ES2836850T3 - Compositions of biomass materials for refining - Google Patents

Abstract

A composition comprising lignin, a solvent, and a liquid carrier; where the lignin is obtained from black liquor and constitutes at least 4% by weight of the composition and where the lignin has a weight average molecular weight of not more than 5,000 g / mol, and where the solvent is an organic alcohol, ether or ester, sulfoxide, ketone, aldehyde, or a combination thereof; and wherein the liquid vehicle is a hydrocarbon oil; and wherein the composition further comprises a fatty acid and wherein the weight ratio of the fatty acid to the hydrocarbon oil is from 10: 1 to 1: 1.

Description

DESCRIPTION

Compositions of biomass materials for refining

Field of the invention

The present invention relates to lignin compositions obtained from black liquor in a solvent and a liquid vehicle for, but not restricted to, applications in a refinery, such as a petroleum or biological oil refinery.

Background

Lignin is a complex biopolymer found in plant cell walls and is most commonly derived from wood and some algae. Lignin, cellulose, hemicellulose, and pectin are the main components of the cell wall, and lignin, together with hemicellulose, provide mechanical strength to the cell wall.

Today, lignin can be used as a component, for example in fuel granules as a binder, but it can also be used as an energy source due to its high energy content. Lignin has a higher energy content than cellulose or hemicelluloses and one gram of lignin has an average of 2.27 KJ, which is 30% more than the energy content of cellulosic carbohydrates. The energy content of lignin is similar to that of coal. Currently, due to its combustible value, the lignin removed by the kraft process, sulfate process, in a pulp or paper mill, is generally burned in order to provide energy to run the production process and recover the chemicals of the cooking liquor.

There are several ways to separate the lignin from the black or red liquor obtained after separating the cellulose fibers in the kraft or sulfite process, respectively, during the production processes. One of the most common strategies is ultrafiltration. Lignoboost® is a separation process developed by Innventia AB and the process has been shown to increase lignin yield by using less sulfuric acid. In the Lignoboost® process, the black liquor is taken from the production processes and the lignin is precipitated by adding and reacting with acid, usually carbon dioxide (CO2), and then the lignin is filtered. The lignin filter cake is redispersed and acidified, usually sulfuric acid is used, and the obtained suspension is filtered and washed by displacement washing. Lignin is generally dried and pulverized to be suitable for lime kiln burners or before being pelleted into fuel pellets. Biofuel, such as biogasoline and biodiesel, is a fuel in which energy is derived mainly from biomass material or gases such as wood, corn, sugar cane, animal fat, vegetable oils and so on. However, the biofuel industries are struggling with issues such as the food versus fuel debate, efficiency, and overall raw material supply. At the same time, the pulp or paper manufacturing industries produce large amounts of lignin which often, as described above, is only burned in the factory.

Two common strategies for exploring biomass as a fuel or fuel component are to use pyrolysis oils or hydrogenated lignin. However, these strategies require high pressure and the use of hydrogen gas, which is expensive and can be dangerous. Therefore, there is a need for a less complex method of preparing biomass for the purpose of processing in a biorefinery, but also for processing lignin into fine chemicals or paint or paint additives, for example. US 6072 015, US 2003/100807, US 3105095, WO 2011/003029, US 4 762 529, 2009/145021, US 2009/218062, WO 96/10067, WO 2009/102272 all disclose similar lignin compositions.

Summary of the invention

The present application discloses a composition comprising lignin obtained from black liquor and solvent, liquid carrier and fatty acid where the composition can be used in refinery processes for the production of fuel.

In a first aspect, the present invention relates to a composition according to claim 1.

In a second aspect, the present invention relates to a method for producing the composition according to the present invention comprising:

- providing lignin obtained from black liquor and having a weight average molecular weight of not more than 5,000 g / mol;

- providing a solvent that is an alcohol, ether, sulfoxide, ketone, aldehyde or ester or a combination thereof, a liquid carrier and a fatty acid; Y

- add lignin to the solvent, the liquid vehicle and the fatty acid to obtain a concentration of at least 4% by weight and mix;

wherein the liquid carrier is a hydrocarbon oil and wherein the weight ratio of the fatty acid to the hydrocarbon oil is 10: 1 to 1: 1.

A third aspect refers to the use of the composition of the present invention to prepare fuels such as gasoline and diesel, or diesel and gasoline analogues, or biogasoline or biodiesel; or fuel additives.

A fourth aspect is a fuel obtained from the composition according to the present invention. A fifth aspect of the present invention refers to the use of the composition according to as a concrete crushing aid, set retarder for cement, cement strengthener, antioxidant, thermal protection enhancer, asphalt stabilizer, emulsifying agent, additive. fiber reinforcer, crosslinking agent, cardboard binder, anti-corrosion additive, wear-resistant additive, anti-friction additive, binder, emulsifier or dispersing agent, crosslinking or curing agent, or as a water absorption inhibitor or as a fluidizing agent, as an antibacterial or antifungal surface or as a barrier, to impregnate wood or as an anticorrosive agent.

Brief description of the figures

Figure 1, GPC curve of lignin type A and lignin type C. The lignin type C has a weight average molecular weight (M ^w ) of 1426 g / mol and a polydispersity (PD) of 1.87.

Figure 2, HSQC of lignin type C.

Figure 3, HSQC of lignin type F.

Detailed description of the invention

The present invention presents a composition for use in refinery processes for the production of various fuels.

For a substance to be processed in a refinery, such as an oil refinery or biological oil refinery, the substance must be in the liquid phase. Either the substance is in a liquid phase at a certain temperature (usually below 80 ° C) or the substance dissolves in a liquid. The present invention presents a composition and a method for preparing said composition wherein the composition comprises lignin or lignin derivatives, where the lignin or its derivatives are in liquid phase or dissolved in a liquid and can be processed in a refinery. The present invention facilitates or even facilitates the production of fuel from biomass material. The composition of the present invention is a liquid composition of lignin and a solvent, a liquid carrier and a fatty acid and wherein the solvent is an alcohol, ether, sulfoxide, ketone, aldehyde or ester or a combination thereof.

In the present application, the term "lignin derivative" means lignin derived molecules or polymers. In the present application, "lignin derivative" and "lignin derived molecules or polymers" are used interchangeably. These molecules or polymers can be the result of chemical modification or degradation of the lignin or a source of lignin, for example by treating black or red liquor to precipitate or separate the lignin.

In the present application, the terms "red liquor" and "brown liquor" denote the same liquor.

Biomass and biomass material

Biomass includes, but is not limited to, plant parts, fruits, vegetables, processing residues, wood chips, chaff, grain, grasses, corn, weeds, aquatic plants, hay, paper, paper products, paper, and paper products. recycled, lignocellulosic material, lignin and any biological material that contains cellulose or material of biological origin. Biomass materials and their derivatives often have a general formula C ^x H ^and O ^z where the z / x ratio depends on the origin, part of the plant, and also processes of the biomass material, and where x and y are each> 1 and z > 0. Preferably x is> 2, or more preferably x is> 3, or more preferably x is>6; z is preferably> 1 or> 2. In one embodiment, x is <2o, in another embodiment x is <15, and in yet another embodiment x is <11. In one embodiment, z is <10 and in another embodiment z is <5. The biomass material can comprise other heteroatoms such as S or N.

The following is a non-limiting list of biomass materials: cellulose (C ⁶ H ¹⁰ O ⁵ K glucose (C ⁶ H ¹² O ⁶ ), glycerol (C ³ H ⁸ O ³ ), ethanol (C ² H ⁶ O); fatty acids such as palmitoleic oil (C ¹⁶ H ³² O ² ), oleic acid (C ¹⁸ H ³⁴ O ² ), tall oil or C ¹⁷ H ^31-35 COOH fatty acid; rosin acids such as abeitic acid (C ²⁰ H ³⁰ O ²⁾ lignin or lignin derivatives in the range of C1 to C20, such as (C ¹⁰ H ¹⁰ O ^2), (C ¹⁰ H ¹² O ^3), (C ¹¹ H ¹⁴ O ^4), lignin in black liquor such as (C ¹⁰ H ⁸ O), (C ¹⁰ H ¹⁰ O ² ), (C ¹¹ H ¹² O ³ ) and pyrolysis oil, etc. Fatty acids such as palmitoleic oil (C ¹⁶ H ³² O ² ), oleic acid (C ¹⁸ H ³⁴ O ² ), tall oil or C ¹⁷ H ^31-35 COOH fatty acid; rosin acids such as abeitic acid (C ²⁰ H ³⁰ O ² ); they can also be used as a component in the composition according to the present invention. In one embodiment, the lignin derivatives are in the range between C1 and C20, such as (C ⁹ H ¹⁰ O ² ), (C ¹⁰ H ¹² O ³ ) and C ¹¹ H ¹⁴ O ⁴ ) or lignin in or from liquor black such as (C ⁹ H ⁸ O), (C ¹⁰ H ¹⁰ O ² ) and C ¹¹ H ¹² O ³ ). Examples of lignin units are guaiac, coniferyl alcohol, sinapyl alcohol, ethyl 4-hydroxy-3-methoxy ketone, (4-hydroxy-3-methoxy-phenyl) -propene, vanillin, and phenol.

