JP5890909B2 - デュアル触媒系を用いた芳香族異性体化 - Google Patents
デュアル触媒系を用いた芳香族異性体化 Download PDFInfo
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- JP5890909B2 JP5890909B2 JP2014541092A JP2014541092A JP5890909B2 JP 5890909 B2 JP5890909 B2 JP 5890909B2 JP 2014541092 A JP2014541092 A JP 2014541092A JP 2014541092 A JP2014541092 A JP 2014541092A JP 5890909 B2 JP5890909 B2 JP 5890909B2
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- catalysts
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- isomerization
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- 238000000034 method Methods 0.000 claims description 38
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- CTDPVEAZJVZJKG-UHFFFAOYSA-K trichloroplatinum Chemical compound Cl[Pt](Cl)Cl CTDPVEAZJVZJKG-UHFFFAOYSA-K 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Description
本出願は、2011年11月14日に出願された米国特許仮出願第61/559,226号の優先権の利益を主張するものである。
本発明は、接触炭化水素変換に関し、より詳細には、芳香族異性体化における改善されたモレキュラーシーブ触媒系の使用に関する。
バインダーは、表面積が25から500m2/gであり、組成が均一であり、炭化水素変換プロセスで用いられる条件に対して比較的耐熱性を有する、多孔性吸着性支持体であるべきである。「組成が均一」の用語は、支持体が層形成しておらず、その組成に固有の種に濃度勾配がなく、組成が完全に均質であることを意味している。従って、支持体が2つ以上の耐熱性物質の混合物である場合、これらの物質の相対量は、支持体全体にわたって一定であり、均一である。本発明の範囲内には、炭化水素変換触媒に従来から用いられてきたキャリア物質を含むことを意図しており:(1)アルミナ、チタニア、ジルコニア、クロミア、酸化亜鉛、マグネシア、トリア、ボリア、シリカ−アルミナ、シリカ−マグネシア、クロミア−アルミナ、アルミナ−ボリア、シリカ−ジルコニアなどの耐熱性無機酸化物;(2)セラミック、磁器、ボーキサイト;(3)合成によって作製されたもの、および天然のものを含み、酸処理されていても、またはされていなくてもよい、シリカまたはシリカゲル、炭化ケイ素、クレイ、およびシリケート、例えば、アタパルジャイトクレイ、珪藻土、フラー土、カオリン、キーゼルグールなど;(4)FAU、MEL、MFI、MOR、MTW(ゼオライト命名法に関するIUPAC委員会(IUPAC Commission on Zeolite Nomenclature))などの、天然であるかまたは合成によって作製され、水素型または金属カチオンで交換された形態である結晶性ゼオライト系アルミノシリケート、(5)式MO−Al2O3を有し、式中、Mは価数2を持つ金属であるMgAl2O4、FeAl2O4、ZnAl2O4、CaAl2O4、およびその他の類似の化合物などのスピネル;ならびに(6)これらの群の1つ以上からの物質の組み合わせ、などである。
以下の実施例は、単に本発明の特定の具体的な実施形態を例証するために提示されるだけであって、請求項に示される本発明の範囲を限定するものとして解釈されてはならない。当業者であれば認識されるように、本発明の趣旨の範囲内にて、他の多くの変形が可能である。
実施例I
アルミナとコンポジット形成されたMTWゼオライトの押出し粒子を含む触媒を、米国特許第7,525,008B2号に従って作製した。粒子を、クロロ白金酸の溶液で含浸し、乾燥し、酸化し、還元し、硫化して、0.05質量%の白金を含有する触媒を得た。この触媒を、触媒Aと称した。
米国特許第6,143,941号の教示事項を用いて触媒を作製した。実施例Iに従って作製した、ゼオライトおよびアモルファスリン酸アルミニウムバインダーを含む参考文献の油滴法球状触媒を、硫酸アンモニウムを用いて(支持体1グラムあたり、0.82グラムの硫酸アンモニウム+10グラムの脱イオン水)60℃にてイオン交換し;デカントした後、イオン交換を繰り返し、得られたスフェアを、支持体1グラムあたり10グラムの脱イオン水で4回洗浄した。スフェアを120℃にて1時間乾燥し、乾燥空気中、350℃および550℃にて2時間焼成した。0.7質量%の硫黄含有量を有するこのスフェアを、テトラミン塩化白金(tetraamine platinum chloride)で含浸して0.04質量%の白金含有量とし、3%のスチームを含む空気中、525℃にて2時間焼成し、水素中、425℃にて4時間還元した。得られた触媒を、触媒Bと称した。
