US20020004027A1 - Ammoxidation of a mixture of ketones to acetonitrile and hcn - Google Patents
Ammoxidation of a mixture of ketones to acetonitrile and hcn Download PDFInfo
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- US20020004027A1 US20020004027A1 US09/320,937 US32093799A US2002004027A1 US 20020004027 A1 US20020004027 A1 US 20020004027A1 US 32093799 A US32093799 A US 32093799A US 2002004027 A1 US2002004027 A1 US 2002004027A1
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- acetonitrile
- ketones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C3/00—Cyanogen; Compounds thereof
- C01C3/02—Preparation, separation or purification of hydrogen cyanide
- C01C3/0208—Preparation in gaseous phase
- C01C3/0212—Preparation in gaseous phase from hydrocarbons and ammonia in the presence of oxygen, e.g. the Andrussow-process
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C3/00—Cyanogen; Compounds thereof
- C01C3/02—Preparation, separation or purification of hydrogen cyanide
- C01C3/0208—Preparation in gaseous phase
- C01C3/0212—Preparation in gaseous phase from hydrocarbons and ammonia in the presence of oxygen, e.g. the Andrussow-process
- C01C3/022—Apparatus therefor
- C01C3/0225—Apparatus therefor characterised by the synthesis reactor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Definitions
- the present invention is directed to a novel process for the ammoxidation of a mixture of ketones to a mixture of nitriles.
- the present invention is directed to increasing the yield of co-product hydrogen cyanide and acetonitrile produced during the ammoxidation of propylene to acrylonitrile.
- the present invention is directed to a process which increases the yield of both main co-products (i.e. HCN and acetonitrile) during the manufacture of acrylonitrile while (1) saving on the raw material costs associated with the increase in co-product yields and (2) achieving the same or better conversion and selectivity to the desired co-products.
- main co-products i.e. HCN and acetonitrile
- ketones e.g. acetone and methyl isobutyl ketone (MIBK)
- the method of the present invention comprises introducing a hydrocarbon selected from the group consisting of propylene and propane, a mixture of ketones (e.g. acetone and MIBK), ammonia and oxygen-containing gas into reaction zone (e.g fluid bed reactor)to react in the presence of a catalyst (e.g.
- the process comprises introducing a mixture of ketones (e.g. acetone and MIBK) and/or a crude ketone, ammonia and oxygen-containing gas into reaction zone (e.g. fluid bed reactor) to react in the presence of a catalyst (e.g. fluid bed catalyst) to produce a reactor effluent comprising hydrogen cyanide and acetonitrile, passing the reactor effluent containing the hydrogen cyanide and acetonitrile into a quench column to cool the reactor effluent, and recovering the acetonitrile and hydrogen cyanide from the quench column.
- reaction zone e.g. fluid bed reactor
- a catalyst e.g. fluid bed catalyst
- the ammoxidation conditions used in the manufacture of acrylonitrile as disclosed in U.S. Pat. No. 3,911,089 herein incorporated by reference may be utilized.
- the mixture of ketones is intended to include mixtures of commercially available ketones such as acetone, MIBK, methyl ethyl ketone etc. in either their purified, substantially purified, or crude form.
- commercially available crude ketones may be used by itself in the practice of the present invention.
- the term “crude ketone” shall mean a mixture of at least two ketones and a diluent (e.g. crude acetone shall comprises primarily acetone containing other ketones as impurities and water as a diluent).
- ammoxidation catalyst can be utilized to achieve the desired results.
- Typical ammoxidation catalysts can be generalized by the following two formulae:
- A Li, Na, K, Cs, Tl and combinations thereof, preferably Cs and K
- B Ni, Co, Mn, Mg, Ca and combinations thereof, preferably Ni, Co and Mg
- C Fe, Cr, Ce, Cu, V, Sb, W, Sn, Ga, Ge, In, P and combinations thereof, preferably Fe, Cr and Ce
- D Bi and/or Te, preferably Bi
- a 0.1-4.0, preferably 0.1 to 0.5, especially preferred being 0.1 to 0.2
- b 0.1-10.0, preferably 5 to 9, especially preferred being 6 to 8, and
- c,d 0.1-10.0, preferably 0.5 to 4, especially preferred being 0.5 to 3;
- A Fe, Cr, Ce, V, U, Sn, Ti, Nb and combinations thereof, preferably Fe, V, Sn and Ti
- B Mo, W, Co, Cu, Te, Bi, Zn, B, Ni, Ca, Ta and combinations thereof, preferably Mo and Cu
- a 0.1-16, preferably 2 to 12, especially preferred being 4 to 10
- b 0.0-12, preferably 1 to 10, especially preferred being 2 to 6, and
- the value of x depends on the oxidation state of the elements used.
