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2) United States Patent 6a 03) my ay @ ws) (3) os) «2 G8) ‘Tran METHYL ISOBUTYL CARBINOL MIXTURE AND METHODS OF USING SAME Inveator: Bo L. Tran, Chicago IL (US) Assignee: Naleo Company, Naperville, IL (US) Notice: Subject to any disclaimer, the term ofthis pateat is extended or adjusted under 35 USC. 154(b) by O days This patent is subject to a terminal dis- claim, Appl. Now 137053825 Filed: Sun. 19,2012 Prior Publication Data US 201201117721 May 10,2012 Related US. Application Data Continuation-in-part of application No, 11/764.461 filed on Jun. 18, 2007, now Pat. No 8,123,082. Int. Cl BOSE 1/04 (2006.01) B0sD 1/008 (2006.01) BOSD IM (2006.01), us.cl, 209/166: 252/61 Field of Classification Search 200/166: 252/61 See pplication file for complete search history. 'US008302778B2 (10) Patent No. 4s) Date of Patent: US 8,302,778 B2 *Nov. 6, 2012 66) References Cited US. PATENT DOCUMENTS 137088 A +1991 Sayre 200166 yoo A+ S935 Paek doves DS00A2T § * 111942. Christman eal 200 166 Soran A T1913 Chemeb eta ROSSI A 41976. Schmit eal A207 AGIOS) Manger #500284 8 $2198) reson ea aos? S316s64 A $1994 Gropol eal So2s06 A 7/199) Rast etal Sioxow Ree 22012 Tram 2091166 * cited by examiner Primary Examiner — ‘Thomas M Lithgow (74) Attornes, Agent, or Firm —Benjamin E_ Carlsen: Andrew D. Sorenson on ABSTRACT Te invention is directed towards methods and compositions for sepamting materials are provided. The present invention provides a method of separating first material from a second Iaterial such as mixing the frst material and the second ‘material in a slunry with a beneliciation composition, The ‘benefciation composition can comprise meth isobutyl carbinol mixture derived fom & methy! isobutyl Ketone and ‘methyl isobutyl carina! manufacturing process. Adition- ally air bubbles can be provided in the slurry to form bubble particle aggregates with the first material and the bubble- particle agarepates can be allowed to be separated from the evondl material 15€ 1s, No Draw US 8,302,778 B2 1 METHYL ISOBUTYL CARBINOL MIXTURE AND METHODS OF USING SAME, (CROSS-REPERENCE TO RELATED "APPLICATIONS, ‘his Application is @ continuation in pat of US. patent application Ser. No, 11/764,461 now US, Pat, No, 8,123,042, filed on Jun, 18, 2007 STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT ‘Not Applicable. BACKGROUND OF THE INVENTION ‘The present invention relates generally to beneficiation technologies, More specifically, the present invention relates to heneficiation compositions and methods of using the same Benefication isa method of separating usefal matter fom waste. Commonly, beneficiation uses the difference in the hydrophobicity of the respective components. During this process, the mineral oes comminuted toa certsin smal size ‘and sluried with water. The slurry is introduced into a lo tion apparatus purged with az The ae bubbles formed prel- ‘erential attach (0 the hydrophobic particles ofthe slurry, ‘making them float tthe top of the apparatus. The floated particles are collected, dewatered, and accumlated as sell able final product, Thehydrophilc particles tend to migrateto the bottom of the contact vessel from where they ean be removed as slings and processed into waste impoundments Inother processes, such as everse Hotton, the sellable final product may migrate tothe bottom. “To facilitate benetciation, several types of conventional reagents are used such as frothers, collectors, promoters and ‘conditioners. Nevertheless, these reagents can be expensive thereby reducing the costeTectiveness ofthe benelieition processes. “Thus it is clear that there is clear uiity in novel methods and compositions forthe flitting beneficiation, The art described in this section is not intended to constitute aa admission that any patent, publication or other information referred to hereia i “Prior Ar” with respect to this invention, unless specifically designated as such, In addition, this sce tion should not be construed to meaa that a search has bee ‘made or that ao other pertinent information as defined it 37 CER §1.56(a) exists BRIEF SUMMARY OF THE INVENTION At least one embodiment of the invention is directed ‘owanls method of separating a fist material from a second material. The method comprises: Mining the first material ‘and the second material ina slurry witha eneficiation com- Position, wherein the boneficiation composition comprises.an MIBC mixture and at lest one C10 to C18 Ketone, Ain bubbles may be proved inthe shay to form bubble-particle ‘agarepates withthe fist material; ad allowing the bubble Particle aggregates tobe separated from the second meri "AL Teast one embodiment of the invention is directed towards method of separating a first material from a second material, the method comprising: Mixing the fist material and the second material ina slurry with a benefiiation com- Position derived from the manufacture of methyl isobutyl ketone of methyl isobutyl earinol, wherein the henefiinton ‘composition comprises one or more components selected 2 rom a group consisting of disobutyl carbinol and diisobutyl carbinol isomers ancl combinations thereof, and wherein the Dbenefciation