PROSES INDUSTRI KIMIA II NITRATION
Disusun Oleh:
TEZA NUR FIRLYANSAYAH (115061102111001)
TEKNIK KIMIA UNIVERSITAS BRAWIJAYA MALANG 2013
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A. Pendahuluan
Reaksi nitrasi berfungsi untuk memperkenalkan satu atau lebih kelompok nitro( NO2) menjadi molekul bereaksi. Kelompok nitro mungkin menjadi melekat pada karbon untuk dari nitroaromatic atau nitroparaffinic. Dalam proses nitrasi kelompok nitro masuk dapat mengganti jumlah atom monovalen yang berbeda atau kelompok atom. Beberapa alkil halida dapat bereaksi dengan nitrat perak untuk dari ester nitrat yang sesuai atau dengan nitrit perak untuk dari yang sesuai senyawa nitro seperti yang ditunjukkan di bawah ini.
Pada seri aromatik asam sulfonat atau gugus asetil dapat, di tertentu dalam sikap, diganti seperti yang ditunjukkan dalam persamaan yang menyertainya.
Nitrasi adalah satu yang paling penting reaksi dalam industri sintetik kimia organik. tidak hanya produk nitrasi menemukan aplikasi luas sebagai pelarut, zat warna, obat-obatan, dan bahan peledak, tapi mereka juga melayani sebagai intermediet berguna untuk prepation senyawa lainnya. B.
Nitrating Agents
Sebuah variasi reagen dapat digunakan sebagai efek nitrasi. Ini termasuk penguapan, terkonsentrasi, dan pengenceran asam nitrit dengan sulfur, asetat anhidrida, asam asetat, asam fosfor, dan kloroform. 1
1. The Nitryl Ion, NO2+ . The nitrat sistem asam-asam sulfat, biasanya dikenal sebagai asam campuran, adalah media penitrasi paling penting dari sudut pandang praktis dan mungkin juga yang terbaik dipahami. Dari beku-titik pengukuran depresi, Van't Hoff ɩ faktor (jumlah partikel yang dihasilkan oleh satu molekul zat terlarut) asam nitrat dalam asam sulfat ditemukan menjadi 4, yang menunjukkan bahwa ionisasi asam nitrat dapat diwakili oleh persamaan
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Masing-masing solusi adalah agen penitrasi kuat Larutan asam nitrat memiliki tiga diferent ultraviolet-penyerapan spektrum. Dalam larutan encer, sptctrum adalah bahwa dari ion nitrat, NOs. Dalam inert lemah pelarut polar seperti kloroform, spektrum adalah sama dengan nitrat etil, menunjukkan bahwa asam nitrat ada sebagai unionizcd HNO3. Sebuah spektrum ketiga adalah karakteristik dari larutan asam sulfat asam nitrat dan esternya, menunjukkan bahwa di sini asam nitrat tidak ada sebagai ion nitrat atau serikat asam nitrat. Spektrum asam nitrat dalam asam sulfat bahkan lebih informatif. Ion nitryl, menjadi 'isoelektronik dengan karbon dioksida dan ion azida, N3-, harus menjadi ion centroeymnietric linear, maka spektrum Raman yang harus terdiri dari satu baris yang kuat dan polariscd. Dari getaran uencies dikenal freq Raman dari C02 dan N3-baris ini harus memiliki frekuensi yang agak lebih besar dari 1.320 cm-1. Solusi asam nitrat dalam asam sulfat dan asam perklorat hanya memiliki satu jalur karena raman asam nitrat yang terjadi pada 1.400 cm-1 dan yang terpolarisasi. Fakta bahwa ion yang berasal dari asam nitrat dalam asam sulfat adalah posisi. Hidup dibebankan telah dibuktikan oleh percobaan elektrolisis di mana ditemukan bahwa pengaya nitrat bermigrasi b ermigrasi dari anoda ke katoda. Akhirnya, perlu dicatat dic atat bahwa b ahwa beberapa + garam kristal tutryl telah isol diciptakan dan ditandai, e.g., NO2 ,‟N03, NO1‟CIO4 , and + NO2 ,HS2O7. Hubungan antara jumlah air yang hadir dalam asam sulfat dan persen dari molekul asam nitrat yang terionisasi membentuk ion nitryl ditunjukkan pada Gambar. 412. Dalam solusi lemah dari 86 persen asam sulfat, ionisasi dari asam nitrat sangat sedikit tapi cepat meningkat sebagai asam sulfat menjadi lebih terkonsentrasi. Pada sekitar 94 persen asam sulfat, asam nitrat praktis sepenuhnya terionisasi untuk ion nitryl.
