NO762204L - - Google Patents
Info
- Publication number
- NO762204L NO762204L NO762204A NO762204A NO762204L NO 762204 L NO762204 L NO 762204L NO 762204 A NO762204 A NO 762204A NO 762204 A NO762204 A NO 762204A NO 762204 L NO762204 L NO 762204L
- Authority
- NO
- Norway
- Prior art keywords
- stated
- butyne
- added
- acetylene
- propyne
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 24
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 150000002500 ions Chemical class 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 12
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 11
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- -1 mercury ions Chemical class 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims description 6
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 2
- 229920000178 Acrylic resin Polymers 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 2
- 235000013824 polyphenols Nutrition 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000004317 sodium nitrate Substances 0.000 claims description 2
- 235000010344 sodium nitrate Nutrition 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical compound [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 claims 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-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
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 229910001987 mercury nitrate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
- C07C41/08—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only to carbon-to-carbon triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
"Fremgangsmåte for addisjon av alkoholer til acetylenforbindelser". "Procedure for the Addition of Alcohols to Acetylene Compounds".
Foreliggende oppfinnelse vedrorer en fremgangsmåte for addisjon alkoholer til acetylenforbindelser som inneholdes i organiske eller uorganiske hydrokarbonstrommer. The present invention relates to a method for adding alcohols to acetylene compounds contained in organic or inorganic hydrocarbon streams.
Mer spesielt vedrorer den foreliggende oppfinnelse en fremgangsmåte som tillater rensing av både organiske eller uorganiske hydrokarbonstrommer, og at de samme acetylenforbindelser kan anvendes samtidig for fremstilling av industrielt interessante produkter. More particularly, the present invention relates to a method which allows the purification of both organic and inorganic hydrocarbon streams, and that the same acetylene compounds can be used at the same time for the production of industrially interesting products.
Oppfinnelsen vedrorer således en fremgangsmåte for:The invention thus relates to a method for:
1. Fjernelse fra en hydrokarbonstrom omfattende etylen, propylen og butylen, enten alene eller i blanding med andre mettede eller umettede hydrokarboner med samme antall karbonatomer, av acetylen, propyn, 1-butyn, 2-butyn, vinylacetylen og diacetylen med samtidig fremstilling av etyletere og/eller av gem-dieterne av de samme forbindelser. 2. For fjernelse fra butadienstrbmmer (enten alene eller i blanding med mettede eller umettede hydrokarboner med samme antall karbonatomer) av propyn, 1-butyn, 2-butyn, vinylacetylen og/eller diacetylen, med samtidig fremstilling av vinyleterne og/eller gem-dieterne av de samme forbindelser. 3. For fjernelse fra propylenstrommer (enten alene eller i blanding med andre mettede eller umettede hydrokarboner med samme antall karbonatomer) av propynet, med samtidig fremstilling av den tilsvarende vinyleter og/eller gem-dieter. 4. For fjernelse fra etylenstrommer (enten alene eller i blanding med etan) av acetylenet med samtidig fremstilling av tilsvarende vinyleter og/eller gem-dieter. 1. Removal from a hydrocarbon stream comprising ethylene, propylene and butylene, either alone or in admixture with other saturated or unsaturated hydrocarbons with the same number of carbon atoms, of acetylene, propyne, 1-butyne, 2-butyne, vinylacetylene and diacetylene with simultaneous production of ethyl ethers and/or of the gem-dieters of the same compounds. 2. For the removal from butadiene groups (either alone or in a mixture with saturated or unsaturated hydrocarbons with the same number of carbon atoms) of propyne, 1-butyne, 2-butyne, vinylacetylene and/or diacetylene, with simultaneous production of the vinylethers and/or gem-diethers of the same compounds. 3. For the removal from propylene drums (either alone or in a mixture with other saturated or unsaturated hydrocarbons with the same number of carbon atoms) of propyne, with simultaneous production of the corresponding vinyl ether and/or gem-diet. 4. For the removal from ethylene streams (either alone or in a mixture with ethane) of the acetylene with simultaneous production of the corresponding vinyl ether and/or gem-diet.
