WO2012148415A1 - Procédé de récupération de métal précieux et élimination de couleur dans milieu de réaction liquide contenant un produit organosilicium - Google Patents
Procédé de récupération de métal précieux et élimination de couleur dans milieu de réaction liquide contenant un produit organosilicium Download PDFInfo
- Publication number
- WO2012148415A1 WO2012148415A1 PCT/US2011/034499 US2011034499W WO2012148415A1 WO 2012148415 A1 WO2012148415 A1 WO 2012148415A1 US 2011034499 W US2011034499 W US 2011034499W WO 2012148415 A1 WO2012148415 A1 WO 2012148415A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- precious metal
- liquid reaction
- reaction medium
- platinum
- recovery
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/32—Post-polymerisation treatment
- C08G77/34—Purification
Definitions
- the present invention relates to a process of precious metal catalyst recovery from an organosilicon product-containing liquid reaction medium containing precious metal catalyst.
- the present invention relates to a process of precious metal catalyst recovery from an organosilicon product-containing liquid reaction medium containing precious metal catalyst wherein the liquid reaction medium is produced by precious metal-catalyzed hydrosilation processes.
- organosilicon product-containing reaction media e.g., siloxane or silane streams
- organosilicon product-containing reaction media e.g., siloxane or silane streams
- a hydrosilylation product of triethoxysilane with 1-octene can have a color of less than 30 pt-co.
- precious metal catalysts such as platinum in the product causes product color, i.e., having a color of about 30-60 pt-co.
- heavy distillation is needed to remove precious metals and to reduce product color. This additional heavy distillation step not only reduces product yield but also significantly increases final product cost.
- the present invention is process for recovery of a precious metal catalyst from an organosilicon product-containing liquid reaction medium containing precious metal catalyst which has the steps of:
- FIG. 1 schematically illustrates a flow sheet of a precious metal recovery process from a siloxane copolymer unit or a silane hydrosilylation unit.
- FIG. 2 schematically illustrates a flow sheet of a precious metal recovery process from a silane distillation unit.
- FIG. 3 shows long-term fixed-bed platinum recovery results from Siloxane-A at
- FIG. 4 shows platinum loading distribution on silica gels after a long-term fixed- bed treatment of Siloxane-A.
- FIG. 5 shows long-term fixed-bed platinum recovery results from Heavy-A waste at the temperature of 75°C and the residence time of 203-464 minutes.
- FIG. 6 shows platinum loading distribution on silica gels after a long-term fixed- bed treatment of Heavy-A waste.
- FIG. 7 shows Silane-A product appearance without fixed-bed treatment (left container) and with a fixed-bed treatment (right container) as discussed in Example 6.
- the present invention provides a process for significant precious metal recovery from an organosilicon product-containing liquid reaction medium produced from hydrosilation reaction or from silane heavy wastes after silane distillation containing precious metal catalyst. Further, the present invention provides for recovery from an organosilicon product-containing liquid reaction medium to significantly reduce the product color and precious metal precipitation of organosilicon products. Further, for certain organosilicon products where distillation is required only for removing precious metal and reducing product color, the present invention provides a process of precious metal recovery and product color removal and thus eliminates the costly distillation step, thus increasing product yield and significantly reducing final product cost. Further, the present invention provides a commercially feasible and economical process for accomplishing the above objectives. Still further, the present invention provides for recovery of precious metal catalyst in a high yield suitable for reuse in catalytic or other reactions.
- the present invention provides a process for precious metal catalyst recovery from an organosilicon product-containing liquid reaction medium containing precious metal catalyst by adsorbing the precious metal via a fixed-bed precious metal adsorption unit which is placed in-between a source of organosilicon product-containing liquid reaction medium containing the precious metal catalyst, e.g., a continuous siloxane copolymer unit or a continuous silane hydrosilation unit, and a product storage container.
- a source of organosilicon product-containing liquid reaction medium containing the precious metal catalyst e.g., a continuous siloxane copolymer unit or a continuous silane hydrosilation unit
- the present invention provides for advantageous precious metal catalyst recovery from an organosilicon product- containing liquid reaction medium containing precious metal catalyst via a fixed-bed precious metal adsorption unit placed in-between a source of organosilicon product-containing liquid reaction medium containing the precious metal catalyst, e.g., a silane distillation unit, and a silane heavy waste storage container.
