WO2020062060A1 - Method for Purifying Xylose - Google Patents
Method for Purifying Xylose Download PDFInfo
- Publication number
- WO2020062060A1 WO2020062060A1 PCT/CN2018/108415 CN2018108415W WO2020062060A1 WO 2020062060 A1 WO2020062060 A1 WO 2020062060A1 CN 2018108415 W CN2018108415 W CN 2018108415W WO 2020062060 A1 WO2020062060 A1 WO 2020062060A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- xylose
- quaternary ammonium
- ammonium compound
- alkyl
- benzyl
- Prior art date
Links
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 title claims abstract description 118
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 title claims abstract description 59
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 26
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001450 anions Chemical group 0.000 claims description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 229960004670 didecyldimethylammonium chloride Drugs 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- -1 sawdusts Chemical compound 0.000 description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- 238000000746 purification Methods 0.000 description 12
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 9
- 239000002699 waste material Substances 0.000 description 7
- 229920002488 Hemicellulose Polymers 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 239000012978 lignocellulosic material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910021653 sulphate ion Inorganic materials 0.000 description 4
- 229920001221 xylan Polymers 0.000 description 4
- 150000004823 xylans Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/002—Xylose
Definitions
- the present invention relates to a method for purifying xylose, wherein the xylose is purified by using a quaternary ammonium compound.
- the present invention also relates to a xylose composition obtained by said method.
- Xylose is a pentose sugar which is widely used for applications such as food additives and pharmaceutical products. It is prepared by the acid hydrolysis of ligno-cellulosic materials containing hemicelluloses having a high proportion of xylose units or xylans in their molecules. In addition to hemicelluloses, ligno-cellulosic material to contain lignin, cellulose and other carbohydrates. Furthermore, hemicellulose molecules contain, in addition to xylans, units of other sugars. Hemicelluloses derived from different ligno-cellulosic materials vary in structure, some containing a greater proportion of xylans in their molecules than are contained in the molecules of other hemicelluloses. In the production of xylose, it is necessary to separate lignin, cellulose and other materials from the product of the initial hydrolysis.
- the manufacturing process of xylose generally comprises steps of (I) hydrolyzing plant-derived materials which contain xylose, such as sawdusts, straws, and cornstalks, so as to obtain a raw xylose-containing liquid, (II) purification, and (III) crystallization.
- the raw xylose-containing liquid in (I) is normally very dark and contains impurities.
- the impurities mainly include side products of Maillard reaction, lignins, and aromatic pigments. The impurities have to be removed so as to obtain xylose with high purity and good quality.
- wastes from papermaking industry are also used as raw materials for making xylose.
- the wastes from papermaking industry contain not only celluloses, lignins, but also impurities like chlorinated aromatic hydrocarbons, polycyclic aromatic hydrocarbons. In such case, purification becomes more difficult.
- the wastes are processed into a xylose containing syrup, which is subsequently purified by using activated carbons, ion exchange resins or membrane filters.
- US Patent No. US 5340403 B2 disclosed a process in which a xylose containing syrup is decolored by activated carbon.
- activated carbon can absorb indiscriminately impurities as well as xylose which is the desired product. For this reason, adding large amount of activated carbon not only leads to high costs, but also cause reduced yield of xylose.
- ion exchange resins can be used in decolorization of xylose syrup.
- US Patent No. US3985815 B1 discloses a method using crosslinked polystyrene.
- the purification process utilizing the ion exchange resin is time consuming and require use of water in large amount.
- raw hydrolyzed xylose liquid or syrup generally has high temperature and strong acidity. It can thus damage the resin and generate large amount of liquid waste which can be hazardous to environment.
- Membrane filter is also an option, however this method is expensive and the purification efficiency is not satisfactory.
- the present invention aims at developing a method for purifying xylose, which has good purification efficiency and which is fast and cost efficient.
- the present invention relates to a method for purifying xylose, comprising a step of adding to a raw xylose-containing liquid a quaternary ammonium compound.
- the quaternary ammonium compound is according to the general formula (I) :
- R 1 , R 2 , R 3 and R 4 which may be the same or different, is a C 1 -C 30 hydrocarbyl group, optionally containing a hetero atom, or an ester or amide group;
- X is an anion
- y is the valence of X.
- the quaternary ammonium compound is according to the general formula (II)
- R 1 , R 2 , R 3 and R 4 which may be the same or different, is a C 1 -C 30 hydrocarbyl group, wherein at least one of R 1 , R 2 , R 3 and R 4 is a C 10 -C 28 alkyl or hydroxyalkyl group;
- X is an anion
- y is the valence of X.
