JP7380182B2 - Hydrogen sulfide scavenger - Google Patents
Hydrogen sulfide scavenger Download PDFInfo
- Publication number
- JP7380182B2 JP7380182B2 JP2019230490A JP2019230490A JP7380182B2 JP 7380182 B2 JP7380182 B2 JP 7380182B2 JP 2019230490 A JP2019230490 A JP 2019230490A JP 2019230490 A JP2019230490 A JP 2019230490A JP 7380182 B2 JP7380182 B2 JP 7380182B2
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- JP
- Japan
- Prior art keywords
- group
- hydrogen sulfide
- sulfide scavenger
- carbon atoms
- scavenger
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 49
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title claims description 48
- 239000002516 radical scavenger Substances 0.000 title claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 150000002506 iron compounds Chemical class 0.000 claims description 17
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 4
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- -1 O-substituted hydroxylamine Chemical class 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
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- 229920000642 polymer Polymers 0.000 description 3
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- NQRKYASMKDDGHT-UHFFFAOYSA-N (aminooxy)acetic acid Chemical compound NOCC(O)=O NQRKYASMKDDGHT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 description 1
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- VEHLXPKUFPLBNQ-UHFFFAOYSA-N 3-methylpenta-1,4-dien-3-ylbenzene Chemical compound C=CC(C)(C=C)C1=CC=CC=C1 VEHLXPKUFPLBNQ-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Description
本発明は、硫化水素の捕捉剤に関する。 The present invention relates to a hydrogen sulfide scavenger.
硫化水素は、生活環境における代表的な臭気物質であり、目、皮膚、粘膜等への刺激性も有する。硫化水素は、悪臭防止法に基づく特定悪臭物質の一つであり、大気中から除去することが求められている。 Hydrogen sulfide is a typical odor substance in the living environment, and is also irritating to the eyes, skin, mucous membranes, etc. Hydrogen sulfide is one of the specified malodorous substances based on the Offensive Odor Prevention Act, and is required to be removed from the atmosphere.
硫化水素を除去する方法としては、塩化第二鉄、硫酸第二鉄、若しくは酸化第二鉄等の３価の鉄化合物で硫化水素を酸化し、安定な鉄硫化物及び硫黄に化学変換して除去する方法が汎用されている（例えば、特許文献１参照）。 A method for removing hydrogen sulfide is to oxidize hydrogen sulfide with a trivalent iron compound such as ferric chloride, ferric sulfate, or ferric oxide, and chemically convert it into stable iron sulfide and sulfur. A method of removing it is widely used (for example, see Patent Document 1).
しかしながら、従来の方法では、捕捉速度が不十分であるという問題があった。 However, the conventional method has a problem in that the acquisition speed is insufficient.
本発明は、上記の背景技術に鑑みてなされたものであって、硫化水素を速やかに捕捉する硫化水素捕捉剤を提供することをその目的とする。 The present invention has been made in view of the above-mentioned background art, and an object of the present invention is to provide a hydrogen sulfide scavenger that quickly captures hydrogen sulfide.
本発明者らは、上記の課題を解決するため鋭意検討を重ねた結果、特定のカルボキシ基含有Ｏ－置換ヒドロキシルアミン又はこれらの化学的に許容される塩、及び３価の鉄化合物を含む硫化水素捕捉剤が、硫化水素を速やかに且つ持続的に捕捉することを見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have developed a sulfur compound containing a specific carboxy group-containing O-substituted hydroxylamine or a chemically acceptable salt thereof, and a trivalent iron compound. The inventors have discovered that a hydrogen scavenger can rapidly and sustainably capture hydrogen sulfide, and have completed the present invention.
すなわち、本発明は、以下の要旨を有するものである。 That is, the present invention has the following gist.
［１］カルボキシ基含有Ｏ－置換モノヒドロキシルアミン又はその化学的に許容される塩、及び３価の鉄化合物を含む硫化水素捕捉剤。 [1] A hydrogen sulfide scavenger containing a carboxy group-containing O-substituted monohydroxylamine or a chemically acceptable salt thereof and a trivalent iron compound.
