Method for producing alkoxylated etheramines and uses thereof

Abstract

A process for preparing alkoxylated ether amines, comprising: carrying out an alkoxylation reaction between a Guerbet alcohol and an epoxide in the presence of a catalyst to obtain an alkoxylated alcohol, which is then subjected to an amination reaction in the presence of ammonia and hydrogen to form an alkoxylated Guerbet amine.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Application No. 63 / 254,552, filed October 12, 2021. The aforementioned application is incorporated herein by reference.

[0002] Technical Field The present disclosure generally relates to a process for obtaining alkoxylated ether primary amines. More specifically, the present disclosure relates to a two-step process for producing alkoxylated ether amines, which includes reacting a primary alcohol with an epoxide and amminating the alkoxylated alcohol product with ammonia and hydrogen. [Background technology]

[0003] Fatty primary amines and alkoxylated alkyl ether primary amines are well known as excellent building blocks for the manufacture of various products used as emulsifiers, corrosion inhibitors, fuel and lubrication additives, or agricultural chemical adjuvants. Various polyether amines can be prepared by reductive amination of alkoxylated aliphatic and aromatic alcohols. Methods for the manufacture of fatty primary amines from Guerbet alcohols have been previously discussed. See, for example, U.S. Pat. No. 5,399,633. However, primary amines produced in such a manner tend to lack flexibility for end-use applications. U.S. Pat. No. 5,499,493, U.S. Pat. No. 5,499,623, U.S. Pat. No. 5,523,366, and U.S. Pat. No. 5,523,637 disclose methods for the manufacture of Guerbet alkyl ether amines with the aim of avoiding the problems associated with the above-mentioned fatty primary amines. However, each of the above patent references discloses a two-step process involving cyanoethylation or cyanobutylation of alkoxylated Guerbet alcohols, followed by hydrogenation of the corresponding nitriles.

[0004] Despite the current state of the art, there is a continuing need to develop primary amines that allow for chain extension and flexible hydrophobicity. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] U.S. Patent No. 5,808,158 [Patent Document 2] U.S. Patent No. 5,094,667 [Patent Document 3] U.S. Patent No. 5,264,006 [Patent Document 4] U.S. Patent No. 5,298,038 [Patent Document 5] U.S. Patent No. 6,114,585 Summary of the Invention

[0006] Before describing aspects of the present disclosure in detail, it is to be understood that the present disclosure is not limited in its application to the details of construction and arrangement of components or steps or methods set forth in the following description. The present disclosure is capable of other embodiments or of being practiced or carried out in various ways. It is also to be understood that the phraseology and terms employed herein are for the purpose of description and should not be construed as limiting.

[0007] Unless otherwise defined herein, technical terms used in connection with the present disclosure shall have the meanings that are commonly interpreted by those of ordinary skill in the art. Further, unless otherwise required by context, singular terms shall include pluralities and plural terms shall include the singular.

[0008] All patents, published patent applications, and non-patent publications mentioned herein are incorporated by reference in their entirety to which this disclosure pertains. All patents, published patent applications, and non-patent publications referenced anywhere in this application are expressly incorporated by reference in their entirety herein to the same extent as if each individual patent or publication was specifically and individually indicated to be incorporated by reference unless inconsistent with this disclosure.

[0009] All of the compositions and / or methods disclosed herein can be made and executed without undue experimentation in light of the present disclosure. Although the compositions and methods of the present disclosure have been described in terms of preferred embodiments, it will be apparent to those skilled in the art that modifications can be applied to the compositions and / or methods described herein, and to the steps or sequence of steps of the methods, without departing from the concept, spirit, and scope of the present disclosure. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the concept, spirit, and scope of the present disclosure.

[0010] As used in accordance with the present disclosure, the following terms, unless otherwise indicated, shall be understood to have the following meanings:

[0011] The use of the words "a" or "an," when used in conjunction with the terms "comprising," "including," "having," or "containing" (or variations of such terms), can mean "one," but is not inconsistent with the meanings of "one or more," "at least one," and "one or more than one."