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1
Molekul, radikal, dan ion yang memiliki jumlah yang sama dari atom dan elektron valensi disebut ieoelectronic. Spesies yang isoelektronik memiliki bentuk yang sama,. Sehingga sejak CO3, dan N2-, yang linear dan oentroeymmetxic, Ion
2
BONZER and Williams, Chemistry & Industry, 1961, 820.
Ion Nitryl juga telah terdeteksi di spektroskopis 100 persen asam nitrat, namun konsentrasi mereka sangat rendah. Pada -40 ° C, asam nitrat dikatakan mengandung 1,2 persen NO2 +, 1,7 persen NO3-, dan 0,5 persen Asam nitrat dalam anhidrida asetat dan anhidrida nitrat dalam 100 persen asam nitrat telah terbukti menghasilkan NO2 + dan N03-. C. Nitration Aromatic
Nitrasi senyawa aromatik dapat diwakili oleh persamaan
Orientasi. Agen nitrasi adalah reaktan elektrofilik, maka rea ksi akan disukai pada atom karbon dari cincin aromatik mana kerapatan elektron yang besar. Ketika senyawa aromatik untuk nitrasi mengandung substituen, kelompok nitro bisa masuk pada posisi orto, meta, atau para. Jumlah relatif dari produk isomer akan DEP endupon substituen, karena substituen memiliki efek mendalam pada kepadatan elektron di sekitar atom karbon yang berbeda. Mahasiswa substitue tertentu menyebabkan kerapatan elektron lebih besar di orto dan para positiois daripada di posisi meta, maka mereka menghasilkan produk nitrasi di mana orto dan para isomer mendominasi. Substituen lainnya menyebabkan kerapatan elektron lebih besar pada posisi meta dari pada posisi orto dan para. Isomer distribut ion yang timbul dari nitrasi benzena monosubstituted berbagai ditunjukkan pada Tabel 4-1
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1
For excellent discussione on aromatic nitration, see GILLEsPiE and MILLEr, Quart. Rev., 2, 277 (1948); INgold, “Structure and Mechanisms in Organic Chemistry,” p. 269, Cornell University Press, Ithaca, N.Y., 1953. Naftalena Series. Dalam serial naphtKalene, adalah mungkin untuk memiliki dua berbeda mononitro derivatif, yaitu, alpha dan beta senyawa., Juga dikenal di 1nitronaphthalene dan 2nitronaphthalene. Setelah nitrasi, kelompok nitro pertama memasuki hampir secara eksklusif ke alpha atau 1 posisi; kelompok nitro kedua masuk ke posisi 5 atau 8.