composition comprises one or more ketone ranging from C10 to C18. DETAILED DESCRIPTION OP THE INVENTION ‘The following definitions are provided to determine hav terms used in this application, and in particular how the claims, ae to be construed. The onganizaton of the defini- ‘ions is for coavenience only’ and is not intended to Fit any of the definitions to any particular category. "Beneficition” means separating. useful matter fom \aste particularly hydrophobic substances from hydrophi substances, Suitable processes for accomplishing. this le, but are not limited to, flotation, reverse flotation and ilar technologies. "MIRC mixture” means co-products generated from MIBK andlor MIBC manufacturing processes. ‘By-Products means by-products derived from biodiese manufacturing processes, andor transesterification reactions involving triglycerides “OFT-Spce Material” cans products rom odie man facturing processes andiortransesterification reactions that do not meet industry quality standards because they are bot- ‘oms of processes, contaminated, by-products, and/or gener- ated from process wash out. The oflspee material can com- prise the same components as the by-products. In some ‘nstanees, the offspee material is mixed with the by-prod- vets, “Cineen Collector” means one of more components selected from a group consisting of nonionic surfetants of low HILB numbers, naturally occurring lpi, modified lp ids, hydrophobic polymers and combinations thereof. “Green” means environmentally rien, biodegradable, andor nontoxic chemistry Tn the event that the above definitions or @ description stated elsewhere in this application is incoasistent with a ‘meaning (explicit or implicit which is commonly used, in a ictionary, or stated ina source incorporated by reference into this application, the application and the elaim terms in par scala are understood to be construed accoting othe de sition or description inthis application, and not according to the common definition, dictionary definition, or the definition ‘that was incorporated by reference. In light of the above, ia the event that aterm can only be understood iit is consid by a dictionary, if the term is defined by the KireOthmer Eneyelopedia of Chemical Technology, Sih Edition, (2005), (Published by Wiley, John & Sons, Inc.) this definition shall centrol hav the term isto he defined in the claims. Flotation processes are one of the most widely used meth ‘ods of separating the valuable material rom valueless mate- lal present, For example, in a flotation provess, the fine particles are dispersed in water or other suitable solution and ‘Small sie bubbles are introdveed to the slurry so that hydro- ‘hobic particles ean be selectively collected onthe surface of the airbubblesandexitthe sury (eg. hy rising tothe surface) while hydrophilic particles ae lft behind. The hydrophilic particle ean also siak to the bottom ofthe shumy to be co lected as sludge. "The MIBKC mixture can be used to separate materials, for ‘example in any suitable flotation process. tshould be appre- ciated that the desired final products can rise tothe surface ‘during flotation andor sink to the bottom, such as in reverse ‘oration processes. For example, during silica flotation pro- cesses, the desired product can sink tothe bottom ofthe srry and the waste product ean rise tothe top ofthe slurry 0 o US 8,302,778 B2 3 The present invention provides 4 method of separating 3 first material rom a second material, In one embodiment the ‘method ean comprise mixing the fst material and thesecond material in a slimy with a beneficiation composition. The beneliciation composition can comprise a methyl isobutyl ‘carbinol (MIC) mixture. Air bubbles can be provided inthe shiny to form bubble-particle aggregates with the fist mate- rial and the bubble-particle aggregates can be allowed to be separated from the second material In one embodiment, the MIBC mixture contains MIBC, ‘alcohols, and Ketones. Tn another embodiment, the MIRC mixture ean be derived from the manufacture of methyl isobutyl ketone (MIBK) ‘andlor MIBC, The MIRC mixture is co-produced in the ‘manufacturing process The MIBC mixture comprises about $0 to about 90 weight pereent of MIBC, about $ t0 about 25 weight percent of ‘alcohols and about 5 to about 25 weight percent of Ketones in adlitional embodiments In an embodiment, the aleobols comprise one oF more ‘components selected from a group consisting of disobutyl ‘earinol and diisobuty!carbinol isomers and combinations thereat ‘nan emboxliment, the Ketones comprise one of more com= ponents selected from a group consisting of diisobutyl ketone, isobutyl ketone isomers and 3,3. timethyleyelo- hhexanone and combinations thereat Tn embodiment, the MIBC mixture ean be blend with ‘existing beneficiation compositions to improve effectiveness, Tn another embodiment, the present invention provides 3 ‘method of separating hydrophobic and hydrophilic particles ‘nan aqueous stuffy. Por example, the method can comprise ‘adding a beneficiation composition tothe aqueous slurry (0 ‘Stabilize the bubble formation The benefciation composition ‘can comprise a MIBC mixture derived from the maalactur jing of MIBK andlor