JP4218751B2 - 硫黄含量低下のための膜分離 - Google Patents
硫黄含量低下のための膜分離 Download PDFInfo
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- 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
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/08—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one sorption step
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- 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
- C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
- C10G31/11—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by dialysis
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- 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
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
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- 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
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
Description
”炭化水素”という用語は、本明細書において炭化水素性が優勢である有機化合物を意味するのに用いられる。この定義の範囲において、炭化水素化合物は少なくとも1個の非炭化水素基(たとえば硫黄または酸素)を含んでもよいものとする。ただしその非炭化水素基は、その有機化合物の優勢な炭化水素性を変更せず、および/または本発明の範囲内の膜と反応してその化学的性質を変更しない。
本発明の膜分離法を用いて得られる硫黄の少ない残留画分は、一般に100ppm未満、好ましくは50ppm未満、最も好ましくは30ppm未満の硫黄を含有する。好ましい態様において、回収した残留物流の硫黄含量は供給物の初期硫黄含量の30重量%未満、好ましくは20重量%未満、最も好ましくは10重量%未満である。
パーベーパレーション法は、透過物を膜表面から蒸発その他の形で引き離すために、透過側の真空または掃引ガスに依存する。供給物は液状および/または気体状である。気体状の場合、本方法は蒸気透過と言える。パーベーパレーションは約25〜200℃およびそれ以上の温度で実施でき、最高温度は膜が物理的損傷を受ける温度である。資本経費を減らすために、パーベーパレーション法を一段操作として操作することが好ましい。
さらに、本明細書または特許請求の範囲に示した数値範囲、たとえば特定の一群の特性、測定の単位、条件、物理的状態または%は、実際に参考のためなどとして特に示したものである。示された範囲内のあらゆる組の数値を含めたいかなる数値もその範囲に含まれる。
膜クーポンをパーベーパレーション試験のために試料ホルダーに取り付ける。製油所から得たナフサの供給物溶液または実験室で混合したモデル溶液を膜表面へ送り込む。この装置は、供給物溶液を加熱でき、かつ約5バールまで加圧できるように設計されている。真空ポンプをコールドトラップに接続し、次いで膜の透過側に接続する。ポンプは透過側に20mmHg未満の真空を発生する。透過物はコールドトラップ内で凝縮し、次いでガスクロマトグラフィーにより分析される。これらの実験は、1%未満の供給物が透過物として採集されるように、低段階カットで実施された。透過物の硫黄含量を供給物の硫黄含量で割ったものに基づいて富化係数(EF)を計算する。
ポリシロキサン分離層をもつ市販のパーベーパレーション膜(PERVAP(登録商標)1060)(Sulzer ChemTech、スイス)を、5成分モデル供給物について試験した(表1)。この膜は、チオフェンについて実質的な透過速度および2.35の富化係数を示す。ナフサ供給物の温度が高い方では、メルカプタン類(アルキルS)は2.37の富化係数を有していた。
USP5,264,166の方法に従ってポリイミド膜を作成し、パーベーパレーションについて試験した。26%のMatrimid 5218ポリイミド、5%のマレイン酸、20%のアセトンおよび49%のN−メチルピロリドンを含有するドープ溶液を、4ft/分で、ブレードギャップを7ミルに設定してポリエステル不織布上に流延した。約30秒後、被覆した不織布を22℃の水中で固定して膜構造体を形成した。膜を水で洗浄して残留溶剤を除去した。次いで2−プロパノンに浸漬し、続いて潤滑油/2−プロパノン/トルエン等量混合物の浴に浸漬することにより、溶剤交換した。膜を風乾して、コンディショニング剤を充填した非対称膜を得た。
