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WO 2U11/151526 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date Χ t it t t 8 December 2011 (08.12.2011) WO 2U11/151526 Al (51) International Patent Classification: FI-04230 Kerava (FI). KAILA, Reetta [FI/FI]; Uuraantie C07C 5/373 (2006.01) C07C 15/02 (2006.01) 4b, FI-02140 Espoo (FI). C01B 39/24 (2006.01) (74) Agent: BERGGREN OY AB; P.O. Box 16 (Antinkatu 3 (21) International Application Number: C), FI-00101 Helsinki (FI). PCT/FI201 1/0505 18 (81) Designated States (unless otherwise indicated, for every (22) International Filing Date: kind of national protection available): AE, AG, AL, AM, 3 June 201 1 (03.06.201 1) AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, English (25) Filing Language: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (26) Publication Language: English HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (30) Priority Data: ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, 20105630 3 June 2010 (03.06.2010) FI NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (71) Applicant (for all designated States except US): STORA SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, ENSO OYJ [FI/FI]; P.O. Box 309, FI-00101 Helsinki TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (FI). (84) Designated States (unless otherwise indicated, for every (72) Inventors; and kind of regional protection available): ARIPO (BW, GH, (75) Inventors/ Applicants (for US only): RASANEN, Jari GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, [FI/FI] ; Vastarakinkuja 15, FI-55420 Imatra (FI). PENT- ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TINEN, Tapani [FI/FI]; Lokorentie 3 1, FI-49210 Hu- TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, ΓΓ utjarvi (FI). HARLIN, Ali [FI/FI]; Talvikinkatu 6 D 13, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, , LT, LU, [Continued on next page] (54) Title: METHOD OF CONVERTING ALPHA-PINENE TO PARA-CYMENE BY USING A ZEOLITIC CATALYST (57) Abstract: Herein disclosed is biobased p-cymene, which can further be converted to terephtalate. Further, here is described a method for convert ing crude sulphate turpentine recovered Y(N2) from chemical wood pulping into p- cymene and eventually to terephtalic Y(02) acid of biological origin, and and prod Y{N2, CST) ucts thereof respectively. In said method, both conversion and desul- phurisation is realised in one reaction Mar step. Present disclosure is also related to Y use of zeolite catalysts in said method. Y{N2, CST) ivlor a-Y powder) 13X 13X Y p wd r) , cat. Fig. 5 w o 2011/151526 Ai III III II II III I I1 1 I ll ll II IIIII III II III LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, before the expiration of the time limit for amending the SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, claims and to be republished in the event of receipt of GW, ML, MR, NE, SN, TD, TG). amendments (Rule 48.2(h)) Published: Method of converting alpha-pinene to para-cymene by using a zeolitic catalyst Field of the invention The present invention is related to biobased p-cymene, which can further be con- verted to terephtalate. More specifically, it discloses a method for converting sul phate turpentine present in chemical wood pulping into p-cymene and eventually to terephtalic acid of biological origin. It is also related to use of zeolite catalysts in said method. Background of the invention The need for biobased reagents, chemicals and products replacing oil-based, tra ditional raw materials is constantly growing. Applications for this bioreplacement are entering new fields. Terephtalic acid is the main monomer of the dominant polyester polymers, finding wide use in textiles, technical applications, packaging especially bottles and films. One of these polymers, polyethylene terephtalate (PET) is a thermoplastic polymer resin of the polyester family and is used in synthetic fibres. It has several benefits like high transparency, low weight, very good mechanical characteristics, good barrier properties, good form stability, high recyclability, health authorities' a p proval (FDA, EU) and economic production. For bioreplacement in polyethylene terephtalate PET and polybutylene terephta late PBT it is essential to find efficient production routes for the terephtalic acid. Para-cymene (p-cymene) is a common precursor for oxidative production of terephtalic acid of plant-based limonene, terpinenes, and pinenes, which are re coverable in citrus fruit peals, tee three oil, turpentine respectively, and through isoprenoid pathway of carbohydrates. When applying commercial oxidation proc ess for the cymene, yield of 90% of terephtalic acid is achieved. It is desirable to increase the value of crude sulphur turpentine (CST) by convert ing it to a more valuable chemical, such as p-cymene. p-Cymene is an aromatic hydrocarbon that can be utilized as raw material in the synthesis of polymers, but there are also many other applications for p-cymene e.g. in the production of fine chemicals (Monteiro, J. L . F., Veloso, C. O., Catalytic conversion of terpenes into fine chemicals, Top. Catal. 