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
Norwegian (no)
Other versions
NO134889C (en
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 NO1709/68A priority patent/NO134891C/no
Priority to NO1711/68A priority patent/NO134893C/no
Priority to NO1710/68A priority patent/NO134892C/no
Priority to NO5180/69A priority patent/NO134894C/no
Priority to NO5184/69A priority patent/NO134240C/no
Priority to NO5183/69A priority patent/NO134896C/no
Priority to NO5181/69A priority patent/NO134895C/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
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    • 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
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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
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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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    • C07D307/02—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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    • C07D307/36—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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    • C07D307/78—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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    • C07D307/79—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
    • 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. Process for the production of acrylonitrile.

Foreliggende oppfinnelse vedrører en The present invention relates to a

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. method for the production of acrylonitrile. More specifically, the invention concerns the production of acrylonitrile by a method which comprises a catalytic vapor-phase reaction of ammonia, oxygen and propylene in the presence of a small amount of added hydrogen cyanide.

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. The literature contains many works relating to the production of acrylonitrile, but most of these works relate to methods where hydrogen cyanide and acetylene are used as starting reactants. The present invention, on the other hand, differs from the latter type of method in that it relates to an improvement of a method of the type described in US Patent No. 2,481,826 and No. 2,904,580 and British Patent No. 723,003 .

I henhold til de nevnte patenter kan According to the aforementioned patents can

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- acrylonitrile is produced with good yields by allowing a mixture of propylene, oxygen and ammonia to react in the vapor phase at elevated temperature in the presence of a catalyst. A number of catalysts are mentioned in the aforementioned patents as being suitable for the method, e.g. bismuth, tin and antimony salts of phosphomolybdic acids and molybdic acids and bismuth phosphortungstate, and of these bismuth phosphormolybdate is listed as the preferred catalyst in US patent no. 2 904 580. The reaction is carried out at a temperature in the range of 250-600° C, and generally a temperature in the range from approx. 425 to 510° C. The latter US patent discloses certain operational

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. ranges for the molar ratio between the reacting substances and these are: oxygen-propylene — 0.5 : 1 to 3 : 1 ammonia-propylene — 0.5 : 1 to 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. The patent also reveals that in some cases beneficial effects are achieved by adding water to the reaction mixture. Various other working conditions for carrying out the reaction are also obvious in the patent.

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. One of the by-products of the process described in the aforementioned patents is hydrogen cyanide. The amount of hydrogen cyanide that is formed is not sufficiently large, in relation to the amount of acrylonitrile produced, to justify the installation of aids for the recovery of the hydrogen cyanide, and even if it can be easily disposed of by burning, this work step has a adverse effect on the total economy of the procedure. In accordance with the foregoing, an object of the invention is to provide a method for the production of acrylonitrile from propylene which will reduce the formation of hydrogen cyanide as a by-product in the reaction.

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. It has been discovered that if hydrogen cyanide is added to the feed to the reaction vessel in certain quantities, which will be specified in more detail below, then the total amount of hydrogen cyanide formed in the reaction vessel will be substantially reduced, if not completely eliminated. In accordance with the foregoing, the invention is briefly based on a method for the production of acrylonitrile which comprises a catalytic vapor phase reaction of propylene, oxygen, air and ammonia in the presence of hydrogen cyanide.

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. In general, a sufficient amount of hydrogen cyanide should be present in the feed to the process to provide a hydrogen cyanide/propylene ratio in the range of 0.01:1 to 0.2:1. A preferred ratio of hydrogen cyanide to propylene is 0.1: 1 and this ratio seems to give the best results.

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. In practice, the procedure is carried out in the following way. A mixture of propylene, oxygen and ammonia in a certain predetermined ratio is introduced into a catalytic reactor together with a certain amount of hydrogen cyanide. In the product recovery step, hydrogen cyanide is separated from the other products from the reaction and recirculated to the reactor so that a very small, if any, net production of hydrogen cyanide takes place in the process.

