TW400372B - Removal of alkyl halides from hydrocarbon stream - Google Patents

Removal of alkyl halides from hydrocarbon stream Download PDF

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Publication number
TW400372B
TW400372B TW087121014A TW87121014A TW400372B TW 400372 B TW400372 B TW 400372B TW 087121014 A TW087121014 A TW 087121014A TW 87121014 A TW87121014 A TW 87121014A TW 400372 B TW400372 B TW 400372B
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Taiwan
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patent application
item
catalyst
scope
acid
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TW087121014A
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English (en)
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Sven Hommeltoft
Karsten Laurents
Annemarie Bauer
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Haldor Topsoe As
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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
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/06—Metal salts, or metal salts deposited on a carrier
    • C10G29/12—Halides
    • 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
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C10G29/205—Organic compounds not containing metal atoms by reaction with hydrocarbons added to the hydrocarbon oil
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1081—Alkanes
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4087—Catalytic distillation

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Catalysts (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Residential Or Office Buildings (AREA)

Description

B7 五、發明説明（f ) 本發明係有關於一種由液態碳氫化合物流中移除烷基 鹵化物之方法，該方法包含至少一種異烷烴在溫和條件及 固定床反應器中負載液相酸催化劑下與碳氫化合物流接觸 Ο 石油加工中數種製程係有關於含有催化劑之鹵化物與 在原料中之碳氫化合物反應期間轉換至烷基鹵化物。可溶 解於碳氫化合物流中之烷基鹵化物並不希望存在於得自於 該等製程中的產物。例如，異烷基氟在例如異丁烷烷基化 之HF催化方法中形成，或異烷基氯在得自於例如使用以 氯化物促進之催化劑之低碳烷同分異構化或揮發油重組之 產物。 前案技藝中由碳氫化合物基質中移除烷基氟化物的方 法通常係使用在異鏈烷烴流內的吸收作用（美國專利 4,009,222號）或在聚合樹脂上的吸收作用（美國專利 5,300,685號）。此外，已知由異鏈烷烴中回收烷基氟化物 係藉由以HF萃取（美國專利3,784,628號）或蒸餾（美國 專利 3,769，177 號）。 經發現烷基圍化物可有效地由液態碳氫化合物流中移 除’其係在低溫且存有酸催化劑下藉由與異烷烴及/或芳 香系碳氫化合物反應。 因此’本發明提供一種由液態碳氫化合物基質中移除 烷基鹵化物之方法’該方法包含在存有負載於固態載體上 之酸催化劑下該_化物與異烷烴及/或芳香系碳氫化合物 反應。 -------2_ __ 本紙張尺度適用中國國家標华（CNS ) A4規格（210 X 297公麓） 經濟部中央棣準局男工消費合作衽印製 A7 ______B7 五、發明説明（> ) 經本發明方法處理之烷基鹵化物與異烷烴或芳香族碳 氫化合物反應以形成烷基化之基質及齒化氫。 特別有用的碳氫化合物爲通常使用於碳氫化合物之院 基化者，其包括異丁烷和高碳異烷烴或芳香族碳氫化合物 0 較佳之酸催化劑爲具有高酸度者，且其等包括過氟化 之磺酸，例如三氟甲基磺酸和過氟烷基磺酸。該載體物質 係方便地選自包含耐酸耐火材料，且其較佳爲矽膠。該載 體物質因此可爲任何形狀，如顆粒，錠劑，圓球和相似者 ，或可爲整體形式(monolithic form)。 在進一步較佳具體實施例中，本發明方法係進行於存 有三氟甲基磺酸負載於矽膠粒子的固定床上。本發明將藉 由下列實施例而變得更顯而易知。 實施例 實施例1 與異丁烷反應以移除次丁基氯。 該反應係進行於裝載有矽膠（Merck 100, 0.2-0.5釐米 粒子大小）的100毫升反應器中。反應器在定溫的水浴中 維持在0°C及40°C的溫度。6毫升三氟甲基磺酸被注入至 反應器內且含有0.1重量％之次丁基氯和5重量％之2-丁 烯於異丁烷的原料流以流速2.5-3克/分通經反應器。壓力 保持在大約15巴(bar)以確定原料流爲液相。次丁基氯的轉 化係藉由廢水流的GC分析來測量。在0°C時，在原料流 中之65%次丁基氯含量被移除且在40°C時高於98%。 -----------_ 本紙張尺度適用中國國家標準（CNS ) Λ4規格（210X 297公釐） I. I I I I I 裝—— 訂 ^ 線 (請先閱讀背面·5·注意乾項再^本買) A7 B7 五、發明説明（）） 實施例2 異丙基氟的移除。 如同於實施例1中所述的反應器被維持於30°C。6毫 升之三氟甲基磺酸被加至反應器中且含有0.2重量％之異 丙基氟和5重量％之2-丁烯於異丁基之原料流以流速8克 /分及壓力大約15巴通經反應器。異丙基氟的轉化率係藉 由反應器中廢水流的GC分析來測量。異丙基氟之實質量 (>99% )藉由在原料流中之反應被移除。 實施例3 在未存有鏈烯之原料流中異丙基氟的移除。 異丙基氟的移除係進行於如上文實施例2中所述之相 似方法，除了使用含有5重量％異丙基氟於異丁烷之原料 流。一段時間後，由廢水流的分析顯示移除異丙基氟，且 形成之碳氫化合物產物所具有之組成相似於異丁烷與丙稀 烷基化所形成之烷基化產物者。 ----------裝---.—---訂.—----線' ·*<ls (請先閲讀背面之注意事項再本頁) 經濟部中央標準局貝工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）

