Diverging technology

Abstract

A method for producing a branched aldehyde intermediate from an α-olefin, and further reacting the branched aldehyde intermediate by a hydrogenation reaction, a surfactant formation reaction, and other chemical derivative formation reactions to produce a branched alcohol, a branched surfactant, and other branched derivatives. A method for producing an isomerized olefin, a branched aldehyde, a branched alcohol, a branched surfactant, and other branched derivatives by isomerization, hydroformylation, hydrogenation, a surfactant formation reaction, and other derivative formation reactions.

Description

Technical Field

[0001] The present invention relates to the generation of branched aldehyde intermediates, and methods for the production, manufacture, and use of branched aldehyde intermediates and / or one or more branched products derived from branched aldehyde intermediates.

[0002] (Cross - reference to related applications) This patent application is a non - provisional and PCT application claiming the benefit of the filing date of co - pending U.S. Provisional Patent Application No. 63 / 346,899, entitled "Branched Technologies", filed on May 29, 2022 (2022, May 29; 29.05.22). The European - style date numerical format represents DD.MM.YY, where YY is the last two digits of the year, i.e., 20YY.

[0003] (Incorporation by reference) This patent application incorporates by reference in its entirety co - pending U.S. Provisional Patent Application No. 63 / 346,899, entitled "Branched Technologies", filed on May 29, 2022 (2022, May 29; 29.05.22).

Background Art

[0004] In the chemical industry, there has long been a need to produce branched aldehydes, branched alcohols, and branched products obtained from branched aldehydes and branched alcohols in a cost - effective manner. Inexpensive α - olefins can be supplied in large quantities. However, methods for efficiently and cost - effectively producing branched aldehydes, branched alcohols, and branched products on an industrial scale from α - olefins as raw materials are not known.

Summary of the Invention

[0005] α-olefins are supplied in large quantities worldwide and are inexpensive. α-olefins are usually produced through an ethylene oligomerization process from ethylene at an economical price. However, most of these α-olefins are linear, and a major problem is that there is no known method for efficiently and cost-effectively producing branched products from linear α-olefins. Specifically, there is no known method for efficiently producing valuable substances such as branched aldehydes and branched alcohols on an industrial scale using α-olefins as raw materials. According to various embodiments of the present specification, a plurality of branched aldehyde products can be simultaneously produced from an α-olefin raw material. In the embodiments of the present specification, a plurality of branched alcohol products can be simultaneously produced from an α-olefin raw material.

[0006] It is known that α-olefins can be hydroformylated to produce aldehyde products. However, these products are predominantly linear because the olefin functional group (i.e., double bond) is in the α-position (i.e., between the first and second carbons), resulting in the formation of linear aldehydes. For example, hydroformylation of 1-dodecene, a C12 α-olefin, produces a C13 aldehyde product consisting essentially of 1-tridecanal, a linear aldehyde. To produce branched products, it is necessary, as a first step, to isomerize the olefin functional group from the α-position to an internal olefin position and then, as a second step, to hydroformylate the olefin to an aldehyde. Thus, a branched aldehyde product can be produced from a linear α-olefin starting material by a two-step process of a first isomerization and a second hydroformylation. The use of the same catalyst for both the isomerization step and the hydroformylation step is highly advantageous in that this two-step process can be carried out efficiently and economically. The branched aldehydes produced via this two-step process from α-olefins are mostly "2-alkyl" branched aldehydes in which the branching occurs at the second carbon from the aldehyde functional group. From this 2-alkyl branched aldehyde, a 2-alkyl branched alcohol product can be efficiently produced by hydrogenation, and other 2-alkyl derivatives such as surfactants can be produced by further reactions. In these products, it is known that the position of the alkyl branch and the length of the alkyl branch are important for the properties of the final product.

[0007] In one embodiment, a two-step process for producing a branched aldehyde product that is 25% to 98+% branched and greater than 20% branched, produced from an α-olefin feedstock, is disclosed. Also, the two-step process disclosed herein uses a rhodium organophosphorus catalyst in both the first-stage isomerization reaction step and the second-stage hydroformylation reaction step. In one embodiment, the two-step process disclosed herein uses a cobalt organophosphorus catalyst in both the first-stage isomerization reaction step and the second-stage hydroformylation reaction step. In one embodiment, the two-step process disclosed herein uses a cobalt-rhodium organophosphorus mixed catalyst in both the first-stage isomerization reaction step and the second-stage hydroformylation reaction step.

[0008] In one embodiment, an embodiment of the method disclosed herein is a method having a first process step and a second process step. The first process step can be a reaction that isomerizes an α-olefin at a first pressure in an atmosphere of carbon monoxide (CO) and hydrogen (H2) (also referred to as "CO / H2"). In the isomerization step, it can be catalyzed by a first catalyst comprising an organometallic complex of rhodium and one type of organophosphorus ligand, or an organometallic complex of rhodium and two or more types of organophosphorus ligands, and an isomerized olefin can be produced by isomerization. The second step of the present embodiment can be a reaction that hydroformylates the isomerized olefin at a second pressure higher than the first pressure in a CO / H2 atmosphere. In the hydroformylation step, it can be catalyzed by the first catalyst, and a branched aldehyde can be produced by hydroformylation.

[0009] In one embodiment, the catalyst used in the isomerization step can be the same catalyst as the catalyst used in the hydroformylation step. In one embodiment, the second pressure can be lower than the first pressure. In another embodiment, the first pressure and the second pressure are different. Thus, optionally, the second pressure can be higher or lower than the first pressure.

[0010] In one embodiment, the organophosphorus ligand can be a phosphine. As a non-limiting example of a phosphine ligand, the phosphine ligand may be triphenylphosphine. In another embodiment, the organophosphorus ligand can be a phosphite. As a non-limiting example of a phosphite ligand, the phosphite ligand may be tris(2,4-di-t-butylphenyl) phosphite. In yet another embodiment, a mixture of different types of organophosphorus ligands, for example, a mixture of a phosphine and a phosphite can be used. As a non-limiting example of a mixture of organophosphorus ligands, the organophosphorus ligand may be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the α-olefin can be a C4-C36 α-olefin. In one embodiment, the first catalyst can be formed when the molar ratio of phosphorus to rhodium is in the range of 1:1 to 1000:1.

[0011] In one embodiment, the molar ratio of H2 to CO in the isomerization step can be in the range of 10:1 to 1:10. In one embodiment, the molar ratio of H2 to CO in the hydroformylation step can be in the range of 10:1 to 1:10. In one embodiment, the molar ratio of H2 to CO in the isomerization step may be the same as the molar ratio of H2 to CO in the hydroformylation step. In one embodiment, the molar ratio of H2 to CO in the isomerization step may be different from the molar ratio of H2 to CO in the hydroformylation step.

[0012] In one embodiment, the α-olefin can include at least one of a short-chain α-olefin, a medium-chain α-olefin, and a long-chain α-olefin. In one embodiment, the α-olefin can include at least one of α-olefins having 4 or more carbon atoms. In one embodiment, the α-olefin can include at least one of α-olefins having 4 or more carbon atoms, α-olefins having 6 or more carbon atoms, α-olefins having 10 or more carbon atoms, α-olefins having 16 or more carbon atoms, α-olefins having 20 or more carbon atoms, α-olefins having 30 or more carbon atoms, and α-olefins having 36 or more carbon atoms.

[0013] In one embodiment, an isomerization reaction produces a reaction product containing 20 wt% or more of isomerized olefins through isomerization.

[0014] In one embodiment, the isomerization step produces a reaction product containing 5 wt% or more, or 10 wt% or more, or 15 wt% or more, or 20 wt% or more, or 30 wt% or more, or 40 wt% or more, or 50 wt% or more, or 60 wt% or more, or 70 wt% or more, or 80 wt% or more, or 90 wt% or more, or 95 wt% or more, or 99 wt% or more of isomerized olefins.

[0015] In one embodiment, the hydroformylation step produces a reaction product containing 25 wt% or more, or 30 wt% or more, or 40 wt% or more, or 50 wt% or more, or 60 wt% or more, or 70 wt% or more, or 80 wt% or more, or 90 wt% or more, or 95 wt% or more, or 99 wt% or more of branched aldehydes.

[0016] In one embodiment, the method comprises providing a first catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; activating the first catalyst with CO to obtain an activated first catalyst; isomerizing an α-olefin with the activated first catalyst at a first pressure to produce an isomerized olefin; providing hydrogen; and hydroformylating the isomerized olefin by reaction with CO and H2 at a second pressure to produce a branched aldehyde. In one embodiment, the isomerization step is carried out in an atmosphere containing 10 to 100 mol% of CO and 0 to 90 mol% of hydrogen. In one embodiment, the isomerization step is carried out in an atmosphere containing both CO and H2. In one embodiment, the molar ratio of CO to H2 in the isomerization step can be in the range of 10:1 to 1:10. In one embodiment, the molar ratio of CO to H2 in the hydroformylation step can be in the range of 10:1 to 1:10. In one embodiment, the α-olefin is a linear α-olefin having a carbon number in the range of C4 to C36. In one embodiment, the α-olefin can be a C4 to C36 α-olefin. In one embodiment, the organic phosphorus ligand can be phosphine. As a non-limiting example of a phosphine ligand, the phosphine ligand may be triphenylphosphine. In another embodiment, the organic phosphorus ligand can be phosphite. As a non-limiting example of a phosphite ligand, the phosphite ligand may be tris(2,4-di-t-butylphenyl) phosphite. In yet another embodiment, a mixture of different types of organic phosphorus ligands, for example, a mixture of phosphine and phosphite can be used. As a non-limiting example of a mixture of organic phosphorus ligands, the organic phosphorus ligand may be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the first catalyst can be formed when the molar ratio of phosphorus to rhodium is in the range of 1:1 to 1000:1.

[0017] In one embodiment, the method includes providing CO and H2, providing a first catalyst that is an organometallic complex of rhodium and one type of organic phosphorus ligand or an organometallic complex of rhodium and two or more types of organic phosphorus ligands, providing a linear α-olefin, isomerizing the linear α-olefin (also described as a normal α-olefin) with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin, and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde. In one embodiment, the branched aldehyde is a 2-alkyl branched aldehyde. In one embodiment, the linear α-olefin is a C4-C36 linear α-olefin. In one embodiment, the branched aldehyde produced from the C4-C36 linear α-olefin is a C5-C37 branched aldehyde. In one embodiment, the linear α-olefin is 1-butene and the branched aldehyde can be branched pentanal. In one embodiment, the linear α-olefin is 1-hexene and the branched aldehyde can be branched heptanal. In one embodiment, the linear α-olefin is 1-octene and the branched aldehyde can be branched nonanal. In one embodiment, the linear α-olefin is 1-decene and the branched aldehyde can be branched undecanal. In one embodiment, the linear α-olefin is 1-dodecene and the branched aldehyde can be branched tridecanal. In one embodiment, the linear α-olefin is 1-tetradecene and the branched aldehyde can be branched pentadecanal.

[0018] In one embodiment, the linear α-olefin can be 1-hexadecene and the branched aldehyde can be branched heptadecanal. In one embodiment, the linear α-olefin can be 1-octadecene and the branched aldehyde can be branched nonadecanal. In one embodiment, the organophosphorus ligand can be phosphine. As a non-limiting example of a phosphine ligand, the phosphine ligand may be triphenylphosphine. In another embodiment, the organophosphorus ligand can be phosphite. As a non-limiting example of a phosphite ligand, the phosphite ligand may be tris(2,4-di-t-butylphenyl) phosphite. In yet another embodiment, a mixture of different types of organophosphorus ligands, for example, a mixture of phosphine and phosphite, can be used. As a non-limiting example of a mixture of organophosphorus ligands, the organophosphorus ligand may be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite.

[0019] In one embodiment, the first catalyst is formed when the molar ratio of phosphorus to rhodium ranges from 1:1 to 1000:1. In one embodiment, the first catalyst is formed in the isomerization step and / or reactor when the molar ratio of phosphorus to rhodium ranges from 1:1 to 1000:1. In one embodiment, the first catalyst is formed in the hydroformylation step and / or reactor when the molar ratio of phosphorus to rhodium ranges from 1:1 to 1000:1.

[0020] In one embodiment, the method includes providing CO and H2, providing a first catalyst that is an organometallic complex of rhodium and one type of organic phosphorus ligand or an organometallic complex of rhodium and two or more types of organic phosphorus ligands, providing an α-olefin, isomerizing the α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin, and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde. In one embodiment, the α-olefin can be a C4-C36 α-olefin. In one embodiment, the organic phosphorus ligand can be a phosphine. As a non-limiting example of a phosphine ligand, the phosphine ligand may be triphenylphosphine. In another embodiment, the organic phosphorus ligand can be a phosphite. As a non-limiting example of a phosphite ligand, the phosphite ligand may be tris(2,4-di-t-butylphenyl) phosphite. In yet another embodiment, a mixture of different types of organic phosphorus ligands, for example, a mixture of phosphine and phosphite, can be used. As a non-limiting example of a mixture of organic phosphorus ligands, the organic phosphorus ligand may be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the first catalyst can be formed when the molar ratio of phosphorus to rhodium is in the range of 1:1 to 1000:1.

[0021] In one embodiment, the method comprises providing CO and H2; providing a first catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; providing an α-olefin; isomerizing the α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin; hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde; and hydrogenating the branched aldehyde to produce a branched alcohol. In one embodiment, the isomerization step produces a reaction product containing 5 wt% or more of isomerized olefin, or 10 wt% or more of isomerized olefin, or 20 wt% or more of isomerized olefin, or 40 wt% or more of isomerized olefin. In one embodiment, the hydroformylation step produces a reaction product containing 25 wt% or more of branched aldehyde, or 50 wt% or more of branched aldehyde. In one embodiment, the hydrogenation step produces a reaction product containing 25 wt% or more of branched alcohol, or 50 wt% or more of branched alcohol.

[0022] In one embodiment, a method for producing a branched aldehyde includes providing an α-olefin, providing a first catalyst, isomerizing the alkene with the first catalyst at a first pressure in an atmosphere containing CO and H2 to produce a composition of an intermediate isomerized olefin product containing an internal olefin, hydroformylating the intermediate isomerized olefin product with the first catalyst at a second pressure higher than the first pressure in an atmosphere containing CO and H2, and producing a branched aldehyde product. Also, in one embodiment, the method may include separating the branched aldehyde product from the first catalyst stream by a distillation process. Also, in one embodiment, the method may include hydrogenating the branched aldehyde in the presence of a hydrogenation catalyst and producing a composition of a branched alcohol product. In one embodiment, the α-olefin is an α-olefin having 4 to 36 or more carbon atoms. In one embodiment, the catalyst is a rhodium catalyst. In one embodiment, the catalyst is a homogeneous rhodium catalyst. In one embodiment, the catalyst is a homogeneous rhodium catalyst having an organic phosphorus ligand. In one embodiment, the first pressure can range from 0.01 bar (absolute pressure) to 20 bar (absolute pressure) (in gauge pressure, -0.99 bar (g) (negative value, vacuum) to 19 bar (g)). In one embodiment, the intermediate isomerized olefin product may contain at least 10 wt% or at least 20 wt% of internal olefins. In one embodiment, the second pressure can range from 1 bar (g) to 400 bar (g). The branched aldehyde product may contain at least 25 wt% of branched aldehyde.

[0023] In one embodiment, the method comprises providing CO and H2; providing a first catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; providing an α-olefin; isomerizing the α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin; hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde; hydrogenating the branched aldehyde to produce a branched alcohol; and producing a branched surfactant from the branched alcohol. In one embodiment, the production step includes sulfating the branched alcohol to produce a branched alcohol sulfate. In one embodiment, the production step includes alkoxylating the branched alcohol to produce a branched alkoxylated alcohol. In one embodiment, the alkoxylating agent can be ethylene oxide, propylene oxide, or a mixture of ethylene oxide and propylene oxide. In one embodiment, the alkoxylating agent can be ethylene oxide and propylene oxide added simultaneously or stepwise (i.e., block oxide). In one embodiment, the alkoxylating agent can be ethylene oxide, propylene oxide, butylene oxide, or a mixture of ethylene oxide, propylene oxide, and butylene oxide. In one embodiment, the branched alkoxylated alcohol can be sulfated to produce a branched sulfated alkoxylated alcohol. In one embodiment, the isomerization step can produce a reaction product containing 20 wt% or more of internal olefins. In one embodiment, isomerization can produce a reaction product containing 50 wt% or more of internal olefins. In one embodiment, hydroformylation can produce a reaction product containing 25 wt% or more of branched aldehydes. In one embodiment, hydroformylation can produce a reaction product containing 50 wt% or more of branched aldehydes. In one embodiment, hydrogenation can produce a reaction product containing 40 wt% or more of branched alcohols.In one embodiment, a reaction product containing 50 wt% or more of a branched alcohol can be produced by a hydrogenation step. In one embodiment, the surfactant may contain 40 wt% or more of a branched surfactant. In one embodiment, the surfactant may contain 50 wt% or more of a branched surfactant.

[0024] (Branched alcohol)

[0025] In one embodiment, a method for producing a branched alcohol includes steps of providing CO and H2, providing a first catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand or an organometallic complex of rhodium and two or more types of organic phosphorus ligands, providing an α-olefin, isomerizing the α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin, hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde, and hydrogenating the branched aldehyde to produce a branched alcohol. In one embodiment, a reaction product containing 5 wt% or more of an isomerized olefin is produced by the isomerization step. In one embodiment, a reaction product containing 10 wt% or more of an isomerized olefin is produced by the isomerization step. In one embodiment, a reaction product containing 15 wt% or more of an isomerized olefin is produced by the isomerization step. In one embodiment, a reaction product containing 20 wt% or more of an isomerized olefin is produced by the isomerization step. In one embodiment, a reaction product containing 25 wt% or more of a branched aldehyde is produced by the hydroformylation step. In one embodiment, a reaction product containing 30 wt% or more of a branched aldehyde is produced by the hydroformylation step. In one embodiment, a reaction product containing 40 wt% or more of a branched alcohol is produced by the hydrogenation step. In one embodiment, a reaction product containing 50 wt% or more of a branched alcohol is produced by the hydrogenation step.

[0026] A method for producing branched alcohols, comprising the steps of: providing a C4-C36 α-olefin; providing a rhodium catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; isomerizing the C4-C36 olefin with the rhodium catalyst under a CO / H2 atmosphere at a pressure of 0.1 bar(g) to 10 bar(g) to produce a composition of an intermediate isomerized olefin product containing at least 10 wt% of internal (non-α) olefins; hydroformylating the intermediate isomerized olefin product with the rhodium catalyst under a CO / H2 atmosphere at a pressure of 5 bar(g) to 400 bar(g) to produce a composition of a branched aldehyde product containing at least 25 wt% of branched aldehydes; separating the branched aldehyde product from the rhodium-containing catalyst stream by a distillation process; hydrogenating the branched aldehyde at an elevated hydrogen pressure in the presence of a hydrogenation catalyst to produce a composition of a branched alcohol product containing at least 40 wt% of branched alcohols.

[0027] A method for producing branched alcohols, comprising the steps of: providing a C4-C36 α-olefin; providing a rhodium catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; isomerizing the C4-C36 olefin with the rhodium catalyst under a CO / H2 atmosphere at a pressure of 0.01 bar (absolute pressure) to 20 bar (absolute pressure) to produce a composition of an intermediate isomerized olefin product containing at least 10 wt% of internal (non-α) olefins; hydroformylating the intermediate isomerized olefin product with the rhodium catalyst under a CO / H2 atmosphere at a pressure of 1 bar (g) to 400 bar (g) to produce a composition of a branched aldehyde product containing at least 25 wt% of branched aldehydes; separating the branched aldehyde product from the rhodium-containing catalyst stream by a distillation process; hydrogenating the branched aldehyde at an elevated hydrogen pressure in the presence of a hydrogenation catalyst to produce a composition of a branched alcohol product containing at least 40 wt% of branched alcohols.

[0028] A composition comprising a mixture of C8-C36 alcohols, wherein less than 50% of the C8-C36 alcohols are linear alcohols, more than 30% of the C8-C36 alcohols are 2-methyl branched alcohols, and more than 8% of the C8-C36 alcohols are 2-ethyl branched alcohols. In one embodiment, more than 10% of the alcohols are 2-ethyl branched alcohols. In one embodiment, more than 12% of the alcohols are 2-ethyl branched alcohols. In one embodiment, more than 14% of the alcohols are 2-ethyl branched alcohols. In one embodiment, more than 16% of the alcohols are 2-ethyl branched alcohols. In one embodiment, more than 18% of the alcohols are 2-ethyl branched alcohols. In one embodiment, more than 20% of the alcohols are 2-ethyl branched alcohols.

[0029] In one embodiment, a composition comprising a mixture of C8-C36 alcohols can be produced, wherein less than 60% of the mixture of C8-C36 alcohols is a linear alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, and more than 8% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol.

[0030] In one embodiment, the mixture of C8-C36 alcohols contains about 90% or more of C13 alcohol (i.e., tridecanol), less than 60% of the mixture of C8-C36 alcohols is linear 1-tridecanol, more than 25% of the mixture of C8-C36 alcohols is 2-methyldodecanol, and more than 8% of the mixture of C8-C36 alcohols is 2-ethylundecanol. In one embodiment, more than 10% of the mixture of C8-C36 alcohols is 2-ethylundecanol. In one embodiment, more than 12% of the mixture of C8-C36 alcohols is 2-ethylundecanol. In one embodiment, more than 14% of the mixture of C8-C36 alcohols is 2-ethylundecanol. In one embodiment, more than 16% of the mixture of C8-C36 alcohols is 2-ethylundecanol. In one embodiment, more than 18% of the mixture of C8-C36 alcohols is 2-ethylundecanol. In one embodiment, more than 20% of the mixture of C8-C36 alcohols is 2-ethylundecanol.

[0031] In one embodiment, the mixture of C8-C36 alcohols produced contains about 90% or more C15 alcohol (i.e., pentadecanol), less than 60% of the mixture of C8-C36 alcohols is linear 1-pentadecanol, more than 25% of the mixture of C8-C36 alcohols is 2-methyltetradecanol, and more than 8% of the mixture of C8-C36 alcohols is 2-ethyltridecanol. In one embodiment, more than 10% of the mixture of C8-C36 alcohols is 2-ethyltridecanol. In one embodiment, more than 12% of the mixture of C8-C36 alcohols is 2-ethyltridecanol. In one embodiment, more than 14% of the mixture of C8-C36 alcohols is 2-ethyltridecanol. In one embodiment, more than 16% of the mixture of C8-C36 alcohols is 2-ethyltridecanol. In one embodiment, more than 18% of the mixture of C8-C36 alcohols is 2-ethyltridecanol. In one embodiment, more than 20% of the mixture of C8-C36 alcohols is 2-ethyltridecanol.

