US2009235574A1PendingUtilityA1
Production of Bio-Diesel
Individually held — no corporate assignee on recordPriority: Mar 11, 2005Filed: Feb 27, 2006Published: Sep 24, 2009
Est. expiryMar 11, 2025(expired)· nominal 20-yr term from priority
Y02E50/10C07C 67/03B01J 31/0284B01J 31/0282B01J 31/0279Y02P20/54C11C 3/003B01J 2231/49C11C 3/10B01J 31/0288
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Claims
Abstract
Use of ionic liquids in the production of bio-diesel, wherein the ionic liquid is both a solvent and catalyst, and is stable under reaction conditions.
Claims
exact text as granted — not AI-modified1 - 49 . (canceled)
50 . A method of obtaining Bio-diesel comprising the step of esterifying fatty acids derived from plant or animal in the presence of a stable ionic liquid wherein the ionic liquid is both a solvent and a catalyst.
51 . A method according to claim 50 , wherein the ionic liquid comprises a basic cation and a neutral anion, or a neutral cation and a basic anion, or both a basic cation and a basic anion.
52 . A method according to claim 50 , wherein the ionic liquid comprises an acidic cation and a neutral anion, or a neutral cation and an acidic anion, or both an acidic cation and an acidic anion.
53 . A method according to claim 51 , wherein the basic cation has the formula:
[Cat + -Z-Bas] wherein:
Cat + is a cationic species comprising or consisting of ammonium, phosphonium, pyrazolium, DBU or DBN;
Z is a covalent bond joining Cat + and Bas or one, two, or three aliphatic linking groups each containing 1 to 10 carbon atoms and each optionally one, two, or three oxygen atoms; and Bas is a basic moiety.
54 . A method according to claim 53 , wherein Bas comprises at least one nitrogen, phosphorus, sulphur, oxygen, or boron atom.
55 . A method according to claim 54 , wherein Bas comprises at least one primary, secondary, or tertiary amino group.
56 . A method according to claim 53 , wherein Bas is selected from —N(R 1 )(R 2 ), and —P(R 1 )(R 2 )(R 3 ); and wherein R 1 and R 2 can be the same or different and are each selected from hydrogen, linear or branched alkyl, cycloalkyl, aryl, and substituted aryl.
57 . A method according to claim 56 , wherein R 1 and R 2 are each selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, butyl, sec-butyl, isobutyl, pentyl, hexyl, cyclohexyl, benzyl, and phenyl.
58 . A method according to claim 53 , wherein Z is selected from the group consisting of linear or branched C 1 to C 18 alkanediyl, substituted alkanediyl, dialkanylether, and dialkanylketone.
59 . A method according to claim 58 , wherein Z is selected from the group consisting of —(CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 —CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 )—, —(CH 2 —CH 2 —O—CH 2 —CH 2 )—, and —(CH 2 —CH 2 —O—CH 2 —CH 2 —CH 2 )—.
60 . A method according to claim 53 , wherein Cat + -Z-Bas is selected from:
[N(Z-Bas)(R b )(R c )(R d )] + and [P(Z-Bas)(R b )(R c )(R d )] + wherein:
Bas and Z are as defined above; and
R b , R c , and R d can be the same or different, and are each independently selected from hydrogen, a C 1 to C 40 , straight chain or branched alkyl group, a C 3 to C 8 cycloalkyl group, or a C 6 to C 10 aryl group, wherein said alkyl, cycloalkyl or aryl groups are unsubstituted or may be substituted by one to three groups selected from: C 1 to C 6 alkoxy, C 6 to C 10 aryl, CN, OH, NO 2 , C 7 to C 30 aralkyl and C 7 to C 30 alkaryl.
61 . A method according to claim 53 , wherein Cat + -Z-Bas is selected from:
wherein:
Z, Bas and R b is as defined above.
62 . A method according to claim 61 , wherein Cat + -Z-Bas is selected from:
63 . A method according to claim 53 , wherein Cat+ comprises or consists of 1,3,5-trialkylpyrazolium, 1,2-dialkylpyrazolium, and 1,2,3,5-tetraalkylpyrazolium.
64 . A method according to claim 63 , wherein Cat + -Z-Bas is selected from:
65 . A method according to claim 53 , wherein Cat + -Z-Bas is selected from:
66 . A method according to claim 53 , wherein Cat + -Z-Bas is:
wherein:
Bas, Z and R b are as defined above.
67 . A method according to claim 51 , wherein the basic anion has the formula [X b ] − , and is selected from the group consisting of [F] − , [OH] − , [OR] − , [R—CO 2 ] − , [PO 4 ] 3− , and [SO 4 ] 2− , wherein R is C 1 to C 6 alkyl.
68 . A method according to claim 52 , wherein the acidic cation has the formula:
[Cat + -Z-Acid] wherein:
Cat + is a cationic species;
Z is a covalent bond joining Cat + and Acid containing 1 to 10 carbon atoms and each optionally one, two, or three oxygen atoms; and Acid is an acidic moiety.
69 . A method according to claim 68 , wherein acid is selected from the group consisting of —SO 3 H, —CO 2 H, —SO 3 —PH—R, —SO 3 R, RPO(OH) 2 , and R 2 PO(OH), where R is C 1 to C 6 alkyl or C 1 to C 6 aryl.
70 . A method according to claim 68 , wherein [Cat + ] comprises or consists of a heterocyclic ring structure selected from the group consisting of imidazolium, pyridinium, pyrazolium, thiazolium, isothiazolinium, azathiozolium, oxothiazolium, oxazinium, oxazolium, oxaborolium, dithiozolium, triazolium, selenozolium, oxaphospholium, pyrollium, borolium, furanium, thiophenium, phospholium, pentazolium, indolium, indolinium, oxazolium, isooxazolium, isotriazolium, tetrazolium, benzofuranium, dibenzofuranium, benzothiophenium, dibenzothiophenium, thiadiazolium, pyrimidinium, pyrazinium, pyridazinium, piperazinium, piperidinium, morpholinum, pyranium, annolinium, phthalzinium, quinazolinium, quinaxalinium, quinolinium, isoquinolinium, thazinium, oxazinium, azaannulenium, and pyrrolidinium.
