(12) INTERNATIONAL APPLICATION PUB (19) World Intellectual Property 5 Organization Z = International Burau = (43) International Publication Date UNDER TH PATENT COOPERATION TREATY (PCT) AAO 0 (10) International Publication Number WO 2021/009774 Al wo 2021009774 A. /IIIMINN MMII 21 January 2021 (21.01.2021) WIPO! PCT (6) International Potent Cheatin: (7) Inventor: RANGASWAMY, Parthasarathy, Thrall Core 13si2in6 01) "TL OuaretsRanpet, Tam Nad, Ven 632408 N). (21) International Application Number: (14) Agen LAKSHMIKUMARAN, Malate l; B/o, (2) tneratonl Fling Date: See 1s iy-2020,18072020) Rado maton! proweton ull AE. AG. AL AMT ing Languages ‘ghish CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, Publication Language: Bngsh BZ. EC. EE“EG.ES.T1 Go, Gb. GE Gil GM. GTN ee Hf HU MD, INR 1S 17,3, J KE, KG. KERN Priority Data: 1s 2019 sor 2019 KP.KR, KW. KZ, LA LC,LK,LR, LS, LU, LY, MA, MD, 2orpztoaseso 6 Ju 201946072019) IN Ne MN, AW MMV, Ma, NA, NG, NNO 2021009475 05 March 2020 (05.03.2020) NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, (7) Applant: THIRUMALAT CHEMICALS LiMITeD —SA'SC-8b, SE, 8K SL. ST SV. SY. HLTH. TM, TN TININT Thin ouse Do No T0LH02 RoadNe 29, TRTT-T2:UA.UG,US.UZ, VC, VNWS,ZA.ZM.2W. Sion as, Mba #0622), iy Tine PRODUCTION OF MALIC ACID - ue Anhystide cred ea = (aa, SS a >} ie Fam ase | Srnout Tubvtar = (oure) =] | catalyst) (continuous, Ly anmytrie 28 7 eel | | 7 Belg [38 catalyst) Safco ates Acid forude} Hatiza00n >| trestment [Ot sat | Vent gas | ss eres L_. om ase pore) 1126 ‘uenun ‘tied tant 4320 ‘borate reactor ots L, ess waeet see Fig. 1 (67) Abstract: A method of production of malic acid includes treating 2 frst intermediate product to forma second intermediate product. The treating includes substantially removing impurities from the first intermediate product to obtain a trated intermediate product by ‘gas stripping the crude maleic anhydride, or subjecting a mixture of one or more ofthe crude maleic acid, the crude fumaic acid, ‘and the vent gis serubber solution obtained from a plialic aaltydride production process or a maleic anhydride production process 1o crystallization, passing an aqueous solution of the treated intermediate product through a carbon coluni to substantially remove retained impurities to form the second intenmediate product, obtaining a feed that includes the second intennediate product, and causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid [Continued on next page}WO 2021/009774 A. [MINNILLO EEA (84) Designated States fanless otherwise indicated, for every ind of regional protection available): ARIPO (BW, Gli, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, 82, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TI, ‘TMD, European (AL, AT, BE, BG. CH, CY, CZ, DE, DK. EE, ES, Fl, FR, GB, GR. HR. HU, IE. IS, IT, LT. LU, LY. MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI. SK, SM, ‘TR), OAPI (BF, BI, CF, CG, Cl, CM, GA, GN, GO, GW, KM, ML, MR, NE, SN, TD, TO), Declarations under Rule 4.17: = ofimventorship ale 4.1700) Published: = with international search report étrt. 21(3)) = in black and white: the imternational application as filed comained color or grevscale and is aveitable for download {from PATENTSCOPEWO 2021/009774 PCT/IN2020/050608 20 30 PRODUCTION OF MALIC ACID ‘TECHNICAL FIELD [0001] The present subject matter relates generally to the production of malic acid, and in particular to the production of malic acid from different feedstock starting from butane, benzene, ortho-xylene, naphthalene or from intermediate products obtained by the processing of butane, benzene, ortho-xylene, naphthalene. BACKGROUND [0002] Mal acid, which is prepared by the dissolution of maleic anhydride in demineralized acid is traditionally manufactured by the hydration of maleic water, or using a mixture of maleic acid and fumaric acid under conditions of high pressure and high temperature. The time taken to attain equilibrium, ie., formation of an equilibrium mixture of malic acid, fumaric acid, and trace amounts of unreacted maleic acid, which is considered as the time to reach completion of the reaction for a given quantity of maleic acid or its isomer fumaric acid or a mixture thereof, varies from 4 to 8 hours. [0003] Catalysts have been found to inerease the productivity of malic acid in the aqueous hydration of maleic acid. In a typical hydration reaction, maleic acid is hydrated in the presence of various catalysts, including sulfuric acid, [0004] U.S. Patent No. 3,379,756 describes a process for the synthesis of malic acid from maleic acid, fumaric acid, and mixtures thereof in an aqueous reaction mixture at elevated temperature and pressure, wherein the process is performed in a reactor zone whose surfaces that are exposed to the reaction mixture consist of at least one material from the group of titanium, zirconium, tantalum, and alloys containing at least one of the said material. 