product could be isolated and removed from the mixture. However, there is S no simple economically feasible procedure for the isolation of closely related organic compounds.
Accordingly, the present invention provides a method 4 fol the conversion of ketones and aldehydes to corresponding oximes wherein a ketone or aldehyde is dissolved in a substantially water immiscible organic solvent and reacted with a hydroxylamine acid addition salt and aqueous ammonia to form the corresponding oxime from the ketone or aldehyde, water, and the ammonium salt of the acid.
The method of the invention is thus an organic reaction procedure that enables "in situ" conversion of the ketone or aldehyde degradation product back to its parent oxime. The reaction may be carried out on batches of organic phase material removed from the main metal extraction system or on a proportion of the organic phase continuously removed from and returned to the main system.
The reaction used in the present invention is specific to the reactants concerned. The only products of the reaction
AP
apart from the desired oxime are ammonium salts and water which contribute to the aqueous phase, not the organic phase.
Oxime regeneration in accordance with the present invention is achieved by reacting a ketone or aldehyde with hydroxylamine in the presence of aqueous ammonia. In the two phase liquid system where the invention is particularly useful, a water-soluble hydroxylamine salt is used to form corresponding ammonium salts which are taken up by solution in the aqueous phase. The oxime product dissolves in the organic phase for re-use in the metal extraction system.
The reaction as applied to commercially available o materials encountered in metal extraction systems is illustrated by the following equation: 0 0 o oo 0 0 Q 00) 0
Y
0000 X C=0 oo c=o .oo0 NH2 OH.HC1 NH OH 0 00 o a -CN
OH
oo000 o0 0 0 0 4 f orooo o+
NH
4 C1 2 ooooo OH 0 C t where X CH 3
(CH
2 7
CH
2
CH
3
(CH
2 1 0
CH
2 or branched isomers Y H, CH 3 The above equation shows phenolic materials because the phenolic hydrogen is the leaving group in the metal chelation reaction. However, the presence of the phenolic hydroxyl group is not essential to the present invention.
~I I;ii_ /_iiij __II_~LIY~_I 5 Similarly, the X groups illustrated are present in the commercially used materials to confer appropriate solvent solubility on the oxime molecule. A hydrophobic side chain will decrease the aqueous phase solubility of the molecule which is desirable to prevent loss of the oxime into the aqueous phase. However, inappropriate side chains, such as longer or more complex alkyl groups, could undesirably affect the viscosity of the organic phase. The nature of the X group, or indeed the presence or absence of this group, is not a critical feature of this invention.
SAgain, the Y groups illustrated are used and chosen o commercially because of their effect on metal extraction o strength and surface properties. In relation to the present 0 a 0 0 invention, the nature of the Y group will affect the oxime O0 O 0o0 O regeneration rate. Thus, for example, ketones in which Y is o phenyl have a slower regeneration rate to the corresponding S oxime than ketones in which Y is methyl. Alkyl groups other than methyl or substituted phenyl groups could be used but with probable slowing of the regeneration rate.
The ketone or aldehyde is dissolved in a substantially ooo 0 0 water immiscible organic solvent before the reaction is o0 0 0 carried out. The solvent used may be mainly aliphatic or 0 0), aromatic hydrocarbon. Kerosene is a preferred solvent.
o,00 Where a particular water immiscible organic solvent is used 000 in a metal extraction process, the same solvent forms the o 0 organic phase in the reaction of the present invention.
0000 S0 The temperature at which the regeneration reaction will be conducted will depend both cn the reagents and their concentration as well as on the choice of batch or continuous reaction. Other factors such as the desired rate of reaction and the extent to which the reaction is to be completed will also influence the choice of reaction temperature.
The use of temperatures over 60 0 C greatly increases the reaction rate and therefore decreases the size of the vessel required to process the reagent to be regenerated.
However, higher temperatures such as 70°C enhance corrosion and allow loss of the ammonia compound of the i. 6 reaction mixture.
If batch regeneration is to be used with a continuous extraction process, the quantity of reagent to be regenerated and the time taken to proceed to the desired level of regeneration will determine the size of the reaction vessel. On the other hand, the regeneration procedure of the invention may be used to treat stored batches of degraded reagent where prompt return to the extraction process is not critical. In this case, vessel size is not as important.
The invention is illustrated by the following ii.n-limiting examples of oxime regeneration.