- the quaternary ammonium compound is according to general formula (III)
- R 1 is a C 10 -C 28 alkyl or hydroxyalkyl, each of R 2 and R 3 is methyl, R 4 is benzyl,
- X is an anion
- y is the valence of X.
- the quaternary ammonium compound is according to general formula (IV)
- R 1 and R 2 is independently a C 10 -C 28 alkyl or hydroxyalkyl, R 3 is methyl,
- R 4 is methyl or benzyl
- X is an anion
- y is the valence of X.
- the present invention also relates to a xylose composition, wherein the xylose composition contains a xylose obtained by using the method of the present invention.
- any particular upper concentration, weight ratio or amount can be associated with any particular lower concentration, weight ratio or amount.
- hydrocarbyl should be understand as including but not limited to saturated and unsaturated hydrocarbyl groups, straight, branched or cyclic hydrocarbyl groups, aliphatic or aromatic groups, substituted or unsubstituted hydrocarbyl groups, etc..
- Hydrocarbyl group includes not only single species hydrocarbyl like methyl, ethyl and so on, but also mixed hydrocarbyls from natural sources (animal and plants) , for example, palmityl alkyl and tallow alkyl.
- alkyl means a saturated hydrocarbon radical, which may be straight, branched or cyclic, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl, n-hexyl, cyclohexyl.
- hydroxyalkyl means an alkyl radical, which is substituted with a hydroxyl groups, such as hydroxymethyl, hydroxyethyl, hydroxypropyl, and hydroxydecyl.
- aryl means a monovalent unsaturated hydrocarbon radical containing one or more six - membered carbon rings in which the unsaturation may be represented by three conjugated double bonds, which may be substituted one or more of carbons of the ring with hydroxy, alkyl, alkenyl, halo, haloalkyl, or amino, such as, for example, phenoxy, phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, trichloromethylphenyl, aminophenyl.
- aralkyl means an alkyl group substituted with one or more aryl groups, such as, for example, phenylmethyl, phenylethyl, triphenylmethyl.
- quaternary ammonium compound (also referred to as “quat” ) , as used herein, means a compound containing at least one quaternized nitrogen wherein the nitrogen atom is attached to four organic groups.
- the quat may comprise one or more quaternized nitrogen atoms.
- the quat comprises only one quaternized nitrogen atom.
- xylose-containing liquid means a liquid or a liquid mixture which contains xylose, raw xylose, or other raw materiala from which xylose can be made.
- the liquid here should include but not limited to aqueous solutions and melts containing xylose or raw xylose.
- the method of the present invention comprises a step of adding a quaternary ammonium compound into a raw xylose-containing liquid.
- the raw xylose-containing liquid may be obtained by hydrolysis of ligno-cellulosic materials containing hemicelluloses that have a high proportion of xylose units or xylans in their molecules.
- the raw xylose-containing liquid may be obtained by hydrolysis of cornstalk, sawdust, waste of papermaking industry, or straw.
- the raw xylose-containing liquid may be a direct product of the hydrolysis treatment.
- the raw xylose-containing liquid may be a diluted solution, a diluted mixture, or a concentrated syrup.
- raw materials can be hydrolyzed in presence of an acid or enzyme, and/or by heating.
- acid or enzyme e.g., benzyl alcohol, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl, naric acid, or hydrochloric acid are preferred for acid treatment.
- a temperature below boiling point (of water or other solvent) is preferred, 95°C or below is more preferred.
- the raw material can be mixed with the quaternary ammonium compound before hydrolyzation, during hydrolyzation or after hydrolyzation.
- the raw material such as the raw xylose-containing liquid, may also be filtered before addition of the quaternary ammonium compound.
- the quaternary ammonium compound, once added, can be mixed and/or stirred with the raw xylose–containing liquid.
- the xylose-containing liquid can be heated to a predetermined temperature before adding the quaternary ammonium compound.
- the heated solution can be mixed by stirring then.
- the raw xylose-containing liquid can be heated after adding the quaternary ammonium compound. In this case, the solution can be stirred before or after being heated.
- the raw xylose-containing liquid when the raw xylose-containing liquid is heated in the hydrolyzation step, it can be kept warm (preferably for a short period) till adding the quaternary ammonium compound, which is energy-efficient since the xylose-containing liquid need not to be heated again.
- heating temperature There is no limit on heating temperature.
- a temperature below boiling point of water or other solvent
- 95°C or below is more preferred
- the quat is preferably added in form of a diluted aqueous solution.
- the quat may be added in form of a concentrated aqueous solution or a solid, for example a powder or cake.
- the quat may also be added in form of non-aqueous solution, or solution of mixed solvent, for example, alcohol or water-alcohol can be used as solvent.
- the solution may contain water, ethanol isopropanol or isopropanol as solvent.
- the quat may also be added with other addictive like flocculant, activated carbon or other adsorbents.