[0032] In one embodiment, a method for producing a mixture of two or more branched alcohols includes providing at least two C4 - C36 α - olefins of different chain lengths, providing a first catalyst, isomerizing the α - olefin mixture with the first catalyst at a first pressure in an atmosphere containing CO and H2 to produce a composition of an intermediate isomerized olefin product containing a mixture of α - olefins and internal olefins, hydroformylating the intermediate isomerized olefin product with the first catalyst at a second pressure higher than the first pressure in an atmosphere containing CO and H2 to produce a mixture of at least two branched aldehydes of different C5 - C37 chain lengths, separating the mixture of C5 - C37 branched aldehydes from a rhodium - containing catalyst stream via a distillation process, hydrogenating the mixture of C5 - C37 branched aldehydes at an elevated hydrogen pressure in the presence of hydrogen and a hydrogenation catalyst, and producing a product that is a mixture of two or more branched alcohols containing at least two branched alcohols of different carbon chain lengths in the carbon number range of C5 - C37. In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the catalyst is a rhodium catalyst. In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the catalyst is a homogeneous rhodium catalyst. In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the catalyst is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands. In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the first pressure ranges from 0.1 bar(g) to 10 bar(g). In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the first pressure ranges from 0.01 bar(absolute pressure) to 20 bar(absolute pressure). In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the intermediate isomerized olefin product contains at least 20 wt% of internal olefins. In one embodiment of the method for producing a mixture of C5 - C37 branched alcohols, the second pressure ranges from 5 bar(g) to 400 bar(g).In one embodiment of the method for producing a mixture of C5-C37 branched alcohols, the second pressure ranges from 1 bar(g) to 400 bar(g). In one embodiment of the method for producing a mixture of C5-C37 branched alcohols, the mixture of C5-C37 branched alcohols is a 2-alkyl branched alcohol. In one embodiment of the method for producing a mixture of C5-C37 branched alcohols, the mixture of C5-C37 branched alcohols contains at least 25 wt% branched alcohol.

[0033] A composition comprising a mixture of C9-C35 aldehydes, wherein less than 60 wt% of the mixture of C9-C35 aldehydes is a linear aldehyde, more than 25 wt% of the mixture of C9-C35 aldehydes is a 2-methyl branched aldehyde, more than 8 wt% of the mixture of C9-C35 aldehydes is a 2-ethyl branched aldehyde, and the freezing point of the mixture of C9-C35 aldehydes is less than -10 °C is provided. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -15 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -20 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -25 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -30 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -40 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -50 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -60 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -70 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -80 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -90 °C. In one embodiment, the freezing point of the mixture of C9-C35 aldehydes is less than -100 °C.

[0034] A composition comprising a mixture of C9 - C35 alcohols, wherein less than 60 wt% of the mixture of C9 - C35 alcohols is linear alcohol, more than 25 wt% of the mixture of C9 - C35 alcohols is 2 - methyl - branched alcohol, more than 8 wt% of the mixture of C9 - C35 alcohols is 2 - ethyl - branched alcohol, and the freezing point of the mixture of C9 - C35 alcohols is less than - 10°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 15°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 20°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 25°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 30°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 40°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 50°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 60°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 70°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 80°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 90°C. In one embodiment, the freezing point of the mixture of C9 - C35 alcohols is less than - 100°C.

[0035] In one embodiment of a method for producing a mixture of C5 - C37 branched alcohols, the mixture has at least two different C5 - C37 chain lengths, and the method may further include separating a mixture of C5 - C37 branched alcohols containing at least two different C5 - C37 branched alcohols into individual purified branched alcohol products via a series of distillation processes. Each distilled purified branched alcohol product consists essentially of a product of a single carbon chain length within the C5 - C37 carbon number range.

[0036] In one embodiment, a method for producing a mixture of C5-C37 branched alcohols further includes the steps of providing two α-olefins, a C12 α-olefin (i.e., 1-dodecene) which is a first α-olefin and a C14 α-olefin (i.e., 1-tetradecene) which is a second α-olefin, generating a mixture of a branched C13 aldehyde and a branched C15 aldehyde, and generating a mixture of a branched C13 alcohol and a branched C15 alcohol. In one embodiment, a method for producing a mixture of C5-C37 branched alcohols further includes separating a mixture of a C13 branched alcohol and a C15 branched alcohol, purifying the C13 branched alcohol product by a first distillation step, and purifying the branched C15 alcohol product by a second distillation step.

[0037] (Composition characteristics)

[0038] As used herein, the term "less" is used synonymously with "lower than" or "under". Specifically, with respect to the freezing point, a temperature of less than -X degrees is synonymous with the expression "lower than -X degrees" and also synonymous with the expression "under -X degrees". Negative temperatures are measured as less than 0 degrees, lower than 0 degrees, or under 0 degrees.

[0039] There is provided a composition comprising a mixture of C9-C35 aldehydes, wherein less than 60 wt% of the mixture of C9-C35 aldehydes is a linear aldehyde, more than 25 wt% of the mixture of C9-C35 aldehydes is a 2-methyl branched aldehyde, more than 8 wt% of the mixture of C9-C35 aldehydes is a 2-ethyl branched aldehyde, and the freezing point of the mixture of C9-C35 aldehydes is in the range of less than -10°C to less than -100°C, for example, less than -10°C, less than -20°C, less than -30°C, less than -40°C, less than -60°C, less than -80°C, less than -100°C, or less than -125°C.

[0040] In some embodiments, the freezing point of the mixture of C9-C35 aldehydes is in the range of -10°C or lower to -100°C or lower, for example, -10°C or lower, -20°C or lower, -30°C or lower, -40°C or lower, -60°C or lower, -80°C or lower, -100°C or lower, or -125°C or lower.

[0041] A composition comprising a mixture of C9-C35 alcohols, wherein less than 60 wt% of the mixture of C9-C35 alcohols is a linear alcohol, more than 25 wt% of the mixture of C9-C35 alcohols is a 2-methyl branched alcohol, more than 8 wt% of the mixture of C9-C35 alcohols is a 2-ethyl branched alcohol, and the freezing point of the mixture of C9-C35 alcohols is less than -10°C, for example, less than -10°C, less than -20°C, less than -30°C, less than -40°C, less than -60°C, less than -80°C, less than -100°C, or less than -125°C, is provided.

[0042] In some embodiments, the freezing point of the mixture of C9-C35 alcohols is in the range of -10°C or lower to -100°C or lower, for example, -10°C or lower, -20°C or lower, -30°C or lower, -40°C or lower, -60°C or lower, -80°C or lower, -100°C or lower, or -125°C or lower.

[0043] (Downstream products of branched alcohols)

[0044] The branched alcohol products produced by the methods of the various embodiments disclosed herein can be used to produce innumerable different products.

[0045] In one embodiment, the branched alcohol products of the methods disclosed herein can be used to produce fuels, lubricant additives, food additives, solvents, emulsifiers, softeners, thickeners, coating agents, elastomers, adhesives, antioxidants, polymer stabilizers, cosmetics, and the like.

[0046] (Carboxylated products)

[0047] In one embodiment, the branched alcohol products of the methods disclosed herein can be carboxylated by reaction with a carboxylic acid, dicarboxylic acid, or polyacid to produce esters. Uses for such esters produced by the methods disclosed herein include lubricants, plasticizers, solvents, coating agents, inks, cleaners, binders, paint strippers, and / or oilfield chemicals, among others.

[0048] (Branched aldehyde, amine, carboxylic acid products)

[0049] In various embodiments, a number of downstream products can be manufactured as products of the methods disclosed herein. The branched aldehydes produced by this embodiment can be reacted to produce a number of branched aldehyde products. The branched aldehydes can be further reacted to produce branched amine products. In other embodiments, the branched aldehydes can be reacted to produce branched carboxylic acid products.

[0050] In one embodiment, the method comprises the steps of isomerizing an α-olefin under a CO / H2 atmosphere at a first pressure, the isomerization being catalyzed by a first catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand or an organometallic complex of rhodium and two or more types of organic phosphorus ligands, to produce an isomerized olefin; and hydroformylating the isomerized olefin under a CO / H2 atmosphere at a second pressure higher than the first pressure, the hydroformylation being catalyzed by the first catalyst, to produce a branched aldehyde. In one embodiment, the α-olefin is a C4-C35 α-olefin. In one embodiment, the first catalyst is formed when the molar ratio of phosphorus to rhodium is in the range of 1:1 to 1000:1. In one embodiment, the first pressure is in the range of 0.01 bar(g) to 10 bar(g). In one embodiment, the first pressure is in the range of 0.01 bar(absolute pressure) to 20 bar(absolute pressure). In one embodiment, the isomerization occurs at a temperature in the range of 30°C to 500°C. In one embodiment, the second pressure is in the range of 5 bar(g) to 400 bar(g). In one embodiment, the second pressure is in the range of 1 bar(g) to 400 bar(g). In one embodiment, the hydroformylation occurs at a temperature in the range of 30°C to 500°C. In one embodiment, the α-olefin is a short-chain α-olefin. In one embodiment, the α-olefin is a medium-chain α-olefin. In one embodiment, the α-olefin is a long-chain α-olefin. In one embodiment, the α-olefin contains an α-olefin of C4 or higher. In one embodiment, the α-olefin contains a C5 α-olefin. In one embodiment, the α-olefin contains an α-olefin of C6 or higher. In one embodiment, the α-olefin contains an α-olefin of C10 or higher. In one embodiment, the α-olefin contains an α-olefin of C16 or higher. In one embodiment, the α-olefin contains an α-olefin of C20 or higher. In one embodiment, the α-olefin contains an α-olefin of C30 or higher. In one embodiment, the α-olefin contains an α-olefin of C36 or higher. In one embodiment, the isomerization produces a reaction product containing 5 wt% or more of the isomerized olefin. In one embodiment, the isomerization produces a reaction product containing 10 wt% or more of the isomerized olefin.In one embodiment, isomerization produces a reaction product containing 15 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 20 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 25 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 30 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 40 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 50 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 60 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 70 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 80 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 90 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 95 wt% or more of isomerized olefins. In one embodiment, isomerization produces a reaction product containing 99 wt% or more of isomerized olefins. In one embodiment, hydroformylation produces a reaction product containing 25 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 30 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 40 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 50 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 60 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 70 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 80 wt% or more of branched aldehydes. In one embodiment, hydroformylation produces a reaction product containing 90 wt% or more of branched aldehydes.In one embodiment, a reaction product containing 95 wt% or more of branched aldehyde is produced by hydroformylation. In one embodiment, a reaction product containing 99 wt% or more of branched aldehyde is produced by hydroformylation. In one embodiment, the α-olefin is a C4-C36 α-olefin. In one embodiment, the α-olefin is a mixture of one or more C4-C36 α-olefins. In one embodiment, isomerization occurs in the range of a CO:H2 molar ratio of 10:1 to 1:10. In one embodiment, hydroformylation occurs in the range of a CO:H2 molar ratio of 10:1 to 1:10.

[0051] In one embodiment, the method comprises providing a first catalyst which is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; activating the first catalyst with CO to obtain an activated first catalyst; isomerizing an α-olefin with the activated first catalyst at a first pressure to produce an isomerized olefin; providing hydrogen; and hydroformylating the isomerized olefin by reaction with CO and H2 at a second pressure to produce a branched aldehyde. In one embodiment, the α-olefin is a C4-C35 α-olefin. In one embodiment, the organic phosphorus ligand can be a phosphine. In one embodiment, the phosphine ligand can be triphenylphosphine. In one embodiment, the organic phosphorus ligand can be a phosphite. In one embodiment, the phosphite ligand can be tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, a mixture of different types of organic phosphorus ligands, for example, a mixture of phosphine and phosphite can be used. In one embodiment, the mixture of different types of organic phosphorus ligands can be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the first catalyst is formed when the molar ratio of phosphorus to rhodium is in the range of 1:1 to 1000:1.

[0052] In one embodiment, the method includes providing CO and H2; providing a first catalyst that is an organometallic complex of rhodium and one type of organic phosphorus ligand or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; providing an α-olefin; isomerizing the α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin; and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde. In one embodiment, the α-olefin is a C4-C36 α-olefin. In one embodiment, the α-olefin is a linear α-olefin having a carbon number in the range of C4-C36. In one embodiment, at least one organic phosphorus ligand includes a plurality of identical ligands. In one embodiment, at least one organic phosphorus ligand includes a plurality of ligands, at least two of which are different from each other. In one embodiment, the organic phosphorus ligand can be a phosphine. In one embodiment, the phosphine ligand can be triphenylphosphine. In one embodiment, the organic phosphorus ligand can be a phosphite. In one embodiment, the phosphite ligand can be tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, a mixture of different types of organic phosphorus ligands, for example, a mixture of phosphine and phosphite, can be used. In one embodiment, the mixture of different types of organic phosphorus ligands can be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the first catalyst is formed when the molar ratio of phosphorus to rhodium is in the range of 1:1 to 1000:1.

[0053] In one embodiment, the method includes providing CO and H2, providing a first catalyst that is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands, providing a linear α-olefin, isomerizing the linear α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin, and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde. In one embodiment, the branched aldehyde is a 2-alkyl branched aldehyde. In one embodiment, the linear α-olefin is a C4-C36 linear α-olefin. In one embodiment, the branched aldehyde produced from the C4-C36 linear α-olefin is a C5-C37 branched aldehyde. In one embodiment, the linear α-olefin is 1-butene and the branched aldehyde is branched pentanal. In one embodiment, the linear α-olefin is 1-hexene and the branched aldehyde is branched heptanal. In one embodiment, the linear α-olefin is 1-octene and the branched aldehyde is branched nonanal. In one embodiment, the linear α-olefin is 1-decene and the branched aldehyde is branched undecanal. In one embodiment, the linear α-olefin is 1-dodecene and the branched aldehyde is branched tridecanal. In one embodiment, the linear α-olefin is 1-tetradecene and the branched aldehyde is branched pentadecanal. In one embodiment, the linear α-olefin is 1-hexadecene and the branched aldehyde is branched heptadecanal. In one embodiment, the linear α-olefin is 1-octadecene and the branched aldehyde is branched nonadecanal. In one embodiment, the organic phosphorus ligand can be a phosphine. In one embodiment, the phosphine ligand can be triphenylphosphine. In one embodiment, the organic phosphorus ligand can be a phosphite. In one embodiment, the phosphite ligand can be tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, a mixture of different types of organic phosphorus ligands, for example, a mixture of phosphine and phosphite, can be used.In one embodiment, the mixture of different types of organophosphorus ligands can be a mixture of triphenylphosphine and tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the first catalyst is formed when the molar ratio of phosphorus to rhodium ranges from 1:1 to 1000:1. In one embodiment, the linear α-olefin is a mixture of one or more C4-C36 linear α-olefins.

[0054] A method for producing a branched aldehyde, comprising: providing an α-olefin; providing a first catalyst; isomerizing an alkene with the first catalyst at a first pressure in an atmosphere containing CO and H2 to produce a composition of an intermediate isomerized olefin product containing an internal olefin; hydroformylating the intermediate isomerized olefin product with the first catalyst at a second pressure higher than the first pressure in an atmosphere containing CO and H2; and producing a branched aldehyde product. In one embodiment, the method further comprises separating the branched aldehyde product from the first catalyst stream by a distillation process. In one embodiment, the α-olefin is a C4-C36 α-olefin. In one embodiment, the catalyst is a rhodium catalyst. In one embodiment, the catalyst is a homogeneous rhodium catalyst. In one embodiment, the catalyst is an organometallic complex of rhodium and one type of organophosphorus ligand, or an organometallic complex of rhodium and two or more types of organophosphorus ligands. In one embodiment, the first pressure ranges from 0.1 bar(g) to 10 bar(g). In one embodiment, the first pressure ranges from 0.01 bar(absolute pressure) to 20 bar(absolute pressure). In one embodiment, the intermediate isomerized olefin product contains at least 10 wt% of internal olefins. In one embodiment, the intermediate isomerized olefin product contains at least 20 wt% of internal olefins. In one embodiment, the second pressure ranges from 5 bar(g) to 400 bar(g). In one embodiment, the second pressure ranges from 1 bar(g) to 400 bar(g). In one embodiment, the branched aldehyde product contains at least 25 wt% of branched aldehydes.

[0055] A composition comprising a mixture of C8-C36 aldehydes, wherein less than 50% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 30% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. In one embodiment, more than 10% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. In one embodiment, more than 12% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. In one embodiment, more than 14% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. In one embodiment, more than 16% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. In one embodiment, more than 18% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. In one embodiment, more than 20% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde.

[0056] In one embodiment, the composition comprises a mixture of C8-C36 aldehydes, wherein less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde.

[0057] In one embodiment, the mixture of C8-C36 aldehydes contains at least about 90% C13 aldehyde (i.e., tridecanal), less than 60% of the mixture of C8-C36 aldehydes is linear 1-tridecanal, more than 25% of the mixture of C8-C36 aldehydes is 2-methyldodecanal, and more than 8% of the mixture of C8-C36 aldehydes is 2-ethylundecanal. In one embodiment, more than 10% of the mixture of C8-C36 aldehydes is 2-ethylundecanal. In one embodiment, more than 12% of the mixture of C8-C36 aldehydes is 2-ethylundecanal. In one embodiment, more than 14% of the mixture of C8-C36 aldehydes is 2-ethylundecanal. In one embodiment, more than 16% of the mixture of C8-C36 aldehydes is 2-ethylundecanal. In one embodiment, more than 18% of the mixture of C8-C36 aldehydes is 2-ethylundecanal. In one embodiment, more than 20% of the mixture of C8-C36 aldehydes is 2-ethylundecanal.

[0058] In one embodiment, the composition contains a mixture of C8-C36 aldehydes, less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes can be a 2-ethyl branched aldehyde.

[0059] In one embodiment, the aldehyde mixture contains at least about 90% C15 aldehyde (i.e., pentadecanal), less than 60% of the aldehyde mixture is linear 1-pentadecanal, more than 25% of the aldehyde mixture is 2-methyltetradecanal, and more than 8% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, more than 10% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, more than 12% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, more than 14% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, more than 16% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, more than 18% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, more than 20% of the aldehyde mixture is 2-ethyltridecanal.

[0060] In one embodiment, a method for producing a product aldehyde composition comprising a mixture of two or more branched aldehydes, the method comprising: providing at least two C4-C36 α-olefins of different chain lengths; providing a first catalyst; isomerizing the α-olefin mixture with the first catalyst at a first pressure in an atmosphere containing CO and H2 to produce a composition of an intermediate isomerized olefin product comprising a mixture of α-olefins and internal olefins; hydroformylating the intermediate isomerized olefin product with the first catalyst at a second pressure higher than the first pressure in an atmosphere containing CO and H2; and producing a product aldehyde composition that is a mixture of at least two C5-C37 branched aldehydes of different chain lengths.

[0061] In one embodiment, a method for producing a product aldehyde composition containing a mixture of C5-C37 branched aldehydes further includes separating the mixture of C5-C37 branched aldehydes from a first catalyst stream by a distillation process. In one embodiment, the first catalyst is a rhodium catalyst. In one embodiment, the first catalyst is a homogeneous rhodium catalyst. In one embodiment, the first catalyst is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands. In one embodiment, the first pressure ranges from 0.1 bar(g) to 10 bar(g). In one embodiment, the first pressure ranges from 0.01 bar(absolute pressure) to 20 bar(absolute pressure). In one embodiment, the intermediate isomerized olefin product contains at least 20 wt% internal olefins. In one embodiment, the second pressure ranges from 5 bar(g) to 400 bar(g). In one embodiment, the second pressure ranges from 1 bar(g) to 400 bar(g). In one embodiment, the produced branched aldehyde is a 2-alkyl branched aldehyde. In one embodiment, the product aldehyde composition contains at least 25 wt% branched aldehyde.

[0062] In one embodiment, the product aldehyde composition has at least two different C5-C37 chain lengths, and the method may further include separating, via a series of distillation processes, the product aldehyde composition containing a mixture of at least two different C5-C37 branched aldehydes into individual purified branched aldehyde products. Each distilled purified branched aldehyde product consists essentially of a product of a single carbon chain length within the carbon number range of C5-C37.

[0063] (Branched aldehyde product)

[0064] In one embodiment, examples of the branched aldehyde products of the methods disclosed herein include, but are not limited to, flavor molecules, perfume ingredients, solvents, intermediates in plastic manufacturing, dyes, and pharmaceuticals.

[0065] In one embodiment, the branched aldehyde produced by the method disclosed herein can be reacted with ammonia and hydrogen to produce a branched primary amine.

[0066] In one embodiment, the branched aldehyde produced by the method disclosed herein can be reacted with an amine and hydrogen to produce a branched secondary amine.

[0067] In one embodiment, the branched aldehyde produced by the method disclosed herein can be reacted with a secondary amine to produce a branched tertiary amine.

[0068] (Branched amine product)

[0069] In one embodiment, examples of the branched amine products of the method disclosed herein include, but are not limited to, chemical catalysts, corrosion inhibitors, emulsifiers, suspending aids, ion exchange resins, rubber chemicals, antioxidants, stabilizers, antistatic agents, plasticizers, dyes, gasoline and lubricant additives, curing agents for epoxy resins, solvents, metal extractants, photographic developers, solidification inhibitors, and the like.

[0070] In one embodiment, the branched amine product of the method disclosed herein can be an intermediate for the synthesis of pharmaceuticals, herbicides, fungicides, and insecticides.

[0071] In one embodiment, the branched amine product of the method disclosed herein can be alkoxylated to produce an alkoxylated amine surfactant.

[0072] In one embodiment, the branched amine product of the embodiment of the method disclosed herein can be oxidized to produce an amine oxide surfactant.

[0073] (Amine oxide)

[0074] In one embodiment, a mixture of C8-C36 amines in which less than 60% of the amines are linear amines, more than 25% of the amines are 2-methyl branched amines, and more than 8% of the amines are 2-ethyl branched amines is reacted with oxygen or another oxidizing agent to produce an amine oxide composition containing a mixture of C8-C36 amine oxides in which less than 60% of the amine oxides are linear amine oxides, more than 25% of the amine oxides are 2-methyl branched amine oxides, and more than 8% of the amine oxides are 2-ethyl branched amine oxides. As a product of the method, the amine oxide composition can be manufactured.

[0075] In one embodiment, the amine oxide mixture contains a surfactant. In one embodiment, the amine oxide mixture is a surfactant composition. In one embodiment, at least one amine oxide produced is a surfactant.

[0076] (Branched carboxylic acid product)

[0077] In one embodiment, the branched aldehyde product of the method disclosed herein can be oxidized with oxygen or another oxidizing agent to produce a branched carboxylic acid.

[0078] In one embodiment, the branched carboxylic acid product of the method disclosed herein can be a corrosion inhibitor, an emulsifier, an ion exchange resin, a food additive, a flavor molecule, a plastic additive, a lubricant, a solvent, a coating agent, a dye, a rubber chemical, a plasticizer.

[0079] In one embodiment, the method may include providing a feed comprising an α-olefin, providing a catalyst, catalyzing the isomerization of the α-olefin with the catalyst, generating an isomerized olefin by the isomerization of the α-olefin, catalyzing the hydroformylation of the isomerized olefin with the catalyst, and generating a branched aldehyde by the hydroformylation of the isomerized olefin. Also, in one embodiment, the method may include reacting the branched aldehyde with hydrogen and generating a branched alcohol by the reaction of the branched aldehyde.

[0080] Also, in one embodiment, the method may include providing a feed comprising one or more internal olefins. Also, in one embodiment, the method may include providing a feed comprising one or more internal olefins that are C4 - C36 internal olefins. In one embodiment, the method may include providing a feed comprising one or more internal olefins, providing a catalyst, catalyzing the isomerization of the internal olefins with the catalyst, generating an isomerized olefin mixture by the isomerization of the internal olefins, catalyzing the hydroformylation of the isomerized olefin mixture with the catalyst, and generating a branched aldehyde mixture by the hydroformylation of the isomerized olefin mixture. Also, in one embodiment, the method may include reacting the branched aldehyde mixture with hydrogen and generating a branched alcohol mixture by the reaction of the branched aldehyde mixture.

