Metalworking fluid compositions including 3-amino-2-butanol and uses thereof

Abstract

The present technology relates generally to metalworking fluid compositions including 3-amino-2-butanol. For example, including 3-amino-2-butanol in a metalworking fluid having a pH of at least about 7 may enhance the metalworking fluid's lubricating, cleaning, and / or handling properties by providing multi-metal corrosion inhibition, maintaining pH control, and / or stabilizing the metalworking fluid.

Description

[0001] Atty. Dkt. No.: 109691-0781 METALWORKING FLUID COMPOSITIONS INCLUDING 3-AMINO-2- BUTANOL AND USES THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS [1] This application claims the benefit of and priority to U.S. Provisional Appl. No. 63 / 633,640, filed April 12, 2024, which is incorporated herein by reference in its entirety for any and all purposes. TECHNICAL FIELD [2] The present technology relates generally to metalworking fluid compositions including 3-amino-2-butanol, useful for various metalworking operations (e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, protecting, and the like) of various metals. For example, including 3-amino-2-butanol in a metalworking fluid having a pH of at least about 7 enhances the metalworking fluid’s lubricating, cleaning, and handling properties by providing multi-metal corrosion inhibition, maintaining pH control, and stabilizing the metalworking fluid. BACKGROUND [3] Many commonly used metalworking fluids are made of compositions using chemicals typically derived from non-renewable raw materials such as petroleum. For example, in addition to the petroleum distillates that are in neat oils and semisynthetic metalworking fluids and surfactants in metalworking fluids are also typically derived from petroleum sources, including neutralizing agents meant to neutralize acid groups present in the composition. [4] Using non-renewable, petroleum-based raw materials contributes to overreliance on fossil fuels. This reliance on non-renewable petroleum-based raw materials contributes to environmental degradation such as air pollution, water pollution, and global warming. Moreover, these fossil fuels are often supplied from politically unstable parts of the world, often raising humanitarian concerns. -1- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 [5] Thus, as explained above and in more details below, there remains a need for compositions for commonly used metalworking fluids made with natural, renewable starting materials that offer equivalent or better performance to current products. SUMMARY [6] The present disclosure is directed to compositions for metalworking fluids for various metalworking operations (e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, protecting, and the like) of various metals, such as aluminum, steel, and copper, where such compositions include 3-amino-2-butanol (“3-AB”, also known as 3-amino-butan-2-ol; CAS No.: 42551-55-3). 3-Amino-2-butanol has several advantages, including its improved sustainability profile, demonstrated by its ability to be manufactured as a renewable, biobased compound (i.e., without relying on non- renewable petroleum-based raw materials) alongside its low toxicity (providing a safer alternative with reduced environmental and health impacts) while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NH3, NaOH). Thus, the presently disclosed technology overcomes common adoption barriers associated with renewable chemicals, such as poor performance and high cost, instead providing a high- performance, cost-effective solution with the potential for incorporating bio-based carbon. BRIEF DESCRIPTION OF THE DRAWINGS [7] FIGS.1A-1B provide results of droplet size and polydispersity index (PDI) characterization of 5 wt.% oil-in-water emulsions, where the oil phase was the metalworking fluid composition including 3-amino-2-butanol (“3AB”, of the present technology), ), 2- amino-2-methyl-1-propanol (“AMP”), monoisopropanolamine (“MIPA”), or monoethanolamine (“MEA”), per the working examples. FIG.1A illustrates that 3AB was found to provide significantly smaller droplet size as compared to AMP, MIPA, and MEA. FIG.1B illustrates that 3AB was found to provide significantly narrower PDI as compared to AMP, MIPA, and MEA. [8] FIG.2 provides results of pH buffering of metalworking fluid compositions including 0.1 M 3-amino-2-butanol (“3AB”, of the present technology), 2-amino-2-methyl-1-propanol -2- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 (“AMP”), monoisopropanolamine (“MIPA”), or monoethanolamine (“MEA”) titrated with 0.1 M lactic acid. It was found that 3AB provided significantly better buffering against acidification as compared to MIPA or MEA, and comparable buffering as compared to AMP, at least up through 40 mL addition of 0.1 M lactic acid solution. [9] FIG.3 demonstrates cobalt leaching control exhibited by 3-amino-2-butanol (“3AB”, of the present technology), 2-amino-2-methyl-1-propanol (“AMP”), monoisopropanolamine (“MIPA”), and monoethanolamine (“MEA”), per the working examples. FIG.3 illustrates that 3AB was found to provide significantly superior cobalt leaching control as compared to MIPA and MEA, and comparable cobalt leaching control as compared to AMP.

[0010] FIG.4 provides results of testing metalworking fluid compositions including 0.1 M 3- amino-2-butanol (“3AB”, of the present technology), 2-amino-2-methyl-1-propanol (“AMP”), monoisopropanolamine (“MIPA”), or monoethanolamine (“MEA”) inhibition of aluminum staining. As shown in FIG.4, 3AB provided comparable or better aluminum staining inhibition than AMP, MIPA, and MEA, across all alloy types. DETAILED DESCRIPTION

[0011] The following terms are used throughout as defined below.