- Dosage of the quaternary ammonium compound may be from 200 to 5000 ppm, preferably from 200 to 3000 ppm, more preferably from 500 to 3000 ppm, even more preferably from 1000 to 2000 ppm.
- the method of the present invention is characterized in that adding the quaternary ammonium compound, preferably into a raw xylose-containing liquid obtained by hydrolyzation of raw material.
- the purified xylose can be subject to further steps which are known by a skilled person, such as seperration (for example, by filtration or centrifugalization) , concentration (for example, by evaporation, preferably at a reduced pressure and/or at a high temperature) , crystallization, washing and drying the crystallized xylose.
- the purification method of the present invention can be used solely or can be used in combination with other purification methods, for example, purification by using membrane filter, activated carbon, or ion exchange resin.
- the quaternary ammonium compound can be added before or after any one of the steps above.
- the quaternary ammonium compound is preferably according to the general formula (I) :
- R 1 , R 2 , R 3 and R 4 which may be the same or different, is a C 1 -C 30 hydrocarbyl group, typically an alkyl, hydroxyalkyl, aryl or aralkyl, optionally containing a heteroatom, or an ester or amide group;
- X is an anion, for example halide, such as Cl or Br, sulphate, alkyl sulphate, nitrate or acetate;
- y is the valence of X.
- the quaternary ammonium compound is according to the general formula (II)
- R 1 , R 2 , R 3 and R 4 which may be the same or different, is a C 1 -C 30 hydrocarbyl group, typically an alkyl, hydroxyalkyl, aryl or aralkyl, wherein at least one of R 1 , R 2 , R 3 and R 4 is a C 10 -C 28 alkyl or hydroxyalkyl group;
- X is an anion, for example halide, such as Cl or Br, sulphate, alkyl sulphate, nitrate or acetate;
- y is the valence of X.
- R 1 ⁇ R 4 can be replaced by a heteroatom like O, S and N, preferably O.
- number of carbon atoms being replaced by heteroatom is not limited, preferably 4 or less carbon atoms are replaced by heteroatom, more preferably two or three carbon atoms are replaced by heteroatom, most preferably one.
- R 1 , R 2 , R 3 and R 4 may be an alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl, n-hexyl, cyclohexyl, dodecyl, tetradecyl, cetyl, octadecyl, eicosyl.
- R 1 , R 2 , R 3 and R 4 may be an hydroalkyl of the alkyls listed above.
- R 1 , R 2 , R 3 and R 4 may be an aryl such as phenoxy, phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, trichloromethylphenyl, aminophenyl.
- R 1 , R 2 , R 3 and R 4 may be an alkylaryl, such as benzyl phenylethyl, phenyl-n-propyl, phenyl-iso-propyl, phenyl-n-butyl, phenyl-sec-butyl, phenyl-t-butyl, phenylpentyl, phenyl-n-hexyl, cyclohexyl, phenyldodecyl, phenyltetradecyl, phenylcetyl, phenyloctadecyl, phenyleicosyl.
- alkylaryl such as benzyl phenylethyl, phenyl-n-propyl, phenyl-iso-propyl, phenyl-n-butyl, phenyl-sec-butyl, phenyl-t-butyl, phenylpentyl,
- X may be anions like Cl - , Br - , F - , I - , SO 4 2- , HSO 4 - , PO 3 3- , HPO 3 2- , H 2 PO 3 - , CO 3 2- , HCO 3 - , NO 3 - , preferably halide ion, like Cl - or Br - .
- the anion can also be the anion part of organic acids like acetic acid, maleic acid, fumaric acid, iconic acid.
- the quaternary ammonium compound is according to general formula (III)
- R 1 is a C 10 -C 28 alkyl or hydroxyalkyl, each of R 2 and R 3 is methyl, R 4 is benzyl,
- X is an anion
- y is the valence of X.
- the quaternary ammonium compound is according to general formula (IV)
- R 1 and R 2 is independently a C 10 -C 28 alkyl or hydroxyalkyl, R 3 is methyl, R 4 is methyl or benzyl
- X is an anion
- y is the valence of X.
- Examples of the quaternary ammonium compound suitable for the invention include and are not limited to didecyl dimethyl ammonium chloride, C 12-16 -alkyldimethyl benzyl ammonium chloride, hydrogenated tallowdimethyl benzyl ammonium chloride, dihydrogenated tallow benzyl methyl ammonium chloride, and dihydrogenated tallowdimethylammonium chloride.
- quaternary ammonium compound suitable for the invention include and are not limit to D1217S, 1831 and T05 (all from Solvay) .
