Renewable Non-Carcinogenic Bio Oil-Derived Residue Compositions, and Methods of Making and Using
Disclosed are substantially non-carcinogenic bio oil-derived residue compositions produced from the pyrolysis or thermo catalytic conversion of biomass, and their use as solvents in the production of tires.
1 . A bio oil-derived residue composition having an initial boiling point of at least about 650° F., and comprising at least about 70 wt. % aromatic hydrocarbons, wherein the aromatic hydrocarbons comprise polycyclic aromatic compounds, and wherein the bio oil-derived residue composition comprises less than about 3 wt. % of the polycyclic aromatic compounds containing at least 4 rings.
2 . The bio oil-derived residue composition of claim 1 comprising less than about 20 wt % of the polycyclic aromatic compounds having 3 rings and at least 18 carbons per molecule.
3 . The bio oil-derived residue composition of claim 2 where the polycyclic aromatic compounds having 3 rings and at least 18 carbons per molecule are selected from the group consisting of anthracenes, phenanthrenes, and mixtures thereof.
4 . The bio oil-derived residue composition of claim 1 wherein the polycyclic aromatic compounds having at least 4 rings comprise substitutable carbons, and wherein at least about 50% of the substitutable carbons are substituted with an alkyl group selected from the group consisting of methyl, ethyl, propyl, butyl, and combinations thereof.
5 . The bio oil-derived residue composition of claim 1 wherein less than about 1 wt. % of the polycyclic aromatic compounds comprise an unsubstituted bay region which can form a bay region diol epoxide.
6 . The bio oil-derived residue composition of claim 1 wherein the polycyclic aromatic compounds comprise bay-region-containing polycyclic aromatic compounds.
7 . The bio oil-derived residue composition of claim 6 wherein the bay-region-containing polycyclic aromatic compounds are selected from the group consisting of alkyl-substituted: phenanthrene, chrysene, benzo(a)pyrene, dibenzo(a,e)pyrene, dibenzo(a,h)pyrene, dibenzo(a,l)pyrene, dibenz(a,h)anthracene, perylene, benzo(ghi)perylene, tetraphene, pentaphene, higher cata-condensed homologues thereof, and combinations thereof.
8 . The bio oil-derived residue composition of claim 6 wherein at least about 70% of the bay regions of the bay-region-containing polycyclic aromatic compounds are substituted with an alkyl group.
9 . The bio oil-derived residue composition of claim 8 wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, butyl, and combinations thereof.
10 . The bio oil-derived residue composition of claim 1 having a mutagenicity index (MI), as measured by the Modified Ames Test (ASTM E1687), of less than about 3.0.
11 . The bio oil-derived residue composition of claim 1 having a dimethyl sulfoxide extract weight, as measured by IP346, of less than about 3 weight %.
12 . The bio oil-derived residue composition of claim 1 wherein at least about 99% of the polycyclic aromatic compounds have from 3 to 7 rings.
13 . The bio oil-derived residue composition of claim 1 wherein at least about 3 wt. % of the polycyclic aromatic compounds each have from 4 to 7 rings and wherein either 0 or 1 ring of each of the polycyclic aromatic compounds is hydrogenated.
14 . The bio oil-derived residue composition of claim 1 , wherein the bio oil-derived residue composition is prepared by a process comprising:
a) converting biomass in a conversion reactor containing a heat transfer media to thereby produce a conversion reactor effluent comprising vapor conversion products;
b) condensing at least a portion of the vapor conversion products to produce a condensate comprising bio-oil and water, wherein the bio-oil has a total organic oxygen content of less than about 40 wt. %;
c) hydrotreating the bio-oil with hydrogen in a hydrotreater reactor to produce a hydrotreater reactor effluent;
d) separating a total liquid product having less than about 3 wt % organic oxygen from the hydrotreater reactor effluent, and
e) separating the bio oil-derived residue composition from the total liquid product.
15 . The bio oil-derived residue composition of claim 14 wherein the condensate is subjected to hydrotreatment forming a hydrotreated condensate and the bio-oil is separated from the water in the hydrotreated condensate prior to step c).
16 . The bio oil-derived residue composition of claim 14 wherein the heat transfer media comprises a catalyst, the bio-oil has a total organic oxygen content of less than about 25 wt. %, and the bio-oil is separated from the water in the condensate prior to step c).
17 . The bio oil-derived residue composition of claim 14 wherein the total liquid product is separated in step e) using atmospheric distillation.
18 . The bio oil-derived residue composition of claim 14 wherein the total liquid product is separated in step e) using vacuum distillation.
19 . The bio oil-derived residue composition of claim 14 wherein the total liquid product is separated in step e) using adsorption.
