GB826621A - Separation of grignard reagents from cyclic ethers - Google Patents
Separation of grignard reagents from cyclic ethersInfo
- Publication number
- GB826621A GB826621A GB28688/57A GB2868857A GB826621A GB 826621 A GB826621 A GB 826621A GB 28688/57 A GB28688/57 A GB 28688/57A GB 2868857 A GB2868857 A GB 2868857A GB 826621 A GB826621 A GB 826621A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- group
- tetrahydrofuran
- ether
- diethylene glycol
- 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.)
- Expired
Links
- 150000004292 cyclic ethers Chemical class 0.000 title abstract 3
- 238000000926 separation method Methods 0.000 title abstract 2
- 150000004795 grignard reagents Chemical class 0.000 title 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 229920000570 polyether Polymers 0.000 abstract 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 abstract 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 abstract 2
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- -1 organomagnesium chlorides Chemical class 0.000 abstract 2
- 125000002734 organomagnesium group Chemical group 0.000 abstract 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 abstract 2
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 abstract 1
- BTHLKLUTMYTDFM-UHFFFAOYSA-N 2-ethoxyoxane Chemical compound CCOC1CCCCO1 BTHLKLUTMYTDFM-UHFFFAOYSA-N 0.000 abstract 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- PPHBKSRTKMLMMO-UHFFFAOYSA-M [Cl-].[Mg+]C=C.C1CCOC1 Chemical compound [Cl-].[Mg+]C=C.C1CCOC1 PPHBKSRTKMLMMO-UHFFFAOYSA-M 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 1
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000001282 organosilanes Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
Complexes of organomagnesium chlorides with cyclic ethers such as are described in Specifications 776,993, 777,158 and 779,100 are separated into their components by treatment with an ethylene polyether of formula R3O (CH2CH2O)xR4, wherein x is an integer from 1 to 8, R3 and R4 are the same or different and represent substituted or unsubstituted hydrocarbon groups, the permissible substituents being groups which do not react with the reactants or reaction products under the conditions of the separation procedure. The organo-magnesium chloride is of formula R2(MgCl)y wherein y is a small whole number and R2 is a substituted or unsubstituted alkyl, alkenyl, aryl, aralkyl, aralkenyl or heterocyclic radical, and when y is greater than 1, R2 is the corresponding polyvalent radical whose valency is equal to y. It may be complexed with tetrahydrofuran, tetrahydropyran, 2-methyltetrahydrofuran, 2 - ethoxytetrahydropyran, tetrahydrofurfuryl ethyl ether, dihydropyran and Nmethyl morpholine. The groups R3 and R4 in the cyclic ether are preferably C2-C5 aliphatic hydrocarbon radicals; phenyl groups or substituted phenyl groups having not more than 5 atoms in each substituting group (and not more than 3 substituting groups), or aralkyl groups which have no more than 4 carbon atoms in the alkyl group, the aryl being phenyl. Specified polyethers are diethylene glycol diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether and tetraethylene glycol dimethyl ether. In an example diethylene glycol diethyl ether is added to a solution of a complex of vinyl magnesium chloride-tetrahydrofuran in tetrahydrofuran. The tetrahydrofuran is distilled off under reduced pressure. The resulting solution may be used for the synthesis of other compounds such as, for instance, trimethyl vinyl silane (see Group IV (a)). Specifications 802,517 and 826,620 also are referred to.ALSO:Organosilanes are prepared by reacting a halosilicon compound with an organomagnesium chloride in solution in an ethylene polyether of formula R3O(CH2CH2O)xR4 wherein x is 1-8, and R3 and R4 are the same or different and represent substituted or unsubstituted hydrocarbon groups. In Example 1, vinyl magnesium chloride in diethylene glycol ether (which has displaced the tetrahydrofuran used in the preparation of the complex) is reacted with trimethylchlorosilane to give trimethylvinylsilane. Specifications 776,993, [Group IV (b)], 777,158, [Group II], 779,100, [Group IV (b)], 802,517 and 826,620 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US826621XA | 1956-09-18 | 1956-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB826621A true GB826621A (en) | 1960-01-13 |
Family
ID=22172590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28688/57A Expired GB826621A (en) | 1956-09-18 | 1957-09-11 | Separation of grignard reagents from cyclic ethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB826621A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005301A1 (en) * | 1978-05-10 | 1979-11-14 | Metallgesellschaft Ag | Process for the removal of sulphur oxides from high-chloride flue gases |
-
1957
- 1957-09-11 GB GB28688/57A patent/GB826621A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005301A1 (en) * | 1978-05-10 | 1979-11-14 | Metallgesellschaft Ag | Process for the removal of sulphur oxides from high-chloride flue gases |
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