米国特許第2,620,314号に従って球状アルミナ粒子を作製し、これに、NH4OHを添加したpH9〜10のメタタングステン酸アンモニウムにより金属含浸を施して、10質量%のタングステンを含む固体強酸触媒を形成した。このコンポジットを乾燥し、乾燥空気中、350℃および550℃にて3時間焼成した。コンポジットを、クロロ白金酸および塩酸のpH9から10の水溶液で含浸し、350℃で乾燥し、50℃/時間にて550℃まで昇温し、窒素でパージし、水素中、565℃にて1時間還元し、これを触媒Cと称した。
米国特許第7,297,830号に従って、1/16インチのガンマ−アルミナコア上にMTWゼオライトの活性層を含む粒子を作製し、10%のMTW(Si/Al2比 40)の150ミクロンの層を得た。この粒子を、さらに、NH4OHを添加してpHを10としたメタタングステン酸アンモニウムで含浸して、10質量%のタングステンを含む固体強酸触媒を形成し、これをスチーム処理し、乾燥空気中、350℃および550℃にて3時間焼成した。このコンポジットを、米国特許第7,297,830号の実施例IIIに従ってクロロ白金酸および塩酸のpH9から10の水溶液で含浸し、白金の90%以上が外側ゼオライト層中に濃縮された触媒を得た。このコンポジットを乾燥し、焼成し、続いて、米国特許第7,297,830号の実施例IIIに従ってクロロ白金酸および塩酸の水溶液で含浸し、白金の90%以上が外側ゼオライト層中に濃縮された、0.28質量%の白金を含む触媒を得た。この粒子を焼成し、還元して、触媒Dを得た。
これら4つの触媒A〜Dを、C8芳香族中の非芳香族の変換について、質量%での以下の組成を有する非平衡C8芳香族フィードを処理するパイロットプラントフロー反応器を用いて評価した。
これら4つの触媒を、以下の条件で試験した:
時間あたり重量空間速度 12
水素/炭化水素モル比 4
385℃/395℃/405℃の各々にて1〜2時間
%での変換率は以下の通りであった:
Claims (8)
- 濃度がより高い非平衡C8芳香族化合物および濃度がより低い非芳香族化合物を含む炭化水素フィード混合物のエチルベンゼン及び非芳香族化合物の濃度を低下させる方法であって、
タングステン成分およびアルミナから本質的になる第一の触媒、ならびに少なくとも1つの白金族金属成分を元素ベースで0.01から0.2質量%含有する第二の触媒を含むデュアル触媒系と前記フィード混合物とを、300℃から550℃の温度、100kPaから5MPaの圧力、および前記デュアル触媒系に対して0.5から50時間−1の時間あたり液空間速度を含む炭化水素変換条件にて接触させることを含む、
方法。 - 前記非芳香族化合物の濃度が、前記フィード混合物の0.5から10質量%である、請求項1に記載の方法。
- 前記第一の触媒が、元素ベースで0.01から0.3質量%の白金を含む、請求項1に記載の方法。
- 前記第一の触媒が、層状スフェアを含む、請求項1に記載の方法。
- 前記第一および第二の触媒が、順に積み重ねられる、請求項1に記載の方法。
- 前記触媒系が、前記第一および第二の触媒の物理的混合物である、請求項1に記載の方法。
- 前記第一および第二の触媒が、同じ触媒粒子上に含有されている、請求項1に記載の方法。
- 前記第一の触媒が、前記第二の触媒の表面上の層を構成する、請求項7に記載の方法。
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US201161559226P | 2011-11-14 | 2011-11-14 | |
US61/559,226 | 2011-11-14 | ||
PCT/US2012/061880 WO2013074264A1 (en) | 2011-11-14 | 2012-10-25 | Aromatics isomerization using a dual-catalyst system |
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KR (1) | KR101622495B1 (ja) |
CN (1) | CN103930389A (ja) |
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RU (1) | RU2564526C1 (ja) |
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US3856872A (en) | 1973-09-13 | 1974-12-24 | Mobil Oil Corp | Xylene isomerization |
FR2312552A2 (fr) * | 1975-05-28 | 1976-12-24 | Raffinage Cie Francaise | Catalyseurs d'hydrotraitement d'hydrocarbures et procede de preparation desdits catalyseurs |
JPS6022932A (ja) * | 1984-03-19 | 1985-02-05 | Teijin Yuka Kk | 触媒組成物 |
US4899011A (en) * | 1986-01-15 | 1990-02-06 | Mobil Oil Corporation | Xylene isomerization process to exhaustively convert ethylbenzene and non-aromatics |
