NO329239B1 - Fremgangsmate for selektiv fremstilling av DIB fra en i-butenholdig C<N>4</N>-strom - Google Patents

Fremgangsmate for selektiv fremstilling av DIB fra en i-butenholdig C<N>4</N>-strom Download PDF

Info

Publication number: NO329239B1
Authority: NO; Norway
Prior art keywords: column; hydroisomerization; butene; carried out; bar
Prior art date: 2000-08-29

Application number

NO20014175A

Other languages

English (en)

Norwegian (no)

Other versions

NO20014175D0 (no

NO20014175L (no

Inventor

Hans-Joachim Kramer

Alexander Gammersbach

Axel Gohrt

Joachim Grub

Stefan Kaminsky

Original Assignee

Bp Koln Gmbh

Priority date (The priority date 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 date listed.)

2000-08-29

Filing date

2001-08-28

Publication date

2010-09-20

2001-08-28 Application filed by Bp Koln Gmbh filed Critical Bp Koln Gmbh

2001-08-28 Publication of NO20014175D0 publication Critical patent/NO20014175D0/no

2002-03-01 Publication of NO20014175L publication Critical patent/NO20014175L/no

2010-09-20 Publication of NO329239B1 publication Critical patent/NO329239B1/no

Links

VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 37
238000000034 method Methods 0.000 title claims description 40
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 44
239000003054 catalyst Substances 0.000 claims abstract description 30
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims abstract description 22
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 18
238000005194 fractionation Methods 0.000 claims abstract description 17
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 13
230000002378 acidificating effect Effects 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 4
238000004821 distillation Methods 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
238000006471 dimerization reaction Methods 0.000 claims description 12
150000002430 hydrocarbons Chemical class 0.000 claims description 11
229930195733 hydrocarbon Natural products 0.000 claims description 10
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 10
229910000510 noble metal Inorganic materials 0.000 claims description 10
239000000463 material Substances 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 4
238000012856 packing Methods 0.000 claims description 4
150000004760 silicates Chemical class 0.000 claims description 4
239000003377 acid catalyst Substances 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
239000012876 carrier material Substances 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
238000004508 fractional distillation Methods 0.000 claims description 3
150000004675 formic acid derivatives Chemical class 0.000 claims description 2
239000000499 gel Substances 0.000 claims description 2
239000002638 heterogeneous catalyst Substances 0.000 claims description 2
239000000377 silicon dioxide Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 2
125000001145 hydrido group Chemical class *[H] 0.000 claims 1
238000006317 isomerization reaction Methods 0.000 claims 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract description 29
235000013844 butane Nutrition 0.000 abstract description 6
239000000047 product Substances 0.000 description 27
239000000203 mixture Substances 0.000 description 7
238000002474 experimental method Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000010779 crude oil Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000006384 oligomerization reaction Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
-1 triisobutene (C12) Chemical compound 0.000 description 2
239000010457 zeolite Substances 0.000 description 2
LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
239000004439 Isononyl alcohol Substances 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
101150101537 Olah gene Proteins 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000446 fuel Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
150000002927 oxygen compounds Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- 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
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/226—Catalytic processes not covered by C07C5/23 - C07C5/31 with metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- 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
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Analytical Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Water Supply & Treatment (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Cephalosporin Compounds (AREA)

NO20014175A 2000-08-29 2001-08-28 Fremgangsmate for selektiv fremstilling av DIB fra en i-butenholdig C<N>4</N>-strom NO329239B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10042280		2000-08-29
DE10103834		2001-01-29

Publications (3)

Publication Number	Publication Date
NO20014175D0 NO20014175D0 (no)	2001-08-28
NO20014175L NO20014175L (no)	2002-03-01
NO329239B1 true NO329239B1 (no)	2010-09-20

Family

ID=26006839

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20014175A NO329239B1 (no)	2000-08-29	2001-08-28	Fremgangsmate for selektiv fremstilling av DIB fra en i-butenholdig C<N>4</N>-strom

Country Status (12)