- the catalyst can be used either unsupported, or be supported with silica, alumina, titania, zirconia and the like; however, silica is the preferred support.
- silica is the preferred support.
- catalysts envisioned as suitable in the practice of the present invention are disclosed in U.S. Pat. Nos. 3,642,930; 4,485,079; 3,911,089, 4,873,215; 5,134,105 and 5,093,299, herein incorporated by reference.
- the present invention is primarily directed to the utilization of a mixture of at least two ketones such as acetone and methyl isobutyl ketone as a source for the production of useful nitrile co-products (hydrogen cyanide and acetonitrile) produced during the manufacture of acrylonitrile.
- the process of the present invention is also applicable to the manufacture of on purpose acetonitrile and hydrogen cyanide by the direct ammoxidation of a mixture of C 1 to C 4 ketone and/or a crude ketone, ammonia and oxygen in a reaction zone in the presence of an ammoxidation catalyst.
- crude ketone as defined above, by itself, may be utilized in the practice of the present invention thereby further reducing the cost of the raw materials suitable for the production of viable co-products.
- the practice of the process of the present invention during the manufacture of acrylonitrile increases the yield of both HCN and acetonitrile during the manufacture of acrylonitrile.
- the practice of this aspect of the present invention comprises introducing a hydrocarbon selected from the group consisting of propylene and propane, a crude ketone, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the hydrocarbon, ketone, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
- a hydrocarbon selected from the group consisting of propylene and propane, a crude ketone, ammonia and air
- the process comprises introducing a hydrocarbon selected from the group consisting of propylene and propane, a mixture of at least two C 1 to C 4 ketones, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the hydrocarbon, ketones, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
- a hydrocarbon selected from the group consisting of propylene and propane, a mixture of at least two C 1 to C 4 ketones, ammonia and air
- the reactor conditions be adjusted to obtain the increased yield in acetonitrile and hydrogen cyanide obtained by utilizing the mixture of ketones and/or crude ketone.
- the ammoxidation reaction conditions should be within the following parameters: Crude ketone is between 1 and 50% of propylene or propane rate on a total carbon basis.
- the temperature of the reaction is between 410° to 460° C., preferably 405° to 440° C.
- the pressure is maintained at between 1 to 5 atmospheres with 1 to 3 atmospheres being preferred.
- the crude ketone mixture comprises a mixture containing acetone, MIBK and water.
- the process is performed in a fluid bed reactor.
- the mixture of ketones comprises crude ketone in combination with at least one substantially pure C 1 to C 4 ketone.
- the ketone is separately introduced into the reactor zone.
- the mixture of ketones and/or crude ketone is separately introduced into the fluid bed reactor, preferably at a location above the point where the hydrocarbon is fed into the reactor, especially preferred being a location in the upper portion of the reactor.
- ketones can be ammoxidized to a mixture of nitrites.
- the preferred ketones include C 1 to C 4 ketones.
- the following example illustrates the use of a C4 ketone in the form of methyl ethyl ketone (MEK). TABLE III Example % MEK as % AN % Aceto % HCN No. C Fed Yield Yield Yield 9 (comp.) 0 79.2 2.1 6.9 10 2.5 77.6 3.2 7.0 11 5 75.5 4.2 7.4
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
- The present invention is directed to a novel process for the ammoxidation of a mixture of ketones to a mixture of nitriles. In particular, the present invention is directed to increasing the yield of co-product hydrogen cyanide and acetonitrile produced during the ammoxidation of propylene to acrylonitrile.
