Mechanism of the Kolbe–Schmitt reaction. Part I. Infra-red studies

Hales, J. L.; Jones, J. Idris; Lindsey, A. S.

doi:10.1039/jr9540003145

Cited by 52 publications

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“….9322 (13) .5560 (3) .3108 (27) .7 (3) K(1) .7990 (11) .4185 (5) .4889 (22) 7.47(30) C (1) .6692 (17) .9142 (4) .2202 (28) 2.79(34) C (2) .8457 (15) .8946 (4) .1533 (26) 2.79(34) C (3) .5367 (13) .8351 (6) .2185 (26) 2.79(34) C (4) .8896 (11) .7958 (5) .0846 (27) 2.79(34) C (5) .5807 (9) .7363 (5) .1498 (16) 2.79(34) C (6) .7571 (10) .7167 (4) .0829 (21) 2.79(34) H (1) .6366 (23) .9875 (5) .2712 (40) 2.79(34) H (2) .9440 (19) .9533 (6) .1546 (34) 2.79(34) H (3) .4058 (15) .8497 (9) .2682 (39) 2.79(34) H(4) 1.0206 (12) .7812 (8) .0349 (41) 2.79(34) O (1) .4541 (11) .6607 (7) .1481 (24) 2.79(34) C …”

Section: Powder X-ray Diffraction Experimentsmentioning

confidence: 99%

“…Beide Verbindungen zeigen ähnliche Packungsmuster, die aus Schichten von verzerrten RbO 8 -bzw. Many models for the reaction mechanism have been published so far [7] .The type and the amount of the reaction products are strongly influenced by the reaction conditions like temperature, pressure, time, type of the alkaline cation and solvent [8]. Die Phenylringe sind senkrecht zu diesen Schichten angeordnet und liegen alternierend oberhalb bzw.…”

Section: Introductionunclassified

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The Solid State Structures of Potassium and Rubidium Salicylate by High Resolution X-Ray Powder Diffraction

Dinnebiér

Jelonek

Sieler

et al. 2002

Z. anorg. allg. Chem.

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We report the ab initio structure solution of rubidiumsalicylate C 7 H 5 O 3 Rb and the crystal packing of potassium-salicylate C 7 H 5 O 3 K by high resolution X-ray powder diffraction. The compounds are of interest for the understanding of the mechanism of Kolbe-Schmitt type reactions. C 7 H 5 O 3 Rb (I) crystallizes in space group P2 1 /n, Zϭ 4, with unit cell parameters a ϭ 7.2110(1) Å , b ϭ 26.5258(3) Å , c ϭ 4.23110(6) Å , β ϭ 106.843(1)°, and V ϭ 774.60(2) Å 3 . C 7 H 5 O 3 K (II) crystallizes in space group P1, Z ϭ 2, with unit cell parameters a ϭ 7.3575 (2), b ϭ 13.6399(3), c ϭ 3.8622(1) Å , α ϭ 95.955(4)°, β ϭ 103.326(2)°, γ ϭ 92.994(4)°, and V ϭ 373.95(2) Å 3 . Both compounds exhibit similar crystal packing Die Kristallstruktur von Kaliumsalicylat und Rubidiumsalicylat mittels hochauflösender PulverdiffraktometrieInhaltsübersicht. Wir berichten über die ab initio Strukturlösung von Rubidiumsalicylat C 7 H 5 O 3 Rb und die Kristallpackung von Kaliumsalicylat C 7 H 5 O 3 K mittels hochauflösender Röntgenpulverdiffraktometrie. Die Strukturen der Verbindungen sind von Interesse für die Interpretation der Kolbe-Schmitt-Synthese. C 7 H 5 O 3 Rb (I) kristallisiert in der Raumgruppe P2 1 /n, Z ϭ 4, mit den Gitterparametern a ϭ 7,2110(1) Å , b ϭ 26,5258(3) Å , c ϭ 4,23110(6) Å , β ϭ 106,843(1)°und V ϭ 774,60(2) Å 3 . C 7 H 5 O 3 K (II) kristallisiert in der Raumgruppe P1, Z ϭ 2, mit den Gitterparametern a ϭ 7,3575(2) Å , b ϭ 13,6399(3) Å , c ϭ 3,8622(1) Å , α ϭ 95.955(4)°,

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Section: Powder X-ray Diffraction Experimentsmentioning

confidence: 99%

Section: Introductionunclassified

The Solid State Structures of Potassium and Rubidium Salicylate by High Resolution X-Ray Powder Diffraction