0005] USS, Patent No. 5,210,295 discloses a process for the hydration of an acid selected from maleic acid, fumaric acid and others, where the high temperature reaction is done in the presence of sodium ions in specified molar ratios. [0006] In European Patent No. EP0515345, there is a mention of "New by N. A. Bzhasso and M. P. Pyatnitskii, Catalysts for Hydration of Maleic A Zhur. Priklandnoi Khim., Volume 42, no. 7, pages 1610-1614 (1969) which reportsWO 2021/009774 PCT/IN2020/050608 10 25 that the hydroxides of aluminum and chromium, when added to aqueous solutions of maleic acid, increase the conversion of maleic acid to malic acid. Equilibrium amounts of fumaric acid were also found in the hydration product. It is further stated that the published Russian patents by the said authors, viz. USSR Patent Nos. 208706 and 218874, had disclosed the hydration of maleic acid to malic acid by dissolving maleic acid in water and adding aluminum hydroxide, chromium sulfate or aluminum chloride as catalysts for the reaction. The use of chlorides and sulfates of aluminum result in the formation of acids, i.c., hydrochloric acid and sulfuric acid, respectively. This leads to severe corrosion in the reactor vessel due to the contact of these acids with the metal surface, especially in the downstream of the reactor, which contaminates the products. Further, these ions, namely, chlorides and sulfates of aluminum are highly soluble and have to be removed by ion exchange or by other expensive methods. The use of chromium hydroxide results in the formation of poisonous chromium malate, in addition to imparting color to the mother liquor. The chromium malates get concentrated in the mother liquor over a period of time and can precipitate along with the product and contaminate the product 10007] U.S. Patent No. 3.379.757 discloses a process for the manufacture of malic acid from aqueous solutions of maleic acid resulting from the vapor phase catalytic oxidation of an organic compound such as benzene comprising ageing the resulting maleic acid solution in the presence of air, filtering the aged solution and heating the filtrate in a closed system under super atmospheric pressure to convert the maleic acid to malic acid. This ageing process is carried out in a rubber lined steel tower [0008] However, the conventional methods of production of malic acid have several disadvantages. Very high temperatures and pressures are required for the reaction, it takes a long time for the reaction to reach equilibrium, the reaction products are corrosive and poisonous leading to corrosion of reactor vessels, and additional processes are required for removing contaminants from the products, leading to higher capital and operating costs. Accordingly, a need exists for alternative methods for the manufacture of malic acid.WO 2021/009774 PCT/IN2020/050608 10 25 SUMMARY 10009) Disclosed herein is a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process and combinations thereof, and wherein or a maleic anhydride production proce: the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (ii) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumari and the vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (a) obtaining a feed comprising, the second intermediate product; and (b) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid. [0010] In some embodit rents, the feed may be reacted in the presence of a the atalyst. In. some embodiment alyst may be selected from a group consisting of aluminum metal, borate salt of aluminum, and carbonate salt of aluminum, [0011] In some embodiments, the catalyst may have a concentration in a range of about 50 mg/L to about 500 mg/L with respect to the crude maleic anhydride or equivalent in the feed. 10012] In some embodiments, the size of the catalyst particles may be ina range of about 10 micron to about 800 micron [0013] In some embodiments, the feed to catalyst ratio may be in a range of about 1:0.00005 to about 1:0.0005. 10014] In some embodiments, the method disclosed here comprises obtaii ning a raw material selected from a group consisting of butane, benzene, o-WO 2021/009774 PCT/IN2020/050608 10 25 xylene, naphthalene, and combinations thereof. In some embodiments, the raw material may be processed to obtain the first intermediate product. 0015) In some embodiments, gas stripping the crude maleic anhydride may comprise one of: passing nitrogen through heated crude maleic anhydride under vacuum to substantially remove the impurities; or passing air through heated crude maleic anhydride to substantially remove the impurities. In some embodiments, the step of passing air through heated crude maleic anhydride to substantially remove the impurities may be performed in a column. In other embodiment. gas stripping the crude maleic anhydride may comprise passing carbon dioxide through heated crude maleic anhydride under vacuum to substantially remove the impurities. In ir can be about 0.5 Nm‘/h to about 20 Nav’/h, or 0.5 Nm‘Vh to about 10 Nm‘Vh or 1 Nm’/h to 5 Nm'/h, such as 3 Nm’Vh, some embodiments, the flow rate of the In some embodiment . temperature of the column may be about 70°C to about 100°C, such as about 75°C to about 95°C, or about 90 °C. [0016] In some embodiments, tubjecting the mixture to crystallization may comprise: cooling the mixture to a temperature below about 30°C, below about 25°C, or below about 15°C, such as about 10 degrees, Celsius in a plurality of stages to obtain crystals of maleic acid; and filtering out the crystals of maleic acid as the treated intermediate product. (0017) In some embodiments, obtaining a feed may comprise mixing the second intermediate product with one or more of water, maleic acid, maleic anhydride, and fumarie acid. 10018] In some embodiments, causing the feed to undergo hydration reaction may comprise passing the feed in the tubular reactor at a Reynold’s number from about 2900 to about 10000, and preferably from about 5000 to about 7000. In some embodiments, the feed may be reacted at a temperature in a range of about 135-195 °C and a pressure of about 11-15 bar for about 1 to 2 hours. In some embodiments, the tubular reactor may be operated in one of a batch, semi- continuous, or continuous mode. 10019) In some embodiments, in the batch mode, a solution comprising the products may be drained out completely after completion of reaction.WO 2021/009774 PCT/IN2020/050608 10 25 10020} In some embodiments, in the semi-continuous mode, a part of the solution comprising the products may be removed after a predetermined period of time and an equal quantity of feed may be fed into the tubular reactor. 