JP4936503B2 - 汚れ防止方法 - Google Patents
汚れ防止方法 Download PDFInfo
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- JP4936503B2 JP4936503B2 JP2005255190A JP2005255190A JP4936503B2 JP 4936503 B2 JP4936503 B2 JP 4936503B2 JP 2005255190 A JP2005255190 A JP 2005255190A JP 2005255190 A JP2005255190 A JP 2005255190A JP 4936503 B2 JP4936503 B2 JP 4936503B2
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- piperidine
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- 238000000034 method Methods 0.000 title claims description 64
- 230000002265 prevention Effects 0.000 title description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 54
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 238000000746 purification Methods 0.000 claims description 15
- 238000011084 recovery Methods 0.000 claims description 15
- 238000003860 storage Methods 0.000 claims description 14
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 8
- GXELTROTKVKZBQ-UHFFFAOYSA-N n,n-dibenzylhydroxylamine Chemical compound C=1C=CC=CC=1CN(O)CC1=CC=CC=C1 GXELTROTKVKZBQ-UHFFFAOYSA-N 0.000 claims description 8
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 7
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 7
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 4
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 4
- FMMQDMHSGNXJSQ-UHFFFAOYSA-N n,n-diphenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)C1=CC=CC=C1 FMMQDMHSGNXJSQ-UHFFFAOYSA-N 0.000 claims description 4
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 claims description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 2
- -1 diene compounds Chemical class 0.000 description 69
- 229920000642 polymer Polymers 0.000 description 60
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 55
- 241000482268 Zea mays subsp. mays Species 0.000 description 55
- 150000001875 compounds Chemical class 0.000 description 39
- 230000000694 effects Effects 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 17
- 238000011109 contamination Methods 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 230000003373 anti-fouling effect Effects 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000007791 liquid phase Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 230000009422 growth inhibiting effect Effects 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000009036 growth inhibition Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- WSGDRFHJFJRSFY-UHFFFAOYSA-N 4-oxo-TEMPO Chemical group CC1(C)CC(=O)CC(C)(C)N1[O] WSGDRFHJFJRSFY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002519 antifouling agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000053 physical method Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- PHWAJJWKNLWZGJ-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Br)=C(O)C(Br)=C1 PHWAJJWKNLWZGJ-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