[0012] Use of the term "or" is used to mean "and / or," unless expressly stated to refer only to alternatives and only where the alternatives are mutually exclusive.

[0013] Whenever "may," "can," "could," or "might" is used in this specification to describe that a certain element or feature is included or has a certain characteristic, it does not require that the particular element or feature be included or have the certain characteristic.

[0014] Throughout this disclosure, the term "about" is used to indicate that a value includes the inherent variation of error of a quantification device, mechanism, or method, or includes the inherent variation that exists among the subject(s) being measured. By way of example, and not limitation, when the term "about" is used, the specified value to which it refers can vary by plus or minus 10%, or 9%, or 8%, or 7%, or 6%, or 5%, or 4%, or 3%, or 2%, or 1%, or one or more fractions therebetween.

[0015] The use of "at least one" is to be interpreted as including one as well as any amount greater than one, including, but not limited to, 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term "at least one" can extend up to 100 or up to 1000 or more, depending on the term to which it refers. Also, the amount 100 / 1000 should not be interpreted as a limit, since a lower or higher limit can also yield satisfactory results.

[0016] Additionally, the phrase "at least one of X, Y, and Z" shall be interpreted to include X alone, Y alone, and Z alone, as well as any combination of X, Y, and Z. Similarly, the phrase "at least one of X and Y" shall be interpreted to include X alone, Y alone, and any combination of X and Y. It should also be appreciated that the phrase "at least one of" may be used with any number of elements and may include any of the elements set forth above. has the same meaning as

[0017] The use of ordinal terminology (i.e., "first," "second," "third," "fourth," etc.) is merely for the purpose of distinguishing between two or more items and, unless specifically stated, does not imply any ordering, ranking, or importance of one item relative to another item, nor does it imply any additional order of preference.

[0018] As used herein, the words "comprising" (and any form thereof, e.g., "comprise" and "comprises"), "having" (and any form thereof, e.g., "have" and "has"), "including" (and any form thereof, e.g., "includes" and "include"), or "containing" (and any form thereof, e.g., "contains" and "contain") are inclusive or open-ended and do not exclude additional, unrecited elements or method steps.

[0019] The phrases "or combinations thereof" and "and combinations thereof" when used herein refer to all permutations and combinations of the items listed preceding the term. For example, "A, B, C, or combinations thereof" is intended to include at least one of the following: A, B, C, AB, AC, BC, or ABC, and also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB, if the order is important in the particular situation. Continuing with this example, combinations including repeats of one or more items or terms, e.g., BB, AAA, CC, AABB, AACC, ABCCCC, CBBAAA, CABBB, etc., are also expressly included. As will be appreciated by those of skill in the art, there is typically no limit to the number of items or terms in any combination unless otherwise clear from the context. In the same spirit, the term "and combinations thereof" when used with the phrase "selected from the group consisting of" refers to all permutations and combinations of the items listed preceding the phrase.

[0020] Phrases such as "in one embodiment," "in an embodiment," "according to one embodiment," and the like generally mean that the particular feature, structure, or characteristic that follows the phrase is included in at least one embodiment of the disclosure, and may be included in more than one embodiment of the disclosure. Importantly, such phrases are open-ended and do not necessarily refer to the same embodiment, but rather, of course, can refer to one or more prior and / or subsequent embodiments. For example, in the appended claims, any of the claimed embodiments can be used in any combination.

[0021] As used herein, the terms "weight %", "wt%", "weight percentage", or "percentage by weight" are used interchangeably.

[0022] As used herein, the term "ambient temperature" refers to the temperature of the surrounding working environment (e.g., the temperature of the space, building, or room in which the curable composition is used), and does not include any temperature changes that result from directly heating the curable composition to promote curing. Ambient temperatures can typically be in the range of about 10°C to about 30°C, more specifically about 15°C to about 25°C.

