JP7109571B2 - 混合キシレンおよびハイオクタン価c9+芳香族化合物の同時生産プロセス - Google Patents
混合キシレンおよびハイオクタン価c9+芳香族化合物の同時生産プロセス Download PDFInfo
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- JP7109571B2 JP7109571B2 JP2020552708A JP2020552708A JP7109571B2 JP 7109571 B2 JP7109571 B2 JP 7109571B2 JP 2020552708 A JP2020552708 A JP 2020552708A JP 2020552708 A JP2020552708 A JP 2020552708A JP 7109571 B2 JP7109571 B2 JP 7109571B2
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Description
本出願は、2018年3月30日に出願された米国特許仮出願第62/650,673号および2018年4月27日に出願された欧州特許出願第18169815.0号の優先権を主張し、これらの内容はその全体が参照によって本明細書に組み込まれる。
本開示は、ベンゼンおよび/またはトルエンを含んでいる芳香族炭化水素流れを、メタノールおよび/またはジメチルエーテルを含んでいる流れを用いて、零超から約3までの範囲の拘束指数を有するモレキュラーシーブの存在下で、最も好ましくはZSM-12の存在下でアルキル化することによって混合キシレンおよびC9+炭化水素化合物を製造するプロセスに関する。
定義
プロセス
アルキル化触媒
アルキル化条件
リアクター
供給原料
[実施例]
X線回折パターン
BETによる全表面積およびメソ細孔表面積の測定
アルファ値
吸着データ
ZSM-12の小結晶が米国特許第8,202,506号の開示に従って合成され、同特許の内容は参照によって本明細書に組み込まれた。合成されたままの材料のX線回折(XRD)パターンは、ZSM-12トポロジーの典型的な純粋相を示した。合成されたままの材料のSEMは、その材料が(0.05ミクロン未満の平均結晶サイズを有する)小結晶の凝集体から構成されていることを示す。得られたZSM-12結晶は約43のSiO2/Al2O3モル比を有していた。アルミナで結合された触媒が、約80重量%のZSM-12の合成されたままの結晶および約20重量%のアルミナ(Versal(商標)300、Honeywell UOP社から入手可能)を使用する押し出しによって形成されて、1/20インチ(1.3mm)の4葉状押し出し成形物が作られた。乾燥されて得られた押し出し成形物が窒素中で(約538℃(1000°F)で約3時間)焼成され、約1Nの硝酸アンモニウム溶液でアンモニウム交換され、そして空気中で(約538℃(1000°F)で約6時間)焼成されて、仕上げられた、酸性の、H-ZSM-12と命名された、4葉の形状をして、540のアルファ値、44.5mg/gのヘキサン吸着量およびBETによって測定された334m2/gの表面積を有する押し出し成形物として形成された。
メタノールでトルエンをアルキル化することによる混合キシレンおよびC9+芳香族の製造を検討するために、実験が、350℃の温度、600psig(4238kPa-a)の圧力および全供給原料に基いて3.5時-1のWHSVで行われた。使用された供給原料は、3:1のモル比のメタノールとトルエンとの混合物から成っていた。使用された触媒は、上に記載されたH-ZSM-12(80%のゼオライト/20%のアルミナバインダー)であり、これは約1~約3の範囲の拘束指数を有していた。この反応は下降流の固定床リアクター中で実施された。液体製品は収集され、Agilent社製6890 GCによって分析された。ガスの収率は差分によって計算された。結果が図1および図2にまとめられている。
メタノールおよびトルエンの転化率
選択率
C 9+ 芳香族分布
Claims (19)
- 混合キシレン流れおよびC9+芳香族炭化水素流れを製造するプロセスであって、以下の工程を含むプロセス:
(a)芳香族炭化水素供給原料を、アルキル化条件の下でアルキル化触媒の存在下にアルキル化剤供給原料と接触させて、前記混合キシレンおよび前記C9+芳香族炭化水素を含んでいるアルキル化芳香族製品流れを製造する工程であって、
前記芳香族炭化水素がベンゼンおよび/またはトルエンを含んでおり、前記アルキル化剤がメタノールおよび/またはジメチルエーテルを含んでおり、前記アルキル化触媒が0超~約3の範囲の拘束指数を有するモレキュラーシーブを含んでおり、およびアルキル化条件が500℃未満の温度を含み、
芳香族炭化水素供給原料とアルキル化剤供給原料とのモル比が1:1超~4:1未満の範囲にある、工程;
(b)前記アルキル化芳香族製品流れから前記混合キシレンおよび前記C9+芳香族炭化水素を含んでいる流れを回収する工程;
(c)前記混合キシレン流れをキシレン異性化装置に供給して、パラキシレンを製造する工程;
(d)前記C9+芳香族炭化水素流れを分離装置に供給して、少なくともC9芳香族炭化水素流れを回収する工程であって、前記C9芳香族炭化水素流れがトリメチルベンゼンの混合物およびエチルメチルベンゼンの混合物を含んでいる工程;
(e)前記C9芳香族炭化水素流れを分離装置に供給して、トリメチルベンゼンの前記混合物を含んでいる流れおよび/またはエチルメチルベンゼンの混合物を含んでいる前記流れを回収する工程;および
(f)トリメチルベンゼンの前記混合物を含んでいる前記流れおよび/またはエチルメチルベンゼンの混合物を含んでいる前記流れを自動車燃料ブレンド成分として供給する工程。 - 前記モレキュラーシーブが、MTW、BEA*、FAUまたはMORの骨格構造を有する、請求項1に記載のプロセス。
