Classifications

• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F1/00—Treatment of water, waste water, or sewage
  • C02F1/72—Treatment of water, waste water, or sewage by oxidation
  • C02F1/722—Oxidation by peroxides
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F1/00—Treatment of water, waste water, or sewage
  • C02F1/72—Treatment of water, waste water, or sewage by oxidation
  • C02F1/725—Treatment of water, waste water, or sewage by oxidation by catalytic oxidation
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2101/00—Nature of the contaminant
  • C02F2101/30—Organic compounds
  • C02F2101/38—Organic compounds containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
  • C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
  • C02F2103/346—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from semiconductor processing, e.g. waste water from polishing of wafers
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2209/00—Controlling or monitoring parameters in water treatment
  • C02F2209/02—Temperature
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2209/00—Controlling or monitoring parameters in water treatment
  • C02F2209/04—Oxidation reduction potential [ORP]
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2209/00—Controlling or monitoring parameters in water treatment
  • C02F2209/06—Controlling or monitoring parameters in water treatment pH
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2305/00—Use of specific compounds during water treatment
  • C02F2305/02—Specific form of oxidant
  • C02F2305/023—Reactive oxygen species, singlet oxygen, OH radical
• • C—CHEMISTRY; METALLURGY
  • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
  • C02F2305/00—Use of specific compounds during water treatment
  • C02F2305/02—Specific form of oxidant
  • C02F2305/026—Fenton's reagent

Definitions

• aspects and embodiments disclosed herein relate to systems and methods for the treatment of wastewater, for example, copper chemical-mechanical polishing (CMP) wastewater including organic contaminants such as azoles.
• CMP copper chemical-mechanical polishing
• the methods disclosed herein provide for the destruction of organic contaminants in the wastewater utilizing a modified Fenton’s reagent utilizing copper from combined waste streams of a semiconductor manufacturing facility as a catalyzing agent.
• a method for removing organic compounds from a copper-containing solution comprises producing the copper- containing solution from a mixture of wastewater from a copper chemical mechanical polishing (CMP) operation of a semiconductor manufacturing facility and a concentrated copper waste stream (CCW) from the semiconductor manufacturing facility; and introducing an oxidizer into the copper-containing solution, the copper catalyzing production of hydroxyl radicals from the oxidizer that react with the organic compounds.
• CMP copper chemical mechanical polishing
• CCW concentrated copper waste stream
• the method further comprises maintaining a pH of the copper- containing solution in the vessel at a level at which the copper catalyzes the production of the hydroxyl radicals from the oxidizer.
• the method further comprises maintaining the pH of the copper- containing solution in the vessel between about 2 and about 4.
• the method further comprises maintaining a temperature of the copper-containing solution in the vessel at between about 55°C and about 65°C.
• introducing the oxidizer into the copper-containing solution includes introducing hydrogen peroxide into the copper-containing solution.
• the method further comprises maintaining a concentration of hydrogen peroxide in the copper-containing solution in the vessel of 250 mg/L or more.
• the method further comprises obtaining the hydrogen peroxide from a waste stream from the semiconductor manufacturing facility.
• producing the copper-containing solution includes mixing at least one part of the CCW with 25 parts of the CMP wastewater or at least one part of the CCW with 10 parts of the CMP wastewater.
• removing the organic compounds from the copper-containing solution includes removing one or more azole compounds from the copper-containing solution.
• producing the copper-containing solution includes mixing the CCW with the CMP wastewater in an amount sufficient to provide 20 parts by weight copper per part by weight of the one or more azole compounds.
• removing the organic compounds from the copper-containing solution includes removing one or more of 1,2,4-Triazole, IH-Benzotriazole pyrazole, Benzotriazole, 5-methyl IH-benzotriazole (Tolutriazole), or 3-amino 1.2.4-triazole from the copper-containing solution.
• a system for removing organic compounds from wastewater from a semiconductor manufacturing facility comprising a vessel fluidly connectable to a source of the wastewater, a source of copper configured to introduce copper into the wastewater in the vessel, the source of copper including a concentrated copper waste stream from the semiconductor manufacturing facility; a source of oxidizer configured to introduce the oxidizer into the wastewater in the vessel, and a source of pH adjustment chemical configured to introduce the pH adjustment chemical into the wastewater in the vessel.