- There are patents which address the issue of the injection of acetone into a fluid bed reactor to produce acetonitrile. In addition, these references further disclose that the acetone may be introduced into a fluid bed reactor to increase the co-product acetonitrile while manufacturing acrylonitrile. In particular, Japanese Patent Application 2[1990]-38,333 is directed to improving acetonitrile yields by injecting acetone and/or ethyl alcohol into ammoxidation reactor containing ammoxidation catalyst. The process disclosed in the Japanese Patent Application includes simultaneously injecting the acetone and/or ethyl alcohol into the ammoxidation reactor while manufacturing acrylonitrile.
- The present invention is directed to a process which increases the yield of both main co-products (i.e. HCN and acetonitrile) during the manufacture of acrylonitrile while (1) saving on the raw material costs associated with the increase in co-product yields and (2) achieving the same or better conversion and selectivity to the desired co-products.
- It is an object of the present invention to provide a process for the ammoxidation of a mixture of ketones and/or a crude ketone to hydrogen cyanide and acetonitrile.
- It is another object of the present invention to provide a process for substantially increasing the yields of co-product hydrogen cyanide and acetonitrile produced during the manufacture of acrylonitrile from propylene.
- It is a further object of the present invention to provide a process for the conversion of a mixture of ketones (e.g. acetone and methyl isobutyl ketone (MIBK)) into hydrogen cyanide and acetonitrile during the manufacture of acrylonitrile without substantially affecting the yield of the acrylonitrile.
- Additional objects and advantages and novel features of the invention will be set forth in part in the description which follows, and in part will become apparent to those skilled in the art upon examination of the following, or may be learned by the practice of the invention. The objects and advantages of the invention may be realized and attained by means of the instrumentalities and combinations particularly pointed out in the appended claims.
- To achieve the foregoing objects in accordance with the purpose of the present invention as broadly described herein, the method of the present invention comprises introducing a hydrocarbon selected from the group consisting of propylene and propane, a mixture of ketones (e.g. acetone and MIBK), ammonia and oxygen-containing gas into reaction zone (e.g fluid bed reactor)to react in the presence of a catalyst (e.g. fluid bed catalyst) to produce a reactor effluent comprising acrylonitrile, hydrogen cyanide and acetonitrile, passing the reactor effluent containing acrylonitrile, hydrogen cyanide and acetonitrile into a quench column to cool the reactor effluent, and recovering the acrylonitrile, acetonitrile and hydrogen cyanide from the quench column.
- In another aspect of the present invention, the process comprises introducing a mixture of ketones (e.g. acetone and MIBK) and/or a crude ketone, ammonia and oxygen-containing gas into reaction zone (e.g. fluid bed reactor) to react in the presence of a catalyst (e.g. fluid bed catalyst) to produce a reactor effluent comprising hydrogen cyanide and acetonitrile, passing the reactor effluent containing the hydrogen cyanide and acetonitrile into a quench column to cool the reactor effluent, and recovering the acetonitrile and hydrogen cyanide from the quench column. In the practice of this aspect of the present invention the ammoxidation conditions used in the manufacture of acrylonitrile as disclosed in U.S. Pat. No. 3,911,089 herein incorporated by reference may be utilized.
- For purposes of the present invention, the mixture of ketones is intended to include mixtures of commercially available ketones such as acetone, MIBK, methyl ethyl ketone etc. in either their purified, substantially purified, or crude form. In addition, commercially available crude ketones may be used by itself in the practice of the present invention. For purposes of this application the term “crude ketone” shall mean a mixture of at least two ketones and a diluent (e.g. crude acetone shall comprises primarily acetone containing other ketones as impurities and water as a diluent).
- In the practice of the present invention, it is envisioned that any ammoxidation catalyst can be utilized to achieve the desired results. Typical ammoxidation catalysts can be generalized by the following two formulae:
- AaBbCcDdMo12Ox where
- A=Li, Na, K, Cs, Tl and combinations thereof, preferably Cs and K
- B=Ni, Co, Mn, Mg, Ca and combinations thereof, preferably Ni, Co and Mg
- C=Fe, Cr, Ce, Cu, V, Sb, W, Sn, Ga, Ge, In, P and combinations thereof, preferably Fe, Cr and Ce
- D=Bi and/or Te, preferably Bi
- a=0.1-4.0, preferably 0.1 to 0.5, especially preferred being 0.1 to 0.2
- b=0.1-10.0, preferably 5 to 9, especially preferred being 6 to 8, and
- c,d=0.1-10.0, preferably 0.5 to 4, especially preferred being 0.5 to 3;
- and AaBbSb12Ox where
- A=Fe, Cr, Ce, V, U, Sn, Ti, Nb and combinations thereof, preferably Fe, V, Sn and Ti
- B=Mo, W, Co, Cu, Te, Bi, Zn, B, Ni, Ca, Ta and combinations thereof, preferably Mo and Cu
- a=0.1-16, preferably 2 to 12, especially preferred being 4 to 10
- b=0.0-12, preferably 1 to 10, especially preferred being 2 to 6, and
- the value of x depends on the oxidation state of the elements used.
