AU2006222911B2 - Processes for the isomerization of normal butane to isobutane - Google Patents
Processes for the isomerization of normal butane to isobutane Download PDFInfo
- Publication number
- AU2006222911B2 AU2006222911B2 AU2006222911A AU2006222911A AU2006222911B2 AU 2006222911 B2 AU2006222911 B2 AU 2006222911B2 AU 2006222911 A AU2006222911 A AU 2006222911A AU 2006222911 A AU2006222911 A AU 2006222911A AU 2006222911 B2 AU2006222911 B2 AU 2006222911B2
- Authority
- AU
- Australia
- Prior art keywords
- membrane
- isomerization
- isobutane
- fraction
- normal butane
- 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.)
- Ceased
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- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 title claims description 206
- 238000006317 isomerization reaction Methods 0.000 title claims description 118
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title claims description 109
- 239000001282 iso-butane Substances 0.000 title claims description 103
- 238000000034 method Methods 0.000 title claims description 69
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- 239000001273 butane Substances 0.000 claims description 10
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 33
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
- B01D61/362—Pervaporation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/144—Purification; Separation; Use of additives using membranes, e.g. selective permeation
-
- 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/20—C2-C4 olefins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US66114305P | 2005-03-11 | 2005-03-11 | |
US60/661,143 | 2005-03-11 | ||
PCT/US2006/009627 WO2006099566A1 (en) | 2005-03-11 | 2006-03-10 | Processes for the isomerization of normal butane to isobutane |
Publications (2)
Publication Number | Publication Date |
---|---|
AU2006222911A1 AU2006222911A1 (en) | 2006-09-21 |
AU2006222911B2 true AU2006222911B2 (en) | 2009-06-04 |
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AU2006222911A Ceased AU2006222911B2 (en) | 2005-03-11 | 2006-03-10 | Processes for the isomerization of normal butane to isobutane |
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EP (1) | EP1856016A4 (ko) |
KR (1) | KR100945405B1 (ko) |
CN (1) | CN101171213A (ko) |
AU (1) | AU2006222911B2 (ko) |
BR (1) | BRPI0608998A2 (ko) |
CA (1) | CA2601219C (ko) |
RU (1) | RU2368594C2 (ko) |
WO (1) | WO2006099566A1 (ko) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US8841499B2 (en) * | 2012-11-08 | 2014-09-23 | Uop Llc | Methods and apparatuses for isomerization of paraffins |
US8864952B2 (en) * | 2012-12-14 | 2014-10-21 | Uop Llc | Apparatuses and methods for separating paraffin isomerization-zone effluents |
US9567271B2 (en) * | 2014-09-03 | 2017-02-14 | Uop Llc | Process for the recovery of paraffins from an isomerization effluent |
CN107304152A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种异丁烷生产装置及方法 |
CN107304151A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种制备异丁烷的装置及方法 |
CN107304153A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种加氢和异构化制备异丁烷的装置及方法 |
CN107304156A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种生产异丁烷的装置及方法 |
CN107304155A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种异丁烷的生产装置及方法 |
CN107304158B (zh) * | 2016-04-22 | 2021-08-27 | 中国石化工程建设有限公司 | 一种生产异丁烷的组合装置及方法 |
CN107304154A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种加氢和异构化生产异丁烷的装置及方法 |