[0081] Also, in one embodiment, the method may include providing a mixed olefin feed that is a mixture of internal olefins and α-olefins. Also, in one embodiment, the method may include providing a mixed olefin feed that is a mixture of one or more C4 - C36 internal olefins and one or more C4 - C36 α-olefins. In one embodiment, the method includes providing a mixed olefin feed, providing a catalyst, catalyzing the isomerization of the mixed olefins with the catalyst, generating an isomerized olefin mixture by the isomerization of the mixed olefins, catalyzing the hydroformylation of the mixed olefins with the catalyst, and generating a branched aldehyde mixture by the hydroformylation of the mixed olefins. Also, in one embodiment, the method may include reacting the branched aldehyde mixture with hydrogen and generating a branched alcohol mixture by the reaction of the branched aldehyde mixture.

[0082] In one embodiment, the method may include providing a C4 - C36 alkene, providing a first catalyst, catalyzing the isomerization of the C4 - C36 alkene with the first catalyst, generating a composition of an intermediate product containing a plurality of isomerized alkenes, wherein the composition of the intermediate product contains at least 60 wt% of the plurality of isomerized alkenes, and hydroformylating the plurality of isomerized alkenes. In one embodiment, the method may further include generating a branched aldehyde. In one embodiment, the method may further include generating a composition of a branched aldehyde product that contains at least 60 wt% of a plurality of branched aldehydes by hydroformylation.

[0083] In one embodiment, the composition comprises a mixture of C8-C36 alcohols, less than 60% of the mixture of C8-C36 alcohols is a linear alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, and more than 8% of the mixture of C8-C36 alcohols can be a 2-ethyl branched alcohol. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 10% of the alcohol is a 2-ethyl branched alcohol. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 12% of the alcohol is a 2-ethyl branched alcohol. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 14% of the alcohol is a 2-ethyl branched alcohol. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 16% of the alcohol is a 2-ethyl branched alcohol. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 18% of the alcohol is a 2-ethyl branched alcohol. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 20% of the alcohol is a 2-ethyl branched alcohol.

[0084] In another embodiment, the composition comprises a mixture of C8-C36 alcohols, less than 50% of the C8-C36 alcohols are linear alcohols, more than 30% of the C8-C36 alcohols are 2-methyl branched alcohols, and more than 8% of the C8-C36 alcohols can be 2-ethyl branched alcohols. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 10% of the alcohols are 2-ethyl branched alcohols. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 12% of the alcohols are 2-ethyl branched alcohols. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 14% of the alcohols are 2-ethyl branched alcohols. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 16% of the alcohols are 2-ethyl branched alcohols. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 18% of the alcohols are 2-ethyl branched alcohols. In one embodiment, the composition can comprise a mixture of C8-C36 alcohols in which more than 20% of the alcohols are 2-ethyl branched alcohols.

[0085] In one embodiment, the composition comprises a mixture of C8 - C36 alcohols, less than 60% of the mixture of C8 - C36 alcohols is a linear alcohol, more than 25% of the mixture of C8 - C36 alcohols is a 2-methyl branched alcohol, more than 8% of the mixture of C8 - C36 alcohols is a 2-ethyl branched alcohol, the alcohol mixture comprises about 90% or more of C13 alcohol (i.e., tridecanol), less than 60% of the alcohol mixture is linear 1-tridecanol, more than 25% of the alcohol mixture is 2-methyldodecanol, and more than 8% of the alcohol mixture can be 2-ethylundecanol. In one embodiment, the composition can comprise a mixture of C8 - C36 alcohols in which more than 10% of the alcohol mixture is 2-ethylundecanol. In one embodiment, the composition can comprise a mixture of C8 - C36 alcohols in which more than 12% of the alcohol mixture is 2-ethylundecanol. In one embodiment, the composition can comprise a mixture of C8 - C36 alcohols in which more than 14% of the alcohol mixture is 2-ethylundecanol. In one embodiment, the composition can comprise a mixture of C8 - C36 alcohols in which more than 16% of the alcohol mixture is 2-ethylundecanol. In one embodiment, the composition can comprise a mixture of C8 - C36 alcohols in which more than 18% of the alcohol mixture is 2-ethylundecanol. In one embodiment, the composition can comprise a mixture of C8 - C36 alcohols in which more than 20% of the alcohol mixture is 2-ethylundecanol.

[0086] The above composition contains a mixture of C8-C36 alcohols, less than 60% of the mixture of C8-C36 alcohols is a straight-chain alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, more than 8% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol, the alcohol mixture contains about 90% or more of C15 alcohol (i.e., pentadecanol), less than 60% of the alcohol mixture is straight-chain 1-pentadecanol, more than 25% of the alcohol mixture is 2-methyltetradecanol, and more than 8% of the alcohol mixture can be 2-ethyltridecanol. In one embodiment, the above composition can contain a mixture of C8-C36 alcohols in which more than 10% of the alcohol mixture is 2-ethyltridecanol. In one embodiment, the above composition can contain a mixture of C8-C36 alcohols in which more than 12% of the alcohol mixture is 2-ethyltridecanol. In one embodiment, the above composition can contain a mixture of C8-C36 alcohols in which more than 14% of the alcohol mixture is 2-ethyltridecanol. In one embodiment, the above composition can contain a mixture of C8-C36 alcohols in which more than 16% of the alcohol mixture is 2-ethyltridecanol. In one embodiment, the above composition can contain a mixture of C8-C36 alcohols in which more than 18% of the alcohol mixture is 2-ethyltridecanol. In one embodiment, the above composition can contain a mixture of C8-C36 alcohols in which more than 20% of the alcohol mixture is 2-ethyltridecanol.

[0087] The composition contains a mixture of C8-C36 aldehydes, less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes can be a 2-ethyl branched aldehyde. In one embodiment, the composition can contain a mixture of C8-C36 aldehydes in which more than 10% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can contain a mixture of C8-C36 aldehydes in which more than 12% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can contain a mixture of C8-C36 aldehydes in which more than 14% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can contain a mixture of C8-C36 aldehydes in which more than 16% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can contain a mixture of C8-C36 aldehydes in which more than 18% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can contain a mixture of C8-C36 aldehydes in which more than 20% of the aldehydes are 2-ethyl branched aldehydes.

[0088] In one embodiment, the composition comprises a mixture of C8-C36 aldehydes, less than 50% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 30% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes can be a 2-ethyl branched aldehyde. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 10% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 12% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 14% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 16% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 18% of the aldehydes are 2-ethyl branched aldehydes. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 20% of the aldehydes are 2-ethyl branched aldehydes.

[0089] In one embodiment, the composition comprises a mixture of C8-C36 aldehydes, less than 60% of the mixture of C8-C36 aldehydes is a straight-chain aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde, the aldehyde mixture comprises about 90% or more of C13 aldehyde (i.e., tridecanal), less than 60% of the aldehyde mixture is straight-chain 1-tridecanal, more than 25% of the aldehyde mixture is 2-methyldodecanal, and more than 8% of the aldehyde mixture can be 2-ethylundecanal. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 10% of the aldehyde mixture is 2-ethylundecanal. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 12% of the aldehyde mixture is 2-ethylundecanal. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 14% of the aldehyde mixture is 2-ethylundecanal. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 16% of the aldehyde mixture is 2-ethylundecanal. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 18% of the aldehyde mixture is 2-ethylundecanal. In one embodiment, the composition can comprise a mixture of C8-C36 aldehydes in which more than 20% of the aldehyde mixture is 2-ethylundecanal.

[0090] In one embodiment, the composition comprises a mixture of C8-C36 aldehydes, less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde, the aldehyde mixture comprises about 90% or more of C15 aldehyde (i.e., pentadecanal), less than 60% of the aldehyde mixture is linear 1-pentadecanal, more than 25% of the aldehyde mixture is 2-methyltetradecanal, and more than 8% of the aldehyde mixture can be 2-ethyltridecanal. In one embodiment, the composition may comprise a mixture of C8-C36 aldehydes in which more than 10% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, the composition may comprise a mixture of C8-C36 aldehydes in which more than 12% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, the composition may comprise a mixture of C8-C36 aldehydes in which more than 14% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, the composition may comprise a mixture of C8-C36 aldehydes in which more than 16% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, the composition may comprise a mixture of C8-C36 aldehydes in which more than 18% of the aldehyde mixture is 2-ethyltridecanal. In one embodiment, the composition may comprise a mixture of C8-C36 aldehydes in which more than 20% of the aldehyde mixture is 2-ethyltridecanal.

[0091] Less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. Reacting the mixture of C8-C36 aldehydes with an amine and hydrogen to produce a mixture of C8-C36 amines in which less than 60% of the amine is a linear amine, more than 25% of the amine is a 2-methyl branched amine, and more than 8% of the amine is a 2-ethyl branched amine, and producing an amine composition. There is provided a produced composition manufactured as a product of a method comprising these steps. The produced composition can be produced by a reaction step in which the amine to be reacted is ammonia and the produced amine composition is a mixture of primary amines. The produced composition can be produced by a reaction step in which the amine to be reacted is a primary amine and the produced amine composition is a mixture of secondary amines. The produced composition can be produced by a reaction step in which the amine to be reacted is a secondary amine and the produced amine composition is a mixture of tertiary amines.

[0092] Less than 60% of the C8-C36 aldehyde mixture is a linear aldehyde, more than 25% of the C8-C36 aldehyde mixture is a 2-methyl branched aldehyde, and more than 8% of the C8-C36 aldehyde mixture is a 2-ethyl branched aldehyde. Reacting the C8-C36 aldehyde mixture with an amine and hydrogen to produce a C8-C36 amine mixture in which less than 60% of the amine is a linear amine, more than 25% of the amine is a 2-methyl branched amine, and more than 8% of the amine is a 2-ethyl branched amine; producing an amine composition in which less than 60% of the amine is a linear amine, more than 25% of the amine is a 2-methyl branched amine, and more than 8% of the amine is a 2-ethyl branched amine; and reacting the amine composition with oxygen or another oxidizing agent to produce an amine oxide mixture comprising a C8-C36 amine oxide mixture in which less than 60% of the amine oxide is a linear amine oxide, more than 25% of the amine oxide is a 2-methyl branched amine oxide, and more than 8% of the amine oxide is a 2-ethyl branched amine oxide. A produced amine oxide composition produced as a product of a method is provided. In one embodiment, the method can produce at least one amine oxide, or a plurality of amine oxides, each of which is a surfactant. In one embodiment, the amine oxide mixture produced by the method comprises a surfactant. In one embodiment, the amine oxide mixture produced by the method is a surfactant composition.

[0093] Less than 60% of the mixture of C8-C36 aldehydes is a straight-chain aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. Reacting the mixture of C8-C36 aldehydes with oxygen or another oxidizing agent to produce a mixture of C8-C36 carboxylic acids in which less than 60% of the carboxylic acids is a straight-chain carboxylic acid, more than 25% of the carboxylic acids is a 2-methyl branched carboxylic acid, and more than 8% of the carboxylic acids is a 2-ethyl branched carboxylic acid, and a step of producing a produced carboxylic acid composition. A produced carboxylic acid composition produced as a product of a method including the above is provided. In one embodiment, the carboxylic acid produced by this method is a corrosion inhibitor. In one embodiment, the produced ester composition produced by this method is a lubricant or a lubricant additive. In one embodiment, the produced ester composition produced by this method is a plasticizer.

[0094] In one embodiment, less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. Reacting the mixture of C8-C36 aldehydes with oxygen or another oxidizing agent to produce a mixture of C8-C36 carboxylic acids in which less than 60% of the carboxylic acids are linear carboxylic acids, more than 25% of the carboxylic acids are 2-methyl branched carboxylic acids, and more than 8% of the carboxylic acids are 2-ethyl branched carboxylic acids; and producing a produced carboxylic acid composition. As a product of the method including these steps, the produced carboxylic acid composition can be manufactured. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 alcohols with a compound having one or more carboxylic acid functional groups. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 alcohols with a monocarboxylic acid, and the produced ester composition is a mixture of monoesters. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 alcohols with a dicarboxylic acid, and the produced ester composition is a mixture of diesters. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 alcohols with a polyacid, and the produced ester composition is a mixture of polyesters. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 carboxylic acids with a compound having one or more alcohol functional groups. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 carboxylic acids with a monoalcohol, and the produced ester composition is a mixture of monoesters. In one embodiment, the produced ester composition includes ester products formed from the reaction of a mixture of C8-C36 carboxylic acids with a diol (glycol), and the produced ester composition is a mixture of diesters.In one embodiment, the resulting ester composition includes ester products formed from the reaction of a mixture of C8-C36 carboxylic acids with a polyol, and the resulting ester composition is a mixture of polyesters.

[0095] (ester)

[0096] The ester compounds disclosed herein can be produced by the reaction of a carboxylic acid with a compound containing one or more alcohol functional groups. These ester compounds have industrial applications such as, for example, lubricants for automobiles, lubricants for aircraft, and lubricants for industrial machinery. These esters can be produced from an alcohol having a plurality of alcohol functional groups such as trimethylolpropane, trimethylolethane, pentaerythritol, dipentaerythritol, neopentyl glycol, etc. and a carboxylic acid, and are also referred to as polyol esters. These polyol esters are widely used as lubricants that exhibit excellent performance in high-temperature applications.

[0097] In one embodiment, less than 60% of the mixture of C8-C36 carboxylic acids is a linear carboxylic acid, more than 25% of the mixture of C8-C36 carboxylic acids is a 2-methyl branched carboxylic acid, and more than 8% of the mixture of C8-C36 carboxylic acids is a 2-ethyl branched carboxylic acid. Reacting a mixture of C8-C36 carboxylic acids with at least one compound having at least one alcohol functional group, and producing a resulting ester composition. As a product of the method including these steps, the resulting ester composition can be manufactured. In one embodiment, the at least one compound includes a monoalcohol, and the resulting ester composition includes a mixture of monoesters. In one embodiment, the at least one compound includes a diol (glycol), and the resulting ester composition includes a mixture of a plurality of diesters. In one embodiment, the at least one compound includes a polyol, and the resulting ester composition includes a mixture of polyester compounds (polyol esters). In one embodiment, the polyol includes at least one of trimethylolpropane, trimethylolethane, pentaerythritol, and dipentaerythritol. In one embodiment, more than 12% of the mixture of C8-C36 carboxylic acids is a 2-ethyl branched carboxylic acid. In one embodiment, more than 16% of the mixture of C8-C36 carboxylic acids is a 2-ethyl branched carboxylic acid.

[0098] There is provided an ester composition produced by a method comprising reacting a mixture of C8-C36 alcohols, in which less than 60% of the mixture of C8-C36 alcohols is a straight-chain alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, and more than 8% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol, with a compound having one or more carboxylic acid functional groups. The ester composition produced by this method may be such that the compound having one or more carboxylic acid functional groups is a monocarboxylic acid and the ester composition produced is a mixture of monoesters. The ester composition produced by this method may be such that the compound having one or more carboxylic acid functional groups is a dicarboxylic acid and the ester composition produced is a mixture of diesters. The ester composition produced by this method may be such that the compound having one or more carboxylic acid functional groups is a polyacid and the ester composition produced is a mixture of polyesters.

[0099] Less than 60% of the mixture of C8-C36 aldehydes is a linear aldehyde, more than 25% of the mixture of C8-C36 aldehydes is a 2-methyl branched aldehyde, and more than 8% of the mixture of C8-C36 aldehydes is a 2-ethyl branched aldehyde. Reacting the mixture of C8-C36 aldehydes with oxygen or another oxidizing agent to produce a mixture of C8-C36 carboxylic acids in which less than 60% of the carboxylic acids are linear carboxylic acids, more than 25% of the carboxylic acids are 2-methyl branched carboxylic acids, and more than 8% of the carboxylic acids are 2-ethyl branched carboxylic acids; producing a produced carboxylic acid composition; and reacting the produced carboxylic acid composition with a compound having one or more alcohol functional groups to produce a produced ester composition. There is provided a produced ester composition produced by a method comprising: The produced ester composition of the present method may be such that the compound having one or more alcohol functional groups is a monoalcohol and the produced ester composition is a mixture of monoesters. The produced ester composition of the present method may be such that the compound having one or more alcohol functional groups is a diol (glycol) and the produced ester composition is a mixture of diesters. The produced ester composition of the present method may be such that the compound having one or more alcohol functional groups is a polyol and the produced ester composition is a mixture of polyesters. In one embodiment, the produced ester composition produced by the present method is a lubricant or a lubricant additive. In one embodiment, the produced ester composition produced by the present method is a plasticizer.

[0100] (alkyl sulfate)

[0101] The alkyl sulfates disclosed herein (also referred to as alcohol sulfates) are primary anionic surfactants. These surfactants can be produced by sulfating an alcohol compound. In some embodiments, these alkyl sulfates can be used in detergent applications such as laundry detergents, dishwashing detergents, hand washing soaps, shampoos, shower gels, and household cleaners. In some embodiments, these alkyl sulfates can also be used in industrial cleaners such as floor cleaners, car wash agents, and engine degreasers. These alkyl sulfates provide excellent foaming, wetting, and detergency properties not only in household and industrial cleaners but also in personal care products. Other industrial uses of alkyl sulfates include use in oilfield drilling fluids and enhanced oil recovery applications.

[0102] In one embodiment, a method includes reacting a mixture of C8-C36 alcohols, wherein less than 60% of the mixture of C8-C36 alcohols is a linear alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, and more than 8% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol, with a sulfating agent, and producing a resulting alkyl sulfate composition. The resulting alkyl sulfate composition can be produced as a product of the method. In one embodiment, the alkyl sulfate mixture includes a surfactant composition. In one embodiment, more than 10% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 12% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 14% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 16% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 18% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 20% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol.

[0103] In one embodiment, the produced alkyl sulfate composition may include a mixture of C8-C36 alcohol sulfates formed from the reaction of a mixture of C8-C36 alcohols with a sulfating agent, wherein less than 60% of the alcohol sulfates are linear alcohol sulfates, more than 25% of the alkyl sulfates are 2-methyl branched alkyl sulfates, and more than 8% of the alkyl sulfates are 2-ethyl branched alkyl sulfates. In one embodiment, the alkyl sulfate composition includes a surfactant. In one embodiment, the alkyl sulfate mixture is a surfactant composition. In one embodiment, at least one of the produced alkyl sulfates is a surfactant.

[0104] A produced alkyl sulfate composition is provided that is produced by a method comprising reacting a mixture of C8-C36 alcohols, wherein less than 60% of the mixture of C8-C36 alcohols are linear alcohols, more than 25% of the mixture of C8-C36 alcohols are 2-methyl branched alcohols, and more than 8% of the mixture of C8-C36 alcohols are 2-ethyl branched alcohols, with a sulfating agent to produce a mixture of C8-C36 alcohol sulfates, wherein less than 60% of the alcohol sulfates are linear alcohol sulfates, more than 25% of the alkyl sulfates are 2-methyl branched alkyl sulfates, and more than 8% of the alkyl sulfates are 2-ethyl branched alkyl sulfates. In one embodiment, the method can produce at least one alkyl sulfate, or a plurality of alkyl sulfates, each of which is a surfactant. The produced alkyl sulfate composition of the method may be such that the alkyl sulfate mixture includes a surfactant. The produced alkyl sulfate composition of the method may be such that the alkyl sulfate mixture is a surfactant composition.

[0105] (Alcohol alkoxylate)

[0106] The alcohol alkoxylates disclosed herein can be used as nonionic surfactants. These alcohol alkoxylates can be produced by alkoxylating an alcohol compound with an oxide compound such as ethylene oxide, propylene oxide, or butylene oxide. In embodiments where ethylene oxide is used as a reactant, these products are also referred to as alcohol ethoxylates or ethoxylated alcohols. In embodiments where propylene oxide is used as a reactant, these products are also referred to as alcohol propoxylates or propoxylated alcohols. In some embodiments, these alcohol alkoxylate surfactants can be used in detergent applications such as laundry detergents, dishwashing detergents, and household cleaners. These alcohol alkoxylates can also be used in industrial cleaners such as floor cleaners, car wash agents, and engine degreasers. In some embodiments, these alkyl alkoxylates can be further reacted by sulfation to produce alcohol alkoxylate sulfates (alkyl ether sulfates). In some embodiments, these alcohol alkoxylate sulfates can be used as anionic surfactants.

[0107] In one embodiment, less than 60% of the mixture of C8-C36 alcohols is a linear alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, and more than 8% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. Reacting a mixture of C8-C36 alcohols with an alkoxylating agent and producing a resulting alcohol alkoxylate composition. As a product of the method including these steps, a resulting alcohol alkoxylate composition can be produced. In one embodiment, the alkoxylating agent includes at least one of ethylene oxide, propylene oxide, and butylene oxide. In one embodiment, the alcohol alkoxylate mixture includes a surfactant. In one embodiment, more than 12% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 16% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, more than 20% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. In one embodiment, the method further includes reacting the resulting alcohol alkoxylate composition with a sulfating agent to produce a resulting alcohol alkoxylate sulfate composition (alkyl ether sulfate composition). In one embodiment, the resulting alcohol alkoxylate sulfate composition (alkyl ether sulfate composition) includes a surfactant.

[0108] In one embodiment, a mixture of C8 - C36 alcohols is reacted with an alkoxylating agent to produce a mixture of C8 - C36 alcohol alkoxylates, wherein less than 60% of the alcohol alkoxylates are linear alcohol alkoxylates, more than 25% of the alcohol alkoxylates are 2 - methyl - branched alcohol alkoxylates, and more than 8% of the alcohol alkoxylates are 2 - ethyl - branched alcohol alkoxylates, and a step of producing a resulting alcohol alkoxylate composition, and a step of producing a resulting alcohol alkoxylate composition. The resulting alcohol alkoxylate composition can be manufactured by a method including these steps. In one embodiment, the alcohol alkoxylate composition contains a surfactant. In one embodiment, the alcohol alkoxylate mixture is a surfactant composition. In one embodiment, at least one of the resulting alcohol alkoxylates is a surfactant. In one embodiment, the alkoxylating agent is ethylene oxide, propylene oxide, butylene oxide, or an epoxide mixture containing ethylene oxide, propylene oxide, or butylene oxide.

[0109] Less than 60% of the mixture of C8-C36 alcohols is a linear alcohol, more than 25% of the mixture of C8-C36 alcohols is a 2-methyl branched alcohol, and more than 8% of the mixture of C8-C36 alcohols is a 2-ethyl branched alcohol. Reacting the mixture of C8-C36 alcohols with an alkoxylating agent to produce a resulting alcohol alkoxylate composition comprising a mixture of C8-C36 alcohol alkoxylates in which less than 60% of the alcohol alkoxylate is a linear alcohol alkoxylate, more than 25% of the alcohol alkoxylate is a 2-methyl branched alcohol alkoxylate, and more than 8% of the alcohol alkoxylate is a 2-ethyl branched alcohol alkoxylate. A resulting alcohol alkoxylate composition produced by a method comprising the step of producing is provided. In one embodiment, the method can produce at least one alcohol alkoxylate, or a plurality of alcohol alkoxylates, each of which is a surfactant. The resulting alcohol alkoxylate composition produced by the method may comprise an alcohol alkoxylate mixture containing a surfactant. The resulting alcohol alkoxylate composition produced by the method can be a surfactant composition. The resulting alcohol alkoxylate composition produced by the method may be such that the alkoxylating agent can be ethylene oxide, propylene oxide, butylene oxide, or an epoxide mixture containing ethylene oxide, propylene oxide, and butylene oxide.

