NO157652B - Fremgangsmte for fremstilling av 3-pikolin. - Google Patents
Fremgangsmte for fremstilling av 3-pikolin. Download PDFInfo
- Publication number
- NO157652B NO157652B NO811751A NO811751A NO157652B NO 157652 B NO157652 B NO 157652B NO 811751 A NO811751 A NO 811751A NO 811751 A NO811751 A NO 811751A NO 157652 B NO157652 B NO 157652B
- Authority
- NO
- Norway
- Prior art keywords
- dithionite
- particles
- aldehyde
- propionaldehyde
- moisture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 5
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 26
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 16
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- -1 aldehyde compound Chemical class 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract description 6
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Fremgangsmåte for fremstilling av 3-pikolin ut fra en blanding av acetaldehyd og/eller krotonaldehyd, samt formaldehyd i flytende fase ved temperaturer på 180-280°C, i lukket kar, i nærvær av ammoniumsalter.
Description
Tørrstabiliserte ditionitt-sammensetninger, samt fremgangsmåte til deres fremstilling.
Foreliggende oppfinnelse angår tørre ditionitt-sammensetninger med nedsatt tendens til dekomponering under innflytelse av fuktighet og luft.
Natriumditionitt, ofte kalt natrium-hydrosulfitt og nærstående forbindelser er ganske stabile under lagring hvis de pak-kes i lukkede beholdere, men hvis de kom-mer i kontakt med luft og fuktighet, vil man få dekomponering.
En rekke forbindelser har vært fore-slått som stabilisatorer, d.v.s. forbindelser som motvirker dekomponeringen på en eller annen måte. Således nevner US patent 1 810 663 og 2 121 397 forskjellige filmdan-nende produkter som kan brukes som et vannavstøtende «belegg» på ditionitt-partiklene. Videre foreslår britisk patent 695 375 bruk av visse flytende estere som stabilisatorer for ditionitt.
Det er en ulempe ved slike produkter at
de ikke er oppløselige eller blandbare med vann, slik at de vandige oppløsninger man fremstiller fra den ditionitt som er stabi-lisert med disse produkter ikke blir klare.
Denne ulempe har selvsagt ikke vann-oppløselige stabilisatorer, som også er kjent. Disse forbindelser må imidlertid anvendes i store mengder for å oppnå en skikkelig stabilisering. Således må man, f.eks. bruke mengder på opp til 10 % ved anvendelse av borax og paraformaldehyd ifølge US patent 2 516 321, hvor blandingen er mer ef-fektiv enn begge komponentene hver for seg, og bedre enn de alkaliske stabilisatorer som har vært brukt tidligere.
Det er en hensikt ved denne oppfinnelse å gi tørrstabiliserte ditionitt-sammensetninger som opphever de ovennevnte ulemper. Mer spesifikt er det en hensikt ved denne oppfinnelse å lage ditionitt-sammensetninger som er stabiliserte ved relativt små mengder stabilisatorer og ikke spaltes under lagring, og hvis stabilisator ikke gir turbiditet når den stabiliserte sammensetning oppløses i vann.
Disse hensikter oppnås ved å kontakte ditionitt-sammensetninger med propionaldehyd, butyraldehyd, valeraldehyd eller benzaldehyd eller blandinger av disse.
Ifølge foreliggende oppfinnelse er det således tilveiebragt en tørr ditionitt-sammensetning med redusert tendens til dekomponering under innflytelse av fuktighet og luft, kjennetegnet ved at den som hovedbestanddel inneholder ditionitt som er kontaktet med propionaldehyd, butyraldehyd, valeraldehyd, eller benzaldehyd eller en blanding av to eller flere av de nevnte forbindelser og derved har opptatt en mengde på ikke mer enn 0.5 vektprosent aldehyd beregnet med hensyn på ditionitt.
Det er foreløpig ikke klarlagt hvorvidt stabiliseringen skyldes aldehydene i seg selv eller visse reaksjonsprodukter som dannes på overflaten av ditionitt-partiklene.
Oppfinnelsen tilveiebringer også en fremgangsmåte for å redusere tendensen hos faste partikler av ditionitt til å dekomponere under innflytelse av fuktighet og luft ved å behandle ditionitt-partiklene med en stabiliserende aldehyd-forbindelse, kjennetegnet ved at ditionitt-partiklene behandles i tørr tilstand med damper av propionaldehyd og/eller butyraldehyd ved en slik kombinasjon av trykk og temperatur at det ikke dannes noe væskefase av aldehydet. Vanligvis vil den mengde aldehyd som blir «bundet» ved behandlingen være mindre enn 0.1 vektprosent når opp-til 33 vektprosent av den behandlede sammensetning består av partikler på mindre enn 100 mikron.