• the system further comprises a pH monitor disposed within the vessel, and a controller configured to control the source of pH adjustment chemical to introduce the pH adjustment chemical into the wastewater in the vessel at a quantity' and rate sufficient to maintain the pH of the wastewater at a level at which the copper catalyzes production of hydroxyl radicals from the oxidizer.
• the controller is configured to control the source of pH adjustment chemical to introduce the pH adjustment chemical into the wastewater in the vessel at a quantity and rate sufficient to maintain the pH of the wastewater at between about 2 and about 4.
• the system further comprises a heater, the controller further configured to control the heater to maintain a temperature of the wastewater in the vessel at between about 55°C and about 65°C.
• the source of oxidizer is a source of hydrogen peroxide
• the controller is further configured to control the source of oxidizer to maintain a concentration of hydrogen peroxide in the wastewater in the vessel at 250 mg/L or more.
• the source of hydrogen peroxide includes a waste stream of the semiconductor manufacturing facility.
• the wastewater includes one or more anti-corrosives for copper and the system is configured to decompose the anti -corrosives for copper with hydroxyl radicals produced from the oxidizer with the copper acting as a catalyst from the production of the hydroxyl radicals.
• the wastewater includes one or more azole compounds and the system is configured to decompose the one or more azoles with hydroxyl radicals produced from the oxidizer with the copper acting as a catalyst from the production of the hydroxyl radicals.
• the wastewater includes one or more of 1,2,4-Triazole, 1H- Benzotriazole pyrazole, Benzotriazole, 5-methyl IH-benzotriazole (Tolutriazole), or 3-amino 1,2,4-triazole and the system is configured to decompose the one or more of 1,2,4-Triazole, 1H- Benzotriazole pyrazole, Benzotriazole, Tolutriazole, or 3-amino 1,2,4-triazole with hydroxyl radicals produced from the oxidizer with the copper acting as a catalyst from the production of the hydroxyl radicals.
• the source of wastewater is a unit operation at the semiconductor manufacturing facility.
• the source of wastewater is a copper CMP operation at the semiconductor manufacturing facility.
• the source of copper includes a copper plating operation at the semiconductor manufacturing facility.
• FIG. 1 illustrates an example of a system as disclosed herein.
• the chemical mechanical polishing (CMP) planarization process involves a polishing slurry' comprising an oxidant, and abrasive, complexing agents, and additional additives to remove and/or etch semiconducting wafers during the manufacturing process.
• the polishing is performed with a polishing pad to remove excess copper from the semiconductor wafers. Silicon, copper, and various trace metals are removed from the silicon structure via the polishing slu '.
• the polishing slurry is introduced to the silicon wafer on a planarization table in conjunction with polishing pads. Oxidizing agents and etching solutions are introduced to control the removal of material.
• Deionized water rinses are generally employed to remove debris from the silicon wafer. UPW from reverse osmosis (RO), demineralized, and polished water may also be used in the semiconductor fabrication facility tools to rinse the silicon wafer.
• RO reverse osmosis
• H2O2 hydrogen peroxide
• An oxidizer of hydrogen peroxide (H2O2) typically is used to help dissolve the copper from the microchip. Accordingly, hydrogen peroxide (H2O2) at a level of about 300 ppm and higher also can be present in the byproduct polishing slurry wastewater.
• the azole-type anticorrosives for copper are chemically stable, even when using of an oxidizing agent having high oxidizing power, such as ozone, addition of a large amount thereof is required for oxidative decomposition of the azole- type anticorrosives for copper, thus posing a large problem in terms of cost.
• an oxidizing agent having high oxidizing power such as ozone
• addition of a large amount thereof is required for oxidative decomposition of the azole- type anticorrosives for copper, thus posing a large problem in terms of cost.
• the number of fine polishing steps has been increasing, and along with this, the amount of polishing wastewater discharged has been increasing. Therefore, the increase in cost due to an increase in the capacity of wastewater treatment equipment has become a problem.
• Fenton’s reagent is effective when treating some azoles, such as pyrazole.
• lab tests have shown that other forms of azoles such as 1,2,4-Triazole are not decomposed when exposed to Fenton’s reagent.
• azoles are often used in facilities that manufacture computer chips as an anticorrosive additive. These facilities also generally have high strength copper bearing wastewaters from the CMP process that, once spent, are treated and disposed of at a cost to the facility.
• the use of a waste copper stream in place of iron in Fenton’s reagent (a Fenton’s-like reagent) is used to treat and degrade azole compounds in wastewater. Testing has shown that 1,2,4-Triazole.