- the quaternary ammonium compound may comprise one or more of the compounds above. It can be used with other functional addictive
- Step 1 Waste of papermaking industry was used as the raw material, to obtain a raw xylose liquid by acid hydroxylation (add sulfuric acid to pH ⁇ 1) , and heat the raw xylose liquid to 70 ⁇ 95°C.
- Step 2 add calculated amount of the quaternary ammonium compound on the weight of raw xylose liquid and stir for approx. 1 min at 70 ⁇ 95°C.
- Step 4 filter and test the color value.
- Step 1 collect the clear filtrate (adjust pH to 4.5)
- Step 2 check the brix with Abbe Refractometer (from ATAGO Company)
- Step 3 check the adsorption at 420nm using 1 cm cuvette
- color value (A420 /Brix*L) *10 5 , unit is IU 420
- A420 is the adsorption at 420 nm
- Brix is the brix of the xylose liquid measured by Abbe Refractometer
- Color removal (%) [color value (raw liquid) –color value (clear liquid) ] /color value (raw liquid) *100
- E1 refers to Example 1 and so on.
- CE1 refers to Comparative Example 1 and so on.
- the quaternary ammonium compound of the present invention provided higher color reduction compared to PAC or the tertiary amine.
- the quat according to the invention provided reduced scaling. This is particular advantageous when the purified xylose is subject to concentration by heating. High scale will be harmful for the equipment used for concentration step and will require additional efforts to remove the scales in the concentration equipment from time to time.
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Abstract
A method for purifying xylose, comprising a step of adding to a raw xylose-containing liquid a quaternary ammonium compound.
Description
The present invention relates to a method for purifying xylose, wherein the xylose is purified by using a quaternary ammonium compound. The present invention also relates to a xylose composition obtained by said method.
Background Arts
Xylose is a pentose sugar which is widely used for applications such as food additives and pharmaceutical products. It is prepared by the acid hydrolysis of ligno-cellulosic materials containing hemicelluloses having a high proportion of xylose units or xylans in their molecules. In addition to hemicelluloses, ligno-cellulosic material to contain lignin, cellulose and other carbohydrates. Furthermore, hemicellulose molecules contain, in addition to xylans, units of other sugars. Hemicelluloses derived from different ligno-cellulosic materials vary in structure, some containing a greater proportion of xylans in their molecules than are contained in the molecules of other hemicelluloses. In the production of xylose, it is necessary to separate lignin, cellulose and other materials from the product of the initial hydrolysis.
The manufacturing process of xylose generally comprises steps of (I) hydrolyzing plant-derived materials which contain xylose, such as sawdusts, straws, and cornstalks, so as to obtain a raw xylose-containing liquid, (II) purification, and (III) crystallization. The raw xylose-containing liquid in (I) is normally very dark and contains impurities. The impurities mainly include side products of Maillard reaction, lignins, and aromatic pigments. The impurities have to be removed so as to obtain xylose with high purity and good quality.
In recent years, to make good use of wastes, wastes from papermaking industry are also used as raw materials for making xylose. However, it remains a challenge to separate xylose from these wastes. The wastes from papermaking industry contain not only celluloses, lignins, but also impurities like chlorinated aromatic hydrocarbons, polycyclic aromatic hydrocarbons. In such case, purification becomes more difficult. Conventionally, the wastes are processed into a xylose containing syrup, which is subsequently purified by using activated carbons, ion exchange resins or membrane filters.
For example, US Patent No. US 5340403 B2 disclosed a process in which a xylose containing syrup is decolored by activated carbon. However, there are limitations on decolorization ability of activated carbon, because activated carbon can absorb indiscriminately impurities as well as xylose which is the desired product. For this reason, adding large amount of activated carbon not only leads to high costs, but also cause reduced yield of xylose.
Also, ion exchange resins can be used in decolorization of xylose syrup. For example, US Patent No. US3985815 B1 discloses a method using crosslinked polystyrene. However, the purification process utilizing the ion exchange resin is time consuming and require use of water in large amount. Furthermore, raw hydrolyzed xylose liquid or syrup generally has high temperature and strong acidity. It can thus damage the resin and generate large amount of liquid waste which can be hazardous to environment. Membrane filter is also an option, however this method is expensive and the purification efficiency is not satisfactory.
Based on the above, the present invention aims at developing a method for purifying xylose, which has good purification efficiency and which is fast and cost efficient.
Summary of Invention
It has been found that the above objective can be achieved by the present invention in which a quaternary ammonium compound is used for purifying xylose. Use of the quaternary ammonium compound allows high selectivity in removing the undesired impurities and dosage of the reagents required is low. In addition, the purification process is fast and cost efficient.
The present invention relates to a method for purifying xylose, comprising a step of adding to a raw xylose-containing liquid a quaternary ammonium compound.
