JP2006257034A - ハロゲン化芳香族化合物の脱ハロゲン化用溶媒、及びハロゲン化芳香族化合物の脱ハロゲン化方法 - Google Patents
ハロゲン化芳香族化合物の脱ハロゲン化用溶媒、及びハロゲン化芳香族化合物の脱ハロゲン化方法 Download PDFInfo
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- halogenated aromatic
- aromatic compound
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- 239000002904 solvent Substances 0.000 title claims abstract description 97
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000005658 halogenation reaction Methods 0.000 title abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000002480 mineral oil Substances 0.000 claims abstract description 28
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 28
- 239000011593 sulfur Substances 0.000 claims abstract description 28
- 235000010446 mineral oil Nutrition 0.000 claims abstract description 27
- 239000003921 oil Substances 0.000 claims abstract description 24
- 238000005695 dehalogenation reaction Methods 0.000 claims description 49
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 150000003071 polychlorinated biphenyls Chemical class 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004458 analytical method Methods 0.000 claims description 7
- 230000000382 dechlorinating effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 38
- 238000002156 mixing Methods 0.000 abstract description 3
- 238000004904 shortening Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000010998 test method Methods 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- -1 alkyl naphthalene Chemical compound 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000002699 waste material Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 150000002898 organic sulfur compounds Chemical class 0.000 description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
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- 239000000470 constituent Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000010735 electrical insulating oil Substances 0.000 description 2
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- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- RZNAUCXHYSSBOQ-UHFFFAOYSA-N 1,1'-biphenyl dihydrochloride Chemical compound Cl.Cl.C1(=CC=CC=C1)C1=CC=CC=C1 RZNAUCXHYSSBOQ-UHFFFAOYSA-N 0.000 description 1
- YSKHYETWIGVGRJ-UHFFFAOYSA-N 1,1'-biphenyl tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.c1ccc(cc1)-c1ccccc1 YSKHYETWIGVGRJ-UHFFFAOYSA-N 0.000 description 1
- FPRWVAMPWKGTNV-UHFFFAOYSA-N 1,2,3,4,5,6-hexahydroanthracene Chemical compound C1=CCCC2=C1C=C1CCCCC1=C2 FPRWVAMPWKGTNV-UHFFFAOYSA-N 0.000 description 1
- JPCYKCYTZCMDDD-UHFFFAOYSA-N 1,2,3,4,9,10-hexahydrophenanthrene Chemical compound C1CC2=CC=CC=C2C2=C1CCCC2 JPCYKCYTZCMDDD-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- MHMZSHBMMYKPTM-UHFFFAOYSA-N C(C=C1)=CC=C1C1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl Chemical compound C(C=C1)=CC=C1C1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl MHMZSHBMMYKPTM-UHFFFAOYSA-N 0.000 description 1
- RUEHNJKBTWNPLW-UHFFFAOYSA-N C(C=C1)=CC=C1C1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl.Cl Chemical compound C(C=C1)=CC=C1C1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl.Cl RUEHNJKBTWNPLW-UHFFFAOYSA-N 0.000 description 1
