NO132141B - - Google Patents
Download PDFInfo
- Publication number
- NO132141B NO132141B NO3560/68A NO356068A NO132141B NO 132141 B NO132141 B NO 132141B NO 3560/68 A NO3560/68 A NO 3560/68A NO 356068 A NO356068 A NO 356068A NO 132141 B NO132141 B NO 132141B
- Authority
- NO
- Norway
- Prior art keywords
- solution
- dibenz
- alcohol
- dihydro
- azepine
- Prior art date
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 17
- 235000019253 formic acid Nutrition 0.000 claims description 17
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- FHYFQRCUSZETDW-UHFFFAOYSA-N 6,7-dihydro-5h-benzo[d][2]benzazepine Chemical class C1NCC2=CC=CC=C2C2=CC=CC=C12 FHYFQRCUSZETDW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000000155 melt Substances 0.000 description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
- 230000001476 alcoholic effect Effects 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 239000001569 carbon dioxide Substances 0.000 description 12
- 229910002092 carbon dioxide Inorganic materials 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 229910003446 platinum oxide Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- MMNUZQLGYHBLAD-UHFFFAOYSA-N 5h-benzo[d][2]benzazepin-5-ol Chemical compound OC1N=CC2=CC=CC=C2C2=CC=CC=C12 MMNUZQLGYHBLAD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000001177 diphosphate Substances 0.000 description 4
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 4
- 235000011180 diphosphates Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- DUUCAGQAOMZIGC-UHFFFAOYSA-N 6-butyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1N(CCCC)CC2=CC=CC=C2C2=CC=CC=C21 DUUCAGQAOMZIGC-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- LSPRUQXPQKPRDQ-UHFFFAOYSA-N 5,7-dihydrobenzo[d][2]benzazepine-6-carbaldehyde Chemical compound C1N(C=O)CC2=CC=CC=C2C2=CC=CC=C21 LSPRUQXPQKPRDQ-UHFFFAOYSA-N 0.000 description 2
- DJAMRLZIEKUCJX-UHFFFAOYSA-N 6,7-dihydro-5h-benzo[d][2]benzazepine;hydrochloride Chemical compound Cl.C1NCC2=CC=CC=C2C2=CC=CC=C12 DJAMRLZIEKUCJX-UHFFFAOYSA-N 0.000 description 2
- JQNQBWAAUPNGJU-UHFFFAOYSA-N 6-benzyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1C2=CC=CC=C2C2=CC=CC=C2CN1CC1=CC=CC=C1 JQNQBWAAUPNGJU-UHFFFAOYSA-N 0.000 description 2
- IUWNEWJWRCZZLG-UHFFFAOYSA-N 6-cyclohexyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1CCCCC1N1CC2=CC=CC=C2C2=CC=CC=C2C1 IUWNEWJWRCZZLG-UHFFFAOYSA-N 0.000 description 2
- HAISSBBARJYERH-UHFFFAOYSA-N 6-phenyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1C2=CC=CC=C2C2=CC=CC=C2CN1C1=CC=CC=C1 HAISSBBARJYERH-UHFFFAOYSA-N 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- NYGHGTMKALXFIA-UHFFFAOYSA-N azapetine Chemical compound C1N(CC=C)CC2=CC=CC=C2C2=CC=CC=C21 NYGHGTMKALXFIA-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- VDXGURZGBXUKES-UHFFFAOYSA-N 1-(bromomethyl)-2-[2-(bromomethyl)phenyl]benzene Chemical group BrCC1=CC=CC=C1C1=CC=CC=C1CBr VDXGURZGBXUKES-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HPEXVHVTTFAFRF-UHFFFAOYSA-N 6-methyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1N(C)CC2=CC=CC=C2C2=CC=CC=C21 HPEXVHVTTFAFRF-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 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 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- CHEIXKXUYLUNQK-UHFFFAOYSA-N benzo[d][2]benzazepine-5,7-dione Chemical compound O=C1NC(=O)C2=CC=CC=C2C2=CC=CC=C12 CHEIXKXUYLUNQK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 formyl compound Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- PTECIXPBVVDNOU-UHFFFAOYSA-N molecular bromine;hydrate Chemical compound O.BrBr PTECIXPBVVDNOU-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- SHIGCAOWAAOWIG-UHFFFAOYSA-N n-prop-2-enylformamide Chemical compound C=CCNC=O SHIGCAOWAAOWIG-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G65/00—Loading or unloading
- B65G65/30—Methods or devices for filling or emptying bunkers, hoppers, tanks, or like containers, of interest apart from their use in particular chemical or physical processes or their application in particular machines, e.g. not covered by a single other subclass
- B65G65/34—Emptying devices
- B65G65/40—Devices for emptying otherwise than from the top
- B65G65/48—Devices for emptying otherwise than from the top using other rotating means, e.g. rotating pressure sluices in pneumatic systems
- B65G65/4809—Devices for emptying otherwise than from the top using other rotating means, e.g. rotating pressure sluices in pneumatic systems rotating about a substantially vertical axis
- B65G65/4836—Devices for emptying otherwise than from the top using other rotating means, e.g. rotating pressure sluices in pneumatic systems rotating about a substantially vertical axis and moving material over a stationary surface, e.g. sweep arms or wheels
- B65G65/4854—Devices for emptying otherwise than from the top using other rotating means, e.g. rotating pressure sluices in pneumatic systems rotating about a substantially vertical axis and moving material over a stationary surface, e.g. sweep arms or wheels mounted on a carriage, e.g. for movement along slit-like outlets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B27/00—Arrangement of ship-based loading or unloading equipment for cargo or passengers
