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1. (WO2019002503) PREPARATION PROCESS OF ORTHO ALKOXY BISPHENOL MONOMERS
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ORTHO ALKOXY BISPHENOL MONOMERS

CLAIMS

1. A process for preparing a compound, comprising:

a. contacting at least one (alk-l-enyl)alkoxyphenol; wherein said (alk-l-enyl)alkoxyphenol is an 3-(alk-l-enyl)alkoxyphenol, an 4-(alk-l-enyl)alkoxyphenol, an 5-(alk-l-enyl)alkoxyphenol or an 6-(alk-l-enyl)alkoxyphenol, comprising the formula (I):


(I)

wherein if R1 is hydrogen (-H) than R2 is independently methyl (-CH3) or ethyl (-CH2CH3); and R3 is independently hydrogen (-H), hydroxy (-OH), methoxy (-OCH3) or ethoxy (-OCH3); and

wherein if R2 is hydrogen (-H) than R1 is independently methyl (-CH3) or ethyl (-CH2CH3); and R3 is independently hydroxy (-OH), methoxy (-OCH3) or ethoxy (-OCH3); and

wherein Ra is independently hydrogen (-H), methyl (-CH3) or ethyl (-CH2CH3); and Rb is independently hydrogen (-H), methyl (-CH3), ethyl (-CH2CH3), hydroxymethyl (-CH2OH), methoxymethyl (-CH2OCH3), methyl carboxylate (-CH20(CO)R), carboxymethyl (-CH2(CO)OH) or an ester (-CH2(CO)OR), an amide (-CH2CON HR) or salt thereof;

b. contacting at least one alkoxyphenol; wherein said alkoxyphenol is a 2-alkoxyphenol, a 3- alkoxyphenol, a 2,3-dialkoxyphenol, or a 2,6-dialkoxyphenol comprising the formula (II):


wherein if R4 is hydrogen (-H) than R5 is independently methyl (-CH3) or ethyl (-CH2CH3); and R6 is independently hydrogen (-H), hydroxy (-OH), methoxy (-OCH3) or ethoxy (-OCH3);

wherein if R5 is hydrogen (-H) than R4 is independently methyl (-CH3) or ethyl (-CH2CH3); and R6 is independently hydroxy (-OH), methoxy (-OCH3) or ethoxy (-OCH3);

with at least one acidic catalyst; wherein said acidic catalyst comprises an acid selected of the group consisting of a soluble acid, an acidic ion-exchange resin, an acidic clay and an acidic zeolite; and

erein said compound is an ortho alkoxy bisphenol monomer of formula (III):


(Ill)

wherein 1- 6, Ra and Rb are as defined herein for formula (I) and formula (II); and

wherein the bridging carbon group, connecting the two hydroxyl-substituted aryl groups, and the hydroxyl substituent (next to the alkoxy) on each aryl group are disposed ortho, meta or para to each other on the aryl group bearing the phenolic (-ArOH) functionality.

2. The process according to claim 1, wherein the acidic catalyst is an acidic zeolite.

3. The process according to claim 1, wherein said at least one (alk-l-enyl)alkoxyphenol is selected from the group comprising 4-vinylguaiacol, 4-vinylguaethol, 3-methoxy-5-vinylcatechol and 4- vinylsyringol.

4. The process according to claim 1, wherein said at least one (alk-l-enyl)alkoxyphenol is selected from the group comprising isoeugenol, propenylguaethol, 3-methoxy-5-(prop-l-en-l-yl)catechol and 4-(prop-l-en-l-yl)syringol.

5. The process according to claim 1, wherein said at least one (alk-l-enyl)alkoxyphenol is selected from the group comprising coniferyl alcohol, 5-hydroxyconiferyl alcohol and sinapyl alcohol; and an ether or ester thereof.

6. The process according to claim 1, wherein said at least one (alk-l-enyl)alkoxyphenol is selected from the group comprising isoferulic acid, ferulic acid, 5-hydroxyferulic acid and sinapic acid; and an ester, an amide, or salt thereof.

7. The process according to claim 1, wherein said at least one alkoxyphenol is selected from the group comprising guaiacol, 3-methoxycatechol, 2-methoxyresorcinol, 2,3-dimethoxyphenol and syringol.

8. The process according to claim 1, wherein said at least one alkoxyphenol is selected from the group comprising guaethol, 3-ethoxycatechol, 2-ethoxyresorcinol, 2,3-diethoxyphenol and 2,6- diethoxyphenol.

9. The process according to claim 1, wherein said at least one acidic catalyst is a anhydrous strongly Br0nsted acidic catalyst.

