GB790450A - Process for the production of sodium substitution products of cyclopentadiene and its alkylated and benzylated derivatives - Google Patents
Process for the production of sodium substitution products of cyclopentadiene and its alkylated and benzylated derivativesInfo
- Publication number
- GB790450A GB790450A GB411356A GB411356A GB790450A GB 790450 A GB790450 A GB 790450A GB 411356 A GB411356 A GB 411356A GB 411356 A GB411356 A GB 411356A GB 790450 A GB790450 A GB 790450A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclopentadiene
- sodium
- tertiary
- alkylated
- production
- 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title abstract 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 title abstract 3
- 229910052708 sodium Inorganic materials 0.000 title abstract 3
- 239000011734 sodium Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 238000006467 substitution reaction Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- NUUNDIOOYFEMQN-UHFFFAOYSA-N cyclopenta-1,3-diene;sodium Chemical compound [Na].C1C=CC=C1 NUUNDIOOYFEMQN-UHFFFAOYSA-N 0.000 abstract 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 2
- -1 2-ethyl Chemical class 0.000 abstract 1
- XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- YOTNIZSDGKKMGR-UHFFFAOYSA-N cyclopenta-1,3-dien-1-ylmethylbenzene Chemical compound C=1C=CC=CC=1CC1=CC=CC1 YOTNIZSDGKKMGR-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical group [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003509 tertiary alcohols Chemical class 0.000 abstract 1
- 239000008096 xylene 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The process of the parent Specification is modified by reacting cyclopentadiene, an alkyl or benzyl cyclopentadiene with a tertiary sodium alcoholate at a temperature up to 250 DEG C. Tertiary sodium butylate, and the sodium derivatives of 2-ethyl hexanol-2 and triethyl carbinol are specified. The alcoholate may be used in stoichiometric amounts, in excess or if desired a minor proportion of the tertiary alcohol may be added to a sodium-cyclopentadiene mixture. Inert solvents (absolute ether, decahydronaphthalene, xylene) are specified in the examples. In Example (1) finely divided sodium is suspended in absolute ether, tertiary butyl alcohol added and cyclopentadiene added dropwise under a nitrogen atmosphere. Sodium cyclopentadiene is precipitated.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ2636A DE924029C (en) | 1952-04-22 | 1952-04-22 | Process for the preparation of sodium cyclopentadiene, sodium alkyl and sodium benzyl cyclopentadienes |
| DEZ4713A DE1000379B (en) | 1952-04-22 | 1955-02-10 | Process for the preparation of sodium cyclopentadiene, sodium alkyl and sodium benzyl cyclopentadienes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB790450A true GB790450A (en) | 1958-02-12 |
Family
ID=26003312
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1094753A Expired GB763825A (en) | 1952-04-22 | 1953-04-21 | Substitution products of cyclopentadiene and its alkyl and benzyl derivatives and the production thereof |
| GB411356A Expired GB790450A (en) | 1952-04-22 | 1956-02-09 | Process for the production of sodium substitution products of cyclopentadiene and its alkylated and benzylated derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1094753A Expired GB763825A (en) | 1952-04-22 | 1953-04-21 | Substitution products of cyclopentadiene and its alkyl and benzyl derivatives and the production thereof |
Country Status (3)
| Country | Link |
|---|---|
| DE (3) | DE924029C (en) |
| FR (2) | FR1078707A (en) |
| GB (2) | GB763825A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835712A (en) * | 1955-07-11 | 1958-05-20 | Ziegler | Process for the production of calcium compounds of cyclopentadiene and its alkylated, aralkylated, and arylated derivatives |
| DE1099537B (en) * | 1957-07-16 | 1961-02-16 | Heinrich Gold Dipl Chem Dr Rer | Process for the direct production of organic anhydrous, solid or dissolved alkali or alkaline earth metal salts or of salt-like compounds of these metals |
| US2942040A (en) * | 1957-09-18 | 1960-06-21 | Ethyl Corp | Manufacture of sodium cyclopentadiene from cyclopentadiene dimer |
| US2985692A (en) * | 1959-01-27 | 1961-05-23 | Ethyl Corp | Manufacture of alkyl magnesium compounds |
| US2987558A (en) * | 1959-11-13 | 1961-06-06 | Ethyl Corp | Organometal compounds |
-
1952
- 1952-04-22 DE DEZ2636A patent/DE924029C/en not_active Expired
- 1952-08-06 DE DEZ2857A patent/DE927873C/en not_active Expired
-
1953
- 1953-04-21 GB GB1094753A patent/GB763825A/en not_active Expired
- 1953-04-21 FR FR1078707D patent/FR1078707A/en not_active Expired
-
1955
- 1955-02-10 DE DEZ4713A patent/DE1000379B/en active Pending
-
1956
- 1956-02-03 FR FR69262D patent/FR69262E/en not_active Expired
- 1956-02-09 GB GB411356A patent/GB790450A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1078707A (en) | 1954-11-23 |
| FR69262E (en) | 1958-10-23 |
| DE1000379B (en) | 1957-01-10 |
| GB763825A (en) | 1956-12-19 |
| DE924029C (en) | 1955-02-24 |
| DE927873C (en) | 1955-05-20 |
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