22
M. B. Shiflett et al.
process,
48 in operation since 2002, is generally recognized as the first example of a
commercially successful process using ionic liquids (although it was probably not the
first, as another chemical company
49 claimed priority with an isomerization process
using ionic liquids [80, 83]) [106, 107]. This reaction served as a prime example for
an alternative that could outperform an established method causing the old process
to be abandoned. In 2004, the new process won the Innovation for Growth Award of
the magazine European Chemical News [83] as well as the Innovation Award of the
company’s Board of Executive Directors [105]. In fact, many scientific or popular
tracts on the industrial uses of ionic liquids describe this biphasic acid scavenging
process. In this regard, we refer to three standard monographs: (1) Ionic Liquids in
Synthesis by Wasserscheid and Welton [108], (2) the volume on ionic liquids in the
Handbook of Green Chemistry edited by Anastas [109], and (3) the book Multiphase
Homogeneous Catalysis by Cornils et al. [110]. Scheme 2 illustrates the reaction principle. Alkoxyphenylphosphines are precursors in the production of the company’s
substances that are used as photoinitiators
50 to cure coatings and printing inks by
exposure to UV light. A process had been established that removed the hydrochloric
acid by a tertiary amine resulting in the generation of an ammonium salt that precipitated as a sticky slurry. The idea was to employ 1-methylimidazole (MIA), another
existing bulk product, instead of the tertiary amine that luckily generated a separate
liquid phase, a genuine ionic liquid, at operating conditions.
The lower ionic liquid phase could easily be removed and later retransformed
into 1-methylimidazole. The reaction was significantly improved and enabled the
company to replace the batch vessel with a jet reactor. The company also explored
the possibilities of applying this principle to other similar reactions. Presently, the
company supplies 18 ILs [111] and 8 have a REACH registration.
51
Scheme 2 Acid quench reaction of dichlorophenylphosphine (DCPP) to diethoxyphenylphosphine
(DEPP) with a base that forms an ionic liquid, 1-methylimidazolium chloride
48 BASIL ™ , BASF SE.
49 Eastman Chemical Company.
50 LUCIRINES ® , BASF SE.
51 Basionics ™ BC01 [C 2 C 1 im][Ace], HP01 [C 2 C 1 im][NTf 2 ], LQ01 [C 2 C 1 im][C 2 SO 4 ], ST70
[C 4 C 1 im][Cl], ST80 [C 2 C 1 im][Cl], VS03 [C 2 C 1 im][N(CN) 2 ], FS01 [N 1 2OH 2OH 2OH ][C 1 SO 4 ],
and the formulation [C 2 C 1 im][C 1 CO 3 ] in methanol, respectively.
M. B. Shiflett et al.
process,
48 in operation since 2002, is generally recognized as the first example of a
commercially successful process using ionic liquids (although it was probably not the
first, as another chemical company
49 claimed priority with an isomerization process
using ionic liquids [80, 83]) [106, 107]. This reaction served as a prime example for
an alternative that could outperform an established method causing the old process
to be abandoned. In 2004, the new process won the Innovation for Growth Award of
the magazine European Chemical News [83] as well as the Innovation Award of the
company’s Board of Executive Directors [105]. In fact, many scientific or popular
tracts on the industrial uses of ionic liquids describe this biphasic acid scavenging
process. In this regard, we refer to three standard monographs: (1) Ionic Liquids in
Synthesis by Wasserscheid and Welton [108], (2) the volume on ionic liquids in the
Handbook of Green Chemistry edited by Anastas [109], and (3) the book Multiphase
Homogeneous Catalysis by Cornils et al. [110]. Scheme 2 illustrates the reaction principle. Alkoxyphenylphosphines are precursors in the production of the company’s
substances that are used as photoinitiators
50 to cure coatings and printing inks by
exposure to UV light. A process had been established that removed the hydrochloric
acid by a tertiary amine resulting in the generation of an ammonium salt that precipitated as a sticky slurry. The idea was to employ 1-methylimidazole (MIA), another
existing bulk product, instead of the tertiary amine that luckily generated a separate
liquid phase, a genuine ionic liquid, at operating conditions.
The lower ionic liquid phase could easily be removed and later retransformed
into 1-methylimidazole. The reaction was significantly improved and enabled the
company to replace the batch vessel with a jet reactor. The company also explored
the possibilities of applying this principle to other similar reactions. Presently, the
company supplies 18 ILs [111] and 8 have a REACH registration.
51
Scheme 2 Acid quench reaction of dichlorophenylphosphine (DCPP) to diethoxyphenylphosphine
(DEPP) with a base that forms an ionic liquid, 1-methylimidazolium chloride
48 BASIL ™ , BASF SE.
49 Eastman Chemical Company.
50 LUCIRINES ® , BASF SE.
51 Basionics ™ BC01 [C 2 C 1 im][Ace], HP01 [C 2 C 1 im][NTf 2 ], LQ01 [C 2 C 1 im][C 2 SO 4 ], ST70
[C 4 C 1 im][Cl], ST80 [C 2 C 1 im][Cl], VS03 [C 2 C 1 im][N(CN) 2 ], FS01 [N 1 2OH 2OH 2OH ][C 1 SO 4 ],
and the formulation [C 2 C 1 im][C 1 CO 3 ] in methanol, respectively.