[0110] (Alcohol alkoxylate sulfate)

[0111] In one embodiment, a mixture of C8-C36 alcohol alkoxylates is reacted with a sulfating agent to produce a mixture of C8-C36 alcohol alkoxylate sulfates, wherein less than 60% of the alcohol alkoxylate sulfates are linear alcohol alkoxylate sulfates, more than 25% of the alcohol alkoxylate sulfates are 2-methyl branched alcohol alkoxylate sulfates, and more than 8% of the alcohol alkoxylate sulfates are 2-ethyl branched alcohol alkoxylate sulfates, and a step of producing a resulting alcohol alkoxylate sulfate (i.e., alkyl ether sulfate) composition. As a product of the method including the above steps, a resulting alcohol alkoxylate sulfate (i.e., alkyl ether sulfate) composition can be manufactured. In one embodiment, the alcohol alkoxylate sulfate composition contains a surfactant. In one embodiment, the alcohol alkoxylate sulfate mixture is a surfactant composition. In one embodiment, at least one of the resulting alcohol alkoxylate sulfates is a surfactant.

[0112] Less than 60% of the mixture of C8 - C36 alcohols is a linear alcohol, more than 25% of the mixture of C8 - C36 alcohols is a 2 - methyl - branched alcohol, and more than 8% of the mixture of C8 - C36 alcohols is a 2 - ethyl - branched alcohol. React the mixture of C8 - C36 alcohols with an alkoxylating agent to produce an alcohol alkoxylate composition containing a mixture of C8 - C36 alcohol alkoxylates, where less than 60% of the alcohol alkoxylate is a linear alcohol alkoxylate, more than 25% of the alcohol alkoxylate is a 2 - methyl - branched alcohol alkoxylate, and more than 8% of the alcohol alkoxylate is a 2 - ethyl - branched alcohol alkoxylate. React the resulting alcohol alkoxylate composition with a sulfating agent to produce a resulting alcohol alkoxylate sulfate (i.e., alkyl ether sulfate) where less than 60% of the alcohol alkoxylate sulfate is a linear alcohol alkoxylate sulfate, more than 25% of the alcohol alkoxylate sulfate is a 2 - methyl - branched alcohol alkoxylate sulfate, and more than 8% of the alcohol alkoxylate sulfate is a 2 - ethyl - branched alcohol alkoxylate sulfate. In one embodiment, the method can produce at least one alcohol alkoxylate sulfate (i.e., alkyl ether sulfate), or a plurality of alcohol alkoxylate sulfates (i.e., alkyl ether sulfates), each of which is a surfactant. The resulting alcohol alkoxylate sulfate (i.e., alkyl ether sulfate) produced by the method may have an alcohol alkoxylate sulfate mixture that includes a surfactant. The resulting alcohol alkoxylate sulfate (i.e., alkyl ether sulfate) produced by the method may have an alcohol alkoxylate sulfate mixture that is a surfactant composition.

[0113] A method for producing a produced aldehyde composition comprising a mixture of two or more branched aldehydes, the method comprising: providing at least two C4-C36 α-olefins having different chain lengths; providing a first catalyst; isomerizing the α-olefin mixture with the first catalyst at a first pressure in an atmosphere containing CO and H2 to produce a composition of an intermediate isomerized olefin product comprising a mixture of α-olefins and internal olefins; hydroformylating the intermediate isomerized olefin product with the first catalyst at a second pressure higher than the first pressure in an atmosphere containing CO and H2; and producing a produced aldehyde composition which is a mixture of C5-C37 branched aldehydes having at least two different chain lengths. A method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes further comprises separating the mixture of C5-C37 branched aldehydes from the first catalyst stream by a distillation process. In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the catalyst can be a rhodium catalyst. In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the catalyst can be a homogeneous rhodium catalyst. In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the catalyst can be an organometallic complex of rhodium and one organic phosphorus ligand, or an organometallic complex of rhodium and two or more organic phosphorus ligands. In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the first pressure can range from 0.01 bar (absolute pressure) to 20 bar (absolute pressure). In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the intermediate isomerized olefin product can contain at least 20 wt% of internal olefins. In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the second pressure can range from 1 bar (gauge) to 400 bar (gauge). In a method for producing a produced aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the produced branched aldehyde can be a 2-alkyl branched aldehyde.In a method for producing a resulting aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the resulting aldehyde composition may contain at least 25 wt% branched aldehyde. In a method for producing a resulting aldehyde composition comprising a mixture of C5-C37 branched aldehydes, the resulting aldehyde composition has at least two different C5-C37 chain lengths, and the method may further include separating, via a series of distillation processes, the resulting aldehyde composition comprising a mixture of at least two different C5-C37 branched aldehydes into individual purified branched aldehyde products. Each distilled purified branched aldehyde product consists essentially of a product having a single carbon chain length in the carbon number range of C5-C37.

[0114] A method for producing a mixture of two or more branched alcohols, comprising the steps of: providing at least two C4-C36 α-olefins with different chain lengths; providing a first catalyst; isomerizing the α-olefin mixture with the first catalyst at a first pressure in an atmosphere containing CO and H2 to produce a composition of an intermediate isomerized olefin product containing a mixture of α-olefins and internal olefins; hydroformylating the intermediate isomerized olefin product with the first catalyst at a second pressure higher than the first pressure in an atmosphere containing CO and H2 to produce a mixture of at least two different C5-C37 chain length branched aldehydes; separating the mixture of C5-C37 branched aldehydes from the rhodium-containing catalyst stream via a distillation process; hydrogenating the mixture of C5-C37 branched aldehydes at an elevated hydrogen pressure in the presence of hydrogen and a hydrogenation catalyst; and producing a product which is a mixture of branched alcohols having at least two different carbon chain lengths in the carbon number range of C5-C37 (also represented as two different C5-C37 chain lengths). In the method for producing a mixture of C5-C37 branched alcohols, the catalyst can be a rhodium catalyst. In the method for producing a mixture of C5-C37 branched alcohols, the catalyst can be a homogeneous rhodium catalyst. In the method for producing a mixture of C5-C37 branched alcohols, the catalyst can be an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands. In the method for producing a mixture of C5-C37 branched alcohols, the first pressure can be in the range of 0.01 bar (absolute pressure) to 20 bar (absolute pressure). In the method for producing a mixture of C5-C37 branched alcohols, the intermediate isomerized olefin product can contain at least 20 wt% of internal olefins. In the method for producing a mixture of C5-C37 branched alcohols, the second pressure can be in the range of 1 bar (g) to 400 bar (g). In the method for producing a mixture of C5-C37 branched alcohols, the mixture of C5-C37 branched alcohols can be 2-alkyl branched alcohols.In a process for producing a mixture of C5 - C37 branched alcohols, the mixture of C5 - C37 branched alcohols can contain at least 25 wt% branched alcohol. In a process for producing a mixture of C5 - C37 branched alcohols, the mixture has at least two different C5 - C37 chain lengths, and the process may further include separating, via a series of distillation processes, a mixture of at least two C5 - C37 branched alcohols into individual purified branched alcohol products. Each distilled purified branched alcohol product consists essentially of a product having a single carbon chain length within the C5 - C37 carbon number range. A process for producing a mixture of C5 - C37 branched alcohols includes providing two α - olefins, a C12 α - olefin (i.e., 1 - dodecene) which is a first α - olefin and a C14 α - olefin (i.e., 1 - tetradecene) which is a second α - olefin, generating a mixture of branched C13 aldehyde and branched C15 aldehyde, and generating a mixture of branched C13 alcohol and branched C15 alcohol. A process for producing a mixture of C13 branched alcohols may further include separating a mixture of C13 branched alcohol and C15 branched alcohol, purifying the C13 branched alcohol product by a first distillation step, and purifying the branched C15 alcohol product by a second distillation step.

[0115] Providing a first catalyst comprising an organometallic complex having at least one of rhodium and cobalt and at least one type of organic phosphorus ligand; providing a mixture of one or more C4 - C36 linear α - olefins; providing a gas phase containing CO; isomerizing the linear α - olefin with the first catalyst at a first pressure in the presence of CO to produce an isomerized olefin; hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde. In one embodiment, the branched aldehyde can be a 2 - alkyl branched aldehyde. In one embodiment, the organic phosphorus ligand can be a phosphite ligand. In one embodiment, the organic phosphorus ligand can be a phosphite ligand which is tris(2,4 - di - t - butylphenyl) phosphite. In one embodiment, at least one type of organic phosphorus ligand may be a mixture of triphenylphosphine and tris(2,4 - di - t - butylphenyl) phosphite. In one embodiment, the method may further comprise providing a hydrogenation catalyst, providing hydrogen, and hydrogenating the branched aldehyde in the presence of the hydrogenation catalyst and hydrogen to produce a branched alcohol.

[0116] Providing a first catalyst comprising an organometallic complex having at least one of rhodium and cobalt and at least one organic phosphorus ligand; providing a mixture of one or more C4-C36 linear α-olefins; providing a gas phase containing CO; isomerizing the linear α-olefin with the first catalyst at a first pressure in the presence of CO to produce an isomerized olefin; and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde. In one embodiment, the branched aldehyde can be a 2-alkyl branched aldehyde. In one embodiment, the organic phosphorus ligand can be a phosphite ligand. In one embodiment, the organic phosphorus ligand can be a phosphite ligand that is tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the method can further have a first organic phosphorus ligand that is triphenylphosphine and a second organic phosphorus ligand that is tris(2,4-di-t-butylphenyl) phosphite. In one embodiment, the method may further include providing a hydrogenation catalyst, providing hydrogen, and hydrogenating the branched aldehyde in the presence of the hydrogenation catalyst and hydrogen to produce a branched alcohol.

[0117] (Branched surfactant) In one embodiment, a method for producing a branched surfactant includes providing CO and H2; providing a first catalyst that is an organometallic complex of rhodium and one type of organic phosphorus ligand, or an organometallic complex of rhodium and two or more types of organic phosphorus ligands; providing an α-olefin; isomerizing the α-olefin with the first catalyst at a first pressure in the presence of CO and H2 to produce an isomerized olefin; hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde; hydrogenating the branched aldehyde to produce a branched alcohol; and producing a branched surfactant from the branched alcohol. In one embodiment, the production step includes sulfating the branched alcohol to produce a branched alcohol sulfate surfactant. In one embodiment, the production step includes alkoxylating the branched alcohol to produce a branched alkoxylated alcohol surfactant. In one embodiment, the method further includes using an alkoxylating agent including at least one of ethylene oxide, propylene oxide, butylene oxide, or a mixture of ethylene oxide, propylene oxide, and butylene oxide. In one embodiment, the branched alkoxylated alcohol is sulfated to produce a branched alkoxylated alcohol sulfate surfactant. In one embodiment, the isomerization step produces a reaction product including 25 wt% or more of internal olefins. In one embodiment, the isomerization step produces a reaction product including 50 wt% or more of internal olefins. In one embodiment, the hydroformylation step produces a reaction product including 25 wt% or more of branched aldehydes. In one embodiment, the hydroformylation step produces a reaction product including 50 wt% or more of branched aldehydes. In one embodiment, the hydrogenation step produces a reaction product including 40 wt% or more of branched alcohol. In one embodiment, the hydrogenation step produces a reaction product including 50 wt% or more of branched alcohol. In one embodiment, the surfactant includes 40 wt% or more of branched surfactant. In one embodiment, the surfactant includes 50 wt% or more of branched surfactant.

[0118] In one embodiment, in the presence of a gas containing CO, at a first pressure, a first catalyst having a rhodium metal and an organic phosphorus ligand is used to isomerize C4-C36 α-olefins to produce isomerized olefins; and in the presence of a gas containing CO and H2, at a second pressure different from the first pressure, the first catalyst is used to hydroformylate the isomerized olefins to produce C5-C37 branched aldehydes; and the C5-C37 branched aldehydes are hydrogenated to produce C5-C37 branched alcohols; and a branched surfactant is produced from the C5-C37 branched alcohols. In one embodiment of the method for producing a branched surfactant, 20 wt% to 100 wt% of the isomerized olefin mixture is isomerized. In one embodiment of the method for producing a branched surfactant, 25 wt% to 100 wt% of the branched aldehyde mixture is branched. In one embodiment of the method for producing a branched surfactant, 40 wt% to 100 wt% of the branched alcohol mixture is branched. In one embodiment of the method for producing a branched surfactant, 40 wt% to 100 wt% of the branched surfactant is branched.

[0119] (Downstream product)

[0120] In one embodiment, a method for producing a branched aldehyde intermediate and / or a branched aldehyde intermediate composition includes providing a first catalyst comprising an organometallic complex having at least one of rhodium and cobalt and at least one organic phosphorus ligand; providing one or more C4-C36 linear α-olefins; providing a gas phase containing CO; isomerizing the linear α-olefins with the first catalyst at a first pressure in the presence of CO to produce isomerized olefins; and hydroformylating the isomerized olefins with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde intermediate composition.

[0121] In one embodiment, the method for producing a branched aldehyde intermediate can produce a branched product composition including at least one of a branched alcohol composition, a branched surfactant composition, a branched amine composition, a branched amine oxide composition, a branched carboxylic acid composition, a branched ester composition, a branched alkyl sulfate composition, a branched alcohol alkoxylate composition, a branched alcohol alkoxylate sulfate composition, a branched cyanohydrin composition, a branched aldol condensate composition, a branched hydrate composition, a branched hemiacetal composition, and a branched acetal composition through further reactions such as a hydrogenation reaction, a surfactant formation reaction, and other chemical derivative formation reactions.

[0122] In one embodiment, the method for producing a branched aldehyde intermediate and / or a branched aldehyde intermediate composition further includes the step of generating a branched product composition including at least one of a branched alcohol composition, a branched surfactant composition, a branched amine composition, a branched amine oxide composition, a branched carboxylic acid composition, a branched aldehyde acid composition, a branched ester composition, a branched alkyl sulfate composition, a branched alcohol alkoxylate composition, a branched alcohol alkoxylate sulfate composition, a branched cyanohydrin composition, a branched aldol condensate composition, a branched hydrate composition, a branched hemiacetal composition, and a branched acetal composition based on the reaction of the branched aldehyde intermediate composition.

[0123] In one embodiment, a method for producing a branched aldehyde intermediate and / or a branched aldehyde intermediate composition further includes the step of producing at least one of the following products containing a branched product composition: detergents, cleaning agents, shampoos, emulsifiers, creams, lotions, toothpastes, wetting agents, cosmetics, personal care products, soaps, laundry detergents, dishwashing detergents, shower gels, hair conditioners, fabric softeners, paper, oils, fragrances, fragrance components, perfumes, essential oils, organic solvents, synthetic pheromones, explosives, plastics, hand disinfectants, pharmaceuticals, flavorings and / or fixatives, catalysts, base catalysts, acid catalysts, plasticizers, flame retardants, engine oils, oil additives, insecticides, pesticides, foods, beverages, adhesives, sealants, paints, stains, coating agents, inks, nail polishes, pharmaceutical compositions, lubricants, lubricant additives, polymer additives, coating additives, antioxidants, polymers, copolymers, polymer modifiers, polyols, corrosion inhibitors, viscosity modifiers, coupling agents, thickeners, greases, fragrances, skin care products, laundry detergents, dishwashing detergents, hand washing soaps, household cleaning agents, industrial cleaning agents, floor cleaners, car wash soaps, engine degreasers, foaming agents, wetting agents, oil field drilling oils, petroleum enhanced recovery agents, surfactants, nonionic surfactants, anionic surfactants.

[0124] In one embodiment, a method for producing a branched aldehyde further includes the step of using the product composition in at least one of the processes of oil production, oil field drilling, petroleum enhanced recovery, automobile production, aircraft production, metal processing, lubricating oil production, polymer production, degreasing, cleaning, dishwashing, laundry washing, medical treatment, and coating.

[0125] In one embodiment, the method includes providing a first catalyst comprising an organometallic complex having at least one of rhodium and cobalt and at least one organic phosphorus ligand; providing one or more C4-C36 linear α-olefins; providing a gas phase containing CO; isomerizing the linear α-olefin with the first catalyst at a first pressure in the presence of CO to produce an isomerized olefin; and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde intermediate composition. Further, the method may further include reacting the branched aldehyde intermediate composition by a hydrogenation reaction, a surfactant formation reaction, and other chemical derivative formation reactions to produce a branched product composition including at least one of a branched alcohol composition, a branched surfactant composition, a branched amine composition, a branched amine oxide composition, a branched carboxylic acid composition, a branched ester composition, a branched alkyl sulfate composition, a branched alcohol alkoxylate composition, a branched alcohol alkoxylate sulfate composition, a branched cyanohydrin composition, a branched aldol condensate composition, a branched hydrate composition, a branched hemiacetal composition, and a branched acetal composition.The method may further include the step of manufacturing at least one of the following products comprising the branched product composition: detergents, cleaning agents, shampoos, emulsifiers, creams, lotions, toothpastes, wetting agents, cosmetics, personal care products, soaps, laundry detergents, dishwashing detergents, shower gels, hair conditioners, fabric softeners, paper, oils, fragrances, fragrance components, perfumes, essential oils, organic solvents, synthetic pheromones, explosives, plastics, hand disinfectants, pharmaceuticals, flavorings and / or fixatives, catalysts, base catalysts, acid catalysts, plasticizers, flame retardants, engine oils, oil additives, insecticides, pesticides, foods, beverages, adhesives, sealants, paints, stains, coating agents, inks, nail polishes, pharmaceutical compositions, lubricants, lubricant additives, polymer additives, coating additives, antioxidants, polymers, copolymers, polymer modifiers, polyols, corrosion inhibitors, viscosity modifiers, coupling agents, thickeners, greases, fragrances, skin care products, laundry detergents, dishwashing detergents, hand soaps, household cleaning agents, industrial cleaning agents, floor cleaners, car soaps, engine degreasers, foaming agents, wetting agents, oilfield drilling oils, petroleum enhanced recovery agents, surfactants, nonionic surfactants, anionic surfactants. The method may further include the step of using the branched product composition in at least one of the processes of petroleum production, oilfield drilling, petroleum enhanced recovery, automotive production, aircraft production, metalworking, lubricating oil manufacturing, polymer manufacturing, degreasing, cleaning, dishwashing, laundry washing, medical treatment, and coating.

[0126] Certain aspects and embodiments of the present invention solve the above-described problems and significantly advance the art of branched compounds and the production and manufacturing techniques of branched compounds. The present invention can be more fully understood from the detailed description and the following accompanying drawings.

Brief Description of the Drawings

[0127]

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DETAILED DESCRIPTION OF THE INVENTION

[0128] The same reference numerals in one figure correspond to the same reference numerals in another figure.

[0129] In one embodiment, a two-step process for producing a branched aldehyde product that is 25% to 98% or more branched and is produced from an α-olefin feedstock is disclosed. Further, the two-step process disclosed herein uses an organometallic complex of rhodium and at least one organic phosphorus ligand in both the first-step isomerization reaction step and the second-step hydroformylation reaction step. Also, the two-step process disclosed herein may use an organometallic complex of cobalt and at least one organic phosphorus ligand in both the first-step isomerization reaction step and the second-step hydroformylation reaction step. Additionally, the two-step process disclosed herein may use a mixed organometallic complex containing cobalt, rhodium, and at least one organic phosphorus ligand in both the first-step isomerization reaction step and the second-step hydroformylation reaction step.

[0130] Numerical values and ranges in this specification have tolerances and are also intended to account for variations in design and manufacturing, unless otherwise specified. Thus, a numerical value can include values “about” that numerical value. For example, the value X is intended to be understood as “about X”. Similarly, a range from Y to Z is intended to be understood as being within the range “about Y to about Z”. Unless otherwise specified, the significant figures disclosed for a numerical value are not intended to be strict limiting values for that numerical value. Variations and tolerances are inherent in mechanical design, and the numerical values disclosed herein are intended to be interpreted to allow for such factors (as a non-limiting example, ±10% of the given value). Similarly, the claims are to be broadly interpreted with respect to numerical values and ranges.

[0131] All numerical ranges shown in this specification include all narrower numerical ranges that are included within that broader numerical range, as if such narrower numerical ranges were all explicitly recited herein. With respect to ranges and endpoints, all maximum numerical limits shown in this specification include all lower numerical limits, as if such lower numerical limits were all explicitly recited herein. All minimum numerical limits shown in this specification include all higher numerical limits, as if such higher numerical limits were all explicitly recited herein.

[0132] As used herein, the term "reactor" means one or more physical reactors used individually or in combination to achieve a reactive step in a chemical process. The terms "reaction step" and "reactive step" are used synonymously. A "reactor" may be a single vessel or optionally a plurality of vessels. A "reactor" may optionally be configured such that the reaction step occurs in one or more reaction vessels. When there are multiple reaction vessels, these reaction vessels can operate in series, parallel, or any combination thereof. The term "reactor" is a unit operation that performs a chemical reaction processing step and is also referred to as a reaction step or a reactive step.

[0133] For example, as shown in FIGS. 1-6, the representation and / or description of a reactor should not be construed as being limited to a single physical reactor in particular. Optionally, a single physical reactor may be used to achieve the reaction step, or alternatively, a plurality of physical reactors may be used to achieve the reaction step. Here, the term "reactor" should be construed as actually meaning a reaction step that can be carried out in one or more reactors operating in series, parallel, or any combination thereof. Therefore, an "isomerization reactor" should be construed as meaning an isomerization step (isomerization reaction step) that occurs in one or more reactors operating in series, parallel, or any combination thereof. Similarly, a "hydroformylation reactor" should be construed as meaning a hydroformylation step (hydroformylation reaction step) that occurs in one or more reactors operating in series, parallel, or any combination thereof. Furthermore, a "hydrogenation reactor" should be construed as meaning a hydrogenation step (hydrogenation reaction step) that occurs in one or more reactors operating in series, parallel, or any combination thereof.

[0134] Unless otherwise specified, the temperatures shown herein are expressed in degrees Celsius (°C).

[0135] Unless otherwise specified, the pressures shown in this specification are expressed in bar(g), i.e., barg. Here, 0 bar(g) is atmospheric pressure, e.g., 14.70 psia (or 0 psig).

[0136] Pressures can also be expressed in absolute pressure, denoted as bar(a) or bar(absolute pressure).

[0137] Pressures can also be expressed in millibar units, denoted as mbar, mbar(a), mbar absolute pressure, or mbar(absolute pressure). These each represent the pressure expressed in units of absolute millibar and are all equivalent and interchangeably used.

[0138] Unless otherwise specified, the percentages of the compositions shown in this specification are by weight and are disclosed as weight% (wt%).

[0139] Alternatively, in this specification, concentrations are expressed in parts per million (ppm).

[0140] In this specification, the number of carbon atoms in a molecule is represented by attaching an integer representing the number of carbon atoms of that molecule after the capital letter "C". For example, "C12" is a molecule with 12 carbon atoms (e.g., 1-dodecene).