Anthraquinmze Series. Dalam serial antrakuinon, nitrasi dengan asam campuran yang mengandung sedikit kelebihan lebih dari satu setara dengan hasil asam nitrat dalam pembentukan tiga turunan nitro. Ini adalah alpha-1 diganti-nitroanthraquinone dan 1,5-dan 1,8dinitroanthraqu-nones. Teori Substitusi Aromatik. Perkembangan teori orientasi dalam substitusi aromatik, yang terutama disebabkan oleh R. Robinson dan CK Ingold dan rekan kerja mereka, merupakan salah satu ers chapt paling menarik dalam kimia organik. Menurut teori ini, substituen yang mempengaruhi kerapatan elektron dalam dua cara penting oleh efek induktif (saya ketika menarik elektron dan +1 ketika repels elektron) dan oleh efek mesomeric (BM-atau + M). Efek induktif dikaitkan dengan momen dipol senyawa C6H5 X. Jika X adalah di ujung negatif dari dipol, itu akan menarik elektron dari cincin dan menghasilkan efek-I, ditandai dengan panah C6H5 lurus X. Jika X adalah di ujung positif dari dipole, maka akan meningkatkan densitas elektron dalam cincin dan prod UCE efek +1. Grup whichproduce efek I dalam rangka kekuatan ng decreasi adalah-NMe3, -, NO2-COOEt,-halogen. Grup yang menghasilkan efek yang +1 -0 dan alkil. Efek +1 menyebabkan semua ion menempatkan dalam cincin agar lebih reaktif daripada di benzena tersubstitusi, posisi orto dan para yang dibuat agak lebih reaktif daripada meta. Efek I mengurangi reaktivitas dari semua posisi dalam cincin relatif terhadap benzena, efek yang lebih besar dalam orto dan posisi para, meninggalkan posisi meta menjadi lebih reaktif. Dengan demikian nitrasi toluena menghasilkan didominasi orto-dan para-nitrotoluene, sedangkan nitrasi nitrobenzena menghasilkan sebagian besar meta-dinitrobeuzene.
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Substituen yang memiliki sepasang tidak berhubungan elektron dapat meningkatkan densitas elektron dalam cincin oleh efek mesomeric, + M, yang merupakan indikasikan oleh panah melengkung. Substituen lainnya dapat mengurangi kerapatan elektron dalam cincin oleh M-efek. Efek ini diilustrasikan dalam diagram yang men yertainya .
Substituen yang menunjukkan efek + M mengaktifkan semua posisi dalam cincin benzena tersubstitusi relatif terhadap, efek yang lebih diucapkan pada posisi orto dan para daripada di posisi meta. Demikian pula, tituents subs memamerkan M-efek menonaktifkan semua posisi, meta yang sedang kurang dinonaktifkan dari orto dan para. Grup yang menunjukkan +1 dan + efek M jelas akan memfasilitasi dan menjadi substitusi orto-para mengarahkan, dan kelompok yang memiliki - I dan efek M akan membuat substitut ion lebih sulit dan 'menjadi mengarahkan meta. Ketika dua efek yang bertentangan, yakni, I dan + - M atau - I dan + M, hasil bersih akan lebih sulit diprediksi. The asetoksi, metoksi, dan kelompok acetamino semua menunjukkan I, M + efek. Efek + M jauh lebih kuat daripada efek I, dan sebagainya fenil acette, anisol, dan Acetanilide dapat segera nitrasi dan produk yang didominasi dengan orto-para nitro derivat ives. Halogen juga memproduksi-I dan M + efek, tetapi dalam kasus ini dua efek penting sebanding. Substituen A akan membuat posisi orto kurang diakses oleh incomi ng nitro kelompok sesuai dengan ukurannya. Semakin besar substituen, kurang
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Diakses akan posisi orto menjadi lebih kecil dan akan menjadi orto: para rasio produk & Bukti untuk efek thir dapat dilihat dari hasil mononitration dari alk ylbenzenes yang ditunjukkan pada Tabel 4-4 Sebagai berikut:
Gugus alkil meningkat dalam ukuran, hasil da ri orto-tersubstitusi menurun produk dan orto: rasio para menurun. Tingkat serangan pada posisi nuklir individu toluena dan t-butylben.zene (tingkat untuk satu posisi benzena yang diambil sebagai s atu kesatuan) menyajikan comparis berikut pada:
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dominan. Dengan cara ilustrasi, produk-produk dari nitrasi halida fenil ditunjukkan pada Tabel 4-5 dikutip. Efek penurunan
The orto: para ratio juga dipengaruhi oleh media nitrasi dengan cara yang tidak dapat dijelaskan oleh teori Robinson-Ingold. Distribusi isomer yang hasil dari nitrasi anilin dan anilides di media penitrasi beberapa ditunjukkan pada Tabel 4-6. Nitrasi Acetanilide dengan nitroacetanilides asam hasil campuran di mana orto: para ratio kurang dari 0, l Ketika media nitrasi adalah asam nitrat, rasio ini adalah 0,7, ketika nitrat asetil dalam anhidrida asetat digunakan, produk ini hampir seluruhnya o -nitroacetanilide. Tidak ada penjelasan yang memuaskan telah diberikan untuk hasil ini. Hasil 40-50 persen dari m-nitro-. aniline that results from the nitration of aniline in mixed acid or in nitric acid can be explained in the following manner. In the strong acids, nitric and sulfuric acid, aniline is largely ionized.
