GB933457A - A process for the production of cyclopropane hydrocarbons - Google Patents
A process for the production of cyclopropane hydrocarbonsInfo
- Publication number
- GB933457A GB933457A GB12680/61A GB1268061A GB933457A GB 933457 A GB933457 A GB 933457A GB 12680/61 A GB12680/61 A GB 12680/61A GB 1268061 A GB1268061 A GB 1268061A GB 933457 A GB933457 A GB 933457A
- Authority
- GB
- United Kingdom
- Prior art keywords
- boron
- cyclopropane
- reaction
- hydrocarbons
- hydrogen
- 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
- -1 cyclopropane hydrocarbons Chemical class 0.000 title abstract 5
- 229930195733 hydrocarbon Natural products 0.000 title abstract 5
- 229910052796 boron Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001639 boron compounds Chemical class 0.000 abstract 2
- 229910010277 boron hydride Inorganic materials 0.000 abstract 2
- 239000008139 complexing agent Substances 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- SAHWBARCQUAFSM-PHDIDXHHSA-N (1r,2r)-1-ethyl-2-methylcyclopropane Chemical compound CC[C@@H]1C[C@H]1C SAHWBARCQUAFSM-PHDIDXHHSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 1
- 150000005218 dimethyl ethers Chemical class 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- MWVPQZRIWVPJCA-UHFFFAOYSA-N propylcyclopropane Chemical compound CCCC1CC1 MWVPQZRIWVPJCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/062—Al linked exclusively to C
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Cyclopropane hydrocarbons are obtained from a 3-halogenoalkyl boron in the presence of an alkali or alkaline earth metal hydride or alkyl or complex thereof with a compound of a Group III element (Me) of the formula Me Y3 in which Y is hydrogen, hydrocarbon, alkoxy or aryloxy, the reaction being effected in the absence of air or oxygen, the reaction forms as by-products, boron hydride, boron hydrocarbons or diboranes or, in the presence of tertiary amines, N-trisubstituted borazanes. The boron compound contains the functional group -CR2-CR2-CR2X attached to boron, the other two boron valencies being satisfied by like or unlike groups including hydrogen and cyclic groups, where X is chlorine, bromine or iodine and each R is like or unlike being hydrogen or hydrocarbon which may be interconnected, and is formed by the reaction of the corresponding allyl halide or substituted allyl halide on boron hydride or the diborane obtained in the cyclopropane-forming reaction. Suitable solvents are paraffinic and aromatic hydrocarbons, dimethyl ethers of di- and triethylene glycol, tetrahydrofuran and, when a boron compound is used as the complexing agent MeY3, excess of this complexing agent. The examples describe the preparations of (1) methyl cyclopropane, (3) n-propylcyclopropane, (4) cis- and trans-1-methyl-2-ethyl-cyclopropane (1:1 molar ratio), (5) cyclopropane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEST16347A DE1110636B (en) | 1960-04-11 | 1960-04-11 | Process for the production of cyclopropane hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB933457A true GB933457A (en) | 1963-08-08 |
Family
ID=7457033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12680/61A Expired GB933457A (en) | 1960-04-11 | 1961-04-07 | A process for the production of cyclopropane hydrocarbons |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH415605A (en) |
| DE (1) | DE1110636B (en) |
| GB (1) | GB933457A (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB498225A (en) * | 1936-06-13 | 1939-01-02 | Purdue Research Foundation | Process of producing cycloproprane |
| US2211787A (en) * | 1937-04-30 | 1940-08-20 | Squibb & Sons Inc | Preparation of cyclopropane |
| US2279721A (en) * | 1938-03-12 | 1942-04-14 | Winthrop Chem Co Inc | Process of preparing cycloalkanes |
| US2496419A (en) * | 1949-06-03 | 1950-02-07 | Dow Corning | Production of cyclopropane |
-
1960
- 1960-04-11 DE DEST16347A patent/DE1110636B/en active Pending
-
1961
- 1961-04-07 GB GB12680/61A patent/GB933457A/en not_active Expired
- 1961-04-07 CH CH408661A patent/CH415605A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH415605A (en) | 1966-06-30 |
| DE1110636B (en) | 1961-07-13 |
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