10021] In some embodiments, in the continuous mode, a part of the solution comprising the products may be continuously removed and simultaneously the same quantity of feed may be fed into the tubular reactor BRIEF DESCRIPTION OF DRAWINGS 10022] ‘The detailed description is described with reference to the accompanying figures. In the figures, the left-most digit(s) of a reference number identifies the figure in which the reference number first appears. The same numbers are used throughout the drawings to reference like features and components where possible. [0023] Fig. | illustrates a flow chart of the process of malic acid production in accordance with an embodiment of the present disclosure. [0024] Fig. 2 is a schematic illustration of a continuous tubular reactor system for production of malic acid, in accordance with an embodiment of the present disclosure. 10025] Fig. 3 is a schematic illustration of a semi-continuous tubular reactor system for production of malic acid, in accordance with an embodiment of the present disclosure. 10026] Fig. 4 isa schematic illustration of a batch tubular reactor system for production of malic acid, accordance with an embodiment of the present disclosure. [0027] Fig. 5 is a schematic illustration of a stirred tank reactor for production of malic acid, in accordance with an embodiment of the present disclosure DETAILED DESCRIPTION (0028) ‘The present subject matter relates to the production of malic acid from different raw materials or feedstock and their mixtures in different modes of operation with and without the using catalysts,WO 2021/009774 PCT/IN2020/050608 10 25 [0029] Traditionally, malic acid is commercially produced using pure maleic anhydride obtained by the distillation of crude maleic anhydride, or from pure fumaric acid. The crude maleic anhydride or crude fumaric acid are obtained by vapor phase oxidation/gas phase oxidation of organic compounds such as butane, benzene, furan, furfural, and the like. The gaseous mixture of mainly maleic anhydride released from the outlet of the reactor is cooled in a condenser to obtain his crude mak a solid material, wl known as crude maleic anhydride. c anhydride is subjected to distillation to produce pure maleic anhydride. The uncondensed gases exiting the condenser are scrubbed in water to produce crude maleic acid, called as scrubber solution. This maleic acid scrubber solution is further subjected to dehydration and azeotropic distillation with o-xylene followed by vacuum distillation to produce pure maleic anhydride. The pure maleic anhydride is then used for the production of malic [0030] However, purification of maleic anhydride is very expensive, and using the pure form of maleic anhydride leads to a great inerease in the cost of malic acid production. Furthermore, this also adds to the time required for the production of malic acid. Production of pure maleic anhydride also involves considerable loss of maleic anhydride during purification. The method of production of malic acid of the present disclosure overcomes the problems and disadvantages associated with conventional methods of production of matic acid, The present disclosure relates to a method of production of malic acid and co-production of fumaric acid from butane, benzene, o-xylene (raw material), or from any other intermediate products formed during the production of maleic anhydride or phthalic anhydride in an integrated production process. Crude products formed during production of maleic anhydride, phthalic anhydride, maleic acid, fumaric acid, and the other similar compounds, and uncondensed vent gases recovered by dissolving in water, generally called scrubber solution, can be used, in addition to using the pure forms of these products as the raw materials. In one example, for purification of intermediate products, any one or more of the following processes known to those skilled in the art can be followed: adsorption, absorption, spray drying techniques, falling film evaporation. The method of production of malic acid of the presentWO 2021/009774 PCT/IN2020/050608 10 25 disclosure includes a simple treatment of the raw materials, which eliminates the ced for the less eco-friendly and more expensive dehydration and distillation steps traditionally used in the purification of raw materials or intermediates. The production can be done in continuous, semi-continuous, batch modes, or any combination thereof. In one embodiment, the reactor used is a tubular reactor operated in continuous, semi-continuous, or batch mode. The process of the present disclosure can be carried out in a tubular reactor of suitable design to prevent plugging and promote high rate of conversion by maintaining a turbulent flow with Reynold’s number in the range of 5000 to 7000. In the process of the present disclosure, there is no back-mixing in solution flow in the tubular reactor. This enhances the rate of reaction to achieve faster equilibrium conditions. Consequently, in the process of the present disclosure, there is a substantial ) leading to increased productivity. In some embodiments, the flow in the reactor reduction in cost, energy and duration to achieve equilibrium (reaction how can have Reynold’s number from about 2900 to about 10000, from about 3000 to about 9000, from about 4000 to about $000, from about 5000 to about 8000, from about 5000 to about 7000, from about 5500 to about 7000, or from about 6500 to about 7000. In some embodiments, the Reynolds number may be, for example, at least 2500, 3000, 3500, 4000, 4500, 5000, 5500, 6000, 6500, 7000, 7500, 8000, 8500, 9000, 9500, 10000, or within a range defined by any two of the aforementioned Reynolds numbers. 