JPH05508151A - 液体オニウムポリ(フッ化水素)を使用する環境上安全な接触アルキル化 - Google Patents
液体オニウムポリ(フッ化水素)を使用する環境上安全な接触アルキル化Info
- Publication number
- JPH05508151A JPH05508151A JP91508649A JP50864991A JPH05508151A JP H05508151 A JPH05508151 A JP H05508151A JP 91508649 A JP91508649 A JP 91508649A JP 50864991 A JP50864991 A JP 50864991A JP H05508151 A JPH05508151 A JP H05508151A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- carbon atoms
- reaction
- alkylation
- cocatalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- 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
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- 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
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/60—Catalytic processes with halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1206—Hydrogen fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/24—Nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (20)
- 1.3−12個の炭素原子を有し、場合により1−4個の炭素原子のアルキル基 を含む脂肪族炭化水素を、2−12個の炭素原子を有し、場合により1−4個の 炭素原子のアルキル基を含むアルケニル炭化水素を用いて、反応媒体および触媒 としての液体オニウムポリフッ化水素複合体の存在下に、アルキル化生成物を形 成するのに十分な温度、圧力および時間でアルキル化する方法。
- 2.前記温度が−20℃から70℃の範囲であり、前記圧力が大気圧から200 psiの範囲である、請求項1記載の方法。
- 3.前記反応をバッチ式または連続流動条件下で行う、請求項1記載の方法。
- 4.脂肪族炭化水素対アルケニル炭化水素の重量比が約2:1から10:1の範 囲である、請求項1記載の方法。
- 5.前記ポリフッ化水素複合体が約5−30重量%のアンモニウム、メチルアミ ン、エチルアミン、プロピルアミン、ブチルアミン、ペンチルアミン、ピリジン 、ピコリン、トリエタノールアミン、メラミン、またはヘキサメチレンテトラミ ンのうちの1種と、約70−95重1%のフッ化水素を含む、請求項1記載の方 法。
- 6.前記アルケニル化合物を脂肪族炭化水素と触媒複合体の混合物に少しずつ加 える、請求項1記載の方法。
- 7.前記反応混合物に助触媒を加えることをさらに含む、請求項1記載の方法。
- 8.前記助触媒がルイス酸ハロゲン化物、バーフルオロスルホネート、またはバ ーフルオロアルカンスルホン酸である、請求項7記載の方法。
- 9.前記助触媒が前記反応混合物の約0.1−10重量%の量で存在する、請求 項7記載の方法。
- 10.反応媒体および触媒としての液体オニウムポリフッ化水素複合体の存在下 に、−20℃から70℃の範囲の温度および大気圧から200psiの範囲の圧 力で、ハイオクタンアルキル化生成物を形成するのに十分な時間、イソブタンを イソブチレンでアルキル化する方法。
- 11.前記イソブチレンをイソブタンと触媒複合体の混合物に少しずつ加える、 請求項10記載の方法。
- 12.約2:1から10:1の範囲のイソブタン/イソブチレン重量比を用いて 、前記反応をパッチ式または連続流動条件下で行う、請求項11記載の方法。
- 13.前記ポリフッ化水素複合体が約5−30重量%のアンモニウム、メチルア ミン、エチルアミン、プロピルアミン、ブチルアミン、ペンチルアミン、ピリジ ン、ピコリン、トリエタノールアミン、メラミン、またはヘキサメチレンテトラ ミンのうちの1種と、約70−95重量%のフッ化水素を含む、請求項12記載 の方法。
- 14.前記反応混合物にルイス酸ハロゲン化物、パーフルオロスルホネート、ま たはパーフルオロアルカンスルホン酸のうちの1種である助触媒を加えることを さらに含む、請求項13記載の方法。
- 15.前記助触媒がルイス酸ハロゲン化物、パーフルオロスルホネート、または パーフルオロアルカンスルホン酸のうちの1種である、請求項14記載の方法。
- 16.前記助触媒が前記反応混合物の約0.1−10重量%の量で存在する、請 求項15記載の方法。
- 17.3−12個の炭素原子を有し、場合により1−4個の炭素原子のアルキル 基を含む脂肪族炭化水素を、2−12個の炭素原子を有し、場合により1−4個 の炭素原子のアルキル基を含むアルケニル炭化水素でアルキル化する方法であっ て、脂肪族炭化水素対アルケニル炭化水素の重量比が約2:1から10:1の範 囲であり、反応媒体および触媒としての約5−30重量%のアンモニア、ピリジ ン、ピコリン、メチルアミン、エチルアミン、プロピルアミン、ブチルアミン、 トリエタノールアミン、メラミン、またはヘキサメチレンテトラミンと約70− 95重量%のフッ化水素を含む液体オニウムポリフッ化水素複合体の存在下に、 アルキル化生成物を形成するのに十分な温度、圧力および時間で該アルキル化反 応を行うことから成る上記方法。
- 18.前記反応をバッチ式または連続流動条件下で行う、請求項17記載の方法 。
- 19.前記反応混合物の約0.1−10重量%の量の助触媒をさらに含む、請求 項18記載の方法。
- 20.前記助触媒がルイス酸ハロゲン化物、パーフルオロスルホネート、または バーフルオロアルカンスルホン酸である、請求項19記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51165590A | 1990-04-20 | 1990-04-20 | |