Country	Link
US (1)	US6632972B2 (de)
EP (1)	EP1184361B1 (de)
JP (1)	JP5142433B2 (de)
KR (1)	KR100776553B1 (de)
AT (1)	ATE267153T1 (de)
AU (1)	AU782627B2 (de)
CA (1)	CA2355445C (de)
DE (1)	DE60103335T2 (de)
ES (1)	ES2219482T3 (de)
MX (1)	MXPA01008737A (de)
NO (1)	NO329239B1 (de)
PT (1)	PT1184361E (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI20021806A0 (fi)	2002-10-10	2002-10-10	Fortum Oyj	Menetelmä bensiiniseoskomponentin valmistamiseksi
CN1926079A (zh)	2003-11-13	2007-03-07	耐思特石油公司	烯烃加氢的方法
US7329788B2 (en) *	2003-12-22	2008-02-12	Neste Oil Oyj	Process for producing gasoline components
US20090099401A1 (en)	2006-06-16	2009-04-16	D Amore Michael B	Process for making isooctenes from aqueous isobutanol
US20080015397A1 (en) *	2006-06-16	2008-01-17	D Amore Michael B	Process for making isooctenes from aqueous 1-butanol
US8975047B2 (en) *	2006-06-16	2015-03-10	E I Du Pont De Nemours And Company	Process for making isooctenes from dry 1-butanol
US20080131948A1 (en) *	2006-12-01	2008-06-05	Leo Ernest Manzer	Process for making isooctenes from dry 2-butanol
US9732018B2 (en) *	2014-02-11	2017-08-15	Saudi Arabian Oil Company	Process for production of mixed butanols and diisobutenes as fuel blending components
JP7090471B2 (ja) *	2018-05-15	2022-06-24	Ｅｎｅｏｓ株式会社	ｐ－キシレンの製造方法
CN114163286B (zh) *	2021-11-29	2024-04-09	万华化学集团股份有限公司	一种异丁烯齐聚加氢生产异构十二烷及联产三异丁烯的方法及装置

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3256351A (en)	1963-08-22	1966-06-14	Monsanto Co	Conversion of o-nitrochlorobenzene to o-dichlorobenzene
EP0008860B2 (de)	1978-07-27	1991-12-04	CHEMICAL RESEARCH & LICENSING COMPANY	Katalysatorsystem
US4242530A (en) *	1978-07-27	1980-12-30	Chemical Research & Licensing Company	Process for separating isobutene from C4 streams
JPS61183231A (ja) *	1985-02-12	1986-08-15	Nippon Zeon Co Ltd	イソアミレンの製造法
CA2043815C (en) *	1990-09-04	1997-04-01	Harvey D. Hensley	Methyl-tertiary ether production
DE19646405A1 (de) *	1996-11-11	1998-05-14	Erdoelchemie Gmbh	Verfahren zur Oligomerisierung von i-Buten
FR2757505B1 (fr) *	1996-12-23	1999-02-19	Inst Francais Du Petrole	Procede de production d'isobutene de haute purete combinant une distillation reactive d'hydroisomerisation, une distillation et une isomerisation squelettale
US5877372A (en) *	1997-11-21	1999-03-02	Arco Chemical Technology, L.P.	Isobutylene oligomerization using isooctane diluent
DE29807007U1 (de)	1998-04-18	1998-07-30	Górak, Andrzej, Prof. Dr.-Ing., 58454 Witten	Packung für Stoffaustauschkolonnen
GB9930402D0 (en) *	1999-12-23	2000-02-16	Exxon Chemical Patents Inc	Selective removal of isobutene from C4 olefinic feedstocks
DK1167326T4 (da) *	2000-06-26	2008-03-17	Saudi Basic Ind Corp	Dimerisering af isobuten

