JP5271704B2 - 窒素含有率が極めて低い石油類の製造方法 - Google Patents
窒素含有率が極めて低い石油類の製造方法 Download PDFInfo
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- JP5271704B2 JP5271704B2 JP2008519402A JP2008519402A JP5271704B2 JP 5271704 B2 JP5271704 B2 JP 5271704B2 JP 2008519402 A JP2008519402 A JP 2008519402A JP 2008519402 A JP2008519402 A JP 2008519402A JP 5271704 B2 JP5271704 B2 JP 5271704B2
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- nitrogen
- water
- light petroleum
- extraction
- aromatic
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- 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
- C10G53/10—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one acid-treatment 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
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- C10G17/02—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge with acids or acid-containing liquids, e.g. acid sludge
- C10G17/04—Liquid-liquid treatment forming two immiscible phases
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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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
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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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
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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
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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
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- 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
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- C10G2300/10—Feedstock materials
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/104—Light gasoline having a boiling range of about 20 - 100 °C
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Description
(a)N-ホルミル-モルホリン、N-メチル-2-ピロリドン、及びそれらの混合物を含む窒素含有抽出溶剤を用いた液−液抽出又は抽出蒸留によって製造した軽質石油の供給原料であって、沸点が140℃未満の抽出芳香族を含み、この沸点範囲内の沸点を有する該石油の供給原料中の窒素含有化合物が水溶性であることを特徴とする、窒素含有化合物を2ppm以下含む軽質石油の供給原料を準備する工程と、
(b)抽出ゾーン中の抽出条件で、前記軽質石油の供給原料を水性抽出溶剤と接触させる工程と、
(c)工程(b)の生成物を(i)分離された軽質石油を含むラフィネート製品の流れと(ii)水性抽出相とに分離する工程と、
(d)前記ラフィネート製品の流れから水を除去して、窒素を100ppb以下含む窒素が除去され脱水された芳香族を生産する工程と
を含む。
(a)沸点が140℃未満であって、水溶性の窒素含有化合物を含む軽質石油の供給原料を準備する工程と、
(b)窒素含有化合物を含む軽質石油の供給原料を水抽出溶剤としてのpHが7未満の水と接触させる工程と、
(c)前記水抽出溶剤から前記軽質石油を分離し、窒素含有化合物を100ppb以下含む軽質石油を生産する工程と、
