[특허]Preparation of acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene

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Preparation of acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene

특허상세정보
국가/구분	United States(US) Patent 등록
국제특허분류(IPC7판)	C07C-029/00 C07C-053/00 C07C-045/00
미국특허분류(USC)	562/546; 562/512.2; 568/479
출원번호	UP-0131261 (2005-05-18)
등록번호	US-7592483 (2009-10-20)
우선권정보	DE-10 2004 032 129(2004-07-01); DE-10 2005 009 885(2005-03-01); DE-10 2005 009 891(2005-03-01); DE-10 2005 010 111(2005-03-02); DE-10 2005 013 039(2005-03-18)
발명자 / 주소	Dieterle, Martin Diefenbacher, Armin Schindler, Goetz Peter Klanner, Catharina Mueller Engel, Klaus Joachim Adami, Christoph
출원인 / 주소	BASF Aktiengesellschaft
대리인 / 주소	Oblon, Spivak, McClelland, Maier & Neustadt, P.C.
인용정보	피인용 횟수 : 3 인용 특허 : 31

초록

A process for preparing acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas oxidation of propylene, in which the starting reaction gas mixture has the following contents: from 6 to 9% by volume of propylene, from 8 to 18% by volume of molecular oxygen, from 6 to 30% by volume of propane and from 32 to 72% by volume of molecular nitrogen.

