NO121909B - - Google Patents
Download PDFInfo
- Publication number
- NO121909B NO121909B NO89169A NO89169A NO121909B NO 121909 B NO121909 B NO 121909B NO 89169 A NO89169 A NO 89169A NO 89169 A NO89169 A NO 89169A NO 121909 B NO121909 B NO 121909B
- Authority
- NO
- Norway
- Prior art keywords
- vitamin
- acid
- jonylidene
- ester
- aluminum hydride
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- -1 cyanoacetic acid ester Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 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 claims description 17
- 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 claims description 16
- 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 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 235000019155 vitamin A Nutrition 0.000 claims description 15
- 239000011719 vitamin A Substances 0.000 claims description 15
- 229940045997 vitamin a Drugs 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 150000002825 nitriles Chemical class 0.000 claims description 14
- 150000004705 aldimines Chemical class 0.000 claims description 13
- 150000001299 aldehydes Chemical class 0.000 claims description 12
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 11
- 229930002330 retinoic acid Natural products 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 7
- 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 6
- 235000020945 retinal Nutrition 0.000 claims description 6
- 239000011604 retinal Substances 0.000 claims description 6
- 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 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 1
- CPDVHGLWIFENDJ-UHFFFAOYSA-N dihexylalumane Chemical compound C(CCCCC)[AlH]CCCCCC CPDVHGLWIFENDJ-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 238000006114 decarboxylation reaction Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003476 Darzens condensation reaction Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- LTVDFSLWFKLJDQ-DKGMKSHISA-N alpha-Tocopherolquinone Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-DKGMKSHISA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- ICKSOVDWLBHVCG-UHFFFAOYSA-N bis(4-methylpentyl)alumane Chemical compound C(CCC(C)C)[AlH]CCCC(C)C ICKSOVDWLBHVCG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid 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
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229960000342 retinol acetate Drugs 0.000 description 1
- 235000019173 retinyl acetate Nutrition 0.000 description 1
- 239000011770 retinyl acetate Substances 0.000 description 1
- 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 1
- 150000007659 semicarbazones Chemical class 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02P—CONTROL OR REGULATION OF ELECTRIC MOTORS, ELECTRIC GENERATORS OR DYNAMO-ELECTRIC CONVERTERS; CONTROLLING TRANSFORMERS, REACTORS OR CHOKE COILS
- H02P27/00—Arrangements or methods for the control of AC motors characterised by the kind of supply voltage
- H02P27/04—Arrangements or methods for the control of AC motors characterised by the kind of supply voltage using variable-frequency supply voltage, e.g. inverter or converter supply voltage
- H02P27/06—Arrangements or methods for the control of AC motors characterised by the kind of supply voltage using variable-frequency supply voltage, e.g. inverter or converter supply voltage using dc to ac converters or inverters
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02M—APPARATUS FOR CONVERSION BETWEEN AC AND AC, BETWEEN AC AND DC, OR BETWEEN DC AND DC, AND FOR USE WITH MAINS OR SIMILAR POWER SUPPLY SYSTEMS; CONVERSION OF DC OR AC INPUT POWER INTO SURGE OUTPUT POWER; CONTROL OR REGULATION THEREOF
- H02M5/00—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases
- H02M5/02—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases without intermediate conversion into dc
- H02M5/04—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases without intermediate conversion into dc by static converters
- H02M5/22—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases without intermediate conversion into dc by static converters using discharge tubes with control electrode or semiconductor devices with control electrode
- H02M5/25—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases without intermediate conversion into dc by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a thyratron or thyristor type requiring extinguishing means