- The catalyst can be used either unsupported, or be supported with silica, alumina, titania, zirconia and the like; however, silica is the preferred support. Typically, catalysts envisioned as suitable in the practice of the present invention are disclosed in U.S. Pat. Nos. 3,642,930; 4,485,079; 3,911,089, 4,873,215; 5,134,105 and 5,093,299, herein incorporated by reference.
- Reference will now be made in detail to the present preferred embodiments of the invention.
- The present invention is primarily directed to the utilization of a mixture of at least two ketones such as acetone and methyl isobutyl ketone as a source for the production of useful nitrile co-products (hydrogen cyanide and acetonitrile) produced during the manufacture of acrylonitrile. However, the process of the present invention is also applicable to the manufacture of on purpose acetonitrile and hydrogen cyanide by the direct ammoxidation of a mixture of C1 to C4 ketone and/or a crude ketone, ammonia and oxygen in a reaction zone in the presence of an ammoxidation catalyst. In addition, crude ketone (as defined above), by itself, may be utilized in the practice of the present invention thereby further reducing the cost of the raw materials suitable for the production of viable co-products.
- The practice of the process of the present invention during the manufacture of acrylonitrile increases the yield of both HCN and acetonitrile during the manufacture of acrylonitrile. The practice of this aspect of the present invention comprises introducing a hydrocarbon selected from the group consisting of propylene and propane, a crude ketone, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the hydrocarbon, ketone, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
- In another embodiment of this aspect of the present invention, the process comprises introducing a hydrocarbon selected from the group consisting of propylene and propane, a mixture of at least two C1 to C4 ketones, ammonia and air, into a reaction zone containing an ammoxidation catalyst, reacting the hydrocarbon, ketones, ammonia and oxygen over said catalyst at an elevated temperature to produce acrylonitrile, hydrogen cyanide and acetonitrile, and recovering the acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.
- In the preferred embodiment of this aspect of the present invention, it is necessary that the reactor conditions be adjusted to obtain the increased yield in acetonitrile and hydrogen cyanide obtained by utilizing the mixture of ketones and/or crude ketone. In the practice of the present invention, the ammoxidation reaction conditions should be within the following parameters: Crude ketone is between 1 and 50% of propylene or propane rate on a total carbon basis. The temperature of the reaction is between 410° to 460° C., preferably 405° to 440° C. Typically, the pressure is maintained at between 1 to 5 atmospheres with 1 to 3 atmospheres being preferred.
- In a further preferred embodiment of this aspect of the present invention the crude ketone mixture comprises a mixture containing acetone, MIBK and water.
- In a still further preferred embodiment of this aspect of the present invention the process is performed in a fluid bed reactor.
- In another preferred embodiment of this aspect of the present invention the mixture of ketones comprises crude ketone in combination with at least one substantially pure C1 to C4 ketone.
- In still another preferred embodiment of this aspect of the present invention, the ketone is separately introduced into the reactor zone.
- In a still further preferred embodiment of this aspect of the present invention, the mixture of ketones and/or crude ketone is separately introduced into the fluid bed reactor, preferably at a location above the point where the hydrocarbon is fed into the reactor, especially preferred being a location in the upper portion of the reactor.
