NO132616B - - Google Patents
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- Publication number
- NO132616B NO132616B NO4571/72A NO457172A NO132616B NO 132616 B NO132616 B NO 132616B NO 4571/72 A NO4571/72 A NO 4571/72A NO 457172 A NO457172 A NO 457172A NO 132616 B NO132616 B NO 132616B
- Authority
- NO
- Norway
- Prior art keywords
- amide
- ammonia
- acid
- cyano
- seminitrile
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 70
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 44
- 150000001408 amides Chemical class 0.000 claims description 33
- 229910021529 ammonia Inorganic materials 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- 150000004702 methyl esters Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- LADVLNYAMWAFOR-UHFFFAOYSA-N C(#N)CC=CC=CCC(=O)N Chemical compound C(#N)CC=CC=CCC(=O)N LADVLNYAMWAFOR-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- OISXOUGTIYAWAZ-UHFFFAOYSA-N 7-cyanohepta-2,5-dienoic acid Chemical compound OC(=O)C=CCC=CCC#N OISXOUGTIYAWAZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- RNVCRFXUWMKKLD-UHFFFAOYSA-N methyl 7-cyanohepta-2,5-dienoate Chemical compound C(#N)CC=CCC=CC(=O)OC RNVCRFXUWMKKLD-UHFFFAOYSA-N 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010276 construction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- -1 cyano-3,5-heptadienoic acid amide Chemical compound 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- RQIQSOTYUAOLIY-UHFFFAOYSA-N 2-aminooctanamide Chemical compound CCCCCCC(N)C(N)=O RQIQSOTYUAOLIY-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QZGIOJSVUOCUMC-YTXTXJHMSA-N (2e,4e)-octa-2,4-dienoic acid Chemical compound CCC\C=C\C=C\C(O)=O QZGIOJSVUOCUMC-YTXTXJHMSA-N 0.000 description 1
- AKVBCGQVQXPRLD-UHFFFAOYSA-N 2-aminooctanoic acid Chemical compound CCCCCCC(N)C(O)=O AKVBCGQVQXPRLD-UHFFFAOYSA-N 0.000 description 1
- DEMIMHOMFTVNDW-UHFFFAOYSA-N 2-chloropent-2-enenitrile Chemical compound ClC(=CCC)C#N DEMIMHOMFTVNDW-UHFFFAOYSA-N 0.000 description 1
- XOTACOSOWLORPP-UHFFFAOYSA-N 7-cyanohepta-2,5-dienamide Chemical compound C(#N)CC=CCC=CC(=O)N XOTACOSOWLORPP-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- PPWCZNFCSAJMBS-UHFFFAOYSA-N octa-3,6-dienenitrile Chemical compound CC=CCC=CCC#N PPWCZNFCSAJMBS-UHFFFAOYSA-N 0.000 description 1
- NFVUAUVSFDFOJT-UHFFFAOYSA-N octanediamide Chemical compound NC(=O)CCCCCCC(N)=O NFVUAUVSFDFOJT-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A63—SPORTS; GAMES; AMUSEMENTS
- A63H—TOYS, e.g. TOPS, DOLLS, HOOPS OR BUILDING BLOCKS
- A63H33/00—Other toys
- A63H33/04—Building blocks, strips, or similar building parts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S52/00—Static structures, e.g. buildings
- Y10S52/10—Polyhedron
Landscapes
- Toys (AREA)
- Investigation Of Foundation Soil And Reinforcement Of Foundation Soil By Compacting Or Drainage (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK606771AA DK127955B (da) | 1971-12-13 | 1971-12-13 | Byggesæt. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132616B true NO132616B (de) | 1975-09-01 |
| NO132616C NO132616C (de) | 1975-12-10 |
Family
ID=8147176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4571/72A NO132616C (de) | 1971-12-13 | 1972-12-11 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3822569A (de) |
