NO134889B - - Google Patents

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Publication number
NO134889B
NO134889B NO162820A NO16282066A NO134889B NO 134889 B NO134889 B NO 134889B NO 162820 A NO162820 A NO 162820A NO 16282066 A NO16282066 A NO 16282066A NO 134889 B NO134889 B NO 134889B
Authority
NO
Norway
Prior art keywords
hydrogen cyanide
reaction
propylene
products
reactor
Prior art date
Application number
NO162820A
Other languages
English (en)
Other versions
NO134889C (no
Inventor
M Winter
F Gautschi
I Flament
M Stoll
I M Goldman
Original Assignee
Firmenich & Cie
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich & Cie filed Critical Firmenich & Cie
Priority to NO108/68A priority Critical patent/NO134890C/no
Priority to NO1710/68A priority patent/NO134892C/no
Priority to NO1711/68A priority patent/NO134893C/no
Priority to NO1709/68A priority patent/NO134891C/no
Priority to NO5181/69A priority patent/NO134895C/no
Priority to NO5184/69A priority patent/NO134240C/no
Priority to NO5183/69A priority patent/NO134896C/no
Priority to NO5180/69A priority patent/NO134894C/no
Publication of NO134889B publication Critical patent/NO134889B/no
Publication of NO134889C publication Critical patent/NO134889C/no

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • 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
    • C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
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    • 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
    • C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
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    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • C07D307/80—Radicals substituted by oxygen atoms
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid

Description

Fremgangsmåte for fremstilling av acrylnitril.
Foreliggende oppfinnelse vedrører en
fremgangsmåte for fremstilling av acrylnitril. Mer .spesielt går oppfinnelsen ut på fremstilling av acrylnitril ved en fremgangsmåte som omfatter katalytisk damp-fasereaksjon av ammoniakk, oxygen og propylen i nærvær av en mindre mengde tilsatt hydrogencyanid.
Litteraturen inneholder mange arbeider som vedrører fremstillingen av acrylnitril, men de fleste av disse arbeider ved-rører fremgangsmåter, hvor det anvendes hydrogencyanid og acetylen som utgangs-reagerende stoffer. Foreliggende oppfinnelse atskiller seg på den annen side fra sistnevnte art av fremgangsmåte ved at den vedrører en, forbedring av en fremgangsmåte av den art som er beskrevet i US patent nr. 2 481 826 og nr. 2 904 580 og britisk patent nr. 723 003.
I henhold til de nevnte patenter kan
acrylnitril 'fremstilles med gode utbytter ved å la en blanding av propylen, oxygen og ammoniakk reagere i dampfasen ved forhøyet temperatur i nærvær av en katalysator. Et flertall katalysatorer er om-talt i de nevnte patenter som egnet for fremgangsmåten, f. eks. visinuth-, tinn- og antimonsalter av fosformolybdensyrer og molybdensyrer og vismuthfosforwolframat, og av disse er vismuthfosformolybdat an-ført som den foretrukne katalysator i US patent nr. 2 904 580. Reaksjonen utføres ved en temperatur i området av 250—600° C, og generelt foretrekkes en temperatur i området fra ca. 425 til 510° C. Det sistnevnte US patent åpenbarer visse drifts-
områder for molforholdet mellom de rea-gerende stoffer og disse er: oxygen-propylen — 0,5 : 1 til 3 : 1 ammoniakk-proplyen — 0,5 : 1 til 5 : 1.
Patentet åpenbarer også at i enkelte til-feller oppnåes det gunstige virkninger ved å tilsette vann til reaksjonsblandingen. Forskjellige andre arbeidsforhold for ut-førelse av reaksjonen er også åpenbart i patentet.
Et av biproduktene ved fremgangsmåten som er beskrevet i de nevnte patenter, er hydrogencyanid. Mengden av hydrogencyanid som dannes, er ikke tilstrekkelig stor, i forhold til mengden av fremstilt acrylnitril', til å berettige installeringen av hjelpemidler for gjenvinningen av hydrogencyanidet, og selv om det lett kan skaf-fes bort ved brenning, så har dog dette arbeidstrinin en uheldig virkning på frem-gangsmåtens totale økonomi. I overensstemmelse med det iforan anførte er et formål for oppfinnelsen å tilveiebrinige en fremgangsmåte for fremstilling av acrylnitril fra propylen som vil redusere dannelsen av hydrogencyanidet som et bipro-dukt ved reaksjonen.
Det er blitt oppdaget at hvis hydrogencyanid tilsettes til tilmatningen til reaksj omskaret i visse mengder, som skal angis nærmere i det følgende, så vil totalmeng-den av hydrogencyanidet som dannes i reaksjonskaret, bli vesentlig redusert, om ikke fullstendig eliminert. Oppfinnelsen går i overensstemmelse med det foran anførte i korthet ut på en fremgangsmåte for fremstilling av acrylnitril som omfatter en katalytisk dampfasereafcsjon av propylen, oxygen ©iler luft og ammoniakk i nærvær av hydrogencyanid.
Generelt skal det være til stede en tilstrekkelig mengde hydrogencyanid i tilmatningen til prosessen f or "å tilveiebringe et hydrogencyanid/propylenforhold i området av 0,01 : 1 til 0,2 : 1. Et foretrukket forhold av hydrogencyanid til propylen er 0,1 : 1 og dette forhold synes å gi de beste resultater.
I praksis utføres fremgangsmåten på følgende måte. En blanding av propylen, oxygen og ammoniakk i et visst forutbe-stemt forhold innføres i en katalytisk re-aktor sammen med en viss mengde av hydrogencyanid. I produktgjenvinningstrin-net utskilles hydrogencyanid fra de andre produkter fra reaksjonen og recirkuleres til reaktoren slik at det finner sted en meget liten, om overhodet noen, nettoproduk-sjon av hydrogencyanid i prosessen.
Mer spesielt utføres produktgjenvin-ningen ved å lede det som strømmer ut fra reaksjonen, innbefattet hydrogencyanid, til en absorpisj onslnnretning, hvor reaksjons-produktene opptas i' et oppløsningsmdddel. Anriket oppløsnimgsmiiddel fra absoirpsjons-innretningen som inneholder hydrogencyanid så vel som de andre produkter fra reaksjonen utsettes derpå for fraksjone-ring, f. eks. ved destillasjon, hvorved det fåes en relativt ren strøm av hydrogencyanid. En del av denne strøm sirkuleres til et punkt, hvor det kan f orenes med den friske tilmatriing til reaksjonskaret. Da en liten mengde av hydrogencyanid kan dannes i overensstemmelse med fremgangsmåten ifølge oppfinnelsen, skal det sørges for en kontinuerlig bortføring av overskudd av hydrogencyanid fra reslrkuleringsstrøm-men for å hindre oppsamlingen av hydrogencyanid' i systemet.
Alle. de 1 det følgende 'beskrevne eks-perimenter, ible utført i en carbonstråle-reaktor under anvendelse av et fluidisert katalysators] ikt. En katalysator omfat-tende 50 pst. vismuthfosformolybdat og- 50 pst. kiselsyre ble anvendt ved alle forsøk. I de nedenfor anførte dataer ble det anvendt følgende definisjon.
Oppfinnelsen vil forståes bedre ved henvisning til- følgende eksempel som viser en foretrukken utførelsesform av oppfinnelsen.
Eksempel 1.
Ved dette forsøk hadde tilmatningen til reaktoren følgende sammensetning:
Reaktoren ble drevet ved et trykk av 0,91 fcg/cm2 Oig en temperatur av 455° C med et VT av 0,029. Forsøket ble utført i 8y2 time. Analyse av produktene viste følgende omdannelser :
Forskjellige andre produkter, som carbon-dioxyd og carbonmonoxyd, dannes også ved denne reaksjon, men de er ikke noe viktige ved denne oppfinnelse.
Eksempel 2.
Ved et annet forsøk som ble utført for å vise den virkning som oppnåes' ved fra-vær av hydrogencyanid hadde tilmatningen til reaktoren følgende sammensetning:
Under dette forsøket ble reaktoren drevet ved et trykk av 0,91 feg/cm2 og en tempe-ratr av 455° C med et VT av 0,028. For-søket ble utført 1 11,1 timer. Analyse av produktene viste følgende omdannelser:
En sammenligning av disse resultater med de resultater som oppnåes i eksempel 1 viser at det dannes tre ganger så meget hydrogencyanid når hydrogencyanid ikke er til stede i tilmatningen. Endog mer over-raskende er reduksjonen i mengden av acetonitril som dannes når hydrogencyanid er til stede i tilmatningen.
I alminnelighet kan man ved hjelp av massevårkniinigsioven forutsi at recirkule-ring av et av reaksj onsproduktene til tilmatningen til reaksjonen vil resultere i en synkning i dannelsen av det resirkuler-te produkt. Selv om denne lov er usedvanlig viktig ved en enkel kjemisk reaksjon, kan den ikke generelt anvendes på et hetero-gent katalytisk system. I sistnevnte tilfelle kan virkningen av resirkulering av noen av produktene ikke forutsies og dette er særlig tilfelle ved foreliggende fremgangsmåte. F. eks. resulterte resirkulerin-gen av acetonitril, som er et annet bipro-dukt ved fremgangsmåten, 1 en økning i dannelsen av acetonitril og dette resultat er vist ved eksempel 3 som følger: Eksempel 3.
Ved dette forsøk hadde tilmatningen til reaktoren følgende sammensetning:
I løpet av dette forsøket ble reaktoren drevet ved et trykk av 0,91 kg/cm2 og ved en temperatur av 455° C med et VT av 0,029. Forsøket ble utført 1 7,7 timer. Analyse av produktene viste følgende omdannelser:
Økningen i mengden av acetonitril som fåes ved dette forsøk, viser klart at det er umulig å forutsi den effekt som recirku-leringen av noen av produktene vil ha på reaksjonen.