米国特許出願09/126,261の方法に従って他のポリイミド膜を作成し、パーベーパレーションについて試験した。20%のLenzing P84、69%のp−ジオキサンおよび11%のジメチルホルムアミドを含有するドープ溶液を、4ft/分で、ブレードギャップを7ミルに設定してポリエステル不織布上に流延した。約3秒後、被覆した不織布を20℃の水中で固定して膜構造体を形成した。膜を水で洗浄して残留溶剤を除去した。次いで2−ブタノンに浸漬し、続いて潤滑油/2−ブタノン/トルエン等量混合物の浴に浸漬することにより、溶剤交換した。次いで膜を風乾して、コンディショニング剤を充填した非対称膜を得た。
実施例4
Matrimid 5218を微孔質支持体に被覆することによりポリイミド複合材料膜を作成した。ジメチルホルムアミド中20%Matrimid溶液を2000rpmで10秒間、次いで4000rpmで10秒間、孔径0.45ミクロンのナイロンディスク(Millipore Corporation,マサチュセッツ州ベッドフォード;カタログ#HNWP04700)上にスピンコーティングした。次いで膜を風乾した。膜をそのままナフサ供給物について試験したところ(表5)、チオフェンについて2.68の富化係数を示した。メルカプタン(アルキルS)は1.41の富化係数を有していた。残留物回収率99%で、残留物中のオレフィン回収率は99.1%であった。
USP4,921,611の方法に従って多孔質支持体を被覆することによりポリウレア/ウレタン(PUU)複合材料膜を作成した。p−ジオキサン9.09g中における0.7866gのトルエンジシソシアナート末端基付きポリエチレンアジペート(Aldrich Chemical Company,ワイオミング州ミルウォーキー;カタログ#43,351−9)の溶液に、p−ジオキサン3.00gに溶解した0.1183gの4−4’−メチレンジアニリン(Aldrich,#13,245−4)を添加した。溶液がゲル化し始めた時点で、ブレードギャップを3.6ミルに設定して孔径0.2ミクロンの微孔質ポリテトラフルオロエチレン(PTFE)膜(W.L.Gore,メリーランド州エルクトン)上に被覆した。溶剤が蒸発して連続フィルムが得られた。次いで複合材料膜をオーブン内で100℃に1時間加熱した。最終複合材料膜構造体は、走査電子顕微鏡検査により測定して厚さ3ミクロンのPUU被覆を有していた。この膜をそのままナフサについて試験した(表6)。膜は、チオフェンについて7.53、メルカプタンについて3.15の富化係数を示した。
実施例5と同様にしてポリウレア/ウレタン(PUU)複合材料膜を作成した。ただしp−ジオキサンの代わりにN,N−ジメチルホルムアミド(DMF)を用いた。3.29gのDMF中における0.4846gのトルエンジシソシアナート末端基付きポリエチレンアジペート(Aldrich Chemical Company,ワイオミング州ミルウォーキー;カタログ#43,351−9)の溶液に、0.66gのDMFに溶解した0.0749gの4−4’−メチレンジアニリン(Aldrich,#13,245−4)を添加した。溶液がゲル化し始めた時点で、ブレードギャップを3.6ミルに設定して孔径0.2ミクロンの微孔質ポリテトラフルオロエチレン(PTFE)膜(W.L.Gore,メリーランド州エルクトン)上に被覆した。溶剤が蒸発して連続フィルムが得られた。次いで複合材料膜をオーブン内で94℃に2時間加熱した。最終複合材料膜構造体は、6.1g/m2のPUU被覆重量を有していた。この膜をそのままナフサについて試験した(表7)。膜は、チオフェンについて9.58、メルカプタン(アルキルS)について4.15の富化係数を示す。残留物回収率99%で、残留物中のオレフィン回収率は99.2%である。
沸騰範囲50〜98℃のFCC軽質接触分解ナフサは300ppmの硫黄化合物を含有する。これを98℃で操作される膜パーベーパレーションシステムに100m3/時の速度で送入する。
Claims (30)
- ナフサ炭化水素供給物流中のオレフィン化合物の収率を実質的に維持しつつ該ナフサ炭化水素供給物流の硫黄含量を低下させる方法であって、
i)150〜3000ppmの硫黄含量を有するナフサ供給物をパーベーパレーション条件下で膜分離帯域と接触させて、硫黄に富む透過画分と硫黄の少ない残留画分とを分離し、
ここで分離帯域はポリイミド膜又はポリシロキサン膜を収容し、ナフサ炭化水素供給物は硫黄を含有する芳香族炭化水素、硫黄を含有する非芳香族炭化水素、およびオレフィン化合物を含み、そして硫黄に富む透過画分はナフサ炭化水素供給物と比較して、硫黄を含有する芳香族炭化水素および硫黄を含有する非芳香族炭化水素に富み;