2001
- 2001-08-09 EP EP01306804A patent/EP1184361B1/de not_active Expired - Lifetime
- 2001-08-09 AT AT01306804T patent/ATE267153T1/de active
- 2001-08-09 ES ES01306804T patent/ES2219482T3/es not_active Expired - Lifetime
- 2001-08-09 DE DE60103335T patent/DE60103335T2/de not_active Expired - Lifetime
- 2001-08-09 PT PT01306804T patent/PT1184361E/pt unknown
- 2001-08-16 US US09/930,267 patent/US6632972B2/en not_active Expired - Lifetime
- 2001-08-20 CA CA2355445A patent/CA2355445C/en not_active Expired - Lifetime
- 2001-08-27 AU AU65473/01A patent/AU782627B2/en not_active Ceased
- 2001-08-28 JP JP2001258720A patent/JP5142433B2/ja not_active Expired - Fee Related
- 2001-08-28 NO NO20014175A patent/NO329239B1/no not_active IP Right Cessation
- 2001-08-29 MX MXPA01008737A patent/MXPA01008737A/es active IP Right Grant
- 2001-08-29 KR KR1020010052549A patent/KR100776553B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR100776553B1 (ko)	2007-11-16
AU782627B2 (en)	2005-08-18
AU6547301A (en)	2002-03-07
DE60103335D1 (de)	2004-06-24
DE60103335T2 (de)	2006-03-30
CA2355445C (en)	2010-03-23
EP1184361A1 (de)	2002-03-06
KR20020018118A (ko)	2002-03-07
US20020045786A1 (en)	2002-04-18
JP5142433B2 (ja)	2013-02-13
NO20014175D0 (no)	2001-08-28
US6632972B2 (en)	2003-10-14
CA2355445A1 (en)	2002-02-28
ATE267153T1 (de)	2004-06-15
JP2002087996A (ja)	2002-03-27
ES2219482T3 (es)	2004-12-01
NO20014175L (no)	2002-03-01
EP1184361B1 (de)	2004-05-19
PT1184361E (pt)	2004-09-30
MXPA01008737A (es)	2004-08-11

Legal Events

Date	Code	Title	Description
2014-01-27	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: INEOS SALES (UK) LTD, GB
2021-03-22	MM1K	Lapsed by not paying the annual fees

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CA2749346C (en)	2017-09-12	Process for obtaining high-purity 1-butene from c4 hydrocarbon mixtures
US6054630A (en)	2000-04-25	Apparatus comprising a catalytic distillation zone comprising a reaction zone with distribution of hydrogen
US6468399B2 (en)	2002-10-22	Process for isolating cyclopentane and/or cyclopentene
DE19813720A1 (de)	1999-09-30	Verfahren zur Herstellung von Olefinen
US5969203A (en)	1999-10-19	Process for the production of high purity isobutene combining reactive distillation with hydroisomerization, distillation and skeletal isomerization
RU2139844C1 (ru)	1999-10-20	Способ получения ароматических углеводородов из попутного газа
CA2355445C (en)	2010-03-23	Process for the selective preparation of dib from an i-butene-containing c4 stream
CN1148337C (zh)	2004-05-05	由甲基叔戊基醚制备高含量2－甲基－2－丁烯的异戊烯方法
US6137023A (en)	2000-10-24	Process for the production of high purity isobutene combining reactive distillation with hydroisomerisation and skeletal isomerisation
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US20040192994A1 (en)	2004-09-30	Propylene production
US3761538A (en)	1973-09-25	Butane cracking
US2222128A (en)	1940-11-19	Preparation and separation of aromatic hydrocarbons
KR102298756B1 (ko)	2021-09-03	흡착분리 및 올레핀 전환 공정을 결합한 프로필렌 제조방법
RU2618233C1 (ru)	2017-05-03	Способ получения циклопентана
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US20250368588A1 (en)	2025-12-04	Process for producing high-purity 1-butene and high-purity isobutane
EP0158503B1 (de)	1988-08-10	Verfahren mit hoher Selektivität zur Dehydrierung von paraffinischen Kohlenwasserstoffen
JPS6116792B2 (de)	1986-05-02
BR102025010976A2 (pt)	2026-03-24	Processo para produzir 1-buteno de alta pureza e isobutano de alta pureza, e aparelho para executar o dito processo
CN104250200A (zh)	2014-12-31	一种丁二烯的制备方法
NO170327B (no)	1992-06-29	Fremgangsmaate for direkte forethring av avloepsstroemmen fra en dehydrogeneringssone