US511.655 | 1990-09-20 | ||
US07/585,540 US5073674A (en) | 1990-04-20 | 1990-09-20 | Environmentally safe catalytic alkyation using liquid onium poly (hydrogen fluorides) |
US585.540 | 1990-09-20 | ||
PCT/US1991/002701 WO1991016283A1 (en) | 1990-04-20 | 1991-04-19 | Environmentally safe catalytic alkylation using liquid onium poly (hydrogen fluorides) |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH05508151A true JPH05508151A (ja) | 1993-11-18 |
JP2907397B2 JP2907397B2 (ja) | 1999-06-21 |
Family
ID=27057295
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3508649A Expired - Fee Related JP2907397B2 (ja) | 1990-04-20 | 1991-04-19 | 液体オニウムポリ(フッ化水素)を使用する環境上安全な接触アルキル化 |
Country Status (11)
Country | Link |
---|---|
US (1) | US5073674A (ja) |
EP (1) | EP0592431B1 (ja) |
JP (1) | JP2907397B2 (ja) |
AT (1) | ATE158787T1 (ja) |
AU (1) | AU636824B2 (ja) |
BR (1) | BR9106362A (ja) |
CA (1) | CA2080829C (ja) |
DE (1) | DE69127831T2 (ja) |
ES (1) | ES2106788T3 (ja) |
NO (1) | NO304019B1 (ja) |
WO (1) | WO1991016283A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003073873A (ja) * | 2001-08-31 | 2003-03-12 | Permelec Electrode Ltd | 有機エーテル化合物の電解フッ素化方法 |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5334569A (en) * | 1987-02-24 | 1994-08-02 | Nalco Chemical Company | Alkylation aid |
US5196628A (en) * | 1991-06-21 | 1993-03-23 | Mobil Oil Corporation | Liquid acid alkylation catalyst and isoparaffin:olefin alkylation process |
US5569807A (en) * | 1992-05-01 | 1996-10-29 | Phillips Petroleum Company | Isoparaffin-olefin alkylation |
US5220096A (en) * | 1991-06-21 | 1993-06-15 | Mobil Oil Corporation | Liquid acid alkylation catalyst composition and isoparaffin:olefin alkylation process |
US5292982A (en) * | 1991-06-21 | 1994-03-08 | Mobil Oil Corporation | Liquid acid alkylation catalyst and isoparaffin-olefin alkylation process |
AU2252992A (en) * | 1991-06-21 | 1993-01-25 | Mobil Oil Corporation | Improved liquid acid alkylation catalyst and isoparaffin:olefin alkylation process |
US5202518A (en) * | 1991-09-18 | 1993-04-13 | Mobil Oil Corporation | Liquid acid alkylation catalyst and isoparaffin:olefin alkylation process |
US5534657A (en) * | 1991-06-21 | 1996-07-09 | Phillips Petroleum Company | Isoparaffin-olefin alkylation |
AU671593B2 (en) | 1991-06-21 | 1996-09-05 | Uop Llc | Method for increasing rainout from autorefrigerated vaporous cloud containing hydrofluoric acid |
AU2679092A (en) * | 1991-09-25 | 1993-04-27 | Mobil Oil Corporation | Improved liquid acid alkylation catalyst and isoparaffin:olefin alkylation process |
US5414186A (en) * | 1992-08-05 | 1995-05-09 | Mobil Oil Corporation | Liquid acid alkylation catalyst and isoparaffin-olefin alkylation process |
US5277881A (en) * | 1992-09-14 | 1994-01-11 | Texaco Inc. | Hydrogen fluoride alkylation apparatus and vapor recovery method |