10031] In another embodiment, the reactor is a stirred tank reactor. The reaction is performed in the presence of aluminum borate catalyst, which leads to lesser time required to achieve equilibrium compared (o conventional methods and thus increases productivity. Nevertheless, a catalyst is not necessary in many embodiments described herein [0032] Further, the method does not require pure raw materials, as required in conventional methods, thus reducing costs significantly. The method also reduces the amount of effluent to be treated during production of pure maleic anhydride or pure maleic or fumarie acids. The method also reduces the time for the reaction to 1-2 hours. The redu ion in time reduces the energy consumed duringWO 2021/009774 PCT/IN2020/050608 10 15 25 operations and thus reduces operating costs. In some embodiments, impurities may be present at 0.1% w/w, 0.2% whw, 0.3% w/w, 0.4% wiw, 0.5% w/w, 0.6% wiw, 0.7% wiw, 0.8% wiw, 0.9% whw, 1% wiw, or more of the raw materials. In some embodiments, the impurity may be acetic acid, acrylic acid, or a combination thereof. [0033] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride: or (ii) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumarie acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtaining a feed comprising the second intermediate product; and (¢) causing, the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid. [0034] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber soli n obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the 1 substantially removing ‘ating comprises impurities from the first intermediate product to obtain a treated intermediateWO 2021/009774 PCT/IN2020/050608 10 25 product by: (i) gas stripping the crude maleic anhydride; or (ii) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumarie acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; ing (b) obtaining a feed comprising the second intermediate product; and (c) ¢: the feed to undergo hydration reaction in a tubular reactor to produce malic acid. [0035] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (i) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumaric acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process to crystallization; and pas ora maleic anhydride production pro ing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtai ng a feed comprising the second intermediate product; and (c) causing the feed to undergo hydration reaction in a continuous stirred tank reactor to produce malic acid. 10036] In another embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) obtaining a raw material selected from a group consisting of butane, benzene, o-xylene, naphthalene, and combinations thereof; (6) processing the raw material to obtain the first intermediate product; (c) treating the first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from aWO 2021/009774 PCT/IN2020/050608 10 25 group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by gas stripping the crude maleic anhydride; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second termediate product; (d) obtaining a feed comprising the second intermediate product; and (¢) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid. 0037] In yet another embodiment, the present subject matter includes, a method of production of malic acid, the method comprising: (a) obtaining a raw material selected from a group consisting of butane, benzen o-xylene, naphthalene, and combinations thereof; (b) processing the raw material to obtain the first intermediate product; (c) treating the first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumarie acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by subjecting a mixture comprising one or more of the crude maleic acid, the crude fumarie acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (@) obtai 1g a feed comprising the second intermediate product; and (e) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid. 10038] In an embodiment, the present subject matter includes a method of 1 production of malic acid, the method comprising: (a) obtaining a raw materi 10WO 2021/009774 PCT/IN2020/050608 10 25 selected from a group consisting of butane, benzene, o-xylene, naphthalene, and combinations thereof; (b) proces: ig the raw material to obtain the first intermediate product; (c) treating the first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate in a treated interme product to obt ale product by gas stripping the crude maleic anhydride; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (d) obtaining a feed comprising the second intermediate product; and (e) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid. 10039] In yet another embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production proces or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride comprises passing nitrogen through heated crude maleic anhydride under vacuum to substantially remove the impurities; or passing air through heated crude maleic anhydride to substantially remove the impurities or (ii) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumarie acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ora