WO2007119614A1 - 媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 - Google Patents
媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 Download PDFInfo
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- WO2007119614A1 WO2007119614A1 PCT/JP2007/057116 JP2007057116W WO2007119614A1 WO 2007119614 A1 WO2007119614 A1 WO 2007119614A1 JP 2007057116 W JP2007057116 W JP 2007057116W WO 2007119614 A1 WO2007119614 A1 WO 2007119614A1
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- halogenated aromatic
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- aromatic compound
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
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- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
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- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
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- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/006—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents of waste oils, e.g. PCB's containing oils
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M175/00—Working-up used lubricants to recover useful products ; Cleaning
- C10M175/0008—Working-up used lubricants to recover useful products ; Cleaning with the use of adsorbentia
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/1062—Lubricating oils
Definitions
- the present invention collects a halogenated aromatic compound contained in an organic medium typified by insulating oil, machine oil, heat medium, lubricating oil, plasticizer, paint and ink, and mixtures thereof.
- the present invention relates to a selective fixing agent that can be used, and a method for selectively collecting a halogenated aromatic compound using the same.
- Halogenated aromatic compounds are compounds that are highly toxic to the human body, animals and plants, and are specified by laws on the treatment and cleaning of waste as hazardous substances, especially because of the potential for teratogenicity. There are many. When these compounds are present in soil, groundwater, incineration ash, wash water, machine oil, etc., it is strictly specified that some treatment must be applied to reduce their concentration below the standard value.
- an organic medium such as an insulating oil containing a halogenated aromatic compound has been chemically treated as it is (Patent No. 2611900, Patent No. 3247505).
- PCB polychlorobiphenyls
- reclaimed oil without PCBB certificate From certified insulating oils (new oils and reclaimed oils), organic media containing trace amounts of halogenated aromatic compounds (about 0.5-lOOppm, especially about 0.5-10ppm) have been confirmed one after another.
- the chemical treatment of such a large amount of organic medium by the conventional method requires a lot of time and useful energy, so that there remains a problem efficiently and economically.
- halogenated aromatic compound treatment technique not only a medium containing a trace amount of a halogenated aromatic compound but also a technique for treating a halogenated aromatic compound itself has been established.
- high concentration (1% or more) of halogenated aromatic compounds A process (hereinafter referred to as “high-concentration treatment”) for directly processing a high-concentration-containing medium to be contained has begun to operate (Japanese Patent Laid-Open No. 2003-112034).
- the medium from which the halogenated aromatic compound has been removed can be used as a non-contained medium, and it can open the way for use and can save the storage place of the medium before processing.
- Japanese Patent Application Laid-Open No. 5-31212 discloses a method for collecting an organic halogen compound that forms an organic halogen compound inclusion complex using a modified cyclodextrin.
- the method described in JP-A-5-31212 relates to a method of collecting an organic halogen compound contained in an aqueous solution using the hydrophilic modified cyclodextrin, and uses the modified cyclodextrin that is not lipophilic. It is difficult to apply the method as it is to organic medium systems.
- the present inventors can selectively fix the halogenated aromatic compound by interacting with the halogenated aromatic compound contained in the organic medium in an attractive manner.
- the present invention selectively fixes a halogenated aromatic compound contained in an organic medium, and removes or concentrates the halogenated aromatic compound from the organic medium, whereby only the halogenated aromatic compound is obtained. It is an object of the present invention to provide a selective fixing agent that makes it easy to decompose the material.
- the present invention also provides a method for selectively collecting halogenated aromatic compounds contained in an organic medium using a strong selective fixing agent. Aspects of the present invention are as follows:
- Rl is an amino group, an alkyl group, an alkenyl group, an alkynyl group, a halogen atom, a haloalkyl group, a aryleno group, an aralkyl group, an alkoxyalkyl group, a nitro group, an alkanoinole group, an aroyl group, an alkoxycarbonyl group, Aryloxycarbonyl group, alkoxy group, haloalkoxy group, aryloxy group, aralkyloxy group, alkoxyalkyloxy group, alkanoyloxy group, alkoxycarbonyloxy group, aralkyloxycarbonyloxy group, alkylsilyl group, or alkyl Represents a silyloxy group, and n is 6, 7 or 8)
- Halogenated aromatic compound strength The selective fixing agent according to 1 or 2 above, which is dioxins, polybiphenyl, or polybenzene.
- organic medium is selected from the group consisting of insulating oil, heat medium, lubricating oil, plasticizer, paint and ink, and mixtures thereof.