| JP (1) | JPS4865039A (de) |
| AT (1) | AT332766B (de) |
| AU (1) | AU470389B2 (de) |
| BE (1) | BE792683A (de) |
| CA (1) | CA963657A (de) |
| CH (1) | CH559567A5 (de) |
| DE (1) | DE2260228A1 (de) |
| DK (1) | DK127955B (de) |
| FR (1) | FR2170436A5 (de) |
| GB (1) | GB1377239A (de) |
| IE (1) | IE37207B1 (de) |
| IT (1) | IT971777B (de) |
| NL (1) | NL7216579A (de) |
| NO (1) | NO132616C (de) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2224521A1 (de) * | 1972-05-19 | 1973-11-22 | Heitz Walter Helmut | Tuerschloss mit verriegelbarer falle |
| GB1475284A (en) * | 1973-05-25 | 1977-06-01 | Credelca Ag | Buildings |
| GB1460111A (en) * | 1974-02-22 | 1976-12-31 | Galvagni M | Three-dimensional pre-fabricated structural elements to be assembled in habitation units |
| LU77983A1 (de) * | 1977-08-17 | 1978-02-13 | ||
| CH625947A5 (de) * | 1978-01-27 | 1981-10-30 | Wagner Hans Ruedi | |
| US4553749A (en) * | 1983-10-14 | 1985-11-19 | Bender Robert L | Toy and game apparatus |
| JPS6073597U (ja) * | 1983-10-27 | 1985-05-23 | 株式会社タカラ | 組立玩具 |
| DE3602630A1 (de) * | 1986-01-29 | 1987-07-30 | Gunter Dr Feddern | Spiel-baustein-satz |
| US4744533A (en) * | 1986-08-25 | 1988-05-17 | Mullen Charles F | Modular space station |
| US5893241A (en) * | 1998-01-05 | 1999-04-13 | Schroeder; Michael P. | Precast concrete target house |
| US6035585A (en) * | 1998-04-06 | 2000-03-14 | Boyd; Jon Taylor | Apparatus and method for a portable, modular, vehicle washing and servicing structure |
| CA2282212C (en) * | 1999-08-23 | 2001-11-06 | Steven G. Williams | Card and marble game |
| US6386936B1 (en) * | 2000-05-08 | 2002-05-14 | Philippe Gebara | Building block set |
| US7747352B2 (en) * | 2004-04-20 | 2010-06-29 | Massachusetts Institute Of Technology | Physical modeling system for constructing and controlling articulated forms with motorized joints |
| US20100077685A1 (en) * | 2008-09-29 | 2010-04-01 | Andersen Jr Clinton Joe | Veneer panel |
| US8065840B2 (en) * | 2009-04-06 | 2011-11-29 | Syed Azmat Ali Zaidi | Modular building construction system and method of constructing |
| USD667507S1 (en) * | 2010-03-15 | 2012-09-18 | Taranto Estudios e Inversiones, S.L. | Set of building blocks |
| US8966854B2 (en) * | 2010-09-13 | 2015-03-03 | Xian Li | Modular construction system, element and assembly method thereof |
| US9021762B1 (en) * | 2014-02-06 | 2015-05-05 | Frank DePalma | Interlocking concrete blocks with trapezoidal shape |
| JP6399285B2 (ja) * | 2014-03-28 | 2018-10-03 | セイコーエプソン株式会社 | 液体噴射装置及び液体噴射ヘッドユニット |
| US9677267B2 (en) | 2014-10-15 | 2017-06-13 | Block Florida, LLC | Construction blocks and systems |
| US9074362B1 (en) * | 2014-10-15 | 2015-07-07 | Block Florida, LLC | Construction blocks and systems |
| US9133619B1 (en) * | 2014-11-20 | 2015-09-15 | Spherical Block LLC | Architectural building block |
| DE102016108951A1 (de) * | 2016-05-13 | 2017-11-16 | Jörg Kreisel | Raumkörper |
| USD829933S1 (en) * | 2016-11-30 | 2018-10-02 | Dryvit Systems, Inc. | Brick |
| USD826771S1 (en) * | 2016-12-19 | 2018-08-28 | Kelly Ellingson | Belt clip |
| JP1628988S (de) * | 2018-04-03 | 2019-04-08 | ||
| USD912638S1 (en) * | 2019-03-06 | 2021-03-09 | Shenzhen Radiant Technology Co., Ltd | Display screen |
