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 MMBM. MMBM: <sup>1</sup>H NMR (500 MHz, CDCl<sub>3</sub>) <svg height="9.49473pt" id="M30" 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 609L423 641C382 634 335 622 295 608C189 570 37 457 37 238C37 84 125 -12 242 -12C362 -12 447 89 447 209C447 311 374 393 267 393C247 393 226 386 204 376L137 343ZM227 337C318 337 361 256 361 173C361 105 336 22 258 22C176 22 126 120 126 240C126 266 127 291 132 310C155 323 189 337 227 337Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.857,0)"><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,-0.013,30.821,0)"><path d="M241 635C89 635 35 457 35 312C35 153 89 -12 240 -12C390 -12 443 166 443 312C443 466 390 635 241 635ZM238 602C329 602 354 454 354 312C354 172 330 22 240 22C152 22 124 173 124 313S148 602 238 602Z"></path></g><g transform="matrix(.013,0,0,-0.013,37.061,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g></svg> (<span class="nowrap"><svg height="9.49473pt" id="M31" 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="M32" 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 transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 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,-0.013,27.014,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 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265 404 297 404S372 390 387 375Z"></path></g></svg>,</span> <svg height="10.5647pt" id="M34" 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 transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 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,-0.013,27.014,0)"><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,-0.013,29.978,0)"><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> Hz, 1H), 5.97 (<span class="nowrap"><svg height="9.49473pt" id="M35" 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="M36" 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 transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 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,-0.013,27.014,0)"><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,-0.013,29.978,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g></svg> Hz, 2H), 5.93 (<span class="nowrap"><svg height="9.49473pt" id="M37" 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="M38" 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 transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 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,-0.013,27.014,0)"><path d="M113 -12C146 -12 170 11 170 46C170 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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="M40" 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 transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 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,-0.013,27.014,0)"><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,-0.013,29.978,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g></svg> Hz, 2H), 5.87 (<span class="nowrap"><svg height="9.49473pt" id="M41" 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="M42" 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 transform="matrix(.013,0,0,-0.013,20.774,0)"><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><g transform="matrix(.013,0,0,-0.013,27.014,0)"><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,-0.013,29.978,0)"><path d="M244 635C114 635 38 519 38 422C38 317 111 240 217 240C236 240 255 244 277 256L345 292C311 140 203 39 59 15L64 -15C89 -15 150 -5 204 17C339 72 440 202 440 386C440 521 368 635 244 635ZM228 602C326 602 352 479 352 390C352 370 351 347 348 324C327 308 293 296 258 296C174 296 124 369 124 458C124 517 152 602 228 602Z"></path></g></svg> Hz, 1H), 5.39 (s, 1H), 3.92 (s, 2H), 2.26 (s, 9H). <sup>13</sup>C NMR (126 MHz, CDCl<sub>3</sub>) <span class="nowrap"><svg height="9.49473pt" id="M43" 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 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,21.617,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 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89C88 97 80 96 71 90C59 80 50 67 49 57C48 45 52 36 66 23C80 9 123 -12 169 -12C221 -11 288 15 342 59C403 109 431 165 431 225C431 308 366 395 238 395C212 395 165 379 127 364L153 550Z"></path></g><g transform="matrix(.013,0,0,-0.013,49.541,0)"><path d="M241 635C89 635 35 457 35 312C35 153 89 -12 240 -12C390 -12 443 166 443 312C443 466 390 635 241 635ZM238 602C329 602 354 454 354 312C354 172 330 22 240 22C152 22 124 173 124 313S148 602 238 602Z"></path></g></svg>,</span> 151.45, 151.28, 151.00, 150.63, 149.79, 107.97, 107.94, 107.13, 106.29, 106.20, 39.23, 27.66, 13.67, 13.57.</div>

Advances in Polymer Technology

fig11

Figure 11

Figure 11: 3-Bromopyridine-Heterogenized Phosphotungstic Acid for Efficient Trimerization of Biomass-Derived 5-Hydroxymethylfurfural with 2-Methylfuran to C<sub>21</sub> Fuel Precursor 

Figure 11 | 3-Bromopyridine-Heterogenized Phosphotungstic Acid for Efficient Trimerization of Biomass-Derived 5-Hydroxymethylfurfural with 2-Methylfuran to C21 Fuel Precursor 