JP2016222658A - オレフィン混合物からの硫黄化合物の水素支援吸着 - Google Patents
オレフィン混合物からの硫黄化合物の水素支援吸着 Download PDFInfo
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- JP2016222658A JP2016222658A JP2016104409A JP2016104409A JP2016222658A JP 2016222658 A JP2016222658 A JP 2016222658A JP 2016104409 A JP2016104409 A JP 2016104409A JP 2016104409 A JP2016104409 A JP 2016104409A JP 2016222658 A JP2016222658 A JP 2016222658A
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- hydrocarbon mixture
- sorbent
- butene
- sulfur
- hydrogen
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- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
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- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
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- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
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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
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- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
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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
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- Chemical & Material Sciences (AREA)
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- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
【解決手段】本発明が対処する問題は、混合物中に存在する硫黄化合物を実質的に完全に除去し、同時に、新たな硫黄化合物を再形成させないというものであった。同時に、そこに存在する1−ブテンは、混合物の精製において失われなかった。最終的には、使用する収着媒は、高い収着容量を有し、発癌性構成物質をまさに実質上含まず、容易に入手可能であった。この問題は、特定の組成の酸化銅、酸化亜鉛、および酸化アルミニウムをベースとする収着媒の使用により、および少量の水素の存在下で精製を行うことにより解決される。
【選択図】なし
Description
成分 分解C4[wt%] FCC C4[wt%]
イソブタン 1〜3 15〜45
n−ブタン 6〜11 5〜15
1−ブテン 14〜20 5〜20
2−ブテン 4〜8 20〜35
イソブテン 20〜28 10〜20
1,3−ブタジエン 40〜45 1未満
表0:分解C4およびFCC C4の典型的な組成物
(主成分の組成は、横列に記載の通りである。)
・酸化銅:10wt%〜60wt%(CuOとして計算);
・酸化亜鉛:10wt%〜60wt%(ZnOとして計算);
・酸化アルミニウム:10wt%〜30wt%(Al2O3として計算);
・他の物質:0wt%〜5wt%;
を有する収着媒を使用し、
水素の存在下で精製を行うことによって解決される。
・酸化銅:10wt%〜60wt%(CuOとして計算);
