CH644833A5 - Verfahren zur herstellung von ungesaettigten aethern. - Google Patents

Verfahren zur herstellung von ungesaettigten aethern. Download PDF

Info

Publication number: CH644833A5
Authority: CH; Switzerland
Prior art keywords: acetals; catalyst; formula; cleavage; acetal
Prior art date: 1981-01-15

Application number

CH24481A

Other languages

German (de)

English (en)

Inventor

Sameer H Dr Eldin

Milos Rusek

Original Assignee

Ciba Geigy Ag

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.)

1981-01-15

Filing date

1981-01-15

Publication date

1984-08-31

1981-01-15 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-01-15 Priority to CH24481A priority Critical patent/CH644833A5/de

1982-01-07 Priority to US06/337,898 priority patent/US4396782A/en

1982-01-11 Priority to GB8200655A priority patent/GB2091259B/en

1982-01-12 Priority to DE19823200635 priority patent/DE3200635A1/de

1982-01-13 Priority to CA000394036A priority patent/CA1178975A/en

1982-01-14 Priority to FR8200511A priority patent/FR2497793A1/fr

1982-01-14 Priority to JP57004769A priority patent/JPS57139030A/ja

1984-08-31 Publication of CH644833A5 publication Critical patent/CH644833A5/de

Links

238000000034 method Methods 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title claims description 3
150000002170 ethers Chemical class 0.000 title description 7
150000001241 acetals Chemical class 0.000 claims description 29
239000003054 catalyst Substances 0.000 claims description 21
239000007789 gas Substances 0.000 claims description 8
239000000292 calcium oxide Substances 0.000 claims description 7
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 7
238000003776 cleavage reaction Methods 0.000 claims description 7
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
230000007017 scission Effects 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000002245 particle Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000001577 simple distillation Methods 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
-1 β-unsaturated alkenyl ethers Chemical class 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000012299 nitrogen atmosphere Substances 0.000 claims description 2
238000005798 acetal elimination reaction Methods 0.000 claims 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
239000000463 material Substances 0.000 claims 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 17
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 5
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000012159 carrier gas Substances 0.000 description 3
MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
QBUKAFSEUHGMMX-MTJSOVHGSA-N (5z)-5-[[3-(1-hydroxyethyl)thiophen-2-yl]methylidene]-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1O\C2=C/C=1SC=CC=1C(C)O QBUKAFSEUHGMMX-MTJSOVHGSA-N 0.000 description 1
DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001026509 Kata Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000004946 alkenylalkyl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000003421 catalytic decomposition reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
230000004992 fission Effects 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
101150023545 gel1 gene Proteins 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
238000010327 methods by industry Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 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
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis

Landscapes

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

CH24481A 1981-01-15 1981-01-15 Verfahren zur herstellung von ungesaettigten aethern. CH644833A5 (de)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CH24481A CH644833A5 (de)	1981-01-15	1981-01-15	Verfahren zur herstellung von ungesaettigten aethern.
US06/337,898 US4396782A (en)	1981-01-15	1982-01-07	Process for producing unsaturated ethers
GB8200655A GB2091259B (en)	1981-01-15	1982-01-11	Process for producing unsaturated ethers
DE19823200635 DE3200635A1 (de)	1981-01-15	1982-01-12	"verfahren zur herstellung von ungesaettigten aethern"
CA000394036A CA1178975A (en)	1981-01-15	1982-01-13	Process for producing unsaturated ethers
FR8200511A FR2497793A1 (fr)	1981-01-15	1982-01-14	Procede de preparation d'ethers insatures
JP57004769A JPS57139030A (en)	1981-01-15	1982-01-14	Manufacture of unsaturated ether

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH24481A CH644833A5 (de)	1981-01-15	1981-01-15	Verfahren zur herstellung von ungesaettigten aethern.

Publications (1)

Publication Number	Publication Date
CH644833A5 true CH644833A5 (de)	1984-08-31

Family

ID=4182580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH24481A CH644833A5 (de)	1981-01-15	1981-01-15	Verfahren zur herstellung von ungesaettigten aethern.