Preferably, the quaternary ammonium compound is according to the general formula (I) :
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (I)
wherein:
R
1, R
2, R
3 and R
4, which may be the same or different, is a C
1-C
30 hydrocarbyl group, optionally containing a hetero atom, or an ester or amide group;
X is an anion;
y is the valence of X.
In some embodiments, the quaternary ammonium compound is according to the general formula (II)
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (II)
wherein:
R
1, R
2, R
3 and R
4, which may be the same or different, is a C
1-C
30 hydrocarbyl group, wherein at least one of R
1, R
2, R
3 and R
4 is a C
10-C
28 alkyl or hydroxyalkyl group;
X is an anion;
y is the valence of X.
In some embodiments, the quaternary ammonium compound is according to general formula (III)
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (III)
wherein R
1 is a C
10-C
28 alkyl or hydroxyalkyl, each of R
2 and R
3 is methyl, R
4 is benzyl,
X is an anion,
y is the valence of X.
In some embodiments, the quaternary ammonium compound is according to general formula (IV)
[N
+
(R
1) (R
2) (R
3) (R
4) ]
yX
- (IV)
wherein R
1 and R
2 is independently a C
10-C
28 alkyl or hydroxyalkyl, R
3 is methyl,
R
4 is methyl or benzyl,
X is an anion,
y is the valence of X.
The present invention also relates to a xylose composition, wherein the xylose composition contains a xylose obtained by using the method of the present invention.
The present invention is described by detailed embodiments and examples below only for the purpose of better understanding, these embodiments and examples should not be interpreted as limit to the present invention.
Throughout the description, including the claims, the term "comprising one" or “comprising a" should be understood as being synonymous with the term "comprising at least one" , unless otherwise specified, and "between" should be understood as being inclusive of the limits.
It should be noted that in specifying any range of concentration, weight ratio or amount, any particular upper concentration, weight ratio or amount can be associated with any particular lower concentration, weight ratio or amount.
As used herein, “hydrocarbyl” should be understand as including but not limited to saturated and unsaturated hydrocarbyl groups, straight, branched or cyclic hydrocarbyl groups, aliphatic or aromatic groups, substituted or unsubstituted hydrocarbyl groups, etc.. Hydrocarbyl group includes not only single species hydrocarbyl like methyl, ethyl and so on, but also mixed hydrocarbyls from natural sources (animal and plants) , for example, palmityl alkyl and tallow alkyl.
As used herein, the term "alkyl" means a saturated hydrocarbon radical, which may be straight, branched or cyclic, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl, n-hexyl, cyclohexyl.
As used herein, the term "hydroxyalkyl" means an alkyl radical, which is substituted with a hydroxyl groups, such as hydroxymethyl, hydroxyethyl, hydroxypropyl, and hydroxydecyl.
As used herein, the term "aryl" means a monovalent unsaturated hydrocarbon radical containing one or more six
-membered carbon rings in which the unsaturation may be represented by three conjugated double bonds, which may be substituted one or more of carbons of the ring with hydroxy, alkyl, alkenyl, halo, haloalkyl, or amino, such as, for example, phenoxy, phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, trichloromethylphenyl, aminophenyl.
As used herein, the term "aralkyl" means an alkyl group substituted with one or more aryl groups, such as, for example, phenylmethyl, phenylethyl, triphenylmethyl.
The term “quaternary ammonium compound” (also referred to as “quat” ) , as used herein, means a compound containing at least one quaternized nitrogen wherein the nitrogen atom is attached to four organic groups. The quat may comprise one or more quaternized nitrogen atoms. Preferably, the quat comprises only one quaternized nitrogen atom.
The term “xylose-containing liquid” , as used herein, means a liquid or a liquid mixture which contains xylose, raw xylose, or other raw materiala from which xylose can be made. The liquid here should include but not limited to aqueous solutions and melts containing xylose or raw xylose.
The method of the present invention comprises a step of adding a quaternary ammonium compound into a raw xylose-containing liquid.
The raw xylose-containing liquid may be obtained by hydrolysis of ligno-cellulosic materials containing hemicelluloses that have a high proportion of xylose units or xylans in their molecules. For example, the raw xylose-containing liquid may be obtained by hydrolysis of cornstalk, sawdust, waste of papermaking industry, or straw. The raw xylose-containing liquid may be a direct product of the hydrolysis treatment. Alternatively, the raw xylose-containing liquid may be a diluted solution, a diluted mixture, or a concentrated syrup.
For the hydrolysis treatment, raw materials can be hydrolyzed in presence of an acid or enzyme, and/or by heating. Well-known strong acids like sulfuric acid, nitric acid, or hydrochloric acid are preferred for acid treatment.