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Ion anilinium Ulasan Sangat dinonaktifkan karena bahasa Dari Efek NH3-penganti. Nitrasi Yang Akan menghasilkan isomer meta. Amina Bebas, Akan Ulasan Sangat Aktif karena Efek + M bahasa Dari Kelompok-NH2, Dan Akan menghasilkan isomer para. tn asam Yang relatif yang Lemah, asam asetat, konsentrasi ion anilinium Akan JAUH
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Pengaruh jumlah air yang hadir pada laju reaksi ditunjukkan pada Gambar. 4-2. Laju reaksi meningkat tajam dengan meningkatnya konsentrasi asam & tlfuric dan mencapai maksimum pada sekitar 90 persen H2S04 dan kemudian jatuh pada konsentrasi asam yang lebih tinggi. Ini pertama kali diusulkan oleh Westheimer dan 'Kharasch bahwa kenaikan ken aikan tingkat dengan kekuatan asam meningkat ketika asam dalam waktu kurang dari 90 persen disebabkan oleh peningkatan konsentrasi ion nitryl. Hal ini menunjukkan bahwa konstanta kesetimbangan untuk ionisasi tris pnitrophenylcarbinol meningkat dalam cara yang sama seperti tingkat konstan, seperti yang ditunjukkan pada Gambar. 4-2.
diyakini bahwa kedua konstanta ionisasi akan menunjukkan endence dcp serupa pada kekuatan asam. Kesimpulan ini tampaknya dibenarkan dalam pandangan bukti yang kuat untuk ion nitryl diberikan dalam paragraf pada agen penitrasi.
Fio. 4-2. The effect of water on the rate of nitration and on the ionization of
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berfungsi untuk menghilangkan proton dari antara bermuatan positif terbentuk pada langkah 2. Teori ini ditemukan dipertahankan dari percobaan dengan substrat aromatik isotopically berlabel. Jika penghapusan hidrogen adalah langkah lambat, maka nitrasi senyawa aromatik di mana drogen digantikan oleh deuterium atau tritium harus dilanjutkan lebih lambat. Telah ditemukan bahwa eksperimen tritium-mengandung senyawa yang nitrasi pada tingkat yang sama sebagai zat yang mengandung hidrogen. Sebuah penjelasan yang masuk akal untuk penurunan tingkat keasaman yang lebih tinggi pada telah diberikan oleh Gillespie dan Mullen.1 interaksi An terjadi antara substrat organik dan asam sulfat yang menurunkan ity sarang elektron dalam cincin dan karenanya mengurangi reaktivitas. Interaksi ini mungkin formasi hydrogenbond. Ikatan hidrogen antara nitro benzena dan asam suffuric dapat digambarkan.
Kekuatan ikatan hidrogen meningkat dengan keasaman donor hidrogen, yang dalam hal ini adalah asam sulfat. Penurunan kadar air asam sehingga akan diharapkan, untuk meningkatkan interaksi antara asam dan substrat organik, yang mengakibatkan penarikan besar elektron dari cincin. Nitrasi dalam Pelarut Organik. Dalam nitromethane pelarut organik atau asam asetat, asam nitrat dengan lebih besar, kinetika proses nitrasi tergantung pada senyawa aromatik yang nitrasi. Senyawa seperti nitrobenzena atau etil benzoat yang memiliki kelompok kuat menonaktifkan yang nitrasi pada tingkat yang sebanding dengan konsentrasi substrat, yaitu, reaksi urutan pertama. Senyawa yang lebih reaktif daripada benzena, seperti toluena, xilena, dan pchloranisole, bereaksi pada tingkat yang independen dari konsentrasi substrat, yaitu, reaksi orde nol. Laju reaksi dengan semua substrat yang menunjukkan orde nol kinetika adalah sama. Penafsiran yang paling masuk akal dari hasil h asil ini adalah sebagai berikut. Pembentukan ion nitryl
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yang merupakan laju pembentukan ion nitryl. Setiap senyawa dalam kelas ini bereaksi pada tingkat karakteristik sendiri. Dalam nitrasi conpounds reaktivitas menengah, kedua langkah terjadi pada tingkat yang sebanding.