- a source of organosilicon product-containing liquid reaction medium containing the precious metal catalyst e.g., a silane distillation unit, and a silane heavy waste storage container.
- organosilicon product-containing liquid reaction medium containing a precious metal catalyst, e.g., a continuous siloxane copolymer unit, a continuous silane hydrosilation unit or a continuous silane distillation unit, and a product or waste storage container
- organosilicon product-containing liquid reaction medium is passed from the source of organosilicon product-containing liquid reaction medium and is directly fed into a fixed-bed precious metal adsorption unit.
- the fixed-bed precious metal adsorption unit and pipes between the source of the organosilicon product-containing liquid reaction medium and fixed-bed precious metal adsorption unit are insulated to maintain the high temperature of the liquid reaction medium in order to adsorb precious metal onto the adsorbent.
- One example material that can be used for insulation is calcium silicate.
- a fixed-bed adsorption operation is an operation in which additive material (e.g., precious metal adsorbent) is placed in and remains stationary in an adsorption unit (e.g., a cylindrical adsorption column) to adsorb precious metals.
- additive material e.g., precious metal adsorbent
- an adsorption unit e.g., a cylindrical adsorption column
- the liquid reaction medium resulting from a pass through of a precious metal adsorption bed is re-contacted at least once with precious metal adsorbent at precious metal adsorption conditions to adsorb precious metal thereon; separating precious metal adsorbent from the liquid reaction medium; and, recovering adsorbed precious metal from said precious metal adsorbent.
- the contacting and re-contacting steps can be carried out in a continuous manner by passing the liquid reaction medium through one or more fixed precious metal recovery adsorbent beds which include at least one precious metal adsorbent until the desired clarification and decolorization is completed.
- Such a continuous operation may use more than one precious metal adsorption units, e.g., a lead bed and lag beds, to adsorb the precious metal to achieve the desired color and amount of platinum recovery resulting in a treated liquid reaction medium having a low precious metal content, low color and/or low precious metal precipitation of the precious metal, i.e., less black particles therein.
- the treated liquid reaction medium is then placed into storage containers.
- the precious metal adsorbent is an adsorbent with a polymer backbone matrix, an inorganic backbone matrix or a mixture thereof.
- Adsorbents with a polymer backbone matrix selected to adsorb the desired precious metal from the liquid reaction medium include ion-exchange resins or chelating resins.
- Adsorbents with an inorganic backbone matrix include silica gel, functionalized silica gel such as PHOSPHONICS, activated carbon and inorganic nanoparticles (e.g., Fe 3 0 4 ).
- PHOSPHONICS silica gel is described in U.S. Publication No. 2009/0098082, EP Patent No. EP 1,786,850 and International Publication No.
- Adsorbents with inorganic backbone matrices are preferable for excellent thermal and long-term stability in the adsorbent beds.
- Adsorbents can have specific functional groups which are selected based on the desirable affinity with precious metals. Examples of specific functional groups include mercapto (-SH), sulfide (-S-), amino (including primary, secondary, or tertiary amine), or a mixture thereof.
- specific functional groups include mercapto (-SH), sulfide (-S-), amino (including primary, secondary, or tertiary amine), or a mixture thereof.
- the adsorbents can be efficient for recovery of precious metals in various forms such as ionic forms or elements, solution or colloidal.
- the liquid reaction medium containing precious metal to be treated can be a product of a reaction such as hydrosilation and hydroformylation, which is catalyzed by a precious metal catalyst.
- Hydrosilation reactions for syntheses of organosilicon i.e.,
- organosiloxane or organosilane products are well known and generally involve catalyzed hydrosilation of an aliphatically unsaturated compound with a silane or a silicon polymer containing reactive silanic-hydrogen and/or hydrogen-siloxy units in the presence of a precious metal catalyst, e.g., platinum, rhodium and palladium.
- a precious metal catalyst e.g. platinum, rhodium and palladium.
- the organosilicon product-containing liquid reaction medium containing precious metal can be provided from a continuous siloxane copolymer unit, a continuous silane distillation unit or a continuous silane hydrosilation unit.
- Hydroformylation reactions for synthesis of aldehydes are also well known and generally involve treatment of alkenes using a precious metal catalyst.
- the present process can also be applied to a commercially available organosilicon product which has undesirable color or amounts of precious metal catalyst which can be recovered due to entrainment thereof.