[0012] As used herein and in the appended claims, singular articles such as “a” and “an” and “the” and similar referents in the context of describing the elements (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., “such as”) provided herein, is intended merely to better illuminate the embodiments and does not pose a limitation on the scope of the claims unless otherwise -3- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 stated. No language in the specification should be construed as indicating any non-claimed element as essential.

[0013] As used herein, “about” will be understood by persons of ordinary skill in the art and will vary to some extent depending upon the context in which it is used. If there are uses of the term which are not clear to persons of ordinary skill in the art, given the context in which it is used, “about” will mean up to plus or minus 10% of the particular term – for example, “about 10 wt%” would be understood to mean “9 wt% to 11 wt%.” It is to be understood that when “about” precedes a term, the term is to be construed as disclosing “about” the term as well as the term without modification by “about” – for example, “about 10 wt%” discloses “9 wt% to 11 wt%” as well as disclosing “10 wt%.”

[0014] The phrase “and / or” as used in the present disclosure will be understood to mean any one of the recited members individually or a combination of any two or more thereof – for example, “A, B, and / or C” would mean “A or B or C; A and B; A and C; B and C; or the combination of A, B, and C.”

[0015] The term "alkyl" refers to a group, whether alone or as part of another group (e.g., in dialkylamino), encompasses straight and branched chain aliphatic groups (i.e., saturated hydrocarbyl chains), and, unless otherwise indicated, has 1-10, alternatively 1-8, or alternatively 1-6 alkyl carbon atoms. Representative alkyl groups include, without limitation, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl. Unless otherwise indicated, the alkyl group is optionally substituted with 1, 2, or 3, e.g., 1 or 2, or even just 1, substituent(s) that are compatible with the compounds, monomers, and polymers described herein. In some embodiments, the alkyl group is unsubstituted.

[0016] The term "alkoxy" refers to a group in which an oxygen attached to a saturated straight or branched chain alkyl group. Unless otherwise indicated, the alkoxy group contains 1 to 6 carbon atoms (e.g. methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso- butoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentyloxy, iso-pentyloxy, n-hexyloxy or iso- hexyloxy), and in any embodiments, 1 to 4 carbon atoms. In any embodiments, the alkoxy groups include methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy. In some embodiments, the alkoxy group is unsubstituted. -4- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0017] Groups described herein having two or more points of attachment (i.e., divalent, trivalent, or polyvalent) within the compound of the present technology are designated by use of the suffix, “ene.” For example, divalent alkyl groups are alkylene groups, divalent cycloalkyl groups are cycloalkylene groups, and so forth. Substituted groups having a single point of attachment to the compound of the present technology are not referred to using the “ene” designation. Thus, e.g., chloroethyl is not referred to herein as chloroethylene.

[0018] In general, “substituted” refers to an alkyl group, as defined above in which one or more bonds to a hydrogen atom contained therein are replaced by a bond to non-hydrogen or non-carbon atoms. Substituted groups also include groups in which one or more bonds to a carbon(s) or hydrogen(s) atom are replaced by one or more bonds, including double or triple bonds, to a heteroatom. In some embodiments, a substituted group is substituted with 1, 2, or 3 substituents. Examples of substituent groups include, but are not limited to, hydroxyl, amino, thiol, nitro, halo, ester, amido, carbonyl, or carboxylic acid. Unless otherwise indicated, the foregoing substituent groups are not themselves further substituted.

[0019] Unless stated otherwise, all the molecular weight (i.e., molar mass) data, number- average molecular weight data Mn or weight-average molecular weight data Mw stated in the present description are molar masses, which can be determined by gel permeation chromatography (GPC).

[0020] As used herein, “substantially free” refers to less than about 2 wt% of the specified component based on the total weight of the composition. In some embodiments, the composition may include less than about 1 wt%, less than about 0.5 wt%, or less than about 0.1 wt% of the specified component. In some embodiments, the composition may be free of detectable amounts of the component. 3-Amino-2-Butanol (“3-AB”) Compositions

[0021] In an aspect, the present technology provides a composition for use in metalworking fluids and metalworking applications, such as for use in e.g., metal removal, metal forming, metal cleaning, and / or metal treating, and such as for use in e.g., cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and / or protecting of a metal and / or metal alloy, where the composition includes about 30 wt% to about 99.99 -5- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 wt% 3-amino-2-butanol, and about 0.01 wt% to about 70 wt% water. In any embodiments, the compositions may include 3-amino-2-butanol in an amount of about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, about 95 wt%, about 96 wt%, about 97 wt%, about 98 wt%, about 99 wt%, about 99.5 wt%, about 99.9 wt%, about 99.95 wt%, about 99.99 wt%, or any range including and / or in-between any two of these values. For example, the composition may include 85 wt% to 95 wt% 3-amino-2- butanol. In any embodiments, the compositions may include at least about 90 wt% 3-amino- 2-butanol.

