JP2006500439A - 不飽和結合を含む炭化水素流中での粘度上昇及び汚損の抑制 - Google Patents
不飽和結合を含む炭化水素流中での粘度上昇及び汚損の抑制 Download PDFInfo
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- JP2006500439A JP2006500439A JP2004537632A JP2004537632A JP2006500439A JP 2006500439 A JP2006500439 A JP 2006500439A JP 2004537632 A JP2004537632 A JP 2004537632A JP 2004537632 A JP2004537632 A JP 2004537632A JP 2006500439 A JP2006500439 A JP 2006500439A
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- JP
- Japan
- Prior art keywords
- fouling
- butyl
- tert
- hydrocarbon stream
- viscosity increase
- 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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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G9/14—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils in pipes or coils with or without auxiliary means, e.g. digesters, soaking drums, expansion means
- C10G9/16—Preventing or removing incrustation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G75/00—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general
- C10G75/04—Inhibiting corrosion or fouling in apparatus for treatment or conversion of hydrocarbon oils, in general by addition of antifouling agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/949—Miscellaneous considerations
- Y10S585/95—Prevention or removal of corrosion or solid deposits
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
【化1】
Description
150℃で7.5時間加熱した後、熱分解軽油の粘度を20℃で測定した。3回の試験を実施した。第一はブランクであり、第二は1000ppmのフェニレンジアミンを含むものであり、第三は本発明方法に従って上記式(II)のキノンメチド1000ppmを含むものであった。下記の表1は、本発明のキノンメチドで処理した後の熱分解軽油の粘度が、フェニレンジアミンのみで処理した後より43.6%低く、オイルクエンチ塔内の条件をシミュレートした条件に熱分解軽油を暴露した後のブランクより55.1%低かったことを実証している。
表2に示した量の処理剤と共に144℃で6時間加熱した後、23℃での熱分解軽油の粘度を測定した。この表は、2000ppmの濃度までは、本発明のキノンメチド処理剤の濃度が高くなるほど粘度上昇の抑制が向上することを実証している。
150℃で7.5時間加熱した後、熱分解軽油試料中のポリマー含有量をメタノール沈殿で測定した。3回の試験を実施した。第一はブランクであり、第二は1000ppmのフェニレンジアミンを含むものであり、第三は本発明方法に従って上記式(II)のキノンメチド1000ppmを含むものであった。表3中の結果は、本発明のキノンメチドで処理した後の熱分解軽油試料のポリマー含有量が、フェニレンジアミンのみで処理した後より32.3%低く、オイルクエンチ塔内の条件をシミュレートした条件に熱分解軽油を暴露した後のブランクより40.0%低かったことを実証している。
表4に示した量の処理剤と共に144℃で6時間加熱した後、熱分解軽油試料中のポリマー含有量をメタノール沈殿で測定した。この表は、2000ppmの濃度までは、本発明のキノンメチド処理剤の濃度が高くなるほど、オイルクエンチ塔の条件をシミュレートした条件下で、熱分解軽油中に存在する炭化水素の重合の抑制が向上することを実証している。
150℃で8.0時間加熱した後、熱分解軽油試料中のポリマー含有量をメタノール沈殿で測定した。一つのブランク試料、及び表5に記載した処理剤1000ppmを含む試料を試験した。下記の表5は、本発明の式(II)及び(III)のキノンメチドで処理した試料のポリマー含有量がフェニレンジアミンで処理した試料のポリマー含有量より顕著に少なかったことを実証している。
Claims (10)
- 前記キノンメチドがエチレン製造中に炭化水素流に添加される、請求項1記載の方法。
- 前記キノンメチドが、汚損又は粘度上昇が起こり得る場所又はその上流で炭化水素流に添加される、請求項1記載の方法。
- 前記場所がオイルクエンチ塔である、請求項1記載の方法。
- 前記キノンメチドが、炭化水素を基準にして約1〜約10000ppmの量で添加される、請求項1記載の方法。
- 前記キノンメチドが、2,6−ジ−tert−ブチル−4−((3,5−ジ−tert−ブチル−4−ヒドロキシ−ベンジリデン)−シクロヘキサ−2,5−ジエノン、4−ベンジリデン−2,6−ジ−tert−ブチル−シクロヘキサ−2,5−ジエノン及びこれらの組合せからなる群から選択される1種である、請求項1記載の方法。
- 前記場所がオイルクエンチ塔である、請求項7記載の方法。
- 前記場所がオイルクエンチ塔の底部セクションである、請求項7記載の方法。
- 前記キノンメチドが、2,6−ジ−tert−ブチル−4−((3,5−ジ−tert−ブチル−4−ヒドロキシ−ベンジリデン)−シクロヘキサ−2,5−ジエノン、4−ベンジリデン−2,6−ジ−tert−ブチル−シクロヘキサ−2,5−ジエノン及びこれらの組合せからなる群から選択される1種である、請求項7記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/251,564 US6926820B2 (en) | 2002-09-20 | 2002-09-20 | Inhibition of viscosity increase and fouling in hydrocarbon streams including unsaturation |