[0023] As used herein, "surfactant" refers to a chemical compound that reduces the interfacial tension between two liquids.

[0024] The alkoxylated amine synthesis process as described herein can be carried out using a two-step process: (i) an alkoxylation reaction between a primary alcohol and (ii) an epoxide, followed by reductive amination of the alkoxylated alcohol by reaction with (iii) ammonia and (iv) hydrogen.

[0025] In at least one example, the primary alcohol (i) of the first step of the two-step process can be a saturated primary alcohol having about 12 to about 40 carbon atoms. In at least one example, the primary alcohol can be a Guerbet alcohol. The term "Guerbet alcohol" as used herein refers to a branched-chain saturated primary alcohol. Such Guerbet alcohols can provide good lubricity, high flow range, low melting point, and high boiling point. For example, the melting point of Guerbet alcohols can be about 50°C to about 60°C lower than linear saturated alcohols with the same number of carbon atoms. Furthermore, Guerbet alcohols having up to 24 carbon atoms can be liquid at ambient temperatures, and alkoxylated surfactants derived from Guerbet alcohols can exhibit lower viscosities than those prepared from linear saturated alcohols having a comparable number of carbon atoms. Guerbet alcohols can include, but are not limited to, alcohols having the general structure of 2-alkyl-1-alkanol.

[0026] The epoxide (ii) in the first step can be any epoxide, including, but not limited to, ethylene oxide, propylene oxide, butylene oxide, pentylene oxide, and styrene oxide. The reaction of a primary alcohol with an epoxide can produce an alkoxylated primary alcohol, including, but not limited to, ethoxylated, propoxylated, butoxylated, and pentoxylated primary alcohols.

[0027] The chemical reaction (a) of the first step can be carried out in the presence of one or more catalysts. The catalyst used in the first step of the reaction can be any catalyst suitable for causing the reaction to occur, including, but not limited to, alkaline catalysts and / or heterogeneous catalysts. In at least one example, the catalyst can be selected from sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium methoxide (NaOMe), potassium methoxide (KOMe), ammonia (NH3), calcium oxide (CaO), calcium carbonate (CaCO3), double metal cyanide (DMC), and combinations thereof. The metals present in the DMC catalyst can include, but are not limited to, zirconium (Zn(II)), iron (Fe(II), Fe(III)), cobalt (Co(II), Co(III)), chromium (Cr(III)), iridium (Ir(III)), and combinations thereof.

[0028] The alkoxylation reaction can be carried out at a temperature of less than about 200° C. In at least one example, the alkoxylation reaction can be carried out at a temperature of less than about 165° C. In a further example, the alkoxylation reaction can be carried out at a temperature of less than about 140° C. In yet another example, the alkoxylation reaction can have a reaction temperature in the range of about 120° C. to about 125° C.

[0029] In the second step, an amination reaction can be carried out on the alkoxylated alcohol product of the first step. Specifically, the alkoxylated alcohol product can be reacted with ammonia (NH3) and hydrogen (H2) to obtain an alkoxylated alcohol amine. In at least one example, the amination reaction can be carried out in a batch process. In the alternative, the amination reaction can be carried out as a continuous reaction. A continuous process can avoid the additional filtration step required during the batch process amination. Additionally, excess ammonia produced during the reaction can be recovered and reused in a further continuous process. It can be used.

