CH383354A - Verfahren zur Herstellung von ungesättigten aliphatischen Säuren - Google Patents

Verfahren zur Herstellung von ungesättigten aliphatischen Säuren

Info

Publication number: CH383354A
Authority: CH; Switzerland
Prior art keywords: ether; sep; hours; added; acid
Prior art date: 1958-07-05

Application number

CH7472559A

Other languages

German (de)

English (en)

Inventor

Mervyn Dr Osbond John

George Dr Philpott Peter

Charles Wickens James

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.)

1958-07-05

Filing date

1959-06-22

Publication date

1964-10-31

1958-07-05 Priority claimed from GB21618/58A external-priority patent/GB859897A/en

1959-06-22 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1964-10-31 Publication of CH383354A publication Critical patent/CH383354A/de

Links

238000000034 method Methods 0.000 title claims description 13
125000001931 aliphatic group Chemical group 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 96
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 48
239000002253 acid Substances 0.000 claims description 33
239000010949 copper Substances 0.000 claims description 10
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 8
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 8
150000002366 halogen compounds Chemical class 0.000 claims description 7
150000001879 copper Chemical class 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 4
-1 organomagnesium halide compound Chemical class 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 158
239000000243 solution Substances 0.000 description 50
239000000203 mixture Substances 0.000 description 41
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
238000009835 boiling Methods 0.000 description 16
239000000284 extract Substances 0.000 description 16
238000010992 reflux Methods 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
229910000029 sodium carbonate Inorganic materials 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000012259 ether extract Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
238000001704 evaporation Methods 0.000 description 8
239000011777 magnesium Substances 0.000 description 8
229910052749 magnesium Inorganic materials 0.000 description 8
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 7
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 5
IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000012086 standard solution Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
230000002378 acidificating effect Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical class [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000011981 lindlar catalyst Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ZKEXILGWNQWRMH-UHFFFAOYSA-M [Br-].C(#CCCCCC)[Mg+] Chemical compound [Br-].C(#CCCCCC)[Mg+] ZKEXILGWNQWRMH-UHFFFAOYSA-M 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000061 acid fraction Substances 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
OFIDNKMQBYGNIW-UHFFFAOYSA-N arachidonic acid methyl ester Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC OFIDNKMQBYGNIW-UHFFFAOYSA-N 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
BEYVOSILLLPHNN-UHFFFAOYSA-N benzene;quinoline Chemical compound C1=CC=CC=C1.N1=CC=CC2=CC=CC=C21 BEYVOSILLLPHNN-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
235000004626 essential fatty acids Nutrition 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003517 fume Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
OFIDNKMQBYGNIW-ZKWNWVNESA-N methyl arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC OFIDNKMQBYGNIW-ZKWNWVNESA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/18—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/606—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom having only or additionally carbon-to-carbon triple bonds as unsaturation in the carboxylic acid moiety
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH7472559A 1958-07-05 1959-06-22 Verfahren zur Herstellung von ungesättigten aliphatischen Säuren CH383354A (de)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB21618/58A GB859897A (en)	1958-07-05	1958-07-05	Novel unsaturated acids and esters thereof and a process for the manufacture and conversion of same
GB3994058		1958-12-11
GB179559		1959-01-17
GB420759		1959-02-06
GB420659		1959-02-06

Publications (1)

Publication Number	Publication Date
CH383354A true CH383354A (de)	1964-10-31

Family

ID=27515688

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH7472559A CH383354A (de)	1958-07-05	1959-06-22	Verfahren zur Herstellung von ungesättigten aliphatischen Säuren
CH506864A CH396879A (de)	1958-07-05	1959-06-22	Verfahren zur Herstellung von ungesättigten aliphatischen Säuren

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH506864A CH396879A (de)	1958-07-05	1959-06-22	Verfahren zur Herstellung von ungesättigten aliphatischen Säuren

Country Status (4)

Country	Link
CH (2)	CH383354A (fr)
DK (1)	DK113710B (fr)
FR (1)	FR218M (fr)
SE (1)	SE309980B (fr)

1959
- 1959-06-22 CH CH7472559A patent/CH383354A/de unknown
- 1959-06-22 CH CH506864A patent/CH396879A/de unknown
- 1959-07-06 DK DK241559AA patent/DK113710B/da unknown
1960
- 1960-08-19 FR FR836200A patent/FR218M/fr not_active Expired
1961
- 1961-12-22 SE SE12890/61A patent/SE309980B/xx unknown

Also Published As

Publication number	Publication date
DK113710B (da)	1969-04-21
SE309980B (fr)	1969-04-14
FR218M (fr)	1961-02-27
CH396879A (de)	1965-08-15

Publication	Publication Date	Title
US3033884A (en)	1962-05-08	Unsaturated aliphatic compounds and process for the manufacture thereof
DE2439294A1 (de)	1975-02-27	Neue phenyl-alkenole und alkanole und verfahren zu deren herstellung
CH383354A (de)	1964-10-31	Verfahren zur Herstellung von ungesättigten aliphatischen Säuren
Birkinshaw	1952	Studies in the biochemistry of micro-organisms. 88. Palitantin. Part 2. Further derivatives and degradation products
AT211806B (de)	1960-11-10	Verfahren zur Herstellung von ungesättigten aliphatischen Verbindungen
DE2505446A1 (de)	1976-01-22	Neue organische verbindungen und verfahren zu deren herstellung
CH424753A (de)	1966-11-30	Verfahren zur Herstellung von Spirilloxanthin
AT211805B (de)	1960-11-10	Verfahren zur Herstellung von ungesättigten aliphatischen Verbindungen
DE1001259C2 (de)	1957-07-11	Verfahren zur Herstellung von Derivaten des Nortricyclens
DE892442C (de)	1953-10-08	Verfahren zur Reinigung von o-Methoxyphenylaceton
DE1275534B (de)	1968-08-22	Verfahren zur Herstellung von trans-10-Hydroxydecen-(2)-saeure
DE1768793B2 (de)	1979-05-10	Ungesättigte Aldehyde, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Tetraenaldehyden
DE1104498B (de)	1961-04-13	Verfahren zur Herstellung von Alkinolen
CH383353A (de)	1964-10-31	Verfahren zur Herstellung von ungesättigten aliphatischen Alkoholen
AT247847B (de)	1966-06-27	Verfahren zur Herstellung von neuen 5-(3'-Aminopropyliden)-5H-dibenzo [a, d] cycloheptenen bzw. den 10, 11-Dihydroderivaten derselben
EP0087712B1 (fr)	1986-05-07	Méthode de préparation de 3-cyano-2-alkylakanals et utilisation de 3-cyano-2-éthylhexanal pour la préparation de l'acide 2-propylpentanoique
CH218361A (de)	1941-12-15	Verfahren zur Herstellung einer Cyclopentano-dimethyl-polyhydro-phenanthren-carbonsäure.
EP0110309B1 (fr)	1986-02-19	Procédé de préparation de 1,4 diacyloxy-1,3-butadiènes
DE1025869B (de)	1958-03-13	Verfahren zur Herstellung von Vitamin-A-Saeure bzw. deren Estern
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CH436265A (de)	1967-05-31	Verfahren zur Herstellung von 15,15'-Dehydrozeaxanthin-dimethyläther und Zeaxanthin-dimethyläther