・酸化亜鉛:10wt%〜60wt%(ZnOとして計算);
・酸化アルミニウム:10wt%〜30wt%(Al2O3として計算);
・他の物質:0wt%〜5wt%
を有する、プロセスを提供する。
・酸化銅:30%〜45wt%(CuOとして計算);
・酸化亜鉛:30%〜50wt%(ZnOとして計算);
・酸化アルミニウム:10%〜15wt%(Al2O3として計算);
・別の金属酸化物:0%〜2wt%;
・グラファイト:0%〜3wt%;
・他の物質:0%〜1wt%
を有する触媒の使用が優先される。
i)酸化アルミニウムから構成される多孔質フレームワーク材料を用意するステップ;
ii)このフレームワーク材料を酸化銅および酸化亜鉛とブレンドするステップ
を本質的に包含する。
a)一般式R−SHのチオール類
b)一般式R−S−S−R’の二硫化物
c)一般式R−S−R’の硫化物、および
d)置換または非置換の硫黄含有ヘテロ環、例えば、特にチオフェンおよび/またはチオランなど。
仕様A:
・イソブタン15%〜45wt%、好ましくは25%〜35wt%;
・n−ブタン5%〜18wt%、好ましくは8%〜10wt%;
・1−ブテン5%〜20wt%、好ましくは12%〜14wt%;
・イソブテン12%〜25wt%、好ましくは15%〜20wt%;
・2−ブテン9%〜40wt%、好ましくは20%〜30wt%;
・1,3−ブタジエン0%〜3wt%、好ましくは0.5%〜0.8wt%;
・水0%〜1wt%、好ましくは0.1wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.2wt%未満;
・水素1wtppm未満。
仕様B:
・イソブタン0.5%〜15wt%、好ましくは1%〜7wt%;
・n−ブタン0.5%〜20wt%、好ましくは4%〜7wt%;
・1−ブテン9%〜25wt%、好ましくは10%〜20wt%;
・イソブテン10%〜35wt%、好ましくは20%〜30wt%;
・2−ブテン3%〜15wt%、好ましくは5%〜10wt%;
・1,3−ブタジエン25%〜70wt%、好ましくは40%〜50wt%;
・水0%〜1wt%、好ましくは0.5wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.2wt%未満;
・水素1wtppm未満。
仕様C:
・イソブタン0.5%〜18wt%、好ましくは1%〜7wt%;
・n−ブタン0.5%〜25wt%、好ましくは4%〜13wt%;
・1−ブテン9%〜40wt%、好ましくは10%〜35wt%;
・イソブテン10%〜55wt%、好ましくは20%〜50wt%;
・2−ブテン3%〜25wt%、好ましくは5%〜20wt%;
・1,3−ブタジエン0%〜5wt%、好ましくは0.8wt%未満;
・水0%〜1wt%、好ましくは0.5wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.2wt%未満;
・水素1wtppm未満。
仕様D:
・イソブタン0%〜20wt%、好ましくは0%〜5wt%;
・n−ブタン10%〜35wt%、好ましくは25%〜30wt%;
・1−ブテン0.2%〜45wt%、好ましくは3%〜30wt%;
・2−ブテン35%〜85wt%、好ましくは50%〜75wt%;
・水0%〜1wt%、好ましくは0.1wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.1wt%未満;
・水素1wtppm未満。
a)炭化水素混合物中に存在する1,3−ブタジエンの抽出;
b)炭化水素混合物中に存在するジオレフィンおよび/またはアセチレンの、オレフィンへの選択的な水素添加;
c)炭化水素混合物中に存在するオレフィンの、対応するオリゴマーへのオリゴマー化;
d)特に1−ブテンおよび/またはイソブタンを高純度で得るための、炭化水素混合物中に存在する1−ブテンおよび/またはイソブタンの蒸留除去;
e)イソブテンを水によりtert−ブタノールに、および/またはメタノールによりメチルtert−ブチルエーテルに転化させることによる炭化水素混合物中に存在するイソブテンの除去;
f)炭化水素混合物中に存在するブタンの、ブテンへの脱水素;
g)炭化水素混合物中に存在するブテンの、ブタジエンへの酸化的脱水素;
h)同様に存在するイソブタンを含む炭化水素混合物中に存在するn−ブテンのアルキル化;
i)無水マレイン酸を調製するための、炭化水素混合物中に存在する4個の炭素原子を有する炭化水素の酸化。
