JP5448018B2 - エチレングリコールの酸化防止方法 - Google Patents
エチレングリコールの酸化防止方法 Download PDFInfo
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- JP5448018B2 JP5448018B2 JP2006345702A JP2006345702A JP5448018B2 JP 5448018 B2 JP5448018 B2 JP 5448018B2 JP 2006345702 A JP2006345702 A JP 2006345702A JP 2006345702 A JP2006345702 A JP 2006345702A JP 5448018 B2 JP5448018 B2 JP 5448018B2
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- Prior art keywords
- ethylene glycol
- oxidation
- chemical formula
- preventing
- present
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- 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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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 106
- 230000003647 oxidation Effects 0.000 title claims description 22
- 238000007254 oxidation reaction Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 15
- 239000000126 substance Substances 0.000 claims description 16
- 150000003549 thiazolines Chemical class 0.000 claims description 13
- 230000002528 anti-freeze Effects 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000110 cooling liquid Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- -1 triazole compound Chemical class 0.000 description 2
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OUIAITHYQOIRPM-UHFFFAOYSA-N 4-methyl-1,3-thiazolidine-2-thione Chemical compound CC1CSC(=S)N1 OUIAITHYQOIRPM-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
試験例1
空気酸化によるエチレングリコールの劣化試験を次の操作で行い、その結果を下記にまとめた。エチレングリコール50gに、上記化2で表されるチアゾリン誘導体を重量比で所定量加えた。その後に酸化促進剤として銅粉を5g加え、エアレーションしながら100℃で30日間経時変化させた。そしてガスクロマトグラフィーによりエチレングリコールの残存量を測定した。ただし、下記実施例において、化2記載のR2〜R4は それぞれ水素である。
H 0.5 98.3
H 1.0 99.2
CH3 0.5 97.5
CH3 1.0 98.7
比較例 無添加 76.3
空気酸化による含水エチレングリコールの劣化試験を次の操作で行い、その結果を下記にまとめた。エチレングリコール25gと水25gからなる溶液に、上記化2で表されるチアゾリン誘導体をそれぞれ0.125g、0.25g(エチレングリコールに対して重量比で0.5%、1.0%)加えた。その後、試験例1と同様に酸化促進剤として銅粉を5g加え、エアレーションしながら100℃で30日間経時変化させた。なお、試験中に蒸発する水は、毎日、試験開始の状態になるように補充した。30日後、ガスクロマトグラフィーによりエチレングリコールの残存量を測定した。ただし、下記実施例において、化2記載のR1〜R4は それぞれ水素である。
0.5 96.7
1.0 98.3
比較例 無添加 76.3
空気酸化による自動車用不凍液の劣化試験を次の操作で行い、その結果を下記にまとめた。自動車用不凍液の例として、以下の配合で不凍液の類似液を調製した。エチレングリコール
88g、水 3.5g、セバシン酸3g、安息香酸ナトリウム 3g、ベンゾトリアゾール0.2g、トリルトリアゾール0.2g、2−メルカプトベンゾチアゾールのナトリウム塩0.1g、硝酸ナトリウム0.1g、モリブデン酸ナトリウム0.1g、水酸化カリウム1.8g。以上からなる溶液に、上記化2で表されるチアゾリン誘導体をそれぞれ0.44g、0.88g(エチレングリコールに対して重量比で0.5%、1.0%)加えた。
0.5 98.5
1.0 99.4
比較例 無添加 83.7
Claims (3)
Priority Applications (1)
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JP2006345702A JP5448018B2 (ja) | 2006-12-22 | 2006-12-22 | エチレングリコールの酸化防止方法 |
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JP2006345702A JP5448018B2 (ja) | 2006-12-22 | 2006-12-22 | エチレングリコールの酸化防止方法 |
Publications (3)
Publication Number | Publication Date |
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JP2008156263A JP2008156263A (ja) | 2008-07-10 |
JP2008156263A5 JP2008156263A5 (ja) | 2010-02-12 |
JP5448018B2 true JP5448018B2 (ja) | 2014-03-19 |
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JP2006345702A Active JP5448018B2 (ja) | 2006-12-22 | 2006-12-22 | エチレングリコールの酸化防止方法 |
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Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102135051B1 (ko) | 2013-04-11 | 2020-07-17 | 오사카 유키가가쿠고교 가부시키가이샤 | 1,2-알칸폴리올 함유 조성물 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53108909A (en) * | 1977-03-01 | 1978-09-22 | Mitsui Petrochem Ind Ltd | Purification of ethylene glycol |
JPS5783550A (en) * | 1980-11-12 | 1982-05-25 | Matsushita Electric Ind Co Ltd | High polymeric temperature-sensitive material |
JPH01163142A (ja) * | 1987-12-21 | 1989-06-27 | Mitsui Toatsu Chem Inc | 高純度モノエチレングリコールの製造方法 |
DE3824672C1 (ja) * | 1988-07-20 | 1990-04-05 | Deutsche Bp Ag, 2000 Hamburg, De | |
JPH0625655A (ja) * | 1992-03-09 | 1994-02-01 | Showa Kk | ブラインの再生方法及び装置 |
JP3310104B2 (ja) * | 1994-04-04 | 2002-07-29 | 三新化学工業株式会社 | 2−アミノチオフェノール類の製造方法 |
JPH09227425A (ja) * | 1996-02-15 | 1997-09-02 | Sanshin Chem Ind Co Ltd | エチレングリコールの安定化方法 |
US7442673B2 (en) * | 2003-08-15 | 2008-10-28 | Crompton Corporation | Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives |
-
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- 2006-12-22 JP JP2006345702A patent/JP5448018B2/ja active Active
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