- LKNJXAOGEUWHBW-UHFFFAOYSA-N Cl.Cl.Cl.C1=CC=CC=C1C1=CC=CC=C1 Chemical compound Cl.Cl.Cl.C1=CC=CC=C1C1=CC=CC=C1 LKNJXAOGEUWHBW-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- Fire-Extinguishing Compositions (AREA)
- Processing Of Solid Wastes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】 本発明の溶媒は、ハロゲン化芳香族化合物の脱ハロゲン化に使用される溶媒であって、鉱油及び合成油から選ばれる少なくとも1種を含有し、硫黄分が350質量ppm以上であることを特徴とする。この溶媒と、ハロゲン化芳香族化合物と、脱ハロゲン化剤とを混合して所定温度に保持することにより、ハロゲン化芳香族化合物の脱ハロゲン化の反応効率を十分に向上させることができ、処理時間の短縮及び処理コストの削減が有効に実現可能となる。
【選択図】 なし
Description
(a−1)n−d−M環分析により得られる%CN値が20以上である鉱油又は合成油のうちの1種単独で又は2種以上の混合物で構成される溶媒。
(a−2)溶媒全体の%CN値が20以上となるように、%CN値が20以上である鉱油又は合成油と、%CN値が20未満である鉱油又は合成油とが混合された溶媒。
(a−3)溶媒全体の%CN値が20以上となるように、%CN値が20未満である鉱油又は合成油にナフテン環を有する化合物が添加された溶媒。
先ず、以下に示す溶媒1〜6を準備した。各溶媒の諸性状を表1に示す。
溶媒1:鉱油(硫黄分:400質量ppm、%CN値:56.2)
溶媒2:鉱油(硫黄分:400質量ppm、%CN値:54.5)
溶媒3:鉱油(硫黄分:900質量ppm、%CN値:28.7)
溶媒4:鉱油(硫黄分:8400質量ppm、%CN値:26.0)
溶媒5:鉱油(硫黄分:300質量ppm、%CN値:31.8)
溶媒6:鉱油(硫黄分:300質量ppm、%CN値:30.2)。
Claims (4)
- ハロゲン化芳香族化合物の脱ハロゲン化に使用される溶媒であって、鉱油及び合成油から選ばれる少なくとも1種を含有し、硫黄分が350質量ppm以上であることを特徴とする溶媒。
- n−d−M環分析により得られる%CN値が20以上であることを特徴とする、請求項1に記載の溶媒。
- 請求項1又は2に記載の溶媒と、ハロゲン化芳香族化合物と、脱ハロゲン化剤とを混合して所定温度に保持し、前記ハロゲン化芳香族化合物のハロゲン原子を水素原子に置換することを特徴とするハロゲン化芳香族化合物の脱ハロゲン化方法。
- 前記ハロゲン化芳香族化合物がポリ塩化ビフェニル類であり、前記脱ハロゲン化剤が脱塩素化剤であることを特徴とする、請求項3に記載のハロゲン化芳香族化合物の脱ハロゲン化方法。
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JP2005077979A JP4719489B2 (ja) | 2005-03-17 | 2005-03-17 | ハロゲン化芳香族化合物の脱ハロゲン化用溶媒、及びハロゲン化芳香族化合物の脱ハロゲン化方法 |
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JP2005077979A JP4719489B2 (ja) | 2005-03-17 | 2005-03-17 | ハロゲン化芳香族化合物の脱ハロゲン化用溶媒、及びハロゲン化芳香族化合物の脱ハロゲン化方法 |
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JP2006257034A true JP2006257034A (ja) | 2006-09-28 |
JP4719489B2 JP4719489B2 (ja) | 2011-07-06 |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4532028A (en) * | 1983-10-24 | 1985-07-30 | Niagara Mohawk Power Corporation | Method for reducing content of halogenated aromatics in hydrocarbon solutions |
US4910353A (en) * | 1983-02-07 | 1990-03-20 | Transformer Service, Inc. | Dehalogenation of polychlorinated biphenyls and other related compounds |
JPH08141107A (ja) * | 1994-11-15 | 1996-06-04 | Ebara Corp | ハロゲン化有機化合物の分解方法 |
JPH1128443A (ja) * | 1997-07-08 | 1999-02-02 | Nippon Soda Co Ltd | ハロゲン化合物の分解方法 |
JP2001047000A (ja) * | 1999-08-09 | 2001-02-20 | Idemitsu Kosan Co Ltd | ハロゲン化有機化合物含有物の処理方法 |
JP2006102014A (ja) * | 2004-10-04 | 2006-04-20 | Nuclear Fuel Ind Ltd | Pcbの化学処理方法 |
-
2005
- 2005-03-17 JP JP2005077979A patent/JP4719489B2/ja not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4910353A (en) * | 1983-02-07 | 1990-03-20 | Transformer Service, Inc. | Dehalogenation of polychlorinated biphenyls and other related compounds |
US4532028A (en) * | 1983-10-24 | 1985-07-30 | Niagara Mohawk Power Corporation | Method for reducing content of halogenated aromatics in hydrocarbon solutions |
JPH08141107A (ja) * | 1994-11-15 | 1996-06-04 | Ebara Corp | ハロゲン化有機化合物の分解方法 |
JPH1128443A (ja) * | 1997-07-08 | 1999-02-02 | Nippon Soda Co Ltd | ハロゲン化合物の分解方法 |
JP2001047000A (ja) * | 1999-08-09 | 2001-02-20 | Idemitsu Kosan Co Ltd | ハロゲン化有機化合物含有物の処理方法 |
JP2006102014A (ja) * | 2004-10-04 | 2006-04-20 | Nuclear Fuel Ind Ltd | Pcbの化学処理方法 |
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