Black and red liquor contains cellulose, hemicellulose and lignin and derivatives thereof. The composition according to the present invention comprises lignin obtained from black liquor.

In another embodiment, the lignin or lignin derivatives are obtained from the production of ethanol.

Black liquor comprises four main groups of organic substances, about 30-45% by weight of woody material, 25-35% by weight of saccharin acids, about 10% by weight of formic and acetic acid, 3-5% by weight of extracts, about 1% by weight of methanol and many inorganic elements and sulfur. The exact composition of the liquor varies and depends on the cooking conditions in the production process and the raw material. Red liquor comprises the ions from the sulphite process (calcium, sodium, magnesium or ammonia), sulphonated lignin, hemicellulose and low molecular weight resins.

The weight average molecular weight (mass) (M ^w ) of the lignin should not be more than 5,000 g / mol, or even more preferably not more than 2,000 g / mol, or not more than 1,500 g / mol, or more preferably not more than 1,000 g / mol, or not more than 300 g / mol. The lignin or lignin derivative may have a melting point at a temperature of at least 180 ° C, such as 190 ° C or higher, or 200 ° C or higher, or 300 ° C or lower, or 280 ° C or lower, or 270 ° C or lower, or the lignin or lignin derivatives can remain in the liquid phase when dissolved in a solvent according to the present invention, at a temperature of up to 150 ° C, such as 120 ° C or minor, or

100 ° C or lower, or 90 ° C or lower, or 80 ° C or lower, or 70 ° C or lower.

The amount of lignin in the composition is 4% by weight or more, or 5% by weight or more, or 7% by weight or more, or 10% by weight or more, or 12% by weight or more, or 15% by weight or more, or 20% by weight or more, or 25% by weight or more, or 30% by weight or more, or 40% by weight or more, or 50% by weight or more, or 60% by weight or more, or 70% by weight or more, or 75% by weight or more.

In one embodiment, the lignin or lignin derivatives are de-aromatized. For example, lignin de-flavors to at least 40%, or at least 50%, or at least 60%, or at least 70%, or at least 80%, or at least 90%, or at least less than 95%, or at least 99%.

Solvents, liquid vehicles and additives

The composition according to the present invention comprises a solvent or a mixture of solvents. Preferred solvents are C1-C10 alcohols, C1-C10 ethers, C1-C10 ketones, C1-C10 aldehydes, C1-C10 sulfoxides, and C1-C10 esters. Non-limiting examples are methanol, ethanol, propanol, isopropanol, 1,3-propanediol, glycerol, glycol, dipropylene glycol and butyl ether such as tert-butyl methyl ether; Diethyl ether, diglyme, diisopropyl ether, dimethylsulfoxide (DMSO), tosilic acid, dimethoxyethane, diethylene glycol diethyl ether, petroleum ether, polyethylene glycol, 1,4-dioxane, furfural, acetone, 1,3-dioxolane, cyclopentylmethyl ether, 2-methyltetrahydrofuran , aromatic aldehydes (such as furfural) and tetrahydrofuran (THF). Preferred C1-C10 esters are organic esters, aromatic or non-aromatic esters, examples of esters are benzyl benzoate, various acetates such as methyl acetate, ethyl acetate and butyl acetate, various lactates such as ethyl lactates. Other suitable solvents are dimethylformamide, pyridine and N-methyl pyrrolidone, or acids such as C1-C10 carboxylic acids such as formic acid, acetic acid, propanoic acid, butanoic acid, pentanoic acid and hexanoic acid. In one embodiment, the solvent comprises a combination of C1-C10 alcohols, C1-C10 ethers, and C1-C10 esters. In one embodiment, the solvent comprises two alcohols

C1-C10, for example, ethanol and glycerol, and in another embodiment, the solvent comprises propanol and glycerol. In one embodiment, the solvent comprises polyethylene glycol and a C1-C10 alcohol. In one embodiment, the solvent comprises ethanol in combination with at least one of glycerol and polyethylene glycol. In another embodiment, the solvent comprises glycerol in combination with polyethylene glycol. In one embodiment, at least one solvent is a sulfoxide, an alcohol, or an aldehyde. In one embodiment, the solvent comprises a combination of a C1-C10 sulfoxide and a C1-C10 alcohol, or a C1-C10 sulfoxide and a C1-C10 aldehyde, or a C1-C10 alcohol and a C1-C10 aldehyde. In one embodiment, the solvent comprises dimethylsulfoxide, pyridine, THF, 1,4-dioxane, furfural, dipropylene glycol, polyethylene glycol, or 1,3-propanediol, or a combination thereof. When the composition is to be used in a refinery, the amount of solvent is preferably as low as possible, especially if the solvent contains heteroatoms such as oxygen. The amount of solvent is preferably 33% by weight or more, or 40% by weight or more, or 45% by weight or more, but not more than 66% by weight, or 60% by weight or less, or 55% by weight. weight or less, or 50% by weight or less.

The purpose of the liquid carrier is to bring the desired substrate or solution into the reactor without reacting or otherwise affecting the substrate or solution. Therefore, in the present application, a liquid carrier is an inert hydrocarbon with a high boiling point, preferably at least 150 ° C. The composition may comprise a liquid carrier suitable for a hydrotreater or catalytic cracker, preferably a liquid suitable for both hydrotreater and catalytic cracker. Such liquid vehicles include various hydrocarbon oils. The hydrotreater and catalytic cracker are stages in the refinery process, where the sulfur content of the oil is reduced and where the boiling point is high, the high molecular weight hydrocarbons are converted into gasoline, diesel and gases. The content of liquid carrier can be at least 5% by weight, or at least 10% by weight, or at least 20% by weight, or at least 30% by weight, or at least 40% by weight, preferably at least 50 % by weight, or preferably at least 60% by weight.

The composition comprises fatty acid. In another embodiment, the composition comprises a mixture of esterified fatty acid and / or other fatty acid and / or rosin acid and / or resin acid. In one embodiment, the fatty acid is a biomass-derived mixture comprising fatty acid. In one embodiment, the biomass-derived mixture is tall oil. The composition according to the present invention may comprise a mixture of esterified fatty acid, another fatty acid and optionally rosin acid. The amount of fatty acid or any mixture comprising fatty acid in the composition can be 10% by weight or more, 20% by weight or more, 33% by weight or more, 40% by weight or more, or 45% by weight. or more, but not more than 80% by weight, or 60% by weight or less, or 55% by weight or less, or 50% by weight or less. The mixture itself may comprise 10-50% by weight of esterified fatty acid, 10-50% by weight of other fatty acids and 0-50% by weight of rosin acid, where the total amount of each component does not add up to more than 100 % in weigh. In one embodiment, the amount of esterified fatty acid in the mixture is 15% by weight or more, or 25% by weight or more, or 45% by weight or less, or 35% by weight or less. In one embodiment, the amount of another fatty acid in the mixture is 15% by weight or more, or 25% by weight or more, or 45% by weight or less, or 35% by weight or less. In one embodiment, the amount of rosin acid in the mixture is 5% by weight or more, or 15% by weight or more, or 25% by weight or more, or 45% by weight or less, or 35% by weight. or less. The fatty acid can be any C6-C30 saturated or unsaturated fatty acid, preferably C12-C20 such as a C14, C16, C18, C19 or C20 fatty acid. The composition comprises a fatty acid (or a mixture of fatty acids) and a hydrocarbon oil and the weight ratio of the fatty acid to the hydrocarbon oil is 10: 1 to 1: 1 or 1: 1.

The composition according to the present invention can be a single phase system. By keeping the composition in motion continuously or regularly, the composition can remain in one phase for a long time. Since the composition is intended to be used, for example, in a refinery, the composition will be in motion and therefore will be a single phase system. In one embodiment, the composition is a single phase system at 70 ° C, preferably also at 25 ° C, when left for 10 minutes, preferably 30 minutes, preferably 1 hour, preferably when left for 24 hours.

