FENOL

Proceso: Lummus Application: Improved technology to produce highest quality phenol and acetone from cumene. Refined alpha methyl styrene (AMS) production is optional. High yield is achieved at low operating and capital costs without tar cracking. Description: Fresh and recycle cumene is oxidized (1) with air to form cumene hydroperoxide (CHP) using new oxidizer treatment technology to reduce organic acid formation and improve selectivity. Overhead vapors are cooled and condensed to recover cumene. Spent air is treated to absorb and recover residual hydrocarbons. Oxidate is concentrated in a multistage cumene stripping system (2). Concentrated CHP fl ows directly to the cleavage unit where it is decomposed under precisely controlled conditions using new twostage Advanced Cleavage Technology (3a and 3b). Cleavage conditions are optimized to permit CHP decomposition without producing heavy byproducts. Cleavage effl uent is neutralized (4) before the mixture is fractionated. Neutralized cleavage effl uent is fi rst split into separate acetone/cumene/AMS/water and phenol/heavier fractions (5). Overheads from the splitter are then fractionated to remove aldehydes (6) and cumene/AMS/water (7) to produce high-purity acetone (99.75+ wt%). Splitter bottoms is fractionated under vacuum to produce a crude phenol distillate (8) and a heavy waste hydrocarbon stream. Hydrocarbon impurities are removed from the crude phenol by hydroextractive distillation (9) followed by catalytic phenol treatment (10) and vacuum distillation (11) to produce ultra-high-purity phenol (+99.99 wt%). Phenol is recovered from the acetone finishing column bottoms (12) by extraction with caustic. AMS in the raffinate is then concentrated (13), hydrogenated (14) and recovered as cumene for recycle to oxidation. Refined AMS production is optional. Yields: 100,000 tons of phenol and 61,500 tons of acetone are produced from 131,600 tons of cumene, giving a product yield of over 99%.

Commercial plants: GE Plastics, Mt. Vernon, Indiana (300,000 metric tons/yr [mtpy], revamped in 1992); Formosa Chemicals & Fibre Corporation, Taiwan (400,000 mtpy, revamped in 2001 to double the original plant capacity). Lummus has more than 50 years of phenol-plant design experience. Licensor: ABB Lummus Global/GE Plastics / Illa International.

Proceso: Kellog Application: A high-yield process to produce high-purity phenol and acetone from cumene with optional byproduct recovery of alpha methylstyrene (AMS) and acetophenone (AP). Description: Cumene is oxidized (1) with air at high efficiency (+95%) to produce cumene hydroperoxide (CHP), which is concentrated (2) and cleaved (3) under high-yield conditions (+99%) to phenol and acetone in the presence of an acid catalyst. The catalyst is removed and the cleavage mixture is fractionated to produce high-purity products (4 8), suitable for all applications. AMS is hydrogenated to cumene and recycled to oxidation or optionally recovered as a pure byproduct.

Phenol and acetone are purified. A small aqueous effluent is pretreated to allow efficient biotreatment of plant wastewater. With AMS hydrogenation, 1.31 tons of cumene will produce 1 ton of phenol and 0.615 tons of acetone. This high-yield process produces very highquality phenol and acetone products with very little heavy and lightend byproducts. With over 40 years of continuous technological development, the Kellogg Brown & Root (KBR) phenol process features low cumene and energy consumptions, coupled with unsurpassed safety and environmental systems. Commercial plants: Thirty plants worldwide have been built or are now under construction with a total phenol capacity of over 2.8 MMtpy. KBR has licensed 7 grassroots plants in 10 years with a total capacity of 1.0 MMtpy. Three new licenses were awarded in 2004 with two startups scheduled for 2005. More than 50% of the worlds phenol is produced via the KBR process. Reference: Hydrocarbon Engineering, December/January 1999. Licensor: Kellogg Brown & Root, Inc.

Proceso: Sunoco/UOP Application: The Sunoco/UOP phenol process produces high-quality phenol and acetone by liquid-phase peroxidation of cumene. Description: Key process steps: Oxidation and concentration (1): Cumene is oxidized to cumene hydroperoxide (CHP). A small amount of dimethylphenylcarbinol (DMPC) is also formed, but low-pressure and low-temperature oxidation results in very high selectivity of CHP. CHP is then concentrated and unreacted cumene is recycled back to the oxidation section. Decomposition and neutralization (2): CHP is decomposed to phenol and acetone, accompanied by dehydration of DMPC to alphamethylstyrene (AMS), catalyzed by mineral acid. This unique design achieves a very high selectivity to phenol, acetone and AMS without using recycle acetone. The high total yields from oxidation and decomposition combine to achieve 1.31 wt cumene/wt phenol without tar cracking. Decomposed catalyst is neutralized. Phenol and acetone purification (3): Phenol and acetone are separated and purifi ed. A small amount of byproduct is rejected as heavy residue. AMS hydrogenation or AMS refining (4): AMS is hydrogenated back to cumene and recycled to oxidation, or AMS is refined for sale. Cumene peroxidation is the preferred route to phenol, accounting for more than 90% of world production. The Sunoco/UOP Phenol process features low feedstock consumption (1.31 wt cumene/wt phenol) without tar cracking, avoiding the expense and impurities associated with tar cracking. High phenol and acetone product qualities are achieved through a combination of minimizing impurity formation and efficient purification techniques. Optimized design results in low investment cost along with low utility and chemicals consumption for low variable cost of production. Design options for byproduct alphamethylstyrene (AMS) allow producers to select the best alternative for their market: hydrogenate AMS back to cumene, or refine AMS for sale. No acetone recycle to the decomposition (cleavage) section, simplified neutralization, and no tar cracking make the Sunoco/UOP Phenol process easier to operate. Commercial plants: The Sunoco/UOP Phenol process is currently used in 11 plants worldwide having total phenol capacity of more than 1 million mtpy. Four

additional process units, with a total design capacity of 600,000 mtpy, are in design and construction. Licensor: Sunoco and UOP LLC.