US5286456A (en) * | 1992-09-24 | 1994-02-15 | Mobil Oil Corporation | Containment of an aerosolable liquid jet |
US5465536A (en) * | 1992-09-24 | 1995-11-14 | Mobil Oil Corporation | Containment of heavy vapor clouds and aerosols |
US5304522A (en) * | 1993-06-01 | 1994-04-19 | Mobil Oil Corporation | Liquid acid regeneration method |
USH2029H1 (en) * | 1993-11-01 | 2002-06-04 | Texaco Inc. | Environmental safety apparatus for airborne hydrogen fluoride recovery and method |
US5407830A (en) * | 1993-12-01 | 1995-04-18 | Mobil Oil Corporation | Control of low inventory alkylation unit |
US5763728A (en) * | 1993-12-29 | 1998-06-09 | Uop | Recovery and recycle of HF-amine complex in HF alkylation |
FR2725919B1 (fr) * | 1994-10-24 | 1996-12-13 | Inst Francais Du Petrole | Composition catalytique et procede pour l'alkylation d'hydrocarbures aliphatiques |
US5859305A (en) * | 1995-01-10 | 1999-01-12 | Texaco Inc | Method for optimizing hydrogen fluoride alxylation and increasing process safety |
EP0739871B1 (en) * | 1995-04-25 | 1999-12-15 | Uop | Recovery and recycle of HF-amine complex in HF alkylation |
CN1060754C (zh) * | 1995-05-09 | 2001-01-17 | 环球油品公司 | 在hf烷基化中hf-胺复合物的再生和循环利用 |
US5948947A (en) * | 1996-01-31 | 1999-09-07 | Uop Llc | Alkylation process with separate rejection of light and heavy acid soluble oils |
US5663474A (en) * | 1996-03-07 | 1997-09-02 | Alliedsignal Inc. | Alkylation process using hydrogen fluoride-containing alkylation catalysts |
US5785770A (en) * | 1996-05-30 | 1998-07-28 | Advance Research Chemicals, Inc. | Brazing flux |
US6018088A (en) * | 1997-05-07 | 2000-01-25 | Olah; George A. | Superacid catalyzed formylation-rearrangement of saturated hydrocarbons |
US6677269B2 (en) | 2001-05-17 | 2004-01-13 | George A Olah | Environmentally safe alkylation of aliphatic and aromatic hydrocarbons with olefins using solid HF-equivalent catalysts |
CN1203032C (zh) * | 2002-11-12 | 2005-05-25 | 石油大学(北京) | 以复合离子液体为催化剂制备烷基化油剂的方法 |
US7955738B2 (en) * | 2004-03-05 | 2011-06-07 | Honeywell International, Inc. | Polymer ionic electrolytes |
US8148533B2 (en) * | 2004-03-05 | 2012-04-03 | Honeywell International Inc. | Ionic liquids of heterocyclic amines |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE243923C (ja) * | ||||
US3888935A (en) * | 1971-10-18 | 1975-06-10 | Universal Oil Prod Co | Process for producing alkyl fluorides from mono-olefins |
US4065405A (en) * | 1976-12-03 | 1977-12-27 | Exxon Research And Engineering Company | Recovery of tantalum and/or niobium pentafluorides from a hydrocarbon conversion catalyst |
US4071576A (en) * | 1977-02-28 | 1978-01-31 | Exxon Research & Engineering Co. | Process for regenerating fluorosulfuric acid catalyst |
US4096197A (en) * | 1977-02-28 | 1978-06-20 | Exxon Research & Engineering Co. | Process for regenerating fluorosulfuric acid catalyst |