When heating is applied in the hydrolysis treatment, a temperature below boiling point (of water or other solvent) is preferred, 95℃ or below is more preferred. For having good hydrolyzation efficiency, it is preferred to heat at 50℃ or above, 60℃ or above is more preferred, 70℃ or above is mostly preferred.
In the method of the present invention, the raw material can be mixed with the quaternary ammonium compound before hydrolyzation, during hydrolyzation or after hydrolyzation. The raw material, such as the raw xylose-containing liquid, may also be filtered before addition of the quaternary ammonium compound.
The quaternary ammonium compound, once added, can be mixed and/or stirred with the raw xylose–containing liquid. For example, the xylose-containing liquid can be heated to a predetermined temperature before adding the quaternary ammonium compound. In this case, the heated solution can be mixed by stirring then. On the other hand, the raw xylose-containing liquid can be heated after adding the quaternary ammonium compound. In this case, the solution can be stirred before or after being heated. As another option, when the raw xylose-containing liquid is heated in the hydrolyzation step, it can be kept warm (preferably for a short period) till adding the quaternary ammonium compound, which is energy-efficient since the xylose-containing liquid need not to be heated again. There is no limit on heating temperature. For the purpose of controlling the process easily, a temperature below boiling point (of water or other solvent) is preferred, 95℃ or below is more preferred, and for having good purification efficiency, it is preferred to heat at 50℃ or above, 60℃ or above is more preferred, 70℃ or above is mostly preferred.
For addition of the quat, the quat is preferably added in form of a diluted aqueous solution. Alternatively, the quat may be added in form of a concentrated aqueous solution or a solid, for example a powder or cake. In some embodiments, the quat may also be added in form of non-aqueous solution, or solution of mixed solvent, for example, alcohol or water-alcohol can be used as solvent. Preferably, the solution may contain water, ethanol isopropanol or isopropanol as solvent. The quat may also be added with other addictive like flocculant, activated carbon or other adsorbents.
Dosage of the quaternary ammonium compound may be from 200 to 5000 ppm, preferably from 200 to 3000 ppm, more preferably from 500 to 3000 ppm, even more preferably from 1000 to 2000 ppm.
The method of the present invention is characterized in that adding the quaternary ammonium compound, preferably into a raw xylose-containing liquid obtained by hydrolyzation of raw material. The purified xylose can be subject to further steps which are known by a skilled person, such as seperration (for example, by filtration or centrifugalization) , concentration (for example, by evaporation, preferably at a reduced pressure and/or at a high temperature) , crystallization, washing and drying the crystallized xylose.
It should be understood that, the purification method of the present invention can be used solely or can be used in combination with other purification methods, for example, purification by using membrane filter, activated carbon, or ion exchange resin. The quaternary ammonium compound can be added before or after any one of the steps above.
The quaternary ammonium compound is preferably according to the general formula (I) :
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (I)
wherein:
R
1, R
2, R
3 and R
4, which may be the same or different, is a C
1-C
30 hydrocarbyl group, typically an alkyl, hydroxyalkyl, aryl or aralkyl, optionally containing a heteroatom, or an ester or amide group;
X is an anion, for example halide, such as Cl or Br, sulphate, alkyl sulphate, nitrate or acetate;
y is the valence of X.
In a preferred embodiment, the quaternary ammonium compound is according to the general formula (II)
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (II) wherein:
R
1, R
2, R
3 and R
4, which may be the same or different, is a C
1-C
30 hydrocarbyl group, typically an alkyl, hydroxyalkyl, aryl or aralkyl, wherein at least one of R
1, R
2, R
3 and R
4 is a C
10-C
28 alkyl or hydroxyalkyl group; X is an anion, for example halide, such as Cl or Br, sulphate, alkyl sulphate, nitrate or acetate;
y is the valence of X.
Some of the carbon atoms in R
1～R
4 can be replaced by a heteroatom like O, S and N, preferably O. In each group, number of carbon atoms being replaced by heteroatom is not limited, preferably 4 or less carbon atoms are replaced by heteroatom, more preferably two or three carbon atoms are replaced by heteroatom, most preferably one.
R
1, R
2, R
3 and R
4, independently, may be an alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl, n-hexyl, cyclohexyl, dodecyl, tetradecyl, cetyl, octadecyl, eicosyl.
R
1, R
2, R
3 and R
4, independently, may be an hydroalkyl of the alkyls listed above.
R
1, R
2, R
3 and R
4, independently, may be an aryl such as phenoxy, phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, chlorophenyl, trichloromethylphenyl, aminophenyl.