- the liquid reaction medium can be the crude liquid product of a reaction effected in the presence of one or more of the catalysts, such as the crude product mixture obtained from platforming reactions, the hydrogenation of fats and oils, hydrogenation reactions, oxidation of higher alcohols, ring opening polymerization reactions, and others which contain up to 5,000 ppm of one or more of a precious metal catalyst.
- Hydrosilation reactions can generally be carried out at a temperature between about 25°C and about 200°C, preferably between about 50°C and about 120°C under a pressure of from about 0 psig to about 500 psig for a period of from about 5 minutes to several days, in the presence of a small amount of precious metal catalyst, e.g. between about 1 ppm and about 5,000 ppm, which is entrained in the resulting organosilicon product-containing liquid reaction medium.
- a small amount of precious metal catalyst e.g. between about 1 ppm and about 5,000 ppm
- the resulting liquid reaction medium from the reactions described above or waste streams after heavy silane distillation are contacted with a precious metal adsorbent under precious metal adsorption conditions to adsorb precious metal thereon.
- the adsorbent can be placed in one or more fixed-bed precious metal adsorption units, e.g., one or more columns containing functionalized silica gel for precious metal adsorption, for the liquid reaction medium to pass through at a desired rate and/or with a desired residence time of the liquid reaction medium in the adsorption bed(s) for optimal precious metal adsorption.
- a fixed-bed adsorbent unit is connected to and placed directly after the source of the liquid reaction medium, e.g., a continuous high vacuum silane distillation unit, continuous siloxane copolymer unit or continuous silane hydrosilation unit, such that the liquid reaction medium passes directly to the fixed absorption bed and precious metal is obtained on the adsorbent without costly heating needed.
- Precious metal adsorption conditions can include a temperature of the liquid reaction medium within the precious metal adsorption unit of between about ambient and about 200°C, about 25°C and about 200°C, most preferably between about 40°C and about 120°C.
- Precious metal adsorption conditions can include a pressure range of from about atmospheric to about 100 atmospheres.
- precious metal adsorption conditions include a residence time of the liquid reaction medium to be contacted with said precious metal adsorbent sufficient to achieve a satisfactory amount of adsorption of precious metal onto the precious metal adsorbent, e.g., about 1 minute to about 24 hours.
- the viscosity of the organosilicon product-containing liquid reaction medium containing precious metal catalyst to be treated is in a range of about OcSt to about lOOOcSt at 25°C, preferably about OcSt to about 500cSt at 25°C, and most preferably about OcSt to about 200cSt at 25°C.
- Treatment of low viscosity liquid reaction media is more effective for precious metal recovery than treatment of high viscosity liquid reaction media since those liquid reaction media with low viscosities diffuse into the pores of adsorbent material, e.g.,
- a liquid reaction medium having low viscosity is defined as a medium having a visocity with a range of about OcSt to about 200cSt at 25°C.
- a liquid reaction medium with high viscosity is defined as a medium having a viscosity above 1000 cSt at 25°C.
- the organosilicon product-containing liquid reaction medium containing precious metal catalyst is flowed directly from continuous siloxane copolymer unit, continuous silane hydrosilylation or continuous silane distillation units to one or more fixed adsorption beds containing precious metal adsorbent for in-situ precious metal recovery by contacting the liquid reaction medium to the precious metal adsorbent.
- the one or more fixed adsorption beds is connected directly to the continuous siloxane copolymer unit, continuous silane hydrosilylation or continuous silane distillation units for precious metal recovery from organosilicon product-containing liquid reaction media (e.g., siloxane or silane products or silane heavy wastes).
- the process of the present invention is much more advantageous compared to batch-wise recovery processes since there are high manufacturing-related recovery costs associated with the costly and time-consuming batch-wise recovery process (e.g., additional batch kettle cycle time), which will diminish the benefit of precious metal cost savings.
- the process of the present invention where no dilution solvent is needed is much more advantageous compared to processes where dilution solvent will be needed since the high recovery costs associated with solvent consumption and final product regeneration will diminish the benefit of precious metal cost savings.
- the organosilicon product-containing liquid reaction medium e.g.
- silicone products or silane heavy wastes flowing out of continuous hydrosilylation units or continuous distillation units are directly passed through the at least one fixed-bed adsorption units for precious metal recovery, without change of existing continuous hydrosilylation and continuous distillation equipments.