US4167535A (en) * | 1978-04-24 | 1979-09-11 | Uop Inc. | Isoparaffin-olefin alkylation utilizing liquefied normal paraffin concentrate in the reaction vessel |
IT1129809B (it) * | 1979-03-26 | 1986-06-11 | Ugine Kuhlmann | Composizione catalitica per la conversione di idrocarburi e procedimento per la disidratazione di acidi perfluoroalcansolfonici destinati a fare parte bella composizione |
US4513164A (en) * | 1981-09-01 | 1985-04-23 | Olah George A | Condensation of natural gas or methane into gasoline range hydrocarbons |
US4663026A (en) * | 1984-11-28 | 1987-05-05 | Mobil Oil Corporation | Solvent extraction and purification of acid soluble oil from an HF alkylation unit |
US4544794A (en) * | 1984-12-10 | 1985-10-01 | Atlantic Richfield Company | Alkylation aide for sulfuric acid catalyzed alkylation units |
US4891466A (en) * | 1987-11-23 | 1990-01-02 | Uop | HF alkylation process |
US4783567A (en) * | 1987-11-23 | 1988-11-08 | Uop Inc. | HF alkylation process |
US4985220A (en) * | 1988-08-08 | 1991-01-15 | Mobil Oil Corporation | Hydrogen fluoride vapor containment |
US4962268A (en) * | 1989-02-22 | 1990-10-09 | Phillips Petroleum Company | Alkylation catalyst isolation |
-
1990
- 1990-09-20 US US07/585,540 patent/US5073674A/en not_active Expired - Lifetime
-
1991
- 1991-04-19 AU AU77739/91A patent/AU636824B2/en not_active Expired
- 1991-04-19 JP JP3508649A patent/JP2907397B2/ja not_active Expired - Fee Related
- 1991-04-19 DE DE69127831T patent/DE69127831T2/de not_active Expired - Lifetime
- 1991-04-19 EP EP91919023A patent/EP0592431B1/en not_active Expired - Lifetime
- 1991-04-19 AT AT91919023T patent/ATE158787T1/de active
- 1991-04-19 CA CA002080829A patent/CA2080829C/en not_active Expired - Lifetime
- 1991-04-19 ES ES91919023T patent/ES2106788T3/es not_active Expired - Lifetime
- 1991-04-19 BR BR919106362A patent/BR9106362A/pt not_active Application Discontinuation
- 1991-04-19 WO PCT/US1991/002701 patent/WO1991016283A1/en active IP Right Grant
-
1992
- 1992-10-15 NO NO924002A patent/NO304019B1/no not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003073873A (ja) * | 2001-08-31 | 2003-03-12 | Permelec Electrode Ltd | 有機エーテル化合物の電解フッ素化方法 |
Also Published As
Publication number | Publication date |
---|---|
AU636824B2 (en) | 1993-05-06 |
NO924002L (no) | 1992-10-15 |
BR9106362A (pt) | 1993-04-27 |
ATE158787T1 (de) | 1997-10-15 |
CA2080829A1 (en) | 1991-10-21 |
EP0592431B1 (en) | 1997-10-01 |
EP0592431A4 (en) | 1993-06-07 |
DE69127831D1 (de) | 1997-11-06 |
NO304019B1 (no) | 1998-10-12 |
AU7773991A (en) | 1991-11-11 |
CA2080829C (en) | 1997-11-04 |
EP0592431A1 (en) | 1994-04-20 |
ES2106788T3 (es) | 1997-11-16 |
US5073674A (en) | 1991-12-17 |
NO924002D0 (no) | 1992-10-15 |
JP2907397B2 (ja) | 1999-06-21 |
DE69127831T2 (de) | 1998-02-19 |
WO1991016283A1 (en) | 1991-10-31 |
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