EXAMPLE 1 o 0 0 0 0 0 00 0 0 0 1 0 *0 0 0 0 0 1 A sample of a commercially available oxime was mixed 0ooo with kerosene and was used continuously in a solvent extraction plant for a period of 5 months. The organic phase containing the oxime when analysed was found to contain 2.8% w/w of a ketone resulting from oxime 000oooo 00 0 degradation.
o°o One hundred ml of the organic phase was contacted with an equal volume of aqueous phase containing 8 g NH 3 and 2.0 g hydroxylamine hydrochloride dissolved therein.
o0-o ooS After stirring the mixture for approximately 20 hours 0 0 at higher than ambient temperature the phases were allowed 00O o0° 0 to separate and on analysis greater than 80 percent of the initial degradation product was found to have been converted to the parent oxime.
In addition when the organic phase recovered from the above "in situ" two phase oxime regeneration was contacted with a suitable solution containing nickel it was found that the increased nickel loading ability of the organic phase was exactly proportional to the percentage of ketone (the degradation product) converted to oxime.
Modifiers are frequently incorporated into the organic phase and these reagents, of which tridecylalcohol is an example, have been shown to have no effect on the above 7 reaction. An "in situ" two phase oxime synthesis in the presence of tridecylalcohol is given in Example No. 2.
EXAMPLE 2 One hundred ml of the organic phase consisting of 2.8% w/w ketone (the degradation product) and 17% w/w tridecylalcohol together with undegraded oxime and kerosene was contacted with an equal volume of aqueous phase containing 8 g of NH 3 and 2 g of hydroxylamine hydrochloride dissolved therein. After stirring the mixture o O 0O o o for approximately 20 hours at 60 C the phases were allowed oocoo to separate. The organic phase was recovered and analysed 0 0 o o wherein it was found that in excess of 80% of the o000 degradation product, 2-hydroxy-5-nonylacetophenone, had been 0000 0 00oo converted to the oxime, 0000 ooo It will be recognised by those familiar with organic reactions that both the quantities of hydroxylamine hydrochloride and ammonia used in examples 1 and 2 above are in excess of that stoichiometrically required to achieve 0000 oo0 0 complete conversion of ketone to oxime. Losser quantities of hydroxylamine reagent reduce the reaction rate and make the reaction less economically attractive.
0 oo0oo In the above described two phase reaction system the ooooon unreacted reagents hydroxylamine hydrochloride and ammonia S 0 0 are not lost as they remain in the aqueous phase. In 0000oooo I 00o o addition any ketone or aldehyde degradation product that is not converted to oxime is also not lost as it remains in the organic phase.
The same aqueous phase with additions of ammonia and hydroxylamine salt as required may be used repeatedly to contact different batches of organic reagent containing degradation product.
Results from this multiple contact system are presented in Example No. 3.
AP
.i 8 EXAMPLE 3 One hundred and fifty ml of the organic phase consisting of 2,8% w/w ketone (the degradation product) and 17% w/w tridecylalcohol together with undegraded oxime and kerosene was contacted with an equal volume of aqueous phase containing 12 g of NH 3 and 20 g of hydroxylamine hydrochloride dissolved therein. After stirring the mixture for approximately 24 hours at 25 C the phases were allowed to separate.
It was found that the ketone concentration in the 0oo 00 organic phase had been reduced to 1% w/w.
oooooo Without changing the composition of the aqueous phase, o o o co a second sample of 150 ml of organic mixture of identical 0000 composition to that described above was added and agitation o00o at 38 C was carried out for 24 hours. Analyses of the 000o ooo organic phase showed that the ketone concentration had been reduced to 0.5% w/w.
The above procedure was repeated (24 hours at 38 C) with a third 150 ml increment of organic reagent mixture and 0000 o00 o again the analysis of the organic phase showed that the 0 00 o0 oo ketone concentration had been reduced to 0.5 w/w.
In addition to the reduction of ketone concentration 0 0oo0oo by conversion to the oxime, it was also found that the ooooo nickel loading capacity of the organic mixture increased.
If either a batch system or a continuous system of "in 0000 0oo 0 situ" two phase oxime synthesis is incorporated into a plant it is necessary to carry out the reaction in as short a time as possible. This will have an important economic bearing on the size of the tankage required.
Experiments were carried out at different temperatures to determine the optimum conditions for the reaction. The results are given in Example 4.
EXAMPLE 4 One hundred and fifty ml of the organic phase consisting of 2.8% w/w ketone (the degradation product) and 17% w/w tridecylalcohol together with undegraded oxime and kerosene was contacted with an equal volume of aqueous phase
AP
i j3 :!i ii 9 containing 12 g of NH 3 and 2 g of hydroxylamine sulphate.
