Proces Wacker

Procesul Wacker (sau procesul Hoechst-Wacker ^[1] ) a fost inițial menționat exclusiv la procesul de producere a acetaldehidei de la oxidarea etilenei în prezența unui catalizator de paladiu . ^{[2] [3]} Ulterior cu același nume (prin extensie) a fost indicată o clasă de procese pentru producerea de aldehide și cetone începând de la olefine , denumită adesea oxidare Wacker, care au loc prin cataliză omogenă cu un catalizator pe bază de paladiu.

La fel ca procesul de hidroformilare , procesul Wacker duce la formarea aldehidelor.

Producția de acetaldehidă

Mecanism de reacție

Reacția de producere a acetaldehidei este următoarea:

${\displaystyle \mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">P.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">d</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">4</span></span>}}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">SAU</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">\to </span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">3</span></span>}}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">SAU</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">P.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">d</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}}${\ displaystyle \ mathrm {PdCl_ {2} + C_ {2} H_ {4} + H_ {2} O \ rightarrow CH_ {3} CHO + Pd + 2HCl}}

această reacție este urmată de reacțiile de regenerare ale catalizatorului :

${\displaystyle \mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">P.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">d</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">tu</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">\to </span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">P.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">d</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">tu</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}}${\ displaystyle \ mathrm {Pd + 2CuCl_ {2} \ rightarrow PdCl_ {2} + 2CuCl}}

${\displaystyle \mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">tu</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">1</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">/</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">SAU</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">\to </span></span>\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">tu</span></span>}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">C.</span></span>}{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">L</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">+</span></span>{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">H.</span></span>}}_{\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">2</span></span>}}\mathrm{<span\; class="mwe-math-element"><span\; class="mwe-math-mathml-inline\; mwe-math-mathml-a11y"\; style="display:\; none;">SAU</span></span>}}${\ displaystyle \ mathrm {2CuCl + 1 / 2O_ {2} + 2HCl \ rightarrow 2CuCl_ {2} + H_ {2} O}}

În procesul general, se consumă numai etilenă și oxigen , în timp ce concentrația de catalizator în mediul de reacție rămâne constantă. Clorura de cupru și acidul clorhidric au, de asemenea, o concentrație constantă, de fapt scopul lor este de a crea un mediu oxidant pentru a favoriza regenerarea catalizatorului.

Mecanismul de reacție al procesului Wacker ^[4]

Producția de acetonă

Procesul Wacher pentru producția industrială de acetonă a fost adoptat în 1964; sinteza implică oxidarea directă a propilenei în acetonă prin intermediul unui sistem de _PdCl2 catalizatori. Sinteza continuă cu o bună selectivitate (aproximativ 90%) dacă reacția se desfășoară în faza lichidă și sub presiune; subprodusul reacției poate fi aldehida propionică. Ciclul catalitic cuprinde o serie de reacții redox în care Pd ²⁺ este redus la Pd ⁰ de CuCl care se oxidează la CuCl ₂ . Primele uzine Wacker au fost instalate în Japonia în 1964.

Producerea de anhidridă acetică

Această secțiune despre chimie este încă goală . Ajută-ne să-l scriem!

Notă

Bibliografie

• ( EN ) Klaus Weissermel, Hans-Jürgen Arpe, Charlet R. Lindley, "Industrial organic chimie" , ed. 4, Wiley-VCH, 2003, pp. 166–169, 183-184, 279. ISBN 3-527-30578-5

Alte proiecte

• Wikimedia Commons conține imagini sau alte fișiere despre procesul Wacker

linkuri externe

• ( EN ) Wacker Trial , în Encyclopedia Britannica , Encyclopædia Britannica, Inc.

Portalul chimiei

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