[0030] During the amination reaction, the flow rate of the alkoxylated primary alcohol can enter the reaction chamber at a rate greater than about 0.5 space velocity. As used herein, the term "space velocity" refers to the relationship between the volumetric flow rate and the reactor volume of the chemical reactor. In at least one example, the flow rate of the alkoxylated primary alcohol entering the reaction chamber can be from about 0.5 space velocity to about 1.5 space velocity. In an alternative example, the flow rate can be from about 0.5 space velocity to about 1.0 space velocity. The ammonia to hydrogen flow rate ratio can be from about 0.05 liters per hour (L / hr):1 gram (g) NH3 / h to 0.12 L / hr:1 g NH3 / h to 0.65 L / hr:1 g NH3 / h. The molar ratio of ammonia to alkoxylated primary alcohol in the amination reaction can range from about 8:1 NH3 to alcohol to about 100:1 NH3 to alcohol. In at least one example, the molar ratio can range from about 20:1 NH3 to alcohol to about 50:1 NH3 to alcohol.

[0031] To accelerate the amination of the alkoxylated alcohol, the reaction can be carried out in the presence of a catalyst. In at least one example, the catalyst present in the amination reaction can be a metal catalyst or a mixture of metal catalysts. The metal catalyst present in the amination reaction can be one or more metals, including, but not limited to, cobalt, copper, iridium, nickel, rhodium, ruthenium, zirconium, and / or their oxides. In at least one example, the catalyst can be supported on a silica bed, an alumina bed, or a graphite bed. In at least one example, the activity of the catalyst can be increased by activating it with hydrogen before being introduced into the amination reaction.

[0032] In at least one example, the amination reaction can be carried out under pressure. In at least one example, the amination reaction can be carried out at a temperature greater than about 100° C. In an alternative example, the amination reaction can be carried out at a temperature greater than about 130° C. In yet another alternative example, the amination reaction can be carried out at a temperature range of about 150° C. to about 250° C.

[0033] The pressure at which the amination reaction occurs ranges from about 1500 psig to about 2500 psig. In at least one embodiment, the reaction pressure is from about 1800 psig to about 2000 psig. The reaction temperature can range from about 150° C. to 250° C. In at least one embodiment, the temperature can range from about 180° C. to about 220° C.

[0034] The amination processes described herein can allow for high conversion of alcohols to amines. For example, the amination reaction processes described herein can provide higher selectivity for primary amines than prior processes involving cyanoethylation followed by hydrogenation.

[0035] The alkoxylated amines formed using the reactions described herein can be used in a variety of markets, including, but not limited to, agricultural chemicals, coatings, adhesives, industrial markets, gas processing, electronics, construction, composites, metal processing, mining, oil field chemicals, enhanced oil recovery, paper, polyurethane additives, polyurethane components, water, fuels, lubricants, and polymer modification.

[0036] Additionally, the alkoxylated amines can be used in a variety of applications, including but not limited to, household and personal care products (including but not limited to soaps, detergents, etc.), asphalt emulsions (as Di C10+ acetate salts), separations, and the like. Examples include dispersants (e.g., reacted into dispersant elements), as reagents for reverse flotation of iron ores (e.g., taconite), reacted into polymers to provide hydrophobic side chains (e.g., reacting C20-40 amines with maleic acid to make paraffin inhibitors), and as additives for various plastics (e.g., internal mold release agents).

[0037] Alkoxylated amines can further be used as initiators for alkoxylates, such initiators include, but are not limited to, C14-40 Guerbet amines and ethylene oxide / propylene oxide, or carboxylated ethylene oxide / propylene oxide, or sulfamated ethylene oxide / propylene oxide-ultra-low IFT surfactants for EOR; for ground water remediation (e.g., removal of NAPL non-aromatic contaminated liquids); for C12-24 and ethoxylation for agricultural chemical formulations (e.g., chemicals such as aggregated (SL) or in EC formulations); for octyl / decanol amines and ethoxylation as a replacement for oxtylphenol ethoxylates; as blowing agents for urethane foams; as anti-redeposition aids in detergents, fuel lubrication (e.g., friction modifiers), and the like.