- the recovery process is continuous. Thus, there are almost no manufacturing-related recovery costs in addition to the adsorbent material costs associated with the process of the present invention, after the initial installation and investment of the precious metal adsorption unit.
- Advantages of the process of the present invention include: (1) recovery with very low manufacturing-related recovery costs, (2) no costly heating needed for adsorbent bed recovery columns since the organosilicon product-containing liquid reaction media produced out of continuous hydrosilylation and continuous distillation units already have high temperatures suitable for recovery of precious metal, (3) the process of the present invention does not change the existing continuous hydrosilylation and continuous distillation processes and thus, the investments (e.g. fixed-bed installation) for modification of the existing processes can be minimized, and (4) high precious metal recovery and high precious metal loading on adsorbents can be obtained. As a result, the value of the recovered precious metal can be significantly higher than the cost of the adsorbents.
- precious metal recovery therefrom can be completed using well known methods such as leaching the adsorbent with an inorganic hydroxide solution, converting the precious metal group anions to a soluble salt and regenerating the catalyst by contacting the salt solution with a cationic exchange resin.
- the precious metal-loaded adsorbent can be incinerated such that the precious metal is recovered as elemental metal.
- Precious metal catalysts that can be used and recovered by the process of this invention include palladium, rhodium, ruthenium, rhenium, and platinum, e.g.,
- organosilicon product- containing liquid reaction medium produced from sources of the media, e.g., continuous siloxane copolymer units, continuous silane distillation units or continuous silane hydrosilation units, would already have high temperatures suitable for adsorbing precious metal onto the adsorbent when passed through the fixed-bed precious metal adsorption unit for recovery of the precious metal.
- sources of the media e.g., continuous siloxane copolymer units, continuous silane distillation units or continuous silane hydrosilation units
- the fixed-bed precious metal adsorption unit used a cylindrical column packed with PhosphonicSTM functionalized silica gels as adsorbent for fixed-bed platinum recovery.
- One adsorption unit was used with a single pass of the liquid reaction medium through the adsorption unit.
- the column had a heating cooling jacket to control the column temperature for precious metal recovery.
- Test 1 - Siloxane product treated Siloxane-A (viscosity of about 19 cSt at 25°C).
- Siloxane-A is a hydrosilylation product of silanic fluid MD'M with excess of polyether APEG- 350-OMe, and was made in a continuous siloxane copolymer unit.
- MD'M The structure of APEG-350-OMe:
- Example 1 A- I D the fixed-bed adsorption unit with the above-discussed specifications was used to treat Siloxane-A at a specific temperature and residence time.
- a fixed bed adsorption unit with the above-discussed specifications was placed directly between a Siloxane-A feeding reservoir (i.e., the continuous siloxane manufacturing unit in a large-scale commercial production) and a product storage container for the siloxane liquid reaction medium to continuously pass through the fixed bed adsorption unit for precious metal recovery.
- Example 1 A used a relatively high temperature and relatively long residence time for recovery study.
- Example IB used a shorter residence time compared to Example 1 A to study the residence time effect.
- Example 1C used a lower temperature compared to Example I B to study the temperature effect.
- Example ID used the same conditions as Example IB, but the experiments were carried out with an extensive period of time to study the durability of the adsorbent and evaluate the platinum loading achievable on the adsorbent.
- FIG. 3 shows the long-term fixed-bed volume testing data of Siloxane-A (completed at 75°C with a short residence time of 16 minutes in an adsorption unit with the specification as discussed above).
- the final loaded platinum value on adsorbents must be higher compared to the cost of adsorbents before the platinum- saturated adsorbents in the fixed-bed adsorption unit are removed and the unit is repacked with fresh adsorbents to make the process beneficial and economical.
- concentration of the solubilized platinum in the product was analyzed using Inductively Coupled Plasma Mass Spectroscopy, and the platinum recovery and color results were real-time data, i.e., at a specific BV, not the average of the entire period, as shown in FIG. 3.
- Test 2 - Siloxane product treated Siloxane-B (viscosity of about 260 cSt at 25°C).
- Siloxane-B is a hydrosilylation product of silanic fluid MDi5.3D'5. 7 M with excess of polyether APEG-350-OH, made in continuous siloxane copolymer unit.
- the structure of MDISJD'SJM The structure of APEG-350-OH: The concentration of the S olu >ilized platinum in the product was analyzed using Inductively Coupled Plasma Mass Spectroscopy.
