Boots-Hoechst-Celanese

The Boots Hoechst Celanese (BHC) ibuprofen process involves palladium-catalyzed carbonylation of a benzylic alcohol (IBPE). More recently, we performed this reaction in an aqueous biphasic system using Pd/tppts as the catalyst (Figure 9.6 tppts = triphenylphosphinetrisulfonate). This process has the advantage of easy removal of the catalyst, resulting in less contamination of the product. 

In the BHC (Boots-Hoechst Celanese) process about 3500 tons of ibuprofen per annum are produced by Pd/PPh3-catalysed carbonylation of IBPE (Figure 9) in the presence of HC1, in organic media.446 447,459 461 However, a shortcoming of this process is the cumbersome separation of the Pd/PPh3 catalyst from the... 

Boots-Hoechst-Celanese process More recently, a shorter three-step catalytic route has been developed and is illustrated in the following scheme. Here, a Pd catalyzed carbonylation reaction is employed in the final step to introduce the carboxyl group. 

In 1992 BHC (Boots Hoechst-Celanese) Company commercialized a new synthetic process to manufacture ibuprofen in BHC s 3500 metric-ton-per-year facility in Bishop/TX, USA, which was cited as an industry model of environmental excellence in chemical processing technology. For its innovation, BHC was the recipient of the 1997 Alternative Synthetic Pathways Award of the Presidential Green Chemistry Challenge. 

Because ibuprofen has been a successful drug on the market for almost 30 years with no patent protection since 1985, there is a widespread competition for commercial production of this product throughout the world. As a result, several practical and economical industrial processes for the manufacture of racemic ibuprofen (14) have been developed and are in operation on commercial scales.38 Most of these processes start with isobutylbenzene (15) and go through an isobutylstyrene3 4 or an acetophenone intermediate.42 The most efficient route is believed to be the Boots-Hoechst-Celanese process, which involves 3 steps from isobutylbenzene, all catalytic, and is 100% atom-efficient (Scheme 6.1).43 44... 

The profens are non-steroidal anti-inflammatory agents based on arylpropionic acids the best known is ibuprofen. The BHC company (Boots-Hoechst-Celanese) developed a commercial route to ibuprofen which involves a... 

The Boots-Hoechst-Celanese Process for Ibuprofen Synthesis... 

In 1997, the developers of the Boots-Hoechst-Celanese process were awarded the Presidential Green Chemistry Award, sponsored by the U.S. Environmental Protection Agency. 

Catalytic Cycle for the Carbonylation Step of the Boots-Hoechst-Celanese Synthesis of Ibuprofen... 

A striking example of this is the manufacture of ibuprofen using the Boots Hoechst-Celanese process based on homogeneous catalytic carbonylation of p-isobutylphenyl-ethanol as a key step. 

The optimised synthesis of ibuprofen by Boots-Hoechst-Celanese however comprises only four reaction steps p-lsobutylacetophenone is prepared by a... 

The Boots patent on ibuprofen expired in the 1980s, and other manufacturers became able to manufacture and sell ibuprofen. In 1991, the Boots and Hoechst Celanese... 

In the 1990s the Hoechst Celanese Corporation (together with the Boots company they formed the BHC process to prepare and market ibuprofen, 1.16) developed a new three-stage process (Scheme 1.9), with an atom economy of 77.4%. 

Ibuprofen can be manufactured via two routes, the classical Boots process (the inventor of the drug) and a new route developed by Hoechst Celanese. Both routes share the intermediate, p-isobutylacetophenone. Compare both processes ... 

As the product came off patent, there was enormous pressure from generic competition and process economics became fundamental for the original patent holders, Boots, to maintain market share. Boots, in association with Hoechst Celanese in USA developed a process using hydrogen fluoride in place of aluminium trichloride to catalyse the acetylation step [17]. Liquid hydrogen fluoride requires sophisticated technology and relatively expensive plant for safe handling. It is also important to remove... 

The BHC Company is a joint venture of the Hoechst Celanese Corporation and the Boots Company. BASF purchased the Boots Company and Celanese sold its interest in the BHC Company to BASF. Celanese operates the new ibuprofen manufacturing facility in Bishop, Texas, for BASF. Ibuprofen manufactured via the BHC process is marketed under the brand names Advil and Motrin. The industrial-scale facility created in Bishop, Texas, in 1992 is the world s largest ibuprofen manufacturing plant, is operated by the Celanese Corporation for BASF, and currently produces approximately 20-25 % (more than 7 million pounds) of the world s yearly supply of ibuprofen. 

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