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What is claimed is: 1. A process for preparing acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene, in which a starting reaction gas mixture 2 which comprises the propylene and molecular oxygen reactants and inert molecular nitrogen and propane diluent gases and is conducted at elevated temperature through a fixed catalyst bed whose active composition is at least one multimetal oxide comprising the elements Mo, Fe and Bi, wherein starting reaction gas mixture 2, based on its total volume, has the following contents: from 7 to 9% by volume of propylene, from 9.8 to 15.5% by volume of molecular oxygen, from 10.5 to 15.5% by volume of propane and from 40 to 60% by volume of molecular nitrogen, with the proviso that the molar ratio V1 of propane present in starting reaction gas mixture 2 to propylene present in starting reaction gas mixture 2 is from 1.5 to 2.2, the molar ratio V2 of molecular nitrogen present in starting reaction gas mixture 2 to molecular oxygen present in starting reaction gas mixture 2 is from 3.5 to 4.5 and the molar ratio V3 of molecular oxygen present in starting reaction gas mixture 2 to propylene present in starting reaction gas mixture 2 is from 1.5 to 2.14. 2. The process according to claim 1, wherein V2 is from 3.5 to 4. 3. The process according to claim 1, wherein V3 is from 1.5 to 2.0. 4. The process as claimed in claim 1, wherein starting reaction gas mixture 2 has the following contents: from 7 to 8% by volume of propylene, from 11.9 to 15.5% by volume of molecular oxygen, from 11.9 to 15.5% by volume of propane and from 50 to 60% by volume of molecular nitrogen, with the proviso that V1=from 1.7 to 2.1 V2=from 3.5 to 4.5 and V3=from 1.7 to 2.1. 5. The process according to claim 4, wherein V2 is from 3.5 to 4. 6. The process according to claim 4, wherein V3 is from 1.8 to 2.0. 7. The process according to claim 1, wherein the total content in starting reaction gas mixture 2 of constituents other than propylene, molecular oxygen, propane and molecular nitrogen is ≦10% by volume. 8. The process according to claim 1, wherein starting reaction gas mixture 2 comprises from 0.5 to 8% by volume of at least one of the compounds methane and ethane. 9. The process according to claim 1, wherein starting reaction gas mixture 2 comprises from 0.5 to 5% by volume of at least one of the compounds methane and ethane. 10. The process according to claim 1, wherein starting reaction gas mixture 2 comprises from 0.5 to 3% by volume of at least one of the compounds methane and ethane. 11. The process according to claim 1, wherein starting reaction gas mixture 2 comprises ≦5% by volume of water and ≦5% by volume of carbon oxides. 12. The process according to claim 1, wherein starting reaction gas mixture 2 comprises ≦3% by volume of water and ≦3% by volume of carbon oxides. 13. The process according to claim 1, wherein starting reaction gas mixture 2 comprises ≦2% by volume of water and ≦2% by volume of carbon oxides. 14. The process according to claim 1, wherein starting reaction gas mixture 2 comprises ≧0.5% by volume of water. 15. The process according to claim 1, wherein the total content in starting reaction gas mixture 2 of constituents other than propylene, molecular oxygen, propane and molecular nitrogen is ≦5% by volume. 16. The process according to claim 1, wherein the total content in starting reaction gas mixture 2 of constituents other than propylene, molecular oxygen, propane and molecular nitrogen is ≦3% by volume. 17. The process according to claim 1, wherein the source used for the propylene present in starting reaction gas mixture 2 is propylene formed in processes for the continuous heterogeneously catalyzed partial dehydrogenation and/or oxydehydrogenation of propane in the gas phase, without propane unconverted in the heterogeneously catalyzed partial dehydrogenation and/or oxydehydrogenation being removed beforehand from this propylene. 18. The process according to claim 17, wherein the process of a heterogeneously catalyzed partial dehydrogenation of propane is an autothermal dehydrogenation. 19. The process according to claim 17, wherein the process for the heterogeneously catalyzed partial dehydrogenation of propane is one in which a starting reaction gas mixture 1 comprising the propane to be dehydrogenated is fed continuously to a dehydrogenation zone, in the dehydrogenation zone, starting reaction gas mixture 1 is conducted through at least one fixed catalyst bed over which molecular hydrogen and propylene are formed by catalytic dehydrogenation, at least one molecular oxygen-containing gas is added to starting reaction gas mixture 1 before and/or after entry into the dehydrogenation zone, the molecular oxygen is oxidized in the dehydrogenation zone partly to steam in the molecular hydrogen present in reaction gas mixture 1 and a product gas which comprises molecular hydrogen, steam, propylene and unconverted propane is withdrawn from the dehydrogenation zone, with the proviso that the product gas withdrawn from the dehydrogenation zone is divided into two portions of identical composition and one of the two portions is recycled into the dehydrogenation zone as dehydrogenation cycle gas. 20. The process according to claim 19, wherein the dehydrogenation cycle gas is recycled into starting reaction gas mixture 1. 21. The process according to claim 20, wherein starting reaction gas mixture 1 comprises: from 15 to 25% by volume of propane, from 2 to 6% by volume of propylene, from 5 to 20% by volume of steam, from 2 to 10% by volume of molecular hydrogen, from 40 to 75% by volume of molecular nitrogen and from >0 to 3% by volume of molecular oxygen. 22. The process according to claim 20, wherein the product gas comprises propane and propylene in a molecular propene to propylene ratio of from 0.3 to 0.66. 23. The process according to claim 1, wherein the source used for the propylene present in starting reaction gas mixture 2 is the product gas mixture of a partial propane dehydrogenation in which at least 50% by volume of the constituents other than propane and propylene present in the product gas of the propane dehydrogenation have been removed. 