- Example 2A the fixed-bed adsorption unit with the above-discussed specifications was used to treat Siloxane-B at a specific temperature and residence time.
- a fixed bed adsorption unit with the above-discussed specifications was placed directly between a Silxoane-B feeding reservoir (i.e., the continuous siloxane manufacturing unit in a large-scale commercial production) and a product storage container for the siloxane liquid reaction medium to continuously pass through the fixed bed adsorption unit for precious metal recovery.
- Example 2A used a relatively short residence time for recovery study.
- Example 2B used a longer residence time compared to Example 2A to study the residence time effect.
- Example 2B platinum level: 3.94ppm, recovery: 35.3% and product color 130pt-co
- Example 1 A platinum level: 0.37ppm, recovery: 93.0% and product color 40pt-co
- Example 2B had a higher viscosity (260 cSt at 25°C) compared to the siloxane fluid used in Example 1 A (19 cSt at 25°C).
- This suggested that the process of the present invention is more desirable for precious metal recovery from organosilicon product-containing liquid reaction medium containing precious metal catalyst having a relatively low viscosity (e.g., Examples in Test 1) compared to media having a relatively high viscosity (e.g., Examples in Test 2).
- Test 3 - Siloxane product treated Siloxane-C (viscosity of about 2.88 cSt at
- Siloxane-C is a hydrosilylation product of silanic fluid MD'M (defined above) with 1- octene. The concentration of the solubilized platinum in the product was analyzed using
- Example 3 the fixed-bed adsorption unit with the above-discussed specifications was used to treat the Siloxane-C at a specific temperature and residence time.
- a fixed bed adsorption unit with the above-discussed specifications was placed directly between a Siloxane-C feeding reservoir (i.e., the siloxane manufacturing unit in a large-scale commercial production) and a product storage container for the siloxane liquid reaction medium to pass through the fixed bed adsorption unit for precious metal recovery.
- Example 3 As evident from the data above, excellent platinum recovery and product color removal were achieved for low viscosity liquid reaction media.
- the results in Example 3 were more desirable compared to Example 2B even though similar temperature and residence times were used in both examples due to the lower viscosity of the liquid reaction medium in Example 3 (i.e., 2.88cSt at 25°C) compared to the liquid reaction medium of Example 2B (i.e., 260 cSt at 25°C).
- the platinum recovery and product color removal results in Example 3 were more desirable compared to those of Example 1 A even though similar temperature and residence times were used in both examples. Again, due to the lower viscosity of the liquid reaction medium used in Example 3 (i.e., 2.88cSt at 25°C) compared to the liquid reaction medium of Example 1 A (i.e., 19cSt at 25°C).
- Test 4 Silane heavy waste treated: Heavy-A
- Heavy-A waste is heavy waste generated by hydrosilylation of trimethoxysilane with allyl methacrylate and followed by distillation. UCON lubricant was used during distillation and remained in the heavy waste stream. Heavy-A waste had a viscosity of less than 80cSt at 25°C. The concentration of the solubilized platinum in Heavy-A waste was analyzed using Inductively Coupled Plasma Mass Spectroscopy. The platinum level of Heavy-A waste which was obtained directly from a commercial continuous silane distillation unit was measured without fixed-bed adsorption treatment:
- Example 4A and 4B the fixed-bed adsorption unit with the above-discussed specifications was used to treat the Heavy-A waste at a specific temperature and residence time.
- a fixed bed adsorption unit with the above-discussed specifications was placed directly between a silane heavy waste reservoir (i.e., the continuous silane distillation unit in a large-scale production) and a heavy waste storage container for the waste to continuously pass through the fixed bed adsorption unit for precious metal recovery.
- Example 4A shows the data of recovery results at a specific temperature and residence time.
- Example 4B the experiments were carried out with an extensive period of time to study the durability of the adsorbent and evaluate the platinum loading achievable on the adsorbent.
- FIG. 5 shows data from long-term fixed-bed volume testing of Heavy-A waste completed at 75°C with a residence time of 203-464 minutes in an adsorption unit with the specifications discussed above.
- the final loaded platinum value on adsorbents must be higher compared to the cost of adsorbents before the platinum-saturated adsorbents in the fixed-bed adsorption unit are removed and the unit is repacked with fresh adsorbents to make the process beneficial and economical.
- concentration of the solubilized platinum in the waste stream was analyzed using Inductively Coupled Plasma Mass
- FIG. 5 shows the platinum recovery results in real-time data, i.e., at a specific BV, not the average of the entire period.