Ion nitryl setelah dibentuk oleh reaksi atas bereaksi dengan air dengan cepat:
Pengaruh Asam Nitrous pada Nitrations. Asam nitrit atau nitrogen dioksida dalam kasus tertentu exerts efek menghambat dan dalam kasus lain memberikan suatu efek katalitik pada nitrations aromatik. Efek menghambat diamati 1Burton and Halevi, J. Halevi, J. Chem. Soc., 1952, 4917.
yang menurunkan konsentrasi ion nitryl (lihat persamaan, hal. 61) dan dengan demikian mengurangi laju reaksi. Efek katalitik diamati dalam nitrasi substrat reaktif seperti anisol atau
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Westheimer dan rekan kerja bahwa reaksi ini terjadi dalam langkah-langkah berikut:
Benzena ini awalnya dikonversi ke nitrat phenyluiercuric yang bereaksi dengan nitrogen
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nitrobutane,
1-nitroisobutane,
1-nitro-3-methylbutane,
2-nitro-3-methylbutane.
Nitrasi menghasilkan mononitroparaffins saja dan tidak ada sejumlah besar senyawa polynitro. Meskipun pembelahan kerangka karbon terjadi, seperti yang ditunjukkan di atas, tidak ada penataan kerangka karbon telah ditemukan terjadi.
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meningkatkan
hasil
nitrometana
dan
nitroethane
dan
menurunkan hasil nitrobutane. Peningkatan permukaan: rasio volume dalam reaktor untuk 300 membuat konversi sedikit lebih tinggi kemungkinan asam nitrat dan menghasilkan perbaikan yang mencolok dalam hasil berdasarkan kontra butana Umed. Ketika O,: HNO: = 1. Hasil didasarkan pada butana dikonsumsi meningkat dari 32 menjadi 45 persen. Penggunaan uap
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Brom memiliki efek menguntungkan pada kedua hasil dan konversi untuk nitroparaffins menggunakan abid nitrat. Pada 423 ° C, waktu kontak 1,5 lihat, dan rasio berikut reaktan, propana: 02 = 8,2, propana, asam nitrat = 9,9, air: asam nitrat = 15, dan Br2: HNO3 = 0,015, konversi persen per asam nitrat adalah 47,7 dan hasil berdasarkan propana adalah 55,5 persen. Hasil panen dari produk lainnya adalah sebagai berikut: CO2 = 0, CO = 3,6, 9,7 C3H6, C2H4 = 4.1, aldehid dan keton = 27 persen. Efek klorin adalah o serupa yang brom. Hidrokarbon bercabang undrgo fisi kurang selama nitrasi daripada kurang bercabang mereka isomer. Sejalan dengan itu, hidrogen substitut ion lebih disukai bila struktur yang sangat bercabang yang nitrasi. Seperti dapat dilihat dari data masuk Tabel 4-8, di mana perbandingan terbuat dari nitrasi butana isomerik dan pentana, rasio molar dari produk yang dihasilkan dari reaksi fisi dengan yang dihasilkan dari substitusi hidrogen menurun sebagai kerangka karbon menjadi lebih tinggi bercabang
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Langkah-langkah berikut mungkin terlibat dalam nitrasi parafin:
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dan asam adipat bersama dengan jumlah yang lebih kecil dari asam glutarat dan asam suksinat. Nitrasi dipercepat dengan penambahan nitrogen dioksida. Proses ini dapat dioperasikan secara terus-menerus dalam fase cair dengan 45-75 persen asam nitrat pada temperatur 100 - 200 ° C dan tekanan dari 2-10 atm. Ini proceseis kepentingan tertentu dalam produk oksidasi dari sikloalkana biasanya asam arboxylic simetris DIC, yang penting industri. Nitrasi dari 2-nitropropane dengan asam nitrat untuk memberikan 2,2-dinitropropane telah dilakukan pilot-plant qnantities Corporation Solvts Komersial. Reaksi dapat dilakukan dalam stainless steel apparatus F. Termodinamika Nitrasi