Claims (1)

  1. A8 Ci 】Di 申請專利範圍 1·一種由液態碳氫化合物基質中移除烷基鹵化物之 方法，該方法包含在存有負載於固態載體材料上之酸催化 劑下該鹵化物與異烷烴及/或芳香系碳氫化合物反應。 2 ·根據申請專利範圍第1項之方法，其中該催化劑 爲液態超酸。 3 ·根據申請專利範圍第1項之方法，其中該催化劑 爲過氟化磺酸。 4 ·根據申請專利範圍第1項之方法，其中該催化劑 爲三氟甲基磺酸。 5 ·根據申請專利範圍第1項之方法，其中該固態載 體材料爲矽膠。 6 ·根據申請專利範圍第1項之方法，其中該碳氫化 合物基質含有異丁烷。 ---------装---_--,--訂-------味 • - · (請先閲讀背面之注意事項再填寫本貢) 經濟部中央揉率局貝工消费合作社印製 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐）
TW087121014A 1997-12-19 1998-12-17 Removal of alkyl halides from hydrocarbon stream TW400372B (en)

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DK199701494A DK149497A (da) 1997-12-19 1997-12-19 Fremstilling til fjernelse af alkylhalider fra en carbonstrøm

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US (1) US6043404A (zh)
EP (1) EP0924287B1 (zh)
JP (1) JPH11269102A (zh)
KR (1) KR19990063169A (zh)
AT (1) ATE226620T1 (zh)
CA (1) CA2256215A1 (zh)
DE (1) DE69808875T2 (zh)
DK (1) DK149497A (zh)
EA (1) EA002589B1 (zh)
ES (1) ES2186079T3 (zh)
NO (1) NO315975B1 (zh)
TW (1) TW400372B (zh)

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Publication number Priority date Publication date Assignee Title
US8093441B2 (en) 2008-12-18 2012-01-10 Exxonmobil Research And Engineering Company Removal of light fluoroalkanes from hydrocarbon streams

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2463077A (en) * 1943-08-30 1949-03-01 Universal Oil Prod Co Process for treating hydrocarbon mixtures to remove halogens therefrom
US2636912A (en) * 1949-07-29 1953-04-28 Phillips Petroleum Co Dehydrofluorination of hydrocarbons
US3211802A (en) * 1962-08-09 1965-10-12 Phillips Petroleum Co Catalytic alkylation process
US3784628A (en) * 1971-07-06 1974-01-08 Phillips Petroleum Co Removing alkyl fluoride with hf acid from an alkylation hydrocarbon effluent
US3769177A (en) * 1971-11-10 1973-10-30 Monsanto Co Purification of carboxylic acids by plural stage distillation with side stream draw-offs
US4009222A (en) * 1974-11-04 1977-02-22 Uop Inc. Recovery of gaseous hydrogen fluoride stream in alkylation process
US4229611A (en) * 1979-04-11 1980-10-21 Exxon Research & Engineering Co. Isomerization alkylation systems
US4990716A (en) * 1989-06-09 1991-02-05 The Dow Chemical Company Preparation of diphenylmethanes
US5220096A (en) * 1991-06-21 1993-06-15 Mobil Oil Corporation Liquid acid alkylation catalyst composition and isoparaffin:olefin alkylation process
US5300685A (en) * 1991-11-25 1994-04-05 Hoechst Celanese Corporation Removal of halide impurities from organic liquids
US5672797A (en) * 1993-07-19 1997-09-30 Uop Alkylation of aromatics using a metal cation-modified friedel-crafts type catalyst
US5763729A (en) * 1994-11-14 1998-06-09 Uop Alkylation of alkanes with alkyl halides
US5565617A (en) * 1995-05-22 1996-10-15 Uop Process for purifying an alkylate stream

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EP0924287A3 (en) 1999-11-24
EP0924287A2 (en) 1999-06-23
ATE226620T1 (de) 2002-11-15
NO985857L (no) 1999-06-21
US6043404A (en) 2000-03-28
EA002589B1 (ru) 2002-06-27
CA2256215A1 (en) 1999-06-19
NO985857D0 (no) 1998-12-14
NO315975B1 (no) 2003-11-24
DK149497A (da) 1999-06-20
ES2186079T3 (es) 2003-05-01
KR19990063169A (ko) 1999-07-26
JPH11269102A (ja) 1999-10-05
EA199801022A2 (ru) 1999-08-26
DE69808875D1 (de) 2002-11-28
EA199801022A3 (ru) 1999-12-29
EP0924287B1 (en) 2002-10-23
DE69808875T2 (de) 2003-03-13

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