NO134075B - - Google Patents
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- Publication number
- NO134075B NO134075B NO740783A NO740783A NO134075B NO 134075 B NO134075 B NO 134075B NO 740783 A NO740783 A NO 740783A NO 740783 A NO740783 A NO 740783A NO 134075 B NO134075 B NO 134075B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- diacetamido
- ester
- triiodobenzoic
- methyl ester
- Prior art date
Links
- -1 for example Chemical group 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 24
- WFNIFAZYBYPWPG-UHFFFAOYSA-N methyl 3,5-diacetamido-2,4,6-triiodobenzoate Chemical compound COC(=O)C1=C(I)C(NC(C)=O)=C(I)C(NC(C)=O)=C1I WFNIFAZYBYPWPG-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- VEMBTDFKCRHMLA-UHFFFAOYSA-N methyl 3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoate Chemical compound CN(C(C)=O)C=1C(=C(C(=O)OC)C(=C(C1I)NC(C)=O)I)I VEMBTDFKCRHMLA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical class CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 31
- 239000002253 acid Substances 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- GGGDNPWHMNJRFN-UHFFFAOYSA-N metrizoic acid Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I GGGDNPWHMNJRFN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 10
- 150000004702 methyl esters Chemical class 0.000 description 10
- 230000026045 iodination Effects 0.000 description 9
- 238000006192 iodination reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000002872 contrast media Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 230000021736 acetylation Effects 0.000 description 5
- 238000006640 acetylation reaction Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 230000001365 aminolytic effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 238000010907 mechanical stirring Methods 0.000 description 4
- IYWLDOMAEQHKJZ-UHFFFAOYSA-N methyl 3,5-diaminobenzoate Chemical compound COC(=O)C1=CC(N)=CC(N)=C1 IYWLDOMAEQHKJZ-UHFFFAOYSA-N 0.000 description 4
- ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical compound [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000003024 amidolytic effect Effects 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- OBISGMNJKBVZBT-UHFFFAOYSA-N ethyl 3,5-diacetamido-2,4,6-triiodobenzoate Chemical compound CCOC(=O)C1=C(I)C(NC(C)=O)=C(I)C(NC(C)=O)=C1I OBISGMNJKBVZBT-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- POGCCFLNFPIIGW-UHFFFAOYSA-N methyl 3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 POGCCFLNFPIIGW-UHFFFAOYSA-N 0.000 description 3
- 239000012022 methylating agents Substances 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 2
- GOQCZMZLABPEME-UHFFFAOYSA-N 3,5-diamino-2,4,6-triiodobenzoic acid Chemical class NC1=C(I)C(N)=C(I)C(C(O)=O)=C1I GOQCZMZLABPEME-UHFFFAOYSA-N 0.000 description 2
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SBQHRXFHJGZTCG-UHFFFAOYSA-M potassium iodide hydrochloride Chemical compound Cl.I[K] SBQHRXFHJGZTCG-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PYPXLYUBVNNQJZ-UHFFFAOYSA-N 2,3-diacetamido-4,5,6-triiodobenzoic acid Chemical compound CC(=O)NC1=C(C(=C(C(=C1NC(=O)C)I)I)I)C(=O)O PYPXLYUBVNNQJZ-UHFFFAOYSA-N 0.000 description 1
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- OIXRDAZPDINJPT-UHFFFAOYSA-N 2,4,6-triiodo-3,5-bis(propanoylamino)benzoic acid Chemical compound CCC(=O)NC1=C(I)C(NC(=O)CC)=C(I)C(C(O)=O)=C1I OIXRDAZPDINJPT-UHFFFAOYSA-N 0.000 description 1
- ZBHSAYWIYAVUOP-UHFFFAOYSA-N 2-(benzylamino)-1-[3-(trifluoromethyl)phenyl]ethanol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(O)CNCC1=CC=CC=C1 ZBHSAYWIYAVUOP-UHFFFAOYSA-N 0.000 description 1
- HXLHPWRFRAZDQW-UHFFFAOYSA-N 3,5-bis[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid Chemical compound CC(=O)N(C)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(O)=O)=C1I HXLHPWRFRAZDQW-UHFFFAOYSA-N 0.000 description 1
- ZNVHAQRPXAQKRU-UHFFFAOYSA-N 3-amino-5-nitrobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZNVHAQRPXAQKRU-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- IDLVQOMJOKNXSL-UHFFFAOYSA-N ethyl 3,5-diaminobenzoate Chemical compound CCOC(=O)C1=CC(N)=CC(N)=C1 IDLVQOMJOKNXSL-UHFFFAOYSA-N 0.000 description 1
- IBQREHJPMPCXQA-UHFFFAOYSA-N ethyl 3,5-dinitrobenzoate Chemical compound CCOC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 IBQREHJPMPCXQA-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R4/00—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation
- H01R4/28—Clamped connections, spring connections
- H01R4/50—Clamped connections, spring connections utilising a cam, wedge, cone or ball also combined with a screw