(d)分離された軽質石油から残留水を除去して、脱水された軽質石油を生産する工程と、
(e)脱水軽質石油を、炭化水素の転化条件で酸性触媒と接触させる工程と
を含む。
この例では、図1の蒸留カラム20中に供給するHDS廃液18の代表例である芳香族炭化水素組成物を準備した。該組成物は、供給原料10がHDSユニット16中に投入される前に供給原料10に添加される中和添加剤として用いられる類の高分子量窒素化合物を少量含んでいる。ほぼ98重量%が芳香族からなる組成物は、表1に示す以下の成分を含んでいた。
例1に記載したのと同じ抽出手順を用いて、ベンゼン約97.5重量%、C6からC7の非芳香族2.5重量%及び痕跡量(2.9 ppm)の窒素化合物を含むベンゼン組成物を、新品の脱イオン水で3回抽出した。各抽出における水対ベンゼンの組成重量比は、1:1とした。各抽出段階後の炭化水素(ベンゼン)相の痕跡窒素を分析し、その結果を表2に示す。
水の量を少なく、即ち、水対ベンゼンの組成比を0.5及び0.1にする以外は、例2の窒素抽出手順を繰り返した。各抽出段階後の炭化水素(ベンゼン)相の窒素を分析し、その結果を表3に示す。
例2及び3で用いたベンゼン組成物をガスクロマトグラフィー−質量分析計で分析し、存在する窒素化合物の分子構造を同定した。ベンゼン組成物中の窒素含有化合物が本質的にモルホリンであることが分かり、該モルホリンは、芳香族抽出システム、例えば、図1のシステム26で用いたNFM溶媒からの分解フラグメントである。モルホリンは水溶性であるので、この実験で、図3に示した液体抽出カラムLEC66を用いて、精製した芳香族の供給流れ60からモルホリンを抽出できることが確かめられた。モルホリンの沸点(128.3℃)は、ベンゼンの沸点よりも非常に高く、モルホリンは、水又はベンゼンと共沸混合物を形成しないので、水性ラフィネートの流れ68中にモルホリンが存在する場合、該残留モルホリンは、共沸蒸留カラム78の底部から除去できる。
この例で、酸性化した水が芳香族から窒素を抽出することにおいて水よりも効果的であることを示す。例1で記載したのと同じ抽出手順を用いて、窒素を2.9 ppm含むベンゼン組成物を、室温において多段抽出によって、脱イオン水及び酸性化した脱イオン水で抽出した。各例において、水対ベンゼンの重量比は、0.2とした。脱イオン水に酢酸を加えて、pHを7.0から5.11に低下させて、酸性化水を調製した。各抽出後のベンゼン組成物相の痕跡窒素を分析し、表4に比較抽出の結果を示す。
Claims (32)
- 窒素含有化合物を100ppb以下含む軽質石油の製造方法であって、
(a)窒素含有化合物及びC 6 −C 8 の芳香族を含む軽質石油の供給原料を水素化脱硫して、硫黄を除去し、且つ、軽質石油の供給原料の廃液を製造し、その後、該廃液を蒸留して、(i)重質炭化水素類の流れと(ii)C 6 −C 8 留分を含む軽質炭化水素類の流れとを生産する工程と、
(b)前記軽質炭化水素類の流れを、N-ホルミル-モルホリン又はN-メチル-2-ピロリドン、及びそれらの混合物を含む窒素含有抽出溶剤を用いて液−液抽出又は抽出蒸留して、(i)非芳香族の流れと(ii)窒素含有化合物を2ppm以下含み、沸点が140℃未満の芳香族を含む抽出芳香族の流れとを生産する工程であって、この沸点範囲内の沸点を有する該抽出芳香族の流れ中の窒素含有化合物が水溶性である工程と、
(c)連続的に前記抽出芳香族の流れを酸性の水性抽出溶剤と接触させる多段容器である液−液抽出器中の抽出条件で、前記抽出芳香族の流れを酸性の水性抽出溶剤と接触させる工程と、
(d)工程(c)の生成物を(i)分離された軽質石油を含むラフィネート製品の流れと(ii)水性抽出相とに分離する工程と、
(e)(i)共沸蒸留、(ii)クレー若しくは無機塩での吸着、又は(iii)吸着蒸留によって水の除去を達成することにより、前記ラフィネート製品の流れから水を除去して、窒素を100ppb以下含む窒素が除去され脱水された芳香族を生産する工程と
を含む、窒素含有化合物を100ppb以下含む軽質石油の製造方法。 - 前記工程(e)が、共沸蒸留カラム中で起こる共沸蒸留により、分離された軽質石油から水を除去することを含み、ここで、ベンゼン及び水は該カラムの頂部から除去される最低沸点共沸混合物を形成し、窒素が除去され脱水された芳香族は該蒸留カラムの底部から回収されることを特徴とする請求項1に記載の方法。
- 前記窒素が除去された芳香族は、窒素を30 ppb未満含むことを特徴とする請求項2に記載の方法。
- 前記窒素が除去され脱水された芳香族を、前記蒸留カラムの頂部近傍の蒸留カラムの側流からも回収することを特徴とする請求項3に記載の方法。
- 前記多段容器が、(i)トレーが複数設置されたカラム、(ii)充填物が設置されたカラム、(iii)回転ディスクが複数設置されたカラム、(iv)パルスカラム、(v)多段混合機及び沈降槽、並びにそれらの組み合わせからなる群から選択される装置であることを特徴とする請求項1に記載の方法。
- 前記多段容器が、複数のトレー又は充填物が設置された向流多段抽出カラムを具えることを特徴とする請求項1に記載の方法。
- 前記多段容器が、軽質石油の供給原料が入る第1下方端部と、水性抽出溶剤が入る第2上方端部とを有することを特徴とする請求項6に記載の方法。
- 更に、第1下方端部と第2上方端部との間の位置において、前記多段容器中にpHが7未満の酸性化水を加える工程を含むことを特徴とする請求項6に記載の方法。