- H02M5/27—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases without intermediate conversion into dc by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a thyratron or thyristor type requiring extinguishing means for conversion of frequency
- H02M5/271—Conversion of ac power input into ac power output, e.g. for change of voltage, for change of frequency, for change of number of phases without intermediate conversion into dc by static converters using discharge tubes with control electrode or semiconductor devices with control electrode using devices of a thyratron or thyristor type requiring extinguishing means for conversion of frequency from a three phase input voltage
Landscapes
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Control Of Ac Motors In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inverter Devices (AREA)
- Ac-Ac Conversion (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH325768A CH486801A (de) | 1967-04-25 | 1968-03-05 | Dreiphasige Umrichteranlage für die Speisung eines Drehstrommotors |
Publications (1)
Publication Number | Publication Date |
---|---|
NO121909B true NO121909B (de) | 1971-04-26 |
Family
ID=4252053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO89169A NO121909B (de) | 1968-03-05 | 1969-03-03 |
Country Status (7)
Country | Link |
---|---|
AT (1) | AT283521B (de) |
DE (1) | DE1812045B2 (de) |
FR (1) | FR2003234A6 (de) |
GB (1) | GB1192153A (de) |
NL (1) | NL6903235A (de) |
NO (1) | NO121909B (de) |
SE (1) | SE359416B (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4488216A (en) * | 1983-04-29 | 1984-12-11 | Westinghouse Electric Corp. | Unrestricted frequency changer system and adjustable frequency AC motor drive using such a system |
US4750098A (en) * | 1987-09-02 | 1988-06-07 | Westinghouse Electric Corp. | Unrestricted frequency changer with current source output |
-
1968
- 1968-11-15 AT AT1113868A patent/AT283521B/de not_active IP Right Cessation
- 1968-11-30 DE DE19681812045 patent/DE1812045B2/de not_active Withdrawn
-
1969
- 1969-03-03 NO NO89169A patent/NO121909B/no unknown
- 1969-03-03 GB GB1131969A patent/GB1192153A/en not_active Expired
- 1969-03-03 NL NL6903235A patent/NL6903235A/xx unknown
- 1969-03-03 SE SE289769A patent/SE359416B/xx unknown
- 1969-03-03 FR FR6905606A patent/FR2003234A6/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE1812045A1 (de) | 1970-05-27 |
FR2003234A6 (de) | 1969-11-07 |
SE359416B (de) | 1973-08-27 |
AT283521B (de) | 1970-08-10 |
GB1192153A (en) | 1970-05-20 |
DE1812045B2 (de) | 1971-11-18 |
NL6903235A (de) | 1969-09-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Wiberg et al. | Bicyclo [2.1. 1.] hexane Derivatives1 | |
van Tamelen et al. | The synthesis of tropone and tropolone via a norcarenone→ cycloheptadienone rearrangement | |
Stork et al. | Synthesis and Reactions of Glycidonitriles. Transformation into α-Haloacyl Compounds and Aminoalcohols | |
Cope et al. | Cyclic Polyolefins. XL. cis-cis-and cis-trans-1, 3-Cycloöctadiene from Cycloöcten-3-yldimethylamine1 | |
US3732292A (en) | Indenyl compounds | |
NO121909B (de) | ||
US2424994A (en) | Vitamin a acid and its esters and method of making them | |
SU492072A3 (ru) | Способ получени транс-хризантемовой кислоты | |
Johnson et al. | Cationic Cyclizations Involving Olefnic Bonds. III. 1 On the Mechanism of Formation of trans-Fused Rings | |
US2993056A (en) | Production of the 1-6-lactone of 6-hydroxy-8-acetoxy-octanoic acid | |
CN109574825B (zh) | 一种苯乙酸的合成方法 | |
Braun et al. | Esters of β-Diazopropionic Acid. A New Synthesis of β-Aryloxypropionic Acids1, 2 | |
CN111362784A (zh) | 一种黄樟油制备乙基香兰素的方法 | |
NO152308B (no) | Spjeldventil | |
US4360468A (en) | Preparation of 13-oxabicyclo[10.3.0]pentadecane | |
Naylor | 208. Syntheses in the thiopyran series. Part I. Tetrahydroderivatives | |
US4436939A (en) | Process for producing 1-(p-prenylphenyl)ethanol | |
CN117447303A (zh) | 萜品烯-4-醇及其合成方法 | |
DE2819594A1 (de) | Octylcyclohexanderivate, ihre herstellung und ihre verwendung als riechstoff | |
SU184837A1 (ru) | Метод получения 1,1-дифенилпропин-2-ола-1 | |
SU958409A1 (ru) | Способ получени 2е-додецен-1,12-дикарбоновой кислоты | |
Blicke et al. | The Reaction of Propylene Oxide, Styrene Oxide, and Cyclohexene Oxide with an Ivanov Reagent | |
Fuson et al. | β-Duroylphenylpropionic Acids | |
AT216680B (de) | Verfahren zur Herstellung von Vitamin A | |
Jackson | The synthesis of intermediates for conversion to cortisone analogues |