- the silica gels showed over 98% platinum removal from Heavy-A waste with a residence time of 203 minutes.
- the platinum level after treatment was ⁇ 1 ppm at this earlier stage having BV ⁇ 12.
- Heavy-B waste is heavy waste generated by hydrosilylation of triethoxysilane with 1- octene and followed by distillation in a continuous silane distillation unit. UCON lubricant was used during distillation and stayed in heavy waste stream. Heavy-B waste had a viscosity of less than lOOcSt at 25°C. The concentration of the solubilized platinum in the waste stream was analyzed using Inductively Coupled Plasma Mass Spectroscopy.
- Example 5A and 5B the fixed-bed adsorption unit with the above-discussed specifications was used to treat Heavy-B waste at a specific temperature and residence time.
- a fixed bed adsorption unit with the above-discussed specifications was placed directly between a silane heavy waste reservoir (i.e., a continuous silane distillation unit in a large scale commercial production) and a heavy waste storage container for the waste liquid reaction medium to continuously pass through the fixed bed adsorption unit for previous metal recovery.
- the process in Example 5B used a lower temperature compared to Example 5A to compare the effect of different temperatures.
- Example 5A a higher fixed-bed temperature, such as 90°C as in Example 5A resulted in 91.8% recovery, compared to 70.4% recovery in Example 5B which utilized a lower fixed-bed temperature of 40°C.
- a high fixed-bed temperature had a desirable effect on platinum recovery from silane heavy wastes. Further, with longer residence time and multi-beds usage as in commercial productions, additional platinum recovery would be expected.
- Silane-A produced from a silane manufacturing unit.
- Silane-A is a silane product produced by hydrosilylation of triethoxysilane with 1-octene.
- Silane-A has a low viscosity of around 2cSt at 25°C.
- Silane-A which was obtained directly from a commercial silane manufacturing unit were measured. Light stripping removed low boiling point components from Silane-A such as 1- octene and octene isomers to obtain a high purity Silane-A product, i.e., a high amount of octyltriethoxysilane. The results were:
- Silane-A already had very high purity.
- Silane-A showed high color, i.e., color above 30 pt-co, due to the presence of platinum.
- Silane-A needed a heavy distillation step for removing platinum and color by distilling the product and leaving platinum in a heavy stream to separate the Silane-A product and platinum.
- product yield was lost since some of the product remained in the heavy stream and became waste.
- a distillation process requires significant energy consumption due to the heating and vacuum required, which causes significant additional manufacturing costs.
- the additional heavy distillation step reduced product yield and significantly increased final product cost.
- Example 6 the fixed-bed adsorption unit with the above-discussed specifications was used to treat the Silane-A at a specific temperature and residence time.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
Abstract
La présente invention concerne un procédé de récupération d'un catalyseur à base de métal précieux dans un milieu de réaction liquide contenant un produit organosilicium, ledit milieu de réaction contenant un catalyseur à base de métal précieux.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2011/034499 WO2012148415A1 (fr) | 2011-04-29 | 2011-04-29 | Procédé de récupération de métal précieux et élimination de couleur dans milieu de réaction liquide contenant un produit organosilicium |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2011/034499 WO2012148415A1 (fr) | 2011-04-29 | 2011-04-29 | Procédé de récupération de métal précieux et élimination de couleur dans milieu de réaction liquide contenant un produit organosilicium |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012148415A1 true WO2012148415A1 (fr) | 2012-11-01 |
Family
ID=44072556
