NO872191L - Fremgangsmaate for fremstilling av etere ved anvendelse av lagdelte eller soeyleformige leirekatalysatorer. - Google Patents

Fremgangsmaate for fremstilling av etere ved anvendelse av lagdelte eller soeyleformige leirekatalysatorer.

Info

Publication number: NO872191L
Authority: NO; Norway
Prior art keywords: methanol; layered; isobutene; molar ratio; clay
Prior art date: 1986-05-29

Application number

NO872191A

Other languages

English (en)

Norwegian (no)

Other versions

NO872191D0 (no

Inventor

Martin Philip Atkins

Ian Michael Wren

Original Assignee

British Petroleum Co Plc

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.)

1986-05-29

Filing date

1987-05-26

Publication date

1987-11-30

1987-05-26 Application filed by British Petroleum Co Plc filed Critical British Petroleum Co Plc

1987-05-26 Publication of NO872191D0 publication Critical patent/NO872191D0/no

1987-11-30 Publication of NO872191L publication Critical patent/NO872191L/no

Links

239000003054 catalyst Substances 0.000 title claims abstract description 28
238000000034 method Methods 0.000 title claims description 22
150000002170 ethers Chemical class 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title description 3
150000001336 alkenes Chemical class 0.000 claims abstract description 31
239000004927 clay Substances 0.000 claims abstract description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
230000002378 acidificating effect Effects 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
150000001298 alcohols Chemical class 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 76
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 33
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 25
238000004519 manufacturing process Methods 0.000 claims description 20
229910052901 montmorillonite Inorganic materials 0.000 claims description 19
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical group O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 18
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 10
229910021647 smectite Inorganic materials 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
150000005673 monoalkenes Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 claims description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
BRSDPVLOTZLFFV-UHFFFAOYSA-N methanol;2-methylprop-1-ene Chemical compound OC.CC(C)=C BRSDPVLOTZLFFV-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 12
230000000694 effects Effects 0.000 description 11
239000000203 mixture Substances 0.000 description 11
229920005989 resin Polymers 0.000 description 8
239000011347 resin Substances 0.000 description 8
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
239000010410 layer Substances 0.000 description 7
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
238000006884 silylation reaction Methods 0.000 description 6
238000006384 oligomerization reaction Methods 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000539 dimer Substances 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
-1 hydrogen ions Chemical class 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
235000012216 bentonite Nutrition 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
238000003780 insertion Methods 0.000 description 2
230000037431 insertion Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910000273 nontronite Inorganic materials 0.000 description 2
229920005990 polystyrene resin Polymers 0.000 description 2
239000011148 porous material Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
235000019354 vermiculite Nutrition 0.000 description 2
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
229940037003 alum Drugs 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
239000011229 interlayer Substances 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000006053 organic reaction 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
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical class CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
150000003754 zirconium Chemical class 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO872191A 1986-05-29 1987-05-26 Fremgangsmaate for fremstilling av etere ved anvendelse av lagdelte eller soeyleformige leirekatalysatorer. NO872191L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868613080A GB8613080D0 (en)	1986-05-29	1986-05-29	Production of ethers

Publications (2)

Publication Number	Publication Date
NO872191D0 NO872191D0 (no)	1987-05-26
NO872191L true NO872191L (no)	1987-11-30

Family

ID=10598634

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO872191A NO872191L (no)	1986-05-29	1987-05-26	Fremgangsmaate for fremstilling av etere ved anvendelse av lagdelte eller soeyleformige leirekatalysatorer.