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. More specifically, product recovery is carried out by directing what flows out of the reaction, including hydrogen cyanide, to an absorption device, where the reaction products are taken up in a solvent. Enriched solvent from the absorption device containing hydrogen cyanide as well as the other products from the reaction is then subjected to fractionation, e.g. by distillation, whereby a relatively pure stream of hydrogen cyanide is obtained. Part of this flow is circulated to a point where it can be combined with the fresh feed to the reaction vessel. As a small amount of hydrogen cyanide can be formed in accordance with the method according to the invention, provision must be made for a continuous removal of excess hydrogen cyanide from the recirculation stream in order to prevent the accumulation of hydrogen cyanide in the system.

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. Everyone. The experiments described below were carried out in a carbon jet reactor using a fluidized catalyst. A catalyst comprising 50% bismuth phosphormolybdate and 50% silicic acid was used in all experiments. In the data listed below, the following definition was used.

Oppfinnelsen vil forståes bedre ved henvisning til- følgende eksempel som viser en foretrukken utførelsesform av oppfinnelsen. The invention will be better understood by reference to the following example which shows a preferred embodiment of the invention.

Eksempel 1. Example 1.

Ved dette forsøk hadde tilmatningen til reaktoren følgende sammensetning: In this experiment, the feed to the reactor had the following composition:

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 : The reactor was operated at a pressure of 0.91 fcg/cm 2 and a temperature of 455°C with a VT of 0.029. The experiment was carried out for 8y2 hours. Analysis of the products showed the following transformations:

Forskjellige andre produkter, som carbon-dioxyd og carbonmonoxyd, dannes også ved denne reaksjon, men de er ikke noe viktige ved denne oppfinnelse. Various other products, such as carbon dioxide and carbon monoxide, are also formed by this reaction, but they are not important in this invention.

Eksempel 2. Example 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: In another experiment which was carried out to show the effect achieved in the absence of hydrogen cyanide, the feed to the reactor had the following composition:

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: During this experiment, the reactor was operated at a pressure of 0.91 feg/cm 2 and a temperature of 455°C with a VT of 0.028. The pre-search was carried out for 1 11.1 hours. Analysis of the products showed the following transformations:

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. A comparison of these results with the results obtained in example 1 shows that three times as much hydrogen cyanide is formed when hydrogen cyanide is not present in the feed. Even more surprising is the reduction in the amount of acetonitrile formed when hydrogen cyanide is present in the feed.

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. In general, one can predict with the help of the mass conservation equation that recirculation of one of the reaction products to the feed to the reaction will result in a decrease in the formation of the recycled product. Although this law is exceptionally important in a simple chemical reaction, it cannot be generally applied to a heterogeneous catalytic system. In the latter case, the effect of recycling some of the products cannot be predicted and this is particularly the case with the present method. For example the recycling of acetonitrile, which is another by-product of the process, resulted in an increase in the formation of acetonitrile and this result is shown by example 3 as follows: Example 3.

Ved dette forsøk hadde tilmatningen til reaktoren følgende sammensetning: In this experiment, the feed to the reactor had the following composition:

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: During this experiment, the reactor was operated at a pressure of 0.91 kg/cm2 and at a temperature of 455°C with a VT of 0.029. The experiment was carried out for 17.7 hours. Analysis of the products showed the following transformations:

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. The increase in the amount of acetonitrile obtained in this experiment clearly shows that it is impossible to predict the effect that the recycling of any of the products will have on the reaction.

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.1. Process for producing acrylonitrile by allowing a mixture of propylene, ammonia and oxygen to react in the vapor phase in the presence of a catalyst, characterized in that hydrogen cyanide in an amount of 0.01 to 0.2 mol, preferably 0, 1 mole per moles of propylene, is added to the reaction mixture. 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.2. Method as stated in claim 1, characterized in that any hydrogen cyanide present in the reaction product is separated and at least part of said separated hydrogen cyanide is recycled to the reaction zone.
NO162820A 1965-04-30 1966-04-29 NO134889C (en)

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