[0141] In this specification, the term "olefin" is used synonymously with the term "alkene", which means a molecule containing a carbon-carbon double bond.

[0142] In this specification, "linear" is defined as a molecule, compound, or chemical structure without branches along the carbon skeleton (i.e., straight-chain).

[0143] In this specification, "branched" is defined as a molecule, compound, or chemical structure to which one or more alkyl groups are attached along the carbon skeleton. A "branched" molecule is an isomer of a linear (i.e., straight-chain) molecule having the same number of carbon atoms.

[0144] In this specification, the term "percent linear" is defined to mean, in addition to its ordinary and customary meaning, the weight percent of linear molecules in a composition.

[0145] In this specification, the term "percent branched" is defined to mean, in addition to its ordinary and customary meaning, the weight percent of branched molecules in a composition. The term "percent branching" is used synonymously with "percent branched" and has the same meaning. As an example, in the case of an aldehyde composition, the "percent branched" (also referred to as "percent branching (%)") of the aldehyde means the weight percent of branched aldehyde isomers relative to the total weight percent of aldehydes present, as follows. Percent branched (%) = 100 * (weight % of branched aldehyde) ÷ (weight % of branched aldehyde + weight % of linear aldehyde).

[0146] As an example, a branched C6 aldehyde composition contains 25 wt% of 1 - hexanal (linear molecule) 40 wt% of 2 - methylpentanal (branched molecule) 35 wt% of 2 - ethylbutanal (branched molecule) and has a percent branched of 75%.

[0147] As another example, a branched C13 aldehyde composition contains 25 wt% of 1 - tridecanal (linear molecule) 40 wt% of 2 - methyldodecanal (branched molecule) 20 wt% of 2 - ethylundecanal (branched molecule) 15 wt% of 2 - propyldecanal (branched molecule) and has a percent branched of 75%.

[0148] In this example, the branching of the C13 aldehyde occurs at the second carbon position from the aldehyde carbon and is defined as "2 - alkyl" branching.

[0149] Here, the ratio of "2-methyl branching" is defined as the weight % of the compound having a methyl group branch at the 2-position carbon. In this example of the C13 aldehyde, the ratio of the 2-methyl branched aldehyde = 40 wt% (i.e., the weight % of 2-methyldodecanal).

[0150] Here, the ratio of "2-ethyl branching" is defined as the weight % of the compound having an ethyl group branch at the 2-position carbon. In this example of the C13 aldehyde, the ratio of the 2-ethyl branched aldehyde = 20 wt% (i.e., the weight % of 2-ethylundecanal).

[0151] Unless otherwise specified, the branching ratio and linear ratio shown here are weight % (wt%) calculated based on the weights of the reactants and products excluding the non-participating compounds.

[0152] In this specification, the term "isomerization rate" is defined to mean, in addition to its ordinary and customary meaning, the weight % of olefin molecules in which the olefin has isomerized from the α-position to an internal olefin position. Specifically, the "isomerization rate" means the weight % of internal olefins in the olefin composition and is as follows.

[0153] 100 * (weight % of internal olefins) ÷ (weight % of α-olefins + weight % of internal olefins).

[0154] As an example, a composition obtained by isomerizing C12 α-olefin contains 25 wt% of 1-dodecene (α-olefin) 40 wt% of 2-dodecene (internal olefin) 35 wt% of 3-dodecene (internal olefin) and has an isomerization rate = 75%.

[0155] Unless otherwise specified, the term "internal olefin" shown in this specification means an olefin having a double bond at a position other than the α-position.

[0156] Unless otherwise specified, the isomerization rates shown herein are weight percentages (wt%) calculated based on the weights of the reactants and products excluding non-participating compounds.

[0157] In one embodiment, the branched alcohol can be produced by a process having the following method steps. 1) Provide a C4 - C36 α-olefin. 2) Provide a homogeneous rhodium organic phosphorus ligand catalyst. 3) Catalyze the isomerization of the C4 - C36 olefin with a rhodium catalyst at a pressure of 0.01 bar (absolute pressure) to 20 bar (absolute pressure) in a CO / H2 atmosphere. 4) Produce a composition of an intermediate isomerized olefin product containing at least 20 wt% of internal (non-α) olefins. 5) Catalyze the hydroformylation of the intermediate isomerized olefin product with a rhodium catalyst at a pressure of 1 bar(g) to 400 bar(g) in a CO / H2 atmosphere. 6) Produce a composition of a branched aldehyde product containing at least 25 wt% of branched aldehydes. 7) Separate the branched aldehyde product from the rhodium-containing catalyst stream by a distillation process. 8) Hydrogenate the branched aldehyde at an elevated hydrogen pressure in the presence of a hydrogenation catalyst. 9) Produce a composition of a branched alcohol product containing at least 40 wt% of branched alcohols.

[0158] In one embodiment, the branched alcohol can be produced by a process having the following method steps. 1) Provide a C4 - C36 α-olefin. 2) Provide a homogeneous rhodium organic phosphorus ligand catalyst. 3) Catalyze the isomerization of the C4 - C36 olefin with a rhodium catalyst at a pressure of 0.01 bar (absolute pressure) to 20 bar (absolute pressure) and a CO / H2 molar ratio in the range of 10:1 to 1:10 in a CO / H2 atmosphere. 4) Produce a composition of an intermediate isomerized olefin product containing at least 20 wt% of internal (non-α) olefins. 5) Under a CO / H₂ atmosphere, at a pressure of 1 bar(g) to 400 bar(g) and a CO / H₂ molar ratio in the range of 10:1 to 1:10, it is catalyzed by a rhodium catalyst to hydroformylate the intermediate isomerized olefin product. 6) A composition of a branched aldehyde product containing at least 25 wt% of a branched aldehyde is produced. 7) The branched aldehyde product is separated from the rhodium-containing catalyst stream by a distillation process. 8) In the presence of a hydrogenation catalyst, the branched aldehyde is hydrogenated at an elevated hydrogen pressure. 9) A composition of a branched alcohol product containing at least 40 wt% of a branched alcohol is produced.

[0159] Figure 1 shows one embodiment of a chemical manufacturing process having an isomerization reactor and a hydroformylation reactor.

[0160] Figure 1 shows a two-step process in which a stream 1 containing an α-olefin is fed to an isomerization reactor 100 to produce a stream 2 containing an isomerized olefin, and the stream 2 is fed to a hydroformylation reactor 200 to produce a stream 3 containing a branched aldehyde.

[0161] (Catalyst Specifications and Composition)

[0162] In one embodiment, the same catalyst can be used in each of the first and second steps of the two-step process. In one embodiment, the same catalyst can be used in the isomerization reactor 100 and the hydroformylation reactor 200.

[0163] In one embodiment, the isomerization reaction and the hydroformylation reaction can be catalyzed by a rhodium organic phosphorus ligand catalyst. The organic phosphorus ligand catalyst can be activated by the presence of CO. In one embodiment, the isomerization reaction and the hydroformylation reaction can be catalyzed by a cobalt organic phosphorus ligand catalyst. In one embodiment, the isomerization reaction and the hydroformylation reaction can be catalyzed by a cobalt-rhodium organic phosphorus ligand catalyst.

[0164] In one embodiment, a rhodium(-PPh3) catalyst system can be used as the catalyst.

[0165] For example, a triphenylphosphine rhodium (-PPh3) catalyst system can exist in different states and / or configurations so as to be used in different reactions such as isomerization reactions and hydroformylation reactions. As shown in Sequence 1 below, the left end shows that in the absence of CO, the three bonded -PPh3 groups "block" the catalytic active site, indicating that the catalyst is in an inactive state. However, when CO is added, the -PPh3 groups on rhodium are gradually replaced by CO groups, "releasing" and activating the catalyst, enabling it to catalyze the isomerization reaction and hydroformylation reaction of the embodiments disclosed herein. (Sequence 1: Activation sequence of triphenylphosphine rhodium)

Chemical formula

[0166] (Composition of the catalyst)

[0167] In one embodiment, the molar ratio of phosphorus ("P") to rhodium ("Rh") in the isomerization reaction or hydroformylation reaction (P:Rh) ranges from 1:1 to 1000:1, or from 3:1 to 200:1, or from 5:1 to 50:1. As non-limiting examples, it can be 1:1, 3:1, 5:1, 10:1, 20:1, 30:1, 40:1, 50:1, 100:1, 200:1, 500:1, or 1000:1.

[0168] In one embodiment, the concentration of Rh in the isomerization reaction or hydroformylation reaction ranges from 1 to 10000 ppm, from 10 to 1000 ppm, or from 20 to 200 ppm. As non-limiting examples, it can be 1 ppm, 20 ppm, 50 ppm, 100 ppm, 200 ppm, 300 ppm, 400 ppm, 500 ppm, 1000 ppm, 2000 ppm, 5000 ppm, 7500 ppm, or 10000 ppm.

[0169] In one embodiment, the catalyst used in the isomerization reaction and the hydroformylation reaction is an organometallic rhodium ligand complex composed of Rh(CO)2ACAC (rhodium(I) dicarbonyl acetylacetonate) and tris(2,4-di-t-butylphenyl) phosphite ligand.

[0170] (Isomerization)

[0171] The first stage occurs in the isomerization reactor 100, and the feed of stream 1 to the isomerization reactor 100 may have a composition including the following. · C4 - C36 α-olefin (or a mixture thereof), · Rhodium catalyst A, · Carbon monoxide (CO), and · Hydrogen.

[0172] Optionally, stream 1 may contain a high-boiling inert solvent, such as poly-α-olefin.

[0173] The rhodium catalyst A is an organometallic complex of rhodium and at least one organic phosphorus ligand. The isomerization reaction can proceed at a pressure of 0.01 bar (absolute pressure) to 20 bar (absolute pressure) and a temperature of 30 to 300 °C, for example 90 °C, in the presence of CO and H2. The isomerization reaction conditions can be described as proceeding at a pressure of 0.01 bar (absolute pressure) to 20 bar (absolute pressure) and a temperature of 30 to 300 °C, for example 90 °C, in a CO / H2 atmosphere. The isomerization reaction can proceed in the range of a CO:H2 molar ratio of 10:1 to 1:10.

[0174] The isomerization process can be processed in a batch or continuous mode. All reactions and unit operations disclosed in this specification can be processed in a batch or continuous mode.

[0175] In one embodiment, the catalyst used in the isomerization reaction and the hydroformylation reaction is a rhodium ligand complex composed of Rh(CO)2ACAC (dicarbonylrhodium(I) (acetylacetonato)) and tris(2,4-di-t-butylphenyl) phosphite ligand in a PAO-4 (polyalphaolefin) high-boiling inert solvent.

[0176] In a non-limiting example, stream 1 may include one or more raw materials specified in the sales specifications of FIGS. 7-12.

[0177] In one embodiment, a feed containing an alpha olefin or a mixture of linear olefins can be isomerized at a temperature in the range of 30°C to 500°C, 40°C to 200°C, or 50°C to 120°C, and non-limiting examples include 30°C, 50°C, 80°C, 90°C, 100°C, 120°C, 150°C, 180°C, 200°C, 250°C, 300°C, 400°C, or 500°C.

[0178] In one embodiment, a feed containing an alpha olefin or a mixture of linear olefins can be isomerized at a pressure in the range of 0.0 bar(g) to 20 bar(g), 0.1 bar(g) to 10 bar(g), or 0.5 bar(g) to 5 bar(g), and non-limiting examples include 0.01 bar(g), 1 bar(g), 5 bar(g), 7.5 bar(g), 9 bar(g), 10 bar(g), 12 bar(g), 15 bar(g), 18 bar(g), or 20 bar(g).

[0179] In one embodiment, the isomerization of a linear alpha olefin or a mixture of linear alpha olefins can be carried out at a pressure in the range of 0 bar(g) to 20 bar(g), for example, 0 bar(g), 0.1 bar(g), 0.5 bar(g), 1 bar(g), 2 bar(g), 5 bar(g), 10 bar(g), or 20 bar(g).

[0180] In one embodiment, the isomerization of linear α-olefins, or mixtures of linear α-olefins, can be carried out at a CO / H2 molar ratio in the range of 10:1 to 1:10, for example, 5:1, 2:1, 1.5:1, 1.1:1, 1.05:1, 1:1, 1:1.05, 1:1.1, 1:1.15, 1:1.2, 1:1.3, 1:1.5, 1:2, 1:3, 1:5, or 1:10.

[0181] In one embodiment, the isomerization of linear α-olefins, or mixtures of linear α-olefins, can be carried out at a CO / H2 molar ratio in the range of 1.2:1 to 1:1.2.

[0182] In one embodiment, the isomerization of linear α-olefins, or mixtures of linear α-olefins, can be carried out at 20 bar(g) or less and 100 °C or less, for example, at 1 bar(g) and 90 °C. In one embodiment, the isomerization of linear α-olefins, or mixtures of linear α-olefins, can be carried out at a pressure of 20 bar(g) or less, 100 °C or less, and a CO:H2 molar ratio of 1:1 or less, for example, at 1 bar(g), 90 °C, and a CO:H2 ratio of 1:1.15.

[0183] (Stream 1: α-olefin feed composition)

[0184] In one embodiment, Stream 1 can be a C4 - C36 linear α-olefin. For example, the feed of Stream 1 can be a 1-dodecene feed that is substantially a C12 linear α-olefin, such as AlphaPlus® 1-dodecene shown in the sales specification 1 of FIG. 7 (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387 - 4910, phone number (800) 231 - 3260).

[0185] In one embodiment, the feed of Stream 1 can be a 1-dodecene raw material that is substantially a C12 linear alpha olefin, such as NEODENE® 12 (Shell Global Solutions, One Shell Plaza, 910 Louisiana, Houston, TX 77002-4916, USA, phone number (832) 337-2000) shown in the sales specification 3 of FIGS. 9A-9B.

[0186] In another embodiment, the feed of Stream 1 can be a 1-dodecene raw material that is substantially a C12 linear alpha olefin, such as AlphaOlefin C12 (dodecane-1) of Ineos Oligomers (2600 South Shore Drive, Suite 400, League City, Texas 77573, phone number (281) 535-4266) shown in the sales specification 4 of FIG. 10.

[0187] In one embodiment, the feed of Stream 1 can be a 1-tetradecene raw material that is substantially a C14 linear alpha olefin, such as AlphaPlus® 1-tetradecene (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, USA, phone number (800) 231-3260) shown in the sales specification 2 of FIG. 8.

[0188] In one embodiment, the feed of Stream 1 can be a 1-tetradecene raw material that is substantially a C14 linear alpha olefin, such as NEODENE® 14 (Shell Global Solutions, One Shell Plaza, 910 Louisiana, Houston, TX 77002-4916, USA, phone number (832) 337-2000) shown in the sales specification 5 of FIGS. 11A-11B.

[0189] In another embodiment, the feed of Stream 1 can be a 1-tetradecene raw material that is substantially a C14 linear alpha olefin, such as AlphaOlefin C14 (tetradecane-1) of Ineos Oligomers (2600 South Shore Drive, Suite 400, League City, Texas 77573, phone number (281) 535-4266) shown in the sales specification 12 of FIG. 6.

[0190] In one embodiment, the feed of Stream 1 can be a composition containing one or more α-olefins. The α-olefins in the feed of Stream 1 can be the same or different and can have the same or different carbon chain lengths. For example, the α-olefins in Stream 1 supplied as reactants for isomerization can be one or more α-olefins from the group of C4 - C36 α-olefins.

[0191] In one embodiment, the C12 linear α-olefin supplied as a reactant for isomerization can be 90.0 wt% or more, for example, 94.0 wt% or more of C12 linear α-olefin, 94.6 wt% of C12 linear α-olefin, 99 wt% of C12 linear α-olefin, or more.

[0192] In one embodiment, the C14 α-olefin supplied as a reactant for isomerization can be 90.0 wt% or more, for example, 93.0 wt% or more of C14 linear α-olefin, or 93.4 wt% of C14 linear α-olefin, or 99 wt% or more of C14 linear α-olefin, or more.

[0193] In one embodiment, the α-olefin raw material to the isomerization reactor has a vinylidene concentration of 10 wt% or less, for example, 4 wt% or less.

[0194] (Stream 2: Isomerization Reactor Product Stream Composition)

[0195] The isomerization reaction in the isomerization reactor 100 produces an isomerization reaction product stream that is supplied to the hydroformylation reactor 200. Stream 2 can have a composition containing the internal olefin product obtained by the isomerization reaction. As a non-limiting example, a portion of the starting α-olefin is isomerized to obtain an olefin mixture containing the following. · More than 20 wt% of internal olefins, that is, olefins in which the double bond has isomerized from the α-position to the interior of the molecule, and · Less than 80 wt% of α-olefins

[0196] Stream 2 is an isomerization reactor product stream containing isomerized olefins that can have an isomerization rate in the range of 5 wt% to 99 wt% or more, for example, an isomerization rate of 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 60 wt%, 70 wt%, 80 wt%, 90 wt%, or 99 wt%. In one embodiment, stream 2, which is an isomerization reactor product stream, can have internal olefins with a composition of 20 wt% or more.

[0197] (Stream 3: Hydroformylation product composition)

[0198] In one embodiment, stream 3, which is a hydroformylation product stream, can have a composition containing more than 25 wt% branched aldehyde.

[0199] (Hydroformylation)

[0200] The second stage of the two-stage process illustrated in FIG. 1 occurs in hydroformylation reactor 200. In this step, the feed (stream 2) has a composition containing: · A C4 - C36 olefin mixture containing more than 20 wt% linear internal olefins and less than 80 wt% linear alpha olefins, · Rhodium catalyst A, · Carbon monoxide (CO), · Hydrogen, and · C5 - C37 aldehydes (trace components).

[0201] Optionally, stream 2 may contain a high-boiling inert solvent.

[0202] The reaction in the hydroformylation reactor 200 proceeds at a temperature of 30 to 300 °C using the same rhodium catalyst A. Since a high pressure is advantageous for the production of the desired branched aldehyde, the reaction in the hydroformylation reactor 200 is carried out under a CO / H2 atmosphere at a pressure higher than the pressure in the isomerization reactor (100). In this step, the olefin mixture (or a part of the olefin mixture) is hydroformylated to produce an aldehyde mixture containing the following, and a reaction product (stream 3) is produced. · More than 25 wt% of branched aldehyde, and · Less than 75 wt% of linear aldehyde.

[0203] In one embodiment, the feed to the hydroformylation containing internal olefins or a mixture of alpha-olefins and internal olefins can be hydroformylated at a temperature in the range of 30 °C to 500 °C, 40 °C to 200 °C, or 50 °C to 120 °C, for non-limiting examples, 30 °C, 50 °C, 80 °C, 90 °C, 100 °C, 120 °C, 150 °C, 180 °C, 200 °C, 250 °C, 300 °C, 400 °C, or 500 °C.

[0204] In one embodiment, the feed to the hydroformylation containing internal olefins or a mixture of alpha-olefins and internal olefins can be hydroformylated at a pressure in the range of 0 bar(g) to 500 bar(g), 5 bar(g) to 100 bar(g), or 7 bar(g) to 30 bar(g), for non-limiting examples, 0 bar(g), 1 bar(g), 5 bar(g), 7 bar(g), 10 bar(g), 15 bar(g), 30 bar(g), 50 bar(g), 100 bar(g), 150 bar(g), 200 bar(g), 250 bar(g), 300 bar(g), 350 bar(g), 400 bar(g), or 500 bar(g).

[0205] In one embodiment, the feed to hydroformylation containing internal olefins or a mixture of alpha olefins and internal olefins can be hydroformylated at a CO / H2 molar ratio in the range of 10:1 to 1:10, for example, a CO / H2 molar ratio of 5:1, 2:1, 1.5:1, 1.1:1, 1.05:1, 1:1, 1:1.05, 1:1.1, 1:1.15, 1:1.2, 1:1.3, 1:1.5, 1:2, 1:3, 1:5, or 1:10.

[0206] In one embodiment, the feed to hydroformylation containing internal olefins or a mixture of alpha olefins and internal olefins can be hydroformylated at a CO / H2 molar ratio in the range of 1.2:1 to 1:1.2.

[0207] In one embodiment, a feed containing alpha olefins or a mixture of linear olefins can be hydroformylated at a pressure of 15 bar(g) and 90 °C.

[0208] Stream 2 can also contain a small amount of mixed aldehydes having 5 to 37 carbon atoms generated from the hydroformylation of C4 - C36 alpha olefins and C4 - C36 internal olefins. The generation of aldehydes in the isomerization reactor (100) is not intended but is expected to occur at a low rate. Since the aldehydes generated in this step tend to be linear aldehydes rather than the desired branched aldehydes, the generation of aldehydes in this step should be controlled at a low level.

[0209] Figure 2 shows an embodiment of a chemical manufacturing process using stream 4, which has an isomerization reactor 100 and is any isomerization reactor bypass used to control the feed composition to the hydroformylation reactor 200. In the embodiment of Figure 2, stream 2 of the isomerization reactor product is mixed with stream 4, which is the isomerization reactor bypass stream, to produce stream 6, which is the hydroformylation reactor feed stream of the embodiment of Figure 2.

[0210] Figure 2 shows the two - stage process of Figure 1 in an embodiment having a stream 4 which is any olefin bypass stream that bypasses the isomerization reactor (100). In this aspect, a portion of stream 1 can be used as stream 4 to bypass the isomerization reactor (100) and a portion of stream 1 can be used as stream 5 to be fed to the isomerization reactor (100). Stream 2 is the isomerization product of the isomerization reactor (100) and combines with stream 4 to provide stream 6 which is the feed to the hydroformylation reactor 200. The bypass function of stream 4 provides a convenient and effective means for controlling the degree of olefin isomerization in the process. By adjusting the portion of stream 1 that is isomerized (stream 5) and the portion of stream 1 that is not isomerized (stream 4), the degree of olefin isomerization can be controlled to a desired value. The degree of olefin isomerization is an important variable that determines the degree of branching of the aldehyde. Therefore, by controlling the degree of olefin isomerization, the degree of branching of the aldehyde obtained in stream 3 can be controlled to a desired value.

[0211] In the embodiment of Figure 2, the compositions of stream 1, stream 4 which is the isomerization reactor bypass stream, and stream 5 can be the same. As shown in Figure 2, stream 4 and stream 5 are streams branched from stream 1.

[0212] Stream 1: α - olefin feed composition

[0213] Stream 2: Isomerization reactor product (> 20% internal olefin) composition

[0214] Stream 3: Hydroformylation product (> 25% branching rate) composition

[0215] Stream 4: Isomerization reactor bypass (optional) composition

[0216] Stream 5: Isomerization reactor feed composition

[0217] Stream 6: Hydroformylation Reactor Feed Composition

[0218] Figure 3 shows one embodiment of a chemical manufacturing process having an isomerization reactor, a hydroformylation reactor, and catalyst recovery. In this non-limiting embodiment, a rhodium catalyst is recovered to produce a recovered rhodium catalyst stream, Stream 7, which is recycled to the isomerization reactor 100, and a catalyst recovery step, namely catalyst recovery 300, is added to produce Stream 8 having a composition of branched aldehyde and unreacted olefin, thereby modifying the process of Figure 2. Stream 8 is a product stream of branched aldehyde and unreacted olefin.