ii)硫黄の少ない残留画分を生成物流として回収し;
iii)硫黄に富む透過画分を膜以外のプロセスへ供給して硫黄含量を低下させ、硫黄含量を低下させた透過生成物流を生成し;そして
iv)硫黄含量を低下させた透過生成物流を回収する
ことを含む方法。 - 硫黄の少ない残留画分の硫黄含量が100ppm未満である、請求項1に記載の方法。
- 硫黄の少ない残留画分の硫黄含量が50ppm未満である、請求項2に記載の方法。
- 硫黄の少ない残留画分の硫黄含量が30ppm未満である、請求項3に記載の方法。
- ナフサ供給物流が分解ナフサである、請求項1に記載の方法。
- 分解ナフサがFCCナフサである、請求項5に記載の方法。
- FCCナフサが、50〜105℃の沸騰範囲を有するFCC軽質接触分解ナフサである、請求項6に記載の方法。
- ナフサ供給物がコーカーナフサ、直留ナフサ、軽質ナフサ、中間ナフサ及びこれらの混合物からなる群から選択される、請求項1に記載の方法。
- 硫黄の少ない残留画分が全供給物の少なくとも50重量%である、請求項1に記載の方法。
- 残留生成物流および透過生成物流中のオレフィン化合物の全量が、ナフサ供給物中に存在していたオレフィン化合物の少なくとも50重量%である、請求項1に記載の方法。
- 残留生成物流および透過生成物流中のオレフィン化合物の全量が、ナフサ供給物中に存在していたオレフィン化合物の50〜90重量%である、請求項1に記載の方法。
- 工程 iii) の膜以外のプロセスが水素化精製プロセスである、請求項1に記載の方法。
- 工程 iii) の膜以外のプロセスが吸着プロセスである、請求項1に記載の方法。
- 工程 iii) の膜以外のプロセスが接触蒸留プロセスである、請求項1に記載の方法。
- ナフサ炭化水素供給物流中のオレフィン化合物の収率を実質的に維持しつつ該ナフサ炭化水素供給物流の硫黄含量を低下させる方法であって、
i)150〜3000ppmの硫黄含量を有するナフサ供給物をパーベーパレーション条件下で膜分離帯域と接触させて、硫黄に富む透過画分と硫黄の少ない残留画分とを分離し、
ここで膜分離帯域はポリウレア−ウレタン膜を収容し、ナフサ炭化水素供給物は、軽質ナフサ、中間ナフサ、コーカーナフサ、直留ナフサ及びこれらの混合物からなる群から選択され、そしてナフサ炭化水素供給物は、硫黄を含有する芳香族炭化水素、硫黄を含有する非芳香族炭化水素、およびオレフィン化合物を含み、硫黄に富む透過画分はナフサ炭化 水素供給物と比較して、硫黄を含有する芳香族炭化水素および硫黄を含有する非芳香族炭化水素に富み;
ii)硫黄の少ない残留画分を生成物流として回収し;
iii)硫黄に富む透過画分を膜以外のプロセスへ供給して硫黄含量を低下させ、硫黄含量を低下させた透過生成物流を生成し;そして
iv)硫黄含量を低下させた透過生成物流を回収する
ことを含む方法。 - 硫黄の少ない残留画分の硫黄含量が100ppm未満である、請求項15に記載の方法。
- 硫黄の少ない残留画分の硫黄含量が30ppm未満である、請求項16に記載の方法。
- ナフサ供給物流が分解ナフサである、請求項16に記載の方法。
- 分解ナフサがFCCナフサである、請求項18に記載の方法。
- FCCナフサが、50〜105℃の沸騰範囲を有するFCC軽質接触分解ナフサである、請求項19に記載の方法。
- 硫黄の少ない残留画分が全供給物の少なくとも50重量%である、請求項15に記載の方法。
- 残留生成物流および透過生成物流中のオレフィン化合物の全量が、ナフサ供給物中に存在していたオレフィン化合物の少なくとも50重量%である、請求項15に記載の方法。
- 残留生成物流および透過生成物流中のオレフィン化合物の全量が、ナフサ供給物中に存在していたオレフィン化合物の50〜90重量%である、請求項22に記載の方法。
- 工程 iii) の膜以外のプロセスが水素化精製プロセスである、請求項15に記載の方法。
- 工程 iii) の膜以外のプロセスが吸着プロセスである、請求項15に記載の方法。
- 工程 iii) の膜以外のプロセスが接触蒸留プロセスである、請求項15に記載の方法。
- 硫黄の少ない残留画分が供給物中のオレフィンの50重量%より多量のオレフィンを含む、請求項1に記載の方法。
- 硫黄の少ない残留画分が供給物中のオレフィンの50重量%より多量のオレフィンを含む、請求項15に記載の方法。
- 工程i)において、ナフサ供給物側が5バール以下の圧力であり、透過側が20mmHg以下の真空から大気圧までの圧力であり、そしてナフサ供給物が24℃〜200℃の温度に加熱される、請求項1又は15に記載の方法。
- 工程i)において、ナフサ供給物側が5バール以下の圧力であり、透過側が20mmHg以下の真空圧力であり、そしてナフサ供給物が24℃〜78℃の温度に加熱される、請求項1又は15に記載の方法。
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US09/784,898 US6896796B2 (en) | 2001-02-16 | 2001-02-16 | Membrane separation for sulfur reduction |