US10/251,564 | 2002-09-20 | ||
PCT/US2003/023593 WO2004026995A1 (en) | 2002-09-20 | 2003-07-28 | Inhibition of viscosity increase and fouling n hydrocarbon streams including unsaturation |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006500439A true JP2006500439A (ja) | 2006-01-05 |
JP5166676B2 JP5166676B2 (ja) | 2013-03-21 |
Family
ID=31992769
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004537632A Expired - Lifetime JP5166676B2 (ja) | 2002-09-20 | 2003-07-28 | 不飽和結合を含む炭化水素流中での粘度上昇及び汚損の抑制 |
Country Status (12)
Country | Link |
---|---|
US (1) | US6926820B2 (ja) |
EP (1) | EP1543092B2 (ja) |
JP (1) | JP5166676B2 (ja) |
KR (1) | KR101097668B1 (ja) |
CN (1) | CN1304534C (ja) |
AT (1) | ATE381603T1 (ja) |
AU (1) | AU2003268035A1 (ja) |
DE (1) | DE60318223T3 (ja) |
ES (1) | ES2297192T5 (ja) |
MY (1) | MY129620A (ja) |
TW (1) | TWI282362B (ja) |
WO (1) | WO2004026995A1 (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7128826B2 (en) * | 2003-07-31 | 2006-10-31 | General Electric Company | Polymerization inhibitor for styrene dehydrogenation units |
DE602005015613D1 (de) * | 2004-11-16 | 2009-09-03 | Dow Global Technologies Inc | Elastomere zusammensetzungen mit erhöhter einschnürungsresistenz für hochgeschwindigkeits-blechextrudierungsanwendungen |
US7723398B2 (en) * | 2005-04-21 | 2010-05-25 | Ciba Specialty Chemicals Corporation | In-can stabilizer blend |
US8187346B2 (en) * | 2008-12-29 | 2012-05-29 | Fina Technology, Inc. | Stabilization of pygas for storage |
US8298440B2 (en) | 2010-06-03 | 2012-10-30 | General Electric Company | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
CN102254688B (zh) * | 2011-04-13 | 2012-12-26 | 清华大学 | 一种吡啶离子液体电解质及其制备方法和应用 |
US8884038B2 (en) | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
US9090526B2 (en) | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
US9206268B2 (en) | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
US8901362B2 (en) | 2012-02-02 | 2014-12-02 | General Electric Company | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
US9611336B2 (en) | 2012-10-25 | 2017-04-04 | Baker Hughes Incorporated | Quinone compounds for inhibiting monomer polymerization |
US9944577B2 (en) | 2012-10-25 | 2018-04-17 | Baker Hughes, A Ge Company, Llc | Hydroquinone compounds for inhibiting monomer polymerization |
DE102013204950A1 (de) | 2013-03-20 | 2014-09-25 | Evonik Industries Ag | Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen |
WO2020014606A1 (en) | 2018-07-13 | 2020-01-16 | Ecolab Usa Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
US11180578B2 (en) | 2018-07-13 | 2021-11-23 | Ecolab Usa Inc. | Polymerization inhibitor and retarder compositions with amine stabilizer |
WO2022182612A1 (en) * | 2021-02-26 | 2022-09-01 | Bl Technologies, Inc. | Composition and method for inhibiting the formation and growth of popcorn polymers |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH07166152A (ja) * | 1993-12-16 | 1995-06-27 | Hakuto Co Ltd | 炭化水素類の粘度上昇抑制剤およびその方法 |
JPH09165408A (ja) * | 1995-04-14 | 1997-06-24 | Ciba Geigy Ag | 7−アリールキノンメチドを用いる不飽和モノマーの抑制 |
JPH09176215A (ja) * | 1995-04-14 | 1997-07-08 | Ciba Geigy Ag | 不飽和モノマーのための阻害剤としての7−置換キノンメチド |