[0022] In any embodiments, the compositions may include 0.01 wt% to about 70 wt% water. Such compositions may be solutions at room temperature, e.g., a homogenous solution. In any embodiments, the compositions may include about 0.01 wt%, about 0.05 wt%, about 0.1 wt%, about 0.5 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, about 10 wt%, about 11 wt%, about 12 wt%, about 13 wt%, about 14 wt%, about 15 wt%, about 16 wt%, about 17 wt%, about 18 wt%, about 19 wt%, about 20 wt%, about 21 wt%, about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt% water, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, or any range including and / or in-between any two of these values. Thus in any embodiment herein, the compositions may include 5 wt% to 15 wt% water or about 10 wt% water. The water may be deionized, distilled or reverse osmosis (R.O.) water, or any combination thereof, including, e.g., double distilled. In any embodiment herein, the purity and water content may be adjusted depending on the desired physical properties and end-use application.

[0023] In any embodiment herein, water and / or an amino alcohol other than 3-amino-2- butanol (an “other amino alcohol”) may be included in the compositions including 3-amino- 2-butanol, e.g., to improve handling and / or modify performance characteristics. For example, addition of water to the compositions including 3-amino-2-butanol may increase the flash point, reduce the freezing point, and / or reduce the viscosity of the composition. Exemplary other amino alcohols that may be included in compositions of any embodiment herein include, but are not limited to, 3-amino-3-methyl-2-butanol, 2-aminoethanol, -6- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2- amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2- ol, or a combination of any two or more thereof. The composition of any embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2- amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2- ol, or a combination of any two or more thereof) in an amount of at least about 0.01 wt%, at least about 0.02 wt%, at least about 0.03 wt%, at least about 0.04 wt%, at least about 0.05 wt%, at least about 0.06 wt%, at least about 0.07 wt%, at least about 0.08 wt%, at least about 0.09 wt%, at least about 0.1 wt%, at least about 0.25 wt%, at least about 0.5 wt%, at least about 0.75 wt%, at least about 1 wt%, at least about 1.5 wt%, at least about 2 wt%, at least about 2.5 wt%, at least about 3 wt%, at least about 3.5 wt%, at least about 4 wt%, at least about 4.5 wt%, at least about 5 wt%, about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, or any range including and / or in-between any two of these values. The composition of any embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2- propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3- propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof) in an amount of not more than about 0.01 wt%, not more than about 0.02 wt%, not more than about 0.03 wt%, not more than about 0.04 wt%, not more than about 0.05 wt%, not more than about 0.06 wt%, not more than about 0.07 wt%, not more than about 0.08 wt%, not more than about 0.09 wt%, not more than about 0.1 wt%, not more than about 0.25 wt%, not more than about 0.5 wt%, not more than about 0.75 wt%, not more than about 1 wt%, not more than about 1.5 wt%, not more than about 2 wt%, not more than about 2.5 wt%, not more than about 3 wt%, not more than about 3.5 wt%, not more than about 4 wt%, not more than about 4.5 wt%, not more than about 5 wt%, or any range including and / or in-between any two of these values.

[0024] In any embodiment herein, the composition may include less than about 2 wt% secondary amine (e.g., 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, 2- (butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as 1-(2- -7- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 hydroxypropylamino)propan-2-ol), and / or dicycohexylamine). Thus, in any embodiment herein, the composition may include an amount of secondary amine that is less than about 2 wt%, less than about 1.5 wt%, less than about 1 wt%, less than about 0.5 wt% secondary amine, or any range including and / or in-between any two of these values. For example, in any embodiment herein, the composition may include less than about 0.5 wt% secondary amine.

[0025] In any embodiment herein, the composition may exhibit a biobased content of the 3- amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866- 24 of 0% to 100%. For example, such ranges of biobased content of the 3-amino-2-butanol in compositions of the present technology may be provided by using purely petroleum-based 3-amino-2-butanol (i.e., with 0% biobased content), using 3-amino-2-butanol produced in part with biobased starting materials, using combinations of purely petroleum-based 3-amino- 2-butanol and 3-amino-2-butanol produced in part or in whole with biobased starting materials, or¾for a biobased content of the 3-amino-2-butanol of 100%¾using 3-amino-2- butanol produced in whole with biobased starting materials. Thus, in any embodiment herein, the composition may exhibit a biobased content of the 3-amino-2-butanol (as determined using radiocarbon analysis in accordance with ASTM D6866-24) of 0%, at least about 1%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, about 100%, or any range including and / or in-between any two of these values. For example, the composition of any embodiment herein may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%. Metalworking Fluid Compositions Including 3-Amino-2-Butanol

[0026] In an aspect, provided herein are metalworking fluids that include 3-amino-2-butanol, water, and optionally a base oil. Metalworking fluids include such compositions useful in metal removal, metal forming, metal cleaning, and / or metal treating (e.g., cutting, grinding, -8- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, protecting, and the like). Metalworking fluids comprising 3-amino-2-butanol may be used in all categories of metalworking fluid processes, including but not limited to metal removal, cutting, grinding, boring, metal forming, drawing, stamping, rolling, and forging. Metalworking processes generate heat and friction, and the metalworking fluid compositions herein provide cooling by removing heat generated during operation and lubrication between the tool and the metal workpiece (e.g., a metal part). The present metalworking fluids may also remove debris without leaving a residue, and protect the tool and part being manufactured. 3-Amino-2-butanol may be used in each of the four types of metalworking fluids: neat oils, soluble oils, semi-synthetic, and synthetic metalworking fluid. In any embodiments, metalworking fluids are provided in a concentrated form and are diluted with water prior to use. The present technology encompasses metalworking fluid concentrates including a base oil and / or synthetic polymer. Metalworking fluids may further include emulsifiers, lubricants (boundary and extreme pressure lubricants), amine and / or one more amino alcohols other than 3-amino-2-butanol, and performance additives (corrosion inhibitors, couplers, defoamers, and biocides), diluted metalworking fluids thereof, metalworking fluid concentrates pre-diluted with water, as well as neat metalworking fluids. Typically, 1 part by weight of a metalworking fluid concentrate is diluted with between about 4 and about 100 parts of water (i.e., diluted to about 1 vol% to about 20 vol% of its original concentration). In any embodiments, the dilution may be 10 to 50 parts of water or even 15 to 30 parts of water.