The liquid vehicle is a hydrocarbon oil and the oil should be in the liquid phase below 80 ° C and preferably have boiling points of 160-500 ° C or 177-371 ° C. These hydrocarbon oils include different types of gas oils and also, for example, full-range straight-line middle distillates, hydrotreated middle distillates, cracked light catalytic distillate, straight-line full-range naphtha distillates, full-range hydrodesulfurized distillates, distillates direct range solvent dewaxed, intermediate direct distillates sulfenylated distillates, full range direct distillation clay treated naphtha, full range atmospheric distillates, full range hydrotreated distillates, direct distillates light, direct distillate heavy distillates, distillates (oil sand) intermediate straight run, hydrocracked, full range straight run naphtha (shale oil) (for example, but not restricted to CAS #: 68476-30-2, 68814-87-9 , 74742-46-7, 64741-59-9, 64741 44-2, 64741-42-0, 101316-57-8, 101316-58-9, 91722-55-3, 91995-58-3, 68527-21-9, 128683-26-1, 91995-46-9, 68410-05-9, 68915- 96-8, 128683-27-2, 195459-19-9). Furthermore, the substances can be solvated in lighter hydrocarbon fractions, such as organic solvents, for example, mesitylene, toluene, benzene, petroleum ether, octanes, nonanes, decanes and also isomerized derivatives of these compounds or mixtures thereof ( CAS No: 108-88-3, 108-67-8, 71-43-2, 8032-32-4, 111-65-9, 111-84-2, 124-18-5).

The composition may further comprise at least one additive. The additive can be any suitable additive for the present composition known to a person skilled in the art. In one embodiment, the additive can further improve the dissolution of the lignin. The additive can have the function of dissolving or breaking intermolecular bonds between lignin chains or lignin derivatives. In one embodiment, the additive is a polar compound or a salt. An emulsifier can be added to the composition. The composition may further contain a base or a basic compound such as an amine, ammonia or ammonium hydroxide.

The additive can also affect the chemical structure of the lignin and thus make the lignin more soluble. The additive can also be any viscosity reducer as described in US 4,734,103 or any viscosity reducer known to a person skilled in the art. The additive can be added to obtain a uniform dispersion of oil and water to improve combustion efficiency and stabilize the dispersion according to US2011 / 0203166.

The additive can be added in a catalytic or stoichiometric amount. The amount of additive can be from 0 to 10% by weight, preferably between 0.25 and 5% by weight, or between 0.5 and 2% by weight. The additive can be added during any step of the method, for example, the additive can be added to black or red liquor or residual material from ethanol production, or before or after filtration or ultrafiltration, or before or after filtration. acidification and separation.

Specific compositions

The composition according to claim 1 comprises at least 4% by weight of lignin, a solvent, hydrocarbon oil and a fatty acid wherein the lignin has a weight average molecular weight of no more than 5,000 g / mol, preferably 2,000 g / mol. The solvent comprises an alcohol, ester, sulfoxide, ketone, aldehyde, or an ether. A composition according to the present invention comprises black liquor, ethanol, glycerol and a fatty acid. Another composition comprises lignin, ethanol and glycerol, preferably also a fatty acid. In one embodiment, the lignin has a weight average molecular weight of no more than 1,000 g / mol.

In one embodiment, the composition comprises 7% by weight or more of lignin and at least 30% by weight of liquid carrier.

In one embodiment, the composition comprises at least 7% by weight of lignin having a weight average molecular weight of no more than 2,000 g / mol, wherein the solvent comprises at least one alcohol, aldehyde, or sulfoxide; and a hydrocarbon oil and fatty acid in a weight ratio of 1: 1 to 1: 5.

In one embodiment of the present invention, the composition comprises 1-50% by weight of lignin, 33-66% by weight of solvent and 33-66% by weight of liquid carrier where the total amount of each component does not add up to more than 100 % in weigh. Another composition according to the present invention comprises at least 4% by weight of lignin, a solvent comprising a C1-C10 alcohol or a C1-C10 sulfoxide or a C1-C10 aldehyde in a concentration of 5-30% by weight and 10-50% by weight of a hydrocarbon oil. Another composition according to the present invention comprises at least 4% by weight of lignin, a solvent comprising a C1-C10 alcohol or a C1-C10 sulfoxide or a C1-C10 aldehyde at a concentration of 5-30% by weight and 10-50% by weight of a mixture of a fatty acid and a hydrocarbon oil.

Preparation method

The composition according to the present invention can be prepared by mixing the lignin in a solvent together with a liquid carrier and also fatty acid. When the solvent is a mixture of more than one solvent, the mixture can be prepared before mixing with the lignin, or all the solvents of the solvent mixture and the lignin can be mixed at the same time. The liquid carrier can be added before, during or after the solvent and lignin mixing step. In one embodiment, the oil is added after mixing the lignin and the solvent. Mixing can be done by stirring or shaking or in any other suitable way. Mixing can be done at room temperature, but can be done at a temperature between 50 ° C and 350 ° C, such as 50 ° C or higher, or 100 ° C or higher, or 150 ° C or higher, but not more than 350 ° C, or 250 ° C or less, or 200 ° C or less. In one embodiment, the liquid carrier is added after mixing the solvent and lignin and when the mixture of solvent and lignin has cooled, preferably below 100 ° C or below 80 ° C. In another embodiment, the lignin is added to the liquid carrier, and optionally the fatty acid as well, prior to the addition of the solvent.

The lignin in the composition may have been treated according to the process described in document WO2012 / 121659 The process refers to the reduction or cleavage of a substrate, leading to depolymerization, where said substrate can be, but is not limited to it, primary, secondary or tertiary benzyl or allyl alcohol, benzyl or allyl ether, benzyl or allyl carbonyl and benzyl or allyl ester, or olefins to the corresponding hydrocarbon. The substrate can be lignin or any other compound or polymer comprising said functional group, or black or red liquor. A general method comprises adding a catalyst, a transition metal catalyst, to a reaction flask or vessel. Add a solvent mixture of at least two solvents where one of the solvents is water and a base. The mixture is then heated followed by the addition of a hydrogen donor and the substrate to be reduced. To inhibit dismutation, a base or carbon dioxide must be added to the solvent / catalyst mixture prior to the addition of a hydrogen donor and the substrate. The hydrogen donor can be, for example, formic acid or an alcohol, it can even be hydrogen gas. The reduction is carried out at a temperature of 40-100 ° C. In one embodiment, the amount of base is not stoichiometric relative to the amount of substrate. Lignin can also be treated (depolymerized) according to the method disclosed in PCT / SE2013 / 051045. A general method comprises mixing biomass or lignin, a hydrogen donor, a transition metal catalyst, and at least one solvent. The hydrogen donor is preferably an alcohol and / or formic acid. Then the formed mixture is heated to no more than 200 ° C. The separated lignin obtained from the reduction or cleavage method can be de-aromatized and can then be used as lignin in the composition according to the present invention. In one embodiment, the biomass material obtained from the chemical reduction is further treated with filtration, ultrafiltration, or cross-flow ultrafiltration; or it is treated with acidification and separation, such as the Lignoboost® technique.

In one embodiment, the composition of the present invention may comprise lignin obtained by precipitation and separation of lignin, for example, by acidification and separation, such as filtration. Lignoboost® or any other similar separation technique are examples of such a technique and can be used. The separated lignin can then be used as biomass material in the composition according to the present invention. In another embodiment, the lignin Separated can further be chemically reduced, cleaved or depolymerized using the method described above and in WO2012 / 121659.

Another method or a complementary method to purify or separate specific components in a biomass material is by filtration, ultrafiltration or cross flow ultrafiltration. The lignin can be separated with respect to size by any of these filtration techniques. Lignin can also be separated with respect to size by a depolymerization technique; This separation can be carried out in combination with filtration, ultrafiltration or cross flow ultrafiltration. By using filtration, ultrafiltration or cross-flow ultrafiltration on the black liquor, lignin with molecular weights of 10,000 g / mol or less can be separated, preferably, the separated lignin has a molecular weight of 2,000 g / mol or less, such as 1000 g / mol or less. The separated lignin can then be used in the composition according to the present invention. In one embodiment, the lignin obtained from said filtration can be further chemically cleaved, reduced or depolymerized using the method described above and in WO2012 / 121659.