- H01R4/5041—Clamped connections, spring connections utilising a cam, wedge, cone or ball also combined with a screw using a tapered groove
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R4/00—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation
- H01R4/28—Clamped connections, spring connections
- H01R4/50—Clamped connections, spring connections utilising a cam, wedge, cone or ball also combined with a screw
- H01R4/5016—Clamped connections, spring connections utilising a cam, wedge, cone or ball also combined with a screw using a cone
- H01R4/5025—Clamped connections, spring connections utilising a cam, wedge, cone or ball also combined with a screw using a cone combined with a threaded ferrule operating in a direction parallel to the conductor
Landscapes
- Connections Effected By Soldering, Adhesion, Or Permanent Deformation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Details Of Connecting Devices For Male And Female Coupling (AREA)
- Multi-Conductor Connections (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2311295A DE2311295C3 (de) | 1973-03-07 | 1973-03-07 | Klemmverbinder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134075B true NO134075B (fr) | 1976-05-03 |
| NO134075C NO134075C (fr) | 1976-08-11 |
Family
ID=5874040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO740783A NO134075C (fr) | 1973-03-07 | 1974-03-06 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3905671A (fr) |
| JP (1) | JPS50387A (fr) |
| BE (1) | BE811924A (fr) |
| CS (1) | CS168696B2 (fr) |
| DE (1) | DE2311295C3 (fr) |
| DK (1) | DK136286C (fr) |
| FR (1) | FR2220888B1 (fr) |
| GB (1) | GB1448522A (fr) |
| IE (1) | IE38919B1 (fr) |
| IT (1) | IT1003698B (fr) |
| LU (1) | LU69563A1 (fr) |
| NL (1) | NL7402822A (fr) |
| NO (1) | NO134075C (fr) |
| PL (1) | PL89870B1 (fr) |
| RO (1) | RO72369A (fr) |
| SE (1) | SE389946B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2553558C3 (de) * | 1975-11-28 | 1980-02-28 | Karl 7519 Oberderdingen Fischer | Elektrischer Steckanschluß |
| JPH0621329B2 (ja) * | 1984-07-09 | 1994-03-23 | 三菱重工業株式会社 | 銅合金鋳物の製造法 |
| JPS61113734A (ja) * | 1984-11-08 | 1986-05-31 | Mitsubishi Heavy Ind Ltd | 銅合金鋳物の製造法 |
| JPS6460496A (en) * | 1987-08-31 | 1989-03-07 | Mitsubishi Heavy Ind Ltd | Marine propeller |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2783442A (en) * | 1953-08-03 | 1957-02-26 | Thomas & Betts Corp | Method of and apparatus for forming electric terminals |
| US3251022A (en) * | 1963-08-19 | 1966-05-10 | Kemper M Hammell | Electrical connector clip |
| US3283289A (en) * | 1964-01-20 | 1966-11-01 | Amp Inc | Terminal clip |
| US3660806A (en) * | 1970-10-07 | 1972-05-02 | Thomas & Betts Corp | Connector |
| US3828298A (en) * | 1973-01-22 | 1974-08-06 | Amp Inc | Electrical terminal for a braided shield on a coaxial cable |
-
1973
- 1973-03-07 DE DE2311295A patent/DE2311295C3/de not_active Expired
-
1974
- 1974-02-18 GB GB735574A patent/GB1448522A/en not_active Expired
- 1974-02-22 IE IE00364/74A patent/IE38919B1/xx unknown
- 1974-02-26 CS CS1414A patent/CS168696B2/cs unknown
- 1974-03-01 NL NL7402822A patent/NL7402822A/xx not_active Application Discontinuation
- 1974-03-05 PL PL1974169315A patent/PL89870B1/pl unknown
- 1974-03-05 LU LU69563A patent/LU69563A1/xx unknown
- 1974-03-05 FR FR7407467A patent/FR2220888B1/fr not_active Expired
- 1974-03-05 US US448297A patent/US3905671A/en not_active Expired - Lifetime
- 1974-03-05 IT IT49022/74A patent/IT1003698B/it active
- 1974-03-06 BE BE141683A patent/BE811924A/fr unknown
- 1974-03-06 NO NO740783A patent/NO134075C/no unknown
- 1974-03-06 RO RO7477937A patent/RO72369A/fr unknown
- 1974-03-06 SE SE7402980A patent/SE389946B/xx unknown
- 1974-03-07 JP JP49026755A patent/JPS50387A/ja active Pending
- 1974-03-07 DK DK122174A patent/DK136286C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1448522A (en) | 1976-09-08 |
| NO134075C (fr) | 1976-08-11 |
| RO72369A (fr) | 1982-05-10 |
| PL89870B1 (fr) | 1976-12-31 |
| LU69563A1 (fr) | 1974-06-21 |
| DE2311295B2 (de) | 1975-01-02 |
| JPS50387A (fr) | 1975-01-06 |
| IE38919L (en) | 1974-09-07 |
| FR2220888A1 (fr) | 1974-10-04 |
| FR2220888B1 (fr) | 1979-01-26 |
| SE389946B (sv) | 1976-11-22 |
| NL7402822A (fr) | 1974-09-10 |
| DE2311295A1 (de) | 1974-09-19 |
| IE38919B1 (en) | 1978-06-21 |
| CS168696B2 (fr) | 1976-06-29 |
| DK136286C (da) | 1978-03-13 |
| US3905671A (en) | 1975-09-16 |
| BE811924A (fr) | 1974-09-06 |
| DE2311295C3 (de) | 1975-08-14 |
| IT1003698B (it) | 1976-06-10 |
| DK136286B (da) | 1977-09-19 |
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