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2011/034499 WO2012148415A1 (fr) | 2011-04-29 | 2011-04-29 | Procédé de récupération de métal précieux et élimination de couleur dans milieu de réaction liquide contenant un produit organosilicium |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2012148415A1 (fr) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2109908A5 (fr) * | 1970-10-01 | 1972-05-26 | Dow Corning | |
EP0367492A2 (fr) * | 1988-10-31 | 1990-05-09 | Rhone-Poulenc Surfactants And Specialties, L.P. | Procédé d'élimination de catalyseurs solubles à base de platine de mélanges liquides |
FR2765215A1 (fr) * | 1997-06-27 | 1998-12-31 | Rhodia Chimie Sa | Procede de decoloration d'un produit, notamment d'une huile silicone, comprenant des residus catalytiques colores |
US6013187A (en) * | 1998-08-31 | 2000-01-11 | Dow Corning Corporation | Method for removing metal contaminants from solution using mercapto-functional silica xerogels |
WO2006013060A1 (fr) | 2004-08-04 | 2006-02-09 | Phosphonics Ltd | Organopolysiloxanes substitues et utilisation |
-
2011
- 2011-04-29 WO PCT/US2011/034499 patent/WO2012148415A1/fr active Application Filing
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2109908A5 (fr) * | 1970-10-01 | 1972-05-26 | Dow Corning | |
EP0367492A2 (fr) * | 1988-10-31 | 1990-05-09 | Rhone-Poulenc Surfactants And Specialties, L.P. | Procédé d'élimination de catalyseurs solubles à base de platine de mélanges liquides |
FR2765215A1 (fr) * | 1997-06-27 | 1998-12-31 | Rhodia Chimie Sa | Procede de decoloration d'un produit, notamment d'une huile silicone, comprenant des residus catalytiques colores |
US6013187A (en) * | 1998-08-31 | 2000-01-11 | Dow Corning Corporation | Method for removing metal contaminants from solution using mercapto-functional silica xerogels |
WO2006013060A1 (fr) | 2004-08-04 | 2006-02-09 | Phosphonics Ltd | Organopolysiloxanes substitues et utilisation |
EP1786850A1 (fr) | 2004-08-04 | 2007-05-23 | Phosphonics LTD | Organopolysiloxanes substitues et utilisation |
US20090098082A1 (en) | 2004-08-04 | 2009-04-16 | Phosphonics Ltd | substiuted organopolysiloxanes and use thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2701820B1 (fr) | Procédé de récupération de métaux précieux et élimination de la couleur à partir d'un milieu de réaction liquide contenant un produit organosilicium | |
JPH0319237B2 (fr) | ||
JPH0328295A (ja) | 液体炭化水素化合物中の水銀の除去方法 | |
JPS63290886A (ja) | 水素含有シロキサンの精製法 | |
KR20090115126A (ko) | 수성 담배 추출물 구성성분의 선택적 제거방법 및 장치 | |
WO2016069450A2 (fr) | Procédé, méthode et système d'élimination de métaux lourds à partir de fluides | |
WO2012148415A1 (fr) | Procédé de récupération de métal précieux et élimination de couleur dans milieu de réaction liquide contenant un produit organosilicium | |
CN108570335A (zh) | 轻石脑油脱硫脱胺的方法和装置 | |
CN1865263A (zh) | 不对称烯烃硅氢加成制备β-加成物的方法 | |
US8137565B2 (en) | Naphthenic acid removal and conversion | |
CN111225880A (zh) | 硼的去除方法、及纯水或超纯水的制造方法 | |
Bai | Manufacturing of platinum-and color-free organosilicon products using heterogeneous platinum catalysts | |
JPS6212231B2 (fr) | ||
CA2929405C (fr) | Utilisation d'un materiau hybride organique-inorganique pour extraire l'uranium(vi) d'une solution aqueuse d'acide sulfurique, issue notamment de la lixiviation sulfurique d'un minerai uranifere | |
JP2978251B2 (ja) | 液状炭化水素中の水銀の除去方法 | |
JP3812661B2 (ja) | シリコーン油の精製法 | |
JP2001226681A (ja) | 蒸留済み炭化水素留分中の水銀およびヒ素の捕集方法 | |
JPH06171909A (ja) | イオウ精製法 | |
WO2024079637A1 (fr) | Élimination de silicones et d'autres impuretés dans de l'huile de pyrolyse à l'aide de matrices de gel de silice | |
AU2012233962B2 (en) | Method for estimating content of fine particles in slurry and process for producing hydrocarbon oil | |
WO2023091908A1 (fr) | Procédés et systèmes de décontamination d'huile de pyrolyse à l'aide d'unités modulaires | |
WO2024117894A1 (fr) | Système et procédé d'élimination de produits chimiques toxiques d'huiles végétales | |
JPH0762136B2 (ja) | 液状炭化水素中の水銀の除去方法 | |
WO2020232114A1 (fr) | Procédés de séchage d'oxyde de propylène | |
US20010050246A1 (en) | Process for capturing mercury and arsenic comprising evaporation then condensation of a hydrocarbon-containing cut |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11718634 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 11718634 Country of ref document: EP Kind code of ref document: A1 |