[0027] In any aspect and / or embodiment herein, the metalworking fluid may further include an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a metalworking fluid composition of any embodiment herein include, but are not limited to, 3-amino-3-methyl-2-butanol, 2- aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino- 1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3- (ethylamino)-butan-2-ol, or a combination of any two or more thereof. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 3-amino-3- methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl- 1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3- -9- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof) in an amount of at least about 0.01 wt%, at least about 0.02 wt%, at least about 0.03 wt%, at least about 0.04 wt%, at least about 0.05 wt%, at least about 0.06 wt%, at least about 0.07 wt%, at least about 0.08 wt%, at least about 0.09 wt%, at least about 0.1 wt%, at least about 0.25 wt%, at least about 0.5 wt%, at least about 0.75 wt%, at least about 1 wt%, at least about 1.5 wt%, at least about 2 wt%, at least about 2.5 wt%, at least about 3 wt%, at least about 3.5 wt%, at least about 4 wt%, at least about 4.5 wt%, at least about 5 wt%, about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, or any range including and / or in-between any two of these values. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2- amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3- (ethylamino)-butan-2-ol, or a combination of any two or more thereof) in an amount of not more than about 0.01 wt%, not more than about 0.02 wt%, not more than about 0.03 wt%, not more than about 0.04 wt%, not more than about 0.05 wt%, not more than about 0.06 wt%, not more than about 0.07 wt%, not more than about 0.08 wt%, not more than about 0.09 wt%, not more than about 0.1 wt%, not more than about 0.25 wt%, not more than about 0.5 wt%, not more than about 0.75 wt%, not more than about 1 wt%, not more than about 1.5 wt%, not more than about 2 wt%, not more than about 2.5 wt%, not more than about 3 wt%, not more than about 3.5 wt%, not more than about 4 wt%, not more than about 4.5 wt%, not more than about 5 wt%, or any range including and / or in-between any two of these values.

[0028] In any embodiment herein, the metalworking fluid may include less than about 2 wt% secondary amine (e.g., 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, 2- (butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as 1-(2- hydroxypropylamino)propan-2-ol), and / or dicycohexylamine). Thus, in any embodiment herein, the composition may include an amount of secondary amine that is less than about 2 wt%, less than about 1.5 wt%, less than about 1 wt%, less than about 0.5 wt% secondary amine, or any range including and / or in-between any two of these values. For example, in any embodiment herein, the composition may include less than about 0.5 wt% secondary amine. -10- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0029] In any aspect and / or embodiment herein, and as discussed previously in the present disclosure, the metalworking fluid may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100%¾thus, in any embodiment herein, the composition may exhibit a biobased content of the 3-amino-2-butanol (as determined using radiocarbon analysis in accordance with ASTM D6866-24) of 0%, at least about 1%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, about 100%, or any range including and / or in-between any two of these values. For example, the composition of any embodiment herein may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%. Accordingly, a composition of any aspect and / or embodiment herein may include a renewable, biobased compound (i.e., 3- amino-2-butanol) that exhibits low toxicity while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NH3, NaOH).

[0030] In any aspect and / or embodiment herein, the metalworking fluid have a pH between about 7 and about 12, such as a pH between about 8 and about 10. Thus, in any aspect and / or embodiment herein, the metalworking fluid have a pH of about 7.0, about 7.5, about 8.0, about 8.5, about 9.0, about 9.5, about 10.0, about 10.5, about 11.0, about 11.5, about 12.0, or any range including and / or in-between any two of these values. 3-AB in Metalworking Fluids

[0031] The concentration of 3-amino-2-butanol in a metalworking fluid concentrate (i.e., prior to dilution) may be at least about 1% by weight. In some embodiments, the concentration of 3-amino-2-butanol is about 1 wt% to about 20 wt%, e.g., any of about 1, 2, 3, 4, 5, 6, 7, 8, 910, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 wt%, or a range between and including any two of the foregoing values. For example, in some embodiments, the concentration is in the range of about 2 to about 12 wt%, or about 3 to about 8 wt%. In the -11- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 final diluted metalworking fluid, the use range of neat 3-amino-2-butanol may be between about 0.01wt% or 0.02 wt% to about 2%, e.g., 0.05 wt% to 1 wt%, or even about 0.1 wt% to about 0.5 wt%. Base oils