- B63B27/22—Arrangement of ship-based loading or unloading equipment for cargo or passengers of conveyers, e.g. of endless-belt or screw-type
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Ocean & Marine Engineering (AREA)
- Ship Loading And Unloading (AREA)
- Filling Or Emptying Of Bunkers, Hoppers, And Tanks (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Intermediate Stations On Conveyors (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO751999A NO751999L (nl) | 1967-09-11 | 1975-06-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66673667A | 1967-09-11 | 1967-09-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132141B true NO132141B (nl) | 1975-06-16 |
| NO132141C NO132141C (nl) | 1975-09-24 |
Family
ID=24675249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3560/68A NO132141C (nl) | 1967-09-11 | 1968-09-10 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3455467A (nl) |
| DE (1) | DE1781221A1 (nl) |
| FR (1) | FR1579853A (nl) |
| GB (1) | GB1175937A (nl) |
| NL (1) | NL162872C (nl) |
| NO (1) | NO132141C (nl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3613912A (en) * | 1969-10-31 | 1971-10-19 | Smith Harvestore Products | Unloading mechanism for sealed storage structure |
| US3642153A (en) * | 1970-04-24 | 1972-02-15 | Hewitt Robins Inc | Rotary plow feeder |
| GB2087364A (en) * | 1980-11-01 | 1982-05-26 | Liversedge Materials Handling | Discharging stored material |
| DE3510799A1 (de) * | 1985-03-25 | 1986-09-25 | Fried. Krupp Gmbh, 4300 Essen | Regelung und steuerung eines bunkerentleerungswagens fuer schlitzbunker |
| DE3612855A1 (de) * | 1986-04-16 | 1987-10-22 | Hans Juergen Dipl Ing Meyer | Austragevorrichtung fuer schuettgut |
| GB2377432B (en) * | 2001-05-05 | 2004-09-08 | Portasilo Ltd | Discharge means for a silo |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE481205C (de) * | 1929-09-11 | Christoph & Unmack A G | Grossraumbunker | |
| US1778533A (en) * | 1928-07-13 | 1930-10-14 | Herman E Meyer | Portable material-handling device |
| US1942839A (en) * | 1929-09-30 | 1934-01-09 | Robert E Sheal | Self-unloading boat |
| US2989171A (en) * | 1958-08-21 | 1961-06-20 | Link Belt Co | Rotary plow feeder |
-
1967
- 1967-09-11 US US666736A patent/US3455467A/en not_active Expired - Lifetime
-
1968
- 1968-09-05 GB GB42238/68A patent/GB1175937A/en not_active Expired
- 1968-09-10 NO NO3560/68A patent/NO132141C/no unknown
- 1968-09-10 DE DE19681781221 patent/DE1781221A1/de not_active Withdrawn
- 1968-09-10 NL NL6812912.A patent/NL162872C/nl not_active IP Right Cessation
- 1968-09-11 FR FR1579853D patent/FR1579853A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL162872C (nl) | 1980-07-15 |
| NO132141C (nl) | 1975-09-24 |
| DE1781221A1 (de) | 1970-10-29 |
| NL162872B (nl) | 1980-02-15 |
| US3455467A (en) | 1969-07-15 |
| FR1579853A (nl) | 1969-08-29 |
| NL6812912A (nl) | 1969-03-13 |
| GB1175937A (en) | 1970-01-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2636032A (en) | N, n'-disubstituted piperazines and process of preparing same | |
| EP0034349B1 (en) | Novel pyridinecarboxamide derivatives, a process for the preparation thereof, the use of said derivatives and a pharmaceutical composition containing same | |
| SU1253429A3 (ru) | Способ получени амидов карбоновой кислоты или их оптически активных антиподов,или их натриевых солей | |
| US4223034A (en) | Aniline derivatives | |
| NO132141B (nl) | ||
| Wuest et al. | Some Derivatives of 3-Pyridol with Parasympathomimetic Properties1 | |
| NO131149B (nl) | ||
| US3116283A (en) | Preparation of nitrogen heterocyclic | |
| US4167638A (en) | Process for production of 8-NHR quinolines | |
| Moffett et al. | Antispasmodics. VIII. Scopolamine Derivatives | |
| SU507242A3 (ru) | Способ получени производных теофиллина | |
| Osbond | 766. Chemical constitution and amœbicidal action. Part I. Synthesis of α-tetrahydro iso quinolino-ω-tetrahydro-1-iso quinolylalkanes related to emetine | |
| US3419561A (en) | 2,3,4,4a,5,6,10b-heptahydro-1-oxaphenanthridines and production thereof | |
| Gulland et al. | LXXVII.—Synthetical experiments on the aporphine alkaloids. Part I. A synthesis of 5: 6-dimethoxy-aporphine | |
| US3939172A (en) | 4-Aminothiazole | |
| US3378592A (en) | Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide | |
| King et al. | Antiplasmodial action and chemical constitution IX. Carbinolamines derived from 6: 7-dimethylquinoline | |
| US2824111A (en) | Pyrrolidines | |
| CN115232134B (zh) | 一种伐地那非类似物及其合成方法和应用 | |
| US4549021A (en) | N-(β-Fluoroethyl)-nortropine | |
| NO127583B (nl) | ||
| Atkinson et al. | Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 2. Non-glycolates | |
| SU425396A3 (ru) | Способ получения гексагидро-7я-азепиновых производных или их солей | |
| US1898258A (en) | Process for the production of phenyl-aminoalkyl-carbinols, which are substituted in the phenyl nucleus | |
| NO133067B (nl) |