［２］下記一般式（１）で表されるカルボキシ基含有Ｏ－置換モノヒドロキシルアミン又はその化学的に許容される塩を１種以上含むことを特徴とする［１］に記載の硫化水素捕捉剤。 [2] The hydrogen sulfide capture method according to [1], which contains one or more carboxy group-containing O-substituted monohydroxylamine represented by the following general formula (1) or a chemically acceptable salt thereof. agent.
（式中、Ｒは水素原子、炭素数１～１８のアルキル基、炭素数６～１４のアリール基、又は炭素数７～１５のアリールアルキル基を表す。ｎは１～６の整数を表す。複数のＲは同一又は相異なっていてもよい。）
［３］一般式（１）において、Ｒが、水素原子、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ベンジル基、フェニル基のいずれかであることを特徴とする［２］に記載の硫化水素捕捉剤。
(In the formula, R represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 14 carbon atoms, or an arylalkyl group having 7 to 15 carbon atoms. n represents an integer of 1 to 6. (Plural R's may be the same or different.)
[3] In general formula (1), R is a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a benzyl group, a phenyl group. The hydrogen sulfide scavenger according to [2], which is any one of the above.
［４］３価の鉄化合物が、塩化第二鉄及び／又は硫酸第二鉄であることを特徴とする［１］乃至［３］に記載の硫化水素捕捉剤。 [4] The hydrogen sulfide scavenger according to [1] to [3], wherein the trivalent iron compound is ferric chloride and/or ferric sulfate.
［５］［１］乃至［４］に記載の硫化水素捕捉剤を使用することを特徴とする硫化水素の除去方法。 [5] A method for removing hydrogen sulfide, comprising using the hydrogen sulfide scavenger described in [1] to [4].
本発明の硫化水素捕捉剤は、硫化水素類を速やかに且つ持続的に捕捉する。その結果、人体に有害な硫化水素を低減し、ヒトの生活環境を改善することができる。 The hydrogen sulfide scavenger of the present invention rapidly and continuously captures hydrogen sulfides. As a result, hydrogen sulfide, which is harmful to the human body, can be reduced and the living environment of humans can be improved.
本発明の硫化水素捕捉剤は、カルボキシ基含有Ｏ－置換モノヒドロキシルアミン又はその化学的に許容される塩、及び３価の鉄化合物を含むことをその特徴とする。 The hydrogen sulfide scavenger of the present invention is characterized by containing a carboxy group-containing O-substituted monohydroxylamine or a chemically acceptable salt thereof, and a trivalent iron compound.
上記一般式（１）において、Ｒは水素原子、炭素数１～１８のアルキル基、炭素数６～１４のアリール基、又は炭素数７～１５のアリールアルキル基を表す。ｎは１～６の整数を表す。複数のＲは同一又は相異なっていてもよい。 In the above general formula (1), R represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 14 carbon atoms, or an arylalkyl group having 7 to 15 carbon atoms. n represents an integer from 1 to 6. A plurality of R's may be the same or different.
炭素数１～１８のアルキル基は、直鎖状、分岐状若しくは環状のアルキル基であってもよく、特に限定されないが、例えば、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基（セチル基）、ヘプタデシル基、オクタデシル基（ステアリル基）、オレイル基、エライジル基、イソプロピル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、３－メチルブチル基、２，２－ジメチルプロピル基、１，１－ジメチルプロピル基、２－エチルヘキシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロノニル基、シクロデシル基等が挙げられる。 The alkyl group having 1 to 18 carbon atoms may be a linear, branched, or cyclic alkyl group, and is not particularly limited, but includes, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group (cetyl group), heptadecyl group, octadecyl group (stearyl group), oleyl group, elaidyl group group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,1-dimethylpropyl group, 2-ethylhexyl group, cyclopropyl group, cyclobutyl group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, and the like.
炭素数６～１４のアリール基としては、特に限定されないが、例えば、フェニル基、ナフチル基、アントリル基、トリル基、キシリル基、クメニル基、ビニルフェニル基、ビフェニリル基、フェナントリル基等が挙げられる。 The aryl group having 6 to 14 carbon atoms is not particularly limited, but includes, for example, phenyl group, naphthyl group, anthryl group, tolyl group, xylyl group, cumenyl group, vinylphenyl group, biphenylyl group, phenanthryl group, and the like.