[0219] Figure 3 is the process of Figure 2 with catalyst recovery 300 added. Stream 3 is the reactor product of the hydroformylation reactor 200 and has the composition of Stream 3 including the following. · A C5 - C37 aldehyde mixture containing more than 25 wt% branched aldehyde and less than 75 wt% linear aldehyde · Unreacted C4 - C36 olefin · Unreacted CO / H2, and · Rhodium catalyst A.

[0220] In one embodiment, the composition of Stream 3 may optionally include a high-boiling inert solvent.

[0221] In the catalyst recovery 300 step, unreacted CO / H2 gas is discharged, and the aldehyde mixture and unreacted olefin are distilled to the top of the column at a high temperature, for example 100 - 200 °C, under a reduced pressure, for example a pressure lower than 0.1 bar (absolute pressure), to produce a top liquid stream 8. In one embodiment, the olefin fed to the hydroformylation reactor 200 is completely (or almost completely) converted to aldehyde in the hydroformylation reactor 200, and Stream 8 becomes a mixed aldehyde product stream that does not require further purification.

[0222] In the embodiment of FIG. 3, the non-volatile liquid residue from catalyst recovery 300 is shown as stream 7. This stream contains the recovered rhodium catalyst A and, optionally, a high-boiling inert solvent if a solvent is used. Stream 7, which is the recovered rhodium catalyst stream, is then recycled to the isomerization reactor 100 for reuse in the process. Although not essential to the present invention, it is often useful to include a high-boiling inert solvent in the system as a useful liquid carrier for the recovered rhodium catalyst. An example of such a high-boiling inert solvent is polyalphaolefin (PAO). In one embodiment, rhodium catalyst A can be an organometallic complex of rhodium and a water-soluble organic phosphorus ligand. In this embodiment, in the catalyst recovery 300 step, optionally, the catalyst can be separated from the aldehyde product via an aqueous / organic extraction step without passing through a distillation step. In one embodiment, optionally, one or more of the extraction step and / or the distillation step can be used. In these embodiments, the rhodium catalyst can be recovered in the aqueous phase, returned to the isomerization reactor 100 for reuse in the process to form a recycle, and the aldehyde product and unreacted olefin can be recovered as the organic phase resulting from the extraction step.

[0223] Stream 1: α-olefin feed composition

[0224] Stream 2: Isomerization reactor product composition

[0225] Stream 3: Hydroformylation product composition

[0226] Stream 4: Isomerization reactor bypass composition

[0227] Stream 5: Isomerization reactor feed composition

[0228] Stream 6: Hydroformylation reactor feed composition

[0229] Stream 7: Recovered rhodium catalyst stream composition

[0230] Stream 8: Branched Aldehyde / Unreacted Olefin Composition

[0231] Figure 4 shows the process of FIG. 3 with an aldehyde distillation apparatus 400 added. Figure 4 shows an embodiment of a chemical manufacturing process having an isomerization reactor, a hydroformylation reactor, catalyst recovery, and aldehyde distillation.

[0232] Figure 4 shows the process of FIG. 3 with an aldehyde distillation step shown as aldehyde distillation 400 added. In this embodiment, stream 8 is a feed stream to aldehyde distillation (400) and, in one embodiment, has, for example, the following composition. 1) A C5 - C37 aldehyde mixture containing more than 25 wt% branched aldehyde and less than 75 wt% linear aldehyde 2) Unreacted C4 - C36 olefins.

[0233] In the embodiment of Figure 4, in the distillation process of aldehyde distillation 400, unreacted C4 - C36 olefins that were not converted to aldehydes in the hydroformylation reactor 200 are distilled to the top as a light product shown as stream 9 having unreacted olefins. The unreacted olefins in stream 9 are returned to the beginning of the process for reuse and, in the embodiment of Figure 4, are mixed with stream 1. As shown, the unreacted olefins in stream 9 are combined with the α - olefin feed stream 1 to produce stream 10, a mixed olefin feed to the isomerization reactor 100.

[0234] In the embodiment of Figure 4, the C5 - C37 aldehyde mixture of stream 8 produced by catalyst recovery 300 is further purified and refined by distillation in aldehyde distillation 400 to produce a distilled high - purity C5 - C37 branched aldehyde product stream shown as stream 11 that, in one embodiment, does not contain, or substantially does not contain, unreacted C4 - C36 olefins.

[0235] Stream 1: α - Olefin Feed Composition

[0236] Stream 2: Isomerization Reactor Product Composition

[0237] Stream 3: Hydroformylation Product Composition

[0238] Stream 4: Isomerization Reactor Bypass Composition

[0239] Stream 5: Isomerization Reactor Feed Composition

[0240] Stream 6: Hydroformylation Reactor Feed Composition

[0241] Stream 7: Recovered Rhodium Catalyst Stream Composition

[0242] Stream 8: Branched Aldehyde / Unreacted Olefin Composition

[0243] Stream 9: Unreacted Olefin Composition

[0244] Stream 10: Mixed Olefin Feed Composition

[0245] Stream 11: Branched Aldehyde Product Composition

[0246] Figure 5 shows one embodiment of a chemical manufacturing process having an isomerization reactor, a hydroformylation reactor, a catalyst recovery, and an aldehyde hydrogenation reactor.

[0247] Figure 5 shows a different embodiment that modifies the process of Figure 3 such that Stream 8 is fed to an aldehyde hydrogenation reactor 500 to produce a branched alcohol as a branched alcohol product stream, Stream 9.

[0248] Figure 5 shows the process of Figure 3 with an additional aldehyde hydrogenation step shown as aldehyde hydrogenation reactor 500. In one embodiment, Stream 8 is a feed stream to the aldehyde hydrogenation reactor (500) and has, for example, the following composition. 1) A C5-C37 aldehyde mixture containing (a) a branched aldehyde in an amount greater than 25 wt% and (b) a linear aldehyde in an amount less than 75 wt%. 2) Unreacted C4-C36 olefins.

[0249] In the embodiment of FIG. 5, the C5-C37 aldehyde is hydrogenated in an aldehyde hydrogenation reactor (500) in the presence of hydrogen and a hydrogenation catalyst, such as Catalyst A, to produce Stream 12.

[0250] Suitable examples of hydrogenation catalysts include base metal catalysts supported on high surface area carriers such as ceramics, carbon, alumina, silica, titania, and zirconia. These metals have a major base metal component consisting of nickel, cobalt, copper, manganese, molybdenum, zinc, and / or iron, or various combinations thereof, and are attached and dispersed on the surface of the carrier. Examples of base metal nickel include nickel catalysts supported on alumina, silica, titania, zirconia, or carbon. Similar supported metal catalysts can be found for other base metals. Noble metal catalysts supported on high surface area carriers such as ceramics, carbon, alumina, silica, titania, zirconia, etc. are also suitable, and these metals include platinum, palladium, gold, silver, iridium, ruthenium, or various combinations thereof. Examples of noble metal platinum include platinum catalysts supported on carbon, silica, titania, zirconia, or alumina. Similar supported metal catalysts can be found for other noble metals. Raney (registered trademark) nickel catalysts and Raney (registered trademark) cobalt catalysts manufactured by WR Grace & Company (7500 Grace Drive, Columbia, MD 21044, USA, telephone number 1-410-531-4000) are also suitable hydrogenation treatment catalysts. Suitable hydrogenation catalysts can be either a finely divided slurry-type catalyst for use in a stirred batch reactor or a continuous stirred tank reactor (i.e., CSTR), or a fixed bed-type catalyst for use in a reactor such as a trickle bed reactor.

[0251] Stream 12 is a branched alcohol product and, in one embodiment, may have a composition comprising the following. 1) A C5 - C37 alcohol mixture containing (a) more than 30 wt% branched alcohol and (b) less than 70 wt% linear alcohol 2) C4 - C36 paraffins (alkanes).

[0252] In the embodiment of Figure 5, the C5 - C37 alcohol is produced by hydrogenation of the corresponding aldehyde in the aldehyde hydrogenation reactor 500, and the C4 - C36 paraffin is also produced by hydrogenation of the unreacted C4 - C36 olefins contained in stream 8 in the aldehyde hydrogenation reactor 500.

[0253] Optionally, a distillation step is used after the aldehyde hydrogenation reactor 500 to remove the low - boiling C4 - C36 paraffins, producing a distilled high - purity C5 - C37 branched alcohol product that does not contain, or substantially does not contain, C4 - C36 paraffins. As the C4 - C36 paraffin content decreases, it is possible to increase the C5 - C37 alcohol content in stream 12.

[0254] Stream 1: α - olefin feed composition

[0255] Stream 2: Isomerization reactor product composition

[0256] Stream 3: Hydroformylation product composition

[0257] Stream 4: Isomerization reactor bypass composition

[0258] Stream 5: Isomerization reactor feed composition

[0259] Stream 6: Hydroformylation reactor feed composition

[0260] Stream 7: Recovered rhodium catalyst stream composition

[0261] Stream 8: Branched aldehyde / unreacted olefin composition

[0262] Stream 12: Branched alcohol product

[0263] In one embodiment, Stream 12 can be a composition of a branched alcohol product having a branching ratio higher than 25%.

[0264] FIG. 6 shows one embodiment of a chemical manufacturing process having an isomerization reactor, a hydroformylation reactor, catalyst recovery, aldehyde distillation, and an aldehyde hydrogenation reactor. FIG. 6 shows the process of FIG. 4 with an additional aldehyde hydrogenation reactor 500. In the embodiment of FIG. 6, the branched aldehyde product stream, Stream 11, is a feed stream to the aldehyde hydrogenation reactor (500) and can have a C5-C37 aldehyde mixture including, for example, the following. 1) More than 25 wt% branched aldehyde 2) Less than 75 wt% linear aldehyde.

[0265] In the embodiment of FIG. 6, the C5-C37 aldehydes are hydrogenated in the aldehyde hydrogenation reactor (500) in the presence of hydrogen and a hydrogenation catalyst, for example, Catalyst A, to produce Stream 12. Stream 12 is a branched alcohol product stream and can have a C5-C37 alcohol composition including, for example, the following. 1) More than 30 wt% branched alcohol 2) Less than 70 wt% linear alcohol.

[0266] In the embodiment of FIG. 6, the C5-C37 alcohols are produced by hydrogenation of the corresponding aldehydes that are the reaction products of the hydroformylation reactor 200.

[0267] Optionally, a distillation step is added after the aldehyde hydrogenation reactor 500 to remove unwanted impurities such as, for example, low levels of C4 - C36 paraffins, and to purify the distilled C5 - C37 branched alcohol product, thereby increasing the C5 - C37 alcohol content (purity) in stream 12.

[0268] Stream 1: α - olefin feed composition

[0269] Stream 2: Isomerization reactor product composition

[0270] Stream 3: Hydroformylation product composition

[0271] Stream 4: Isomerization reactor bypass composition

[0272] Stream 5: Isomerization reactor feed composition

[0273] Stream 6: Hydroformylation reactor feed composition

[0274] Stream 7: Recovered rhodium catalyst stream composition

[0275] Stream 8: Branched aldehyde / unreacted olefin composition

[0276] Stream 9: Unreacted olefin composition

[0277] Stream 10: Mixed olefin feed composition

[0278] Stream 11: Branched aldehyde product composition

[0279] Stream 12: Branched alcohol product (>30% branching rate)

[0280] <Example 1: Preparation of Branched C13 Aldehyde Product>

[0281] (Introduction)

[0282] In one embodiment, two branched alcohol products are produced from two starting α-olefins by isomerization reaction, hydroformylation reaction, and hydrogenation reaction. Optionally, a mixture of a number of α-olefins can be used.

[0283] In one embodiment, 1-dodecene, the first α-olefin, can be converted to a mixture of branched tridecanols by the chemical process described herein, and 1-tetradecene, the second α-olefin, can be converted to a mixture of branched pentadecanols by a similar chemical process.

[0284] The process can be carried out batchwise or continuously.

[0285] (Embodiment of batch process)

[0286] In one embodiment, the first stage of the process is a batchwise isomerization of individual α-olefins at appropriate temperature and pressure using a homogeneous rhodium organophosphorus ligand catalyst system. The second stage is a hydroformylation reaction using the same rhodium organophosphorus ligand catalyst system, and the corresponding branched tridecanal or branched pentadecanal can be obtained in high yield and selectively. For example, the branched tridecanal product obtained from such isomerization and hydroformylation processes can result in a composition containing a mixture of linear 1-tridecanal and 2-alkyl branched tridecanal isomers. [Table 1]

[0287] In one embodiment, the catalyst used in the isomerization reaction and the hydroformylation reaction is an organometallic rhodium ligand complex composed of Rh(CO)2ACAC ((acetylacetonato)dicarbonylrhodium(I)) and tris(2,4-di-t-butylphenyl) phosphite ligand.

[0288] After completion of the hydroformylation batch chemical process, the crude aldehyde can be flash distilled to remove the expensive catalyst ligand complex and reused. The flashed aldehyde vapor can be directly fed to distillation to obtain a high-purity branched aldehyde intermediate.

[0289] In this embodiment, branched tridecanol and pentadecanol can be hydrogenated batchwise at high pressure and appropriate temperature in the presence of a hydrogenation catalyst such as a base metal catalyst, for example, a supported nickel catalyst such as Raney® (WR Grace & Company, 7500 Grace Drive, Columbia, MD 21044, USA, phone number 1-410-531-4000) or a noble metal catalyst. During hydrogenation, the aldehyde functional group is converted to the corresponding alcohol, producing the desired branched tridecanol and the desired branched pentadecanol.

[0290] In an embodiment of the batch reaction, the isomerization reaction and the hydroformylation reaction can be carried out in the same or different reactors.

[0291] When the same reactor is used for both the isomerization reaction and the hydroformylation reaction, the isomerization can be carried out under one set of reaction conditions and the hydroformylation can be carried out under a different set of reaction conditions. The reaction temperatures of the isomerization reaction and the hydroformylation reaction may be the same or different. The reaction pressures of the isomerization reaction and the hydroformylation reaction may be the same or different. The molar ratio of CO:H2 in the isomerization reaction and the hydroformylation reaction may be the same or different. In one embodiment, the hydroformylation reaction is carried out at a higher pressure than the isomerization reaction.

[0292] In one embodiment, the batch hydroformylation reaction is carried out at a suitable temperature of 80 °C to 100 °C and a suitable pressure of 15 to 20 bar(g). In this embodiment, the flash removal of the branched aldehyde can be carried out in a flash unit operation, such as a flash drum, optionally in combination with a distillation column. In another embodiment, the flash removal of the branched aldehyde can be carried out in an evaporation unit operation, such as a wiped film evaporator or a falling film evaporator, optionally in combination with a distillation column. Any distillation can be carried out at a pressure including a variable vacuum of 1 mbar absolute pressure to 999 mbar absolute pressure, and as non-limiting examples, 5 mbar absolute pressure, 10 mbar absolute pressure, 20 mbar absolute pressure, 50 mbar absolute pressure, 100 mbar absolute pressure, 500 mbar absolute pressure, or higher pressures.

[0293] In one embodiment, the hydrogenation of the branched aldehyde intermediate is carried out in a batch reactor at a hydrogen pressure of 10 bar(g) to 100 bar(g), such as 20 bar(g), 30 bar(g), 40 bar(g), 50 bar(g), 60 bar(g), 70 bar(g), 80 bar(g), 90 bar(g), or higher. This hydrogenation can be carried out at a temperature of 50 °C to 300 °C, such as 50 °C, 100 °C, 150 °C, 200 °C, 250 °C, 300 °C, 350 °C, 400 °C, or 450 °C.

[0294] In one embodiment, the reaction of the reactants is considered complete when the remaining branched aldehyde intermediate is less than 1%. In one embodiment, the reaction of the reactants is considered complete when the remaining branched aldehyde intermediate is less than 0.1%. In this embodiment, the filtered crude branched alcohol becomes a product that is nearly colorless, has high purity (>97%) and high branching (>80%).

[0295] In one embodiment, a branched aldehyde intermediate can be produced from an α-olefin feed through a batch isomerization process, a batch hydroformylation process, and then flash distillation to produce a branched alcohol product. The branched alcohol of the final product is produced by hydrogenating the branched aldehyde intermediate in a batch mode and filtering the product to remove the hydrogenation catalyst.

[0296] <Example 2: Preparation of Branched C13 Alcohol Product>

[0297] The C12 linear α-olefin raw material (1-dodecene) was obtained as the product AlphaPlus® 1-dodecene from Chevron Phillips Chemical Company (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, USA, telephone number (800) 231-3260). The homogeneous rhodium organophosphorus catalyst used in this example was prepared in a high-pressure stainless steel stirred autoclave. To the autoclave were added 0.027 wt% of Rh(CO)2ACAC (rhodium(I) acetylacetonate dicarbonyl), 1.36 wt% of tris(2,4-di-t-butylphenyl) phosphite ligand, and 98.62 wt% of Synfluid® PAO4cSt (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, telephone number (800) 231-3260) inert solvent. This mixture was heated at 80 °C for 4 hours under a CO / H2 atmosphere at a pressure of 2 bar(g) to produce an active rhodium catalyst solution (rhodium 109 ppm, P:Rh molar ratio = 20). 1-Dodecene linear α-olefin was added to the rhodium catalyst solution in the autoclave to produce a starting reaction mixture with a rhodium concentration of 35 ppm. This α-olefin feed was isomerized at 80 °C for 10 hours under a CO / H2 atmosphere at a pressure of 1 bar(g). The isomerized olefin was then hydroformylated at 70 °C for 8 hours under a CO / H2 atmosphere at a pressure of 20 bar(g). The molar ratio of CO to H2 in both the isomerization step and the hydroformylation step was 1:1.15. The resulting hydroformylation reaction product was flash distilled at 140 - 150 °C and 25 mbar absolute pressure to recover the rhodium catalyst solution as the bottom product and to recover a branched C13 aldehyde top product having the following composition. wt% 1-Tridecanal 13.9% 2-Methyldodecanal 28.3% 2-Ethylundecanal 15.2% 2-Propyl-decanal 14.5% 2-Butylnonanal 13.6% 2-Pentyloctanal 12.6% Total 98.0%

[0298] The weight percentage of the branched C13 aldehyde product was 85.8%. The weight percentage of the linear aldehyde was 14.2%. The weight percentage of the 2-methyl branched aldehyde was 28.9%. The weight percentage of the 2-ethyl branched aldehyde was 15.5%.

[0299] The freezing point of this branched C13 aldehyde product was measured according to the analytical method ASTM D7153 using an ISL FZP 5G2S OptiFZP freezing point analyzer manufactured by PAC L.P. (8824 Fallbrook Drive, Houston, Texas, USA; 1-281-940-1830; www.paclp.com). At -100 °C, which is the lower limit of the operating temperature of this device, the branched C13 aldehyde product did not reach the freezing point (i.e., the freezing point was less than -100 °C).

[0300] The viscosity of this branched C13 aldehyde product was measured according to the analytical method ASTM D7042 using a Stabinger Viscometer SVM3000 manufactured by Anton Paar GmbH (Anton Paar Strasse 20, 8054 Graz, Austria; +43 316 2570; www.anton-paar.com). The viscosity of this branched C13 aldehyde product in centipoise (cP) units at each temperature (°C) is as follows.

Table 2

[0301] This branched C13 aldehyde product was hydrogenated in a high-pressure Inconel 625 stirred autoclave at 150 °C and a hydrogen pressure of 20 bar(g). As the hydrogenation catalyst, Raney (registered trademark) Nickel 3111 (WR Grace & Company, 7500 Grace Drive, Columbia, MD 21044, USA, phone number 1-410-531-4000) catalyst was used at an addition amount of 0.25 wt%. The aldehyde was hydrogenated for 10 hours, and the resulting reaction mixture was filtered to produce a branched C13 alcohol product containing the following. wt% 1-Tridecanol 13.2% 2-Methyldodecanol 29.1% 2-Ethylundecanol 15.5% 2-Propyldecanol 14.4% 2-Butylnonanol 13.2% 2-Pentyloctanol 12.9% Total 98.4%

[0302] The wt% of the branching ratio of the branched C13 alcohol product was 86.6%. The wt% of the linear alcohol was 13.4%. The wt% of the 2-methyl branched alcohol was 29.6%. The wt% of the 2-ethyl branched alcohol was 15.8%.

[0303] The freezing point of this branched C13 alcohol product was measured according to the analytical method ASTM D7153 using an ISL FZP 5G2S OptiFZP freezing point analyzer manufactured by PAC L.P. (8824 Fallbrook Drive, Houston, Texas, USA; 1-281-940-1830; www.paclp.com). At -100 °C, which is the lower limit of the operating temperature of this apparatus, the branched C13 alcohol product did not reach the freezing point (i.e., the freezing point was less than -100 °C).

[0304] The viscosity of this branched C13 alcohol product was measured according to the analytical method ASTM D7042 using a Stabinger Viscometer SVM3000 manufactured by Anton Paar GmbH (Anton Paar Strasse 20, 8054 Graz, Austria; +43 316 2570; www.anton-paar.com). The viscosity in centipoise (cP) at each temperature (°C) in this branched C13 alcohol product is as follows. [Table 3]

[0305] <Example 3: Preparation of Branched C15 Alcohol Product>

[0306] The rhodium catalyst stream recovered from Example 2 was charged into a stirred autoclave made of high-pressure stainless steel, and a C14 linear alpha-olefin raw material (1-tetradecene) from Chevron Phillips Chemical Company (AlphaPlus® 1-tetradecene, Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, telephone number (800) 231-3260) was added. The resulting mixture had a rhodium concentration of about 30 ppm. This 1-tetradecene linear alpha-olefin was isomerized at 80 °C for 12 hours under a CO / H2 atmosphere at a pressure of 1 bar(g). Subsequently, the isomerized olefin was hydroformylated at 70 °C for 8 hours under a CO / H2 atmosphere at a pressure of 20 bar(g). The resulting reaction product was flash distilled at 150 - 160 °C and 25 mbar absolute pressure to recover a rhodium catalyst solution as a bottom product and a branched C15 aldehyde top product. Thereafter, the recovered rhodium catalyst solution was used again to complete a second batch isomerization (4 hours) and hydroformylation (6 hours) of 1-tetradecene. The C15 aldehyde products obtained from the two batches were combined to obtain a branched C15 aldehyde product containing the following. wt% 1-pentadecanal 12.1% 2-methyltetradecanal 34.1% 2-ethyltridecanal 21.9% 2-propyl-dodecanal 14.0% 2-butylundecanal 8.6% 2-pentyldecanal + 2-hexyldecanal 9.0% Total 99.6%

[0307] The weight percentage of the branching ratio of the branched C15 aldehyde product was 87.8%. The weight percentage of the linear aldehyde was 12.1%. The weight percentage of the 2-methyl branched aldehyde was 34.2%. The weight percentage of the 2-ethyl branched aldehyde was 22.0%.

[0308] The freezing point of this branched C15 aldehyde product was measured according to the analytical method ASTM D7153 using an ISL FZP 5G2S OptiFZP freezing point analyzer manufactured by PAC L.P. (8824 Fallbrook Drive, Houston, Texas, USA; 1-281-940-1830; www.paclp.com). At -100 °C, which is the lower limit of the operating temperature of this apparatus, the branched C15 aldehyde product did not reach the freezing point (i.e., the freezing point was less than -100 °C).

