GB915037A - A process for the production of ª--carotene - Google Patents
A process for the production of ª--caroteneInfo
- Publication number
- GB915037A GB915037A GB7529/61A GB752961A GB915037A GB 915037 A GB915037 A GB 915037A GB 7529/61 A GB7529/61 A GB 7529/61A GB 752961 A GB752961 A GB 752961A GB 915037 A GB915037 A GB 915037A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carotene
- compound
- produce
- isomerisation
- mols
- 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
- 238000000034 method Methods 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 238000006317 isomerization reaction Methods 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 abstract 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 abstract 1
- 229910017009 AsCl3 Inorganic materials 0.000 abstract 1
- 229910020667 PBr3 Inorganic materials 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- OEYOHULQRFXULB-UHFFFAOYSA-N arsenic trichloride Chemical compound Cl[As](Cl)Cl OEYOHULQRFXULB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The Specification comprises 13,14,131,141-tetrahydr - 11,12;111,121 - bis-dehydro-13,131-dihydroxy-b -carotene having the formula:- <FORM:0915037/IV (b)/1> This compound may be obtained as a light orange-coloured oil having lambdamax 285 mm (e = 44000) by reacting 2 mols of the organometallic compound obtained by dropping 6 - (21,61,61-trimethylcyclohexen-11-yl)-4 methylhexadi-3,5-en-1-yn on to ethyl magnesium bromide with 2 mols of octen-(4)-di-2,7-one at 0 DEG C. This compound may be converted to b -carotene by 2 methods:- (1) Splitting off water by dissolving in an inert solvent such as benzene, toluene, carbon tetrachloride or a petroleum ether; adding an organic base such as pyridine, quinoline, a dialkyl aniline, N-phenyl morpholine or triethylamine and then heating with PCl5, PBr3, POCl3, SOCl2 or AsCl3 to produce the 11,12;111,121-bis-dihydro-b -carotene which is then partially hydrogenated in the presence of a contaminated noble metal catalyst in an organic solvent, if necessary with isomerisation to produce b -carotene. (2) Partially hydrogenating the compound with lithium aluminium hydride in ether to give 13,131-dihydroxy-b -carotene and then splitting off water by refluxing in a nitrogen atmosphere in carbon tetrachloride with N-iodosuccinimide to produce b -carotene, which may be converted to the all-trans form by isomerisation if desired.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30692A DE1114812B (en) | 1960-03-05 | 1960-03-05 | Process for the production of ª-carotene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB915037A true GB915037A (en) | 1963-01-09 |
Family
ID=7093871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7529/61A Expired GB915037A (en) | 1960-03-05 | 1961-03-01 | A process for the production of ª--carotene |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT243998B (en) |
| BE (1) | BE600876A (en) |
| DE (1) | DE1114812B (en) |
| GB (1) | GB915037A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1168890B (en) * | 1961-04-13 | 1964-04-30 | Bayer Ag | Process for the production of lycopene |
-
1960
- 1960-03-05 DE DEF30692A patent/DE1114812B/en active Pending
-
1961
- 1961-03-01 AT AT165861A patent/AT243998B/en active
- 1961-03-01 GB GB7529/61A patent/GB915037A/en not_active Expired
- 1961-03-03 BE BE600876A patent/BE600876A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT243998B (en) | 1965-12-10 |
| DE1114812B (en) | 1961-10-12 |
| BE600876A (en) | 1961-07-03 |
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