炭素数７～１５のアリールアルキル基としては、特に限定されないが、例えば、ベンジル基、フェニルエチル基、フェニルプロピル基、ナフチルメチル基、アントリルメチル基、トリルメチル基、キシリルメチル基、クメニルメチル基、ビニルフェニルメチル基、ビフェニリルメチル基、フェナントリルメチル基等が挙げられる。 The arylalkyl group having 7 to 15 carbon atoms is not particularly limited, but includes, for example, benzyl group, phenylethyl group, phenylpropyl group, naphthylmethyl group, anthrylmethyl group, tolylmethyl group, xylylmethyl group, cumenylmethyl group, vinylphenyl group. Examples include methyl group, biphenylylmethyl group, phenanthrylmethyl group, and the like.
これらのうち、一般式（１）において、Ｒが、水素原子、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ベンジル基、フェニル基のいずれかであるカルボキシ基含有Ｏ－置換モノヒドロキシルアミンが特に好ましい。 Among these, in general formula (1), R is a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a benzyl group, a phenyl group. Particularly preferred are carboxy group-containing O-substituted monohydroxylamines.
上記のカルボキシ基含有Ｏ－置換モノヒドロキシルアミンのヒドロキシルアミノ基は、一部又は全てが無機酸又は有機酸との化学的に許容される塩となっていてもよい。塩の種類としては、特に限定されないが、例えば、塩酸塩、臭化水素酸塩、過塩素酸塩、ケイ酸塩、テトラフルオロホウ酸塩、ヘキサフルオロリン酸塩、硫酸塩、硝酸塩、リン酸塩等の無機酸塩、酢酸塩、クエン酸塩、フマル酸塩、マレイン酸塩、トリフルオロメタンスルホン酸塩、トリフルオロ酢酸塩、安息香酸塩、トシル酸塩等の有機酸塩が挙げられ、安価である点で無機酸塩が好ましく、塩酸塩がさらに好ましい。 Part or all of the hydroxylamino group of the above-mentioned carboxy group-containing O-substituted monohydroxylamine may be a chemically acceptable salt with an inorganic acid or an organic acid. The type of salt is not particularly limited, but includes, for example, hydrochloride, hydrobromide, perchlorate, silicate, tetrafluoroborate, hexafluorophosphate, sulfate, nitrate, and phosphoric acid. Examples include inorganic acid salts such as salts, organic acid salts such as acetate, citrate, fumarate, maleate, trifluoromethanesulfonate, trifluoroacetate, benzoate, and tosylate, and are inexpensive. In this respect, inorganic acid salts are preferred, and hydrochlorides are more preferred.
また、上記のカルボキシ基含有Ｏ－置換モノヒドロキシルアミンのカルボキシ基は、分子内のヒドロキシルアミノ基と分子内塩を形成してもよい。さらに、当該カルボキシ基の一部がカルボン酸塩となっていてもよいが、本発明の硫化水素捕捉剤はアルカリ性になると捕捉効果が低下するため、ｐＨが７以下となる範囲でカルボン酸塩を形成することが好ましい。カルボン酸塩の種類としては、特に限定されないが、例えば、リチウム塩、ナトリウム塩、カリウム塩、セシウム塩等のアルカリ金属塩、アンモニウム塩等が挙げられる。 Furthermore, the carboxy group of the above-mentioned carboxy group-containing O-substituted monohydroxylamine may form an inner salt with a hydroxylamino group within the molecule. Further, a part of the carboxy group may be a carboxylate, but since the hydrogen sulfide scavenger of the present invention loses its scavenging effect when it becomes alkaline, a carboxylate may be used as long as the pH is 7 or less. It is preferable to form. The type of carboxylate salt is not particularly limited, but examples include alkali metal salts such as lithium salts, sodium salts, potassium salts, and cesium salts, ammonium salts, and the like.
