JP2022031354A - モノマーの重合を制御及び抑制する組成物並びにその使用及び調製の方法 - Google Patents
モノマーの重合を制御及び抑制する組成物並びにその使用及び調製の方法 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 239000000178 monomer Substances 0.000 title claims abstract description 80
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 35
- -1 phenol compound Chemical class 0.000 claims abstract description 58
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000005977 Ethylene Substances 0.000 claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 12
- 230000003647 oxidation Effects 0.000 claims abstract description 11
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 11
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims description 17
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 13
- 238000004508 fractional distillation Methods 0.000 claims description 9
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 claims description 5
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 4
- PJZLSMMERMMQBJ-UHFFFAOYSA-N 3,5-ditert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC(O)=C(O)C(C(C)(C)C)=C1 PJZLSMMERMMQBJ-UHFFFAOYSA-N 0.000 claims description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000008021 deposition Effects 0.000 abstract description 8
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 25
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 18
- 239000000654 additive Substances 0.000 description 18
- 230000000996 additive effect Effects 0.000 description 14
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000010791 quenching Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000295 fuel oil Substances 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PJEKFSKIOOHJNR-UHFFFAOYSA-N 1h-indene;styrene Chemical compound C=CC1=CC=CC=C1.C1=CC=C2CC=CC2=C1 PJEKFSKIOOHJNR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
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- 230000002708 enhancing effect Effects 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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Abstract
Description
従って、本発明の主な目的は、スチレン、インデン、ジビニルベンゼン、α-メチルスチレン、及び他の高級環化合物若しくはモノマー、又はその誘導体を含みうるモノマーの重合を制御及び抑制するのに適し、かつ、従来技術の添加剤又はその個々の成分の用量と比較して比較的低用量でも重合抑制効率が同一か又はより優れる付加組成物を提供することである。
(a) カテコール化合物を含むフェノール化合物と、
(b1) 脂肪族第三級アミン及び/又は(b2)酸化処理されたその誘導体、好ましくは、前記脂肪族第三級アミンのアルキル鎖に1又はそれ以上のヒドロキシル基がある脂肪族第三級アミンと、
の組み合わせを含み、前記カテコール化合物を含むフェノール化合物の重合抑制効率の向上、及び/又は前記モノマーの重合を制御及び抑制する前記カテコール化合物を含むフェノール化合物の量の低減を目的とする組成物である。
(a) カテコール化合物を含むフェノール化合物と、
(b) 脂肪族第三級アミン、前記脂肪族第三級アミンの酸化処理された誘導体、又はそれらの混合物と、
の組み合わせを含む。
(a) カテコール化合物を含むフェノール化合物と、
(b) 脂肪族第三級アミン、前記脂肪族第三級アミンの酸化処理された誘導体、又はそれらの混合物と、
の組み合わせを含み、前記脂肪族第三級アミンはアルキル鎖に1又はそれ以上のヒドロキシル基を含む(又は有する)。
(i) トリ-イソプロパノールアミンのエチル酸化処理された誘導体(EO-TIPA)、
(ii) トリ-イソプロパノールアミンのプロピル酸化処理された誘導体(PO-TIPA)、又は
(iii) それらの混合物、
を含む。
熱分解ガソリン試料を窒素ガスパージ用のチューブ内で採取し、当該試料をおよそ90℃、およそ120℃及びおよそ150℃の温度でおよそ2時間処理した。そして形成したポリマーをメタノール沈殿で分離して、ブランク(添加剤を含まず)、比較試料(TBCからなる添加剤を100ppm含む)及び本発明の試料(40:10重量パーセントのTBCとTIPAを含む添加剤を100ppm含む)の重合パーセントを測定して、表-Iに示した。
Claims (14)
- モノマーの重合を制御及び抑制する付加組成物であって、前記組成物が以下の、
(a) カテコール化合物を含むフェノール化合物、
(b) 脂肪族第三級アミン、前記脂肪族第三級アミンの酸化処理された誘導体、又はそれらの混合物、
の組み合わせを含む、付加組成物。 - 前記脂肪族第三級アミンがアルキル鎖に1又はそれ以上のヒドロキシル基を含む、請求項1に記載の付加組成物。
- 前記脂肪族第三級アミンがアルキル鎖に3又はそれ以上のヒドロキシル基を含む、請求項1に記載の付加組成物。
- 前記脂肪族第三級アミンがトリ-イソプロパノールアミン(TIPA)を含む、上記請求項のいずれか一項に記載の付加組成物。
- 前記脂肪族第三級アミンの酸化処理された誘導体が以下の、
(i) トリ-イソプロパノールアミンのエチル酸化処理された誘導体(EO-TIPA)、
(ii) トリ-イソプロパノールアミンのプロピル酸化処理された誘導体(PO-TIPA)、又は
(iii) それらの混合物、
を含む、上記請求項のいずれか一項に記載の付加組成物。 - 前記フェノール化合物がカテコール化合物を含む、上記請求項のいずれか一項に記載の付加組成物。
- 前記カテコール化合物が第三ブチルカテコール(TBC)を含む、請求項6に記載の付加組成物。
- 前記第三ブチルカテコール(TBC)が、4-tert-ブチルカテコール;3,5-ジ-tert-ブチルカテコール、及びそれらの混合物を含む群から選択される、請求項7に記載の付加組成物。