[0032] Metalworking fluids, including concentrates, may contain a base oil, which may be a hydrocarbon oil or a synthetic polymer or copolymer. Examples of synthetic and non- synthetic base oils commonly used include, for instance, mineral oils, synthetic polymers / copolymers. Specific examples of such oils include, without limitation, petroleum oil, severely hydrotreated naphthenic and paraffinic oils, synthetic hydrocarbons, polyalphaolefin, polyglycol block co-polymers, and vegetable oils. Typical amounts of oils in metalworking fluid range from about 0 wt% to about 90 wt%, for example, any of about 0, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 wt% or a range between and including any two of the foregoing values. In some embodiments, the amount of soluble oil in the metalworking fluid ranges from about 30 wt% to about 90 wt%, including any of about 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, or 90 wt% or a range between and including any two of the foregoing values. In some embodiments the amount of, e.g., severely refined petroleum oils in semisynthetic metalworking fluid ranges from about 5 wt% to about 40 wt%, including any of about 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 wt% or a range between and including any two of the foregoing values. Synthetic metalworking fluid typically have 0% base oil as lubricity is provided by synthetic lubricants, including synthetic polymers. Additives

[0033] A variety of additives may be employed in metalworking fluid to modify properties of the base oil, including emulsifying agents, lubricants, carboxylic acid salts, corrosion inhibitors, metal deactivators, coupling agents, defoamers, biocides, chelating agents, anti- mist agents, dyes or colorants, or combinations of any two or more thereof. Emulsifying Agents -12- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0034] Metalworking fluids and concentrates (e.g., soluble oil metalworking fluids or semi- synthetic metalworking fluids) may contain emulsifying agents to bridge the gap between oil and water. Notably, some emulsifying agents are also coupling agents; exemplary coupling agents are described later in this disclosure. Emulsifiers may be anionic, non-ionic, or amphoteric in nature. Suitable emulsifiers include, but are not limited to, alkanolamides, alkylaryl sulfonates, alkylaryl sulfonic acids, amine oxides, amide and amine soaps, block copolymers, carboxylated alcohols, fatty acids, ethoxylated alcohols, ethoxylated alkylphenols, ethoxylated fatty amines, ethoxylated amides, ethoxylated fatty acids, ethoxylated fatty esters and oils (e.g., ethoxylated castor oil), ethoxylated phenols (e.g., nonyl phenol ethoxylates), fatty amines and esters, glycerol esters, glycol esters, imidazolines and imidazoline derivatives, lignin and lignin derivatives, maleic or succinic anhydrides, methyl esters, monoglycerides and derivatives, naphthenic acids, olefin sulfonates, phosphate esters, polyalkylene glycols, polyethylene glycols, polyols, polymeric (polysaccharides, acrylic acid, acrylamide), propoxylated & ethoxylated fatty acids, alcohols or alkyl phenols, quaternary surfactants, sarcosine derivatives, soaps, sorbitan derivatives, sucrose and glucose esters and derivatives, sulfates and sulfonates of oils and fatty acids (e.g., sodium petroleum sulfonates), sulfates and sulfonates ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, sulfates of fatty esters, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalene and alkyl naphthalene, sulfonates of petroleum, sulfosuccinamates, sulfosuccinates and derivatives, and tridecyl and dodecyl benzene sulfonic acids. The emulsifiers may be used at 25 wt% or less based on the total weight of the metalworking fluid, e.g., about 0.1 wt% to about 25 wt%. Suitable amounts thus include any of about 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 1516, 17, 18, 19, 20, 21, 22, 23, 24 or 25 wt% or a range between and including any two of the forgoing values. In any embodiments, the emulsifier may be present at about 0.1 wt% to about 20 wt%, or about 1 wt% to about 15 wt%. Lubricants (Boundary and Extreme Pressure)

[0035] The two main types of lubrication in metalworking fluid processes are boundary and extreme pressure (EP). Boundary lubrication involves separating the moving surfaces by the additive absorbing or adsorbing to the surface to form a film of fluid lubricant to reduce -13- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 friction and heat. Boundary lubricants include fats, vegetable oils, esters, fatty esters, complex esters, polyol esters, fatty acids, tall oil fatty acids (TOFA), fatty acid and amino alcohol salts (e.g., oleic acid 3-amino-2-butanol salt, other amino alcohol salt) block polymers, and polyglycols. EP lubricants chemisorb to the surface to form a chemical layer that minimizes the wear experienced when surfaces rub together. Extreme pressure lubricants include phosphate esters (e.g., zinc dialkyl dithiophosphate), chlorinated paraffins, chlorinated fatty acids, sulfurized fats, sulfurized fatty acids, sulfurized olefins, and overbased calcium sulfonates.

[0036] Polymeric lubricant additives can provide both types of lubrication and may be used in synthetic and semi-synthetic metalworking fluids. These can be comprised of one or more of the following: block copolymers consisting of a central polyoxypropylene block with a polyoxyethylene chain at either end, block copolymers consisting of a central polyoxyethylene block with a polyoxypropylene chain at either end, tetrablock copolymers derived from the sequential addition of ethylene oxide and propylene oxide to ethylenediamine, ethylene oxide / propylene oxide copolymers having at least one terminal hydroxyl group, water-soluble lubricant base stocks of random copolymers of ethylene oxide and propylene oxide, a water-soluble polyoxyethylene or polyoxypropylene alcohol or a water-soluble carboxylic acid ester of such alcohol, alcohol-started base stocks of all polyoxypropylene groups with one terminal hydroxyl group, monobasic and dibasic acid esters, polyol esters, polyalkylene glycol esters, polyalkylene glycols grafted with organic acids, phosphate esters, polyisobutylenes, polyacrylonitriles, polyacrylamides, polyvinylpyrrolidones, polyvinyl alcohols and copolymers of acrylic acid or methacrylic acid and an acrylic ester.

