GB1021520A - Process for the production and stabilisation of bisketenes - Google Patents
Process for the production and stabilisation of bisketenesInfo
- Publication number
- GB1021520A GB1021520A GB4646362A GB4646362A GB1021520A GB 1021520 A GB1021520 A GB 1021520A GB 4646362 A GB4646362 A GB 4646362A GB 4646362 A GB4646362 A GB 4646362A GB 1021520 A GB1021520 A GB 1021520A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bisketene
- bisketenes
- tertiary
- polar solvent
- solution
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
Abstract
The invention comprises bisketenes, of general formula <FORM:1021520/C2/1> wherein R1 and R3 are alkyl groups, and R2 is a cycloalkyl or aryl group, or wherein R1, R2 and R3, together with the carbons linking them, form part of a cycloalkyl ring. The bisketenes may be prepared by reacting (1) dicarboxylic acid dihalides, of the general formula <FORM:1021520/C2/2> wherein the symbols have the same meaning as above, in solution in a non-polar solvent that is inert to the reactants and the resulting bisketenes (e.g. hexane, ether, chloroform or benzene), with (2) a tertiary nitrogenous organic base, in absence of oxygen and moisture, preferably between - 10 DEG C. and + 50 DEG C. Preferred bases are tertiary aliphatic amines if a solution of bisketene in the free state is required, the base hydrohalide being precipitated out. Replacement of the aliphatic amines by tertiary nitrogenous heterocyclic bases (e.g. pyridine, picoline), gives stable adducts of the bisketene and the base hydrohalide, which precipitate from the non-polar solvent, and these may be stored indefinitely if kept dry. By dissolving this adduct in a suitable inert polar solvent (e.g. dioxane, D.M.F.), the bisketene is returned to a normally reactive state. Alternatively, the said tertiary heterocyclic bases may be reacted with a bisketene solution already prepared by the aforesaid tertiary aliphatic amine process, when adducts of the bisketene and heterocyclic base are precipitated as a hydrohalide-free adduct; this is also stable if kept dry, and may be similarly reformed into an active bisketene solution by dissolving in an inert polar solvent as before. Examples are given for the preparation of (1), (2) and (3) cyclohexane 1,4-bisketene, and its pyridine adduct; and (4) xylylene-bis-a -methyl ketene. The bisketenes are highly reactive, giving diesters or diamides on reaction with alcohols and amides, and reacting with the terminal -OH groups of long chain polyglycols with formation of ester end groups.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC25710A DE1191807B (en) | 1961-12-11 | 1961-12-11 | Process for the production of a stable bisque-adduct |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1021520A true GB1021520A (en) | 1966-03-02 |
Family
ID=7017956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4646362A Expired GB1021520A (en) | 1961-12-11 | 1962-12-10 | Process for the production and stabilisation of bisketenes |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1191807B (en) |
| GB (1) | GB1021520A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010148080A3 (en) * | 2009-06-16 | 2011-09-29 | Draths Corporation | Cyclohexane 1,4 carboxylates |
| US8367858B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Terephthalic and trimellitic based acids and carboxylate derivatives thereof |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| US8426639B2 (en) | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| US8809583B2 (en) | 2010-01-08 | 2014-08-19 | Amyris, Inc. | Methods for producing isomers of muconic acid and muconate salts |
| CN104211613A (en) * | 2013-06-03 | 2014-12-17 | 中国石油化工股份有限公司 | Production method for amide nucleating agent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3002024A (en) * | 1957-03-12 | 1961-09-26 | Goodrich Co B F | Bis-ketenes and method of preparation |
-
1961
- 1961-12-11 DE DEC25710A patent/DE1191807B/en active Pending
-
1962
- 1962-12-10 GB GB4646362A patent/GB1021520A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010148080A3 (en) * | 2009-06-16 | 2011-09-29 | Draths Corporation | Cyclohexane 1,4 carboxylates |
| US8367859B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Cyclohexane 1,4 carboxylates |
| US8367858B2 (en) | 2009-06-16 | 2013-02-05 | Amyris, Inc. | Terephthalic and trimellitic based acids and carboxylate derivatives thereof |
| US8415496B2 (en) | 2009-06-16 | 2013-04-09 | Amyris, Inc. | Biobased polyesters |
| US8426639B2 (en) | 2009-06-16 | 2013-04-23 | Amyris, Inc. | Preparation of trans, trans muconic acid and trans, trans muconates |
| US8809583B2 (en) | 2010-01-08 | 2014-08-19 | Amyris, Inc. | Methods for producing isomers of muconic acid and muconate salts |
| CN104211613A (en) * | 2013-06-03 | 2014-12-17 | 中国石油化工股份有限公司 | Production method for amide nucleating agent |
| CN104211613B (en) * | 2013-06-03 | 2016-09-21 | 中国石油化工股份有限公司 | A kind of production method of acid amide type nucleator |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1191807B (en) | 1965-04-29 |
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