３価の鉄化合物としては、特に限定されないが、例えば、塩化第二鉄や硫酸第二鉄が挙げられる。 Trivalent iron compounds include, but are not particularly limited to, ferric chloride and ferric sulfate.
本発明の硫化水素捕捉剤は、目的、用途に応じて任意の形態で使用することができる。例えば、カルボキシ基含有Ｏ－置換モノヒドロキシルアミン又はその化学的に許容される塩及び３価の鉄化合物（以下、「カルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物」という。）を任意の溶媒に溶解させて液状硫化水素捕捉剤として使用したり、カルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物又は前記の液状硫化水素捕捉剤を任意の担体に担持し、固体状硫化水素捕捉剤として使用することができる。 The hydrogen sulfide scavenger of the present invention can be used in any form depending on the purpose and use. For example, a carboxy group-containing O-substituted monohydroxylamine or a chemically acceptable salt thereof and a trivalent iron compound (hereinafter referred to as "carboxy group-containing O-substituted monohydroxylamine and trivalent iron compound") It can be used as a liquid hydrogen sulfide scavenger by dissolving it in any solvent, or it can be used as a solid hydrogen sulfide scavenger by supporting carboxy group-containing O-substituted monohydroxylamines and trivalent iron compounds or the liquid hydrogen sulfide scavenger on any carrier. Can be used as a hydrogen sulfide scavenger.
本発明の液状硫化水素捕捉剤を調製する際の溶媒へのカルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物の溶解量は、目的に応じて任意に調節可能であり、特に限定するものではないが、本発明の液状硫化水素捕捉剤に対して各々０．１～３０重量％の範囲が好ましく、１～２０重量％の範囲がさらに好ましい。 The amount of the carboxy group-containing O-substituted monohydroxylamine and the trivalent iron compound dissolved in the solvent when preparing the liquid hydrogen sulfide scavenger of the present invention can be arbitrarily adjusted depending on the purpose, and is not particularly limited. Although it is not a specific amount, it is preferably in the range of 0.1 to 30% by weight, and more preferably in the range of 1 to 20% by weight, based on the liquid hydrogen sulfide scavenger of the present invention.
本発明の固体状硫化水素捕捉剤を調製する際にカルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物を担持する担体としては、水に不溶性のものであれば特に制限なく用いることができる。例えば、高分子担体として、ポリスチレン、架橋ポリスチレン等のスチレン系ポリマー、ポリエチレン、ポリプロピレン等のポリオレフィン、ポリ塩化ビニル、ポリテトラフルオロエチレン等のポリ（ハロゲン化オレフィン）、ポリアクリロニトリル等のニトリル系ポリマー、ポリメタクリル酸メチル、ポリアクリル酸エチル等の（メタ）アクリル系ポリマー、セルロース、アガロース、デキストラン等の高分子量多糖類等が挙げられ、無機担体として、活性炭、シリカゲル、珪藻土、ヒドロキシアパタイト、アルミナ、酸化チタン、マグネシア、ポリシロキサン等が挙げられる。 When preparing the solid hydrogen sulfide scavenger of the present invention, the carrier supporting the carboxy group-containing O-substituted monohydroxylamine and the trivalent iron compound may be used without any particular restriction as long as it is insoluble in water. can. For example, as a polymer carrier, styrene polymers such as polystyrene and crosslinked polystyrene, polyolefins such as polyethylene and polypropylene, poly(halogenated olefins) such as polyvinyl chloride and polytetrafluoroethylene, nitrile polymers such as polyacrylonitrile, and Examples include (meth)acrylic polymers such as methyl methacrylate and polyethyl acrylate, and high molecular weight polysaccharides such as cellulose, agarose, and dextran.Inorganic carriers include activated carbon, silica gel, diatomaceous earth, hydroxyapatite, alumina, and titanium oxide. , magnesia, polysiloxane, etc.