- 前記抽出条件は、水対芳香族の供給重量比(W/F)の範囲が0.01から100であることを含むことを特徴とする請求項1に記載の方法。
- 前記抽出条件は、水対芳香族の供給重量比(W/F)の範囲が0.05から50であることを含むことを特徴とする請求項1に記載の方法。
- 前記抽出条件は、水対芳香族の供給重量比(W/F)の範囲が0.1から10であることを含むことを特徴とする請求項1に記載の方法。
- 前記抽出条件は、温度が0から100℃の範囲であること及び圧力が0から100 psigの範囲であることを含むことを特徴とする請求項1に記載の方法。
- 前記抽出条件は、温度が25から50℃の範囲であること及び圧力が0から20 psigの範囲であることを含むことを特徴とする請求項1に記載の方法。
- 水性抽出相の第1部分を前記液−液抽出カラムの下方区域にリサイクルし、水性抽出相の第2部分を排出することを特徴とする請求項3に記載の方法。
- 前記水性抽出相の第1部分 対 前記水性抽出相の第2部分の重量比が、0超から500対1の範囲であることを特徴とする請求項14に記載の方法。
- 前記水性抽出相の第1部分 対 前記水性抽出相の第2部分の重量比が、1対1から50対1の範囲であることを特徴とする請求項14に記載の方法。
- 前記軽質石油の供給原料、前記軽質炭化水素類の流れ、及び/又は前記抽出芳香族の流れに酸を添加して、それらにおける窒素含有化合物のいくつかを少なくとも部分的に中和することを特徴とする請求項1に記載の方法。
- 前記酸が、酢酸、ギ酸、又はその両方を含むことを特徴とする請求項17に記載の方法。
- 前記酸が、酢酸を含むことを特徴とする請求項17に記載の方法。
- 工程(e)が、窒素含有化合物を1ppm未満含有する軽質石油を生成させることを特徴とする請求項1に記載の方法。
- 酸性触媒が触媒作用を及ぼす反応において炭化水素類を転換する方法であって、
(a)沸点が140℃未満であって、水溶性の窒素含有化合物を2ppm以下含む軽質石油の供給原料を準備する工程と、
(b)前記窒素含有化合物を含む軽質石油の供給原料を、酸性の水性抽出溶剤と接触させる工程と、
(c)前記水性抽出溶剤から前記軽質石油を分離して、窒素含有化合物を100ppb以下含む軽質石油を生産する工程と、
(d)共沸蒸留、クレー若しくは無機塩での吸着、又は吸着蒸留によって残留水の除去を達成することにより、分離された軽質石油から残留水を除去して、脱水された軽質石油の流れと水を含む流れとを生産する工程と、
(e)脱水軽質石油を、炭化水素の転化条件で酸性触媒と接触させる工程と
を含む、炭化水素類の転換方法。 - 工程(b)の前、間、又は前と間の両方において前記軽質石油の供給原料に酸を添加して、軽質石油の供給原料中の窒素含有化合物のいくつかを少なくとも部分的に中和することを特徴とする請求項21に記載の方法。
- 前記酸が、酢酸、ギ酸、又はその両方を含むことを特徴とする請求項22に記載の方法。
- 前記酸が、酢酸を含むことを特徴とする請求項23に記載の方法。
- 前記酸性触媒が、ゼオライト、及び塩基性窒素毒に敏感な他の固体触媒を含む群から選択されることを特徴とする請求項21に記載の方法。
- 前記軽質石油の供給原料が、分解ガソリン、改質ガソリン、ナフサ、又は石炭由来のコーカー油から抽出された芳香族製品であることを特徴とする請求項21に記載の方法。
- 前記軽質石油の供給原料を、窒素含有抽出溶剤を用いた液−液抽出又は抽出蒸留によって製造することを特徴とする請求項26に記載の方法。
- 前記抽出溶剤が、N-ホルミル-モルホリン(NFM)、N-メチル-2-ピロリドン(NMP)、及びそれらの混合物からなる群から選択されることを特徴とする請求項27に記載の方法。
- 前記軽質石油の供給原料が、前記軽質石油の供給原料を製造する流れ中に存在する酸性イオンを中和する腐食防止剤である中和窒素含有添加剤から発生した軽質窒素含有化合物を含むことを特徴とする請求項28に記載の方法。
- 前記軽質石油の供給原料が、NFM、NMP、又はそれらの混合物から発生した軽質窒素含有化合物を含むことを特徴とする請求項28に記載の方法。
- 前記軽質窒素含有化合物は、水に不溶でもよい中和窒素含有添加剤の比較的重質な部分を除去するための蒸留後の沸点が135℃以下であることを特徴とする請求項21に記載の方法。
- 前記添加剤が、ジエチルアミン、n-ブチルアミン、ジイソプロピルアミン、ピロリジン、3-ピロリン、n-アミルアミン、n-ジプロピルアミン、スペルミジン、メチルヘキサンアミン、シクロヘキシルアミン、及びそれらの混合物からなる群から選択されることを特徴とする請求項31に記載の方法。
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JP2009500472A (ja) | 2009-01-08 |
CN101243161A (zh) | 2008-08-13 |
US7727383B2 (en) | 2010-06-01 |
EP1907512A2 (en) | 2008-04-09 |
WO2007005298A3 (en) | 2007-02-22 |
US20070000809A1 (en) | 2007-01-04 |
US8425764B2 (en) | 2013-04-23 |
CN101243161B (zh) | 2012-07-04 |
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