- 前記MTW骨格構造を有する前記モレキュラーシーブが、ZSM-12である、請求項2に記載のプロセス。
- 前記BEA*骨格構造を有する前記モレキュラーシーブが、ゼオライトベータである、請求項2に記載のプロセス。
- 前記FAU骨格構造を有する前記モレキュラーシーブが、フォージャサイト、ゼオライトY、超安定Y(USY)、脱アルミニウムY(Deal Y)、希土類Y(REY)、超疎水性Yおよびこれらの混合物から成る群から選ばれる、請求項2に記載のプロセス。
- 前記MOR骨格構造を有する前記モレキュラーシーブが、天然のモルデナイト、TEA-モルデナイトおよびこれらの混合物から成る群から選ばれる、請求項2に記載のプロセス。
- 前記モレキュラーシーブが、ZSM-3、ZSM-4、ZSM-14、ZSM-18、ZSM-20、ZSM-38およびこれらの混合物から成る群から選ばれる、請求項1に記載のプロセス。
- 前記アルキル化芳香族製品流れが、前記混合キシレンを少なくとも約75重量%および/または前記C9+芳香族炭化水素を少なくとも約21重量%含んでおり、各重量%が前記アルキル化芳香族製品流れの重量に基いている、請求項1~7のいずれか1項に記載のプロセス。
- 前記アルキル化条件が、300℃~450℃の範囲の温度、700kPa-a~7000kPa-aの範囲の圧力および50時-1~0.5時-1の芳香族炭化水素供給原料に基いた重量時空間速度を含む、請求項1~8のいずれか1項に記載のプロセス。
- 前記アルキル化触媒が固定床に存在する、請求項1~9のいずれか1項に記載のプロセス。
- C9芳香族炭化水素流れおよびC10芳香族炭化水素流れを製造するプロセスであって、以下の工程を含むプロセス:
(a)ベンゼンおよび/またはトルエンを含んでいる芳香族炭化水素供給原料を、アルキル化条件の下でZSM-12を含んでいるアルキル化触媒の存在下に、メタノールおよび/またはジメチルエーテルを含んでいる供給原料と接触させて、前記C9芳香族炭化水素およびC10芳香族炭化水素を含んでいるアルキル化芳香族製品流れを製造する工程であって、
芳香族炭化水素供給原料と、メタノールおよび/またはジメチルエーテルを含んでいる供給原料とのモル比が約1:1超~約4:1の範囲であり、かつ前記アルキル化条件が、300℃~450℃の範囲の温度、700kPa-a~7000kPa-aの範囲の圧力および50時-1~0.5時-1の芳香族炭化水素供給原料に基いた重量時空間速度を含む工程;
(b)前記アルキル化芳香族製品流れを分離して、前記C9芳香族炭化水素流れおよび前記C10芳香族炭化水素流れを回収する工程であって、
前記C9芳香族炭化水素流れがトリメチルベンゼンの混合物およびエチルメチルベンゼンの混合物を含んでいる工程;
(c)前記C9芳香族炭化水素流れを分離装置に供給して、トリメチルベンゼンの前記混合物を含んでいる流れ、および/またはエチルメチルベンゼンの混合物を含んでいる前記流れを回収する工程;
(d)トリメチルベンゼンの前記混合物を含んでいる前記流れおよび/またはエチルメチルベンゼンの混合物を含んでいる前記流れを自動車燃料ブレンド成分として供給する工程。 - 以下の工程をさらに含む、請求項11に記載のプロセス:
(e)前記C10芳香族炭化水素流れを自動車燃料ブレンド成分として供給する工程。 - トリメチルベンゼンの前記混合物が、1,2,4-トリメチルベンゼン、1,3,5-トリメチルベンゼンおよび1,2,3-トリメチルベンゼンを含んでいる、請求項11または12に記載のプロセス。
- 以下の工程をさらに含む、請求項11~13のいずれか1項に記載のプロセス:
(f)トリメチルベンゼンの前記混合物を含んでいる前記流れを前記分離装置に供給して、1,2,4-トリメチルベンゼン、1,3,5-トリメチルベンゼンおよび1,2,3-トリメチルベンゼンを含んでいる個別の複数の流れを回収する工程。 - 以下の工程をさらに含む、請求項14に記載のプロセス:
(g)前記個別のトリメチルベンゼンの複数の流れのそれぞれを自動車燃料ブレンド成分として供給する工程。 - エチルメチルベンゼンの前記混合物が、1-エチル-2-メチルベンゼンおよび1-エチル-3-メチルベンゼンを含んでいる、請求項11~15のいずれか1項に記載のプロセス。
- 以下の工程をさらに含む、請求項16に記載のプロセス:
(h)エチルメチルベンゼンの前記混合物を含んでいる前記流れを前記分離装置に供給して、1-エチル-2-メチルベンゼンおよび1-エチル-3-メチルベンゼンを含んでいる個別の複数の流れを回収する工程。 - 以下の工程をさらに含む、請求項17に記載のプロセス:
(i)1-エチル-2-メチルベンゼンおよび1-エチル-3-メチルベンゼンを含んでいる前記個別の複数の流れのそれぞれを自動車燃料ブレンド成分として供給する工程。 - 前記アルキル化触媒が固定床に存在する、請求項11~18のいずれか1項に記載のプロセス。
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EP18169815.0 | 2018-04-27 | ||
EP18169815 | 2018-04-27 | ||
PCT/US2019/022387 WO2019190774A1 (en) | 2018-03-30 | 2019-03-15 | Process for co-production of mixed xylenes and high octane c9+ aromatics |
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WO2019190774A1 (en) | 2019-10-03 |
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