24. The process according to claim 1, wherein the hourly space velocity on the fixed catalyst bed of propylene is from ≧135 l (STP)/l·h to 300 l (STP)/l·h. 25. The process according to claim 1, wherein the propylene conversion in single pass is ≧90 mol % and the associated selectivity of acrolein formation and of acrylic acid by-product formation taken together is ≧90 mol % and a) the hourly space velocity on the fixed catalyst bed of propylene present in starting reaction gas mixture 2 is ≧160 l (STP) of propylene/l of fixed catalyst bed·h, b) the fixed catalyst bed consists of one fixed catalyst bed arranged in two spatially successive reaction zones A*, B*, the temperature of reaction zone A* being from 300 to 390° C. and a temperature of reaction zone B* being from 305 to 420° C. and at the same time at least 5° C. above the temperature of reaction zone A*, c) starting reaction gas mixture 2 flows through reaction zones A*, B* in the time sequence "first A*", "then B*" and d) reaction zone A* extends up to a conversion of propylene of from 40 to 80 mol %. 26. The process according to claim 1, which is followed by a process for the heterogeneously catalyzed partial gas phase oxidation of acrolein formed in the process according to claim 1 to acrylic acid, in which a starting reaction gas mixture 3 comprising acrolein is conducted through a fixed catalyst bed whose active composition is at least one multimetal oxide comprising the elements Mo and V. 27. The process according to claim 26, wherein starting reaction gas mixture 3 has the following contents: from 4.5 to 8% by volume of acrolein, from 2.25 to 9% by volume of molecular oxygen, from 6 to 30% by volume of propane, from 32 to 72% by volume of molecular nitrogen, from 5 to 15% by volume of steam. 28. The process according to claim 27, wherein starting reaction gas mixture 3 comprises from 4.5 to 9% by volume of molecular oxygen. 29. The process according to claim 26, wherein starting reaction gas mixture 3 has the following contents: from 5.5 to 8% by volume of acrolein, from 2.75 to 9% by volume of molecular oxygen, from 10 to 25% by volume of propane, from 40 to 70% by volume of molecular nitrogen, from 5 to 15% by volume of steam. 30. The process according to claim 29, wherein starting reaction gas mixture 3 comprises from 5.5 to 9% by volume of molecular oxygen. 31. The process according to claim 26, wherein starting reaction gas mixture 3 has the following contents: from 6 to 8% by volume of acrolein, from 3 to 9% by volume of molecular oxygen, from 10 to 20% by volume of propane, from 50 to 65% by volume of molecular nitrogen, from 7 to 13% by volume of steam. 32. The process according to claim 31, wherein starting reaction gas mixture 3 comprises from 6 to 9% by volume of molecular oxygen. 33. The process according to claim 31, wherein starting reaction gas mixture 3 comprises from 6 to 7% by volume of acrolein. 34. The process according to claim 31, wherein starting reaction gas mixture 3 comprises from 10 to 16% by volume of propane. 35. The process according to claim 27, wherein starting reaction gas mixture 3 comprises from 0.5 to 8% by volume of methane and/or ethane. 36. The process according to claim 26, wherein the acrolein hourly space velocity on the fixed catalyst bed is from ≧135 l (STP)/l·h to 290 l (STP)/l·h. 37. The process according to claim 26, wherein the acrolein conversion in single pass is ≧90 mol % and the associated selectivity of acrylic acid formation is ≧90 mol %, and a) the hourly space velocity on the fixed catalyst bed of acrolein present in starting reaction gas mixture 3 is ≧150 l(STP) of acrolein/l of fixed catalyst bed·h, b) the fixed catalyst bed consists of one fixed catalyst bed arranged in two spatially successive reaction zones C*, D*, the temperature of reaction zone C* being from 230 to 270° C. and a temperature of reaction zone D* being from 205 to 300° C. and at the same time at least 5° C. above the temperature of reaction zone C*, c) starting reaction gas mixture 3 flows through reaction zones C*, D* in the time sequence "first C*", "then D*"and d) reaction zone C* extends up to a conversion of acrolein of from 55 to 85 mol %. 38. The process according to claim 1, which is followed if appropriate by a process for the heterogeneously catalyzed partial gas phase oxidation of acrolein formed in the process according to claim 1, in which this acrolein is conducted as a constituent of a starting reaction gas mixture 3 through a fixed catalyst bed whose active composition is at least one multimetal oxide comprising the elements Mo and V, and, in a first stage preceding the process according to claim 1, propane is subjected, as a constituent of a starting reaction gas mixture 1, to a partial heterogeneously catalyzed dehydrogenation in the gas phase to form a product gas mixture 1 which comprises propylene and unconverted propane, a portion is removed if appropriate from the constituents other than propane and propylene present in the product gas mixture 1, comprising propylene and unconverted propane, of the preceding stage and it is then used as a constituent of starting reaction gas mixture 2, acrolein, acrylic acid or a mixture thereof is removed as the target product from the product gas mixture resulting from the partial gas phase oxidation and at least unconverted propane remaining in this removal is recycled into the preceding first stage and fresh propane is added to starting reaction gas mixture 2 and/or to starting reaction gas mixture 3. 39. The process according to claim 26, which is followed by a process in which the product gas mixture of the acrolein partial oxidation, after direct and/or indirect cooling if appropriate, is fractionally condensed ascending within a column comprising separating internals with side draw removal of crude acrylic acid and/or absorbed with water and/or aqueous solution. 40. The process according to claim 39, which is followed by a process in which the crude acrylic acid is subjected to a suspension crystallization to form acrylic acid suspension crystals and remaining mother liquor. 41. The process according to claim 40, which is followed by a process in which the acrylic acid suspension crystals are removed from remaining mother liquor by means of a wash column. 42. The process according to claim 41, wherein the wash column is one with forced transport of the crystal bed. 43. The process according to claim 41, wherein the wash column is a hydraulic wash column. 44. The process according to claim 41, wherein the wash liquid used is the melt of acrylic acid crystals which have been removed beforehand in the wash column. 45. The process according to claim 41, which is followed by a process in which the removed acrylic acid suspension crystals are melted and free-radically polymerized to polymers.

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Preparation of acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene

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Preparation of acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene

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