使用する収着媒は、Clariant AGから購入した、メタノール触媒として使用可能な固体である。この収着媒は、約42wt%のCuO、約44wt%のZnO、約12.5wt%のAl2O3、および約2wt%のグラファイトを含有しており、タブレット形状をしている(5×3mm)。酸化銅の比表面積は、窒素収着により測定すると、酸化銅含有量1g当たり100m2である。
使用する収着媒および実験装置は、第1実験に相当するものである。実験1と同様に、平均20.6mg/kgの硫黄を不純物として主にメタンチオールの形で供給する。均一に溶解させたH2の含有量は170wtppmである。28gの量で充填した収着媒への負荷は350g/hである、すなわち、硫黄投入は約7.2mg/hである。接触温度は80℃に設定した。収着媒の分析が示すように、硫黄は混合物から事実上定量的に除去される。約295時間目以降の操作時間から、流出口における硫黄含有量は上昇する。この急な破過は、硫黄捕縛量が約2.1g、または収着媒による硫黄収着が約7.6wt%であることに相当する。個々のC4成分の出力値は、全実験期間にわたり対応する供給値と比較して事実上変わらなかった。この実験の終了後、床を窒素でパージする。収着媒は、劣化のない状態で、十分な安定性を有して取り出すことができる。実験結果を表2に示す。
使用する収着媒および実験装置は、第1および第2実験に相当するものである。実験1と同様に、約1mg/kgの硫黄を不純物として二硫化ジエチルの形で供給する。均一に溶解させたH2の供給濃度は170wtppmである。27gの収着媒を含有する床への負荷は350g/hであり、したがって、硫黄投入は約0.35mg/hである。操作温度は80℃である。分析が示すように、硫黄は混合物から定量的に除去される。操作時間が2865時間になるまで、出力内に全く硫黄成分を検出することができなかった。その時点までに、約0.91gの硫黄が捕縛された。これは、この時までに、収着媒による硫黄収着が約3.3wt%であることに相当する。個々のC4成分の出力値は、全実験期間にわたり対応する供給値と比較して事実上変わらなかった。実験結果を表3に示す。
使用する収着媒および実験装置は、第1実験に相当するものである。しかし、実験は、水素を測定添加せずに行った。
実験から、本発明に従って、水素を測定添加すると共に適切な収着媒を組み合わせることによって行ったプロセスが、次の性質を有することが実証される:
・様々な硫黄化合物からの硫黄が、事実上完全に結合される;
・収着媒は、水素流れにおける活性化をまったく必要としない;
・収着媒は、不可逆性収着媒なので、定期的な精製および脱離流れをまったく必要としない;
・収着媒は、混合物が単一流れとして通る単一容器に、好ましくは少し高い温度(どんな場合でも下流反応器の供給に通常しばしば必要なため)で収容することができる;
・水素を測定添加しても、このプロセスは、オレフィンの副反応、例えば、オリゴマー化、異性化、および水素添加などを事実上引き起こさず、したがって、精製される混合物の価値のある構成物質の著しい損失はない。
・水素を測定添加すると、容量が増大され、したがって、これまでに知られている従来技術と比較して、収着媒の耐用年数が延長される;
・このプロセスは、下流の処理段階に何らかの影響を及ぼす濃度でどんな物質もまったく放出しない;
・硫黄の収着媒の容量が少なくとも3wt%であることから説明される、5wtppm未満という典型的な硫黄濃度での長い耐用年数から見て、収着媒を直接再生できず、その代わり、容量の消耗後、原材料の利用に送るしかできなくても、このプロセスは操作が非常に安価である;これは、銅の含有量が高いため、魅力的に見える;
・収着媒は、発癌性としても分類されず、自然発火性も示さないので、何の問題もなしに取り扱え、廃棄することができる。
Claims (15)
- 炭化水素混合物を精製するプロセスであって、3〜8個の炭素原子を有するオレフィンを含む汚染された炭化水素混合物を、固体収着媒と接触させることによって、前記炭化水素混合物から硫黄含有不純物を少なくとも部分的に取り除き、前記炭化水素混合物が、前記収着媒との接触中はすべて液体状態にあり、前記収着媒が、合計すると100wt%になる次の組成:
・酸化銅:10wt%〜60wt%(CuOとして計算);
・酸化亜鉛:10wt%〜60wt%(ZnOとして計算);
・酸化アルミニウム:10wt%〜30wt%(Al2O3として計算);
・他の物質:0wt%〜5wt%;
を有する、プロセスにおいて、
