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(12) United States Patent (10) Patent No.: US 6,649,757 B2 Kuroda Et Al

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(12) United States Patent (10) Patent No.: US 6,649,757 B2 Kuroda Et Al USOO6649757B2 (12) United States Patent (10) Patent No.: US 6,649,757 B2 Kuroda et al. (45) Date of Patent: Nov. 18, 2003 (54) PROCESS FOR PRODUCING FOREIGN PATENT DOCUMENTS LAUROLACTAM FROM CYCLODODECANONE CH 532 OS3 A 12/1972 EP O 487 090 A 5/1992 (75) Inventors: Nobuyuki Kuroda, Ube (JP); Joji EP O 785 188 A 7/1997 Kawai, Ube (JP); Hideo Shimomura, JP B43 12153 5/1968 Ube (JP) JP B48 10475 4/1973 (73) Assignee: Ube Industries, Ltd., Ube (JP) OTHER PUBLICATIONS * ) Notice: Subject to anyy disclaimer, the term of this patent is extended or adjusted under 35 Ritz, J. et al., “Caprolactam” Ullmann's Encyclopedia of U.S.C. 154(b) by 0 days. Industrial Chemistry. Cancer Chemotherapy to Ceramic Colorants, Weinheim, VCH Verlag, DE, vol. 15, 1986, pp. (21) Appl. No.: 10/345,548 31-50, XP002909167. (22) Filed: Jan. 16, 2003 (65) Prior Publication Data Primary Examiner Bruck Kifle US 2003/0139596 A1 Jul. 24, 2003 (74) Attorney, Agent, or Firm- Piper Rudnick LLP (30) Foreign Application Priority Data (57) ABSTRACT Jan. 16, 2002 (JP) ....................................... 2002-007549 Laurolactam having high quality is produced by reacting Feb. 28, 2002 (JP) ...... ... 2002-053903 cyclododecanone with a hydroxylamine Salt of a mineral Feb. 28, 2002 (JP) ...... ... 2002-053931 Mar. 29, 2002 (JP) ...... 2002-095O24 acid, and converting the resultant cyclododecanoneoxime to Jul. 18, 2002 (JP) r 2002-209935 laurolactam through the Beckmann rearrangement reaction, wherein a content of each of oxygen atom-containing C2 (51) Int. Cl. .............................................. C07D 225/02 organic compounds, for example, cyclododecenone or (52) U.S. Cl. ....................................................... 540/464 epoxycyclododecane, and cycloaliphatic unsaturated C. (58) Field of Search .......................................... 540/464 hydrocarbon compounds, contained, as an impurity, in the (56) References Cited Staring cyclododecanone material, is controlled to 1,000 ppm or less. U.S. PATENT DOCUMENTS 5.245,029 A 9/1993 Inaba et al. ................. 540/540 9 Claims, No Drawings US 6,649,757 B2 1 2 PROCESS FOR PRODUCING Furthermore, it is known that in a method for preparing a LAUROLACTAM FROM mixture of cyclododecanol with cyclododecanone, by oxi CYCLODODECANONE dizing cyclododecane with a molecular oxygen-containing gas, epoxycyclododecane is produced as a by-product, and in the distillation refining procedure for isolating refined BACKGROUND OF THE INVENTION cyclododecanone from the mixture, the distilled cyclodode canone fraction contains the above-mentioned epoxycy (1) Field of the Invention clododecane as an impurity. The present invention relates to a process for producing Still further, it is known that in the case where epoxycy laurolactam from cyclododecanone. More particularly, the 1O clododecadiene is used as a starting material for the pro present invention relates to a process for producing lauro duction of cyclododecanone, and Subjected to an isomeriza lactam having a high degree of purity from cyclododecanone tion reaction the re of, a Small amount of used as a Starting material. cycloundecylcarboxyaldehyde is produced as a by-product. Laurolactam is useful as a material for producing Syn The cycloundecylcarboxyaldehyde is an impurity which is thetic resins Such as polyamide resins. 15 difficult to Separate from cyclododecanone by distillation. (2) Description of the Related Art Also, in the method of preparing a mixture of cyclodode AS a conventional method of producing laurolactam, a canol with cyclododecanone by oxidizing cyclododecane method in which cyclodododecanone, having been prepared with a molecular oxygen-containing gas, undecylaldehyde is by oxidizing cyclododecane with molecular oxygen produced as a by-product and is contained in refined containing gas and dehydrogenating the resultant cyclododecanone fraction obtained by distillation of the cyclydodecanol, is reacted, as a Starting material, with a mixture. hydroxylamine mineral acid Salt to prepare cyclodode When the aldehyde compound-containing cyclodode canoneoxime and the resultant cyclododecanoneoxime is canone is Subjected to the cyclododecanoneoXime-preparing Subjected to the Beckmann rearrangement reaction to pro procedure and then to the Beckmann rearrangement duce the target laurolactam, is known. AS another method of 25 reaction, the aldehyde compound is converted to a corre producing cyclododecanone, a method in which epoxycy sponding amide compound and the amide compound is kept clododecadiene is reduced with hydrogen and the resultant contained in the target laurolactam. The contained amide epoxycyclododecane is isomerized with