NO121906B - - Google Patents
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- Publication number
- NO121906B NO121906B NO2172/69A NO217269A NO121906B NO 121906 B NO121906 B NO 121906B NO 2172/69 A NO2172/69 A NO 2172/69A NO 217269 A NO217269 A NO 217269A NO 121906 B NO121906 B NO 121906B
- Authority
- NO
- Norway
- Prior art keywords
- vitamin
- acid
- aluminum hydride
- reduction
- series
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002266 vitamin A derivatives Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000003138 primary alcohols Chemical class 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- -1 methyl-ethyl Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001649 bromium compounds Chemical class 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 7
- 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 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- 235000019155 vitamin A Nutrition 0.000 description 6
- 239000011719 vitamin A Substances 0.000 description 6
- 229940045997 vitamin a Drugs 0.000 description 6
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000001603 reducing effect Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229930002330 retinoic acid Natural products 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OBWAFSRXIGEEKA-YCNIQYBTSA-N (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl chloride Chemical compound ClC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OBWAFSRXIGEEKA-YCNIQYBTSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- SREQLAJQLXPNMC-DXYSAURFSA-N methyl (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate Chemical compound COC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SREQLAJQLXPNMC-DXYSAURFSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011734 sodium Substances 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
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G08—SIGNALLING
- G08C—TRANSMISSION SYSTEMS FOR MEASURED VALUES, CONTROL OR SIMILAR SIGNALS
- G08C15/00—Arrangements characterised by the use of multiplexing for the transmission of a plurality of signals over a common path
- G08C15/06—Arrangements characterised by the use of multiplexing for the transmission of a plurality of signals over a common path successively, i.e. using time division
- G08C15/12—Arrangements characterised by the use of multiplexing for the transmission of a plurality of signals over a common path successively, i.e. using time division the signals being represented by pulse characteristics in transmission link
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Relay Circuits (AREA)
- Electronic Switches (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE07091/68A SE333014B (en:Method) | 1968-05-28 | 1968-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121906B true NO121906B (en:Method) | 1971-04-26 |
Family
ID=20270393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2172/69A NO121906B (en:Method) | 1968-05-28 | 1969-05-27 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3575607A (en:Method) |
| BE (1) | BE733620A (en:Method) |
| FR (1) | FR2009503A1 (en:Method) |
| GB (1) | GB1270300A (en:Method) |
| NL (1) | NL6907442A (en:Method) |
| NO (1) | NO121906B (en:Method) |
| SE (1) | SE333014B (en:Method) |
| SU (1) | SU374875A3 (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376277A (en) * | 1980-10-17 | 1983-03-08 | Honeywell Inc. | Dynamic contact checking circuit |
| US4845475A (en) * | 1987-11-17 | 1989-07-04 | The Boeing Company | Automatic testing of position sensing devices employing stored sensed position |
| JP2669905B2 (ja) * | 1989-09-01 | 1997-10-29 | ファナック株式会社 | リレーの溶着検出方法 |
| DE9310446U1 (de) * | 1993-03-08 | 1994-07-14 | Landis & Gyr Business Support Ag, Zug | Schaltungsanordnung zum Prüfen von Schalter- bzw. Relaiskontakten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2800645A (en) * | 1955-01-27 | 1957-07-23 | Westinghouse Air Brake Co | Electric circuit integrity checking apparatus |
| US3452271A (en) * | 1967-01-17 | 1969-06-24 | United States Steel Corp | Apparatus for testing relays for operability,continuity and leakage |
-
1968
- 1968-05-28 SE SE07091/68A patent/SE333014B/xx unknown
-
1969
- 1969-04-23 US US818764A patent/US3575607A/en not_active Expired - Lifetime
- 1969-05-14 NL NL6907442A patent/NL6907442A/xx unknown
- 1969-05-20 SU SU1332692A patent/SU374875A3/ru active
- 1969-05-27 GB GB26807/69A patent/GB1270300A/en not_active Expired
- 1969-05-27 BE BE733620D patent/BE733620A/xx unknown
- 1969-05-27 NO NO2172/69A patent/NO121906B/no unknown
- 1969-05-28 FR FR6917381A patent/FR2009503A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE733620A (en:Method) | 1969-11-03 |
| DE1922139A1 (de) | 1970-06-18 |
| NL6907442A (en:Method) | 1969-12-02 |
| DE1922139B2 (de) | 1972-06-22 |
| GB1270300A (en) | 1972-04-12 |
| US3575607A (en) | 1971-04-20 |
| SE333014B (en:Method) | 1971-03-01 |
| SU374875A3 (en:Method) | 1973-03-20 |
| FR2009503A1 (en:Method) | 1970-02-06 |
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