MIBC. The hydrophobie particles attach ‘ont the surface ofthe stabilized air bubbles, forming bubble= particle aggregates that can Noat ta the surface ofthe aqueous slurry. “The present invention provides an effective methods of separating to or more materials. The present invention also provides compositions sed to Stabilize air bubbles in flotation processes resulting in improved results ‘The present invention relates generally (0 beneficiation technologies. More specifically the present invention relates to heneficiation compositions and methods of using said ben- eficiaion composition The present invention provides a benefciation compos! tions comprising co-praducte from MIBK andlor MIBC manufacturing processes. The co-productscaneomprise mix- tures of MIBC and other alcohols and ketones, The aleobols and ketones contain primarily from nine t0 swenty carbon "The MIBC mixture ofthe present invention suprisingly Improves recovery of beneficiation technologies, for ‘example, flotation processes. The MIBC mixture can be wsed {o supplement or replace conventional beneficiation compo- sitions used in lotation processes ‘Generally, MIBK is produced Irom acetone. The fist step involves the aldol condensation to form diacetone aleohol. ‘The diacetone then dehydrated to form mesityoxide. Inthe last step the mestyl oxide is hydrogenated to MIBK. Theo- retical yield is about 89%. Varying amounts of MIBC mix- tures are co-prodiced. MIBC is generally prociced by the hydrogenation of MIBK. 0 o 4 [MIBK is used primarily asa solventin the coating industry. (MIRC is used primarily a «lube oil additive. MIBC is also Widely used a8 a frother in Hotation peocesses recovering ‘minerals. MIBC stabilizes the bubbles allowing the hydeo- hobic minerals to attach themselves tothe bubbles. low ever, MIRC cost has esalated recently duc tothe high cst of petroleum hydrocarbons, The present invention offersan eco- ‘omical alternative that i elfetive fora variety of henficia- sion technologies, Tnoneembodiment, the MIBC mixture from MIBK manu ‘cturing can comprise of MIBC, other alcohols and Ketones, The alcohols and ketones can include diisobuty] carbinol, diisobuty] Ketone, and 3,3,5 twimethyleyelohex- ‘anone, and their isomers The above composition suggest that the MIBC mixture ‘can make a perfect flotation reagent. In loation lab tests the [IBC mixture was eflective in stabilizing air bubbles. In an altematve embodiment, the MIBC mixtures ean {urtherbe mixed withadditives to supplement and/or improve the separation properties ofthe beneficiation compositions. Such adklitves con include other Rotation reagents. Other Foation reagents include but are not Himited to ight hydro- carbon oils, petroleum ethers, fatty acid methyl esters, fatty ‘acids, ¢4-€20 alcohols, o4020 aldehydes, ¢4-c20 esters, phosphate, sulfate, sulfonate, amine salt, xanhates,hydeo- phobic polymers, andl combinations thereot ‘he hydrophobic polymers ean inchude, for example, poly methyihlrosiloxanes,polysilanes, polyethylene derivatives, ‘and hydrocarbon polymers generated by both ring-opening ‘metathesis and methalocene eatalyzed polymerization, "The light hydrocarbon oils include diesel ol, Kerosene, gasoline, petroleum distillate, turpentine, naphtanie oils, ete Tn a further embodinient, the present invention, provides methods of stabilizing the hubbies in certain beneficiation processes. For example, the beneficiaton composition com- prising the MIBC mixture can be usefil in beneliciation of the following materials including, bat not limited to coal, sand ‘nd gravel, phosphates, diamonds, precious meals, and other ‘mineral ores of manmade matter. In alternative embodi- ‘ments, the benefciation composition can heused in processes to increase the bubble stability, particulary im applications such as flotation resulting in the benefciation of eoal, sand and gravel, phosphates, diamonds, precious metals, and other ‘mineral oes or man-made matte. The beneficiation compo- lion can also be used in conjunction with tbe suitable others, flotation collectors and promoters ‘An additonal embodiment of the present invention pro- vides a method of separating a first material from a second ‘matecal. For example, the method ean comprise mixing the fist material and the second material ina shay with a ben- cicition composition, The heneficiation composition can comprise MIBC mixtures derived Irom a MIBK. or MIBC ‘manufacturing process, Air bubbles caa be provided in the slumy to form bubble-parcle agzregates with the frst mate- ‘al; the bubble-paticle aggregates can then be separated from the second material The benefciation composition ean further include other frothers, promoter, and/or collector mixed withthe MIBC mixture The present invention additionally provides a method of separating hydrophobic and hydrophilic particles in an ague- ous slury. For example, the method can comprise adding & bbeneficiation composition to the aqueous shury to inerease the stability of the bubbles, The benefciation composition can comprise MIBC mixtures derived from MIBK of MIRC ‘manufacturing process. The aqueous slury can be mixed ‘with the MIRC mixtures. Nie bubbles can be provided to the aqueous