20 . The bio oil-derived residue composition of claim 14 wherein the total liquid product is separated in step e) using a size selective membrane.
21 . The bio oil-derived residue composition of claim 14 wherein the total liquid product is separated in step e) using a liquid extraction unit.
22 . A tire compound comprising:
i) a bio oil-derived residue composition having an initial boiling point of at least about 650° F., and comprising at least about 70 wt. % aromatic hydrocarbons, wherein the aromatic hydrocarbons comprise polycyclic aromatic compounds, and wherein the bio oil-derived residue composition comprises less than about 3 wt. % of the polycyclic aromatic compounds containing at least 4 rings;
ii) a polymer; and
iii) a filler.
23 . The tire compound of claim 22 wherein the polymer is selected from the group consisting of styrene-butadiene resin, ethylene propylene diene monomer, butyl rubber, and combinations thereof.
24 . The tire compound of claim 22 wherein the filler is selected from the group consisting of carbon black, silica, and combinations thereof.
25 . A process for producing a bio oil-derived residue composition comprising:
a) converting biomass in a conversion reactor containing a heat transfer media to thereby produce a conversion reactor effluent comprising vapor conversion products;
b) condensing at least a portion of the vapor conversion products to produce a condensate comprising bio oil and water, wherein the bio-oil has a total organic oxygen content of less than about 40 wt. %;
c) hydrotreating the bio-oil with hydrogen in a hydrotreater reactor to produce a hydrotreater reactor effluent;
d) separating a total liquid product from the hydrotreater reactor effluent, and
e) separating the bio oil-derived residue composition from the total liquid product, wherein the bio oil-derived residue composition has an initial boiling point of at least about 650° F., and comprises at least about 70 wt. % aromatic hydrocarbons, wherein the aromatic hydrocarbons comprise polycyclic aromatic compounds, and wherein the bio oil-derived residue composition comprises less than about 3 wt. % of the polycyclic aromatic compounds containing at least 4 rings.
26 . The process of claim 25 wherein the condensate is subjected to hydrotreatment forming a hydrotreated condensate and the bio-oil is separated from the water in the hydrotreated condensate prior to step c).
27 . The process of claim 25 wherein the heat transfer media comprises a catalyst, the bio-oil has a total organic oxygen content of less than about 25 wt. %, and the bio-oil is separated from the water in the condensate prior to step c).
28 . The process of claim 25 wherein the bio oil-derived residue composition comprises less than about 20 wt % of the polycyclic aromatic compounds having 3 rings and at least 18 carbons per molecule.
29 . The process of claim 28 where the polycyclic aromatic compounds having 3 rings and at least 18 carbons per molecule are selected from the group consisting of anthracenes, phenanthrenes, and mixtures thereof.
30 . The process of claim 25 wherein the polycyclic aromatic compounds having at least 4 rings comprise substitutable carbons, and wherein at least about 50% of the substitutable carbons are substituted with an alkyl group selected from the group consisting of methyl, ethyl, propyl, butyl, and combinations thereof.
31 . The process of claim 25 wherein less than about 1 wt. % of the polycyclic aromatic compounds comprise an unsubstituted bay region which can form a bay region diol epoxide.
32 . The process of claim 25 wherein the polycyclic aromatic compounds comprise bay-region-containing polycyclic aromatic compounds.
33 . The bio oil-derived residue composition of claim 32 wherein the bay-region-containing polycyclic aromatic compounds are selected from the group consisting of alkyl-substituted: phenanthrene, chrysene, benzo(a)pyrene, dibenzo(a,e)pyrene, dibenzo(a,h)pyrene, dibenzo(a,l)pyrene, dibenz(a,h)anthracene, perylene, benzo(ghi)perylene, tetraphene, pentaphene, higher cata-condensed homologues thereof, and combinations thereof.
34 . The process of claim 32 wherein at least about 70% of the bay regions of the bay-region-containing polycyclic aromatic compounds are substituted with an alkyl group.
35 . The process of claim 25 wherein the bio oil-derived residue composition has a mutagenicity index (MI), as measured by the Modified Ames Test (ASTM E1687), of less than about 3.0.
36 . The process of claim 25 wherein the bio oil-derived residue composition has a dimethyl sulfoxide extract weight, as measured by IP346, of less than about 3 wt. %.
37 . The process of claim 25 wherein at least about 99 wt. % of the polycyclic aromatic compounds each have from 3 to 7 rings.
38 . The process of claim 25 wherein at least about 3 wt. % of the polycyclic aromatic compounds each have from 4 to 7 rings and wherein either 0 or 1 ring of each of the polycyclic aromatic compounds is hydrogenated.