Det er kjent at for de fleste anvendelser må de olefiniske, mettede og spesielt de dieniske hydrokarboner være fri for acetylenforbindelser, f.eks. må deres innhold i butadien-monomer være 50 ppm på grunn av deres giftvirkning på poly-merisasjonskatalysatorene. It is known that for most applications the olefinic, saturated and especially the dienic hydrocarbons must be free of acetylene compounds, e.g. their content in butadiene monomer must be 50 ppm due to their toxic effect on the polymerization catalysts.
Et antall fremgangsmåter er foreslått og anvendes faktisk for fjernelse av acetylenforbindelsene og disse metoder tillater opp-nåelse av det onskede acetyleninnhold, men krever store drifts-utgifter og/eller spesielt utstyr og således hoye innvesterings-omko s tn i nger. A number of methods have been proposed and are actually used for the removal of the acetylene compounds and these methods allow the desired acetylene content to be achieved, but require large operating expenses and/or special equipment and thus high investment costs.
Det er funnet at acetylenforbindelsene kan fjernes fullstendig uten å anvende operasjoner av tidligere kjent type, idet betraktelige okonomiske fordeler samtidig oppnås både på grunn av enkelheten av operasjonene foreslått til erstatning for den som i dag anvendes, og for samtidig bruk av acetylenforbindelsene i It has been found that the acetylene compounds can be completely removed without using operations of a previously known type, considerable economic advantages being simultaneously achieved both due to the simplicity of the operations proposed to replace the one currently used, and for the simultaneous use of the acetylene compounds in
(de strommer som er rike på disse forbindelser bortskaffes i dag vanlig ved flammebrenning) ved deres omdannelse til industrielt interessante forbindelser. (those streams rich in these compounds are today usually disposed of by incineration) by their conversion into industrially interesting compounds.
Formålet for den foreliggende oppfinnelse er en fremgangsmåte som går ut på selektiv addisjon til disse acetylenforbindelser av en alkohol, spesielt foretrukket metanol, eller av en glykol, spesielt og foretrukket etylenglykol, i nærvær av en sur ionevekslerharpiks hvor de aktive punkter er totalt utbyttet med mercuri-ioner (Hg<++->ioner) og ioner av alkali eller jordalkali-metaller (Me<n+->ioner). The purpose of the present invention is a method which consists in the selective addition to these acetylene compounds of an alcohol, especially preferably methanol, or of a glycol, especially and preferably ethylene glycol, in the presence of an acidic ion exchange resin where the active points are completely replaced with mercury -ions (Hg<++->ions) and ions of alkali or alkaline earth metals (Me<n+->ions).
De resulterende produkter fjernes deretter og isoleres vedThe resulting products are then removed and isolated by
enkle og okonomiske destillasjonsoperasjoner.simple and economical distillation operations.
Den anvendte ionevekslerharpiks har som ovenfor angitt sure egenskaper og inneholder foretrukket sulfonsyregrupper (SO^H-grupper understottet på harpikser, f.eks. polystyren, divinyl benzen eller polyfenolharpikser) men harpikser som inneholder COOH-grupper, foretrukket understottet på acrylharpikser kan også anvendes. As indicated above, the ion exchange resin used has acidic properties and preferably contains sulphonic acid groups (SO^H groups supported on resins, e.g. polystyrene, divinyl benzene or polyphenol resins) but resins containing COOH groups, preferably supported on acrylic resins can also be used.
Generelt kan ionene av de ovennevnte metaller tilsettes harpiksene i form av deres salter, f.eks. som mercuri- og natrium-nitrat eller acetat, men for dette formål kan hydroksydene også anvendes (f.eks. kan natrium adderes i hydrooksydform). Innholdet av Hg<++->ioner i harpiksen kan også være hoyere enn for Me -ionene. In general, the ions of the above-mentioned metals can be added to the resins in the form of their salts, e.g. such as mercury and sodium nitrate or acetate, but for this purpose the hydroxides can also be used (eg sodium can be added in hydroxide form). The content of Hg<++> ions in the resin can also be higher than for the Me ions.
Det foretrekkes at forst Me<n+>ionene og deretter Hg<++->ionene adderes til harpiksene og det foretrekkes også at under opera-sjonen anvendes det vandige losninger og at harpiksen etter behandling dehydratiseres ved vasking med etanol eller generelt med den alkohol som anvendes ved reaksjonen. It is preferred that first the Me<n+> ions and then the Hg<++> ions are added to the resins and it is also preferred that during the operation aqueous solutions are used and that the resin is dehydrated after treatment by washing with ethanol or generally with the alcohol that used in the reaction.