[0037] Metalworking fluids according to the present technology may include one or more boundary lubricants in an amount of 0 wt% to about 40wt%, more preferably about 1 to 25%, and most preferably about 2 to 15%. Desirably, metalworking fluids according to the present invention may include one or more boundary lubricants in an amount of at least 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14% based on the total weight of the metalworking fluid and up to about 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40% based on the total weight of the metalworking fluid. Metalworking fluids -14- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 according to the present invention may include one or more extreme pressure lubricants in an amount of 0 to about 40% based on the total weight of the metalworking fluid, more preferably about 5 to about 25% or less, and most preferably about 1 to about 5%. Desirably, metalworking fluids according to the present invention may include one or more extreme pressure lubricants in an amount of at least 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10% based on the total weight of the metalworking fluid and up to about 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40% based on the total weight of the metalworking fluid. Carboxylic Acid Salts with Amino Alcohols, Amides and Esters

[0038] Partially neutralized carboxylic acids salts of 3-amino-2-butanol (and, optionally in addition, or one or more other amino alcohols) provide a lipophilic moiety for the polymeric lubricity agents to network with and provide for the engineering of a larger droplet size. The pH of the partial neutralization is dependent upon the alkaline agent used. Many of these carboxylic acid salts additionally provide their own boundary lubrication as well. The carboxylic acids can be linear or branched, saturated or unsaturated, fatty or oil, animal or vegetable, cis or trans configured, dicarboxylic, tricarboxylic, esterified, amines, amides, or ethoxylated. Examples of carboxylic acids that may be used include: caproic / hexanoic acid, enanthic / heptanoic acid, caprylic / octanoic acid, pelargonic / nonanoic acid, isononanoic acid, capric / decanoic acid, neodecanoic acid, lauric / dodecanoic acid, stearic / octadecanoic acid, arachidic / eicosanoic acid, palmitic / hexadecanoic acid, erucic acid, oleic acid, arachidonic acid, linoleic acid, linolenic acid, myristic / tetradecanoic acid, behenic / docosanoic acid, alpha- linolenic acid, docosahexaenoic acid, ricinoleic acid, butyric acid, lard oil, tallow oil, butter, coconut oil, palm oil, cottonseed oil, wheat germ oil, soya oil, olive oil, corn oil, sunflower oil and rapeseed / canola oil.

[0039] In metalworking fluids of the present technology, carboxylic acid salts of 3-amino-2- butanol (and, optionally in addition, of one or more other amino alcohols) may be present in an amount from about 1 wt% to about 20 wt%, including any of about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 wt% or a range between and including any two of the foregoing. -15- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 Performance Additives

[0040] A variety of performance additives may be used in metalworking fluids and concentrates, including but not limited to corrosion inhibitors, metal deactivators, cobalt leaching inhibitors, coupling agents, defoamers, biocides, chelating agents, anti-mist agents, dyes or colorants, or combinations of any two or more thereof.

[0041] Corrosion inhibitors act as rust inhibitors and metal passivators by preventing oxygen and acids from getting to the metal and corroding the surface. Examples of corrosion inhibitors include medium-high molecular weight sodium petroleum sulfonates, 1,2,4- thiadiazole, alkanolamides, and amino alcohol salts (3-amino-2-butanol salts and, optionally in addition, one or more other amino alcohol salts) of various organic and inorganic acids including TOFA, mixed diacids, nonanoic, neodecanoic, sebacic, oleic, boric acids and many others known to those of skill in the art. Corrosion inhibitors may be present in metalworking fluids of the present technology in an amount ranging from about 0.05 wt% to about 10 wt%. Suitable amounts include any of about 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 6, 7, 8, 9, or 10 wt% or a range between and including any two of the foregoing values. In any embodiments the corrosion inhibitors may be present in an amount of about 0.1 wt% to about 2 wt% or even 1 wt%.

[0042] Metal deactivators and cobalt leaching inhibitors may be included to control copper corrosion of machinery’s electrical contacts and / or prevent corrosion of brass and bronze alloys. Cobalt leaching inhibitors protect the integrity of sintered carbide tooling. “Carbide” tooling includes tooling where powder metal iron carbide has been pressed and sintered together with a cobalt binder.

[0043] Coupling agents are often used to improve the stability of the emulsion by being soluble in both the oil and water phase including glycols (e.g., propylene glycol and hexylene glycol) glycol ethers (e.g., propylene glycol n-butylether), higher alcohols (e.g., hexanol), fatty alcohol (e.g., tridecyl alcohols), and fatty acids (caprylic acid, isononanoic acid, and neodecanoic acid).. Coupling agents may be present in metalworking fluids of the present technology in an amount ranging from about 0.05 wt% to about 10 wt%. Suitable amounts include any of about 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, -16- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 5, 6, 7, 8, 9, or 10 wt% or a range between and including any two of the foregoing values. In any embodiments the coupling agents are present in an amount of about 0.1 wt% to about 2 wt% or even 1 wt%.