maleic anhydride production process to crystallization; ind passing an aqueous solution of the treated intermediate product through a carbon column to substanti: ly remove retained impurities to form the second intermediate product; uWO 2021/009774 PCT/IN2020/050608 10 25 (b) obtaining a feed comprising the second intermediate product; and (c) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor to produce malic acid, Passing air through heated crude mal c anhydride to substantially remove the impurities may be performed in a column, wherein the flow rate of the air is from about 0.5 Nm/h to about 20 Nm°/h, preferably from about 0.5 Nm'/h to about 10 Nm'/h. The temperature of the column may be from about 70 °C to about 100°C, such as about 75°C to about 95°C, or about 90 °C. In other embodiment, gas stripping the crude maleic anhydride may comprise passing carbon dioxide through heated crude maleic anhydride under vacuum to substantially remove the impurities. [0040] In a further embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated termediate product by: (i) gas stripping the crude maleic anhydride; or (i) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumaric acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process (o crystallization comprises: cooling the mixture to a temperature below about 15 degrees Celsius in a plurality of stages to obtain crystals of maleic acid; and filtering out the crystals of maleic acid as the treated intermediate product; and pi ng an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtaining a feed comprising the second intermediate product; and (c) causing the feed to undergo hydration reaction in a tubular reactor ora continuous stirred tank reactor to produce malic acid. In another embodiment, the mixture may be cooled to a temperatureWO 2021/009774 PCT/IN2020/050608 10 25 below about 10 degrees Celsius in a plurality of stages to obtain crystals of maleic acid. (0041) In one embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (i) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumaric acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtaining a feed comprising the second intermediate product comprises mixing the second intermediate product with one or more of water, maleic acid, maleic anhydride, and fumaric acid; and (c) causing the feed to undergo hydration reaction ina tubular reactor or a continuous stirred tank reactor to produce malic acid. [0042] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (ii) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumaric acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process 13WO 2021/009774 PCT/IN2020/050608 10 25 ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermedi (b) obtai te product; ng a feed comprising the second intermediate product; and (c) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor at a Reynold’s number from about 2900 to about 10000 to produce malic acid. [0043] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride produ. In process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (ii) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumarie acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtaining a feed comprising the second intermediate product; and (©) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor at a Reynold’s from about 5000 to about 7000 to produce malic acid. [0044] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumarie acid, vent gas scrubber solution obtained from a phthalic anhydride production process or a maleic anhydride production process, and combinations thereof, and wher the treating comprises: substantially removing 14WO 2021/009774 PCT/IN2020/050608 10 25 impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (ji) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumarie acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtai 1g a feed comprising the second intermediate product; and (c) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor in the presence of a catalyst at a Reynold’s number from about 2900 to about 10000 to produce malic acid 10045] In an embodiment, the present subject matter includes a method of production of malic acid, the method comprising: (a) treating a first intermediate product to form a second intermediate product, wherein the first intermediate product is selected from a group consisting of crude maleic anhydride, crude maleic acid, crude fumaric acid, vent gas scrubber solution obtained from a phthalic anhydride produe n process or a maleic anhydride production process, and combinations thereof, and wherein the treating comprises: substantially removing impurities from the first intermediate product to obtain a treated intermediate product by: (i) gas stripping the crude maleic anhydride; or (ji) subjecting a mixture comprising one or more of the crude maleic acid, the crude fumaric acid, and the vent gas scrubber solution obtained from a phthalic anhydride production process ‘ora maleic anhydride production process to crystallization; and passing an aqueous solution of the treated intermediate product through a carbon column to substantially remove retained impurities to form the second intermediate product; (b) obtaini 1g @ feed comprising the second intermediate product; and (c) causing the feed to undergo hydration reaction in a tubular reactor or a continuous stirred tank reactor in the presence of a catalyst selected from a group consi ng of aluminum metal, borate salt of aluminum, and carbonate salt of aluminum at a Reynold’s number from about 2900 to about 10000 to produce malic acid. 15