[0038] Examples are provided below. However, the present disclosure should not be construed as being limited in its application to the specific experiments, results, and experimental procedures disclosed herein below. Instead, the examples are provided merely as one of various embodiments, and are meant to be illustrative and not comprehensive. EXAMPLES

[0039] To illustrate the two-step reaction described herein, the propoxylation of a Guerbet alcohol to form a propoxylated Guerbet amine product is illustrated below: [ka] wherein R1 and R2 are each independently selected from saturated alkyl chains having an integer number of carbons, x and y, where x+y is in the range of 14 to 36; DMC is a double metal cyanide catalyst as described in detail above; and n is an integer from 2 to 35.

[0040] The term "alkyl" as used herein includes both straight and branched chain groups as well as cyclic groups. In some examples, the alkyl groups R1 and R2 can have up to 40 carbons (in some embodiments, up to about 30, 20, 15, 12, 10, 8, 7, 6, 5, 4, 3, 2, or 1 carbons) unless otherwise specified. In at least one example, cyclic alkyl groups conforming to the above alkyl chains can be monocyclic and can have from about 3 to about 10 carbon atoms.

[0041] The above exemplary propoxylation reaction can include charging a Guerbet alcohol in the presence of a catalyst to a stainless steel kettle. The Guerbet alcohol can have from about 12 to about 40 carbon atoms. The reaction temperature can then be increased to about 120°C, and the resulting mixture can be dried under a nitrogen stream. About 2 to about 35 equivalents of propylene oxide can then be added while maintaining the reaction pressure at about 60 psi and the temperature at about 120°C to about 125°C. During the reaction, the pressure in the reaction chamber is allowed to fluctuate, and the temperature is increased to about 100°C. The temperature can be maintained in the range of 20° C. to about 125° C. The pressure can be adjusted by varying the propylene oxide flow into the reaction chamber. Once the pressure has dropped to less than about 1 psi for at least about 30 minutes, the mixture can be cooled and analyzed for hydroxyl number.

[0042] The second step of the exemplary reaction, as described above, involves reacting the propoxylated Guerbet alcohol with a stream of hydrogen (H2) and ammonia (NH3). The hydrogen flow can be varied to adjust the reaction pressure in the reaction chamber to the desired pressure. In at least one example, the desired pressure can range from about 1800 psig to about 2000 psig. The hydrogen flow is then further adjusted to a desired flow rate of about 2.6 L / hr to about 3.2 L / hr. The ammonia flow can enter the reaction chamber at a rate of about 50 g / hr.

[0043] The propoxylated Guerbet alcohol stream can enter the reaction chamber at a rate of about 50 g / hr to about 100 g / hr. In at least one example, the propoxylated Guerbet alcohol flow rate can be from about 50 g / hr to about 75 g / hr. After about 1 hour to about 2 hours of reaction time and once a steady state is achieved, the reaction product can be collected and tested for amine content.

[0044] If a catalyst is present, it may be activated by a hydrogen flow prior to entering the reaction chamber to accelerate the amination reaction. For example, a 100 mL stainless steel continuous reactor may be charged with 100 g of metal catalyst and activated under a hydrogen flow rate of about 50 L / hr for about 2 hours at a temperature of about 200° C. The temperature of the reaction chamber may then be adjusted to a desired range. In at least one example, the desired temperature range may be from about 180° C. to about 220° C. In a further example, the desired temperature range may be from about 200° C. to about 210° C.

[0045] In some cases, a portion of the crude product may remain after the reaction is completed. In at least one example, the remaining crude product can be charged into a glass reactor, and excess ammonia and water by-products can be removed under vacuum at a temperature of about 120° C. The purified crude product can then be recycled back to the beginning of the reaction.

[0046] Specific examples of exemplary propoxylation and amination reactions are provided below, which are not exhaustive and are not intended to, and do not, limit the scope of the disclosure herein.