ここで、架橋ポリスチレンとは、スチレン、ビニルトルエン、ビニルキシレン、ビニルナフタレン等のモノビニル芳香族化合物とジビニルベンゼン、ジビニルトルエン、ジビニルキシレン、ジビニルナフタレン、トリビニルベンゼン、ビスビニルジフェニル、ビスビニルフェニルエタン等のポリビニル芳香族化合物との架橋共重合体を主体とするものであり、これらの共重合体にグリセロールメタクリレート、エチレングリコールジメタクリレート等のメタクリル酸エステルが共重合されていてもよい。 Here, crosslinked polystyrene refers to monovinyl aromatic compounds such as styrene, vinyltoluene, vinylxylene, and vinylnaphthalene, and divinylbenzene, divinyltoluene, divinylxylene, divinylnaphthalene, trivinylbenzene, bisvinyldiphenyl, bisvinylphenylethane, etc. These copolymers are mainly composed of crosslinked copolymers with polyvinyl aromatic compounds, and methacrylic acid esters such as glycerol methacrylate and ethylene glycol dimethacrylate may be copolymerized with these copolymers.
本発明の固体状硫化水素捕捉剤の調製において用いられる担体の形状としては、特に限定されるものではないが、例えば、球状（例えば、球状粒子など）、粒状、繊維状、顆粒状、モノリスカラム、中空糸、膜状（例えば、平膜など）等の一般的に分離基材として使用される形状が利用可能であり、これらのうち、球状、膜状、粒状、顆粒状、又は繊維状のものが好ましい。球状、粒状、又は顆粒状担体は、カラム法やバッチ法で使用する際、その使用体積を自由に設定できることから、特に好ましく用いられる。球状、粒状、又は顆粒状担体の粒子サイズとしては、通常、平均粒径１μｍ～１０ｍｍの範囲のものを用いることができるが、２μｍ～１ｍｍの範囲が好ましい。 The shape of the carrier used in the preparation of the solid hydrogen sulfide scavenger of the present invention is not particularly limited, but examples include spherical (e.g., spherical particles), granules, fibers, granules, monolithic columns, etc. Shapes commonly used as separation substrates such as , hollow fibers, and membranes (e.g., flat membranes) can be used. Preferably. Spherical, granular, or granular carriers are particularly preferably used when used in a column method or a batch method, since the volume to be used can be freely set. As for the particle size of the spherical, granular, or granular carrier, those having an average particle size in the range of 1 μm to 10 mm can be used, but the average particle size is preferably in the range of 2 μm to 1 mm.
本発明の固体状硫化水素捕捉剤の調製において用いられる担体は多孔質でもよいし、無孔質でもよい。多孔質担体の平均細孔径としては、通常、１ｎｍ～１μｍのものを用いることができるが、硫化水素捕捉速度の点で１ｎｍ～３００ｎｍの範囲が好ましい。 The carrier used in the preparation of the solid hydrogen sulfide scavenger of the present invention may be porous or nonporous. The average pore diameter of the porous carrier can generally be 1 nm to 1 μm, but is preferably in the range of 1 nm to 300 nm from the viewpoint of hydrogen sulfide capture rate.
本発明の固体状硫化水素捕捉剤を調製する方法としては、特に限定するものではないが、例えば、本発明の液状硫化水素捕捉剤又はカルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物を担体に物理的に吸着させて固定化する方法が挙げられる。 The method for preparing the solid hydrogen sulfide scavenger of the present invention is not particularly limited; Examples include a method of physically adsorbing and immobilizing on a carrier.
カルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物を物理的に吸着させて固定化する方法としては、特に限定されないが、例えば、カルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物を水等の溶媒に溶解させ、次いで上記した担体を加え、カルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物を当該担体に含浸させて、さらに溶媒を留去する方法が挙げられる。 The method of physically adsorbing and immobilizing the carboxyl group-containing O-substituted monohydroxylamines and the trivalent iron compound is not particularly limited, but for example, the carboxyl group-containing O-substituted monohydroxylamines and the trivalent iron compound Examples include a method of dissolving the compound in a solvent such as water, then adding the above-mentioned carrier, impregnating the carrier with the carboxy group-containing O-substituted monohydroxylamine and the trivalent iron compound, and then distilling off the solvent. .