[0044] Defoamers affect surface tension. They are dispersed and not fully soluble in the metalworking fluid concentrate or the metalworking fluid composition and lie on the surface in use. Defoamers include silicones, reacted silicones, organo modified siloxanes, polyalkylenimines, and waxes. Exemplary defoamers include polyethyleneimine, alkyl polysiloxane such as dimethyl polysiloxane, diethyl polysiloxane, dipropyl polysiloxane, methyl ethyl polysiloxane, dioctyl polysiloxane, diethyl polysiloxane, methyl propyl polysiloxane, dibutyl polysiloxane and didodecyl polysiloxane; organo-phosphorus compound such as n-tri-butyl phosphate, n-tributoxy ethyl phosphate or triphenylphosphite, or a mixture therefore; and copolymers of poly alkylene oxide (ethylene oxide, propylene oxide and butylene oxide). Defoamers may be present in metalworking fluids at about 0.01 wt% to about 2 wt%. Suitable amounts thus include any of about 0.01, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.25, 1.5, 1.75, or 2 wt% or a range between and including any two of the foregoing values.

[0045] Biocides are used for microbial control in metalworking fluids. Biocides that may be used in metalworking fluids¾and may be used in a metalworking fluid of the present technology¾for microbial control (e.g., bacteria and / or fungi) include but not limited to triazines, isothiazolones, dinitromorpholines, parachlorometacresol, phenolics, bromonitropropanes, butyl carbamates, or a combination of any two or more thereof. Exemplary active concentration ranges for the biocide in metalworking fluids and concentrates varies depending on the biocide being used, but can be readily determined by a person of ordinary skill in the art. By way of example, in any embodiment herein of the present technology including a biocide, the concentration may be at least about 0.01 wt% and / or may be no more than about 5 wt%. Suitable concentrations include any of about 0.01, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, or 5 wt% or a range between and including any two of the foregoing values. In any embodiments, the biocide may be present at about 0.01 wt% to about 3 wt% or about 4 wt%. -17- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0046] By way of example for specific biocides, 1,3,5-tris(2-hydroxyethyl)-s-triazine is commonly used in the active range of 0.76 to 3% by weight, especially, 1.1 to 3%, iodopropynylbutylcarbamate is used in the range of 0.2 to 0.6%, e.g., 0.3 to 0.6%, 1,2- benzisothiazolinone is used in the range of 0.08 to 0.36%, e.g., 0.16 to 0.36%, 4,4- dimethyloxazolidine is used in the range of 0.78 to 3.1% e.g., at 1.2 to 3.1%, 7-ethyl bicycooxazolidine is used in the range 1 to 4%, especially 1.5 to 4%, a combination of 4-(2- nitrobutyl)-morpholine with 4,4′-(2-ethyl-2-nitrotrimethylene)dimorpholine is used in the range of 1 to 4%, e.g., at 1.5 to 3%, and a combination of 5-chloro-2-methyl-4-isothiazolin-3- one with 2-methyl-4-isothiazolin-3-one is used in the range of 0.01% to 0.08%, e.g., 0.05% to 0.08%. Amines and Amino Alcohols Other than 3-AB

[0047] Amines and amino alcohols are widely used to neutralize critical acid-functional ingredients (emulsifiers, lubricity additives corrosion inhibitors, etc.), and to develop and maintain alkaline pH >7 and to provide buffering capacity. This ensures the higher pH which helps to increase bioresistance of metalworking fluid concentrates and dilutions, and to protect tools and parts from corrosion. Amino alcohol choice can significantly influence performance, including but not limited to providing pH stability, and forming amino alcohol salts improving emulsifier efficiency (anionic emulsifier salts), boundary and EP lubrication (acidic lubricant salts).

[0048] Alkalinity, pH, and bacteria affect the corrosion characteristics of a lubricant, and therefore products are formulated to maintain these attributes accordingly. A drop in pH is a good indicator that bacteria is present and rust is likely going to occur. Corrosion control (e.g., diacid salts) of ferrous alloys, reducing corrosion and staining of aluminum alloys (e.g., acidic phosphate ester salts), improving tool life (low metal leaching, e.g., cobalt from carbide tools) and synergy with biocide providing fluid longevity (microbial resistance). Amino alcohols most often used are primary and tertiary. Ideally metalworking fluids should be secondary amine free (e.g., diethanolamine (DEA free).