10. The process according to claim 1, wherein said at least one soluble acid is selected from the group comprising strongly acidic hydracids, oxyacids, sulfonic acids and fluorosulfonic acids.

11. The process according to claim 1, wherein said at least one acidic ion-exchange resin comprises strongly acidic sulfonated ion-exchange resins like Amberlyst-15, Amberlyst-XNIOIO, Dowex D 2030, Nafion NR50 and Nafion SAC13.

12. The process according to claim 1, wherein said at least one acidic clay comprises a strongly acidic clay like montmorillonite (K10, K30 or KSF) or bentonite.

13. The process according to claim 1, wherein said at least one acidic zeolite comprises:

two or three interconnected and non-parallel channel systems, wherein at least one of said channel systems comprises 10- or more-membered ring channels; and a framework S1/X2 ratio of at least 24 as measured by NMR; or

three interconnected and non-parallel channel systems, wherein at least two of said channel systems comprise 10- or more-membered ring channels; and a framework S1/X2 ratio of at least 12 as measured by NMR;

wherein each X is Al or B.

14. The process according to claim 13, wherein at least one of said interconnected and non-parallel channel systems comprises 12- or more membered ring channels.

15. The process according to claim 1, wherein said acidic catalyst has a Br0nsted acid density between 0.05 and 6.5 mmol/g dry weight.

16. The process according to claim 1, wherein said zeolite comprises a BEA topology, a MFI topology, a FAU topology, a MEL topology, a FER topology, or a MWW topology.

17. The process according to claim 1, wherein said zeolite comprises a FAU topology.

18. The process according to claim 1, wherein X is Al.

19. The process according to claim 1, wherein said zeolite comprises at least three interconnecting and non-parallel channel systems.

20. The process according to claim 1, wherein said (alk-l-enyl)alkoxyphenol is provided in a composition comprising said (alk-l-enyl)alkoxyphenol in a concentration of a least 0.01 wt% based on a total weight of the composition.

21. The process according to claim 1, wherein said process is performed under batch, semi-batch or continuous conditions.

22. The process according to claim 1, wherein said (alk-l-enyl)alkoxyphenol and alkoxyphenol are at least 1 wt% derived from bio-based material.

23. The process according to claim 22, wherein said bio-based material comprises at least one lignocellulosic material, plant material, bio-based oil, pyrolysis oil, biorefinery waste, or a combination thereof.

24. The process according to any one of the claims 1-23, further comprising converting said ortho alkoxy bisphenol monomers to polymers.

25. The method according to claim 24, wherein said polymers are thermoplastics or thermosetting resins.

26. The method according to claim 24, wherein said polymers are polycarbonates (PC), polyiminocarbonates (PIC), polyesters (PE), polyester-styrenes, polyurethanes, polyarylates, polyethers, polysulfones (PSU), polyarylsulfones, polyethersulfones (PESU), polyarylethersulfone (PAES), polyetheretherketones (PEEK), polyaryletherketones (PAEK), polyacetals, polyketones, alkylphenolic polymers, polyoxalates, polyalylates, epoxy resins, phenolic resins, vinyl ester resins, polyphenylene ether resins, polyphenylene sulphide resins, polyetherimide resins, cyanate ester resins, benzoxazine resins, bismaleimide resins and other end-capped resins and any combination thereof.

27. The method according to claim 25, wherein said thermoplastics are polycarbonates, produced by reaction of said ortho alkoxy bisphenol monomers with a carbonate source selected from the group consisting of cyclic carbonates, dialkyl carbonates, diaryl carbonates, chloroformates, p- nitrophenyl chloroformate, phosgene, diphosgene, triphosgene (BTC), Λ/,Λ/'-carbonyldiimidazole (CDI), disuccinimidyl carbonate (DSC), and bis(2-pyridyl) carbonate.

28. The method according to claim 25, wherein said thermoplastics are polyesters, produced by reaction of said ortho alkoxy bisphenol monomers with a saturated or unsaturated aliphatic diacid, or derivatives thereof, selected from the group consisting of oxalic acid, malonic acid, maleic acid, fumaric acid, succinic acid, adipic acid, muconic acid, citraconic, mesaconic and itaconic acid, and/or anhydrides, Ci_6alkyl esters, C6-ioaryl esters and/or acid chlorides thereof.

29. The method according to claim 25, wherein said thermoplastics are polyesters, produced by reaction of said ortho alkoxy bisphenol monomers with derivatives of aromatic dicarboxylic acids selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, 2,5-

furandicarboxylic acid, and corresponding thiophene or IH-pyrrole analogues, and/or anhydrides, Ci-6alkyl esters, C6-ioaryl esters and/or acid chlorides thereof.