- a compound that interacts with the halogenated aromatic compound in an aspiration is cyclodextrin 5.
- the selective fixing agent according to any one of 1 to 4 above, which is a supramolecular assembly.
- R1 is an amino group, an alkyl group, an alkenyl group, an alkynyl group, a halogen atom, a noble alkyl group, an aryleno group, an aralkyl group, an alkoxyalkyl group, a nitro group, an alkanoinole group, an aryloyl group, an alkoxycarbonyl group, Aryloxycarbonyl group, alkoxy group, haloalkoxy group, aryloxy group, aralkyloxy group, alkoxyalkyloxy group, alkanoyloxy group, alkoxycarbonyloxy group, aralkyloxycarbonyloxy group, alkylsilyl group, or alkyl Represents a silyloxy group, and n is 6, 7 or 8)
- the organic medium is mixed with a halogenated aromatic compound selected from the group consisting of a mixture of two or more of acyclic compounds and a selective fixing agent containing a composition containing a compound that interacts with suction.
- Halogenated aromatic compounds contained in A compound that attracts and interacts with the compound and then separates the compound that interacts with the halogenated aromatic compound to which the halogenated aromatic compound is attracted from the organic medium.
- a method for collecting a halogenated aromatic compound contained in an organic medium To And a method for collecting a halogenated aromatic compound contained in an organic medium.
- Halogenated aromatic compound power The method according to 7 or 8 above, wherein the compound is dioxins, polybiphenyl, or polybenzene.
- organic medium is selected from the group consisting of insulating oil, machine oil, heat medium, lubricating oil, plasticizer, paint and ink, and mixtures thereof.
- halogenated aromatic compound refers to all compounds in which an aromatic compound is substituted with one or more of fluorine, chlorine, bromine and iodine. In the present invention, it refers to, for example, polychlorinated biphenyls (PCB), dioxins, chlorofluorocarbons, and polychlorinated benzenes.
- PCB polychlorinated biphenyls
- dioxins refer to specific compounds specified by the Special Measures Law against Dioxins in a narrow sense, but the present invention includes all halogenated compounds suspected as so-called endocrine disruptors (environmental hormones).
- the “organic medium” containing a halogenated aromatic compound generally refers to an organic solvent, particularly an organic solvent that dissolves a halogenated aromatic compound well, and more specifically, From the mode of use, it means insulating oils, machine oils, heat media, lubricating oils, plasticizers, paints and inks, and mixtures thereof that are highly likely to contain halogenated aromatic compounds.
- the “organic medium” means that most of the organic medium (for example, 60% or more) may contain water depending on the case, and contains the halogenated aromatic compound.
- the nature of the organic medium as a whole is not limited to aqueous solutions. It is that of an organic solution.
- halogenated aromatic compounds contained in solid substances for example, paper, wood, incinerated ash, rocks, soil, etc.
- What is extracted and transferred to an organic medium can also be an “organic medium containing a halogenated aromatic compound” to be treated with the selective fixing agent of the present invention.
- a compound that interacts with a halogenated aromatic compound in an attractive manner interacts with the above-mentioned halogenated aromatic compound in an attractive manner (that is, not repulsive). This refers to all compounds having a cyclic moiety, substituent, sequence, etc., and can be either a cyclic compound or an acyclic compound.
- a compound that interacts with a halogeno-aromatic compound in an aspiration is sometimes simply abbreviated as “aspiration interaction compound,” “an interaction compound,” or “an compound that interacts.” May be described.
- “selectively fixing” a halogenated aromatic compound means that only the halogenated aromatic compound contained in the organic medium by dissolution, dispersion, or the like, or the halogenated aromatic compound is contained inside. It interacts with the association of organic medium molecules contained in and incorporates or fixes it.
- “adhesion” includes all of chemical bonding and adhesion as well as physical adsorption and suction, or simply in a state of being pulled, and means that the material is not necessarily bonded constantly. I don't mean.
- the “selective sticking agent” of the present invention means that the active ingredient contained in the selective sticking agent interacts with the halogenated aromatic compound contained in the organic medium strongly and attractively, and the halogenated aromatic compound is In addition to drugs that firmly incorporate or settle into the molecular structure of the active ingredient, force, or active ingredient is in a state of at least temporary contact with a halogenated aromatic compound. Means a drug that can.
- the selective fixing agent of the present invention includes a composition capable of fixing these by attracting interaction with the halogenated aromatic compound.