Reaksi nitrasi adalah reaksi yang sangat eksotermik karena melepaskan panas. Permasalahan panas dititikberatkan karena panas cairan asam penitrasi yang akibat esensial
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Di sini Q, panas reaksi, merupakan jumlah total panas yang hilang oleh sistem yang bereaksi dari d ari awal a wal reaksi sampai produk dan kembali ke suhu dan tekanan awal dari da ri sistem. 2. Sifat thermal nitrasi asam. Memanaskan larutan. Untuk menentukan panas yang berubah selama proses nitrasi hidrokarbon oleh asam campuran, tidak hanya perlu mempertimbangkan panas nitrasi tetapi juga berbagai memanaskan larutan. Ini dapat diperoleh dari tabel entalpi yang dikembangkan oleh McKinley dan Brown. Untuk masing-masing dari tiga komponen, entalpi diambil sebagai nol pada keadaan standar, o yang terdiri dari komponen cairan murni pada suhu 32 F dan tekanan 1 atm. Diplot terhadap absis yang sama tetapi melawan koordinat yang berbeda adalah data panas
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Proses yang kontinyu, secara umum, akan ditemukan memiliki beberapa keuntungan atas proses batch: 1. Menurunkan biaya modal. Untuk tingkat produksi tertentu, peralatan yang dibutuhkan untuk proses kontinyu lebih kecil daripada untuk proses batch. 2. Keselamatan. Karena peralatan proses kontinyu ukurannya yang relatif relatif kecil 3. Buruh penggunaan. Dalam bidang nitrasi, proses yang kontinyu adalah pengguna tenaga kerja lebih efisien daripada proses batch. 2. Batch Nitration . Nitrasi biasanya dilakukan dalam wadah besi atau baja tertutup. Praktik modern yang digunakan adalah baja karbon yang ringan. Ketika penitrasi dicampur dengan asam (nitrat-sulfat), (nitrat-sulfat), masa pakai nitrators tersebut tersebut baik, dan setiap kegagalan masanyaa yang singkat biasanya dapat ditelusuri melalui air yang berlebihan atau nitrat kandungan asam rendah yang terdapat dalam limbah asam. Secara umum, nitrator terdiri dari sebuah kapal silinder tegak yang mengandung beberapa jenis permukaan pendinginan, alat agitasi, inlet umpan atau inlet, dan lini
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3. Nitrasi kontinyu . Yang terkenal awal aplikasi prosedur kontinyu untuk nitrasi dari alkohol polihidrat seperti gliserin dan hidrokarbon seperti benzena dibuat di Eropa. Metode yang digunakan untuk produksi kontinyu yaitu produk yang likuid, dan karenanya dapat dipisahkan dari cairan bercampur lain seperti menghabiskan asam penitrasi dengan decanting prosedur, serta nitrations yang cepat dan tidak oleh karena
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1. Pengolahan asam . Materi yang memasuki asam pengolahan 65 persen oleum dari kontak-proses tanaman sulfat, 50-60 persen HNO3 dari pabrik ammonia-oksidasi, dan menghabiskan asam dari operasi nitrasi. Pengolahan menghasilkan asam campuran nitrogliserin, terkonsentrasi HNO3, dan 93 persen H2SO4. Biasanya 93 persen H2SO4 dihasilkan harus dibuang oleh penjualan ke produsen pupuk, untuk asam pengguna teknis
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2. Preparation of m-Dinitrobenzene
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Trusted by over 1 million members
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Trusted by over 1 million members
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Trusted by over 1 million members
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Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.
Trusted by over 1 million members
Try Scribd FREE for 30 days to access over 125 million titles without ads or interruptions! Start Free Trial Cancel Anytime.