• copper is substituted for iron in a modified Fenton’s reaction, referred to herein as a Fenton’s-like reaction.
• a waste copper stream from a semiconductor production facility may be used as the source of the copper.
• the w aste copper may be present in the effluent of a copper CMP process, referred to as slurry copper w aste (SCW) herein.
• SCW slurry copper w aste
• a combined SCW and concentrated copper waste (CCW) stream may be used as a source of copper for producing a Fenton’s-like reagent (using Cu as a catalyst for the production of hydroxy radicals from H2O2 instead of iron as in a traditional Fenton’s reagent) for the treatment of azoles, metals (e.g., copper, cobalt, and iron), and silica solids in wastewater.
• the two wastewaters are blended at a 1 :25 ratio (CCW: SCW) or greater, for example, a 1: 10 ratio (CCW: SCW) or greater.
• additional copper for example, in the form of a copper sulfate solution, may be added to the combined CCW/SCW to provide additional copper to act as a catalyst in the Fenton’s-like reaction.
• the combined CCW/SCW or the combined CCW/SCW after dosing with additional copper may include 5,000 mg/L of dissolved copper or more, for example, 6,000 mg/L or 7,000 mg/L or more of dissolved copper or a ratio of up to 10: 1, 15: 1, or 20: 1 copper: azoles by weight or more in the wastewater to be treated.
• the wastewater from semiconductor manufacturing facilities or other industrial sources may include high levels of azoles, for example, from about 20 mg/1 up to about 200 mg/1 total azoles or greater, that are used as anticorrosive agents for copper during the wafer planarization and polishing process.
• the wastewater from these processes may also include heavy metals, additional organic compounds, for example, alcohols, and/or surfactants such as ammonium salts, and inorganic abrasives, such as colloidal silica, all of which should be removed prior to discharge of the wastewater.
• additional contaminants may be present at levels from about 0.01 wt% up to about 1 wt%.
• the wastewater may further have a high background total organic carbon (TOC) concentration, with the total azoles comprising a portion of the TOC.
• TOC total organic carbon
• oxidizers such as hydrogen peroxide (H2O2) are generally used to assist in dissolving copper from microchips and may be present in CMP wastewater at concentrations exceeding 1,000 mg/L or 0.1 wt%.
• Azoles are not currently regulated for maximum contaminant levels (MCL) by regulator ⁇ ' authorities in the United States but are believed to have a negative impact on the environment upon discharge into open waterways. Recent evidence has indicated bioaccumulation of azoles in fish and incidences of toxicity of naturally occurring algae blooms, necessitating their removal from process water before discharge.
• MCL maximum contaminant levels
• azole compounds are widely used in the semiconductor industry as anticorrosive agents for copper during silicon wafer processing.
• examples of such azole compounds include, but are not limited to, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, selenazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5- oxadiazole.
• azole derivatives include compounds having a fused ring of an azole ring and a benzene ring or the like, such as indazole, benzimidazole, benzotriazole, and benzothiazole, and further include derivatives thereof, such as alkylbenzotriazoles (e.g., benzotriazole, o-tolyltriazole, m-tolyl tri azole, -lolvltnazole. 5-ethylbenzotriazole.
• alkylbenzotriazoles e.g., benzotriazole, o-tolyltriazole, m-tolyl tri azole, -lolvltnazole. 5-ethylbenzotriazole.
• a semiconductor manufacturing facility 110 typically includes hundreds of unit operations, three of which are identified in FIG. 1.
• the unit operations identified in FIG. 1 are a copper CMP unit operation 120, a unit operation 130 that produces wastewater with a high concentration of dissolved copper, for example, a copper plating operation, and a unit operation 140 that produces wastewater having a high concentration of hydrogen peroxide, for example, one of the wafer cleaning unit operations within the semiconductor manufacturing facility 110.
• the disclosed system is utilized to decompose organic contaminants such as azoles present in wastewater from the copper CMP unit operation 120 utilizing a Fenton’ s-like reaction in which copper is utilized to catalyze the production of hydroxyl radicals from hydrogen peroxide.
• the hydroxyl radicals decompose the organic contaminants by oxidation into less objectional byproducts such as nitrogen oxides (NO2/NO3), carbon dioxide, and water.
