NO120506B - - Google Patents
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- Publication number
- NO120506B NO120506B NO168915A NO16891567A NO120506B NO 120506 B NO120506 B NO 120506B NO 168915 A NO168915 A NO 168915A NO 16891567 A NO16891567 A NO 16891567A NO 120506 B NO120506 B NO 120506B
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- amine
- nitrile
- chloro
- extracted
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 9
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000007868 Raney catalyst Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims description 2
- 238000006703 hydration reaction Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002990 phenothiazines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D47/00—Closures with filling and discharging, or with discharging, devices
- B65D47/04—Closures with discharging devices other than pumps
- B65D47/06—Closures with discharging devices other than pumps with pouring spouts or tubes; with discharge nozzles or passages
- B65D47/12—Closures with discharging devices other than pumps with pouring spouts or tubes; with discharge nozzles or passages having removable closures
- B65D47/127—Snap-on caps
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Closures For Containers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR47526A FR1493125A (fr) | 1966-07-11 | 1966-07-11 | Perfectionnements aux bouchons verseurs |
| FR69048097 | 1966-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120506B true NO120506B (de) | 1970-10-26 |
Family
ID=26235536
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO120506D NO120506L (de) | 1966-07-11 | ||
| NO168915A NO120506B (de) | 1966-07-11 | 1967-07-03 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO120506D NO120506L (de) | 1966-07-11 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3434637A (de) |
| BE (1) | BE700908A (de) |
| CH (1) | CH467203A (de) |
| DK (1) | DK128887B (de) |
| ES (1) | ES342654A1 (de) |
| FR (1) | FR1515089A (de) |
| GB (1) | GB1184478A (de) |
| NL (1) | NL146111B (de) |
| NO (2) | NO120506B (de) |
| SE (1) | SE345389B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986002334A1 (en) * | 1984-10-15 | 1986-04-24 | A/S Moss Glasva^Erk | A method in the production of containers having improved pouring properties, and a container having such properties |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128189A (en) * | 1977-04-04 | 1978-12-05 | National Plastics Corporation | Device for improving the pourability of fluids and also forming an improved closure for a container of such fluids |
| FR2505787A1 (fr) * | 1981-05-13 | 1982-11-19 | Brincourt Georges | Bouchon pour le comptage et la distribution d'objets spheriques |
| US4591078A (en) * | 1983-12-29 | 1986-05-27 | Colgate-Palmolive Company | Dripless pouring cap |
| US4696416A (en) * | 1984-09-28 | 1987-09-29 | The Procter & Gamble Company | Liquid product dispensing package with self draining feature employing drip concentrator |
| DE8521739U1 (de) * | 1985-07-27 | 1985-09-05 | Zeller Plastik Koehn, Gräbner & Co, 5583 Zell | Behälter mit auf- oder einzuprellender Kappe |
| US4706829A (en) * | 1986-02-07 | 1987-11-17 | Owens-Illinois Closure Inc. | Liquid containing and dispensing package |
| US5108009A (en) * | 1986-02-12 | 1992-04-28 | Lever Brothers Company, Division Of Conopco, Inc. | Leak and drip resistant storage dispensing and measuring package |
| DK676287A (da) * | 1987-01-22 | 1988-07-23 | Alfatechnik Ag | Plastlukke med et som laag tjenende maalebaeger |
| JPH0751481Y2 (ja) * | 1987-06-17 | 1995-11-22 | 株式会社資生堂 | 液状物容器の注出栓 |
| US5060827A (en) * | 1990-05-09 | 1991-10-29 | Colgate-Palmolive Company | Low profile anti-drip dosing cap and spout for liquid containers |
| US5181630A (en) * | 1991-06-19 | 1993-01-26 | The Procter & Gamble Company | Vessel having dual function pouring spout for spot treating or rapid transfer of viscous liquids |
| US5228596A (en) * | 1991-06-19 | 1993-07-20 | The Procter & Gamble Company | Outwardly projecting directed pour spout exhibiting thread compatible cross-sectional profile |
| FR2775956B1 (fr) * | 1998-03-16 | 2000-06-02 | John Genthon | Antigoutte a liquide a fixation exterieur |
| US6659310B1 (en) | 2000-03-14 | 2003-12-09 | The Dial Corporation | Product dispensing and drainback fitting |
| US7051892B1 (en) * | 2003-10-28 | 2006-05-30 | O'day Jr William R | Water bottle for a dispenser |
| IT1400345B1 (it) * | 2010-05-26 | 2013-05-24 | Antiche Distillerie Riunite S R L | Dispositivo versatore per bottiglie, ed apparato orientatore per impianti di tappatura |
| WO2014037825A1 (en) * | 2012-09-10 | 2014-03-13 | Guala Closures S.P.A. | Pourer with retractable spout |
| US9187219B2 (en) * | 2013-03-06 | 2015-11-17 | Westrock Slatersville, Llc | Pour lip closure with drain back |
| JP6236139B1 (ja) * | 2016-12-08 | 2017-11-22 | 藤森工業株式会社 | 詰め替え容器の注出用スパウト及び包装容器の注出ユニットとの連結構造 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2763402A (en) * | 1952-06-10 | 1956-09-18 | Livingstone Jay Gould | Adapter |
| US2763403A (en) * | 1953-06-16 | 1956-09-18 | Jay G Livingstone | Fittings |
| US3227317A (en) * | 1963-06-06 | 1966-01-04 | Shell Oil Co | Closure assembly for containers |
| US3208650A (en) * | 1963-12-30 | 1965-09-28 | Anfinsen Plastic Molding Inc | Combined flexible closure and pouring spout |
| US3307752A (en) * | 1965-03-15 | 1967-03-07 | Johnson & Son Inc S C | Captive plastic closure for container with integral container handle |
-
0
- NO NO120506D patent/NO120506L/no unknown
-
1966
- 1966-12-23 FR FR48097A patent/FR1515089A/fr not_active Expired
-
1967
- 1967-04-29 SE SE9734/67*A patent/SE345389B/xx unknown
- 1967-06-28 GB GB29841/67A patent/GB1184478A/en not_active Expired
- 1967-06-28 US US649559A patent/US3434637A/en not_active Expired - Lifetime
- 1967-06-29 CH CH935867A patent/CH467203A/fr unknown
- 1967-07-03 NL NL676709203A patent/NL146111B/xx not_active IP Right Cessation
- 1967-07-03 NO NO168915A patent/NO120506B/no unknown
- 1967-07-04 BE BE700908D patent/BE700908A/xx unknown
- 1967-07-05 ES ES342654A patent/ES342654A1/es not_active Expired
- 1967-07-10 DK DK354867AA patent/DK128887B/da unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986002334A1 (en) * | 1984-10-15 | 1986-04-24 | A/S Moss Glasva^Erk | A method in the production of containers having improved pouring properties, and a container having such properties |
Also Published As
| Publication number | Publication date |
|---|---|
| DK128887B (da) | 1974-07-22 |
| US3434637A (en) | 1969-03-25 |
| DE1607886A1 (de) | 1972-02-03 |
| ES342654A1 (es) | 1968-11-01 |
| SE345389B (de) | 1972-05-29 |
| BE700908A (de) | 1968-01-04 |
| GB1184478A (en) | 1970-03-18 |
| NO120506L (de) | |
| NL6709203A (de) | 1968-01-12 |
| FR1515089A (fr) | 1968-03-01 |
| NL146111B (nl) | 1975-06-16 |
| CH467203A (fr) | 1969-01-15 |
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