The lignin can be filtered using any suitable filtering technique to obtain a molecular weight of the biomass material of 100 g / mol or more, for example 300 g / mol or more, or 500 g / mol or more than, but preferably 1200 g / mol or less, or 1000 g / mol or less, or 900 g / mol or less. To obtain the molecular weight, the filtration can be carried out in one or more stages using one or more filters having different cut-offs. In one embodiment, a chemical reduction can be performed using a transition metal catalyst as described above between each filtration step. In one embodiment, chemical reduction or cleavage is performed using a transition metal catalyst after the final filtering step. In another embodiment, chemical reduction or cleavage is performed using a transition metal catalyst prior to the first filtering step. In yet another embodiment, no catalytic reduction treatment is performed.

Another method of obtaining or separating lignin is to use a base as an additive. Some biorefineries that make ethanol from plants often use a base-based pretreatment process to separate the lignin from the cellulosic material that becomes fuel. For example, the plant can be crushed, then mixed with a solution of ammonium hydroxide and heated to release the lignin.

In other words, the lignin used in the composition according to the present invention can be obtained from biomass or biomass material that has been treated with one of the following steps:

a) chemical reduction or cleavage using a transition metal catalyst as described above; b) acidification and separation, for example Lignoboost®;

c) filtration, ultrafiltration or cross flow ultrafiltration; or

d) any combination thereof.

The biomass material is preferably black or red liquor or waste material from ethanol production. In one embodiment, the lignin has been treated with at least one of steps a) -c) above. In one embodiment, the combination comprises steps a) and c), in another embodiment, the combination comprises steps a) and b), and in yet another embodiment, the combination comprises steps b) and c). In a further embodiment,

The biomass / lignin material can be obtained by a combination of a), b) and c) and wherein each step a), b) and c) can be performed more than once. For example, the combination may be in the order c), a) or c) b), a), or b), a), c); or b), c), a); or b), c) a), c); or b), a), c) a), c).

The composition according to the present invention can be used in a refinery process or as a stage prior to a refinery process to prepare fuel such as diesel and gasoline, or diesel and gasoline analogues; or biogasoline or biodiesel; or fuel additives.

The composition according to the present invention can also be used as either an additive or to prepare an additive, for example as a concrete crushing aid, set retarder for cement, cement strengthener, antioxidant, heat protection enhancer, stabilizer in asphalt, emulsifying agent, fiber reinforcing additive, crosslinking agent, cardboard binder, anti-corrosion additive, wear-resistant additive, anti-friction additive, binder, emulsifier or dispersing agent.

The composition can be added to surfaces to obtain dust control, or the composition can be used to prepare batteries.

The composition can be used to improve surface properties or to impregnate wood or as an anti-corrosion agent. The composition can be used to form an antibacterial or antifungal surface or to form a barrier. The composition can also be used to form carbon fiber.

Examples

In some of the following examples the following types of lignin have been used.

lignin type A1: lignin precipitated with acid from black liquor

Lignin type A2: acid precipitated lignin from black liquor dried to 95% by dry weight Lignin type B: filtered and acid precipitated from black liquor

lignin type C: depolymerized lignin, Mw of about 1,500 g / mol

lignin type F: depolymerized and de-flavored lignin

In the following examples, the symbol "<" means that not all of the substrate, eg, lignin, was dissolved.

In the following examples, the term "fatty acid mixture" or "fatty acid liquid" is used interchangeably and denotes a mixture of fatty acids derived from biomass and wherein the mixture contains oleic acids.

Reference Example 77

To a solution of ethyl acetate (1.3543 g) was added lignin type A1 (0.0196 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <1% by weight of lignin type A1.

Reference Example 78

To a solution of ethanol (1.1185 g) was added lignin type A1 (0.0203 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A1.

Reference Example 79

To a solution of acetone (1.0509 g) was added lignin type A1 (0.0202 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A1.

Reference Example 80

To a polyethylene glycol solution (1.3389 g) was added lignin type A1 (0.1967 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 13% by weight of lignin type A1.

Reference Example 81

To a glycerol solution (1.6616 g) was added lignin type A1 (0.0198 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <1% by weight of lignin type A1.

Reference Example 82

To a solution of 2-methyltetrahydrofuran (1.202 g) was added lignin type A1 (0.0204 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A1.

Reference Example 83

To a solution of cyclopentyl methyl ether (1.2125 g) was added lignin type A1 (0.0198 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A1.

Reference Example 84

To a solution of 1,3-propanediol (0.7703 g) was added lignin type A1 (0.1982 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 20% by weight of lignin type A1.

Reference Example 85

To a solution of 1,3-dioxolane (0.1451 g) was added lignin type A1 (0.2045 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 58% by weight of lignin type A1.

Reference Example 86

To a solution of furfural (0.2804 g) was added lignin type A1 (0.2046 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 42% by weight of lignin type A1.

Reference Example 87

To a dipropylene glycol solution (0.4636 g) was added lignin type A1 (0.2009 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 30% by weight of lignin type A1.

Reference Example 88

To a solution of 1,4-dioxane (0.2094 g) was added lignin type A1 (0.1993 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 49% by weight of lignin type A1.

Reference Example 89

To a solution of methanol (1.1244 g) was added lignin type A1 (0.0208 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A1.

Reference Example 90

To a solution of isopropanol (0.979 g) was added lignin type A1 (0.0207 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A1.

Reference Example 91

To a solution of dimethylsulfoxide (0.2904 g) was added lignin type A1 (0.2075 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 42% by weight of lignin type A1.

Reference Example 92

To a tetrahydrofuran solution (0.1482 g) was added lignin type A1 (0.1976 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 57% by weight of lignin type A1.

Reference Example 93

To a solution of pyridine (0.1604 g) was added lignin type A1 (0.2083 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 56% by weight of lignin type A1.

Reference Example 94

To a solution of acetic acid (1.4342 g) was added lignin type A1 (0.0209 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <1% by weight of lignin type A1.

Reference Example 95

To a hexanoic acid solution (1.3893 g) was added lignin type A1 (0.0206 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <1% by weight of lignin type A1.

Reference Example 97

To a solution of ethyl acetate (1.3474 g) was added lignin type A2 (0.0240 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 98

To a solution of acetone (1.0364 g) was added lignin type A2 (0.0267 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <3% by weight of lignin type A2.

Reference Example 99

To a solution of polyethylene glycol (0.7623 g) was added lignin type A2 (0.1162 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 13% by weight of lignin type A2.

Reference Example 100

To a glycerol solution (1.5214 g) was added lignin type A2 (0.0303 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 101

To a solution of 2-methyltetrahydrofuran (1.1851 g) was added lignin type A2 (0.0224 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 102

To a solution of cyclopentyl methyl ether (1.2764 g) was added lignin type A2 (0.0259 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 103

To a solution of 1,3-propanediol (0.4012 g) was added lignin type A2 (0.1014 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 20% by weight of lignin type A2.

Reference Example 104

To a solution of 1,3-dioxolane (0.1334 g) was added lignin type A2 (0.1161 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 47% by weight of lignin type A2.

Reference Example 105

To a solution of furfural (0.1389 g) was added lignin type A2 (0.1021 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 42% by weight of lignin type A2.

Reference Example 106

To a dipropylene glycol solution (0.3033 g) was added lignin type A2 (0.1081 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 26% by weight of lignin type A2.

Reference Example 107

To a solution of 1,4-dioxane (0.2017 g) was added lignin type A2 (0.1052 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 34% by weight of lignin type A2.

Reference Example 108

To a solution of methanol (1.0575 g) was added lignin type A2 (0.0239 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 109

To a solution of isopropanol (0.9578 g) was added lignin type A2 (0.0316 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <3% by weight of lignin type A2.

Reference Example 110

To a solution of dimethylsulfoxide (0.2170 g) was added lignin type A2 (0.1110 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 34% by weight of lignin type A2.

Reference Example 111

To a tetrahydrofuran solution (0.0968 g) was added lignin type A2 (0.1005 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising 51% by weight of lignin type A2.

Reference Example 112

To a pyridine solution (0.1723 g) was added lignin type A2 (0.1062 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution comprising 38% by weight of lignin type A2 was obtained.

Reference Example 113

To a solution of acetic acid (1.4939 g) was added lignin type A2 (0.0268 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 114

To a solution of benzonitrile (1.3149 g) was added lignin type A2 (0.0272 g) in one portion or stepwise. The suspension was stirred with heating. After cooling, a solution was obtained comprising <2% by weight of lignin type A2.

Reference Example 132

To a mixture comprising 1,3-propanediol (0.4058 g) and citric acid (0.1330 g), lignin type A2 (0.2036 g) was added in one portion or stepwise. The suspension was stirred with heating. A pourable solution was obtained at 70 ° C comprising 27% by weight of lignin type A2.