The above phases were agitated for 12 hours at and the experiment was repeated with new phases at 70 0
C.
Analysis of the organic phases from each experiment at 6 and 12 hour intervals gave the following results:- At 70 C, 80% of the ketone had been converted to oxime within 6 hours.
At 60 C, 80% of the ketone had been converted to oxime within 12 hours.
Thus the reaction should proceed at 60-70 C for 6-12 hours to enable acceptable conversion of the degradation product to oxime.
sooeo As the above example illustrates the reaction system o oo will proceed equally well if hydroxylamine sulphate is used 0o 0 instead of hydroxylamine chloride. Where the corrosive 00 ,o nature of the chloride ion may present a problem, it would 0000 000o be preferable to use hydroxylamine sulphate.
The invention as described above can be readily incorporated into the flow streams of operating solvent extraction plants using oxime type metal extracting 0000 oo0 I reagents. The choice of either a continuous or a batch 0 00 o'o 0 o system of "in situ" two phase oxime synthesis will depend primarily on the rate of degradation of the oxime to the 0 o0 oo ketone or aldehyde. The rate of carbonyl conversion back to Coog oxime for a particular reaction system will also be a factor in this choice.
0000 0oo° It will be obvious to those experienced in the commercial utilisation of solvent extraction that a percentage of the oxime reagent always remains complexed with the metal species being extracted. The stripping systems used do not completely remove all of the metal from the organic reagent. The presence of a metal organic complex has no effect on the efficiency of the "in situ" two phase oxime synthesis.
Claims (9)
1. A method for the conversion of ketones and aldehydes to corresponding oximes wherein a ketone or aldehyde is dissolved in a substantially water immiscible organic solvent and reacted with a hydroxylamine acid addition salt and aqueous ammonia to form the corresponding oxime from the ketone or aldehyde, water, and the ammonium salt of the acid.
2. A method as claimed in claim 1 wherein the reaction occurs in a two-phase system, the ammonium salt being held substantially by an aqueous phase and the oxime being held Sa by an organic phase.
3. A method as claimed in claim 1 or claim 2 wherein the I; c ketone or aldehyde is a phenolic ketone or aldehyde. 0
4. A method as claimed in claim 3 wherein the phenol ring has a hydrophobic side chain. °o
5. A method as claimed in claim 4 wherein the hydrophobic o o, side chain is a straight or branched chain alkyl group having from 9 to 12 carbon atoms. S
6. A method as claimed in claim 3 wherein a phenolic alkyl ketone is converted to the corresponding oxime. i 00 0
7. A method as claimed in any one of claims 3 to wherein a phenolic optionally substituted aryl ketone is converted to the corresponding oxime.
8. A method as claimed in any preceding claim wherein the substantially water immiscible organic solvent is kerosene.
9. A method for the solvent extraction of metal values using an oxime extraction agent and wherein the oxime is degraded in use by partial conversion to its corresponding ketone or aldehyde, said method including the conversion of XW~ i- i i- i- i 11 said ketone or aldehyde to its corresponding oxime by a method as claimed in any preceding claim. A method as claimed in claim 9 wherein the conversion reaction is carried out on the extraction agent as removed from the metal extraction procedure. DATED: 8 November, 1989 Coi e a 00P PHILLIPS ORMONDE FITZPATRICK Attorneys for: MEQ NICKEL PTY. LTD. t y 00 CC) C) 0 0' u 0 C O 0 e C)' 0 4 4444 O 04P 04i 4
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU44515/89A AU612528B2 (en) | 1988-11-21 | 1989-11-09 | Two phase oxime synthesis |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPJ1581 | 1988-11-21 | ||
| AUPJ158188 | 1988-11-21 | ||
| AU44515/89A AU612528B2 (en) | 1988-11-21 | 1989-11-09 | Two phase oxime synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4451589A AU4451589A (en) | 1990-05-24 |
| AU612528B2 true AU612528B2 (en) | 1991-07-11 |
Family
ID=25626784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU44515/89A Expired AU612528B2 (en) | 1988-11-21 | 1989-11-09 | Two phase oxime synthesis |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU612528B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI20155195A7 (en) | 2015-03-20 | 2016-09-21 | Outotec Finland Oy | Treatment of degraded oxime metal extractants in process organic solutions |
-
1989
- 1989-11-09 AU AU44515/89A patent/AU612528B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4451589A (en) | 1990-05-24 |
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