For fullstendighetens skyld skal det bemerkes at det allerede var kjent at ditio-nittoppløsninger kunne stabiliseres ved å tilsette formaldehyd og acetaldehyd (se Mellor, «A Comprehensive treatise on Inorganic and Theoretical Chemistry»
(1960) vol. 10, side 172). Man kjenner også omdannelsesprodukter av ditionitter og aldehyder, spesielt for formaldehyd-sulfok-silat under navnet «Rongalit», hvis stabili-tet er bedre enn for ren ditionitt.
Imidlertid kunne ikke den stabiliserende effekt av små mengder aldehyder, slik foreliggende oppfinnelse beskriver det, ut-ledes fra dette. Denne effekt er heller overraskende fordi en behandling av fast ditionitt med formaldehyd eller acetaldehyd ikke gir stabilisering.
Oppfinnelsen vil nå bli illustrert ved følgende eksempel.
Eksempel I en vakuumtørrer som inneholdt tørre, vannfrie natriumditionitt-krystaller ble det tilsatt 800 g propionaldehyd per tonn ditionitt. Temperaturen i tørkeren var 45° C og trykket var før tilsetning 100 mm Hg. Etter at aldehyddampen hadde virket på krystallene i 10 minutter, ble overskudd av damp suget av.
Under lagring i kontakt med luft ved 30° C og en relativ fuktighet på 75 %, viste det tørre stabiliserte produkt en reduksjon på 18 % ditionitt i løpet av 24 timer, mens ustabilisert produkt under samme forhold viste en reduksjon på 38 %.
Claims (2)
1. Tørr ditionitt-sammensetning med redusert tendens til dekomponering under innflytelse av fuktighet og luft, karakterisert ved at den som hovedbestan-del inneholder ditionitt som er kontaktet med propionaldehyd, butyraldehyd, valeraldehyd, eller benzaldehyd eller en blanding av to eller flere av de nevnte forbindelser og derved har opptatt en mengde på ikke mer enn 0.5 vektprosent aldehyd beregnet med hensyn på ditionitt.
2. Fremgangsmåte for å redusere tendensen' hos faste partikler av ditionitt til å dekomponere under innflytelse av fuktighet og luft ved å behandle ditionitt-partiklene med en stabiliserende aldehyd-forbindelse, karakterisert ved at ditionitt-partiklene behandles i tørr tilstand med damper av propionaldehyd og/ eller butyraldehyd ved en slik kombinasjon av trykk og temperatur at det ikke dannes noe væskefase av aldehydet.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH405280 | 1980-05-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO811751L NO811751L (no) | 1981-11-24 |
| NO157652B true NO157652B (no) | 1988-01-18 |
| NO157652C NO157652C (no) | 1988-04-27 |
Family
ID=4268913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811751A NO157652C (no) | 1980-05-23 | 1981-05-22 | Fremgangsmaate for fremstilling av 3-pikolin. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4337342A (no) |
| EP (1) | EP0040698B1 (no) |
| JP (1) | JPS5718665A (no) |
| AR (1) | AR225813A1 (no) |
| AT (1) | ATE5719T1 (no) |
| AU (1) | AU540026B2 (no) |
| BR (1) | BR8103204A (no) |
| CA (1) | CA1128520A (no) |
| CS (1) | CS221832B2 (no) |
| DD (1) | DD159070A5 (no) |
| DE (1) | DE3161757D1 (no) |
| DK (1) | DK226881A (no) |
| ES (1) | ES501909A0 (no) |
| FI (1) | FI811546L (no) |
| GR (1) | GR81533B (no) |
| HU (1) | HU183450B (no) |
| IE (1) | IE51244B1 (no) |
| IL (1) | IL62856A (no) |
| IN (1) | IN153294B (no) |
| MX (1) | MX156300A (no) |
| NO (1) | NO157652C (no) |
| PL (1) | PL127978B1 (no) |
| RO (1) | RO82087A (no) |
| SU (1) | SU1095876A3 (no) |
| TR (1) | TR21358A (no) |
| YU (1) | YU42569B (no) |