担体へのカルボキシ基含有Ｏ－置換モノヒドロキシルアミン類及び３価鉄化合物の担持量は、目的に応じて任意に調節可能であり、特に限定するものではないが、本発明に用いる担体に対して各々０．１～３０重量％の範囲が好ましく、１～２０重量％の範囲がさらに好ましい。 The amount of carboxy group-containing O-substituted monohydroxylamines and trivalent iron compounds supported on the carrier can be arbitrarily adjusted depending on the purpose, and is not particularly limited. Each amount is preferably in the range of 0.1 to 30% by weight, more preferably 1 to 20% by weight.
以下、本発明を具体的に説明するが、本発明はこれらの実施例に限定して解釈されるものではない。 The present invention will be specifically explained below, but the present invention should not be construed as being limited to these Examples.
実施例１
アミノオキシ酢酸と塩化第二鉄を各々３重量％含有する捕捉剤の水溶液を、円状ろ紙（直径１２５ｍｍ、アドバンテック製）に１０ｇ／ｍ２の割合で塗布し、室温で２４時間乾燥させた。このろ紙をテドラーバッグに封入して真空脱気し、２０ｐｐｍの硫化水素ガスを１Ｌ注入後、２５℃で放置した。１時間後、２時間後、及び３時間後のテドラーバッグ中の硫化水素濃度を検知管（ガステック製）で定量した。
Example 1
An aqueous solution of a scavenger containing 3% by weight each of aminooxyacetic acid and ferric chloride was applied to circular filter paper (diameter 125 mm, manufactured by Advantech) at a rate of 10 g/m 2 and dried at room temperature for 24 hours. This filter paper was sealed in a Tedlar bag and vacuum degassed, and after injecting 1 L of 20 ppm hydrogen sulfide gas, it was left at 25°C. The hydrogen sulfide concentration in the Tedlar bag after 1 hour, 2 hours, and 3 hours was determined using a detection tube (manufactured by Gastech).
比較例１
捕捉剤を用いないこと以外は実施例１と同様に実施した。
Comparative example 1
The same procedure as in Example 1 was carried out except that no scavenger was used.
比較例２
捕捉剤としてアミノオキシ酢酸のみを３重量％含有する水溶液を用いたこと以外は実施例１と同様に実施した。
Comparative example 2
The same procedure as in Example 1 was carried out except that an aqueous solution containing 3% by weight of only aminooxyacetic acid was used as the scavenger.
比較例３
捕捉剤として塩化第二鉄のみを３重量％含有する水溶液を用いたこと以外は実施例１と同様に実施した。
Comparative example 3
The same procedure as in Example 1 was carried out except that an aqueous solution containing only 3% by weight of ferric chloride was used as the scavenger.
実施例１及び比較例１～３の結果を表１及び図１に示した。表１、図１より明らかなように、本発明の硫化水素捕捉剤は既存の硫化水素捕捉剤と比較して高い硫化水素捕捉性能を示した。 The results of Example 1 and Comparative Examples 1 to 3 are shown in Table 1 and FIG. 1. As is clear from Table 1 and FIG. 1, the hydrogen sulfide scavenger of the present invention exhibited higher hydrogen sulfide scavenging performance than existing hydrogen sulfide scavengers.
実施例２
捕捉時間を２４時間としたこと以外は実施例１と同様に実施した結果、２４時間経過後も硫化水素濃度は０．１ｐｐｍ未満であり、本発明の硫化水素捕捉剤は長時間経過後も高い硫化水素捕捉性能を維持した。
Example 2
As a result of carrying out the same procedure as in Example 1 except that the trapping time was 24 hours, the hydrogen sulfide concentration was less than 0.1 ppm even after 24 hours, and the hydrogen sulfide scavenger of the present invention was high even after a long period of time. Maintained hydrogen sulfide capture performance.
本発明の硫化水素捕捉剤は、硫化水素を速やかに且つ持続的に捕捉する。その結果、人体に有害な硫化水素を低減し、ヒトの生活環境を改善することができる。 The hydrogen sulfide scavenger of the present invention rapidly and continuously captures hydrogen sulfide. As a result, hydrogen sulfide, which is harmful to the human body, can be reduced and the living environment of humans can be improved.
Claims (4)
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