GB819897A - Process for the production of unsaturated compounds of the vitamin a series - Google Patents
Process for the production of unsaturated compounds of the vitamin a seriesInfo
- Publication number
- GB819897A GB819897A GB17382/58A GB1738258A GB819897A GB 819897 A GB819897 A GB 819897A GB 17382/58 A GB17382/58 A GB 17382/58A GB 1738258 A GB1738258 A GB 1738258A GB 819897 A GB819897 A GB 819897A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitrile
- acid
- trimethyl
- methyl
- cyclohexene
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title 1
- 229940045997 vitamin a Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 8
- 150000002825 nitriles Chemical class 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 5
- -1 halogen nitrile Chemical class 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 239000011701 zinc Substances 0.000 abstract 3
- 229910052725 zinc Inorganic materials 0.000 abstract 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000002266 vitamin A derivatives Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- MOQGCGNUWBPGTQ-UHFFFAOYSA-N 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde Chemical compound CC1=C(C=O)C(C)(C)CCC1 MOQGCGNUWBPGTQ-UHFFFAOYSA-N 0.000 abstract 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 abstract 1
- VODKOOOHHCAWFR-UHFFFAOYSA-N 2-iodoacetonitrile Chemical compound ICC#N VODKOOOHHCAWFR-UHFFFAOYSA-N 0.000 abstract 1
- DRUPNVWGYMKJFH-UHFFFAOYSA-N 2-methyldeca-2,4,6,8-tetraene Chemical compound CC(=CC=CC=CC=CC)C DRUPNVWGYMKJFH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 238000006680 Reformatsky reaction Methods 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-M all-trans-retinoate Chemical compound [O-]C(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-M 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 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
- 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
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229930002330 retinoic acid Natural products 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 238000007514 turning Methods 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
- 235000014692 zinc oxide Nutrition 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
- C07C403/20—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 carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE819897X | 1957-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB819897A true GB819897A (en) | 1959-09-09 |
Family
ID=6735785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17382/58A Expired GB819897A (en) | 1957-06-01 | 1958-05-30 | Process for the production of unsaturated compounds of the vitamin a series |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3021355A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1066197B (cg-RX-API-DMAC7.html) |
| GB (1) | GB819897A (cg-RX-API-DMAC7.html) |
| NL (1) | NL228279A (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190898A (en) * | 1965-06-22 | Method of producing compounds of the vitamin a series and intermediates for use therein | ||
| DE1157218B (de) * | 1960-08-03 | 1963-11-14 | Bayer Ag | Verfahren zur Herstellung von Verbindungen der Vitamin-A-Reihe |
| DE1149353B (de) * | 1960-08-03 | 1963-05-30 | Bayer Ag | Verfahren zur Herstellung von 6-[2', 6', 6'-Trimethylcyclohexen-(1')-yl]-4-methylhexadien-(3, 5)-in-(1) (íÀC-KohlenwasserstoffíÂ) |
| DE1156068B (de) * | 1960-12-16 | 1963-10-24 | Bayer Ag | Verfahren zur Herstellung von Verbindungen der Vitamin-A-Reihe |
| US3207759A (en) * | 1962-08-01 | 1965-09-21 | Hoffmann La Roche | Isoquinoline acetamides and acetonitriles |
| DE1156795B (de) * | 1962-08-22 | 1963-11-07 | Bayer Ag | Verfahren zur Herstellung von Acylderivaten tertiaerer Carbinole der Vitamin-A-Reihe |
| US3372033A (en) * | 1962-10-03 | 1968-03-05 | Philips Corp | Retinylydene cyano-acetic acid, esters and salts thereof, as an egg yolk colorant employed in poultry feed |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2369158A (en) * | 1941-10-01 | 1945-02-13 | Research Corp | Synthesis of vitamin a |
| US2583194A (en) * | 1948-04-27 | 1952-01-22 | Eastman Kodak Co | Vitamin a derivatives and methods of preparing the same |
| FR1022925A (fr) * | 1949-07-16 | 1953-03-11 | Philips Nv | Procédé de préparation de l'aldéhyde beta-ionylidène-acétique et de dérivés de ce corps |
| US2761878A (en) * | 1950-06-20 | 1956-09-04 | Hartford Nat Bank & Trust Co | beta ionylidene acetaldehyde and method of producing the same |
-
0
- DE DENDAT1066197D patent/DE1066197B/de active Pending
- NL NL228279D patent/NL228279A/xx unknown
-
1958
- 1958-05-28 US US738275A patent/US3021355A/en not_active Expired - Lifetime
- 1958-05-30 GB GB17382/58A patent/GB819897A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3021355A (en) | 1962-02-13 |
| DE1066197B (de) | 1959-10-01 |
| NL228279A (cg-RX-API-DMAC7.html) |
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