[0309] The viscosity of this branched C15 aldehyde product was measured according to the analytical method ASTM D7042 using a Stabinger Viscometer SVM3000 manufactured by Anton Paar GmbH (Anton Paar Strasse 20, 8054 Graz, Austria; +43 316 2570; www.anton-paar.com). The viscosity of this branched C15 aldehyde product in centipoise (cP) units at each temperature (°C) is as follows.

Table 4

[0310] This branched C15 aldehyde product was hydrogenated in a high-pressure Inconel 625 stirred autoclave at 150 °C and a hydrogen pressure of 20 bar(g). As the hydrogenation catalyst, Raney (registered trademark) Nickel 3111 (WR Grace & Company, 7500 Grace Drive, Columbia, MD 21044, USA, phone number 1-410-531-4000) catalyst was used at an addition amount of 0.25 wt%. The aldehyde was hydrogenated for 10 hours, and the resulting reaction mixture was filtered to produce a branched C15 alcohol product containing the following. wt% 1-Pentadecanol 13.7% 2-Methyltetradecanol 33.8% 2-Ethyltridecanol 21.4% 2-Propyl-dodecanol 12.4% 2-Butylundecanol 8.0% 2-Pentyldecanol + 2-Hexylnonanal 9.2% Total 98.4%

[0311] The weight percentage of the branching rate of the branched C15 alcohol product was 86.1%. The weight percentage of the linear alcohol was 13.9%. The weight percentage of the 2-methyl branched alcohol was 34.3%. The weight percentage of the 2-ethyl branched alcohol was 21.7%.

[0312] The freezing point of this branched C15 alcohol product was measured according to the analytical method ASTM D7153 using an ISL FZP 5G2S OptiFZP freezing point analyzer manufactured by PAC L.P. (8824 Fallbrook Drive, Houston, Texas, USA; 1-281-940-1830; www.paclp.com). At -100 °C, which is the lower limit of the operating temperature of this device, the branched C15 alcohol product did not reach the freezing point (i.e., the freezing point was less than -100 °C).

[0313] The viscosity of this branched C15 alcohol product was measured according to the analytical method ASTM D7042 using a Stabinger Viscometer SVM3000 manufactured by Anton Paar GmbH (Anton Paar Strasse 20, 8054 Graz, Austria; +43 316 2570; www.anton-paar.com). The viscosity of this branched C15 alcohol product in centipoise (cP) units at each temperature (°C) is as follows.

Table 5

[0314] <Example 4: Preparation of Branched C15 Aldehyde Product>

[0315] The C14 linear α-olefin raw material (1-tetradecene) was obtained as the product AlphaPlus® 1-tetradecene from Chevron Phillips Chemical Company (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, USA, phone number (800) 231-3260). The homogeneous rhodium organophosphorus catalyst used in this example is a metal-organic complex of Rh(CO)2ACAC (dicarbonyl(acetylacetonato)rhodium(I)) and a triphenylphosphine ligand. 1-Tetradecene linear α-olefin was added to the rhodium catalyst solution in a stainless-steel autoclave to produce a starting reaction mixture with a rhodium concentration of 35 ppm and a P:Rh molar ratio = 20. This α-olefin feed was isomerized at 80 °C for 3.5 hours under a CO / H2 atmosphere at a pressure of 1.5 bar(g). Subsequently, the isomerized olefin was hydroformylated at 95 °C for 9 hours under a CO / H2 atmosphere at a pressure of 14 bar(g). The molar ratio of CO to H2 in both the isomerization step and the hydroformylation step was 1:1.15. The resulting hydroformylation reaction product was flash distilled at 140 - 150 °C and 5 mbar absolute pressure to recover a branched C15 aldehyde overhead product having the following aldehyde composition. wt% 1-Pentadecanal 52.5% 2-Methyltetradecanal 33.1% 2-Ethyltridecanal 10.8% 2-Propyl-dodecanal 1.6% 2-Butylundecanal 0.6% 2-Pentyldecanal + 2-Hexylnonanal 0.9% Total 99.4%

[0316] The weight percentage of the branching ratio of the branched C15 aldehyde product was 47.2%. The weight percentage of the linear aldehyde was 52.8%. The weight percentage of the 2-methyl branched aldehyde was 33.3%. The weight percentage of the 2-ethyl branched aldehyde was 10.9%.

[0317] Figure 13 shows an embodiment of a chemical manufacturing process for producing n branched alcohol products by means of an isomerization reactor, a hydroformylation reactor, catalyst recovery, aldehyde distillation, n α-olefin feeds to an aldehyde hydrogenation reactor, and n alcohol distillation unit operations. In the embodiment of Figure 13, n α-olefin feeds, indicated as F1, F2, …, F n The n α-olefin feeds, indicated as n , are fed to an isomerization reactor 100, and an isomerization reactor product stream 3 containing n isomerized olefins is produced. Stream 3 is fed to a hydroformylation reactor 200, and a stream 4, which is a mixture of n branched aldehydes, is produced. In the catalyst recovery 300 step, a mixture of n branched aldehydes and unreacted olefins is distilled overhead to produce an overhead stream 5, and the rhodium catalyst stream is recovered as a bottoms product stream 6 and returned to the isomerization reactor 100 for reuse in the process. In the aldehyde distillation 400 step, unreacted olefins that were not converted to aldehydes in the hydroformylation reactor 200 are distilled overhead and recovered as a light product, indicated as stream 7, containing unreacted olefins. These unreacted olefins are recycled to the beginning of the process to produce additional aldehyde products via an additional reaction process. In the embodiment of Figure 13, stream 8 produced in the aldehyde distillation 400 step contains a high-purity mixture of the distilled n branched aldehydes and, in one embodiment, contains no or substantially no unreacted olefins.

[0318] In the embodiment of Figure 13, the mixture of n branched aldehydes is hydrogenated in an aldehyde hydrogenation reactor (500) in the presence of hydrogen and a hydrogenation catalyst to produce a reaction product stream, stream 9, which contains a mixture of n branched alcohols. In one embodiment, each of the n branched alcohols produced from the hydrogenation of the corresponding n branched aldehydes has, for example, the following alcohol isomer composition. 1) More than 30 wt% branched alcohol 2) Less than 70 wt% linear alcohol.

[0319] In the embodiment of FIG. 13, a mixture of n branched alcohols (stream 9) from the aldehyde hydrogenation reactor 500 is fed to the alcohol 1 distillation unit operation D-1, low-boiling impurities are removed as the light stream L1, the branched alcohol 1 is recovered as the purified and cleaned branched alcohol product P1, and the bottom stream (stream B1) of the alcohol 1 distillation unit operation D-1 is fed to the alcohol 2 distillation unit operation D-2. In the alcohol 2 distillation unit operation D-2, low-boiling impurities are removed as the light stream L2, the branched alcohol 2 is recovered as the purified and cleaned branched alcohol product P2, and the bottom stream from the alcohol 2 distillation unit operation D-2 is recovered as stream B2. Similarly, each of the n branched alcohols contained in the mixture of branched alcohol products (stream 9) from the aldehyde hydrogenation reactor 500 is purified by the distillation unit operation, and n purified branched alcohol products are produced.

[0320] FIG. 13 shows the following streams.

[0321] Stream F1: α-olefin feed 1

[0322] Stream F2: α-olefin feed 2

[0323] Stream F n : α-olefin feed n

[0324] Stream 3: Isomerization reactor product

[0325] Stream 4: Hydroformylation product (branched aldehyde)

[0326] Stream 5: Branched aldehyde / unreacted olefin

[0327] Stream 6: Recovered rhodium catalyst stream

[0328] Stream 7: Unreacted olefin

[0329] Stream 8: Branched aldehyde

[0330] Stream 9: Crude branched alcohol

[0331] Stream L1: Light stream 1

[0332] Stream P1: Branched alcohol 1 product

[0333] Stream B1: Bottom stream from alcohol 1 distillation

[0334] Stream L2: Light stream 2

[0335] Stream P2: Branched alcohol 2 product

[0336] Stream B2: Bottom stream from alcohol 2 distillation

[0337] Stream L n : Light stream n

[0338] Stream P n : Branched alcohol n product

[0339] Stream B n : Bottom stream from alcohol n distillation

[0340] Figure 14 shows an embodiment of the chemical manufacturing process shown in Figure 13 where the number n of α-olefin feeds is 2. Specifically, the first α-olefin feed F1 is a C12 α-olefin (i.e., 1-dodecene), and the second α-olefin feed F2 is a C14 α-olefin (i.e., 1-tetradecene). These two α-olefin feeds are supplied to the isomerization reactor 100, and an isomerization reactor product stream 3 containing isomerized C12 olefin and isomerized C14 olefin is produced. Stream 3 is supplied to the hydroformylation reactor 200, and a stream 4 which is a mixture of C13 branched aldehyde and C15 branched aldehyde is produced. In the catalyst recovery 300 step, a mixture of C13 and C15 branched aldehydes and unreacted olefins is distilled at the top to produce a top stream 5, and the rhodium catalyst stream is recovered as a bottom product stream 6 and returned to the isomerization reactor 100 for reuse in the process. In the aldehyde distillation 400 step, unreacted C12 / C14 olefins are distilled at the top and recovered as a light product shown as a stream 7 containing unreacted C12 / C14 olefins. These unreacted C12 / C14 olefins are recycled to the beginning of the process to produce additional branched C13 aldehyde and branched C15 aldehyde via an additional reaction process. In the embodiment of Figure 14, stream 8 produced in the aldehyde distillation 400 step contains a high-purity mixture of distilled C13 branched aldehyde and C15 branched aldehyde and, in one embodiment, does not contain or substantially does not contain unreacted C12 / C14 olefins.

[0341] In the embodiment of Figure 14, a mixture of branched C13 aldehyde and branched C15 aldehyde is hydrogenated in an aldehyde hydrogenation reactor (500) in the presence of hydrogen and a hydrogenation catalyst to produce a reaction product stream 9 which is a mixture of C13 branched alcohol and C15 branched alcohol. In one embodiment, the C13 branched alcohol produced from the hydrogenation of the corresponding branched C13 aldehyde has, for example, the following C13 alcohol isomer composition. 1) More than 30 wt% branched C13 alcohol 2) Linear C13 alcohol less than 70 wt%.

[0342] In one embodiment, the C15 branched alcohol produced from the hydrogenation of the corresponding branched C15 aldehyde has, for example, the following C15 alcohol isomer composition. 3) Branched C15 alcohol more than 30 wt%. 4) Linear C15 alcohol less than 70 wt%.

[0343] In the embodiment of FIG. 14, the mixture of C13 branched alcohol and C15 branched alcohol from the aldehyde hydrogenation reactor 500 (stream 9) is fed to the C13 alcohol distillation unit operation D-1, where low-boiling impurities are removed as the light stream 10, the branched C13 alcohol is recovered as the purified and refined branched C13 alcohol product stream 11, and the bottom stream (stream 12) of the C13 alcohol distillation unit operation D-1 is fed to the C15 alcohol distillation unit operation D-2. In the C15 alcohol distillation unit operation D-2, low-boiling impurities are removed as the light stream 13, the branched C15 alcohol is recovered as the purified and refined branched C15 alcohol product stream 14, and the bottom stream from the C15 alcohol distillation unit operation D-2 is recovered as stream 15.

[0344] FIG. 14 shows the following streams.

[0345] Stream F1: C12 α-olefin feed

[0346] Stream F2: C14 α-olefin feed

[0347] Stream 3: Isomerization reactor product (C12 / C14 isomerized olefin)

[0348] Stream 4: Hydroformylation product (branched C13 / C15 aldehyde)

[0349] Stream 5: Branched C13 / C15 aldehyde / unreacted C12 / C14 olefin

[0350] Stream 6: Recovered rhodium catalyst stream

[0351] Stream 7: Unreacted C12 / C14 olefins

[0352] Stream 8: Branched C13 / C15 aldehydes

[0353] Stream 9: Branched C13 / C15 alcohols

[0354] Stream 10: C12 / C14 light stream

[0355] Stream 11: Branched C13 alcohol product

[0356] Stream 12: Crude branched C15 alcohol

[0357] Stream 13: Light stream from C15 alcohol distillation

[0358] Stream 14: Branched C15 alcohol product

[0359] Stream 15: Bottom stream from C15 alcohol distillation

[0360] Figure 15 shows an embodiment of the chemical manufacturing process shown in Figure 14 having an isomerization reactor, a hydroformylation reactor, catalyst recovery, an aldehyde hydrogenation reactor, C13 alcohol distillation unit operation, and C15 alcohol distillation unit operation. However, in this embodiment, since there is no aldehyde distillation unit, there is no recovery and recycle of unreacted C12 / C14 olefins. In this embodiment, the hydroformylation reactor 200 is operated such that the hydroformylation reaction that converts isomerized C12 / C14 olefins to branched C13 aldehydes and branched C15 aldehydes occurs at a very high chemical conversion rate of C12 / C14 olefins, for example, a conversion rate of 90% or more, or a conversion rate of 95% or more, or a conversion rate of 98% or more. Thereby, since only a low concentration of unreacted C12 / C14 olefins remains in the hydroformylation product (stream 4), the aldehyde distillation step can be omitted. In the catalyst recovery 300 step, the rhodium catalyst stream is recovered as the bottom product stream 6, and a mixture of C13 and C15 branched aldehydes and a low level of unreacted C12 / C14 olefins is distilled to the top as stream 5. In the embodiment of Figure 15, the mixture of branched C13 aldehyde, branched C15 aldehyde, and a low level of unreacted C12 / C14 olefins is hydrogenated in an aldehyde hydrogenation reactor (500) in the presence of hydrogen and a hydrogenation catalyst to produce a reaction product stream 7 containing a mixture of C13 branched alcohol, C15 branched alcohol, and a low level of C12 alkane (dodecane) and C14 alkane (tetradecane). These C12 and C14 alkanes are formed from the hydrogenation of the corresponding C12 and C14 alkenes. In one embodiment, the C13 branched alcohol in stream 7 produced from the hydrogenation of the corresponding branched C13 aldehyde has, for example, the following C13 alcohol isomer composition. 5) More than 30 wt% branched C13 alcohol 6) Less than 70 wt% linear C13 alcohol.

[0361] In one embodiment, the C15 branched alcohols in stream 7 produced from the hydrogenation of the corresponding branched C15 aldehydes have, for example, the following C15 alcohol isomer composition. 7) More than 30 wt% branched C15 alcohols 8) Less than 70 wt% linear C15 alcohols.

[0362] In the embodiment of FIG. 15, a mixture of C13 branched alcohols, C15 branched alcohols, and low levels of C12 and C14 alkanes (stream 7) from the aldehyde hydrogenation reactor 500 is fed to the C13 alcohol distillation unit operation D-1. In this unit operation step, C12 alkanes and C14 alkanes are removed as low-boiling impurities in the light stream 8, the branched C13 alcohols are recovered as the purified and cleaned branched C13 alcohol product stream 9, and the bottom stream (stream 10) from the C13 alcohol distillation unit operation D-1 is fed to the C15 alcohol distillation unit operation D-2. In the C15 alcohol distillation unit operation D-2, low-boiling impurities are removed as the light stream 11, the branched C15 alcohols are recovered as the purified and cleaned branched C15 alcohol product stream 12, and the bottom stream from the C15 alcohol distillation unit operation D-2 is recovered as stream 13.

[0363] FIG. 15 shows the following streams.

[0364] Stream F1: C12 α-olefin feed

[0365] Stream F2: C14 α-olefin feed

[0366] Stream 3: Isomerization reactor product (C12 / C14 isomerized olefins)

[0367] Stream 4: Hydroformylation product (branched C13 / C15 aldehydes)

[0368] Stream 5: Branched C13 / C15 aldehyde / unreacted C12 / C14 olefin

[0369] Stream 6: Recovered rhodium catalyst stream

[0370] Stream 7: Branched C13 / C15 alcohol

[0371] Stream 8: C12 alkane / C14 alkane light stream

[0372] Stream 9: Branched C13 alcohol product

[0373] Stream 10: Crude branched C15 alcohol

[0374] Stream 11: Light stream from C15 alcohol distillation

[0375] Stream 12: Branched C15 alcohol product

[0376] Stream 13: Bottom stream from C15 alcohol distillation

[0377] FIG. 16 shows an embodiment of the chemical manufacturing process shown in FIG. 13, but in this embodiment, the final product of the process is not the n branched alcohol products as shown in FIG. 13, but n branched aldehyde products. This embodiment is preferred when a branched aldehyde is desired as the product. This is advantageous when the purified branched aldehyde is desired as the final product used (e.g., for fragrance applications), or when the purified branched aldehyde is desired as an intermediate for producing other useful derivatives such as branched amines and branched carboxylic acids. The embodiment shown in FIG. 16 shows a chemical manufacturing process for producing n branched aldehyde products by an isomerization reactor, a hydroformylation reactor, catalyst recovery, n α-olefin feeds to aldehyde distillation, and n aldehyde distillation unit operations. By this process, a distilled high-purity mixture of n branched aldehydes can be produced as stream 8 in a manner directly similar to the process shown in FIG. 13. In one embodiment, stream 8 does not contain or substantially does not contain unreacted olefins. In the embodiment of FIG. 16, stream 8 is not hydrogenated to alcohol but is fed directly to a series of aldehyde distillation unit operations. In the embodiment of FIG. 16, the mixture of n branched aldehydes (stream 8) is fed to aldehyde 1 distillation unit operation D-1, low-boiling impurities are removed as light stream L1, branched aldehyde 1 is recovered as the purified and purified branched aldehyde product P1, and the bottom stream (stream B1) of aldehyde 1 distillation unit operation D-1 is fed to aldehyde 2 distillation unit operation D-2. In aldehyde 2 distillation unit operation D-2, low-boiling impurities are removed as light stream L2, branched aldehyde 2 is recovered as the purified and purified branched aldehyde product P2, and the bottom stream from aldehyde 2 distillation unit operation D-2 is recovered as stream B2. Similarly, each of the n branched aldehydes contained in the branched aldehyde mixture stream 8 is purified in a distillation unit operation, and n purified branched aldehyde products are produced.

[0378] FIG. 16 shows the following streams.

[0379] Stream F1: α-olefin feed 1

[0380] Stream F2: α-olefin feed 2

[0381] Stream F n : α-olefin feed n

[0382] Stream 3: Isomerization reactor product

[0383] Stream 4: Hydroformylation product (branched aldehyde)

[0384] Stream 5: Branched aldehyde / unreacted olefin

[0385] Stream 6: Recovered rhodium catalyst stream

[0386] Stream 7: Unreacted olefin

[0387] Stream 8: Branched aldehyde

[0388] Stream L1: Light stream 1

[0389] Stream P1: Branched aldehyde 1 product

[0390] Stream B1: Bottom stream from aldehyde 1 distillation

[0391] Stream L2: Light stream 2

[0392] Stream P2: Branched aldehyde 1 product

[0393] Stream B2: Bottom stream from aldehyde 2 distillation

[0394] Stream L n : Light stream n

[0395] Stream P n : Branched aldehyde n product

[0396] Stream B n : Bottom stream from aldehyde n distillation

[0397] (Introduction of Examples 5 - 7)

[0398] Examples 5 - 7 are examples showing the simultaneous production of branched C13 aldehyde and branched C15 aldehyde, and examples showing the simultaneous production of branched C13 alcohol and branched C15 alcohol. Example 5 provides a first example of a two - step process for the simultaneous production of branched C13 aldehyde and branched C15 aldehyde from a starting α - olefin feed containing a 50:50 mixture of 1 - dodecene and 1 - tetradecene. Example 6 provides a second example of a two - step process for the simultaneous production of branched C13 aldehyde and branched C15 aldehyde from a 50:50 mixture of 1 - dodecene and 1 - tetradecene, which produces an aldehyde product with an increased degree of isomerization and an increased degree of branching. In Example 7, the branched C13 aldehyde and branched C15 aldehyde produced in Examples 5 and 6 were hydrogenated to produce a mixture of branched C13 alcohol and branched C15 alcohol.

[0399] <Example 5: Production of Branched C13 Aldehyde and Branched C15 Aldehyde>

[0400] The C12 linear α-olefin raw material (1-dodecene) and the C14 linear α-olefin raw material (1-tetradecene) were obtained from Chevron Phillips Chemical Company under the product names AlphaPlus® 1-dodecene and AlphaPlus® 1-tetradecene, respectively (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, phone number (800) 231-3260). As the homogeneous rhodium organophosphorus catalyst solution for Example 5, a mixture containing 0.040 wt% of Rh(CO)2ACAC (dicarbonyl(acetylacetonato)rhodium(I)), 2.51 wt% of tris(2,4-di-t-butylphenyl) phosphite ligand, and 97.45 wt% of Synfluid® PAO4cSt (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, phone number (800) 231-3260) inert solvent was used. This mixture was heated at 110 °C for 2 hours with stirring in the presence of a nitrogen atmosphere to produce an active rhodium catalyst solution (rhodium 160 ppm, P:Rh molar ratio = 25). The starting reaction mixture contained 37.5 wt% of the C12 linear α-olefin raw material, 37.5 wt% of the C14 linear α-olefin raw material, and 25 wt% of the active rhodium catalyst solution.

[0401] Using a starting reaction mixture having a rhodium concentration of 40 ppm, the mixture was placed in a high-pressure stainless steel autoclave and the reaction was carried out in a batch process. The C12 / C14 α-olefin feed mixture was isomerized at 70 °C for 2.0 hours under a CO / H2 atmosphere at a pressure of 1.4 bar(g). The isomerized olefin mixture was then hydroformylated at 70 °C for 4 hours under a CO / H2 atmosphere at a pressure of 15 bar(g). The molar ratio of H2 to CO in both the isomerization step and the hydroformylation step was 1:1.15. The conversion of the starting olefin to the aldehyde product was 97%. The composition of the obtained hydroformylation reaction product was 39.1 wt% C13 aldehyde and 39.4 wt% C15 aldehyde. The isomer distributions of the produced C13 aldehyde and C15 aldehyde were as follows. wt% C13 aldehyde 1-Tridecanal 8.3% 2-Methyldodecanal 16.8% 2-Ethylundecanal 9.1% 2-Propyl-decanal 3.0% 2-Butylnonanal 1.4% 2-Pentyloctanal 0.5% Total C13 aldehyde: 39.1% C15 aldehyde 1-Pentadecanal 8.3% 2-Methyltetradecanal 16.8% 2-Ethyltridecanal 9.1% 2-Propyl-dodecanal 3.0% 2-Butylundecanal 1.5% 2-Pentyldecanal + 2-Hexylnonanal 0.7% Total C15 aldehyde: 39.4%

[0402] The weight percentage of the branching rate of the branched C13 aldehyde product was 78.8%. The weight percentage of the branching rate of the branched C15 aldehyde product was 78.9%.