- モノマーの重合を制御及び抑制する方法であって、前記方法が、請求項1~8のいずれか一項に記載の付加組成物でモノマーストリームを処理する工程を含む、方法。
- モノマーの重合を制御及び抑制するために請求項1~8のいずれか一項に記載の付加組成物を使用する方法であって、請求項1~8のいずれか一項に記載の付加組成物を使用する工程を含む、方法。
- 一次分留器(又はエチレンプラント)におけるモノマーの重合を制御及び抑制する方法であって、前記方法が、請求項1~8のいずれか一項に記載の付加組成物でモノマーストリームを処理する工程を含む、方法。
- 請求項1~8のいずれか一項に記載の付加組成物を使用することを含む、一次分留器(又はエチレンプラント)におけるモノマーの重合を制御及び抑制して一次分留器を作動させる方法。
- 請求項1~8のいずれか一項に記載の付加組成物でモノマーストリームを処理する工程を含む、一次分留器(又はエチレンプラント)におけるモノマーの重合を制御及び抑制して、一次分留器における付着及びポリマーの堆積物を低減させる方法。
- 一次分留器(又はエチレンプラント)におけるモノマーの重合を制御及び抑制して、一次分留器(又はエチレンプラント)における付着及びポリマーの堆積物を低減することで、一次分留器又はエチレンプラントのランレングスを延長する方法であって、請求項1~8のいずれか一項に記載の付加組成物でモノマーストリームを処理する工程を含む、方法。
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Application Number | Priority Date | Filing Date | Title |
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IN201721012339 | 2017-04-05 | ||
IN201721012339 | 2017-04-05 | ||
JP2019552506A JP2020515540A (ja) | 2017-04-05 | 2018-03-28 | モノマーの重合を制御及び抑制する組成物並びにその使用及び調製の方法 |
PCT/IB2018/052139 WO2018185613A1 (en) | 2017-04-05 | 2018-03-28 | Composition for control and inhibition of polymerization of monomers, and method of use and preparation thereof |
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JP2005213369A (ja) * | 2004-01-29 | 2005-08-11 | Hakuto Co Ltd | ファウリング防止剤およびファウリング防止方法 |
JP2014524504A (ja) * | 2011-08-26 | 2014-09-22 | ドルフ ケタール ケミカルズ(インド)プライベート リミテッド | スチレンの重合を抑制及び阻害する添加剤組成物、製造方法、並びにその使用 |
JP2014533774A (ja) * | 2011-11-29 | 2014-12-15 | ドルフ ケタール ケミカルズ(インド)プライベート リミテッドDorf Ketal Chemicals(India) Private Limited | スチレン重合を制御及び阻害するアミン系添加剤組成物、及びそれを使用する方法 |
JP2015500355A (ja) * | 2011-12-02 | 2015-01-05 | ドルフ ケタール ケミカルズ(インド)プライベート リミテッドDorf Ketal Chemicals(India) Private Limited | スチレンの重合の制御及び阻害のためのアミン及びニトロキシド系添加組成物、及びその使用方法 |
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US4628132A (en) | 1984-11-23 | 1986-12-09 | Atlantic Richfield Company | Composition and method for inhibiting formation of polymers during gas scrubbing of monomers |
US4638132A (en) * | 1985-10-28 | 1987-01-20 | Lectron Products, Inc. | Electrical pressure switch |
TWI469668B (zh) * | 2007-12-31 | 2015-01-11 | Interdigital Patent Holdings | 在cell_fach狀態中無線鏈結同步化及功率控制之方法及裝置 |
US9505988B2 (en) * | 2011-10-19 | 2016-11-29 | Nalco Company | Circulation aid for primary fractional quench loops |
RU2019129469A (ru) | 2017-04-05 | 2021-03-19 | Дорф Кетал Кемикалс (Индия) Прайвит Лимитэд | Композиция для регулирования и ингибирования полимеризации мономеров и способ ее применения и получения |
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JP2005213369A (ja) * | 2004-01-29 | 2005-08-11 | Hakuto Co Ltd | ファウリング防止剤およびファウリング防止方法 |
JP2014524504A (ja) * | 2011-08-26 | 2014-09-22 | ドルフ ケタール ケミカルズ(インド)プライベート リミテッド | スチレンの重合を抑制及び阻害する添加剤組成物、製造方法、並びにその使用 |
JP2014533774A (ja) * | 2011-11-29 | 2014-12-15 | ドルフ ケタール ケミカルズ(インド)プライベート リミテッドDorf Ketal Chemicals(India) Private Limited | スチレン重合を制御及び阻害するアミン系添加剤組成物、及びそれを使用する方法 |
JP2015500355A (ja) * | 2011-12-02 | 2015-01-05 | ドルフ ケタール ケミカルズ(インド)プライベート リミテッドDorf Ketal Chemicals(India) Private Limited | スチレンの重合の制御及び阻害のためのアミン及びニトロキシド系添加組成物、及びその使用方法 |
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TWI770158B (zh) | 2022-07-11 |
WO2018185613A1 (en) | 2018-10-11 |
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JP2020515540A (ja) | 2020-05-28 |
MY194124A (en) | 2022-11-14 |
TW201843130A (zh) | 2018-12-16 |
SG11201908734QA (en) | 2019-10-30 |
KR102399824B1 (ko) | 2022-05-19 |
CA3058137A1 (en) | 2018-10-11 |
RU2019129469A (ru) | 2021-03-19 |
BR112019020668A2 (pt) | 2020-05-05 |
CN110520402A (zh) | 2019-11-29 |
KR20190132647A (ko) | 2019-11-28 |
EP3606899A1 (en) | 2020-02-12 |
US11242303B2 (en) | 2022-02-08 |
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