TEMPO:2,2,6,6−テトラメチル−ピペリジン−1−オキシル
HTEMPO:4−ヒドロキシ−2,2,6,6−テトラメチル−ピペリジン−1−オキシル
OTEMPO:4−オキソ−2,2,6,6−テトラメチル−ピペリジン−1−オキシル
DEHA:N,N−ジエチルヒドロキシルアミン
DBHA:N,N−ジベンジルヒドロキシルアミン
DPHA:N,N−ジフェニルヒドロキシルアミン
TBC:p−tert−ブチルカテコール
ステンレス製オートクレーブ(内容量0.1L)に2個の200メッシュのステンレス製カゴに実機より採取した1,3−ブタジエンのポップコーン・ポリマー(0.2g)を入れ、1個は気相部につるし、他の1個は液相部に浸漬した。オートクレーブを窒素置換した後、真空ポンプで十分脱気し、所定量のピペリジン−N−オキシル化合物とN,N−ジ置換ヒドロキシアミン化合物を精製1,3−ブタジエン(15g)に添加し、オートクレーブに入れた。更に純酸素と純窒素の混合ガス(酸素濃度100ppmに調整)を圧入し、ガス相の酸素濃度を5ppmに調整した。オートクレーブを65℃に加熱し、この温度を68時間加熱、維持した後、冷却してオートクレーブ中の気相部、液相部のポップコーン・ポリマーの重量を測定して成長倍数(試験開始前のポップコーン・ポリマー重量0.2gに対する試験後のポップコーン・ポリマー重量の比)を求め、ポップコーン・ポリマー成長抑制効果を評価した。
同様に表1記載のピペリジン−N−オキシル化合物および酸素あるいは従来の汚れ防止剤を添加してポップコーン・ポリマー成長抑制効果を評価した。その結果を表1に示した。
ピペリジン−1−オキシル化合物とN,N−ジ置換ヒドロキシルアミン化合物と酸素の併用によるポップコーン・ポリマーの成長抑制効果は、気相部、液相部ともピペリジン−1−オキシル化合物の単独使用(比較例3)、N,N−ジ置換ヒドロキシルアミン化合物の単独使用(比較例4)、N,N−ジ置換ヒドロキシルアミン化合物と酸素の併用(比較例5)、従来多用されたTBCの使用(比較例8,9)を上回る効果を発揮し、それぞれ単独よりも高い相乗効果を発揮していることが分かる。
「ポップコーン・ポリマー成長抑制試験」において、冷却したオートクレーブ中の気相部分の壁面および液相部分の底部あるいは壁面からポップコーン・ポリマーを採取し、その重量を測定して、新たな2個の200メッシュのステンレス製カゴに入れて、オートクレーブに設置した。新たにピペリジン−N−オキシル化合物とN,N−ジ置換ヒドロキシアミン化合物を添加せず、さらに酸素を圧入することなく、精製1,3−ブタジエン(15g)のみをオートクレーブに入れ、「ポップコーン・ポリマー成長抑制試験」と同様の手順でオートクレーブを65℃に加熱し、この温度を68時間維持した後、冷却してオートクレーブ中の気相部、液相部のポップコーン・ポリマーの重量を測定して成長倍数を求め、ポップコーン・ポリマー成長抑制効果を評価した。その結果を表2に示した。
Claims (1)
- 1,3−ブタジエン、2−メチル−1,3−ブタンジエン(イソプレン)、1,3−ペンタジエン、クロロプレンから選択される1種の製造工程、精製工程、回収工程、貯蔵工程あるいは輸送工程において、酸素存在下で、2,2,6,6−テトラメチル−ピペリジン−1−オキシル、4−ヒドロキシ−2,2,6,6−テトラメチル−ピペリジン−1−オキシルおよび4−オキソ−2,2,6,6−テトラメチル−ピペリジン−1−オキシルから選択される1種以上と同時に、N,N−ジエチルヒドロキシルアミン、N,N−ジベンジルヒドロキシルアミン、N,N−ジフェニルヒドロキシルアミンから選択される1種以上を用いることを特徴とする汚れ防止方法。
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JP2005255190A JP4936503B2 (ja) | 2005-09-02 | 2005-09-02 | 汚れ防止方法 |
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JP2005255190A JP4936503B2 (ja) | 2005-09-02 | 2005-09-02 | 汚れ防止方法 |
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JP2007063237A JP2007063237A (ja) | 2007-03-15 |
JP4936503B2 true JP4936503B2 (ja) | 2012-05-23 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2008189569A (ja) * | 2007-02-02 | 2008-08-21 | Hakuto Co Ltd | 共役ジエン化合物の重合抑制剤組成物および重合抑制方法 |
JP5660654B2 (ja) * | 2009-05-28 | 2015-01-28 | 伯東株式会社 | オイルクエンチ塔内部の気相部における汚れの成長を防止する方法 |
CN115210274A (zh) * | 2020-03-31 | 2022-10-18 | 陶氏环球技术有限责任公司 | 防污剂和方法 |
EP4414349A1 (en) * | 2021-10-04 | 2024-08-14 | Resonac Corporation | Method for producing hexafluoro-1,3-butadiene |
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JP3941151B2 (ja) * | 1997-03-11 | 2007-07-04 | 日本ゼオン株式会社 | 共役ジエン類の重合防止方法 |
JPH10251662A (ja) * | 1997-03-13 | 1998-09-22 | Nippon Zeon Co Ltd | 共役ジエン類の精製方法 |
JP3187345B2 (ja) * | 1997-07-29 | 2001-07-11 | 伯東株式会社 | オレフィン類製造あるいは精製工程の汚れ防止方法 |
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