Country Status (7)

Country	Link
US (1)	US4396782A (2)
JP (1)	JPS57139030A (2)
CA (1)	CA1178975A (2)
CH (1)	CH644833A5 (2)
DE (1)	DE3200635A1 (2)
FR (1)	FR2497793A1 (2)
GB (1)	GB2091259B (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0217089A1 (de) *	1985-10-02	1987-04-08	Degussa Aktiengesellschaft	Verfahren zur Herstellung ungesättigter Ether durch katalytische Dealkoxylierung von geminalen Di-alkoxy-verbindungen

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4973751A (en) *	1985-03-02	1990-11-27	Basf Aktiengesellschaft	Preparation of unsaturated compounds by elimination reaction
DE3507378A1 (de) *	1985-03-02	1986-09-04	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von ungesaettigten verbindungen durch eliminierungsreaktion
JPH0780801B2 (ja) *	1987-04-03	1995-08-30	日曹丸善ケミカル株式会社	２−クロロエチルビニルエ−テルの精製方法
DE3722891A1 (de) *	1987-07-10	1989-01-19	Basf Ag	Verfahren zur herstellung von vinylethern
DE3726126A1 (de) *	1987-08-06	1989-02-16	Basf Ag	Verfahren zur herstellung von 1.2-dialoxyethenen
DE3804162A1 (de) *	1988-02-11	1989-08-24	Basf Ag	Verfahren zur herstellung von vinylethern
DE4039950A1 (de) *	1990-12-14	1992-06-17	Hoechst Ag	Verfahren zur herstellung von ungesaettigten ethern
RU2144021C1 (ru) *	1998-08-31	2000-01-10	Волгоградское открытое акционерное общество "Химпром"	Способ получения винил-н-бутилового эфира
CN111348991B (zh) *	2018-12-20	2022-08-05	万华化学集团股份有限公司	一种生产乙烯基醚方法
CN118324613B (zh) *	2024-06-13	2024-08-30	安徽华甬新材料股份有限公司	一种2-烷氧基丙烯的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3218359A (en) *		1965-11-16		Preparation of alkoxyalkenes
GB681059A (en)	1949-11-23	1952-10-15	Celanese Corp	Unsaturated ethers
FR1282507A (fr) *	1956-08-13	1962-01-27	Air Reduction	Procédé de fabrication de l'éther trifluoroéthyl-vinylique
US3546300A (en) *	1968-07-05	1970-12-08	Gulf Research Development Co	Conversion of gem-dialkoxy compounds to unsaturated ethers using cacl2
JPS541683B1 (2) *	1970-12-11	1979-01-27
US4014941A (en) *	1970-12-11	1977-03-29	Kyowa Yuka Co., Ltd.	Method of producing α,β-unsaturated ether
JPS4945382A (2) *	1972-09-08	1974-04-30

1981
- 1981-01-15 CH CH24481A patent/CH644833A5/de not_active IP Right Cessation
1982
- 1982-01-07 US US06/337,898 patent/US4396782A/en not_active Expired - Fee Related
- 1982-01-11 GB GB8200655A patent/GB2091259B/en not_active Expired
- 1982-01-12 DE DE19823200635 patent/DE3200635A1/de not_active Withdrawn
- 1982-01-13 CA CA000394036A patent/CA1178975A/en not_active Expired
- 1982-01-14 JP JP57004769A patent/JPS57139030A/ja active Pending
- 1982-01-14 FR FR8200511A patent/FR2497793A1/fr active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0217089A1 (de) *	1985-10-02	1987-04-08	Degussa Aktiengesellschaft	Verfahren zur Herstellung ungesättigter Ether durch katalytische Dealkoxylierung von geminalen Di-alkoxy-verbindungen

Also Published As

Publication number	Publication date
FR2497793B1 (2)	1984-02-24
JPS57139030A (en)	1982-08-27
CA1178975A (en)	1984-12-04
GB2091259A (en)	1982-07-28
US4396782A (en)	1983-08-02
GB2091259B (en)	1984-09-26
FR2497793A1 (fr)	1982-07-16
DE3200635A1 (de)	1982-08-12

Legal Events

Date	Code	Title	Description
1986-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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CH644833A5 - Verfahren zur herstellung von ungesaettigten aethern. - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4182580

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (10)

Family Cites Families (7)

Cited By (1)

Also Published As

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