CN107304157A (zh) * | 2016-04-22 | 2017-10-31 | 中国石化工程建设有限公司 | 一种加氢和异构化生产异丁烷的组合装置及方法 |
CN109265308A (zh) * | 2018-11-07 | 2019-01-25 | 厦门大学 | 一种使用固体酸双功能催化剂的正丁烷异构化的生产方法 |
CN111171856A (zh) * | 2018-11-13 | 2020-05-19 | 中国科学院大连化学物理研究所 | 一种碳分子筛膜用于c4-c6正异构烷烃的分离方法 |
CN110344171A (zh) * | 2019-06-20 | 2019-10-18 | 南通明富纺织品有限公司 | 一种吸湿保暖的仿麻面料及其制备方法 |
CN113277927B (zh) * | 2021-05-28 | 2022-08-16 | 中国科学院宁波材料技术与工程研究所 | 一种微孔分子筛在正丁烷异丁烷吸附分离中的应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4717784A (en) * | 1986-12-10 | 1988-01-05 | Shell Oil Company | Total isomerization process with mono-methyl-branched plus normal paraffin recycle stream |
WO2005049766A1 (fr) * | 2003-11-14 | 2005-06-02 | Institut Francais Du Petrole | Procede de production d'essences a haut indice d'octane a partir d'une coupe c5/c6 utilisant une unite de separation par membrane |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4347399A (en) * | 1981-06-03 | 1982-08-31 | Uop Inc | Isomerization of normal butane |
US5069794A (en) * | 1990-06-05 | 1991-12-03 | Mobil Oil Corp. | Separation of mixture components over membrane composed of a pure molecular sieve |
FR2695635B1 (fr) * | 1992-09-14 | 1994-11-04 | Inst Francais Du Petrole | Procédé d'isomérisation de n-butane combinant une étape de déisobutanisation et une étape d'adsorption. |
GB9413863D0 (en) * | 1994-07-08 | 1994-08-24 | Exxon Chemical Patents Inc | Molecular sieves and processes for their manufacture |
US6818333B2 (en) * | 2002-06-03 | 2004-11-16 | Institut Francais Du Petrole | Thin zeolite membrane, its preparation and its use in separation |
AU2006223222B2 (en) * | 2005-03-11 | 2009-06-18 | Uop Llc | Processes for the isomerization of feedstocks comprising paraffins of 5 to 7 carbon atoms |
WO2006099287A1 (en) * | 2005-03-11 | 2006-09-21 | Uop Llc | Processes for the isomerization of paraffins of 5 and 6 carbon atoms with methylcyclopentane recovery |
-
2006
- 2006-03-10 KR KR1020077023094A patent/KR100945405B1/ko active IP Right Grant
- 2006-03-10 RU RU2007137661/04A patent/RU2368594C2/ru not_active IP Right Cessation
- 2006-03-10 EP EP06738661.5A patent/EP1856016A4/en not_active Withdrawn
- 2006-03-10 BR BRPI0608998-4A patent/BRPI0608998A2/pt not_active IP Right Cessation
- 2006-03-10 WO PCT/US2006/009627 patent/WO2006099566A1/en active Application Filing
- 2006-03-10 AU AU2006222911A patent/AU2006222911B2/en not_active Ceased
- 2006-03-10 CA CA2601219A patent/CA2601219C/en not_active Expired - Fee Related
- 2006-03-10 CN CNA2006800159308A patent/CN101171213A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4717784A (en) * | 1986-12-10 | 1988-01-05 | Shell Oil Company | Total isomerization process with mono-methyl-branched plus normal paraffin recycle stream |
WO2005049766A1 (fr) * | 2003-11-14 | 2005-06-02 | Institut Francais Du Petrole | Procede de production d'essences a haut indice d'octane a partir d'une coupe c5/c6 utilisant une unite de separation par membrane |
Also Published As
Publication number | Publication date |
---|---|
CA2601219A1 (en) | 2006-09-21 |
KR20070106590A (ko) | 2007-11-01 |
KR100945405B1 (ko) | 2010-03-04 |
CN101171213A (zh) | 2008-04-30 |
WO2006099566A1 (en) | 2006-09-21 |
CA2601219C (en) | 2011-10-25 |
RU2368594C2 (ru) | 2009-09-27 |
RU2007137661A (ru) | 2009-04-20 |
EP1856016A1 (en) | 2007-11-21 |
AU2006222911A1 (en) | 2006-09-21 |
BRPI0608998A2 (pt) | 2010-11-16 |
EP1856016A4 (en) | 2015-01-21 |
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