Claims (2)

1. Fremgangsmåte for fremstilling av acrylnitril ved at man i dampfasen lar en blanding av propylen, ammoniakk og oxygen reagere i nærvær av en katalysator, karakterisert ved at hydrogencyanid i en mengde av 0,01 til 0,2 mol, for-trinnsvis 0,1 mol pr. mol propylen, tilsettes reaksj onsblandlngen.
2. Fremgangsmåte som angitt i på-stand 1, karakterisert ved at even-tuelt i reaksj onsproduktet tilstedeværende hydrogencyanid fraskilles og i det minste en del av nevnte fraskilte hydrogencyanid resirkuleres til 'reaksjonssonen.
NO162820A 1965-04-30 1966-04-29 NO134889C (no)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NO108/68A NO134890C (no) 1965-04-30 1968-01-10
NO1710/68A NO134892C (no) 1965-04-30 1968-05-02
NO1711/68A NO134893C (no) 1965-04-30 1968-05-02
NO1709/68A NO134891C (no) 1965-04-30 1968-05-02
NO5181/69A NO134895C (no) 1965-04-30 1969-12-31
NO5184/69A NO134240C (no) 1965-04-30 1969-12-31
NO5183/69A NO134896C (no) 1965-04-30 1969-12-31
NO5180/69A NO134894C (no) 1965-04-30 1969-12-31

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US45234265A 1965-04-30 1965-04-30
US54306966A 1966-04-18 1966-04-18

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GB (1) GB1156472A (no)
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US3767429A (en) * 1971-12-06 1973-10-23 Procter & Gamble Lard flavor concentrate
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ES2104850T3 (es) * 1991-11-08 1997-10-16 Quest Int Composicion de perfume.
JP4613421B2 (ja) 1999-04-20 2011-01-19 味の素株式会社 香気前駆体組成物および香気成分発現方法
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JP5153195B2 (ja) * 2007-04-13 2013-02-27 長谷川香料株式会社 コーヒーの淹れたて感賦与剤
RU2497366C2 (ru) * 2007-11-13 2013-11-10 Нестек С.А. Применение тиоэфирных вкусоароматических добавок для улучшения вкусоароматических свойств готового к употреблению кофе после автоклавирования и хранения

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DE1793852C2 (de) 1980-10-09
DE1695505A1 (de) 1970-12-23
JPS499746B1 (no) 1974-03-06
DE1793851C2 (de) 1982-07-01
NL150316B (nl) 1976-08-16
JPS5231420B1 (no) 1977-08-15
JPS5333667B1 (no) 1978-09-16
JPS5412552B1 (no) 1979-05-23
DE1793842B1 (de) 1980-06-26
DE1793847B1 (de) 1980-06-26
ES326503A1 (es) 1967-07-01
DE1793848B1 (de) 1980-04-30
SE373735B (no) 1975-02-17
DE1793846B1 (de) 1980-04-30
JPS499747B1 (no) 1974-03-06
GB1156472A (en) 1969-06-25
SE377270B (no) 1975-06-30
DE1793844B1 (de) 1979-10-31
DE1793845C2 (de) 1980-08-07
DE1793847C3 (de) 1981-04-02
DE1793850C2 (de) 1980-12-11
SE377269B (no) 1975-06-30
DK139012B (da) 1978-12-04
SE373733B (no) 1975-02-17
NL6605854A (no) 1966-10-31
SE335463B (no) 1971-05-24
DE1793843C2 (de) 1981-01-15
SE373732B (no) 1975-02-17
DE1793852B1 (de) 1980-01-24
CH529516A (de) 1972-10-31
SE373736B (no) 1975-02-17
DE1793848C2 (de) 1981-01-15
BR6679143D0 (pt) 1973-09-11
SE373734B (no) 1975-02-17
DK139012C (no) 1979-05-14
DE1793843B1 (de) 1980-04-30
SE373731B (no) 1975-02-17
DE1793845B1 (de) 1979-10-31
DE1793844C2 (de) 1980-07-24
DE1793850B1 (de) 1980-04-24
DE1695505B2 (de) 1979-04-05
JPS4821509B1 (no) 1973-06-29
NO134889C (no) 1977-01-05
DE1695505C3 (de) 1979-11-29
DE1793842C3 (de) 1981-03-19
DE1793846C2 (de) 1981-01-15
DE1793849C2 (de) 1982-07-01

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