Reference Example 133

To a mixture comprising 1,3-propanediol (0.4211 g) and TWEEN-20 (0.2933 g) (a polysorbate surfactant), lignin type 2 (0.2101 g) was added in one portion or in stages. The suspension was stirred with heating. A pourable solution was obtained at 70 ° C comprising 23% by weight of lignin type A2.

Reference Example 134

To a mixture comprising 1,3-propanediol (0.4045 g) and 3- (N, N-dimethyl octadecylammonium) propanesulfone) (0.0660 g), lignin type A2 (0.2018 g) was added in a portion or in stages. The suspension was stirred with heating. A pourable solution was obtained at 70 ° C comprising 30% by weight of lignin type A2.

Reference Example 135

To a mixture comprising 1,3-propanediol (0.4130 g) and pyridine (0.0643 g), lignin type A2 (0.2013 g) was added in one portion or stepwise. The suspension was stirred with heating. A pourable solution was obtained at 70 ° C comprising 30% by weight of lignin type A2.

Reference Example 136

To a mixture comprising 1,3-propanediol (0.4130 g) and triethylamine (0.1266 g), lignin type A2 (0.2010 g) was added in one portion or stepwise. The suspension was stirred with heating. A pourable solution was obtained at 70 ° C comprising 27% by weight of lignin type A2.

Reference Example 137

To a mixture comprising 1,3-propanediol (0.4510 g) and Nonidet P (0.3111 g), lignin type A2 (0.2084 g) was added in one portion or stepwise. The suspension was stirred with heating. A pourable solution was obtained at 70 ° C comprising 21% by weight of lignin type A2.

Reference Example 141

To a solution of a mixture comprising biomass-derived fatty acid (0.1074) and A1 type lignin (0.1003 g) was added polyethylene glycol (1.5078 g) in one portion or stepwise until the lignin dissolved. . The suspension was stirred with heating. After cooling, a solution was obtained comprising 6% by weight of lignin type A1. Reference Example 142

To a solution of a mixture comprising biomass-derived fatty acid (0.0994) and lignin type A1 (0.1043 g) was added 1,3-propanediol (0.4308 g) in one portion or stepwise until lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 16% by weight of lignin type A1.

Reference Example 143

To a solution of a mixture comprising fatty acid (0.1045 g) derived from biomass and lignin type A1 (0.1025 g) was added 1,3-dioxolane (0.7963 g) in one portion or stepwise until that the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 10% by weight of lignin type A1.

All of the following Reference Examples were performed in the same manner unless otherwise indicated, ie, the solvent (s) were added until the lignin dissolved.

Reference Example 144

To a solution of furfural (0.3969 g) and a mixture comprising fatty acid (0.1076 g) derived from biomass, A1 type lignin (0.1040 g) was added in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 17% by weight of lignin type A1.

Reference Example 145

To a solution of 1,4-dioxane (0.9763 g) and a mixture comprising fatty acid (0.0963 g) derived from biomass, lignin type A1 (0.1047 g) was added in one portion or stepwise. . The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 9% by weight of lignin type A1.

Reference Example 146

To a solution of dimethylsulfoxide (0.2718 g) and a mixture comprising fatty acid (0.1164 g) derived from biomass, lignin type A1 (0.1001 g) was added in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a biphasic solution was obtained comprising 21% by weight of lignin type A1.

Reference Example 147

To a solution of pyridine (0.3529 g) and a mixture comprising fatty acid (0.1074 g) derived from biomass, A1 type lignin (0.0953 g) was added in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 17% by weight of lignin type A1.

Reference Example 148

To a polyethylene glycol solution (0.5676 g) was added lignin type A1 (0.1023 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 15% by weight of lignin type A1.

Reference Example 149

To a solution of 1,3-propanediol (0.6385 g) was added lignin type A1 (0.1021 g) in one portion or stepwise. I know added the solvent until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 14% by weight of lignin type A1.

Reference Example 150

To a solution of 1,3-dioxolane (0.2125 g) was added lignin type A1 (0.1031 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 33% by weight of lignin type A1.

Reference Example 151

To a solution of furfural (0.3224 g) was added lignin type A1 (0.1000 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 24% by weight of lignin type A1.

Reference Example 152

To a dipropylene glycol solution (0.3551 g) was added lignin type A1 (0.0989) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 22% by weight of lignin type A1.

Reference Example 153

To a solution of 1,4-dioxane (0.1558 g) was added lignin type A1 (0.1014 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 39% by weight of lignin type A1.

Reference Example 154

To a solution of dimethylsulfoxide (0.3627 g) was added lignin type A1 (0.0983 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 21% by weight of lignin type A1.

Reference Example 155

To a tetrahydrofuran solution (0.1417 g) was added lignin type A1 (0.0978 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 41% by weight of lignin type A1.

Reference Example 156

To a solution of pyridine (0.1364 g) was added lignin type A1 (0.1005 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 42% by weight of lignin type A1.

Reference Example 157

To a solution of polyethylene glycol (0.2891 g) was added lignin type A1 (0.0205 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 7% by weight of lignin type A1.

Reference Example 158

To a solution of 1,3-propanediol (0.2026 g) was added lignin type A1 (0.0207 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 9% by weight of lignin type A1.

Reference Example 159

To a solution of 1,3-dioxolane (0.0876 g) was added lignin type A1 (0.0203 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 19% by weight of lignin type A1.

Reference Example 160

To a solution of furfural (0.1255 g) was added lignin type A1 (0.0208 g) in one portion or stepwise. Added the solvent until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 14% by weight of lignin type A1.

Reference Example 161

To a dipropylene glycol solution (0.3157 g) was added lignin type A1 (0.0195 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 6% by weight of lignin type A1.

Reference Example 162

To a solution of 1,4-dioxane (0.1712 g) was added lignin type A1 (0.0207 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 11% by weight of lignin type A1.

Reference Example 163

To a solution of dimethylsulfoxide (0.2532 g) was added lignin type A1 (0.0204 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 7% by weight of lignin type A1.

Reference Example 164

To a tetrahydrofuran solution (0.0739 g) was added lignin type A1 (0.0201 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 21% by weight of lignin type A1.

Reference Example 165

To a solution of pyridine (0.1179 g) was added lignin type A1 (0.0201 g) in one portion or stepwise. The solvent was added until the lignin dissolved. The suspension was stirred with heating. After cooling, a solution was obtained comprising 15% by weight of lignin type A1.

Reference Example 166

To a solution of a mixture comprising biomass-derived fatty acids (0.1946 g) and lignin type A2 (0.2098 g) was added furfural (0.4078 g) in one portion or stepwise until the mixture was dissolved. lignin. The suspension was stirred with heating (80 ° C). After cooling, a solution was obtained comprising 26% by weight of lignin type A2.

Reference Example 167

To a solution of a mixture comprising fatty acids (0.2105 g) derived from biomass and type B lignin (0.2100 g) was added furfural (0.2918 g) in one portion or stepwise until the mixture was dissolved. lignin. The suspension was stirred with heating (80 ° C). After cooling, a solution was obtained comprising 29% by weight of lignin type B.

Reference Example 168

To a solution of a mixture comprising fatty acids (0.2089 g) derived from biomass and lignin type B (0.2196 g) was added furfural (0.4016 g) in one portion or stepwise until the mixture was dissolved. lignin. The suspension was stirred with heating (80 ° C). After cooling, a solution was obtained comprising 26% by weight of lignin type B.

Reference Example 169

Oleic acid (1.3499 g) was added to lignin type A2 (0.0101 g) in one portion. The mixture was stirred with heating (70 degrees). A 70 degree solution was obtained comprising <0.7% by weight of lignin type A2.

Reference Example 170

To a solution of isophorone (0.1660 g) was added lignin type A2 (0.1341 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 45% by weight of lignin type A2.

Reference Example 171

To a solution of mesityl oxide (0.1119 g) was added lignin type A2 (0.1087 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 49% by weight of lignin type A2.

Reference Example 172

To a solution of ethyl acetate (0.0366 g) was added lignin type C (0.0992 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 73% by weight of lignin type C.

Reference Example 173

To a solution of ethanol (0.0289 g) type C lignin (0.1004 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 78% by weight of lignin type C.

Reference Example 174

To a petroleum ether solution (0.9516 g) was added type C lignin (0.0985 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A solution was obtained comprising <9% by weight of lignin type C.

Reference Example 175

To a solution of acetone (0.0396 g) was added lignin type C (0.1086 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 73% by weight of lignin type C.