- The following examples are set forth below for illustrative purposes and are not considered as limiting to the practice of the present invention. The catalyst utilized in all of the examples was a promoted BiFeMoOx known for its suitability in the ammoxidation of propylene to acrylonitrile. Five, 10 and 15% of the propylene feed (in terms of total carbon) was replaced with a ketone to give the results set forth below in Table I. In each of the following examples the reactor temperature was 430° C., the pressure was 9.5 psig and the feed ratio of propylene +alcohol/ammonia/air was 1/1.2/9.3. The wwh was 0.06 (grams of hydrocarbon/grams of catalyst-hour)
TABLE I Example % Acetone as % AN % Aceto % HCN No. C Fed Yield Yield Yield 1 (comp.) 0 78.6 2.0 6.7 2 5 75.5 3.1 7.5 3 10 72.3 4.1 8.4 4 15 68.3 5.2 9.6 - As a further example of the value of using crude ketones, 10% by weight water was blended with the acetone above and this was co-fed to the same propylene ammoxidation reactor. The results are shown below in Table II and indicate that water dilution has no deleterious effect on performance.
TABLE II Example % Blend as % AN % Aceto % HCN No. C Fed Yield Yield Yield 5 (comp.) 0 78.9 2.0 6.6 6 5 75.3 3.2 7.8 7 10 71.7 4.2 8.7 8 15 67.5 5.3 9.6 - In general, all ketones can be ammoxidized to a mixture of nitrites. The preferred ketones include C1 to C4 ketones. The following example illustrates the use of a C4 ketone in the form of methyl ethyl ketone (MEK).
TABLE III Example % MEK as % AN % Aceto % HCN No. C Fed Yield Yield Yield 9 (comp.) 0 79.2 2.1 6.9 10 2.5 77.6 3.2 7.0 11 5 75.5 4.2 7.4 - The following examples are illustrative of the practice of the present invention for direct ammoxidation of ketones to acetonitrile and HCN. The feed ratio for the ketone/ammonia/air used in Example 12 and 13 were 1/1.7/13.1 and 1/2/15.1 respectively. The temperature of the reaction was 413° C. for Example 12 and 41 1° C. for Example 13. The reactor pressure was 10 psig for both examples and the wwh was 0.133 and 0.149 for Examples 12 and 13, respectively. Table IV below sets forth the results for Examples 12 and 13.
TABLE IV Example % Aceto % HCN No. ketone % Conversion Yield Yield 12 acetone 98.9 28.0 27.8 13 methyl ethyl 99.9 46.0 16.5 ketone - While the examples are illustrative of the practice of the present invention, they are not intended to limit applicants' invention to that illustrated and obviously many modifications and variations may be utilized in light of the above teaching. It is intended that the scope of applicants' invention be defined by the claims appended hereto.
Claims (22)
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/320,937 US6413485B2 (en) | 1999-05-27 | 1999-05-27 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
BR0010997-5A BR0010997A (en) | 1999-05-27 | 2000-05-16 | Processes to increase the production of hcn and acetonitrile by-products produced during the manufacture of acrylonitrile, and for the amoxidation of a mixture of c1 to c4 ketones and a crude ketone to produce hcn and acetonitrile |
CNB008079978A CN1243726C (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
AU51359/00A AU5135900A (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
EP00935980A EP1181268B8 (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
AT00935980T ATE306468T1 (en) | 1999-05-27 | 2000-05-16 | AMMONOXIDATION OF A MIXTURE OF KETONES TO PRODUCE ACETONITRILE AND HYDROGEN Cyanide |
TR2001/03384T TR200103384T2 (en) | 1999-05-27 | 2000-05-16 | Conversion of a mixture of ketones to acetonitrile and hydrogen cyanide by amoxidation. |
PCT/US2000/013374 WO2000073261A1 (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
EP04078068A EP1520852A3 (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