[0047] Propoxylation Procedure for Guerbet Alcohols A clean, dry 4 gallon stainless steel kettle is charged with Guerbet alcohol and catalyst. If the catalyst is 45% potassium hydroxide (KOH), 6 mole percent (mol%) can be used. If the catalyst is DMC, 0.06 wt% can be used. The reaction temperature is then increased to 120°C with a combined nitrogen sparge of 6-8 scfh. The reaction is maintained at such conditions for 2 hours to remove traces of water. 2 to 35 equivalents of propylene oxide are then added while maintaining the reaction pressure below 60 psi and the reaction temperature at 120°C to 125°C. The reaction temperature is then maintained at 120-125°C until the pressure drops to less than 1 psi for 30 minutes. The remaining pressure is then vented to a scrubber and residual unreacted propylene oxide is removed by sparging with nitrogen at about 6 scfh for 30 minutes. The mixture is then cooled and analyzed to determine the hydroxyl number.

[0048] Amination Procedure for Propoxylated Guerbet Alcohols Approximately 100 g of metal catalyst is placed in a clean, dry 100 mL stainless steel tubular continuous reactor. The metal catalyst can be a metal or a mixture of metals, such as cobalt, , copper, iridium, nickel, rhodium, ruthenium, zirconium, and / or their oxides. Hydrogen is flowed into the reactor at a rate of 50 L / h and a temperature of 200° C. for 2 hours to activate the catalyst. The reaction temperature is then increased to 205° C. and the pressure is increased to 2000 psig with hydrogen. The hydrogen flow is then set to 3.1 L / h. Ammonia flow enters the reaction at a rate of 50 g / h. Propoxylated Guerbet alcohol flow enters the reaction at a flow rate of 75 g / h. After 2 hours, steady state is achieved so the product can be collected and analyzed for amine number. After the reaction, the crude product is charged to a glass reactor and excess ammonia and water by-product are removed under vacuum at 120° C.

[0049] The following comparative examples and examples were carried out to evaluate the methods described herein:

[0050] Example 1 ("E1"): Guerbet C16 and 5 Propylene Oxide Amine Following the propoxylation procedure as set forth above, Isofol 16 was reacted with 5 equivalents of propylene oxide in the presence of DMC. The resulting Guerbet + 5PO alcohol was then aminated following the procedure described above. Tests were performed after the propoxylation and amination steps to determine the hydroxyl and amine numbers. The results are presented in Table 1.

[0051] Example 2 ("E2"): Guerbet C16 and 10 Propylene Oxide Amines The same method as described in Example 1 was used, except Isofol 16 was reacted with 10 equivalents of propylene oxide in the presence of potassium hydroxide (KOH) catalyst. The propoxylated alcohol was then aminated as described above. Tests were performed after each step to determine the hydroxyl and amine numbers. The results are presented in Table 1.

[0052] Example 3 ("E3"): Guerbet C16 and 15 Propylene Oxide Amines The same method as described in Example 1 was used, except that Isofol was used in the presence of DMC. 16 was reacted with 15 equivalents of propylene oxide. The propoxylated alcohol was then aminated as described above. Tests were performed after each step to determine the hydroxyl and amine numbers. The results are presented in Table 1.

[0053] Example 4 ("E4"): Guerbet C18T and 5 Propylene Oxide Amine The same method as described in Example 1 was used, except that Isofol 18T was reacted with 5 equivalents of propylene oxide in the presence of DMC catalyst. Amination was then carried out as shown above. Tests were performed after each step to determine the hydroxyl number and amine number. The results are presented in Table 1.

[0054] Example 5 ("E5"): Guerbet C20 and 5 Propylene Oxide Amine The same method as described in Example 1 was used, except Isofol 20 was reacted with 5 equivalents of propylene oxide in the presence of DMC catalyst. Amination of propoxylated Guerbet alcohols was carried out as shown above. Tests were performed after each step to determine the hydroxyl and amine numbers. The results are presented in Table 1.