an alkali metal Salt, compound causes the quality of the resultant laurolactam to etc., to prepare the target cyclododecanone, is known. be decreased. In the method of producing cyclododecanone using, as a Furthermore, it is known from the disclosure of Japanese Starting material, epoxycyclododecadiene, in the case where Examined Patent Publication No. 43-12153 and No. the reduction of epoxycyclododecadiene with hydrogen is 48-10475 that, in the production of laurolactam by convert incompletely carried out, the resultant epoxycyclododecane ing cyclododecanone to an OXime thereof and Subjecting the contains an impurity consisting of epoxycyclododecene and 35 resultant cyclododecanoneoxime to the Beckmann rear the epoxycyclododecene is converted to cyclododecenone rangement reaction, if the temperature of the Beckmann by the isomerization reaction. The cyclododecenone is an rearrangement reaction is too high, the cyclododecanone impurity which is difficult to remove, as an impurity, from Oxime is decomposed due to the poor thermal Stability the target cyclododecanone by distillation. Also, in the case thereof, and the resultant laurolactam is unsatisfactory due to where cyclododecanol is dehydrogenated, cyclododecenone the low quality thereof. However, the prior art does not teach may be produced as a by-product, when the reaction con 40 or Suggest any possible influence of oxygen atom-containing ditions are inappropriate. organic compounds having 12 carbon atoms and Further it is known that, in the reaction for isomerizing cycloaliphatic unsaturated hydrocarbon compounds having epoxycyclododecane in the presence of an alkali metal Salt, 12 carbon atoms, for example, carbonyl group-containing undesired compounds having one or more double bonds 45 C-noncyclo-aliphatic and cycloaliphatic hydrocarbon between carbon atoms, Such as cyclododecadiene, compounds, epoxy group-containing C-noncyclo cyclododecene and cyclododecenol are produced as aliphatic and cycloaliphatic hydrocarbon compounds, alde by-products. hyde group-containing C-noncyclo-aliphatic and Further, it is known that, in the method in which cycloaliphatic hydrocarbon compounds, hydroxyl group cyclododecanone, having been prepared by oxidizing 50 containing C-noncyclo-aliphatic and cycloaliphatic hydro cyclododecane with a molecular oxygen-containing gas and carbon compounds contained in the Starting cyclodode dehydrogenating the resultant cyclododecanol, is employed canone material, on the quality of the target laurolactam. as a starting material for the production of laurolactam, the cyclododecanone produced by the oxidation of cyclodode SUMMARY OF THE INVENTION cane is further oxidized to produce 1,2-diketone compound 55 An object of the present invention is to provide a process and O-hydroxyketone compound, and the C-hydroxyketone for producing laurolactam having high quality, from compound is further converted to 1,2-diketone compound cyclododecanone, with a high efficiency. (cyclododecane-1,2-dione) during the dehydrogenation The above-mentioned object can be attained by the pro reaction procedure for cyclododecanol. ceSS of the present invention for producing laurolactam from Where cyclododecanone is produced from a starting 60 cyclododecanone, which comprises reacting cyclodode material consisting of epoxycyclododecadiene, the 1,2- canone with a hydroxylamine Salt of a mineral acid to diketone compound is not directly produced. However, prepare cyclododecanoneoxime, and converting the result when cyclododecanone is handled at a temperature of 100 ant cyclododecanoneoxime to laurolactam through the C. or more in the presence of a molecular oxygen-containing Beckmann rearrangement reaction, wherein a content of gas, the 1,2-diketone compound is produced. In this case, the 65 each of oxygen atom-containing organic compounds having 1,2-diketone compound is an impurity which is difficult to 12 carbon atoms and cycloaliphatic unsaturated hydrocar Separate from cyclododecanone by distillation. bon compounds having 12 carbon atoms, each contained, as US 6,649,757 B2 3 4 an impurity, in cyclododecanone used as a Starting material, impurity, in an amount more than a limited amount, the is controlled to 1,000 ppm or less. resultant laurolactam could not exhibit, even after a distil In the process of the present invention for producing lation refining is applied thereto, Satisfactory quality, for laurolactam, the total content of the oxygen atom-containing example, a Satisfactory differential light transmittance organic compounds having 12 carbon atoms and the (which will be referred to as LT.diff, hereinafter) of 25% or cycloaliphatic unsaturated hydrocarbon compounds having less, preferably 15% or less. Also, the inventors of the 12 carbon atoms and respectively contained, as impurities, present invention further found that the target laurolactam in the
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