- Active ingredients in the composition As the following formula 1:
- R1 is an amino group, an alkyl group, an alkenyl group, an alkynyl group, a halogen atom, a noble alkyl group, an aryleno group, an aralkyl group, an alkoxyalkyl group, a nitro group, an alkanoinole group, an aryloyl group, an alkoxycarbonyl group, Aryloxycarbonyl group, alkoxy group, haloalkoxy group, aryloxy group, aralkyloxy group, alkoxyalkyloxy group, alkanoyloxy group, alkoxycarbonyloxy group, aralkyloxycarbonyloxy group, alkylsilyl group, or alkyl Represents a silyloxy group, and n is 6, 7 or 8)
- the compounds that interact with the halogenated aromatic compounds exemplified here are cyclic moieties, substituents, and sugar sequences that can interact with the halogenated aromatic compounds in the molecular structure.
- it is a compound having a peptide sequence and the like, and can be dispersed at least in an organic medium.
- the portion that interacts with suction and the halogenated aromatic compound interact to fix the halogenated aromatic compound at or near the interacting portion.
- a compound that interacts with a halogenated aromatic compound in an attractive manner is tert- An alkyl group such as a til group, an alkyl-modified aryl group such as a triphenylmethyl group, or an alkylsilyl group such as a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group, or a triisopropylsilyl group.
- Cyclic compounds such as ⁇ -, ⁇ - or y-cyclodextrin compounds substituted with hydroxyl groups, cyclophane compounds, azacyclophane compounds, thiocyclophane compounds, crown compounds, or calixarene compounds, and cyclic / non-cyclic having specific sugar sequences
- Examples include oligosaccharides or cyclic Z acyclic oligopeptides having a specific peptide sequence.
- Particularly preferred compounds for the purposes of the present invention are mono-, beta- or gamma-cyclodextrins (hereinafter "TBDMS-hiichi CD", “TBDMS-j3-”) modified with a tert-butyldimethylsilyl group.
- CD or“ TBDMS_y_CD ”
- a cyclodextrin supramolecular assembly
- a supramolecular assembly of cyclodextrins is used in the present specification to refer to an aggregate in which several molecules spontaneously assemble due to weak interactions between molecules ("intermolecular force").
- the f column Channel type cyclodextrin described in J Inclusion Compound Formation with a New olumnar Cyciodextrm Host, Langmuir 2002, 18, 10016-10023, and the like.
- a channel-type cyclodextrin is a cylindrical shape (channel shape) formed by aggregating a plurality of cyclodextrins, and various applications have been tried from the shape.
- the present inventors have found that a channel-type cyclodextrin is a compound that interacts with a halogenated aromatic compound in an attractive manner, and has applied it as a selective fixing agent for a halogenated aromatic compound.
- the composition used for the selective fixing agent of the present invention includes, as an active ingredient, a compound that interacts with the halogenated aromatic compound as described above, and, if necessary, a carrier, a substrate, Auxiliaries such as diluents can be included.
- the compound that interacts with the halogenated aromatic compound, which is an active ingredient, in an attractive manner may optionally be immobilized on a carrier or a substrate.
- an organic medium for example, silica gel, polymer beads, ion exchange resin, glass, filter, membrane, various network structures.
- a solid carrier such as a lattice structure, foam or porous material. It can be used as an active ingredient of the agent.
- Immobilization of a compound that interacts with a halogenated aromatic compound to the support or base material can be carried out by a hydrophobic interaction in addition to a relatively strong chemical bond such as a covalent bond or ion bond. It can also be performed by physical interaction with relatively weak force and force, such as Van Der Ruska.
- the selective fixing agent of the present invention can selectively fix a halogenated aromatic compound contained in an organic medium and remove it from the organic medium.
- the method for collecting the halogenated aromatic compound contained in the organic medium using the selective sticking agent of the present invention is to introduce and disperse the selective sticking agent in the organic medium and disperse it by stirring or the like.
- the selective fixing agent of the present invention when a substance in which a compound that interacts with a halogenated aromatic compound is attracted to various solid supports is used, the halogenated aromatic compound contained in the organic medium is continuously added. Can be removed.
- the organic medium containing the halogenated aromatic compound used in the present invention contains at least one halogenated aromatic compound described above, and the content of the halogenated aromatic compound is particularly 0.5-. In the case of about 1%, it is said that it contains “very small amount”, “small amount” or “low concentration”. Organic media containing a low concentration of halogenated aromatics, while the amount of halogenated aromatics to be treated is very small, the volume of the organic media itself is very large and therefore difficult to store. Chemical processing takes a lot of time .
