NL8103847A - Werkwijze voor het bereiden van vertakte alifatische ethers voor verhoging van het octaangetal, door gebruik van vaste superzure katalysatoren. - Google Patents

Werkwijze voor het bereiden van vertakte alifatische ethers voor verhoging van het octaangetal, door gebruik van vaste superzure katalysatoren. Download PDF

Info

Publication number: NL8103847A
Authority: NL; Netherlands
Prior art keywords: olefin; alcohol; solid; catalyst; aliphatic ethers
Prior art date: 1980-08-18

Application number

NL8103847A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ugine Kuhlmann

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.)

1980-08-18

Filing date

1981-08-17

Publication date

1982-03-16

1981-08-17 Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann

1982-03-16 Publication of NL8103847A publication Critical patent/NL8103847A/nl

Links

239000003054 catalyst Substances 0.000 title claims abstract description 21
239000003930 superacid Substances 0.000 title claims description 12
150000002170 ethers Chemical class 0.000 title description 11
238000004519 manufacturing process Methods 0.000 title description 3
150000001336 alkenes Chemical class 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
-1 aliphatic ethers Chemical class 0.000 claims abstract description 12
239000007787 solid Substances 0.000 claims abstract description 11
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
229920000642 polymer Polymers 0.000 claims description 8
125000000542 sulfonic acid group Chemical group 0.000 claims description 3
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
238000006243 chemical reaction Methods 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 13
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
239000000654 additive Substances 0.000 description 8
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 7
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
LYCAGOQDEOWYGS-UHFFFAOYSA-N 1,2,2-trifluoroethenesulfonic acid Chemical compound OS(=O)(=O)C(F)=C(F)F LYCAGOQDEOWYGS-UHFFFAOYSA-N 0.000 description 4
229920000557 Nafion® Polymers 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000000996 additive effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
HNFSPSWQNZVCTB-UHFFFAOYSA-N 2-methyl-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)(C)C HNFSPSWQNZVCTB-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000446 fuel Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
238000011282 treatment Methods 0.000 description 2
HYWZIAVPBSTISZ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-henicosafluorodecane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HYWZIAVPBSTISZ-UHFFFAOYSA-N 0.000 description 1
CFCRODHVHXGTPC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-pentacosafluorododecane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CFCRODHVHXGTPC-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
238000006959 Williamson synthesis reaction Methods 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
231100000315 carcinogenic Toxicity 0.000 description 1
238000010411 cooking Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
SHWHUCFJRAMLQS-UHFFFAOYSA-N sulfuryl difluoride;1,1,2-trifluoroethene Chemical compound FC=C(F)F.FS(F)(=O)=O SHWHUCFJRAMLQS-UHFFFAOYSA-N 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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
- 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
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups

Landscapes

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

NL8103847A 1980-08-18 1981-08-17 Werkwijze voor het bereiden van vertakte alifatische ethers voor verhoging van het octaangetal, door gebruik van vaste superzure katalysatoren. NL8103847A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US17889080A	1980-08-18	1980-08-18
US17889080		1980-08-18

Publications (1)

Publication Number	Publication Date
NL8103847A true NL8103847A (nl)	1982-03-16

Family

ID=22654326

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8103847A NL8103847A (nl)	1980-08-18	1981-08-17	Werkwijze voor het bereiden van vertakte alifatische ethers voor verhoging van het octaangetal, door gebruik van vaste superzure katalysatoren.

Country Status (8)

Country	Link
JP (1)	JPS5759825A (it)
BE (1)	BE889942A (it)
CA (1)	CA1179379A (it)
DE (1)	DE3131974A1 (it)
FR (1)	FR2488601A1 (it)
GB (1)	GB2082177B (it)
IT (1)	IT1137629B (it)
NL (1)	NL8103847A (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62101716U (it) *	1985-12-16	1987-06-29
US5157162A (en) *	1991-10-25	1992-10-20	Texaco Chemical Company	One step synthesis of methyl t-butyl ether from t-butanol using fluorosulfonic acid-modified clay catalysts
JPWO2004094357A1 (ja) *	2003-04-23	2006-07-13	株式会社ジャパンエナジー	固体酸触媒を用いたエーテルの製造方法
AT505758B1 (de) *	2008-02-13	2009-04-15	Hinterecker Ges M B H	Verfahren zur herstellung von biodieselkraftstoff