DE60023134T DE60023134T2 (en) | 1999-05-27 | 2000-05-16 | AMMONOXIDATION OF A MIXTURE OF KETONES FOR THE MANUFACTURE OF ACETONITRILE AND HYDROGEN CYANO |
CNB2004100957067A CN1267347C (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones for generating acetonitrile and HCn |
ROA200101268A RO120909B1 (en) | 1999-05-27 | 2000-05-16 | Ammooxidation of a hydrocarbon and ketone mixture |
ES00935980T ES2249271T3 (en) | 1999-05-27 | 2000-05-16 | AMOXIDATION OF A KETONE MIXTURE IN ACETONITRILE AND HYDROGEN CYANIDE. |
KR1020017015230A KR100717551B1 (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
EA200101163A EA004864B1 (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyonide |
JP2000621328A JP2003500468A (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide. |
ZA200109165A ZA200109165B (en) | 1999-05-27 | 2001-11-06 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide. |
BG106099A BG65744B1 (en) | 1999-05-27 | 2001-11-09 | Ammonium oxidation of a ketones mixture to acetonitrile and hydrocyanogen |
US10/016,703 US6667020B2 (en) | 1999-05-27 | 2001-12-10 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US09/320,937 US6413485B2 (en) | 1999-05-27 | 1999-05-27 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
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US10/016,703 Continuation US6667020B2 (en) | 1999-05-27 | 2001-12-10 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
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US20020004027A1 true US20020004027A1 (en) | 2002-01-10 |
US6413485B2 US6413485B2 (en) | 2002-07-02 |
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US09/320,937 Expired - Fee Related US6413485B2 (en) | 1999-05-27 | 1999-05-27 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
US10/016,703 Expired - Fee Related US6667020B2 (en) | 1999-05-27 | 2001-12-10 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
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US10/016,703 Expired - Fee Related US6667020B2 (en) | 1999-05-27 | 2001-12-10 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
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US (2) | US6413485B2 (en) |
EP (2) | EP1520852A3 (en) |
JP (1) | JP2003500468A (en) |
KR (1) | KR100717551B1 (en) |
CN (2) | CN1243726C (en) |
AT (1) | ATE306468T1 (en) |
AU (1) | AU5135900A (en) |
BG (1) | BG65744B1 (en) |
BR (1) | BR0010997A (en) |
DE (1) | DE60023134T2 (en) |
EA (1) | EA004864B1 (en) |
ES (1) | ES2249271T3 (en) |
RO (1) | RO120909B1 (en) |
TR (1) | TR200103384T2 (en) |
WO (1) | WO2000073261A1 (en) |
ZA (1) | ZA200109165B (en) |
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JP4854151B2 (en) * | 2001-08-29 | 2012-01-18 | 旭化成ケミカルズ株式会社 | Method to stably increase production of acetonitrile and hydrocyanic acid |
US6982342B2 (en) * | 2002-05-16 | 2006-01-03 | Standard Oil Company | Ammoxidation of carboxylic acids to a mixture of nitriles |
RU2451548C2 (en) * | 2007-02-16 | 2012-05-27 | ИНЕОС ЮЭсЭй ЭлЭлСи | Method for oxidative ammonolysis of propane and isobutane in presence of mixed metal oxide catalysts |
US8585870B2 (en) * | 2008-03-05 | 2013-11-19 | E I Du Pont De Nemours And Company | Process to C-manufacture acrylonitrile and hydrogen cyanide |
CN104724725B (en) * | 2014-11-21 | 2017-05-24 | 重庆紫光化工股份有限公司 | hydrocyanic acid gas separation and purification system and method |
US10647663B2 (en) * | 2015-07-22 | 2020-05-12 | Invista North America S.A.R.L. | High purity HCN from acrylonitrile co-production |
KR20180100178A (en) | 2016-01-09 | 2018-09-07 | 어센드 퍼포먼스 머티리얼즈 오퍼레이션즈 엘엘씨 | Catalyst Compositions and Process for Direct Production of Hydrogen Cyanide in an Acrylonitrile Reactor Feed Stream |
Family Cites Families (11)
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US2006981A (en) * | 1931-12-14 | 1935-07-02 | Ig Farbenindustrie Ag | Production of hydrocyanic acid |
US3106574A (en) * | 1960-12-19 | 1963-10-08 | Standard Oil Co | Method for the manufacture of acetonitrile |