Reference Example 176

To a polyethylene glycol solution (0.1142 g) type C lignin (0.0985 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 46% by weight of lignin type C.

Reference Example 177

To a glycerol solution (1.1062 g) type C lignin (0.1008 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A solution was obtained comprising <8% by weight of lignin type C.

Reference Example 178

To a solution of 2-methyltetrahydrofuran (0.0554 g) was added lignin type C (0.1003 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 64% by weight of lignin type C.

Reference Example 179

To a solution of cyclopentyl methyl ether (0.0329 g) type C lignin (0.0988 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 75% by weight of lignin type C.

Reference Example 180

To a solution of 1,3-propanediol (0.0799 g) was added lignin type C (0.0895 g) in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 53% by weight of lignin type C.

Reference Example 181

To a solution of 1,3-dioxolane (0.0527 g) type C lignin (0.0912 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 63% by weight of lignin type C.

Reference Example 182

To a solution of furfural (0.0601 g) type C lignin (0.1010 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 63% by weight of lignin type C.

Reference Example 183

To a dipropylene glycol solution (0.0497 g) type C lignin (0.0919 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 65% by weight of lignin type C.

Reference Example 184

To a solution of 1,4-dioxane (0.0378 g) type C lignin (0.0977 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 72% by weight of lignin type C.

Reference Example 185

To a methanol solution (0.0286 g) type C lignin (0.0951 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 77% by weight of lignin type C.

Reference Example 186

To a solution of isopropanol (0.0484 g) type C lignin (0.0903 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 65% by weight of lignin type C.

Reference Example 187

To a solution of dimethylsulfoxide (0.0645 g) type C lignin (0.0921 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 59% by weight of lignin type C.

Reference Example 188

To a tetrahydrofuran solution (0.0556 g) type C lignin (0.0980 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 64% by weight of lignin type C.

Reference Example 189

To a pyridine solution (0.0562 g) type C lignin (0.1011 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 64% by weight of lignin type C.

Reference Example 190

To a solution of acetic acid (0.0322 g) type C lignin (0.1006 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 75% by weight of lignin type C.

Reference Example 191

To a hexanoic acid solution (1.0702 g) type C lignin (0.0915 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A solution was obtained comprising <8% by weight of lignin type C.

Reference Example 192

To a solution of isophorone (0.0565 g) type C lignin (0.0951 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 63% by weight of lignin type C.

Reference Example 193

To a mesityl oxide solution (0.0405 g) type C lignin (0.1002 g) was added in one portion or stepwise. The suspension was stirred with heating (70 ° C). A pourable solution was obtained at 70 ° C comprising 71% by weight of lignin type C.

Example 194

To a solution of a mixture with a 1: 1 weight ratio of diesel and a liquid comprising fatty acid (0.1214 g, total weight of diesel and fatty acid) and lignin type A2 (0.0242 g) was added polyethylene glycol (0.2348 g) in one portion or stepwise until the lignin is dissolved. The suspension was stirred with heating (70 ° C). After cooling, a solution was obtained comprising 6% by weight of lignin type A2.

Example 195

To a solution of a mixture with a 1: 1 weight ratio of diesel and a liquid comprising fatty acid (0.1300 g, total weight of diesel and fatty acid) and lignin type A2 (0.0255 g) was added 1,3-propanediol (0.1411 g) in one portion or stepwise until the lignin dissolved. The suspension was stirred with heating (70 ° C). After cooling, a solution was obtained comprising 9% by weight of lignin type A2.

Example 196

To a solution of a mixture with a 1: 1 weight ratio of diesel and a liquid comprising fatty acid (0.1241 g, total weight of diesel and fatty acid) and lignin type A2 (0.0249 g) was added furfural (0.1384 g) in one portion or stepwise until the lignin is dissolved. The suspension was stirred with heating (70 ° C). After cooling, a solution was obtained comprising 9% by weight of lignin type A2.

Example 197

To a solution of a mixture with a 1: 1 weight ratio of diesel and a liquid comprising fatty acid (0.1314 g, total weight of diesel and fatty acid) and lignin type A2 (0.0201 g) was added Dipropylene glycol (0.4044 g) in one portion or stepwise until the lignin is dissolved. The suspension was stirred with heating (70 ° C). After cooling, a solution was obtained comprising 4% by weight of lignin type A2.

Example 198

To a solution of a mixture with a 1: 1 weight ratio of diesel and a liquid comprising fatty acid (0.1270 g, total weight of diesel and fatty acid) and lignin type A2 (0.0217 g) was added dimethylsulfoxide (0.0722 g) in one portion or stepwise until the lignin is dissolved. The suspension was stirred with heating (70 ° C). After cooling, a solution was obtained comprising 10% by weight of lignin type A2.

Reference Example 199

A solution of furfural and 1,3-propanediol in a mixture with a 1: 1 weight ratio (0.2795 g) was added to the lignin type A2 (0.1197 g) until a pourable solution was obtained at 70 ° C. A pourable solution was obtained at 70 ° C comprising 30% by weight of lignin type A2.

Reference Example 200

To the lignin type A2 (0.1190 g) was added a solution of dimethylsulfoxide and 1,4-dioxane in a mixture with a 1: 1 weight ratio (0.1345 g) until a pourable solution was obtained at 70 ° C. A pourable solution was obtained at 70 ° C comprising 47% by weight of lignin type A2.

Reference Example 201

To the lignin type A2 (0.1263 g) was added a solution of dimethylsulfoxide and 1,3-propanediol in a mixture with a 1: 1 weight ratio (0.2437 g) until a pourable solution was obtained at 70 ° C. A pourable solution was obtained at 70 ° C comprising 34% by weight of lignin type A2.

Reference Example 202

To lignin type A2 (0.1124 g) was added a solution of dimethylsulfoxide and pyridine in a mixture with a 1: 1 weight ratio (0.1783 g of total weight of DMSO and pyridine) until a solution was obtained. Pourable at 70 ° C. A pourable solution was obtained at 70 ° C comprising 39% by weight of lignin type A2.

Reference Example 203

To the lignin type A2 (0.1046 g) a solution of methanol (1.0686 g) was added and stirred at 70 ° C. A solution comprising <9 % by weight of lignin type A2.

Reference Example 204

To the lignin type A2 (0.1275 g) a solution of 7N ammonia in methanol (0.2669 g) was added and stirred at 70 ° C. A solution was obtained comprising <32% by weight of lignin type A2.

Example 205

Preparation of lignin type C using two different nickel catalysts

5.0 g of lignin type A2 was dissolved in 70 ml of isopropanol, 5.3 g of wet Raney 4200 nickel was added and the reaction was heated at 160 ° C for 18 hours in a 100 ml closed steel autoclave. After cooling, the dissolved lignin was transferred to a round bottom flask and the isopropanol was evaporated. 2.61 g of product were collected, 52% yield.

5.0 g of lignin type A2 was dissolved in 70 ml of isopropanol, 5.3 g of wet Raney 2800 nickel was added and the reaction was heated at 160 ° C for 18 hours in a 100 ml closed steel autoclave. After cooling, the dissolved lignin was transferred to a round bottom flask and the isopropanol was evaporated. 3.00 g of product were collected, 60% yield.

Example 206

To a suspension of lignin type C (0.0240 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1309 g), ethyl acetate (1, 1303 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Example 207

To a suspension of lignin type C (0.0268 g) in a mixture with a 1: 1 weight ratio of light diesel and a liquid comprising fatty acid (0.1223 g), ethanol (0.9791 g ) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Example 208

To a suspension of lignin type C (0.0284 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1176 g), acetone (0.6696 g ) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <3% by weight of lignin type C.

Example 209

To a suspension of lignin type C (0.0248 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1298 g), polyethylene glycol (0.0901 g ) and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 10% by weight of lignin type C.

Example 210

To a suspension of lignin type C (0.0220 g) in a mixture with a 1: 1 weight ratio of light diesel and a liquid comprising fatty acid (0.1214 g), glycerol (0.6450 g ) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <3% by weight of lignin type C.

Example 211

To a suspension of lignin type C (0.0293 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1334 g), 2-methyltetrahydrofuran (0.9027 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <3% by weight of lignin type C.

Example 212

To a suspension of lignin type C (0.0232 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1340 g), cyclopentyl methyl ether (0.8313 g ) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Example 213

To a suspension of lignin type C (0.0224 g) in a mixture with a 1: 1 weight ratio of light diesel and a liquid comprising fatty acid (0.1291 g), 1,3-propanediol (0.0286 g) was added and stirred at 70 ° C. It was obtained

a biphasic solution at 70 ° C comprising 12% by weight of lignin type C.

