NO131906B - - Google Patents
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- Publication number
- NO131906B NO131906B NO57973A NO57973A NO131906B NO 131906 B NO131906 B NO 131906B NO 57973 A NO57973 A NO 57973A NO 57973 A NO57973 A NO 57973A NO 131906 B NO131906 B NO 131906B
- Authority
- NO
- Norway
- Prior art keywords
- group
- hydrogen atom
- formula
- methyl
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- -1 methylene, ethylidene Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002820 allylidene group Chemical group [H]C(=[*])C([H])=C([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 claims description 2
- 150000004008 N-nitroso compounds Chemical class 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 230000009935 nitrosation Effects 0.000 claims 1
- 238000007034 nitrosation reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- KTNPVRSKFWZJEZ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-1-amine Chemical compound CC1(C)CCCC(C)(C)N1N KTNPVRSKFWZJEZ-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 6
- 229940071870 hydroiodic acid Drugs 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- ZBLNPMXAFVVOQK-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-nitrosopiperidine Chemical compound CC1(C)CCCC(C)(C)N1N=O ZBLNPMXAFVVOQK-UHFFFAOYSA-N 0.000 description 2
- MLBJXMUATUQUCI-UHFFFAOYSA-N 2,2,6,6-tetramethyl-3H-pyridin-1-amine Chemical compound NN1C(C=CCC1(C)C)(C)C MLBJXMUATUQUCI-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- CACSBIPHLOZMJQ-UHFFFAOYSA-N NN1C(C=C(CC1(C)C)C)(C)C Chemical compound NN1C(C=C(CC1(C)C)C)(C)C CACSBIPHLOZMJQ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SQSZJFNQVXYHJO-UHFFFAOYSA-N n,2,2,6,6-pentamethylpiperidin-1-amine Chemical compound CNN1C(C)(C)CCCC1(C)C SQSZJFNQVXYHJO-UHFFFAOYSA-N 0.000 description 2
- FUZUXFGUZUHTCB-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-1-yl)methanimine Chemical compound CC1(C)CCCC(C)(C)N1N=C FUZUXFGUZUHTCB-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical class NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- POPVUKGJWNLYGW-UHFFFAOYSA-N (hydroxyamino) hydrogen sulfate Chemical compound ONOS(O)(=O)=O POPVUKGJWNLYGW-UHFFFAOYSA-N 0.000 description 1
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- KEHRVXCBFSPWOH-UHFFFAOYSA-N 1-aminopiperidin-4-ol Chemical class NN1CCC(O)CC1 KEHRVXCBFSPWOH-UHFFFAOYSA-N 0.000 description 1
- KPHGKPWFWXMBHO-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-1-nitroso-3H-pyridine Chemical compound N(=O)N1C(C=C(CC1(C)C)C)(C)C KPHGKPWFWXMBHO-UHFFFAOYSA-N 0.000 description 1
- NFCIMBZDJLFHNB-UHFFFAOYSA-N 2,2,4,6,6-pentamethylpiperidin-4-ol Chemical compound CC1(C)CC(C)(O)CC(C)(C)N1 NFCIMBZDJLFHNB-UHFFFAOYSA-N 0.000 description 1
- ZYDUNXCLPOKBNQ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1,3-dihydropyridine Chemical compound CC1(C)CC=CC(C)(C)N1 ZYDUNXCLPOKBNQ-UHFFFAOYSA-N 0.000 description 1
- KQFMVRIOMKZYBN-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-nitroso-3H-pyridine Chemical compound N(=O)N1C(C=CCC1(C)C)(C)C KQFMVRIOMKZYBN-UHFFFAOYSA-N 0.000 description 1
- XURVRIOXAKCOIM-UHFFFAOYSA-N 2,2,6-trimethyl-1-nitrosopiperidine Chemical compound N(=O)N1C(CCCC1C)(C)C XURVRIOXAKCOIM-UHFFFAOYSA-N 0.000 description 1
- QARRCHMPOZWNED-UHFFFAOYSA-N 2,2,6-trimethylpiperidine Chemical compound CC1CCCC(C)(C)N1 QARRCHMPOZWNED-UHFFFAOYSA-N 0.000 description 1
- UAHWWAIVYPJROV-UHFFFAOYSA-N 2,6-dimethylpiperidin-1-amine Chemical compound CC1CCCC(C)N1N UAHWWAIVYPJROV-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JUCVKIXRNWXWNI-UHFFFAOYSA-N C(#N)C1(N(C(CCC1)(C)C#N)N)C Chemical compound C(#N)C1(N(C(CCC1)(C)C#N)N)C JUCVKIXRNWXWNI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical class OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OGCOKBPLWOFBAP-UHFFFAOYSA-N NN1C(C=2C=CC=CC=2)CCCC1C1=CC=CC=C1 Chemical compound NN1C(C=2C=CC=CC=2)CCCC1C1=CC=CC=C1 OGCOKBPLWOFBAP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000005400 Synovial Cyst Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical class OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000003457 ganglion blocking agent Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- WBMYCZIJLAZZLZ-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-1-yl)ethanimine Chemical compound CC=NN1C(C)(C)CCCC1(C)C WBMYCZIJLAZZLZ-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G05—CONTROLLING; REGULATING
- G05B—CONTROL OR REGULATING SYSTEMS IN GENERAL; FUNCTIONAL ELEMENTS OF SUCH SYSTEMS; MONITORING OR TESTING ARRANGEMENTS FOR SUCH SYSTEMS OR ELEMENTS
- G05B19/00—Programme-control systems
- G05B19/02—Programme-control systems electric
