CH420125A - Verfahren zur Herstellung von Vitamin-A-Alkohol - Google Patents

Verfahren zur Herstellung von Vitamin-A-Alkohol

Info

Publication number: CH420125A
Authority: CH; Switzerland
Prior art keywords: sep; vitamin; parts; reaction; formula
Prior art date: 1959-12-21

Application number

CH1355360A

Other languages

German (de)

English (en)

Inventor

Karl Dr Eiter

Ernst Dr Truscheit

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1959-12-21

Filing date

1960-12-02

Publication date

1966-09-15

1960-12-02 Application filed by Bayer Ag filed Critical Bayer Ag

1966-09-15 Publication of CH420125A publication Critical patent/CH420125A/de

Links

FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 title claims description 41
238000000034 method Methods 0.000 title claims description 30
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 title claims description 21
235000019169 all-trans-retinol Nutrition 0.000 title claims description 17
239000011717 all-trans-retinol Substances 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title description 5
238000006243 chemical reaction Methods 0.000 claims description 43
-1 propargyl halides Chemical class 0.000 claims description 30
NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 claims description 27
235000020945 retinal Nutrition 0.000 claims description 27
239000011604 retinal Substances 0.000 claims description 27
NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
239000011541 reaction mixture Substances 0.000 claims description 26
239000004215 Carbon black (E152) Substances 0.000 claims description 24
229930195733 hydrocarbon Natural products 0.000 claims description 23
PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 22
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 21
SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
239000007795 chemical reaction product Substances 0.000 claims description 11
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
230000008030 elimination Effects 0.000 claims description 8
238000003379 elimination reaction Methods 0.000 claims description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 7
239000003513 alkali Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
229940088594 vitamin Drugs 0.000 claims description 6
239000011782 vitamin Substances 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 5
150000004681 metal hydrides Chemical class 0.000 claims description 5
229930003231 vitamin Natural products 0.000 claims description 5
235000013343 vitamin Nutrition 0.000 claims description 5
150000003722 vitamin derivatives Chemical class 0.000 claims description 5
239000011701 zinc Substances 0.000 claims description 5
238000002329 infrared spectrum Methods 0.000 claims description 4
238000010653 organometallic reaction Methods 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000006227 byproduct Substances 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 48
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 23
238000003786 synthesis reaction Methods 0.000 description 19
150000002430 hydrocarbons Chemical class 0.000 description 18
239000002904 solvent Substances 0.000 description 18
238000003756 stirring Methods 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 16
239000003208 petroleum Substances 0.000 description 15
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
150000001875 compounds Chemical class 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000010521 absorption reaction Methods 0.000 description 13
239000012298 atmosphere Substances 0.000 description 13
239000011261 inert gas Substances 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 12
230000007935 neutral effect Effects 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000010409 thin film Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000011877 solvent mixture Substances 0.000 description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
239000005457 ice water Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
230000008707 rearrangement Effects 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000862 absorption spectrum Methods 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
229950000688 phenothiazine Drugs 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 5
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
239000003963 antioxidant agent Substances 0.000 description 5
235000006708 antioxidants Nutrition 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
150000007522 mineralic acids Chemical class 0.000 description 5
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 5
229940042585 tocopherol acetate Drugs 0.000 description 5
235000019155 vitamin A Nutrition 0.000 description 5
239000011719 vitamin A Substances 0.000 description 5
229940045997 vitamin a Drugs 0.000 description 5
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
230000003078 antioxidant effect Effects 0.000 description 4
OEYOHULQRFXULB-UHFFFAOYSA-N arsenic trichloride Chemical compound Cl[As](Cl)Cl OEYOHULQRFXULB-UHFFFAOYSA-N 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 4
ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
235000019173 retinyl acetate Nutrition 0.000 description 4
239000011770 retinyl acetate Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229960004337 hydroquinone Drugs 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
150000007530 organic bases Chemical group 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229960000342 retinol acetate Drugs 0.000 description 3
QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
AKGUXECGGCUDCV-POHAHGRESA-N [(z)-benzylideneamino]urea Chemical compound NC(=O)N\N=C/C1=CC=CC=C1 AKGUXECGGCUDCV-POHAHGRESA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
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239000008346 aqueous phase Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
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239000001257 hydrogen Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
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239000012452 mother liquor Substances 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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229910052708 sodium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
150000002266 vitamin A derivatives Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
ADFWQBGTDJIESE-UHFFFAOYSA-N anacardic acid Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1C(O)=O ADFWQBGTDJIESE-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000004792 aryl magnesium halides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
125000005621 boronate group Chemical class 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
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229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000000306 component Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
238000007700 distillative separation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
239000011981 lindlar catalyst Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
229960001206 phenicarbazide Drugs 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 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
- C07C403/06—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 singly-bound oxygen atoms
- C07C403/10—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 singly-bound oxygen atoms by etherified hydroxy groups
- 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
- C07C403/02—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 containing only carbon and hydrogen atoms
- 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
- C07C403/06—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 singly-bound oxygen atoms
- C07C403/08—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 singly-bound oxygen atoms by hydroxy groups
- 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
- C07C403/06—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 singly-bound oxygen atoms
- C07C403/12—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 singly-bound oxygen atoms by esterified hydroxy groups
- 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
- C07C403/14—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 doubly-bound oxygen atoms
- 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)

CH1355360A 1959-12-21 1960-12-02 Verfahren zur Herstellung von Vitamin-A-Alkohol CH420125A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF30143A DE1110156B (de)	1959-12-21	1959-12-21	Verfahren zur Herstellung von 6-[2',6',6'-Trimethylcyclohexen-(1')-yl]-4-methylhexadien-(3,5)-in-(1)