De hydrokarbonstrommer som kan behandles ved fremgangsmåten i henhold til oppfinnelsen er parafiniske, olefiniske og dieniske strommer (spesielt strommer rike på etylen, propylen og butadien). The hydrocarbon streams that can be treated by the method according to the invention are paraffinic, olefinic and diene streams (especially streams rich in ethylene, propylene and butadiene).
Addisjonen kan gjennomfores innen vide grenser for temperatur og trykk og behandlingen gjennomfores foretrukket mellom -20 The addition can be carried out within wide limits of temperature and pressure and the treatment is preferably carried out between -20
og +80°C og mer passende mellom 10°C og 50°C, under trykk valgt slik at det ved arbeidstemperaturen opprettholdes hydrokarbonstrommer som behandles enten i flytende eller gass-formet fase (avhengig av hensiktsmessigheten ved å behandle disse strommer i damp- eller væske-fase. Ved å arbeide i væskefase er volumhastigheten (LHSV) for reaksjonen mellom 0.1 and +80°C and more suitably between 10°C and 50°C, under pressure selected so as to maintain at the working temperature hydrocarbon streams which are treated either in liquid or gaseous phase (depending on the expediency of treating these streams in vapor or liquid phase By working in the liquid phase, the volume velocity (LHSV) of the reaction is between 0.1
og 100 (cm 2/h.g). Det er tilrådelig å gjennomfore behandlingen i nærvær av et stokiometrisk overskudd av alkoholen eller glykolen i forhold til acetylenforbindelsene og et molforhol (alkohol/totale acetylenforbindelser) på 1,05 - 2,1 er særlig egnet, spesielt avhengig av om det onskes vinyletere eller gem-dietere. and 100 (cm 2 /h.g). It is advisable to carry out the treatment in the presence of a stoichiometric excess of the alcohol or glycol in relation to the acetylene compounds and a molar ratio (alcohol/total acetylene compounds) of 1.05 - 2.1 is particularly suitable, especially depending on whether vinyl ethers or gem - dieters.
Det er av betydning å påpeke at ved å arbeide i henhold tilIt is important to point out that by working according to
den foreliggende oppfinnelse vil harpiksene som er totalt utvekslet med mercuriioner så vel som med ioner av alkali og the present invention will the resins which are totally exchanged with mercurial ions as well as with ions of alkali and
jordalkalimetaller bibeholde sin aktivitet for et tidsrom som er minst 3 ganger så langt som for harpiksene uten ioner av alkali- jordalkalimetaller. Dette skyddes antagelig det forhold at i tilfellet med harpikser behandlet i henhold til oppfinnelsen er de sekundære reaksjoner som vanlig opptrer i nærvær av sure ionevekslerharpikser av mindre betydning. alkaline earth metals retain their activity for a period of time that is at least 3 times as long as for the resins without ions of alkali alkaline earth metals. This is presumably protected by the fact that in the case of resins treated according to the invention, the secondary reactions which usually occur in the presence of acidic ion exchange resins are of minor importance.
Enkelte utforelseeksempler gis i det folgende for bedre å illustrere oppfinnelsen. Certain exemplary embodiments are given in the following to better illustrate the invention.
EKSEMPEL_1EXAMPLE_1
98 g sur harpiks av typen "Amberlyst 15" inneholdende sure grupper som f.eks. av SO^H typen)behandles med 2 liter av 10 vektprosent vandig-jlosning av NaOH. Blandingen omrores i 1 time og filtreres og harpiksen vaskes med destillert vann inn-til det oppnås en noytral reaksjon. Den samme harpiks behandles deretter med 300 ml av en vandig losning, gjort sur ved hjelp av eddiksyre, inneholdende 2 g-ioner av Hg<++>(som mercuriacetat). Blandingen holdes omrort i 24 timer og filtreres så under vakuum og vaskes gjentatte ganger med vann-fri metanol. 98 g of acidic resin of the type "Amberlyst 15" containing acidic groups such as of the SO^H type) is treated with 2 liters of a 10% by weight aqueous solution of NaOH. The mixture is stirred for 1 hour and filtered and the resin is washed with distilled water until a neutral reaction is achieved. The same resin is then treated with 300 ml of an aqueous solution, acidified with acetic acid, containing 2 g ions of Hg<++> (as mercuric acetate). The mixture is stirred for 24 hours and then filtered under vacuum and washed repeatedly with anhydrous methanol.