DE1247277B (en) | 1963-09-19 | 1967-08-17 | Knapsack Ag | Process for the preparation of a catalyst containing oxide of vanadium and tin |
GB1114898A (en) | 1964-08-17 | 1968-05-22 | Halcon International Inc | Production of aromatic nitriles and catalysts for use therefor |
US4272451A (en) | 1979-12-26 | 1981-06-09 | Monsanto Company | Acetonitrile process with improved catalysts |
CH642942A5 (en) | 1980-04-16 | 1984-05-15 | Lonza Ag | Process for the preparation of acetonitrile |
CA1320735C (en) * | 1987-11-24 | 1993-07-27 | Ramakrishnan Ramachandran | Process for the production of nitriles and anhydrides |
JPH03246269A (en) * | 1990-02-21 | 1991-11-01 | Asahi Chem Ind Co Ltd | Method for increasing yield of acetonitrile |
US5204079A (en) * | 1991-02-15 | 1993-04-20 | Standard Oil Company | HCN by catalytic ammoxidation of crude acetonitrile |
US5466857A (en) * | 1994-08-10 | 1995-11-14 | The Standard Oil Company | Process for reduction of waste material during manufacture of acrylonitrile |
UA54409C2 (en) * | 1997-07-16 | 2003-03-17 | Асахі Касеі Кабусікі Кайся | A Process for producing acrylonitrile or methacrylonitrile from propane оr isobutane by ammoxidation |
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1999
- 1999-05-27 US US09/320,937 patent/US6413485B2/en not_active Expired - Fee Related
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2000
- 2000-05-16 DE DE60023134T patent/DE60023134T2/en not_active Expired - Lifetime
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- 2000-05-16 KR KR1020017015230A patent/KR100717551B1/en not_active IP Right Cessation
- 2000-05-16 EA EA200101163A patent/EA004864B1/en not_active IP Right Cessation
- 2000-05-16 EP EP04078068A patent/EP1520852A3/en not_active Withdrawn
- 2000-05-16 EP EP00935980A patent/EP1181268B8/en not_active Expired - Lifetime
- 2000-05-16 ES ES00935980T patent/ES2249271T3/en not_active Expired - Lifetime
- 2000-05-16 RO ROA200101268A patent/RO120909B1/en unknown
- 2000-05-16 CN CNB2004100957067A patent/CN1267347C/en not_active Expired - Fee Related
- 2000-05-16 AT AT00935980T patent/ATE306468T1/en not_active IP Right Cessation
- 2000-05-16 TR TR2001/03384T patent/TR200103384T2/en unknown
- 2000-05-16 BR BR0010997-5A patent/BR0010997A/en not_active Application Discontinuation
- 2000-05-16 WO PCT/US2000/013374 patent/WO2000073261A1/en active IP Right Grant
- 2000-05-16 AU AU51359/00A patent/AU5135900A/en not_active Abandoned
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2001
- 2001-11-06 ZA ZA200109165A patent/ZA200109165B/en unknown
- 2001-11-09 BG BG106099A patent/BG65744B1/en unknown
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Also Published As
Publication number | Publication date |
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WO2000073261A1 (en) | 2000-12-07 |
US6413485B2 (en) | 2002-07-02 |
TR200103384T2 (en) | 2002-04-22 |
CN1351586A (en) | 2002-05-29 |
US20030198586A1 (en) | 2003-10-23 |
EP1181268B8 (en) | 2005-12-14 |
BG106099A (en) | 2002-06-28 |
EP1520852A2 (en) | 2005-04-06 |
DE60023134D1 (en) | 2006-02-23 |
DE60023134T2 (en) | 2006-04-13 |
EP1181268A1 (en) | 2002-02-27 |
ES2249271T3 (en) | 2006-04-01 |
CN1243726C (en) | 2006-03-01 |
EA004864B1 (en) | 2004-08-26 |
EP1181268B1 (en) | 2005-10-12 |
CN1629072A (en) | 2005-06-22 |
ZA200109165B (en) | 2003-02-06 |
RO120909B1 (en) | 2006-09-29 |
CN1267347C (en) | 2006-08-02 |
ATE306468T1 (en) | 2005-10-15 |
JP2003500468A (en) | 2003-01-07 |
EA200101163A1 (en) | 2002-12-26 |
KR100717551B1 (en) | 2007-05-15 |
BG65744B1 (en) | 2009-09-30 |
BR0010997A (en) | 2002-02-19 |
WO2000073261A9 (en) | 2002-06-27 |
EP1520852A3 (en) | 2005-09-21 |
KR20020003572A (en) | 2002-01-12 |
AU5135900A (en) | 2000-12-18 |
US6667020B2 (en) | 2003-12-23 |
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