Example 214

en una mezcla con una relación en peso 1:1 de gasóleo ligero y líquido que comprendía ácido graso (0,1386 g), Se añadió 1,3-dioxolano (0,3543 g) y se agitó a 70 °C. Se obtuvo solución a 25 °C que comprendía 4 % en peso de lignina tipo C.To a suspension of lignin type C (0.0211 g

In a 1: 1 weight ratio mixture of light and liquid gas oil comprising fatty acid (0.1386 g), 1,3-dioxolane (0.3543 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 4% by weight of lignin type C.

Example 215

To a suspension of lignin type C (0.0254 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1376 g), furfural (0.0676 g) was added and stirred at 70 ° C. A

biphasic solution at 70 ° C comprising 11% by weight of lignin type C.

Example 216

en una mezcla con una relación en peso 1:1 de gasóleo ligero y líquido que comprendía ácido graso (0,1399 g), se le añadió dipropilenglicol (0,2048 g) y se agitó a 70 °C. Se obtuv una solución a 25 °C que comprendía 6 % en peso de lignina tipo C.To a suspension of lignin type C (0.0227 g

In a 1: 1 weight ratio mixture of light and liquid gas oil comprising fatty acid (0.1399 g), dipropylene glycol (0.2048 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 6% by weight of lignin type C.

Example 217

To a suspension of lignin type C (0.0272 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1413 g), 1,4-dioxane (0.3958 g) was added and stirred at 70 ° C. A

solution at 25 ° C comprising 5% by weight of lignin type C.

Example 218

To a suspension of lignin type C (0.0243 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1408 g), methanol (0.8046 g) was added and stirred at 70 ° C. A

solution at 25 ° C comprising 3% by weight of lignin type C.

Example 219

To a suspension of lignin type C (0.0239 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1208 g), isopropanol (0.6760 g) was added and stirred at 70 ° C. A

solution at 70 ° C comprising <3% by weight of lignin type C.

Example 220

To a suspension of lignin type C (0.0244 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1289 g), dimethylsulfoxide (0.0682 g) was added and stirred at 70 ° C. It was obtained

a biphasic solution at 70 ° C comprising 11% by weight of lignin type C.

Example 221

To a suspension of type C lignin (0.0203 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1300 g), tetrahydrofuran (0.4983 g) was added and stirred at 70 ° C. It was obtained

a solution at 25 ° C comprising 3% by weight of lignin type C.

Example 222

To a suspension of type C lignin (0.0246 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1233 g), pyridine (0.1727 g) was added and stirred at 70 ° C. A

biphasic solution at 70 ° C comprising 8% by weight of lignin type C.

Example 223

To a suspension of lignin type C (0.0270 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1213 g), acetic acid (1.4428 g) was added and stirred at 70 ° C. It was obtained

a 70 ° C solution comprising <2% by weight type C lignin.

Example 224

To a suspension of lignin type C (0.0213 g) in a mixture with a 1: 1 weight ratio of light diesel and a

liquid comprising fatty acid (0.1185 g), hexanoic acid (1.0270 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Example 225

To a suspension of type C lignin (0.0223 g) in a mixture with a 1: 1 weight ratio of light diesel and a liquid comprising fatty acid (0.1186 g), isophorone (0.4511 g) was added ) and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 4% by weight of lignin type C.

Example 226

To a suspension of type C lignin (0.0273 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1267 g), mesityl oxide (0.1267 g) was added. 4408 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Example 227

To a suspension of lignin type C (0.0215 g) in light gas oil (0.1248 g), ethyl acetate (1.3574 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <1% by weight of lignin type C.

Reference Example 228

To a suspension of lignin type C (0.0259 g) in light gas oil (0.1241 g), ethanol (1.0178 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Reference Example 229

To a suspension of lignin type C (0.0259 g) in light gas oil (0.1256 g), acetone (0.7940 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <3% by weight of lignin type C.

Reference Example 230

To a suspension of lignin type C (0.0224 g) in light gas oil (0.1220 g), polyethylene glycol (0.0384 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 12% by weight of lignin type C.

Reference Example 231

To a suspension of lignin type C (0.0240 g) in light gas oil (0.1240 g), glycerol (0.6579 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <3% by weight of lignin type C.

Reference Example 232

To a suspension of lignin type C (0.0249 g) in light gas oil (0.1350 g), 2-methyltetrahydrofuran (0.9880 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C. Reference Example 233

To a suspension of lignin type C (0.0250 g) in light gas oil (0.1305 g), cyclopentyl methyl ether (0.9308 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Reference Example 234

To a suspension of lignin type C (0.0243 g) in light gas oil (0.1273 g), 1,3-propanediol (0.0274 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 14% by weight of lignin type C.

Reference Example 235

To a suspension of lignin type C (0.0218 g) in light gas oil (0.1316 g), 1,3-dioxolane (0.4085 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 4% by weight of lignin type C.

Reference Example 236

To a suspension of lignin type C (0.0236 g) in light gas oil (0.1262 g), furfural (0.0408 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 12% by weight of lignin type C.

Reference Example 237

To a suspension of lignin type C (0.0268 g) in light gas oil (0.1241 g), dipropylene glycol (0.0564 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 13% by weight of lignin type C.

Reference Example 238

To a suspension of lignin type C (0.0236 g) in light gas oil (0.1262 g), 1,4-dioxane (0.4513 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 4% by weight of lignin type C.

Reference Example 239

To a suspension of lignin type C (0.0216 g) in light gas oil (0.1198 g), methanol (0.0235 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 13% by weight of lignin type C.

Reference Example 240

To a suspension of lignin type C (0.0203 g) in light gas oil (0.1340 g), isopropanol (0.7374 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Reference Example 241

To a suspension of lignin type C (0.0283 g) in light gas oil (0.1269 g), dimethylsulfoxide (0.0481 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 14% by weight of lignin type C.

Reference Example 242

To a suspension of lignin type C (0.0258 g) in light gas oil (0.1256 g), tetrahydrofuran (0.9601 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 2% by weight of lignin type C.

Reference Example 243

To a suspension of lignin type C (0.0259 g) in light gas oil (0.1250 g), pyridine (0.0775 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 11% by weight of lignin type C.

Reference Example 244

To a suspension of lignin type C (0.0261 g) in light gas oil (0.1271 g), acetic acid (0.0784 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 11% by weight of lignin type C.

Reference Example 245

To a suspension of lignin type C (0.0260 g) in light gas oil (0.1197 g), hexanoic acid (1.0185 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Reference Example 246

To a suspension of lignin type C (0.0242 g) in light gas oil (0.1307 g), isophorone (0.4408 g) was added and stirred at 70 ° C. A solution was obtained at 25 ° C comprising 4% by weight of lignin type C.

Reference Example 247

To a suspension of lignin type C (0.0236 g) in light gas oil (0.1207 g), mesityl oxide (0.9485 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <2% by weight of lignin type C.

Example 248

To a suspension of lignin type A2 (0.0258 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1182 g), a mixture with a 1: 1 weight ratio 1 of furfural and 1,3-propanediol (0.1316 g) and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 9% by weight of lignin type A2.

Example 249

To a suspension of lignin type A2 (0.0306 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1172 g), a mixture with a 1: 1 weight ratio 1 of dimethylsulfoxide and 1,4-dioxane (0.1272 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 11% by weight of standard lignin A2. When a further mixture with a 1: 1 weight ratio of dimethylsulfoxide and 1,4-dioxane (0.4052 g) was added, a solution was obtained at 25 ° C comprising 4% by weight.

Example 250

To a suspension of lignin type A2 (0.0326 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1216 g), a mixture with a ratio of 0.1216 g was added. 1: 1 weight of dimethylsulfoxide and 1,3-propanediol (0.1068 g) and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 12% by weight of lignin type A2. When a further mixture with a 1: 1 weight ratio of dimethylsulfoxide and 1,3-propanediol (0.1929 g) was added, a solution was obtained at 25 ° C comprising 7% by weight.

Example 251

To a suspension of lignin type A2 (0.0403 g) in a mixture with a 1: 1 weight ratio of light diesel fuel and a liquid comprising fatty acid (0.1168 g), a mixture with a ratio of 0.1168 g was added. 1: 1 weight of dimethylsulfoxide and pyridine (0.1192 g) and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 15% by weight of lignin type A2. When a further mixture with a 1: 1 weight ratio of dimethylsulfoxide and pyridine (0.1553 g) was added, a solution was obtained at 25 ° C comprising 10% by weight.

