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(12) United States Patent (10) Patent No.: US 9,328,220 B2 Walker (45) Date of Patent: May 3, 2016

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(12) United States Patent (10) Patent No.: US 9,328,220 B2 Walker (45) Date of Patent: May 3, 2016 USOO9328220B2 (12) United States Patent (10) Patent No.: US 9,328,220 B2 Walker (45) Date of Patent: May 3, 2016 (54) LIQUIDS 5,371,166 A 12/1994 Farkas et al. 5,464,880 A 11/1995 Weber et al. 6,361,940 B1 3/2002 Van Ness et al. (71) Applicant: INNOVIA FILMS LIMITED, Cumbria 6,472,565 B1 10/2002 Bahrmann et al. (GB) 6,506,239 B1 1/2003 Osumi et al. 6,900,313 B2 5/2005 Wasserscheid et al. (72) Inventor: Adam John Walker, Lincolnshire (GB) 7,167,353 B2 1/2007 Yuyama et al. 7,754.462 B2 * 7/2010 Kragl ........................ C12P1/OO (73) Assignee: Innovia Films Limited, Cumbria (GB) 252,364 8,784.686 B2 * 7/2014 Walker ................... B01J 31,003 252,364 (*) Notice: Subject to any disclaimer, the term of this 8,992,798 B2* 3/2015 Walker ................... B01J 31,003 patent is extended or adjusted under 35 252,364 U.S.C. 154(b) by 151 days. 2003. O149264 A1 8, 2003 Wasserscheid et al. 2003/0232844 A1* 12/2003 Rogier, Jr. ............ CO7D 215.54 514,260.1 (21) Appl. No.: 14/191,750 2007/0185.330 A1 8, 2007 Walker 2008. O191170 A1* 8, 2008 Walker ................... B01J 31,003 (22) Filed: Feb. 27, 2014 252,364 2008, 0221361 A1* 9, 2008 Walker ................... B01J 31,003 (65) Prior Publication Data 564,508 2008/0258113 A1 10/2008 Clyburne et al. US 2014/O187684 A1 Jul. 3, 2014 2011/O257.433 A1 10/2011 Walker Related U.S. Application Data FOREIGN PATENT DOCUMENTS (63) Continuation of application No. 10/599,694, filed as DE 262 042 A1 11, 1988 application No. PCT/GB2005/001364 on Apr. 7, 2005, DE 103 06 617 A1 8, 2004 EP O 430 772 A2 6, 1991 now Pat. No. 8,784,.686. EP 1205 555 A1 5, 2002 EP 1380 569 A1 1, 2004 (30) Foreign Application Priority Data EP 1736,542 A1 12/2006 FR 2835 447 A1 8, 2003 Apr. 7, 2004 (GB) ................................... 04O7908.3 GB 8792.59 10, 1961 GB 1391922 4, 1975 GB 1509 230 5, 1978 (51) Int. Cl. WO 01f85129 A2 11/2001 BOIF I/O (2006.01) WO O3,060057 A2 T 2003 CSK 3/345 (2006.01) WO 03/074494 A1 9, 2003 BOI.3L/00 (2006.01) WO 2004/063383 A1 T 2004 BOI.3L/02 (2006.01) WO 2004/090066 A1 10, 2004 WO 2004/114445 A1 12/2004 C07C 215/08 (2006.01) WO 2005/097731 A2 10/2005 C07C 215/12 (2006.01) WO WO 2005097731 A2 * 10, 2005 ............. B01J 31,003 C07C 2.17/30 (2006.01) OTHER PUBLICATIONS CSK 3/19 (2006.01) Concise Science Dictionary, Oxford University Press, 1984, pp. 74, (52) U.S. Cl. 75,242, 243,568, and 569.* CPC ............. C08K 5/3415 (2013.01); B01.J31/003 Office Action from related U.S. Appl. No. 13/170,686, dated Sep. 24. 2014; 10 pgs. (2013.01); B01J 31/0278 (2013.01); C07C Notice of Allowance from related U.S. Appl. No. 13/170,686, dated 215/08 (2013.01); C07C 215/12 (2013.01); Dec. 10, 2014; 8 pgs. C07C2 1730 (2013.01); C08K5/19 (2013.01); International Search Report for PCT/GB2005/00 1364, dated Sep. 22, CION 2220/04 (2013.01); Y02P 20/542 2005, 4pgs. (2015.11) GB Patent Search for GB0506984.4, dated Jul. 27, 2005, 1 pg. Alekseeva et al., “On the Synthesis of Folic Acid Fragments”. Rus (58) Field of Classification Search sian Journal of General Chemistry, 1963, pp. 1649-1650, vol. 33, No. CPC ....... B01F 3/1214; B01F 1700; C07C 215/40: 5 B01J 31/04; B01J 31/02 Anderson et al., “Characterizing Ionic Liquids on the Basis of Mul USPC ................................ 252/364; 264/37.18, 349 tiple Solvation Interactions”, Journal of the American Chemical See application file for complete search history. Society, 2002, pp. 14247-14254, vol. 124, No. 47. Armstrong et al., “Ionic Liquids as Matrixes for Matrix-Assisted (56) References Cited Laser Desorptionlonization Mass Spectrometry”. Analytical Chem istry, 2001, pp. 3679-3686, vol. 73, No. 15. U.S. PATENT DOCUMENTS (Continued) 3,751,561 A * 8/1973 Wildi ..................... A61Q 11/00 424/48 Primary Examiner — Douglas McGinty 4,001,156 A * 1/1977 Bosso ................ CO8G 59,4078 (57) ABSTRACT 523,414 4,189,761 A 2f1980 Finkelstein et al. The present invention relates to an ionic liquid comprising an 4,191,674. A * 3/1980 Wismer ............... CO9D 5.4488 anion and a cation, wherein the cation is a primary, secondary 523,414 or tertiary ammonium ion containing a protonated nitrogen 4,219,624 A 8, 1980 Fuzesi. atOm. 4,377,654 A 3, 1983 Haas et al. 4,709,083. A 1 1/1987 Spielvogel 10 Claims, No Drawings US 9,328.220 B2 Page 2 (56) References Cited Williams et al., “Pressure Dependence of the Glass Transition Tem perature in Ionic Liquids and Solutions. Evidence Against Free Vol OTHER PUBLICATIONS ume Theories'. The Journal of Physical Chemistry, 1977, pp. 232 237, vol. 81, No. 3. Bicak, "A new ionic liquid: 2-hydroxy ethylammonium formate”. Non-Final Office Action from related U.S. Appl. No. 10/599,694, Journal of Molecular Liquids, 2005, pp. 15-18, vol. 116. dated Mar. 24, 2009, 8 pgs. CAS Registry No. 38739-74-1; Nov. 16, 1984. CAS Registry No. 2498-25-1; Nov. 16 1984. Final Office Action from related U.S. Appl. No. 10/599,694, dated CAS Registry No. 62640-03-3; Nov. 16, 1984. Feb. 17, 2011, 6 pgs. CAS Registry No. 138036-64-3; Dec. 21, 1991. Non-Final Office Action from related U.S. Appl. No. 10/599,694, CAS Registry No. 90001-96-0; Nov. 16, 1984. dated Jul. 20, 2011, 7 pgs. CAS Registry No. 58937-21-6; Nov. 16, 1984. Non-Final Office Action from related U.S. Appl. No. 10/599,694, CAS Registry No. 90434-46-1; Nov. 16, 1984. dated Mar. 1, 2012, 9 pgs. CAS Registry No. 137360-57-7; Nov. 15, 1991. Final Office Action from related U.S. Appl. No. 10/599,694, dated CAS Registry No. 59101-30-3; Nov. 16, 1984. Aug. 16, 2012, 8 pgs. Concise Science Dictionary, Oxford University Press, 1984, pp. 242 Non-Final Office Action from related U.S. Appl. No. 10/599,694, 243. dated Jan. 4, 2013, 7 pgs. Database Beilstein, Beilstein Institut Zur Forderung der Chemischen Final Office Action from related U.S. Appl. No. 10/599,694, dated Wissenschaft, Database accession No. 3613277 abstract & Russian Jul. 16, 2013, 9 pgs. Journal of General Chemistry, 1963, pp. 1649-1650, vol. 33, No. 5. Notice of Allowance from related U.S. Appl. No. 10/599,694, dated Database Beilstein, Beilstein Institut Zur Forderung der Chemischen Nov. 27, 2013, 10 pgs. Wissenschaft, Database accession No. 3694.926 abstract & Biochem. Notice of Allowance from related U.S. Appl. No. 10/599,694, dated Z., 1953, pp. 485, 490, vol. 324. Mar. 24, 2014, 8 pgs. Database Beilstein, Beilstein Institut Zur Forderung der Chemischen Non-Final Office Action from related U.S. Appl. No. 13/170,686, Wissenschaft, Database accession No. 5160694 abstract & Russian dated Apr. 13, 2012, 5 pgs. Journal of General Chemistry, 1985, pp. 379-386, vol. 21, No. 2. Non-Final Office Action from related U.S. Appl. No. 13/170,686, Poole et al., “Organic Salts, Liquid at Room Temperature, as Mobile dated Jul. 23, 2012, 6 pgs. Phases in Liquid Chromatography, Journal of Chromatography, Final Office Action from related U.S. Appl. No. 13/170,686, dated 1986, pp. 407-425, vol. 352. Jan. 30, 2013, 8 pgs. Seth et al., “Solvent and Rotational Relaxation of Coumarin 153 in a Non-Final Office Action from related U.S. Appl. No. 13/170,686, Protic Ionic Liquid Dimethylethanolammonium Formate”. The Jour dated Jun. 10, 2013, 7 pgs. nal of Physical Chemistry B, 2008, pp. 2629-2636, vol. 112, No. 9. Final Office Action from related U.S. Appl. No. 13/170,686, dated Walker et al., “Combined biological and chemical catalysis in the Jan. 30, 2014, 9 pgs. preparation of oxycodone”, Tetrahedron, 2004, pp. 561-568, Vol. 60, Non-Final Office Action from related U.S. Appl. No. 13/170,686, Walker et al., "Cofactor-dependent enzyme catalysis in functional dated May 9, 2014, 8 pgs. ized ionic solvents', Chemical Communications, 2004, pp. 2570 2571. * cited by examiner US 9,328,220 B2 1. 2 LIQUIDS carboxyl, boronate, silyl and Substitutedamino (e.g. mono- or di-alkylamino or alkyamido); and R' and R", which may be This application is a continuation application of U.S. appli the same or different, each represent H or R; or any two or cation Ser. No. 10/599,694, filed Jan. 19, 2007, which claims three of R. R' and R" may be joined together with the N to priority to International Application No. PCT/GB05/01364 form a cyclic group. filed on Apr. 7, 2005, each of which is hereby incorporated by The term "ionic liquid herein includes, but is not limited reference in its entirety. to, compounds consisting of ions and liquid attemperatures at The present invention relates to ionic liquids and uses which the compound is stable and the ionic liquids may have thereof. The invention also provides processes for the manu a melting point below 100°C., for example, below 25°C. and facture of ionic liquids. 10 optionally below 20°C. The boiling point of the ionic liquid Ionic liquids are compounds which are composed of ions may beat least 200°C.
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