27 1-4 (2004) 169-1 80). Industrially, p-cymene is pro duced by alkylation of toluene with propene. Worldwide production of pinenes was 0.33 Mton / year based on FAO statistics on 1995. Of this 70% was sulphate turpentine CST from wood in chemical pulping processes, consisting 90% alpha- and beta-pinenes. However, the pulping proc ess originated aromates contain sulphur, which causes problems in further refine ment of pinenes, especially poisoning the catalyst and leaving an unacceptable odour to PET eventually produced from terphtalate. Some processes for the conversion of pinenes into cymenes are known. Determi- nation of liquid phase reaction conditions and selection of catalyst for preparation of p-cymene from c -pinene has been reviewed by Wang (Huaxue Shijie (2001 ), 42(3), 13 1- 1 33 CODEN: HUAKAB; ISSN: 0367-6358). The preparation of p- cymene from cc-pinene was studied by ring-opening-isomerization and hydrogen transfer disproportionation with a catalyst like Raney nickel, copper formate, and p-toluenesulfonic acid. Pinenes can be dehydrogenated and aromatized in presence of Pd-catalyst close to atmospheric pressure and 200-400 °C temperature, based on Horderlich, A p plied Catalysis, A : General (2001 ) , 2 15(1-2),1 11- 124 CODEN: ACAGE4; ISSN: 0926-860X. The dehydrogenation of cc-pinene to p-cymene is conducted over car- riers impregnated with Pd. An optimal acid strength is required to cleave selec tively the C-C bond in the cyclobutane ring of cc-pinene. Too strong acid sites such as in zeolites favor side reactions like oligomerization and cracking. Too weak acid sites fail to cleave the aforementioned C-C bond and rapid hydrogenation of the cc- pinene is a consequence. Hydrogenolysis is also a major side reaction leading to tetramethylcyclohexanes. A reaction mechanism is proposed in which first isom- erization is involved followed by hydrogenation/dehydrogenation to stabilize the components. The catalyst has a dual-functionality with the acid sites in charge of isomerization and the metallic sites responsible of hydrogenation/dehydrogen ation. The use of crude sulphate turpentine (CST) as raw material shows that β- pinene has a similar reactivity as cc-pinene and high yields of p-cymene can be obtained from this cheap starting material. The sulphur remains however a major drawback. The process yields 65% from pinenes and 59% of the turpentines. However, when applying CST, sulphur must be removed, because it poisons the catalyst rapidly. Bazhenov et.al. in Russian Journal of Applied Chemistry (Translation of Zhurnal Prikladnoi Khimii) (2003), 76(2), 234-237 CODEN: RJACEO; ISSN: 1070-4272, reported hydrogenation and isomerization of a-pinene on zeolite Y and heteroge neous nickel catalysts. Nickel catalyst supported on alumina reached 80% conver- sion in 2 hours at 400-450 °C and 0.5 MPa hydrogen pressure. However, nickel is especially sensitive for sulphur. Kutuzov et.al. disclose in RU 22001 44, a process for skeletal isomerization and dehydrogenation of α-pinene in presence of zeolite-containing cracking catalyst (Z-1 0) preliminarily activated for 1-2 h at 300-550 °C in nitrogen flow. Process is carried out for 2-8 h at 150-1 70 °C and 5 atmospheric nitrogen pressure. The re action is typically robust for sulphur and yields 80% conversion to p-cymene. However, even when not harmful for the process, the remaining sulphur may be undesirable in the end products, i.e. in plastics intended for food packages. As such, it requires separate processes for sulphur removal. Removal of sulphur- containing compounds from sulphate wood turpentine has been studied widely. Chudinov et.al. disclose in SU 3321 15 removal of sulphur impurities from turpen tine oil by treatment with sodium hypochlorite solution in the presence of a mineral acid. Another document, US 3778485 disclose purification of crude sulphate turpentine by agitating with sodium hypochlorite solution containing 90 g/l available C I fo l lowed by washing. The composition of the bleached turpentine was a-pinene 76.4, camphene 1.3, β-pinene 13.8, myrcene 2.2, dipentene 3.6, pine oil 2 , heavies 0.6, S (weight/volume) 0.01 4 , and chloride (weight/volume) 0.092.
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