PCT/US2002/005347 WO2002068568A2 (en) | 2001-02-16 | 2002-02-13 | Membrane separation for sulfur reduction |
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US20020139719A1 (en) * | 2000-12-28 | 2002-10-03 | Minhas Bhupender S. | Removal of thiophenic sulfur from gasoline by membrane separation process |
US6649061B2 (en) | 2000-12-28 | 2003-11-18 | Exxonmobil Research And Engineering Company | Membrane process for separating sulfur compounds from FCC light naphtha |
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- 2002-02-13 CA CA002438700A patent/CA2438700A1/en not_active Abandoned
- 2002-02-13 AU AU2002255584A patent/AU2002255584B2/en not_active Ceased
- 2002-02-13 EP EP02724988A patent/EP1373439B1/en not_active Expired - Lifetime
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- 2002-02-13 MX MXPA03007011A patent/MXPA03007011A/es active IP Right Grant
- 2002-02-13 CN CNA2007101544578A patent/CN101186841A/zh active Pending
- 2002-02-13 BR BR0207174-6A patent/BR0207174A/pt not_active Application Discontinuation
- 2002-02-13 JP JP2002568665A patent/JP4218751B2/ja not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
US20030173255A1 (en) | 2003-09-18 |
KR100843791B1 (ko) | 2008-07-03 |
DE60221370T2 (de) | 2008-04-17 |
AU2002255584B2 (en) | 2007-06-28 |
ES2290288T3 (es) | 2008-02-16 |
CN1743424A (zh) | 2006-03-08 |
DE60221370D1 (de) | 2007-09-06 |
US20040211705A1 (en) | 2004-10-28 |
US6896796B2 (en) | 2005-05-24 |
CA2438700A1 (en) | 2002-09-06 |
US7018527B2 (en) | 2006-03-28 |
KR20030090641A (ko) | 2003-11-28 |
WO2002068568A3 (en) | 2003-04-10 |
EP1373439A2 (en) | 2004-01-02 |
ATE368094T1 (de) | 2007-08-15 |
CN1320080C (zh) | 2007-06-06 |
US7041212B2 (en) | 2006-05-09 |
CN1513049A (zh) | 2004-07-14 |
EP1373439B1 (en) | 2007-07-25 |
US20020153284A1 (en) | 2002-10-24 |
CN100564488C (zh) | 2009-12-02 |
WO2002068568A2 (en) | 2002-09-06 |
US20040211706A1 (en) | 2004-10-28 |
BR0207174A (pt) | 2004-06-15 |
US7048846B2 (en) | 2006-05-23 |
JP2004528417A (ja) | 2004-09-16 |
CN101186841A (zh) | 2008-05-28 |
MXPA03007011A (es) | 2003-11-18 |
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