- a halogenated aromatic compound dissolved in a very small amount can be concentrated and separated from an organic medium and separated into a halogenated aromatic compound to be treated and a reusable organic medium, the halogenated aromatic compound can be separated. While the processing efficiency of the compound is increased, the problem of storage of such organic medium can be solved.
- An organic medium such as an insulating oil, a machine oil, a heat medium, a lubricating oil, a plasticizer, a paint and an ink containing a halogenated aromatic compound, or a mixture thereof is placed in a reaction vessel.
- the present invention includes a compound that interacts with the halogenated aromatic compound in an attractive manner 10 times to 50 times, preferably 50 to 200 times (molar basis) of the halogenated aromatic compound contained therein. Add the selective fixing agent and stir well.
- a compound that interacts with a halogenated aromatic compound, which is an active ingredient in the selective fixing agent of the present invention, or a composition containing such a compound is dispersed in an organic medium, and the halogen contained in the organic medium.
- the halogenated aromatic compound is fixed to or near the part by the interaction with the attractive interaction part in the compound that interacts with the halogenated aromatic compound.
- concentration of the halogenated aromatic compound, and the amount of the selective fixing agent of the present invention it is generally possible to contact by a method such as stirring for 5 hours to several days. it can.
- the fixing reaction can be suitably performed at room temperature, and can be heated as necessary.
- the halogenated aromatic compound contained in the organic medium is fixed to the compound that interacts with the halogenated aromatic compound in an attractive manner, the halogenated aromatic compound is fixed. Only the interaction compound or the composition containing the compound is separated.
- existing solid-liquid separation technology can be used. Examples include centrifuges and pressure filters.
- the filter used for separation can be a commercially available filter, glass filter, membrane, absorbent cotton, metal, resin or the like. If the inclusion compound contained in the selective fixing agent of the present invention has a pore size capable of separating, a filter, a membrane, or a membrane may be used. In consideration of the above, it is preferable to use one having a pore diameter of about 0 • 1_100 ⁇ m.
- the attractive interaction compound to which the halogenated aromatic compound obtained by separation is fixed is indispensable. If necessary, only the fixed halogenated aromatic compound is desorbed, and the halogenated aromatic compound fixed to the interaction compound or the halogenated aromatic compound obtained by the desorption operation is diluted as necessary. Thereafter, the decomposition treatment can be performed by a chemical treatment method such as a chemical extraction decomposition method.
- the organic medium obtained after separating the attractive interaction compound to which the halogenated aromatic compound is fixed the halogenated aromatic compound is substantially completely removed. Therefore, the organic medium that had been stored in the past because it contains a halogenated aromatic compound can be reused, or the reusable one can be reused or incinerated by ordinary methods. Can be discarded.
- the selective fixing agent of the present invention for example, silica gel, polymer beads, ion exchange resins, foams, films, membranes, various lattice-like structures are used as compounds that interact with the halogenated aromatic compound that is an active ingredient.
- a carrier such as a material, a net-like structure, or a porous material can be suitably used.
- a solid support such as silica gel, polymer beads, or ion exchange resin carrying the attractive interaction compound of the present invention is laminated in a column, and an organic medium containing a halogenated aromatic compound is usually used here.
- the organic medium containing the halogenated aromatic compound is filtered at normal pressure or under reduced pressure using a solid support such as a filter or a membrane supported on the suction interaction compound of the present invention. It is possible to remove the halogenated aromatic compound by fixing the halogenated aromatic compound contained in the membrane or filter.
- a solid support such as a foam, a net-like structure, a lattice-like structure, or a porous material that is loaded with the attractive interaction compound of the present invention is put into an organic medium containing a halogenated aromatic compound.
- the organic medium is absorbed in the net-like portion, lattice-like portion, or pore portion of the solid support, the contained halogenated aromatic compound is fixed, and then pressure is applied to the solid support (for example, squeezing, etc.)
- the organic medium from which the halogenated aromatic compound has been removed can be obtained.
- the compound that interacts with the halogenated aromatic compound of the present invention in a suction manner is fixed.
- the composition immobilized on a body carrier is used not only for removing halogenated aromatic compounds from an organic medium containing a halogenated aromatic compound by batch treatment, but also for methods for continuous treatment. Is preferably used.