• Wastewater from the CMP unit operation 120 is directed into a vessel 150, for example, by a pump Pl.
• An oxidizer for example, hydrogen peroxide from a source of oxidizer 160 is added to the wastew ater in the vessel 150, for example, using another pump P4 in an amount and at a rate sufficient to maintain a concentration of hydrogen peroxide in the vessel at a desired level, for example, 300 mg/L or greater, to facilitate reactions resulting in decomposition of organic compounds in the wastewater.
• the addition of oxidizer from the source of oxidizer 160 may be supplemented by the addition of hydrogen peroxide-containing wastewater from the unit operation 140, for example, using pump P3. If the hydrogen peroxide- containing wastewater from the unit operation 140 includes sufficient hydrogen peroxide, it may be utilized as the sole source of hydrogen peroxide added to the wastewater in the vessel 150.
• a persulfate salt such as ammonium persulfate, potassium persulfate, and/or sodium persulfate, may be utilized as the oxidizer. Aspects and embodiments disclosed herein are not limited by the type of oxidant added in the treatment system. Peroxides produce hydroxyl and hydroperoxyl radicals and persulfates produce persulfate radicals when reacting with dissolved copper in the vessel 150.
• a source of pH adjustment chemical 170 for example, a source of sulfuric acid and/or sodium hydroxide may add pH adjustment agent into the wastewater in the vessel 150 in an amount and at a rate sufficient to maintain the pH of the wastewater in the vessel at a desired level, for example, between 2 and 4 or about 3 to facilitate reactions resulting in decomposition of organic compounds in the wastew ater.
• a heater or heat exchanger 210 may also be present in the vessel and may be used to maintain the temperature of the wastewater in the vessel at a temperature suitable to facilitate decomposition of organic compounds such as azoles in the wastewater via a Fenton’s-like reaction within a desired timeframe.
• This temperature may be, for example, between 55°C and 65°C or about 60°C.
• the w astew ater from the CMP unit operation 120 may include sufficient copper, for example, in the form of copper sulfate, to catalyze production of hydroxyl radicals from the hydrogen peroxide in the vessel 150 in a Fenton’s-like reaction which will decompose one or more organic species in the wastewater in the vessel 150.
• Byproducts of the decomposition of the organic contaminants such as nitrogen oxides (NO2/NO3) and carbon dioxide may exit the vessel 150 through a vent V.
• the one or more organic species may include one or more azoles, for example, one or more of 1,2,4-Triazole, IH-Benzotriazole, or Methylbenzotriazole: 4,5 Tolytriazole which may have been present in the wastewater from the CMP unit operation 120.
• the Fenton’s-like reagent used for the decomposition of the azoles may be formed by adding about 500 mg/1 to about 3.000 mg/1 of an oxidant, such as hydrogen peroxide or a persulfate salt, to about 50 mg/1 to about 300 mg/1 of a soluble copper compound (e g., copper (Cu 2+ ) sulfate).
• the persulfate salt and the hydroxyl, hydroperoxyl, and persulfate radicals formed by the oxidation of Cu 2+ or the reduction of Cu 3+ may react with and decompose the azoles in the CMP wastewater into primarily nitrogen oxides (NO2/NO3), carbon dioxide, and water.
• NO2/NO3 nitrogen oxides
• carbon dioxide carbon dioxide
• water water
• One or more sensors or monitors may be present in the vessel 150 in contact with the wastewater in the vessel.
• the one or more sensors S may be in communication with a controller 190.
• the controller 190 may be a conventional computer including a conventional processor, for example, a Core® processor from the Intel Corporation and running a conventional operating system such as one of the versions of Windows® from the Microsoft Corporation and programmed to perform the functions disclosed herein.
• the controller may optionally be or include a specially programmed controller such as an Application Specific Integrated Circuit (ASIC) programmed to perform the functions disclosed herein.
• ASIC Application Specific Integrated Circuit
• the controller 190 is programmed or otherwise configured to control the source of pH adjustment chemical 170 to introduce the pH adjustment chemical into the wastewater in the vessel 150 at a quantity and rate sufficient to maintain the pH of the wastewater at a level at which the copper catalyzes production of hydroxyl radicals from the oxidizer.
• the controller 190 may also control operation of the heat exchanger or heater 210 and any of the pumps P1-P7 to control, e.g., introduction of wastewater from the CMP unit operation 120, oxidizer from the source of oxidizer 160, CCW from the unit operation 130, hydrogen peroxide-containing wastewater from the unit operationl40, supplemental copper solution from the source 200, and removal of treated wastewater from the vessel 150.
