CH374065A - Verfahren zur Herstellung von Polyenaldehyden - Google Patents

Verfahren zur Herstellung von Polyenaldehyden

Info

Publication number: CH374065A
Authority: CH; Switzerland
Prior art keywords: trimethyl; cyclohexen; petroleum ether; hydrogen; aldehydes
Prior art date: 1958-08-28

Application number

CH6438358A

Other languages

German (de)

English (en)

Inventor

Otto Dr Isler

Herbert Dr Lindlar

Marc Dr Montavon

Rudolf Dr Rueegg

Gabriel Dr Saucy

Ulrich Dr Schwieter

Original Assignee

Hoffmann La Roche

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.)

1958-08-28

Filing date

1958-09-26

Publication date

1963-12-31

1958-08-28 Priority claimed from GB27590/58A external-priority patent/GB836961A/en

1958-09-26 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1963-12-31 Publication of CH374065A publication Critical patent/CH374065A/de

Links

-1 polyene aldehydes Chemical class 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 9
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 20
239000003054 catalyst Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
229910000019 calcium carbonate Inorganic materials 0.000 claims description 10
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
238000005984 hydrogenation reaction Methods 0.000 claims description 6
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
230000001419 dependent effect Effects 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
239000003208 petroleum Substances 0.000 description 34
238000010521 absorption reaction Methods 0.000 description 23
238000009835 boiling Methods 0.000 description 19
150000001299 aldehydes Chemical class 0.000 description 16
239000002904 solvent Substances 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000012298 atmosphere Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000002844 melting Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
150000001241 acetals Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000006317 isomerization reaction Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
VFKLNNIITLLGCQ-UHFFFAOYSA-N 2,7,11-trimethyltrideca-1,3,5,7,9-pentaene Chemical compound CC(=C)C=CC=CC(=CC=CC(CC)C)C VFKLNNIITLLGCQ-UHFFFAOYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000002923 oximes Chemical class 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
238000002360 preparation method Methods 0.000 description 2
150000007659 semicarbazones Chemical class 0.000 description 2
235000015096 spirit Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical compound C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 1
XDHOEHJVXXTEDV-HWKANZROSA-N (e)-1-ethoxyprop-1-ene Chemical compound CCO\C=C\C XDHOEHJVXXTEDV-HWKANZROSA-N 0.000 description 1
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 description 1
VXYSFSCCSQAYJV-UHFFFAOYSA-N 2-methylpropanedial Chemical compound O=CC(C)C=O VXYSFSCCSQAYJV-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
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 1
238000000862 absorption spectrum Methods 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
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 description 1
239000003674 animal food additive Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
210000003323 beak Anatomy 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013345 egg yolk Nutrition 0.000 description 1
210000002969 egg yolk Anatomy 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002932 luster Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
244000144977 poultry Species 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/47—Addition of dyes or pigments, e.g. in combination with optical brighteners using synthetic organic dyes or pigments not covered by groups A23L5/43 - A23L5/46

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Animal Husbandry (AREA)
Zoology (AREA)
Health & Medical Sciences (AREA)
Nutrition Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH6438358A 1958-08-28 1958-09-26 Verfahren zur Herstellung von Polyenaldehyden CH374065A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB27590/58A GB836961A (en)	1957-10-18	1958-08-28	A process for the manufacture of polyene aldehydes

Publications (1)

Publication Number	Publication Date
CH374065A true CH374065A (de)	1963-12-31

Family

ID=10262115

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6438358A CH374065A (de)	1958-08-28	1958-09-26	Verfahren zur Herstellung von Polyenaldehyden

Country Status (2)

Country	Link
CH (1)	CH374065A (da)
DK (1)	DK105585C (da)

1958
- 1958-09-26 CH CH6438358A patent/CH374065A/de unknown
- 1958-10-10 DK DK455161AA patent/DK105585C/da active

Also Published As

Publication number	Publication date
DK105585C (da)	1966-10-17

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