- ⁇ -cyclodextrin 5.0 g, 4.4 mmol, Wako Pure Chemical Industries
- dry pyridine 44 ml, Wako Pure Chemical Industries
- TBDMSC1 tert-butyldimethylsilyl chloride
- TBDMS- ⁇ _CD (18 mg) synthesized in Synthesis Example 1 was placed in a 3 mL sample tube.
- Insulating oil 90 mg of Taniguchi Oil Refinery, including TCB
- TCB 1,2,4_triclo-necked benzene
- the Sampnore tube was attached to a shaker set to a water temperature of 25 ° C and shaken for 15 hours.
- TCB 1,2,4_triclo-necked benzene
- Example 1 was repeated except that 1,4-dichlorobenzene (hereinafter referred to as “DCB”, Wako Pure Chemical Industries) was used instead of TCB in Example 1.
- DCB 1,4-dichlorobenzene
- the obtained insulating oil was 175 mg, and the concentration of DCB contained in the insulating oil was measured by gas chromatography. DCB was not detected.
- TBDMS- ⁇ -CD (32 mg) synthesized in Synthesis Example 1 was placed in a 3 mL sample tube.
- Insulating oil containing 1Olppm of 4_chlorobiphenyl (hereinafter referred to as “CBP”, manufactured by Tokyo Chemical Industry Co., Ltd.) (Taniguchi Oil Refinery, 233 mg including CBP) was added to the above-mentioned Sampnore tube.
- the sample tube was attached to a shaker set to a water temperature of 25 ° C and shaken for 15 hours. Next, when the solution was poured into a simple separator made by filling absorbent cotton at the tip of the injector and separated by pushing a syringe, 177 mg of insulating oil was obtained.
- the concentration of CBP contained in the insulating oil is determined using the QCMS-QP5050 (Shimadzu Corporation) equipment, using M / Z 188, the selected ion detection method (SIM method), and the internal standard method (internal standard substance: 2_black). CBP was not detected.
- ⁇ -cyclodextrin ( ⁇ -CD, Wacker) (45 g) placed in a 500 ml eggplant flask was dissolved in deionized water (200 ml) and stirred at 50 ° C. for 20 hours.
- the ⁇ _CD aqueous solution was added dropwise to vigorously stirred acetone (1.251).
- the precipitated crystals were filtered with suction, and the obtained crystals were washed with acetone and naturally dried for 3 days. 46.45g channel type ⁇ -CD force S was obtained.
- 1,2,4-Trichlorodiethylbenzene (1,2,4-TCB) adjusted to 1 OOppm after putting the channel type ⁇ -CD (174 mg) prepared in Synthesis Example 2 into a 3 ml sample tube Insulating oil containing (309 mg) was added to the Sampnore tube. The sample tube was attached to a shaker set to a water temperature of 25 ° C and shaken. Twenty-four hours later, the solution was poured into a syringe with a cotton pad and poured out, and 115 mg of insulating oil was obtained. When the 1,2,4-TCB concentration of the insulating oil was measured by gas chromatography, it did not contain 1,2,4_TCB.
- 1,3,5-Trichlorobenzene (1,3,5_1 ⁇ 8) adjusted to 1 OOppm after putting the channel type ⁇ -CD (201 mg) prepared in Synthesis Example 2 into a 3 ml sample tube Insulating oil (3001 ⁇ ) was added to the sample. Shake the sample tube at a water temperature of 25 ° C. It was attached to the vessel and shaken. After 39 hours, the solution was poured into a syringe filled with cotton and dispensed to obtain 88 mg of insulating oil. When the 1,3,5-TCB concentration of the insulating oil was measured by gas chromatography, 1,3,5-TCB was not included.
- 1,2,4_Trichloroguchi benzene (Tokyo Kasei Kogyo Co., Ltd., purity 98% or more), 1,3,5-Trichloroguchi benzene (Tokyo Kasei Kogyo Co., Ltd., purity 98% or more), 4-chlorobiphenyl (Tokyo Kasei) Engineering Co., Ltd., purity 98% or higher), high-pressure insulating oil (Taniguchi Oil Refinery Co., Ltd.)
- TCB, MCBP and DCBP concentrations were measured by the internal standard method.
- GC-2010 SHIMADZU
- 4-MCBP, 2-MCBP, 4, 4'-DCBP, and 3, 4, 4'-TRCBP are measured using QCMS-QP5050 (SHIMADZU), M / Z 188, 188, respectively.
- 222 and 256 were used for measurement by SIM (Selective Ion Monitoring) method.