En.del av den således behandlede harpiks innfylles i enA part of the thus treated resin is filled into a
reaktor med volum 10 ml og holdes ved 40°C ved hjelp av en termostatkrets. Under et trykk på 10 atmosfærer relativt trykk innfores kontinuerlig ved hjelp av en pumpe 50 ml av en strom, rik på butadien (omtrent 55%) og inneholdende omtrent 4300 ppm vinylacetylen, omtrent 1500 ppm 1-butyn og omtrent 1000 ppm propyn, sammen med metanol i en mengde slik at forholdet alkohol/total acetylenforbindelser er 2,1 mol/mol. reactor with a volume of 10 ml and is kept at 40°C by means of a thermostatic circuit. Under a pressure of 10 atmospheres relative pressure, 50 ml of a stream, rich in butadiene (about 55%) and containing about 4300 ppm vinylacetylene, about 1500 ppm 1-butyne and about 1000 ppm propyne, are introduced continuously by means of a pump, together with methanol in an amount such that the ratio alcohol/total acetylene compounds is 2.1 mol/mol.
Innholdet av alle de tre.nevnte acetylenforbindelser bestemmesThe content of all three mentioned acetylene compounds is determined
i provene av væskeutstromningen fra reaktoren (prove tas hver 5 timer) og er alltid ■^^10 ppm under hele tiden for forsoket (120 timer). in the sample of the liquid outflow from the reactor (samples are taken every 5 hours) and is always ■^^10 ppm during the entire time of the experiment (120 hours).
EKSEMPEL_2EXAMPLE_2
I den samme reaktor som i eksempel 1, ved å arbeide ved en temperatur på 80°C og under et trykk på omtrent 20 atmosfærer relativt trykk, innfores 50 ml/h propylen, inneholdende 0,3% In the same reactor as in example 1, by working at a temperature of 80°C and under a pressure of approximately 20 atmospheres relative pressure, 50 ml/h of propylene, containing 0.3%
propyn ved hjelp av en pumpe sammen med metanol i en mengde slik at forholdet alkohol/acetylenforbindelse er1.1 mol/mol. Innholdet av propyn og 2,2-dimetoksypropan, bestemt i provene fra væsken tatt hver 5 time fra reaktorutstromningen under tiden for forsoket (300 timer) er 10 ppm henholdsvis 0,78 vektprosent. propyne by means of a pump together with methanol in an amount such that the ratio alcohol/acetylene compound is 1.1 mol/mol. The content of propyne and 2,2-dimethoxypropane, determined in the sample from the liquid taken every 5 hours from the reactor effluent during the time of the trial (300 hours) is 10 ppm and 0.78 percent by weight respectively.