Dinnebiér

Jelonek

Sieler

et al. 2002

Z. anorg. allg. Chem.

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“…For activated, electron-rich phenols, with two or more electron-donating OH groups, the carboxylation can be carried out in a smooth variant of the Kolbe-Schmitt processing (aqueous solution, reflux at 100°C, ambient pressure, soft hydrogen carbonate as carboxylating agent), different from the autoclave processing with strong alkaline media typical of the less reactive phenols [42,43]. In this manner, 2,4-dihydroxybenzoic acid (2,4-DHBA; also known as b-resorcylic acid) is synthesized from resorcinol (Scheme 1).…”

Section: Synthesis In An Aqueous Salt Solutionmentioning

confidence: 99%

Flow Chemistry of the Kolbe‐Schmitt Synthesis from Resorcinol: Process Intensification by Alternative Solvents, New Reagents and Advanced Reactor Engineering

et al. 2009

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The Kolbe-Schmitt synthesis from resorcinol was exemplarily investigated to figure out the process intensification potential of continuous processing in the milli and micro scale, alone and combined with additional intensification means like alternative solvents, new reagents and an advanced reactor design. The oil bathheated synthesis was investigated for capillary reactors of different dimensions, using aqueous solutions of KHCO 3 and reactive ionic liquids. Already the first case led to space-time yields (STY) of 15,500 kg/(m 3 h) at 37 % yield. Synthesis with different CO 2 -donating salts showed that KHCO 3 has the highest activity and that hydrogen carbonates are better than carbonates. The replacement of KHCO 3 by reactive ionic liquids led to a substantial increase, both in yield (58 %) and STY (69,900 kg/(m 3 h)). The application of scCO 2 did not significantly increase the yield despite an even more substantial change of the reaction medium. Using an electrically heated microstructured reactor resulted in a tenfold higher productivity (0.75 t/a) compared to the capillary reactor and does much better ensure scalability of the reaction.

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“…its importance, and although the reaction is known since the middle of the last century [6], its mechanism and the crystal structures of its products are still unknown. Many models for the reaction mechanism have been published so far [7] .The type and the amount of the reaction products are strongly influenced by the reaction conditions like temperature, pressure, time, type of the alkaline cation and solvent [8]. Under typical reaction conditions (120°C, 5 atm), the carboxylation of dry sodium-phenolate leads to an almost quantitative yield of sodium-salicylate, whereas carboxylation of higher homologues leads to a strong increase of the para product with increasing size of the alkali metal [9].…”

Section: Introductionmentioning

confidence: 99%

The Solid State Structures of Potassium and Rubidium Salicylate by High Resolution X-Ray Powder Diffraction

Dinnebiér

Jelonek

Sieler

et al. 2002

Z. anorg. allg. Chem.

View full text Add to dashboard Cite

We report the ab initio structure solution of rubidium-salicylate C 7 H 5 O 3 Rb and the crystal packing of potassium-salicy-late C 7 H 5 O 3 K by high resolution X-ray powder diffraction. The compounds are of interest for the understanding of the mechanism of Kolbe-Schmitt type reactions. C 7 H 5 O 3 Rb (I) crystallizes in space group P2 1 /n, Z 4, with unit cell parameters a 7.2110(1) A ˚ , b 26.5258(3) A ˚ , c 4.23110(6) A ˚ , β 106.843(1)°, and V 774.60(2) A ˚ 3. C 7 H 5 O 3 K (II) crystallizes in space group P1 ¯ , Z 2, with unit cell parameters a 7.3575(2), b 13.6399(3), c 3.8622(1) A ˚ , α 95.955(4)°, β 103.326(2)°, γ 92.994(4)°, and V 373.95(2) A ˚ 3. Both compounds exhibit similar crystal packing

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Mechanism of the Kolbe–Schmitt reaction. Part I. Infra-red studies

Cited by 52 publications

References 0 publications

The Solid State Structures of Potassium and Rubidium Salicylate by High Resolution X-Ray Powder Diffraction

The Solid State Structures of Potassium and Rubidium Salicylate by High Resolution X-Ray Powder Diffraction

Flow Chemistry of the Kolbe‐Schmitt Synthesis from Resorcinol: Process Intensification by Alternative Solvents, New Reagents and Advanced Reactor Engineering

The Solid State Structures of Potassium and Rubidium Salicylate by High Resolution X-Ray Powder Diffraction

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