R
1, R
2, R
3 and R
4, independently, may be an alkylaryl, such as benzyl phenylethyl, phenyl-n-propyl, phenyl-iso-propyl, phenyl-n-butyl, phenyl-sec-butyl, phenyl-t-butyl, phenylpentyl, phenyl-n-hexyl, cyclohexyl, phenyldodecyl, phenyltetradecyl, phenylcetyl, phenyloctadecyl, phenyleicosyl.
X may be anions like Cl
-, Br
-, F
-, I
-, SO
4
2-, HSO
4
-, PO
3
3-, HPO
3
2-, H
2PO
3
-, CO
3
2-, HCO
3
-, NO
3
-, preferably halide ion, like Cl
-or Br
-. The anion can also be the anion part of organic acids like acetic acid, maleic acid, fumaric acid, iconic acid.
In a preferred embodiment of the invention, the quaternary ammonium compound is according to general formula (III)
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (III)
wherein R
1 is a C
10-C
28 alkyl or hydroxyalkyl, each of R
2 and R
3 is methyl, R
4 is benzyl,
X is an anion,
y is the valence of X.
In another preferred embodiment of the invention, the quaternary ammonium compound is according to general formula (IV)
[N
+ (R
1) (R
2) (R
3) (R
4) ]
yX
- (IV)
wherein R
1 and R
2 is independently a C
10-C
28 alkyl or hydroxyalkyl, R
3 is methyl, R
4 is methyl or benzyl
X is an anion,
y is the valence of X.
Examples of the quaternary ammonium compound suitable for the invention include and are not limited to didecyl dimethyl ammonium chloride, C
12-16-alkyldimethyl benzyl ammonium chloride, hydrogenated tallowdimethyl benzyl ammonium chloride, dihydrogenated tallow benzyl methyl ammonium chloride, and dihydrogenated tallowdimethylammonium chloride.
Further examples of the quaternary ammonium compound suitable for the invention include and are not limit to
D1217S,
1831 and
T05 (all from Solvay) .
In the present invention, the quaternary ammonium compound may comprise one or more of the compounds above. It can be used with other functional addictive
Examples
Process of Purifying Xylose
Step 1: Waste of papermaking industry was used as the raw material, to obtain a raw xylose liquid by acid hydroxylation (add sulfuric acid to pH<1) , and heat the raw xylose liquid to 70～95℃.
Step 2: add calculated amount of the quaternary ammonium compound on the weight of raw xylose liquid and stir for approx. 1 min at 70～95℃.
Step 3: adjust the xylose liquid to pH=4.5 with 0.1 mol/L NaOH aqueous solution.
Step 4: filter and test the color value.
De-coloring Test:
Step 1: collect the clear filtrate (adjust pH to 4.5)
Step 2: check the brix with Abbe Refractometer (from ATAGO Company)
Step 3: check the adsorption at 420nm using 1 cm cuvette
Calculation:
color value = (A420 /Brix*L) *10
5, unit is IU
420
A420 is the adsorption at 420 nm
Brix is the brix of the xylose liquid measured by Abbe Refractometer L is the length of the cuvette, unit is cm, L = 1 cm in this experiment Color removal (%) = [color value (raw liquid) –color value (clear liquid) ] /color value (raw liquid) *100
Anti-scaling Test
Heat the filtrate (pH = 4.5, solids content = about 30%) in a round bottomed flask at about 70℃ to remove about 80%of water, then observe scaling on the flask wall. Anti-scaling rate is rated as below.
Low: large amount of scaling
Medium: small amount of scaling
High: very small amount of scaling
For comparative examples, instead of the quaternary ammonium compound, use 2000ppm of powdered activated carbon, and stir for 1～1.5 hours in step 2, the rest are the same as examples.
The reagents used for purification are detailed in Table 1 and the results are provided in Table 2.
E1 refers to Example 1 and so on. CE1 refers to Comparative Example 1 and so on.
Table 1
| # | Purification Agents | Cas No. |
| E1 | didecyl dimethyl ammonium chloride | 7173-51-5 |
| E2 | C 12-16-alkyldimethyl benzyl ammonium chloride | 68424-85-1 |
| E3 | Hydrogenated tallowdimethyl benzyl ammonium chloride | 8001-54-5 |
| E4 | Dihydrogenated tallow benzyl methyl ammonium chloride | 73049-75-9 |
| E5 | Dihydrogenated tallowdimethyl ammonium chloride | 68002-59-5 |
| CE1 | bis (2-hydroxyethyl) tallowalkyl amine | 61791-44-4 |
| CE2 | powdered activated carbon (PAC) | - |
Table 2
It can be seen that the quaternary ammonium compound of the present invention provided higher color reduction compared to PAC or the tertiary amine. Also, the quat according to the invention provided reduced scaling. This is particular advantageous when the purified xylose is subject to concentration by heating. High scale will be harmful for the equipment used for concentration step and will require additional efforts to remove the scales in the concentration equipment from time to time.
