GB751573A - A polyene dialdehyde and process for the manufacture thereof - Google Patents
A polyene dialdehyde and process for the manufacture thereofInfo
- Publication number
- GB751573A GB751573A GB23436/54A GB2343654A GB751573A GB 751573 A GB751573 A GB 751573A GB 23436/54 A GB23436/54 A GB 23436/54A GB 2343654 A GB2343654 A GB 2343654A GB 751573 A GB751573 A GB 751573A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ine
- dial
- dimethyl
- acid
- tetramethyl
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention comprises 2,6,11,15-tetramethyl - hexadecahexen - (2,4,6,10,12,14) - ine-(8) - dial - (1,16) and a process for its preparation by acetalizing 4,9-dimethyl-dodecatetraen-(2,4,8,10) - ine - (6) - dial - (1,12), condensing the diacetal so obtained with a propenyl ether in the presence of an acidic condensing agent and treating the resulting 3,14-dietherified 2,6,11,15 - tetramethyl - hexadecatetraen-(4,6,10,12) - ine - (8) - diacetal - (1,16) with an acid agent to effect hydrolysis of the acetal groups and elimination of alcohol from between positions 2 and 3, and 14 and 15. Specified acid condensing agents are boron trifluoride-ether complex, zinc chloride, aluminium chloride, and the tetrachlorides of titanium and tin, whilst the acid agent used for the hydrolysis of the acetal groups is a water-soluble non-volatile organic or inorganic acid, e.g. p-toluene sulphonic, acetic, propionic, sulphuric or phosphoric acids, or a water-soluble salt having an acid reaction, e.g. zinc chloride or sodium hydrogen sulphate. In an example 4,9-dimethyl-dodecatetraen - (2,4,8,10) - ine - (6) - dial (1,12) in ethyl orthoformate is heated with ethanolic ammonium nitrate to yield the corresponding di(diethyl acetal)-(1,12), which is treated with ethyl propenyl ether and boron trifluoride-ether complex to produce 3,14-diethoxy-2,6,11, 15 - tetramethyl - hexadecatetraen - (4,6,10,12)-ine - (8) - di(diethyl acetal) - (1,16). Hydrolysis with phosphoric acid in aqueous dioxan containing a trace of hydroquinone yields 2,6,11,15 - tetramethyl - hexadecahexen-(2,4,6,10,12,14)-ine-(8)-dial-(1,16). The Specification also refers to the formation of dehydro-methyl bixin, dehydro-crocetin and dehydro-bixin dialdehyde from the novel compound of the invention. 4,9 - Dimethyl - dodecatetraen - (2,4,8,10) - ine-(6) - dial - (1,12) is prepared by acetalizing 2,7 - dimethyl - octadien - (2,6) - ine - (4) - dial-(1,8) with ethyl-ortho-formate in the presence of ammonium nitrate, condensing the product with ethyl vinyl ether and hydrolysing the 3,10-dietherified - 4,9 - dimethyl - dodecadien - (4,8)-ine - (6) - diacetal - (1,12) with aqueous phosphoric acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH751573X | 1953-08-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB751573A true GB751573A (en) | 1956-06-27 |
Family
ID=4533929
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23436/54A Expired GB751573A (en) | 1953-08-14 | 1954-08-12 | A polyene dialdehyde and process for the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB751573A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3103352A1 (en) | 2015-06-12 | 2016-12-14 | DSM IP Assets B.V. | Acid stable beverages comprising bixin |
WO2016198569A1 (en) | 2015-06-12 | 2016-12-15 | Dsm Ip Assets B.V. | New orange color for edible coatings |
WO2016198570A1 (en) | 2015-06-12 | 2016-12-15 | Dsm Ip Assets B.V. | New natural color for edible coatings |
-
1954
- 1954-08-12 GB GB23436/54A patent/GB751573A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3103352A1 (en) | 2015-06-12 | 2016-12-14 | DSM IP Assets B.V. | Acid stable beverages comprising bixin |
WO2016198569A1 (en) | 2015-06-12 | 2016-12-15 | Dsm Ip Assets B.V. | New orange color for edible coatings |
WO2016198567A1 (en) | 2015-06-12 | 2016-12-15 | Dsm Ip Assets B.V. | Acid stable beverages comprising bixin |
WO2016198570A1 (en) | 2015-06-12 | 2016-12-15 | Dsm Ip Assets B.V. | New natural color for edible coatings |
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