| AU2019246777A1 (en) * | 2019-10-08 | 2021-04-22 | Shaw, Michael Adrian MR | Modelmaking System for Designing Buildings |
| USD906436S1 (en) * | 2019-12-10 | 2020-12-29 | Trimino World Technology, Inc. | Game pieces |
| USD1015435S1 (en) * | 2021-10-13 | 2024-02-20 | National Central University | Game piece set |
| US11638884B1 (en) * | 2021-10-28 | 2023-05-02 | Zhejiang Benlai Household Technology Co., Ltd. | Basic connecting block and connecting block group |
| USD991618S1 (en) * | 2022-11-03 | 2023-07-04 | Elijah David Hankins | Elastane cadaver cover |
| USD1019786S1 (en) * | 2023-12-07 | 2024-03-26 | Shenzhen Dikemeng Technology Industrial Co., Ltd. | Tetra tower game set |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US741949A (en) * | 1903-06-10 | 1903-10-20 | Elizabeth Harrison | Kindergarten building-blocks. |
| GB101420A (de) * | 1915-09-08 | Rabut Charles | ||
| US2131349A (en) * | 1937-03-27 | 1938-09-27 | Jr Gideon R Kreider | Toy block |
| US2861388A (en) * | 1951-08-14 | 1958-11-25 | Favaretto Gianni | Structural toy and model building set |
| NL135744C (de) * | 1966-08-19 | |||
| US3577672A (en) * | 1967-09-01 | 1971-05-04 | William Nutting | Modular rigid block-type dollhouse construction toy |
| US3449857A (en) * | 1967-11-14 | 1969-06-17 | Blackstone Corp | Modular blocks with mating channel structure |
| DE1965417A1 (de) * | 1969-01-02 | 1970-07-16 | Peter Croy | Bauelement |
| US3564787A (en) * | 1969-12-03 | 1971-02-23 | Raymond Sherman | Modular design block |
| US3660928A (en) * | 1970-08-28 | 1972-05-09 | Jorge Picazo Michel | Modular building blocks with interfitting grooved surfaces |
-
0
- BE BE792683D patent/BE792683A/xx unknown
-
1971
- 1971-12-13 DK DK606771AA patent/DK127955B/da unknown
-
1972
- 1972-12-07 NL NL7216579A patent/NL7216579A/xx unknown
- 1972-12-08 DE DE2260228A patent/DE2260228A1/de active Pending
- 1972-12-11 IE IE1723/72A patent/IE37207B1/xx unknown
- 1972-12-11 NO NO4571/72A patent/NO132616C/no unknown
- 1972-12-12 CH CH1802372A patent/CH559567A5/xx not_active IP Right Cessation
- 1972-12-12 AU AU49958/72A patent/AU470389B2/en not_active Expired
- 1972-12-12 FR FR7244173A patent/FR2170436A5/fr not_active Expired
- 1972-12-12 US US00314459A patent/US3822569A/en not_active Expired - Lifetime
- 1972-12-12 AT AT1053772A patent/AT332766B/de not_active IP Right Cessation
- 1972-12-13 CA CA158,729A patent/CA963657A/en not_active Expired
- 1972-12-13 JP JP47126344A patent/JPS4865039A/ja active Pending
- 1972-12-13 IT IT32801/72A patent/IT971777B/it active
- 1972-12-13 GB GB5754772A patent/GB1377239A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE792683A (fr) | 1973-03-30 |
| ATA1053772A (de) | 1976-01-15 |
| DE2260228A1 (de) | 1973-06-28 |
| NL7216579A (de) | 1973-06-15 |
| IE37207B1 (en) | 1977-05-25 |
| FR2170436A5 (de) | 1973-09-14 |
| JPS4865039A (de) | 1973-09-07 |
| AT332766B (de) | 1976-10-11 |
| IE37207L (en) | 1973-06-13 |
| AU470389B2 (en) | 1976-03-11 |
| IT971777B (it) | 1974-05-10 |
| GB1377239A (en) | 1974-12-11 |
| NO132616C (de) | 1975-12-10 |
| DK127955B (da) | 1974-02-11 |
| AU4995872A (en) | 1974-06-13 |
| US3822569A (en) | 1974-07-09 |
| CA963657A (en) | 1975-03-04 |
| CH559567A5 (de) | 1975-03-14 |
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