Claims (8)
- A method for purifying xylose, comprising a step of adding to a raw xylose-containing liquid a quaternary ammonium compound.
- The method according to claim 1, wherein the quaternary ammonium compound is according to the general formula (I) :[N + (R 1) (R 2) (R 3) (R 4) ] yX - (I)wherein:R 1, R 2, R 3 and R 4, which may be the same or different, is a C 1-C 30 hydrocarbyl group, optionally containing a hetero atom or an ester or amide group;X is an anion;y is the valence of X.
- The method according to claim 1 or 2, wehrein R 1, R 2, R 3 and R 4, which may be the same or different, is an alkyl, hydroxyalkyl, aryl or aralkyl.
- The method according to any one of claims 1 to 3, wherein the quaternaryammonium compound is according to the general formula (II)[N + (R 1) (R 2) (R 3) (R 4) ] yX - (II)wherein:R 1, R 2, R 3 and R 4, which may be the same or different, is a C 1-C 30 hydrocarbyl group, at least one of R 1, R 2, R 3 and R 4 is a C 10-C 28 alkyl or hydroxyalkyl group;X is an anion;y is the valence of X.
- The method according to any one of claims 1 to 3, wherein the quaternary ammonium compound is according to general formula (III)[N + (R 1) (R 2) (R 3) (R 4) ] yX - (III)wherein R 1 is a C 10-C 28 alkyl or hydroxyalkyl, each of R 2 and R 3 is methyl, R 4 is benzyl,X is an anion,y is the valence of X.
- The method according to any one of claims 1 to 3, wherein the quaternary ammonium compound is according to general formula (IV)[N + (R 1) (R 2) (R 3) (R 4) ] yX - (IV)wherein R 1 and R 2 is independently a C 10-C 28 alkyl or hydroxyalkyl, R 3 is methyl, R 4 is methyl or benzylX is an anion,y is the valence of X.
- The method according to any one of claims 1 to 6, wherein the quaternary ammonium compound is selected from the group consisting of : didecyl dimethyl ammonium chloride, C 12-16-alkyldimethyl benzyl ammonium chloride, hydrogenated tallowdimethyl benzyl ammonium chloride, dihydrogenated tallow benzyl methyl ammonium chloride, and dihydrogenated tallowdimethylammonium chloride .
- A xylose composition, purified by the method according to any one of claims 1 to 7.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2018/108415 WO2020062060A1 (en) | 2018-09-28 | 2018-09-28 | Method for Purifying Xylose |
| CN201880098115.5A CN113039291A (en) | 2018-09-28 | 2018-09-28 | Process for the purification of xylose |
| BR112021005502-9A BR112021005502B1 (en) | 2018-09-28 | METHOD FOR PURIFYING XYLOSE |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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|---|---|---|---|---|
| US3698951A (en) * | 1967-09-29 | 1972-10-17 | Tate & Lyle Ltd | Sugar refining |
| CN101092436A (en) * | 2007-04-06 | 2007-12-26 | 李来锁 | Process engineering for producing oligo xylose through physical exploding smash method |
| CN101812546A (en) * | 2010-04-23 | 2010-08-25 | 广西大学 | Preparation of phosphoric acid composite decolorizer and application method thereof |
| CN103210095A (en) * | 2009-11-11 | 2013-07-17 | 卡博Ua有限公司 | Compositions and processes for improving phosphatation clarification of sugar liquors and syrups |
| WO2017202240A1 (en) * | 2016-05-26 | 2017-11-30 | Rhodia Operations | Method for reducing colour impurities in sugar liquid or syrup |
-
2018
- 2018-09-28 WO PCT/CN2018/108415 patent/WO2020062060A1/en active Application Filing
- 2018-09-28 CN CN201880098115.5A patent/CN113039291A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3698951A (en) * | 1967-09-29 | 1972-10-17 | Tate & Lyle Ltd | Sugar refining |
| CN101092436A (en) * | 2007-04-06 | 2007-12-26 | 李来锁 | Process engineering for producing oligo xylose through physical exploding smash method |
| CN103210095A (en) * | 2009-11-11 | 2013-07-17 | 卡博Ua有限公司 | Compositions and processes for improving phosphatation clarification of sugar liquors and syrups |
| CN101812546A (en) * | 2010-04-23 | 2010-08-25 | 广西大学 | Preparation of phosphoric acid composite decolorizer and application method thereof |
| WO2017202240A1 (en) * | 2016-05-26 | 2017-11-30 | Rhodia Operations | Method for reducing colour impurities in sugar liquid or syrup |
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|---|---|
| BR112021005502A2 (en) | 2021-06-15 |
| CN113039291A (en) | 2021-06-25 |
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