• the wastewater from the CMP unit operation 120 may not contain sufficient copper to catalyze production of sufficient hydroxyl radicals for decomposition of organic contaminants in the wastewater from the CMP unit operation 120 to levels that are as low as might be desired.
• additional copper may be added to the wastewater in the vessel 150 from, for example, the unit operation 130 that produces the wastewater with the high concentration of dissolved copper (the CCW) through a pump P2 operated by the controller 190.
• the two wastewaters may be blended or introduced into the vessel 150 at a 1 :25 ratio (CCW:SCW) or greater, for example, a 1: 10 ratio (CCW: SCW) or greater.
• additional copper for example, in the form of a copper sulfate solution, may be added to the combined CCW/SCW from a source 200 of supplemental copper solution through, for example, another pump P7 to provide additional copper to act as a catalyst in the Fenton’s-like reaction.
• the combined CCW/SCW or the combined CCW/SCW after dosing with additional copper may include 5,000 mg/L of dissolved copper or more, for example, 6,000 mg/L or 7,000 mg/L or more of dissolved copper or a ratio of up to 10: 1, 15: 1, or 20: 1 copper: azoles by weight or more in the wastewater to be treated.
• Wastewater from which organic compounds have been removed by decomposition by a Fentons ’s-like reaction as disclosed herein in the vessel 150 may exit the vessel and be directed, for example, by a pump P6 into a post-treatment system 180.
• the post-treatment system 180 may be used to remove residual copper and other undesired components from the partially treated wastewater exiting the vessel 150 using methods known in the art and may produce treated water that may be discharged to the environment, recycled, or sent for further treatment or disposal.
• aspects and embodiments disclosed herein are also directed to a method for removing organic compounds, for example, one or more azoles from a copper-containing solution, for example, wastewater from a chemical mechanical polishing unit operation of a semiconductor manufacturing facility utilizing a Fenton’s-like reagent.
• the copper-containing solution may be produced from a mixture of wastewater from a copper chemical mechanical polishing (CMP) operation of the semiconductor manufacturing facility and a concentrated copper waste stream (CCW) from the semiconductor manufacturing facility.
• CMP copper chemical mechanical polishing
• CCW concentrated copper waste stream
• the method may include introducing an oxidizer into the copper-containing solution, the copper catalyzing production of hydroxyl radicals from the oxidizer that react with the organic compounds.
• the pH of the copper- containing solution in the vessel may be maintained at a level at which the copper catalyzes the production of the hydroxyl radicals from the oxidizer, for example between 2 and 4.
• the temperature of the copper-containing solution in the vessel may be maintained at between about 55°C and about 65°C.
• Introducing the oxidizer into the copper-containing solution may include introducing hydrogen peroxide into the copper-containing solution.
• the concentration of hydrogen peroxide in the copper-containing solution in the vessel may be maintained at 250 mg/L or more.
• the hydrogen peroxide may be obtained from a waste stream from the semiconductor manufacturing facility.
• Producing the copper-containing solution may includes mixing at least one part of the CCW with 25 parts of the CMP wastewater or at least one part of the CCW with 10 parts of the CMP wastewater.
• Producing the copper-containing solution may include combining the CCW with the CMP wastewater in an amount sufficient to provide 10 parts by weight copper per part by weight of the one or more azole compounds.
• Removing the organic compounds from the copper-containing solution may include removing one or more of 1,2,4-Triazole, IH-Benzotriazole, or Methylbenzotriazole: 4,5 Tolytriazole from the copper- containing solution.
• the 10: 1 blend removed more TOC than the 25: 1 blend but still only removed 32% TOC.
• the term ‘‘plurality” refers to two or more items or components.
• the terms “comprising,” “including,” “carry ing,” “having,” “containing,” and “involving.” whether in the written description or the claims and the like, are open-ended terms, i.e.. to mean “including but not limited to.” Thus, the use of such terms is meant to encompass the items listed thereafter, and equivalents thereof, as well as additional items. Only the transitional phrases “consisting of’ and “consisting essentially of,” are closed or semi-closed transitional phrases, respectively, with respect to the claims.

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• Chemical Kinetics & Catalysis (AREA)
• Treatment Of Water By Oxidation Or Reduction (AREA)
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