Publications (1)

Publication Number	Publication Date
CH420125A true CH420125A (de)	1966-09-15

Family

ID=7093621

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1355360A CH420125A (de)	1959-12-21	1960-12-02	Verfahren zur Herstellung von Vitamin-A-Alkohol

Country Status (6)

Country	Link
AT (2)	AT244512B (fr)
BE (1)	BE598290A (fr)
CH (1)	CH420125A (fr)
DE (1)	DE1110156B (fr)
DK (1)	DK104563C (fr)
GB (1)	GB899991A (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1028118B (de) *	1951-09-11	1958-04-17	Eastman Kodak Co	Verfahren zur Herstellung von Vitamin A-aldehyd, -alkohol bzw. dessen Estern
DE1076681B (de)	1951-09-11	1960-03-03	Eastman Kodak Co	Verfahren zur Herstellung von Vitamin A-aldehyd
DE1059445B (de) *	1951-09-11	1959-06-18	Eastman Kodak Co	Verfahren zur synthetischen Herstellung von Vitamin A-aldehyd, -alkohol bzw. dessen Estern

1959
- 1959-12-21 DE DEF30143A patent/DE1110156B/de active Pending
1960
- 1960-12-02 CH CH1355360A patent/CH420125A/de unknown
- 1960-12-14 GB GB43078/60A patent/GB899991A/en not_active Expired
- 1960-12-19 BE BE598290A patent/BE598290A/fr unknown
- 1960-12-19 AT AT947060A patent/AT244512B/de active
- 1960-12-19 AT AT477661A patent/AT245739B/de active
- 1960-12-20 DK DK503860AA patent/DK104563C/da active

Also Published As

Publication number	Publication date
AT245739B (de)	1966-03-10
DK104563C (da)	1966-06-06
GB899991A (en)	1962-06-27
AT244512B (de)	1966-01-10
DE1110156B (de)	1961-07-06
BE598290A (fr)	1961-06-19

Publication	Publication Date	Title
DE2729859C2 (de)	1984-08-23	Verfahren zur Herstellung von 6a,10a-cis- oder -trans-1-Hydroxy-3-alkyl-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-onen
EP0263259B1 (fr)	1991-06-19	Procédé et système catalytique pour la trimérisation d'acétylène et composéss d'acétylène
DE2166398B2 (de)	1977-10-27	4,5-tetrazolo- eckige klammer auf 1,5-a eckige klammer zu chinoline und verfahren zu ihrer herstellung
EP0015436B1 (fr)	1982-02-03	Procédé de fabrication stéréospécifique de composés appartenant à la famille des vitamines K1 et K2 ainsi que des produits de départ pour ce procédé
DE2424806A1 (de)	1975-02-27	Antikoagulantien, verfahren zu ihrer herstellung und ihre verwendung
DE2516696C3 (de)	1979-09-13	Riechstoffe der 3,6,6-Trimethyll-(but-3-enoyl)-cyclohexenreihe, Verfahren zu deren Herstellung und diese enthaltende Riechstoffkompositionen
DE3034040C2 (de)	1987-04-30	Verfahren zur Herstellung von Muscon, 16-Oxa-14-methyl-bicyclo[10.3.1]-hexadec-1-en als Zwischenprodukt für dieses Verfahren und ein Verfahren zu dessen Herstellung
EP0003825A1 (fr)	1979-09-05	Procédé de préparation de l'acide 4-hydroxyphénylacétique
DE1642646B2 (de)	1973-09-27	Verfahren zur Herstellung der Coenzyme Q tief 9, Q tief 11, Q tief 12 und Q tief 10
CH420125A (de)	1966-09-15	Verfahren zur Herstellung von Vitamin-A-Alkohol
DE2248525A1 (de)	1973-04-19	Verfahren zur decarboxylierung von ortho- oder para-hydroxyarylcarbonsaeuren
CH421079A (de)	1966-09-30	Verfahren zur Herstellung eines Diols und von Derivaten desselben
DE818942C (de)	1951-10-29	Verfahren zur Herstellung von ª‰-Carotin
DE2729846C2 (de)	1982-08-19	Verfahren zur Herstellung von in 3-Stellung alkylsubstituierten cis-1-Hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo [b,d] pyran-9-onen
EP0036651B1 (fr)	1983-05-11	Préparation de 3-oxo-alpha-ionone
EP0882709A1 (fr)	1998-12-09	Procédé pour la préparation de la zéaxanthine, intermédiaires pour ce procédé et procédé pour leur préparation
DE2164662A1 (de)	1972-07-27	Indanderivate und Verfahren zu ihrer Herstellung
AT214909B (de)	1961-05-10	Verfahren zur Herstellung von ungesättigten Ketonen
DE1618782A1 (de)	1971-01-28	Neue tricyclische Verbindungen und Verfahren zur Herstellung von tricyclischen Verbindungen
CH625495A5 (fr)	1981-09-30
DE1118191B (de)	1961-11-30	Verfahren zur Herstellung von ungesaettigten Ketonen
DE845043C (de)	1952-07-28	Verfahren zur Herstellung von Pentaenen (Vitamin-A-AEther)
AT264726B (de)	1968-09-10	Verfahren zur Herstellung von Verbindungen der Vitamin A-Reihe
DE839495C (de)	1952-05-19	Verfahren zur Darstellung von Pentaenen (Vitamin A-Alkohol bzw. dessen Ester)
DE1493890C3 (de)	1978-06-15	Verfahren zur Herstellung von ß- (5-Nitro-2-furyl)acrolein