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1249016A (en) *	1969-10-02	1971-10-06	Chevron Res	Process for production of gasoline
JPS5346811B2 (it) *	1971-08-26	1978-12-16
US4139566A (en) *	1977-10-03	1979-02-13	Shell Oil Company	Secondary alcohol ethoxylate process
US4282386A (en) *	1980-05-02	1981-08-04	The Dow Chemical Company	Alkyl, cycloalkyl diethers of (poly)alkylene glycols
JPS56154423A (en) *	1980-05-02	1981-11-30	Toyo Soda Mfg Co Ltd	Production of methyl t-butyl ether

1981
- 1981-07-28 IT IT23204/81A patent/IT1137629B/it active
- 1981-08-11 GB GB8124553A patent/GB2082177B/en not_active Expired
- 1981-08-12 BE BE0/205651A patent/BE889942A/fr not_active IP Right Cessation
- 1981-08-13 DE DE19813131974 patent/DE3131974A1/de not_active Withdrawn
- 1981-08-14 FR FR8115747A patent/FR2488601A1/fr active Granted
- 1981-08-17 NL NL8103847A patent/NL8103847A/nl not_active Application Discontinuation
- 1981-08-17 JP JP56127757A patent/JPS5759825A/ja active Pending
- 1981-08-17 CA CA000384026A patent/CA1179379A/fr not_active Expired

Also Published As

Publication number	Publication date
IT1137629B (it)	1986-09-10
GB2082177A (en)	1982-03-03
CA1179379A (fr)	1984-12-11
FR2488601A1 (fr)	1982-02-19
BE889942A (fr)	1982-02-12
FR2488601B1 (it)	1984-11-30
DE3131974A1 (de)	1982-04-01
GB2082177B (en)	1984-07-25
IT8123204A0 (it)	1981-07-28
JPS5759825A (en)	1982-04-10

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-04-05	BV	The patent application has lapsed

Publication	Publication Date	Title
JPS6027658B2 (ja)	1985-06-29	ジアルキルカーボネートの製造法
CS232749B2 (en)	1985-02-14	Method of methyl tertiary butylether production
EP0981509A1 (en)	2000-03-01	Superacid catalyzed formylation-rearrangement of saturated hydrocarbons
EP2905293A1 (en)	2015-08-12	Process for catalytic synthesis of low-carbon polyether-based compound by using acidic ionic liquid
CA2299587A1 (en)	2000-08-26	Process for producing vinyl esters from butene oligomers
NL8103847A (nl)	1982-03-16	Werkwijze voor het bereiden van vertakte alifatische ethers voor verhoging van het octaangetal, door gebruik van vaste superzure katalysatoren.
NO872978D0 (no)	1987-07-16	Forbedret fremgangsmaate for omvandling av metanol til alkyletere.
Shi et al.	2003	The first non-acid catalytic synthesis of tert-butyl ether from tert-butyl alcohol using ionic liquid as dehydrator
SU734182A1 (ru)	1980-05-15	Способ получени вторичного бутилового спирта
US4424388A (en)	1984-01-03	Production of alcohols by hydration of olefins
US4503263A (en)	1985-03-05	Process for the preparation of octane boosting branched aliphatic ethers using solid superacid catalysts
FR2471965A1 (fr)	1981-06-26	Procede de preparation de carboxylates d'alkyles a partir de leurs homologues inferieurs
NO157294B (no)	1987-11-16	Fremgangsm te til kontinuerlig fremstilling av alko
US2449471A (en)	1948-09-14	Preparation of ether esters
JPS6034926B2 (ja)	1985-08-12	グライコ−ルジアルキルエ−テルの変換方法
US5994578A (en)	1999-11-30	Ester preparation
FR2464241A1 (fr)	1981-03-06	Procede de production d'alcool butylique tertiaire
US4029710A (en)	1977-06-14	4-Alkoxy-N-butyraldehyde preparation
JP2612194B2 (ja)	1997-05-21	線状オレフインの直接水加法
US5349110A (en)	1994-09-20	Synthesis of low molecular weight glycol ethers from oxiranes plus olefins
GB2238539A (en)	1991-06-05	Preparation of alcohols from olefins
NL8103846A (nl)	1982-03-16	Werkwijze voor het hydrateren van propeen tot isopropylalcohol over vaste superzure geperfluoreerde sulfonzuurkatalysatoren.
JP3995750B2 (ja)	2007-10-24	エーテル化合物の製造方法
US2749360A (en)	1956-06-05	Esters of alpha-2, 4, 5-trichlorophenoxypropionic acid
RU2057111C1 (ru)	1996-03-27	Способ получения c4- c5-алкиловых эфиров