[0403] <Example 6: Production of Branched C13 Aldehyde and Branched C15 Aldehyde>

[0404] The time of the isomerization step was increased from 2.0 hours to 3.0 hours, and the time of the hydroformylation step was decreased from 4.0 hours to 3.0 hours, and the batch C12 / C14 α-olefin isomerization / hydroformylation process detailed in Example 5 was repeated. The conversion rate of the starting olefin to the aldehyde product in this example was 94%. The composition of the obtained hydroformylation reaction product was 38.0 wt% C13 aldehyde and 37.9 wt% C15 aldehyde. The isomer distributions of the produced C13 aldehyde and C15 aldehyde are as follows. Weight percentage C13 aldehyde 1-Tridecanal 4.3% 2-Methyldecanal 10.5% 2-Ethylundecanal 8.1% 2-Propyl-decanal 6.3% 2-Butylnonanal 8.4% 2-Pentyloctanal 0.4% Total C13 aldehydes: 38.0% C15 aldehyde 1-Pentadecanal 4.2% 2-Methyltetradecanal 10.4% 2-Ethyltridecanal 8.0% 2-Propyl-dodecanal 6.1% 2-Butylundecanal 8.7% 2-Pentyldecanal + 2-Hexylnonanal 0.5% Total C15 aldehydes: 37.9%

[0405] The weight percentage of the branching ratio of the branched C13 aldehyde product was 88.7%. The weight percentage of the branching ratio of the branched C15 aldehyde product was 88.9%.

[0406] <Example 7: Production of Branched C13 Alcohol and Branched C15 Alcohol>

[0407] The hydroformylation reaction products of Example 5 and Example 6 were combined and flash distilled at 150 - 160 °C and 5 mbar absolute pressure to recover the rhodium catalyst solution as the bottom product and a mixture of branched C13 aldehyde and branched C15 aldehyde as the top product. The composition of this C13 / C15 aldehyde mixture was 49.3 wt% C13 aldehyde and 45.0 wt% C15 aldehyde. The isomer distribution of the produced C13 aldehyde and C15 aldehyde was as follows. Weight percentage C13 aldehyde 1-Tridecanal 8.0% 2-Methyldecanal 17.5% 2-Ethylundecanal 11.0% 2-Propyl decanal 5.9% 2-Butyl nonanal 3.8% 2-Pentyl octanal 3.1% Total C13 aldehydes: 49.3% C15 aldehydes 1-Pentadecanal 6.8% 2-Methyl tetradecanal 15.8% 2-Ethyl tridecanal 10.1% 2-Propyl-dodecanal 5.4% 2-Butyl undecanal 3.6% 2-Pentyl decanal + 2-Hexyl nonanal 3.3% Total C15 aldehydes: 45.0%

[0408] The total weight % of C13 aldehydes and C15 aldehydes in the aldehyde mixture was 94.3%. The total weight % of branched C13 aldehydes and branched C15 aldehydes in the aldehyde mixture was 79.5%. The branching ratio of the branched C13 / C15 aldehyde mixture was 84.3% (i.e., = 79.5% ÷ 94.3%). The total weight % of linear C13 aldehydes and linear C15 aldehydes in the aldehyde mixture was 14.8% (i.e., = 8.0% + 6.8%). The proportion of linear aldehydes was 15.7% (i.e., = 14.8% ÷ 94.3%). The total weight % of 2-methyl branched C13 aldehydes and 2-methyl branched C15 aldehydes in the aldehyde mixture was 33.3% (i.e., = 17.5% + 15.8%). The proportion of 2-methyl branched aldehydes was 35.3% (i.e., = 33.3% ÷ 94.3%). The total weight % of 2-ethyl branched C13 aldehydes and 2-ethyl branched C15 aldehydes in the aldehyde mixture was 21.1% (i.e., = 11.0% + 10.1%). The proportion of 2-ethyl branched aldehydes was 22.4% (i.e., = 21.1% ÷ 94.3%).

[0409] This branched C13 / C15 aldehyde mixture was hydrogenated in a high-pressure stainless steel stirred autoclave at 150 °C and a hydrogen pressure of 25 bar(g). As the hydrogenation catalyst, Raney (registered trademark) Nickel 3111 (WR Grace & Company, 7500 Grace Drive, Columbia, MD 21044, USA, phone number 1-410-531-4000) catalyst was used at an addition amount of 0.50 wt%. The branched C13 / C15 aldehyde mixture was hydrogenated for 4 hours, and the resulting reaction mixture was filtered to produce a branched C13 / C15 alcohol mixture containing 49.4 wt% branched C13 alcohol and 44.1 wt% branched C15 alcohol. The isomer distributions of the produced C13 alcohol and C15 alcohol are as follows. wt% C13 aldehyde 1-Tridecanol 7.9% 2-Methyldodecanol 17.7% 2-Ethylundecanol 11.0% 2-Propyl-decanol 6.0% 2-Butylnonanol 3.8% 2-Pentyloctanol 3.0% Total of C13 alcohol: 49.4% C15 alcohol 1-Pentadecanol 6.5% 2-Methyltetradecanol 16.0% 2-Ethyltridecanol 9.5% 2-Propyl-dodecanol 5.3% 2-Butylundecanol 3.3% 2-Pentyldecanol + 2-Hexylnonanol 3.5% Total of C15 alcohol: 44.1%

[0410] The total weight percentage of C13 alcohol and C15 alcohol in the alcohol mixture was 93.5%. The total weight percentage of branched C13 alcohol and branched C15 alcohol in the alcohol mixture was 79.1%. The branching ratio of the branched C13 / C15 alcohol mixture was 84.6% (i.e., = 79.1% ÷ 93.5%). The total weight percentage of linear C13 alcohol and linear C15 alcohol in the alcohol mixture was 14.4% (i.e., = 7.9% + 6.5%). The proportion of linear alcohol was 15.4% (i.e., = 14.4% ÷ 93.5%). The total weight percentage of 2-methyl branched C13 alcohol and 2-methyl branched C15 alcohol in the alcohol mixture was 33.7% (i.e., = 17.7% + 16.0%). The proportion of 2-methyl branched alcohol was 36.0% (i.e., = 33.7% ÷ 93.5%). The total weight percentage of 2-ethyl branched C13 alcohol and 2-ethyl branched C15 alcohol in the alcohol mixture was 20.5% (i.e., = 11.0% + 9.5%). The proportion of 2-ethyl branched alcohol was 21.9% (i.e., = 20.5% ÷ 93.5%).

[0411] The hydrogenation reaction product also contains 2.4 wt% of C12 alkane (paraffin) and 2.7 wt% of C14 alkane (paraffin), which are the hydrogenation reaction products of unreacted C12 olefin and C14 olefin. These C12 and C14 alkane by-products are easily removed as the "light" stream in the distillation process for purifying the hydrogenation reaction product into high-purity C13 branched alcohol product and high-purity C15 branched alcohol product.

[0412] <Example 8: Production of Branched C15 Aldehyde / C15 Alcohol Product Using Cobalt Catalyst>

[0413] The C14 linear α-olefin raw material (1-tetradecene) was obtained as the product AlphaPlus® 1-tetradecene from Chevron Phillips Chemical Company (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, phone number (800) 231-3260). The homogeneous cobalt organophosphate catalyst solution used in this example was a mixture containing 1.36 wt% cobalt(II) 2-ethylhexanoate (65% solution), 16.44 wt% tris(2,4-di-t-butylphenyl) phosphite ligand, and 82.2 wt% Synfluid® PAO4 cSt (Chevron Phillips Chemical Company) inert solvent. This mixture was heated at 150 °C for 2 hours with stirring in the presence of a nitrogen atmosphere to produce an active cobalt catalyst solution (cobalt 1500 ppm, P:Co molar ratio = 10). The starting reaction mixture was composed of 53.3 wt% C14 linear α-olefin raw material and 46.7 wt% active cobalt catalyst solution.

[0414] Using a starting reaction mixture having a cobalt concentration of 700 ppm, the mixture was placed in a high-pressure stainless steel autoclave and the reaction was carried out in a batch process. The C14 α-olefin feed mixture was isomerized at 180 °C for 3 hours under a CO / H2 atmosphere at a pressure of 20 bar(g). The isomerized olefin mixture was then hydroformylated at 180 °C for 3 hours under a CO / H2 atmosphere at a pressure of 60 bar(g). The molar ratio of CO to H2 in both the isomerization step and the hydroformylation step was 1:1.1. The conversion of the starting olefin to aldehyde and alcohol products was 69.6%. The resulting hydroformylation reaction product contained a mixture of C15 aldehydes and C15 alcohols. The isomer distribution of the mixture of C15 aldehydes and C15 alcohols was as follows. C15 aldehyde 1-pentadecanal 30.2% 2-methyltetradecanal 13.2% 2-ethyltridecanal 6.2% 2-propyl-dodecanal 4.8% 2-Butyl / 2-Pentyl / 2-Hexyl Isomer 13.8% Total C15 Aldehydes: 68.2% C15 Alcohol 1-Pentadecanol 18.9% 2-Methyltetradecanol 8.7% 2-Ethyltridecanol 1.8% 2-Propyl / 2-Butyl / 2-Pentyl / 2-Hexyl Isomer 2.4% Total C15 Alcohols: 31.8%

[0415] The weight percentage of the straight-chain rate of the C15 aldehyde / alcohol mixture was 49.1%. The weight percentage of the branched rate of the C15 aldehyde / alcohol mixture was 50.9%. The weight percentage of the 2-methyl isomer of the C15 aldehyde / alcohol mixture was 21.9%. The weight percentage of the 2-ethyl isomer of the C15 aldehyde / alcohol mixture was 8.0%. The total weight percentage of the 2-propyl / 2-butyl / 2-pentyl / 2-hexyl isomers of the C15 aldehyde / alcohol mixture was 21.0%.

[0416] <Example 9: Production of Branched C15 Aldehydes / C15 Alcohol Products Using a Cobalt-Rhodium Mixed Catalyst>

[0417] The C14 linear α-olefin raw material (1-tetradecene) was obtained as the product AlphaPlus® 1-tetradecene from Chevron Phillips Chemical Company (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, phone number (800) 231-3260). As the homogeneous cobalt-rhodium organophosphorus catalyst solution for this example, a mixture containing 1.36 wt% cobalt(II) 2-ethylhexanoate (65% solution), 0.005 wt% Rh(CO)2ACAC (rhodium(I) dicarbonyl acetylacetonate), 16.44 wt% tris(2,4-di-t-butylphenyl) phosphite ligand, and 82.2 wt% Synfluid® PAO4cSt (Chevron Phillips Chemical Company, P.O. Box 4910, The Woodlands, TX 77387-4910, USA, phone number (800) 231-3260) inert solvent was used. This mixture was heated at 150 °C for 2 hours with stirring in the presence of a nitrogen atmosphere to produce an active cobalt-rhodium catalyst solution (cobalt 1500 ppm, P:Co molar ratio = 10, rhodium 21 ppm). The starting reaction mixture contained 53.3 wt% C14 linear α-olefin raw material and 46.7 wt% active cobalt-rhodium catalyst solution.

[0418] Using a starting reaction mixture having a cobalt concentration of 700 ppm and a rhodium concentration of 10 ppm, the mixture was placed in a high-pressure stainless steel autoclave and the reaction was carried out in a batch process. The C14α-olefin feed mixture was isomerized at 80 °C for 1.5 hours under a CO / H2 atmosphere at a pressure of 2 bar(g). The isomerized olefin mixture was then hydroformylated at 180 °C for 2.5 hours under a CO / H2 atmosphere at a pressure of 30 bar(g). The molar ratio of CO to H2 in both the isomerization step and the hydroformylation step was 1:1.1. The conversion of the starting olefin to aldehyde and alcohol products was 83.0%. The hydroformylation reaction product obtained contained a mixture of C15 aldehydes and C15 alcohols. The isomer distribution of the mixture of C15 aldehydes and C15 alcohols was as follows. C15 Aldehyde 1-Pentadecanal 29.2% 2-Methyltetradecanal 35.3% 2-Ethyltridecanal 8.9% 2-Propyl-dodecanal 5.3% 2-Butyl / 2-Pentyl / 2-Hexyl Isomers 12.3% Total C15 Aldehyde: 91.0% C15 Alcohol 1-Pentadecanol 4.1% 2-Methyltetradecanol 3.8% 2-Ethyltridecanol 0.8% 2-Propyl / 2-Butyl / 2-Pentyl / 2-Hexyl Isomers 0.3% Total C15 Alcohol: 9.0%

[0419] The weight percentage of the linearity of the C15 aldehyde / alcohol mixture was 33.3%. The weight percentage of the branching of the C15 aldehyde / alcohol mixture was 66.7%. The weight percentage of the 2-methyl isomer of the C15 aldehyde / alcohol mixture was 39.1%. The weight percentage of the 2-ethyl isomer of the C15 aldehyde / alcohol mixture was 9.7%. The total weight percentage of the 2-propyl / 2-butyl / 2-pentyl / 2-hexyl isomers of the C15 aldehyde / alcohol mixture was 18.0%.

[0420] (Downstream Products)

[0421] In one embodiment, a method for producing a branched aldehyde intermediate and / or a branched aldehyde intermediate composition includes providing a first catalyst comprising an organometallic complex having at least one of rhodium and cobalt and at least one organic phosphorus ligand, providing one or more C4-C36 linear α-olefins, providing a gas phase containing CO, isomerizing the linear α-olefin with the first catalyst at a first pressure in the presence of CO to produce an isomerized olefin, and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde intermediate composition.

[0422] In one embodiment, a method for producing a branched aldehyde intermediate can produce a branched product composition including at least one of a branched alcohol composition, a branched surfactant composition, a branched amine composition, a branched amine oxide composition, a branched carboxylic acid composition, a branched aldehyde composition, a branched ester composition, a branched alkyl sulfate composition, a branched alcohol alkoxylate composition, a branched alcohol alkoxylate sulfate composition, a branched cyanohydrin composition, a branched aldol condensate composition, a branched hydrate composition, a branched hemiacetal composition, and a branched acetal composition through further reactions such as a hydrogenation reaction, a surfactant formation reaction, and other chemical derivative formation reactions.

[0423] In one embodiment, a method for producing a branched aldehyde further includes generating a product composition including at least one of a branched alcohol composition, a branched surfactant composition, a branched amine composition, a branched amine oxide composition, a branched carboxylic acid composition, a branched aldehyde acid composition, a branched ester composition, a branched alkyl sulfate composition, a branched alcohol alkoxylate composition, a branched alcohol alkoxylate sulfate composition, a branched cyanohydrin composition, a branched aldol condensate composition, a branched hydrate composition, a branched hemiacetal composition, and a branched acetal composition based on the reaction of the branched aldehyde intermediate composition.

[0424] In one embodiment, the method for producing a branched aldehyde further includes the step of producing at least one of the following products containing a product composition: detergents, cleaning agents, shampoos, emulsifiers, creams, lotions, toothpastes, wetting agents, cosmetics, personal care products, soaps, laundry detergents, dishwashing detergents, shower gels, hair conditioners, fabric softeners, papers, oils, fragrances, fragrance components, perfumes, essential oils, organic solvents, synthetic pheromones, explosives, plastics, hand sanitizers, pharmaceuticals, flavorings and / or fixatives, catalysts, base catalysts, acid catalysts, plasticizers, flame retardants, engine oils, oil additives, insecticides, pesticides, foods, beverages, adhesives, sealants, paints, stains, coating agents, inks, nail polishes, pharmaceutical compositions, lubricants, lubricant additives, polymer additives, coating additives, antioxidants, polymers, copolymers, polymer modifiers, polyols, corrosion inhibitors, viscosity modifiers, coupling agents, thickeners, greases, fragrances, skin care products, laundry detergents, dishwashing detergents, hand washing soaps, household cleaning agents, industrial cleaning agents, floor cleaners, car wash soaps, engine degreasers, foaming agents, wetting agents, oilfield drilling oils, petroleum enhanced recovery agents, surfactants, nonionic surfactants, anionic surfactants.

[0425] In one embodiment, the method for producing a branched aldehyde further includes the step of using the product composition in at least one of the processes of oil production, oilfield drilling, petroleum enhanced recovery, automobile production, aircraft production, metal processing, lubricating oil production, polymer production, degreasing, cleaning, dishwashing, laundry washing, medical treatment, and coating.

[0426] In one embodiment, the method includes providing a first catalyst comprising an organometallic complex having at least one of rhodium and cobalt and at least one organic phosphorus ligand; providing one or more C4-C36 linear α-olefins; providing a gas phase containing CO; isomerizing the linear α-olefin with the first catalyst at a first pressure in the presence of CO to produce an isomerized olefin; and hydroformylating the isomerized olefin with the first catalyst at a second pressure different from the first pressure in the presence of CO and H2 to produce a branched aldehyde intermediate composition. Further, the method may further include reacting the branched aldehyde intermediate composition by a hydrogenation reaction, a surfactant formation reaction, and other chemical derivative formation reactions to produce a branched product composition including at least one of a branched alcohol composition, a branched surfactant composition, a branched amine composition, a branched amine oxide composition, a branched carboxylic acid composition, a branched ester composition, a branched alkyl sulfate composition, a branched alcohol alkoxylate composition, a branched alcohol alkoxylate sulfate composition, a branched cyanohydrin composition, a branched aldol condensate composition, a branched hydrate composition, a branched hemiacetal composition, and a branched acetal composition.The method may further include the step of manufacturing at least one of the following products comprising a branched product composition: detergents, cleaning agents, shampoos, emulsifiers, creams, lotions, toothpastes, wetting agents, cosmetics, personal care products, soaps, laundry detergents, dishwashing detergents, shower gels, hair conditioners, fabric softeners, paper, oils, fragrances, fragrance components, perfumes, essential oils, organic solvents, synthetic pheromones, explosives, plastics, hand disinfectants, pharmaceuticals, flavorings and / or fixatives, catalysts, base catalysts, acid catalysts, plasticizers, flame retardants, engine oils, oil additives, insecticides, pesticides, foods, beverages, adhesives, sealants, paints, stains, coating agents, inks, nail polishes, pharmaceutical compositions, lubricants, lubricant additives, polymer additives, coating additives, antioxidants, polymers, copolymers, polymer modifiers, polyols, corrosion inhibitors, viscosity modifiers, coupling agents, thickeners, greases, fragrances, skin care products, laundry detergents, dishwashing detergents, hand washing soaps, household cleaning agents, industrial cleaning agents, floor cleaners, car wash soaps, engine degreasers, foaming agents, wetting agents, oil field drilling oils, oil recovery enhancers, surfactants, nonionic surfactants, anionic surfactants. The method may further include the step of using the branched product composition in at least one of the processes of oil production, oil field drilling, oil recovery enhancement, automobile production, aircraft production, metal processing, lubricating oil manufacturing, polymer manufacturing, degreasing, cleaning, dishwashing, laundry washing, medical treatment, and coating.

[0427] (Conclusion)

[0428] The present disclosure relates, in many of its aspects, features, and elements, to branched products and methods for producing and manufacturing branched products. Such compounds and manufacturing processes can be dynamic in their use and operation. The present disclosure is intended to encompass equivalents, means, systems, methods of using branched products, methods for producing and manufacturing branched products, and many of their aspects that are consistent with the description and spirit of the apparatus, means, methods, functions, operations disclosed herein. Other embodiments and modifications will be apparent to those skilled in the art and will be recognized as being within the scope of the present disclosure.

[0429] The scope of the present disclosure is to be interpreted broadly. The embodiments herein can be used together, separately, mixed, or combined. The present disclosure is intended to disclose the devices, designs, operations, control systems, controls, activities, mechanical actions, mechanics, and equivalents, means, systems, and methods for achieving the results disclosed herein. For each of the disclosed compounds, processes, methods, manufacturing methods, mechanical elements, or mechanisms, the present disclosure also intends to include and teach equivalents, means, systems, and methods for realizing many aspects, compounds, processes, mechanisms, and devices disclosed herein within its scope of disclosure. The claims of the present application are to be interpreted broadly as well.

[0430] The description of the technology herein is merely exemplary in many of its various embodiments, and variations within the scope not departing from the gist of the present disclosure are intended to be included within the scope of the claims and the disclosure. Such variations should not be regarded as departing from the spirit and scope of the disclosed technology.

[0431] It will be understood that various modifications and changes can be made to the above-described embodiments of the methods and the resulting branched products disclosed herein without departing from the spirit and scope of the claims.

Claims

1. A composition comprising a mixture of C9-C35 aldehydes, less than 60 wt% of the mixture of C9-C35 aldehydes is a linear aldehyde, more than 25 wt% of the mixture of C9-C35 aldehydes is a 2-methyl branched aldehyde, more than 8 wt% of the mixture of C9-C35 aldehydes is a 2-ethyl branched aldehyde, and the composition has a freezing point of the mixture of C9-C35 aldehydes of less than -10°C.

2. The composition according to claim 1, wherein the freezing point of the mixture of C9-C35 aldehydes is less than -20°C.

3. The composition according to claim 1, wherein the freezing point of the mixture of C9-C35 aldehydes is less than -30°C.

4. The composition according to claim 1, wherein the freezing point of the mixture of C9-C35 aldehydes is less than -40°C.

5. The composition according to claim 1, wherein the freezing point of the mixture of C9-C35 aldehydes is less than -60°C.

6. The composition according to claim 1, wherein the freezing point of the mixture of C9-C35 aldehydes is less than -80°C.

7. The composition according to claim 1, wherein the freezing point of the mixture of C9-C35 aldehydes is less than -100°C.

8. A composition comprising a mixture of C9-C35 alcohols, less than 60 wt% of the mixture of C9-C35 alcohols is a linear alcohol, more than 25 wt% of the mixture of C9-C35 alcohols is a 2-methyl branched alcohol, more than 8 wt% of the mixture of C9-C35 alcohols is a 2-ethyl branched alcohol, A composition in which the freezing point of the mixture of C9 - C35 alcohols is less than -10°C.

9. The composition according to claim 8, wherein the freezing point of the mixture of C9 - C35 alcohols is less than -20°C.

10. The composition according to claim 8, wherein the freezing point of the mixture of C9 - C35 alcohols is less than -30°C.

11. The composition according to claim 8, wherein the freezing point of the mixture of C9 - C35 alcohols is less than -40°C.

12. The composition according to claim 8, wherein the freezing point of the mixture of C9 - C35 alcohols is less than -60°C.

13. The composition according to claim 8, wherein the freezing point of the mixture of C9 - C35 alcohols is less than -80°C.

14. The composition according to claim 8, wherein the freezing point of the mixture of C9 - C35 alcohols is less than -100°C.

15. A step of reacting a mixture of C8 - C36 alcohols with a sulfating agent, and A step of producing a resulting alkyl sulfate composition, which is a resulting alkyl sulfate composition produced as a product of a method comprising: Less than 60% of the mixture of C8 - C36 alcohols is a linear alcohol, More than 25% of the mixture of C8 - C36 alcohols is a 2-methyl branched alcohol, A resulting alkyl sulfate composition in which more than 8% of the mixture of C8 - C36 alcohols is a 2-ethyl branched alcohol.

16. The resulting alkyl sulfate composition according to claim 15, wherein the alkyl sulfate mixture comprises a surfactant composition.

17. The produced alkyl sulfate composition according to claim 15, wherein more than 10% of the mixture of the C8-C36 alcohols is a 2-ethyl-branched alcohol. **Claim 18** The produced alkyl sulfate composition according to claim 15, wherein more than 12% of the mixture of the C8-C36 alcohols is a 2-ethyl-branched alcohol. **Claim 19** The produced alkyl sulfate composition according to claim 15, wherein more than 16% of the mixture of the C8-C36 alcohols is a 2-ethyl-branched alcohol. **Claim 20** The produced alkyl sulfate composition according to claim 15, wherein more than 20% of the mixture of the C8-C36 alcohols is a 2-ethyl-branched alcohol.

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