Claims (12)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25170/75A IT1039739B (en) | 1975-07-08 | 1975-07-08 | PROCEDURE FOR THE ADDITION OF ALCOHOLS TO ACETYLENE COMPOUNDS CONTAINED IN ORGANIC OR INORGANIC HYDROCARBON CURRENTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762204L true NO762204L (en) | 1977-01-11 |
Family
ID=11215900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762204A NO762204L (en) | 1975-07-08 | 1976-06-25 |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS602286B2 (en) |
| AR (1) | AR217057A1 (en) |
| AT (1) | AT345262B (en) |
| AU (1) | AU501768B2 (en) |
| BE (1) | BE843916A (en) |
| BR (1) | BR7605718A (en) |
| CA (1) | CA1075721A (en) |
| CH (1) | CH626266A5 (en) |
| CS (1) | CS194769B2 (en) |
| DD (2) | DD127082A5 (en) |
| DE (1) | DE2630769C3 (en) |
| DK (1) | DK303676A (en) |
| EG (1) | EG12170A (en) |
| ES (1) | ES449923A1 (en) |
| FR (1) | FR2317265A1 (en) |
| GB (1) | GB1519714A (en) |
| HU (1) | HU178721B (en) |
| IE (1) | IE43609B1 (en) |
| IN (1) | IN145252B (en) |
| IT (1) | IT1039739B (en) |
| LU (1) | LU75304A1 (en) |
| MX (1) | MX142865A (en) |
| NL (1) | NL7607524A (en) |
| NO (1) | NO762204L (en) |
| PH (1) | PH15669A (en) |
| PL (1) | PL108186B1 (en) |
| PT (1) | PT65330B (en) |
| RO (1) | RO70953A (en) |
| SE (1) | SE7607852L (en) |
| SU (1) | SU991943A3 (en) |
| TR (1) | TR18958A (en) |
| YU (1) | YU37303B (en) |
| ZA (1) | ZA763797B (en) |
| ZM (2) | ZM8876A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3700605A1 (en) * | 1987-01-10 | 1988-07-21 | Huels Chemische Werke Ag | METHOD FOR PRODUCING ALKOXIBUTENINES |
| GB9314514D0 (en) * | 1993-07-13 | 1993-08-25 | Ici Plc | Hydrocarbon processing |
| KR102561860B1 (en) * | 2016-10-25 | 2023-08-02 | 삼성전자주식회사 | Electronic apparatus and control method thereof |
-
1975
- 1975-07-08 IT IT25170/75A patent/IT1039739B/en active
-
1976
- 1976-06-25 NO NO762204A patent/NO762204L/no unknown
- 1976-06-25 ZA ZA763797A patent/ZA763797B/en unknown
- 1976-06-30 YU YU1611/76A patent/YU37303B/en unknown
- 1976-06-30 AU AU15433/76A patent/AU501768B2/en not_active Expired
- 1976-07-01 ZM ZM88/76A patent/ZM8876A1/en unknown
- 1976-07-01 ZM ZM89/76A patent/ZM8976A1/en unknown
- 1976-07-05 DK DK303676A patent/DK303676A/en not_active Application Discontinuation
- 1976-07-06 EG EG406/76A patent/EG12170A/en active
- 1976-07-06 TR TR18958A patent/TR18958A/en unknown
- 1976-07-06 ES ES449923A patent/ES449923A1/en not_active Expired
- 1976-07-06 CS CS764465A patent/CS194769B2/en unknown
- 1976-07-06 DD DD193731A patent/DD127082A5/xx unknown
- 1976-07-06 LU LU75304A patent/LU75304A1/xx unknown
- 1976-07-06 DD DD7600200187A patent/DD131012A5/en unknown
- 1976-07-06 GB GB28109/76A patent/GB1519714A/en not_active Expired
- 1976-07-06 IN IN1195/CAL/1976A patent/IN145252B/en unknown
- 1976-07-07 CH CH872876A patent/CH626266A5/en not_active IP Right Cessation
- 1976-07-07 HU HU76SA2942A patent/HU178721B/en unknown
- 1976-07-07 RO RO7686863A patent/RO70953A/en unknown
- 1976-07-07 NL NL7607524A patent/NL7607524A/en not_active Application Discontinuation
- 1976-07-07 PT PT65330A patent/PT65330B/en unknown
- 1976-07-07 AT AT498676A patent/AT345262B/en not_active IP Right Cessation
- 1976-07-07 IE IE1501/76A patent/IE43609B1/en unknown
- 1976-07-07 FR FR7620819A patent/FR2317265A1/en active Granted
- 1976-07-07 CA CA256,494A patent/CA1075721A/en not_active Expired
- 1976-07-08 MX MX165436A patent/MX142865A/en unknown
- 1976-07-08 BR BR7605718A patent/BR7605718A/en unknown
- 1976-07-08 AR AR263906A patent/AR217057A1/en active
- 1976-07-08 PL PL1976191024A patent/PL108186B1/en unknown
- 1976-07-08 SE SE7607852A patent/SE7607852L/en not_active Application Discontinuation
- 1976-07-08 PH PH18662A patent/PH15669A/en unknown
- 1976-07-08 JP JP51080430A patent/JPS602286B2/en not_active Expired
- 1976-07-08 DE DE2630769A patent/DE2630769C3/en not_active Expired
- 1976-07-08 SU SU762379661A patent/SU991943A3/en active
- 1976-07-08 BE BE168743A patent/BE843916A/en not_active IP Right Cessation
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