Family Cites Families (11)
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US4003800A (en) | 1976-01-02 | 1977-01-18 | Gulf Research & Development Company | Styrene purification process |
US4040911A (en) | 1976-01-02 | 1977-08-09 | Gulf Research & Development Company | Process for inhibiting the polymerization of styrene |
AU536979B2 (en) | 1982-04-26 | 1984-05-31 | Ppg Industries, Inc. | Polyol(allyl carbonate) composition |
US4670131A (en) † | 1986-01-13 | 1987-06-02 | Exxon Chemical Patents Inc. | Method for controlling fouling of hydrocarbon compositions containing olefinic compounds |
US4927519A (en) | 1988-04-04 | 1990-05-22 | Betz Laboratories, Inc. | Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium using multifunctional antifoulant compositions |
KR920001325B1 (ko) * | 1989-06-10 | 1992-02-10 | 삼성전자 주식회사 | 메모리 소자내의 센스 앰프 드라이버 |
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CN1064392C (zh) * | 1997-11-19 | 2001-04-11 | 中国石油化工总公司 | 石油加工过程中的防垢剂 |
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-
2002
- 2002-09-20 US US10/251,564 patent/US6926820B2/en not_active Expired - Lifetime
-
2003
- 2003-07-28 CN CNB038247402A patent/CN1304534C/zh not_active Expired - Lifetime
- 2003-07-28 ES ES03748986.1T patent/ES2297192T5/es not_active Expired - Lifetime
- 2003-07-28 DE DE60318223.2T patent/DE60318223T3/de not_active Expired - Lifetime
- 2003-07-28 WO PCT/US2003/023593 patent/WO2004026995A1/en active IP Right Grant
- 2003-07-28 JP JP2004537632A patent/JP5166676B2/ja not_active Expired - Lifetime
- 2003-07-28 AU AU2003268035A patent/AU2003268035A1/en not_active Abandoned
- 2003-07-28 AT AT03748986T patent/ATE381603T1/de not_active IP Right Cessation
- 2003-07-28 KR KR1020057004720A patent/KR101097668B1/ko active IP Right Grant
- 2003-07-28 EP EP03748986.1A patent/EP1543092B2/en not_active Expired - Lifetime
- 2003-09-10 TW TW092125048A patent/TWI282362B/zh not_active IP Right Cessation
- 2003-09-19 MY MYPI20033599A patent/MY129620A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07166152A (ja) * | 1993-12-16 | 1995-06-27 | Hakuto Co Ltd | 炭化水素類の粘度上昇抑制剤およびその方法 |
JPH09165408A (ja) * | 1995-04-14 | 1997-06-24 | Ciba Geigy Ag | 7−アリールキノンメチドを用いる不飽和モノマーの抑制 |
JPH09176215A (ja) * | 1995-04-14 | 1997-07-08 | Ciba Geigy Ag | 不飽和モノマーのための阻害剤としての7−置換キノンメチド |
Also Published As
Publication number | Publication date |
---|---|
WO2004026995A1 (en) | 2004-04-01 |
KR20050057467A (ko) | 2005-06-16 |
US20040055932A1 (en) | 2004-03-25 |
EP1543092A1 (en) | 2005-06-22 |
ATE381603T1 (de) | 2008-01-15 |
EP1543092B1 (en) | 2007-12-19 |
EP1543092B2 (en) | 2013-11-06 |
JP5166676B2 (ja) | 2013-03-21 |
ES2297192T5 (es) | 2014-01-14 |
TW200407418A (en) | 2004-05-16 |
TWI282362B (en) | 2007-06-11 |
ES2297192T3 (es) | 2008-05-01 |
AU2003268035A1 (en) | 2004-04-08 |
DE60318223T2 (de) | 2008-12-04 |
CN1694944A (zh) | 2005-11-09 |
US6926820B2 (en) | 2005-08-09 |
DE60318223T3 (de) | 2014-04-03 |
MY129620A (en) | 2007-04-30 |
DE60318223D1 (de) | 2008-01-31 |
KR101097668B1 (ko) | 2011-12-22 |
CN1304534C (zh) | 2007-03-14 |
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