| ZA (1) | ZA813382B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI814007L (fi) * | 1981-01-09 | 1982-07-10 | Lonza Ag | Foerfarande foer framstaellning av 3-pikolin |
| CH656879A5 (de) * | 1981-07-09 | 1986-07-31 | Lonza Ag | Verfahren zur herstellung von 3,5-dialkylpyridinen. |
| CH660733A5 (de) * | 1981-09-29 | 1987-06-15 | Lonza Ag | Verfahren zur herstellung von 3-picolin. |
| JPH03111749U (no) * | 1990-02-28 | 1991-11-15 | ||
| AU2012204141C1 (en) * | 2005-08-19 | 2015-10-22 | Houghton Technical Corp. | Methods and compositions for acid treatment of a metal surface |
| CA2618915C (en) | 2005-08-19 | 2014-09-23 | Houghton Metal Finishing Company | Methods and compositions for acid treatment of a metal surface |
| EP2277864A1 (de) * | 2009-06-24 | 2011-01-26 | Lonza Ltd. | Syntheseprozess für 3-Methylpyridin |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2769007A (en) * | 1956-10-30 | Manufacture of a pyridine homologue | ||
| GB534494A (en) * | 1939-10-06 | 1941-03-07 | Distillers Co Yeast Ltd | Improvements in or relating to the manufacture of heterocyclic bases |
| GB971174A (en) * | 1961-08-31 | 1964-09-30 | Distillers Co Yeast Ltd | Production of pyridine |
| GB1182705A (en) * | 1966-09-21 | 1970-03-04 | Lummus Co | Improvements in or relating to the Vapour Phase Production of Pyridine of Alkyl Pyridines |
| GB1208569A (en) * | 1967-01-04 | 1970-10-14 | Ici Ltd | Process for the production of pyridines |
| GB1188891A (en) * | 1968-01-27 | 1970-04-22 | Bp Chem Int Ltd | Picolines |
| US3846435A (en) * | 1972-07-21 | 1974-11-05 | Merck & Co Inc | Process for the production of 2-methyl-5-ethyl pyridine |
-
1981
- 1981-04-24 AT AT81103114T patent/ATE5719T1/de not_active IP Right Cessation
- 1981-04-24 EP EP81103114A patent/EP0040698B1/de not_active Expired
- 1981-04-24 DE DE8181103114T patent/DE3161757D1/de not_active Expired
- 1981-05-06 ES ES501909A patent/ES501909A0/es active Granted
- 1981-05-08 IE IE1025/81A patent/IE51244B1/en not_active IP Right Cessation
- 1981-05-11 AU AU70449/81A patent/AU540026B2/en not_active Ceased
- 1981-05-12 IL IL62856A patent/IL62856A/xx unknown
- 1981-05-12 US US06/263,042 patent/US4337342A/en not_active Expired - Fee Related
- 1981-05-16 IN IN524/CAL/81A patent/IN153294B/en unknown
- 1981-05-19 FI FI811546A patent/FI811546L/fi not_active Application Discontinuation
- 1981-05-20 DD DD81230129A patent/DD159070A5/de not_active IP Right Cessation
- 1981-05-20 ZA ZA00813382A patent/ZA813382B/xx unknown
- 1981-05-20 GR GR65013A patent/GR81533B/el unknown
- 1981-05-21 YU YU1308/81A patent/YU42569B/xx unknown
- 1981-05-21 CA CA377,996A patent/CA1128520A/en not_active Expired
- 1981-05-21 HU HU811482A patent/HU183450B/hu unknown
- 1981-05-22 MX MX187446A patent/MX156300A/es unknown
- 1981-05-22 AR AR285419A patent/AR225813A1/es active
- 1981-05-22 TR TR21358A patent/TR21358A/xx unknown
- 1981-05-22 JP JP7762881A patent/JPS5718665A/ja active Granted
- 1981-05-22 DK DK226881A patent/DK226881A/da not_active Application Discontinuation
- 1981-05-22 SU SU813285560A patent/SU1095876A3/ru active
- 1981-05-22 PL PL1981231300A patent/PL127978B1/pl unknown
- 1981-05-22 CS CS813818A patent/CS221832B2/cs unknown
- 1981-05-22 BR BR8103204A patent/BR8103204A/pt unknown
- 1981-05-22 NO NO811751A patent/NO157652C/no unknown
- 1981-05-23 RO RO81104387A patent/RO82087A/ro unknown
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