[0055] Example 6 ("E6"): Guerbet C28 and 5 Propylene Oxide Amine The same method as described in Example 1 was used, except that Jarcol 28 was reacted with 5 equivalents of propylene oxide in the presence of DMC catalyst. Amination of propoxylated Guerbet alcohols was carried out as shown above. Tests were performed after each step to determine the hydroxyl and amine numbers. The results are presented in Table 1. [Table 1]

[0056] The conversion of Guerbet alcohols to propoxylated amines is greater than 92% and the selectivity towards the formation of primary amines is greater than 98%.

[0057] From the foregoing description, it is apparent that the present disclosure is well adapted to carry out the objects and obtain the advantages mentioned herein as well as those inherent therein. While illustrative embodiments of the present disclosure have been described for purposes of disclosure, it will be appreciated that numerous modifications can be made which will be readily suggested to those skilled in the art and which can be effected without departing from the scope of the present disclosure and the appended claims.

Claims

1. 1. A process for preparing an alkoxylated etheramine, comprising: alkoxylating an alcohol with an epoxide in the presence of a catalyst to form an alkoxylated alcohol, wherein the alcohol is a Guerbet alcohol; and amminating the alkoxylated alcohol in the presence of ammonia and hydrogen to form an alkoxylated Guerbet amine; The process comprising:

2. The Guerbet alcohol has the following structure: 【Chemical 1】 In the formula, R 1 and R 2 is selected from saturated alkyl chains having integers x and y carbons, where x+y ranges from about 14 to about 36; The process of claim 1.

3. 10. The process of claim 1, wherein the epoxide is selected from ethylene oxide, propylene oxide, butylene oxide, pentylene oxide, and styrene oxide.

4. 10. The process of claim 1, further comprising varying the epoxide flow rate during said alkoxylation.

5. 10. The process of claim 1, wherein the Guerbet alcohol has from about 12 to about 40 carbon atoms.

6. 2. The process of claim 1, wherein the alkoxylation reaction is carried out in the presence of one or more catalysts, the one or more catalysts being selected from sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium methoxide (NaOMe), potassium methoxide (KOMe), ammonia (NH3), calcium oxide (CaO), calcium carbonate (CaCO3), double metal cyanide (DMC), and combinations thereof.

7. 10. The process of claim 1, wherein the alkoxylation is carried out at a temperature of less than about 200°C.

8. 10. The process of claim 1, wherein the amination is carried out as one of a batch reaction or a continuous reaction.

9. 10. The process of claim 1, wherein the amination occurs in a reaction chamber and the alkoxylated primary alcohol enters the reaction chamber at a rate greater than about 0.5 space velocity.

10. The molar ratio of ammonia to alkoxylated primary alcohol during the amination is about 8:1 NH 3 NH to alcohol ratio of about 100:1 3 The process of claim 1, wherein the range is relative to the alcohol.

11. 10. The process of claim 1, wherein the amination is carried out in the presence of a catalyst selected from a metal catalyst or a mixture of metal catalysts.

12. 10. The process of claim 1, wherein the amination is conducted at a temperature above about 100° C. and a pressure of about 1500 psig to about 2500 psig.

13. The alkoxylated Guerbet amine is obtained by alkoxylating a Guerbet alcohol with an epoxide in the presence of a catalyst to form an alkoxylated Guerbet alcohol, and amminating the alkoxylated Guerbet alcohol in the presence of ammonia and hydrogen to form an alkoxylated Guerbet amine.

14. 14. The alkoxylated Guerbet amine of claim 13, wherein the epoxide is propylene oxide.

15. 15. The alkoxylated Guerbet amine of claim 14, wherein the conversion of the Guerbet alcohol to propoxylated amine is greater than 92% and the selectivity towards the formation of primary amines is greater than 98%.

16. The Guerbet alcohol has the following structure: 【Chemistry 2】 In the formula, R 1 and R 2 is selected from saturated alkyl chains having integers x and y carbons, where x+y ranges from about 14 to about 36; The alkoxylated Guerbet amine of claim 13.

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