- an insulating oil, a heat medium, a lubricating oil which can contain a halogenated aromatic compound which is a toxic substance such as dioxins and polychlorobiphenyls that cannot be easily released to the environment
- a halogenated aromatic compound which is a toxic substance such as dioxins and polychlorobiphenyls that cannot be easily released to the environment
- Industries that must store organic media such as plasticizers, paints and inks, and solid substances such as paper, wood, incinerated ash, rocks, and soil that can contain these compounds.
- safe and efficient decomposition of these compounds and saving of storage space for such media can be realized at the same time.
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008510898A JP5147070B2 (ja) | 2006-04-14 | 2007-03-30 | 媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 |
US12/226,276 US20090294369A1 (en) | 2006-04-14 | 2007-03-30 | Selective Fixing Agents for Halogenated Aromatic Compounds Contained in Media and Method for Selective Fixing |
CN2007800223756A CN101506324B (zh) | 2006-04-14 | 2007-03-30 | 介质中含有的芳香族卤化物的选择性固定剂及选择性固定方法 |
EP07740552.0A EP2017317B1 (en) | 2006-04-14 | 2007-03-30 | Use of selective adsorbents for halogenated aromatic compounds contained in organic media and method of capturing of said halogenated aromatic compounds |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009095785A (ja) * | 2007-10-18 | 2009-05-07 | Neos Co Ltd | 媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 |
JP2010247083A (ja) * | 2009-04-16 | 2010-11-04 | Neos Co Ltd | 媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 |
JP2020526655A (ja) * | 2017-07-19 | 2020-08-31 | 中国石油化工股▲ふん▼有限公司 | シクロトリベラトリレン、およびその誘導体を含むオレフィン重合触媒 関連出願への相互参照 本出願は、中国特許出願番号201710591148.0、201710591173.9、201710592381.0、201710592384.4、201710592385.9、201710592383.x、201710591181.3、201710591859.8、201710591855.x、201710592386.3、201710592398.6(2017年7月19日出願)に基づく優先権を主張するものであり、その全体が全ての目的のために、参照により本明細書に組み込まれる。 |
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CN101638721B (zh) * | 2009-08-21 | 2011-06-08 | 北京大学 | 一种从水相中萃取分离铯离子的方法 |
EP3252030B1 (en) | 2016-05-30 | 2018-10-17 | Scg Chemicals Co. Ltd. | Process for purification of hydrocarbons |
EP3251741A1 (en) | 2016-05-30 | 2017-12-06 | Scg Chemicals Co. Ltd. | Adsorbent for hydrocarbon purification |
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- 2007-03-30 KR KR1020087027834A patent/KR20090010200A/ko not_active Application Discontinuation
- 2007-03-30 US US12/226,276 patent/US20090294369A1/en not_active Abandoned
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009095785A (ja) * | 2007-10-18 | 2009-05-07 | Neos Co Ltd | 媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 |
JP2010247083A (ja) * | 2009-04-16 | 2010-11-04 | Neos Co Ltd | 媒体に含有されるハロゲン化芳香族化合物の選択固着剤及び選択固着方法 |
JP2020526655A (ja) * | 2017-07-19 | 2020-08-31 | 中国石油化工股▲ふん▼有限公司 | シクロトリベラトリレン、およびその誘導体を含むオレフィン重合触媒 関連出願への相互参照 本出願は、中国特許出願番号201710591148.0、201710591173.9、201710592381.0、201710592384.4、201710592385.9、201710592383.x、201710591181.3、201710591859.8、201710591855.x、201710592386.3、201710592398.6(2017年7月19日出願)に基づく優先権を主張するものであり、その全体が全ての目的のために、参照により本明細書に組み込まれる。 |
JP7038797B2 (ja) | 2017-07-19 | 2022-03-18 | 中国石油化工股▲ふん▼有限公司 | シクロトリベラトリレン、およびその誘導体を含むオレフィン重合触媒 |
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JP5147070B2 (ja) | 2013-02-20 |
EP2017317B1 (en) | 2013-06-12 |
EP2017317A4 (en) | 2010-02-24 |
US20090294369A1 (en) | 2009-12-03 |
CN101506324B (zh) | 2012-12-26 |
EP2017317A1 (en) | 2009-01-21 |
KR20090010200A (ko) | 2009-01-29 |
JPWO2007119614A1 (ja) | 2009-08-27 |
CN101506324A (zh) | 2009-08-12 |
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