- G05B19/42—Recording and playback systems, i.e. in which the programme is recorded from a cycle of operations, e.g. the cycle of operations being manually controlled, after which this record is played back on the same machine
- G05B19/423—Teaching successive positions by walk-through, i.e. the tool head or end effector being grasped and guided directly, with or without servo-assistance, to follow a path
-
- G—PHYSICS
- G05—CONTROLLING; REGULATING
- G05B—CONTROL OR REGULATING SYSTEMS IN GENERAL; FUNCTIONAL ELEMENTS OF SUCH SYSTEMS; MONITORING OR TESTING ARRANGEMENTS FOR SUCH SYSTEMS OR ELEMENTS
- G05B2219/00—Program-control systems
- G05B2219/30—Nc systems
- G05B2219/41—Servomotor, servo controller till figures
- G05B2219/41309—Hydraulic or pneumatic drive
Landscapes
- Engineering & Computer Science (AREA)
- Robotics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Automation & Control Theory (AREA)
- Numerical Control (AREA)
- Manipulator (AREA)
- Control Of Position Or Direction (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO57973A NO131906C (xx) | 1973-02-13 | 1973-02-13 | |
| GB608874A GB1431413A (en) | 1973-02-13 | 1974-02-11 | Method of programming a servo system and a servo system designed for such programming |
| SE7401804A SE404406B (sv) | 1973-02-13 | 1974-02-11 | Sett for programmering av minst ett for genomforande av en efterfoljande arbetsoperation avsett, hydrauliskt eller pneumatiskt servosystem och servosystem avsett for sadan programmering |
| IT4824874A IT1008824B (it) | 1973-02-13 | 1974-02-11 | Procedimento per programmare un servosistema e servosistema relati vo |
| AU65527/74A AU483598B2 (en) | 1974-02-12 | Procedure for programming a servo system, and servo system designed for such programming | |
| DE19742406493 DE2406493C2 (de) | 1973-02-13 | 1974-02-12 | Programmierbares Servosystem zur Führung eines Werkzeuges, insbesondere einer Spritzpistole |
| JP1750274A JPS5040985A (xx) | 1973-02-13 | 1974-02-13 | |
| FR7404806A FR2217741B1 (xx) | 1973-02-13 | 1974-02-13 | |
| JP5700781U JPS6039103U (ja) | 1973-02-13 | 1981-04-20 | サ−ボシステム |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO57973A NO131906C (xx) | 1973-02-13 | 1973-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131906B true NO131906B (xx) | 1975-05-12 |
| NO131906C NO131906C (xx) | 1975-08-20 |
Family
ID=19877683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO57973A NO131906C (xx) | 1973-02-13 | 1973-02-13 |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPS5040985A (xx) |
| DE (1) | DE2406493C2 (xx) |
| FR (1) | FR2217741B1 (xx) |
| GB (1) | GB1431413A (xx) |
| IT (1) | IT1008824B (xx) |
| NO (1) | NO131906C (xx) |
| SE (1) | SE404406B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2498493A1 (fr) * | 1981-01-26 | 1982-07-30 | Rondolotti Ets | Tour de repoussage perfectionne |
| NO148986C (no) * | 1981-10-05 | 1984-01-25 | Ole Molaug | Anordning ved robotmanipulator |
| GB2124407A (en) * | 1982-06-03 | 1984-02-15 | Zed Instr Ltd | Control of hydraulic booms |
| NL8301678A (nl) * | 1983-05-11 | 1984-12-03 | Johan Massee | Forceermachine. |
| US5004392A (en) * | 1984-02-20 | 1991-04-02 | Zoller-Kipper Gmbh | Device for emptying containers, especially refuse bins |
| JPS6198411A (ja) * | 1984-10-20 | 1986-05-16 | Hitachi Constr Mach Co Ltd | 再生装置 |
| JPS621004A (ja) * | 1985-05-30 | 1987-01-07 | Matsushita Electric Ind Co Ltd | ロボツト |
| CN114017406B (zh) * | 2021-11-16 | 2024-08-16 | 成都大宏立机器股份有限公司 | 一种全自动疲劳强度试验机的液压系统 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3246223A (en) * | 1962-05-03 | 1966-04-12 | American Mach & Foundry | Selective condition limiting recording system for a motor controlled machine tool |
| CA918789A (en) * | 1969-03-18 | 1973-01-09 | F. Engelberger Joseph | Programmed manipulator apparatus |
-
1973
- 1973-02-13 NO NO57973A patent/NO131906C/no unknown
-
1974
- 1974-02-11 SE SE7401804A patent/SE404406B/xx not_active IP Right Cessation
- 1974-02-11 GB GB608874A patent/GB1431413A/en not_active Expired
- 1974-02-11 IT IT4824874A patent/IT1008824B/it active
- 1974-02-12 DE DE19742406493 patent/DE2406493C2/de not_active Expired
- 1974-02-13 JP JP1750274A patent/JPS5040985A/ja active Pending
- 1974-02-13 FR FR7404806A patent/FR2217741B1/fr not_active Expired
-
1981
- 1981-04-20 JP JP5700781U patent/JPS6039103U/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2217741B1 (xx) | 1977-09-23 |
| NO131906C (xx) | 1975-08-20 |
| IT1008824B (it) | 1976-11-30 |
| SE404406B (sv) | 1978-10-02 |
| AU6552774A (en) | 1975-08-14 |
| FR2217741A1 (xx) | 1974-09-06 |
| GB1431413A (en) | 1976-04-07 |
| JPS5040985A (xx) | 1975-04-15 |
| DE2406493A1 (de) | 1974-08-15 |
| JPS6039103U (ja) | 1985-03-18 |
| DE2406493C2 (de) | 1986-02-13 |
| JPS6117448Y2 (xx) | 1986-05-28 |
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