Country Status (5)

Country	Link
EP (1)	EP0249352A1 (fr)
JP (1)	JPS6366139A (fr)
AU (1)	AU7340287A (fr)
GB (1)	GB8613080D0 (fr)
NO (1)	NO872191L (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5003112A (en) *	1990-01-02	1991-03-26	Texaco Chemical Company	Tertiary amyl methyl ether from C-5 olefin streams
US5308812A (en) *	1993-04-01	1994-05-03	Bp America, Inc.	Treated pillared clays and alkylation process using same
GB9501143D0 (en) *	1995-01-20	1995-03-08	British Petroleum Co	Etherification process

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU6579481A (en) *	1979-12-22	1981-07-22	British Petroleum Co	Proton-catalysed reactions catalysed by hydrogen ion- exchanged layered clays
US4542250A (en) *	1982-01-09	1985-09-17	The British Petroleum Company, P.L.C.	Use of stabilized pillared interlayered clays as catalyst in alkylation reactions
GB8400271D0 (en) *	1984-01-06	1984-02-08	British Petroleum Co Plc	Treatment of layered clay

1986
- 1986-05-29 GB GB868613080A patent/GB8613080D0/en active Pending
1987
- 1987-05-21 EP EP87304547A patent/EP0249352A1/fr not_active Withdrawn
- 1987-05-26 NO NO872191A patent/NO872191L/no unknown
- 1987-05-26 AU AU73402/87A patent/AU7340287A/en not_active Abandoned
- 1987-05-29 JP JP62134802A patent/JPS6366139A/ja active Pending

Also Published As

Publication number	Publication date
AU7340287A (en)	1987-12-03
EP0249352A1 (fr)	1987-12-16
JPS6366139A (ja)	1988-03-24
NO872191D0 (no)	1987-05-26
GB8613080D0 (en)	1986-07-02

Publication	Publication Date	Title
US9260355B2 (en)	2016-02-16	Production of propylene via simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts followed by metathesis
US5082990A (en)	1992-01-21	Alkylation of aromatics-containing refinery streams
US7196238B2 (en)	2007-03-27	Process for dimerizing light olefins
KR101343652B1 (ko)	2013-12-23	1-부텐, 2-부텐 및 이소부텐을 포함하는 공업용 ｃ4 탄화수소 스트림으로부터 말단 이중 결합의 함량이 50% 초과인 폴리이소부틸렌을 제조하는 방법
US8247631B2 (en)	2012-08-21	Process for catalytic cracking of hydrocarbons using UZM-35
US20130204057A1 (en)	2013-08-08	Simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts
US6005150A (en)	1999-12-21	Process for the production of butene-1 from a mixture of C4 olefins
EP2374780A1 (fr)	2011-10-12	Préparation de propylene via déshydratation et isomérisation simultane du squelette carboné de l'isobutanol sur des catalyseurs acides suivi par une métathèse
US4324938A (en)	1982-04-13	Process for upgrading C4 olefinic cuts
NO860523L (no)	1986-08-18	Fremgangsmaate for fremstilling av olefiner.
US20130261345A1 (en)	2013-10-03	Production of fuel additives via simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts followed by etherification
US9637422B2 (en)	2017-05-02	Method for preparing high purity isobutene using glycolether
US6156947A (en)	2000-12-05	Process for the production of butene-1 from a mixture of C4 olefins
US4357147A (en)	1982-11-02	Diisopropyl ether reversion and oligomerization in isopropanol production
US4675460A (en)	1987-06-23	Process
CA2314799C (fr)	2009-03-17	Procede pour la production d'hydrocarbures ayant un indice d'octane eleve par dimerisation selective de l'isobutene
US4352945A (en)	1982-10-05	Diisopropyl ether reversion in isopropanol production
US4405822A (en)	1983-09-20	Diisopropyl ether hydration in isopropanol production
JPH08501076A (ja)	1996-02-06	オレフィンの製造方法
US5227569A (en)	1993-07-13	Skeletal isomerization of n-butylenes to isobutylene on boron-beta zeolites
NO872191L (no)	1987-11-30	Fremgangsmaate for fremstilling av etere ved anvendelse av lagdelte eller soeyleformige leirekatalysatorer.
JPH05246919A (ja)	1993-09-24	ゼオライト触媒を用いるアルキル第三級アルキルエーテルの合成方法
JPS60222428A (ja)	1985-11-07	炭化水素の接触転化法
WO1986003484A1 (fr)	1986-06-19	Procede de preparation d'ethers
CA1212700A (fr)	1986-10-14	Production de carburant diesel