71 . A method according to claim 70 , wherein [Cat + ] comprises or consists of a heterocyclic ring structure selected from the group consisting of pyrazolium, isothiazolinium, tetrazolium, piperidinium, morpholinium, and pyrrolidinium.
72 . A method according to claim 71 , wherein Cat + -Z-Acid is selected from:—
wherein:
Acid and Z are as defined above; and
R b , R c , R d , R e , R f , R g and R h can be the same or different, and are each independently selected from hydrogen, a C 1 to C 40 , straight chain or branched alkyl group, a C 3 to C 8 cycloalkyl group, or a C 6 to C 10 aryl group, wherein said alkyl, cycloalkyl or aryl groups are unsubstituted or may be substituted by one to three groups selected from: C 1 to C 6 alkoxy, C 6 to C 10 aryl, CN, OH, NO 2 , C 7 to C 30 aralkyl and C 7 to C 30 alkaryl, or any two of R b , R c , R d , R e and R f attached to adjacent carbon atoms form a methylene chain —(CH 2 ) q — wherein q is from 8 to 20.
73 . A method according to claim 72 , wherein Cat + -Z-Acid is:
74 . A method according to claim 52 , wherein acidic anion has the formula [X a ] − , and is selected from the group consisting of [HSO 4 ] − , [H 2 PO 4 ] − , [HPO 4 ] 2− , [HCl 2 ] − , and [HX 2 ] − , wherein X=F, Cl, Br, or I.
75 . A method according to claim 51 , wherein the neutral cation comprises or consists of ammonium, phosphonium, borate, pyrazolium, DBU, or DBN.
76 . A method according to claim 75 , wherein the neutral cation is selected from:
[N(R a )(R b )(R c )(R d )] + and [P(R a )(R b )(R c )(R d )] + wherein:
R a , R b , R c , and R d can be the same or different, and are each independently selected from hydrogen, a C 1 to C 40 , straight chain or branched alkyl group, a C 3 to C 8 cycloalkyl group, or a C 6 to C 10 aryl group, wherein said alkyl, cycloalkyl or aryl groups are unsubstituted or are substituted by one to three groups selected from: C 1 to C 6 alkoxy, C 6 to C 10 aryl, CN, OH, NO 2 , C 7 to C 30 aralkyl and C 7 to C 30 alkaryl.
77 . A method according to claim 76 , wherein the neutral cation is selected from:
wherein:
R a is as defined above.
78 . A method according to claim 76 , wherein the neutral cation is selected
from:
79 . A method according to claim 76 , wherein the neutral cation comprises or consists of 1,3,5-trialkyl pyrazolium, 1,2-dialkylpyrazolium, or 1,2,3,5-tetraalkylpyrazolium.
80 . A method according to claim 79 , wherein the neutral cation is selected from:
81 . A method according to claim 76 , wherein the neutral cation is selected from:
82 . A method according to claim 52 , wherein the neutral cation comprises or consists of a heterocyclic ring structure selected from the group consisting of imidazolium, pyridinium, pyrazolium, thiazolium, isothiazolinium, azathiozolium, oxothiazolium, oxazinium, oxazolium, oxaborolium, dithiozolium, triazolium, selenozolium, oxaphospholium, pyrollium, borolium, furanium, thiophenium, phospholium, pentazolium, indolium, indolinium, oxazolium, isooxazolium, isotriazolium, tetrazolium, benzofuranium, dibenzofuranium, benzothiophenium, dibenzothiophenium, thiadiazolium, pyrimidinium, pyrazinium, pyridazinium, piperazinium, piperidinium, morpholenium, pyranium, annolinium, phthalazinium, quinazolinium, quinazalinium, quinolinium, isoquinolinium, thazinium, oxazinium, azaannulenium, and pyrrolodinium.
83 . A method according to claim 82 , wherein the neutral cation comprises or consists of a heterocyclic ring structure selected from the group consisting of pyridinium, pyrazolium, thiazolium, pyrimidinium, piperazinium, piperidinium, morpholinium, quinolinium, isoquinolinium, and pyrrolidinium.
84 . A method according to claim 51 , wherein the neutral anion is a sulfonate, phoshinate, triflamide (amide), triflate, dicyanamide, oxide (phenoxide), or halide anionic species.
85 . A method according to claim 52 , wherein the neutral anion is a sulfonate, phoshinate, triflamide (amide), triflate, dicyanamide, oxide (phenoxide), or halide anionic species.
86 . A method according to claim 84 , wherein the neutral anion is selected from the group consisting of [NTf 2 ] − , [OTf] − , [R—SO 3 ] − , [R 2 PO 2 ] − , [Cl] − , [Br] − , and [I] − ; wherein R is C 1 to C 6 alkyl, or C 1 to C 6 aryl.
87 . A method according to claim 50 , wherein the plant fatty acid is derived from rape seed oil or prioline.
88 . A method according to claim 50 , wherein the bio-diesel product and the ionic liquid are immiscible.
89 . A method according to claim 50 , wherein the bio-diesel product is obtained from the reactants by phase separation.
90 . A method according to claim 50 , wherein the ionic liquid is recycled.
91 . Use of bio-diesel obtained by the method of claim 50 in blending with a petroleum compound.
92 . Use according to claim 91 , wherein the petroleum compound is diesel.Join the waitlist — get patent alerts
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