JPH0627078B2 (ja) * | 1986-03-31 | 1994-04-13 | 軽質留分新用途開発技術研究組合 | パラキシレンの製造方法 |
CA2174045C (en) * | 1995-04-24 | 2003-01-28 | John Ivor Hammerman | C8 aromatics isomerization using catalyst containing modified silicoaluminophosphate molecular sieve |
CN1177783C (zh) * | 1998-08-25 | 2004-12-01 | 埃克森美孚石油公司 | 对-二甲苯的生产方法 |
US6512155B1 (en) | 2000-04-25 | 2003-01-28 | Uop Llc | Process for the activation of an alkylaromatic isomerization catalyst by water |
JP4713716B2 (ja) * | 2000-09-04 | 2011-06-29 | ユーオーピー エルエルシー | 選択的キシレン異性化及びエチルベンゼン転化方法 |
MXPA05007320A (es) * | 2003-01-27 | 2005-09-30 | Uop Llc | Proceso para la activacion de un catalizador de isomerizacion de sustancias alquiloaromaticas por agua. |
US7247762B2 (en) * | 2003-09-12 | 2007-07-24 | Exxonmobil Chemical Patents Inc. | Process for xylene isomerization and ethylbenzene conversion |
EP1699556A2 (en) | 2003-12-30 | 2006-09-13 | Uop Llc | Process and catalyst for c8 alkylaromatic isomerization |
US20050197518A1 (en) * | 2004-03-04 | 2005-09-08 | Miller Jeffrey T. | Method of converting C9 aromatics-comprising mixtures to xylene isomers |
US7368620B2 (en) | 2005-06-30 | 2008-05-06 | Uop Llc | Two-stage aromatics isomerization process |
US7297830B2 (en) | 2005-09-14 | 2007-11-20 | Uop Llc | Process for isomerizing non-equilibrium xylene-containing feed streams |
FR2895283B1 (fr) * | 2005-12-22 | 2008-02-01 | Inst Francais Du Petrole | Catalyseur comprenant une zeolithe euo, une zeolithe 10mr et une zeolithe 12mr et son utilisation en isomerisation des composes c8 aromatiques |
JP4830944B2 (ja) * | 2007-03-29 | 2011-12-07 | 東レ株式会社 | エチルベンゼンの脱アルキル化及びキシレンの異性化二元機能触媒 |
FR2915113B1 (fr) * | 2007-04-23 | 2009-06-26 | Inst Francais Du Petrole | Zeolithe eu-1 modifiee et son utilisation en isomerisation des composes c8 aromatiques. |
US20090093662A1 (en) * | 2007-10-08 | 2009-04-09 | Whitchurch Patrick C | Aromatic isomerization catalyst |
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AR088855A1 (es) | 2014-07-10 |
WO2013074264A1 (en) | 2013-05-23 |
JP2014533269A (ja) | 2014-12-11 |
TW201323083A (zh) | 2013-06-16 |
RU2564526C1 (ru) | 2015-10-10 |
BR112014011145A2 (pt) | 2017-05-16 |
SG11201401225PA (en) | 2014-05-29 |
CN103930389A (zh) | 2014-07-16 |
US20130123558A1 (en) | 2013-05-16 |
KR101622495B1 (ko) | 2016-05-18 |
US9309170B2 (en) | 2016-04-12 |
KR20140097363A (ko) | 2014-08-06 |
TWI490035B (zh) | 2015-07-01 |
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