前記汚染された炭化水素混合物を、水素の存在下で、前記固体収着媒と接触させることを特徴とする、プロセス。 - 前記汚染された炭化水素混合物が、前記固体収着媒との接触直前に、前記汚染された炭化水素混合物の全質量に対して1wtppm〜10000wtppmの濃度で水素を含有し、10wtppm〜500wtppmの水素濃度が好ましいことを特徴とする、請求項1に記載のプロセス。
- 前記水素が、前記液体の汚染された炭化水素混合物中に完全に溶解されていることを特徴とする、請求項2に記載のプロセス。
- 水素添加前の前記汚染された炭化水素混合物は1wtppm未満の水素しか含有していないので、前記水素濃度を、前記接触直前に、前記汚染された炭化水素混合物に水素を添加することによって確定することを特徴とする、請求項2または3に記載のプロセス。
- 前記収着媒が、合計すると100wt%になる次の組成:
・酸化銅:30wt%〜45wt%(CuOとして計算);
・酸化亜鉛:30wt%〜50wt%(ZnOとして計算);
・酸化アルミニウム:10wt%〜15wt%(Al2O3として計算);
・別の金属酸化物:0wt%〜2wt%;
・グラファイト:0wt%〜3wt%;
・他の物質:0wt%〜1wt%
を有することを特徴とする、請求項1または請求項2から4のいずれか一項に記載のプロセス。 - 前記接触が、下記条件:
・温度10℃〜150℃、特に20℃〜130℃、より好ましくは30℃〜120℃;
・圧力0.5〜3.5MPa;
・空時収率(毎時重量空間速度−WHSV)0.5h−1〜20h−1
の下で行われることを特徴とする、請求項1または請求項2から5のいずれか一項に記載のプロセス。 - 前記汚染された炭化水素混合物が、硫黄含有不純物として、次の物質クラス:
a)一般式R−SHを有するチオール(式中、Rは、アルキル、アリール、シクロアルキル、またはアルケニル基であり得、Rは、特に、メチル、エチル、プロピル、ブチル、フェニル、シクロヘキシル、またはブテニル基である);
b)一般式R−S−S−R’を有する二硫化物(式中、RおよびR’は、同一または異なる、アルキル、アリール、シクロアルキル、またはアルケニル基であり得、RおよびR’は、特に、メチル、エチル、プロピル、ブチル、フェニル、シクロヘキシル、またはブテニル基である);
c)一般式R−S−R’を有する硫化物(式中、RおよびR’は、同一または異なる、アルキル、アリール、シクロアルキル、またはアルケニル基であり得、RおよびR’は、特に、メチル、エチル、プロピル、ブチル、フェニル、シクロヘキシル、またはブテニル基である);
d)置換または非置換の硫黄含有ヘテロ環、特にチオフェンおよび/またはチオラン
のうちの1種からの少なくとも1種の化合物を含有していることを特徴とする、請求項1または請求項2から6のいずれか一項に記載のプロセス。 - 前記汚染された炭化水素混合物中の前記硫黄含有不純物の重量割合が、硫黄として計算すると、その総重量に対して0.2wt%未満、より好ましくは100wtppm未満、最も好ましくは10wtppm未満であることを特徴とする、請求項7に記載のプロセス。
- 前記収着剤との接触によって、前記汚染された炭化水素混合物から、前記汚染された炭化水素混合物中に存在する少なくとも90wt%、好ましくは少なくとも95wt%の硫黄含有不純物を取り除くことを特徴とする、請求項8に記載のプロセス。
- 前記汚染された炭化水素混合物が、より高度に汚染された原材料混合物を予備精製して前記汚染された炭化水素混合物を得る予備精製段階から得られることを特徴とする、請求項8または9に記載のプロセス。
- 前記収着媒が不可逆に使用されることを特徴とする、請求項10に記載のプロセス。
- 前記汚染された炭化水素混合物が、次の仕様A、B、C、およびD:
仕様A:
・イソブタン15%〜45wt%、好ましくは25%〜35wt%;
・n−ブタン5%〜18wt%、好ましくは8%〜10wt%;
・1−ブテン5%〜20wt%、好ましくは12%〜14wt%;
・イソブテン12%〜25wt%、好ましくは15%〜20wt%;
・2−ブテン9%〜40wt%、好ましくは20%〜30wt%;
・1,3−ブタジエン0%〜3wt%、好ましくは0.5%〜0.8wt%;
・水0%〜1wt%、好ましくは0.1wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.2wt%未満;
・水素1wtppm未満、
仕様B:
・イソブタン0.5%〜15wt%、好ましくは1%〜7wt%;
・n−ブタン0.5%〜20wt%、好ましくは4%〜7wt%;