slurry sothat the hydrophobic particles colleet onthe US 8,302,778 B2 5 surface of hear bubbles forming bubble-particleauprepates. The bubble-particle agaregates can be allowed to float to the surface ofthe aqueous sutry tobe separated from the hydro- Philc particles. "The materials be separated canhaveanystitablesize. By ‘example and aot limitation, the materials can ange fom 2 ‘mm (0 0.04 mm in siz. The slury ean contain up to 50% solids. Any suitable mechanical or chemical forees can be used to bring the slury particles in conteet with the benet- ‘ciation compositions of the present invention. The floated product and the non-osted tailings can becolleted from the present methods. ‘Some prior art methods and/or compositions relevant 10 bbeneficiation include US. Pat. Nos. 5,316,664, 3,675,773, ‘and 4,208,487. The instant invention differs from these in 3 number of ways. Ina least oneembodiment the henefiiation method exchides the wse of C9 Ketones, In at least one ‘embodiment the beneficition method excludes the use of ketones having 9 oF fewer carbon atoms, In at least one ‘embodiment the benefiiation method excludes the presence (0f2.68 trimethyl-4-nonanone. EXAMPLES The foregoing maybe better understood by referenceto the following examples, whieh are presented for purposes of ‘ustration and are-not intended to limit the seope of the invention, Tn example | the beneficition composition ofthe present Jnvention comprises ablend ofthe MISC mixturesand I-pro- pene hyoformlation product, The [-propene hyedeofoemy Tation productisa mixture ofthe C4-C18 alcohols aldehydes and esters, and is generally used as a frother in tation ‘operations. The beneficiation composition is prepared rom, about 30% by weight of the MIBC mixtures and 70% by ‘weight of I-propene hydroformylation product. Tt was come pared against another flotation reagent consisting of 30% hy ‘weight of MIRC and 70% by weight of T-propene hydo- qomiylation product “A sample of coal slurry from a coal preparation plant was Aoated in the laboratory using a Denver flotation machine ‘The tests were designed to determine the ult ofthe MIBC. mixture blended with a -propene hydroformylation product. The collector used was diesel. The MIBC mixture was the ‘obtained from the manufacture of MIBK and MIBC. Example 1 Sytermitce Prepon ne ‘ele 63) we tae st cv ane tate at ms Ge “The above data shows combustible recovery uaproved when, utilizing the MIBC mixture, Pxample 2 “The MIBC mixture was used in place of MIBC at eval Aoation process facility in whieh the recovery of fine coal noticeably increase from about 85% to 89% withthe we oF the claimed invention, 0 o ‘While this invention forms, there described in detail herein specific prelerred embodiments ofthe invention, The present disclosure is an cexemplfiation of the principles of the invention and is no, ‘intended o limit the invention tothe particular embodiments illustrated. All patents, patent application, scientific papers fand any other referenced materials mentioned herein are Incorporated by relerence in thee entirety. Purlhermore, the invention encompasses any possible combination of some or all of the various embodiments described herein and incor porated herein. In aldtion the invention encompasses ay possible combination that also specifically excludes any one fr some of the various embodiments described heecin and incorporated herein. The above disclosure i intended tobe illustrative and not exhaustive, This description wllsugzest many variations and altematives to one of ordinary skill in this art All these fltematives and variations are intended toe incaded within the scope of the claims where the term “comprising” means “including, but not Hmited to. Those familiar wilh the at ay recognize other equivalents othe specific embodiments described herein which equivalents ae also intended to be tencompassed by the claims, ‘Allanges and parameters disclosed herein are understood to encompass any and all subranges subsumed therein, and every number between the endpoints. For example, a stated range of" to 10° should be considered to include any and all subranges between (and inclusive ofthe minimum valve of | And the maximum value 10; thats all subranges beginning ‘witha minimum, vaueof lormore, eg, 1106.1),andending ‘witha maximum value of 10 oF less, (@.23109.4,3 108.4 07), and finally to each number 1,2,3,4,5,6,7,8,9,and 10 ‘contained within the rang. This completes the description of the prefered and alter- tate embodiments of the invention, Those skilled inthe at ‘may recognize other equivalents to the specific embodiment described herein which equivalents are intended to be encom- passed by the claims ataehed hereto. ‘What is claimed is 1. A method of separating first material from a second ‘material, the method comprising’ mixing the fist material ‘and the second material in a slur with a benefication com- positon, wherein the beneficiation composition eomprisesan ‘MIRC mixture and the MIRC mixture comprises MIC, at Teast one C10 to C18 Ketone, 2,6,8rimethy!-4-nonanone, ‘nd one item selected rom the list consisting of 2.6-dim- ethyl-4heptanol, 2,6

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