3-Bromopyridine-Heterogenized Phosphotungstic Acid for Efficient Trimerization of Biomass-Derived 5-Hydroxymethylfurfural with 2-Methylfuran to C<sub>21</sub> Fuel Precursor

<div><sup>1</sup>H and <sup>13</sup>C NMR spectra of intermediate 1. Intermediate 1: <sup>1</sup>H NMR (500 MHz, CDCl<sub>3</sub>) <svg height="9.49473pt" id="M18" style="vertical-align:-0.2063999pt" version="1.1" viewbox="-0.0498162 -9.28833 43.5344 9.49473" width="43.5344pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M494 514C482 587 419 712 303 712C238 712 174 667 174 603C174 561 205 514 249 449C219 438 187 422 162 407C93 366 23 283 23 177C23 69 87 -12 190 -12C244 -12 288 5 328 33C406 87 444 170 444 249C444 329 404 391 331 475C265 550 222 605 222 627C222 647 238 657 267 657C355 657 421 585 484 499L494 514ZM359 234C359 143 319 30 219 30C172 30 114 75 114 178C114 275 163 343 195 378C212 397 241 415 269 425C305 382 359 313 359 234Z"></path></g><g transform="matrix(.013,0,0,-0.013,10.354,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,21.617,0)"><path d="M137 343C167 482 260 545 321 574C357 591 397 603 429 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519 318 435C318 349 255 267 193 193C144 135 87 78 32 23V0H405C417 45 427 89 440 131L412 140Z"></path></g></svg> (<span class="nowrap"><svg height="9.49473pt" id="M19" style="vertical-align:-0.2063999pt" version="1.1" viewbox="-0.0498162 -9.28833 7.34169 9.49473" width="7.34169pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M530 686C535 705 530 712 521 712C504 712 448 684 359 674L358 648H393C437 648 439 646 429 593L400 435C372 447 345 448 332 448C286 448 194 414 144 373C68 311 23 203 23 111C23 26 57 -12 91 -12C120 -12 147 3 188 29C227 54 290 102 341 170H343L322 71C308 6 320 -12 341 -12C373 -12 442 27 501 96L485 120C455 91 422 67 408 67C401 67 401 76 404 91C440 294 479 473 530 686ZM387 375L355 241C326 187 200 53 142 53C126 53 109 73 109 130C109 217 154 337 218 381C240 396 265 404 297 404S372 390 387 375Z"></path></g></svg>,</span> <svg height="10.5647pt" id="M20" style="vertical-align:-1.928801pt" 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23 111C23 26 57 -12 91 -12C120 -12 147 3 188 29C227 54 290 102 341 170H343L322 71C308 6 320 -12 341 -12C373 -12 442 27 501 96L485 120C455 91 422 67 408 67C401 67 401 76 404 91C440 294 479 473 530 686ZM387 375L355 241C326 187 200 53 142 53C126 53 109 73 109 130C109 217 154 337 218 381C240 396 265 404 297 404S372 390 387 375Z"></path></g></svg>,</span> <svg height="10.5647pt" id="M22" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 36.4229 10.5647" width="36.4229pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g 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602Z"></path></g></svg> Hz, 1H), 5.89 (<span class="nowrap"><svg height="9.49473pt" id="M27" style="vertical-align:-0.2063999pt" version="1.1" viewbox="-0.0498162 -9.28833 7.34169 9.49473" width="7.34169pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M530 686C535 705 530 712 521 712C504 712 448 684 359 674L358 648H393C437 648 439 646 429 593L400 435C372 447 345 448 332 448C286 448 194 414 144 373C68 311 23 203 23 111C23 26 57 -12 91 -12C120 -12 147 3 188 29C227 54 290 102 341 170H343L322 71C308 6 320 -12 341 -12C373 -12 442 27 501 96L485 120C455 91 422 67 408 67C401 67 401 76 404 91C440 294 479 473 530 686ZM387 375L355 241C326 187 200 53 142 53C126 53 109 73 109 130C109 217 154 337 218 381C240 396 265 404 297 404S372 390 387 375Z"></path></g></svg>,</span> <svg height="10.5647pt" id="M28" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 36.4229 10.5647" width="36.4229pt" 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312C354 172 330 22 240 22C152 22 124 173 124 313S148 602 238 602Z"></path></g></svg> Hz, 1H), 5.40 (s, 1H), 4.55 (s, 2H), 2.25 (s, 6H). <sup>13</sup>C NMR (126 MHz, CDCl<sub>3</sub>) <span class="nowrap"><svg height="9.49473pt" id="M29" style="vertical-align:-0.2063999pt" version="1.1" viewbox="-0.0498162 -9.28833 56.0612 9.49473" width="56.0612pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M494 514C482 587 419 712 303 712C238 712 174 667 174 603C174 561 205 514 249 449C219 438 187 422 162 407C93 366 23 283 23 177C23 69 87 -12 190 -12C244 -12 288 5 328 33C406 87 444 170 444 249C444 329 404 391 331 475C265 550 222 605 222 627C222 647 238 657 267 657C355 657 421 585 484 499L494 514ZM359 234C359 143 319 30 219 30C172 30 114 75 114 178C114 275 163 343 195 378C212 397 241 415 269 425C305 382 359 313 359 234Z"></path></g><g transform="matrix(.013,0,0,-0.013,10.354,0)"><path d="M535 323V373H52V323H535ZM535 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35 62 22C75 10 116 -12 162 -12C234 -12 424 62 424 224C424 297 373 359 285 376V378Z"></path></g><g transform="matrix(.013,0,0,-0.013,40.337,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,43.301,0)"><path d="M456 178V225H360V632H320C217 496 115 347 20 206V178H280V106C280 40 276 34 189 27V0H445V27C364 34 360 39 360 106V178H456ZM280 225H82C149 335 214 431 278 520H280V225Z"></path></g><g transform="matrix(.013,0,0,-0.013,49.542,0)"><path d="M412 140C382 77 369 73 315 73H129L270 222C362 320 402 379 402 466C402 571 322 635 234 635C177 635 130 609 99 576L42 495L64 475C90 514 133 568 201 568C274 568 318 519 318 435C318 349 255 267 193 193C144 135 87 78 32 23V0H405C417 45 427 89 440 131L412 140Z"></path></g></svg>,</span> 152.85, 151.66, 150.24, 108.74, 108.05, 106.32, 57.68, 39.24, 13.67.</div>

Advances in Polymer Technology

fig10

Figure 10

Figure 10: 3-Bromopyridine-Heterogenized Phosphotungstic Acid for Efficient Trimerization of Biomass-Derived 5-Hydroxymethylfurfural with 2-Methylfuran to C<sub>21</sub> Fuel Precursor 

Figure 10 | 3-Bromopyridine-Heterogenized Phosphotungstic Acid for Efficient Trimerization of Biomass-Derived 5-Hydroxymethylfurfural with 2-Methylfuran to C21 Fuel Precursor 