・1−ブテン9%〜25wt%、好ましくは10%〜20wt%;
・イソブテン10%〜35wt%、好ましくは20%〜30wt%;
・2−ブテン3%〜15wt%、好ましくは5%〜10wt%;
・1,3−ブタジエン25%〜70wt%、好ましくは40%〜50wt%;
・水0%〜1wt%、好ましくは0.5wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.2wt%未満;
・水素1wtppm未満、
仕様C:
・イソブタン0.5%〜18wt%、好ましくは1%〜7wt%;
・n−ブタン0.5%〜25wt%、好ましくは4%〜13wt%;
・1−ブテン9%〜40wt%、好ましくは10%〜35wt%;
・イソブテン10%〜55wt%、好ましくは20%〜50wt%;
・2−ブテン3%〜25wt%、好ましくは5%〜20wt%;
・1,3−ブタジエン0%〜5wt%、好ましくは0.8wt%未満;
・水0%〜1wt%、好ましくは0.5wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.2wt%未満;
・水素1wtppm未満、
仕様D:
・イソブタン0%〜20wt%、好ましくは0%〜5wt%;
・n−ブタン10%〜35wt%、好ましくは25%〜30wt%;
・1−ブテン0.2%〜45wt%、好ましくは3%〜30wt%;
・2−ブテン35%〜85wt%、好ましくは50%〜75wt%;
・水0%〜1wt%、好ましくは0.1wt%未満;
・硫黄含有不純物0.5wt%未満、好ましくは0.1wt%未満;
・水素1wtppm未満
のうちの1つを満足するものであり、これらの各々が、合計すると100wt%になり、規定の前記重量割合が各々、前記汚染された炭化水素混合物の総重量に基づいていることを特徴とする、請求項4または請求項5から11のいずれか一項に記載のプロセス。 - 前記収着媒との接触が、前記汚染された炭化水素混合物中に存在する1−ブテンの5%未満の転化をもたらすことを特徴とする、請求項12に記載のプロセス。
- 前記汚染された炭化水素混合物が、1−ブテンを含み、前記収着媒との接触によって、前記汚染された炭化水素混合物に含まれる1−ブテンの5%未満が転化されることを特徴とする、請求項1から11の少なくとも一項に記載のプロセス。
- 不純物が少なくとも部分的に取り除かれた前記炭化水素混合物に、下に列挙する後処理ステップ:
a)前記炭化水素混合物中に存在する1,3−ブタジエンの抽出;
b)前記炭化水素混合物中に存在するジオレフィンおよび/またはアセチレンのオレフィンへの選択的な水素添加;
c)前記炭化水素混合物中に存在するオレフィンの対応するオリゴマーへのオリゴマー化;
d)特に1−ブテンおよび/またはイソブタンを高純度で得るための、前記炭化水素混合物中に存在する1−ブテンおよび/またはイソブタンの蒸留除去;
e)イソブテンを水によりtert−ブタノールにおよび/またはメタノールによりメチルtert−ブチルエーテルに転化させることによる前記炭化水素混合物中に存在するイソブテンの除去;
f)前記炭化水素混合物中に存在するブタンのブテンへの脱水素;
g)前記炭化水素混合物中に存在するブテンのブタジエンへの酸化的脱水素;
h)同様に存在するイソブタンを含む前記炭化水素混合物中に存在するn−ブテンのアルキル化;
i)無水マレイン酸を調製するための、前記炭化水素混合物中に存在する4個の炭素原子を有する炭化水素の酸化
の少なくとも1つを施すことを特徴とする、請求項1または請求項2から14のいずれか一項に記載のプロセス。
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CN111960913A (zh) * | 2019-05-14 | 2020-11-20 | 赢创运营有限公司 | 用于纯化包含残余丁烯的烃料流的方法 |
CN112755591B (zh) * | 2019-10-21 | 2023-04-07 | 中国石油化工股份有限公司 | 脱除有机溶剂中碱性含氮物质的方法和芳烃烷基化反应的方法及芳烃烷基化反应的装置 |
KR20210078585A (ko) | 2019-12-18 | 2021-06-29 | 사빅 에스케이 넥슬렌 컴퍼니 피티이 엘티디 | 알파올레핀의 정제방법 및 이를 위한 알파올레핀 정제용 조성물 |
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