Example 252

To a suspension of lignin type A2 (0.0219 g) in a mixture with a 1: 1 weight ratio of light diesel and a liquid comprising fatty acid (0.1101 g), a mixture with a ratio of 0.1101 g was added. 1: 1 weight of furfural and 1,3-dioxolane (0.3912 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <4% by weight of lignin type A2.

Example 253

To a suspension of lignin type A2 (0.0228 g) in a mixture with a 1: 1 weight ratio of light diesel and a liquid comprising fatty acid (0.1380 g), a mixture with a ratio of 0.1380 g was added. 1: 1 weight of polyethylene glycol and tetrahydrofuran (0.1188 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 8% by weight of lignin type A2.

Example 254

To a suspension of lignin type A2 (0.0229 g) in a mixture with a 1: 1 weight ratio of light gas oil and a liquid comprising fatty acid (0.1214 g), a mixture with a ratio of 0.1214 g was added. 1: 1 weight of pyridine and isophorone (0.4489 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising <4% by weight of lignin type A2.

Reference Example 255

To a suspension of F-type lignin (0.100 g) in light gas oil (0.1943 g), 1,3-dioxolane (0.1350 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 23% by weight of lignin type F. When additional 1,3-dioxolane (0.1206 g) was added, a more homogeneous solution was obtained at 70 ° C comprising 18 % in weigh.

Reference Example 256

Dipropylene glycol (0.0804 g) was added to a suspension of lignin type F (0.100 g) in light gas oil (0.1919 g) and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 27% by weight of lignin type F. When additional dipropylene glycol (0.2702 g) was added a more homogeneous solution was obtained at 70 ° C comprising 16% by weight.

Reference Example 257

To a suspension of lignin type F (0.100 g) in light gas oil (0.1462 g), 1,4-dioxane (0.0704 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 32% by weight of lignin type F.

Reference Example 258

To a suspension of F-type lignin (0.100 g) in light gas oil (0.1553 g), methanol (0.0237 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 36% by weight of lignin type F.

Reference Example 259

To a suspension of F-type lignin (0.100 g) in light gas oil (0.1531 g), tetrahydrofuran (0.0425 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 34% by weight of lignin type F.

Reference Example 260

To a suspension of lignin type F (0.100 g) in light gas oil (0.1561 g), isophorone (0.0791 g) was added and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 30% by weight of lignin type F.

Example 261

To a suspension of lignin type A2 (0.0998 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1123 g), a mixture with a 1: 1 weight ratio of furfural and 1,3-propanediol (0.2197 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 23% by weight of lignin type A2.

Example 262

To a suspension of lignin type A2 (0.0986 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1188 g), a mixture with a 1: 1 weight ratio of dimethylsulfoxide and 1,4-dioxane (0.2199 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 23% by weight of lignin type A2.

Example 263

To a suspension of lignin type A2 (0.1014 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1224 g), a mixture with a 1: 1 weight ratio of dimethylsulfoxide and 1,3-propanediol (0.1404 g) and stirred at 70 ° C. A biphasic solution was obtained at 70 ° C comprising 28% by weight of lignin type A2. When a further mixture with a 1: 1 weight ratio of dimethylsulfoxide and 1,3-propanediol (0.1241 g) was added, a solution was obtained at 70 ° C comprising 21% by weight.

Example 264

To a suspension of lignin type A2 (0.1020 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1227 g), a mixture with a 1: 1 weight ratio of dimethylsulfoxide and pyridine (0.2128 g). and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 23% by weight of lignin type A2.

Example 265

To a suspension of lignin type A2 (0.1023 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1135 g), a mixture with a 1: 1 weight ratio of polyethylene glycol and tetrahydrofuran (0.3085 g) and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 20% by weight of lignin type A2.

Example 266

To a suspension of lignin type A2 (0.0961 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1288 g), polyethylene glycol (0.3054 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 18% by weight of lignin type A2.

Example 267

To a suspension of lignin type A2 (0.0981 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1257 g), 1,3-propanediol (0.1608 g) was added. and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 26% by weight of lignin type A2.

Example 268

To a suspension of lignin type A2 (0.1035 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1263 g), furfural (0.1921 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 25% by weight of lignin type A2.

Example 269

To a suspension of lignin type A2 (0.1047 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1292 g), dipropylene glycol (0.5455 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 13% by weight of lignin type A2.

Example 270

To a suspension of lignin type A2 (0.1022 g) in a 3: 7 mixture of light gas oil and a liquid comprising fatty acid (0.1182 g), dimethylsulfoxide (0.1992 g) was added and stirred at 70 ° C. A solution was obtained at 70 ° C comprising 24% by weight of lignin type A2.

Example 271

Preparation of type F lignin using nickel catalysts

1.0 g of lignin type B was dissolved in 70 ml of isopropanol, 3.3 g of wet Raney 2800 nickel was added and the reaction was heated at 160 ° C for 18 hours in a 100 ml closed steel autoclave. After cooling, the dissolved lignin was transferred to a round bottom flask and the isopropanol was evaporated. 0.64 g of product was collected, 64% yield.

Claims (13)

1. A composition comprising lignin, a solvent, and a liquid carrier; where the lignin is obtained from black liquor and constitutes at least 4% by weight of the composition and wherein the lignin has a weight average molecular weight of no more than 5,000 g / mol, and wherein the solvent is an organic alcohol, ether or ester, sulfoxide, ketone, aldehyde, or a combination thereof; Y wherein the liquid vehicle is a hydrocarbon oil; and wherein the composition further comprises a fatty acid and wherein the weight ratio of the fatty acid to the hydrocarbon oil is from 10: 1 to 1: 1. 2. The composition according to claim 1, wherein the composition further comprises esterified fatty acid. The composition according to claim 2, wherein the composition comprises 7% by weight of lignin or more, or 10% by weight or more, or 12% by weight or more, or 15% by weight or more, or 20% by weight or more, or 25% by weight or more, or 30% by weight or more. The composition according to any one of claims 1-3, wherein the content of liquid carrier is at least 20% by weight, or at least 30% by weight, or at least 40% by weight, preferably at least 50% by weight, or preferably at least 60% by weight. The composition according to any one of claims 1 to 4, wherein the composition comprises 7% by weight or more of lignin and at least 30% by weight of liquid carrier and wherein the solvent is preferably a sulfoxide, a alcohol or an aldehyde. The composition according to any one of claims 1 to 5, wherein the solvent comprises dimethylsulfoxide, THF, 1,4-dioxane, furfural, dipropylene glycol, polyethylene glycol or 1,3-propanediol, or a combination thereof. 7. A method for producing the composition according to any one of claims 1 to 6, comprising: - providing lignin obtained from black liquor and having a weight average molecular weight of not more than 5,000 g / mol; - providing a solvent that is an alcohol, ether, sulfoxide, ketone, aldehyde or ester or a combination thereof, a liquid carrier and a fatty acid; Y - adding lignin to the solvent, the liquid vehicle and the fatty acid to obtain a concentration of at least 4% by weight and mixing; wherein the liquid carrier is a hydrocarbon oil and wherein the weight ratio of the fatty acid to the hydrocarbon oil is 10: 1 to 1: 1. 8. The method of claim 7, wherein the composition is heated during mixing to a temperature between 50 and 350 ° C. The method according to any one of claims 7 or 8, wherein the lignin is derived from black liquor and, optionally, wherein the lignin is obtained from: - chemical reduction using a transition metal catalyst; - acidification and separation; - filtration, ultrafiltration or cross flow ultrafiltration; or - any combination of the same, of the black liquor. 10. Use of the composition according to any one of claims 1 to 6 for preparing fuels such as gasoline and diesel, or diesel and gasoline analogues, or biogasoline or biodiesel; or fuel additives. 11. A fuel obtained from the composition according to any one of claims 1 to 6. 12. Use of the composition according to any one of claims 1 to 6 as a concrete crushing aid, setting retarder for cement, cement strengthener, antioxidant, thermal protection enhancer, asphalt stabilizer, emulsifying agent, additive fiber reinforcer, crosslinking agent, cardboard binder, anti-corrosion additive, wear-resistant additive, anti-friction additive, binder, emulsifier or dispersing agent, crosslinking or curing agent, or as a water absorption inhibitor or as a fluidizing agent, as an antibacterial or antifungal surface or as a barrier, to impregnate wood or as an anticorrosive agent or to produce chemicals or paint. The composition according to any one of claims 1 to 6, wherein the composition is a single phase system. Ċ