[0049] Thus, as disclosed previously herein, in any aspect and / or embodiment herein the metalworking fluid composition may further include an amino alcohol other than 3-amino-2- -18- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 butanol (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a metalworking fluid composition of any embodiment herein include, but are not limited to, 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2- propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3- propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2- aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino- 1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3- (ethylamino)-butan-2-ol, or a combination of any two or more thereof) in an amount of at least about 0.01 wt%, at least about 0.02 wt%, at least about 0.03 wt%, at least about 0.04 wt%, at least about 0.05 wt%, at least about 0.06 wt%, at least about 0.07 wt%, at least about 0.08 wt%, at least about 0.09 wt%, at least about 0.1 wt%, at least about 0.25 wt%, at least about 0.5 wt%, at least about 0.75 wt%, at least about 1 wt%, at least about 1.5 wt%, at least about 2 wt%, at least about 2.5 wt%, at least about 3 wt%, at least about 3.5 wt%, at least about 4 wt%, at least about 4.5 wt%, at least about 5 wt%, about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, or any range including and / or in-between any two of these values. The composition of any aspect and / or embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2- amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2- ol, or a combination of any two or more thereof) in an amount of not more than about 0.01 wt%, not more than about 0.02 wt%, not more than about 0.03 wt%, not more than about 0.04 wt%, not more than about 0.05 wt%, not more than about 0.06 wt%, not more than about 0.07 wt%, not more than about 0.08 wt%, not more than about 0.09 wt%, not more than about 0.1 wt%, not more than about 0.25 wt%, not more than about 0.5 wt%, not more than about 0.75 wt%, not more than about 1 wt%, not more than about 1.5 wt%, not more than about 2 wt%, not more than about 2.5 wt%, not more than about 3 wt%, not more than about 3.5 wt%, not more than about 4 wt%, not more than about 4.5 wt%, not more than about 5 wt%, or any range including and / or in-between any two of these values. -19- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0050] The examples herein are provided to illustrate advantages of the present technology and to further assist a person of ordinary skill in the art with preparing or using the compositions of the present technology. The examples herein are also presented in order to more fully illustrate the present technology. The examples should in no way be construed as limiting the scope of the present technology, as defined by the appended claims. The examples can include or incorporate any of the variations, aspects or aspects of the present technology described above. The variations, aspects or aspects described above may also further each include or incorporate the variations of any or all other variations, aspects or aspects of the present technology. EXAMPLES General Information

[0051] The IUPAC names and abbreviations of the compounds tested herein are provided below. Example 1. Synthesis of Renewable Biobased 3-Amino-2-Butanol Synthesis of 3-amino-2-butanol (3-AB). -20- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0052] Nitroethane (1 mol, 97%,) and bio-acetaldehyde (1 mol, 99%, MilliporeSigma) were added to triethylamine (0.02 mol, MilliporeSigma) in methanol while maintaining the temperature below 50 °C. The mixture was stirred at 50 °C for 2 h, then stirred at ambient temperature overnight. GC-FID analysis indicated 95% conversion of NE to 3-NB.

[0053] The reaction mixture was then fed into a stainless-steel reactor containing Raney Nickel (10 wt%) and methanol with 650 psi hydrogen at 45-65 °C. Upon complete reaction, the mixture was separated from the catalyst and distilled at ambient pressure. The fraction containing the desired product was collected at 159 °C and recovered as a colorless liquid. The isolated yield was 70 % and the purity was 99 % according to GC-FID analysis (capillary column: 30 m fused silica, (5%-phenyl)-methylpolysiloxane bonded-phase column with a 0.25 mm inner diameter and 1.0 μm film thickness; carrier gas flow rate: 1 mL / min helium; gas chromatograph: Agilent model 7890, Series II). Example 2. Exemplary Semi-Synthetic Metalworking Fluid Compositions with 20% Oil

[0054] Semi-synthetic metal working fluids with 20% oil and having the compositions shown in Table 1 below were prepared to have a target pH of 9.5 when diluted to a 5% use solution. Compositions A-C are comparative compositions, whereas Composition D contains 3AB in accordance with the present technology. Each composition was prepared according to the following protocol. 1. Add 1-6 (water, diacid, and one of AMP, MIPA, MEA, or 3AB) at room temperature and mix until dissolved (clear) 5-10 minutes. 2. In a separate container heat 7 (naphthenic oil), 8 (sodium sulfonate), and 9 (tall oil fatty acid) up at 100 °C for 5-10 minutes to disperse sodium sulfonate into naphthenic oil. Allow to cool or ice bath to room temperature. Then add 10-12 to 7-9 (oil phase) at room temperature. Mix for 5-10 minutes until homogeneous. 3. Add oil phase (7-12) to water phase (1-6) at room temperature. Mix for 5-10 minutes until homogeneous. -21- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 4. While mixing add 13 drop-wise at room temperature. Mix for 30 minutes – 1 hour until a stable emulsion is formed. 5. Wait 24 hours to pH at 5% dilution in distilled water. Table 1. Low Oil Semi-Synthetic Metalworking Fluid Compositions Q-S With Phosphate -22- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 Example 3. Droplet Size and Polydispersity Index (PDI) of Exemplary and Comparative Metalworking Fluids

[0055] Droplet size and polydispersity index (PDI) for exemplary and comparative metalworking fluids was assessed. The metalworking fluids were compositions A-D in Example 2, where A-C are comparative compositions and D contains 3AB in accordance with the present technology. Prior to measuring droplet size and PDI, the metalworking fluid compositions were diluted to a concentration of 5 wt.% in water. The samples were mixed for 10 minutes and then left undisturbed for 5 minutes prior to each test.

[0056] A Malvern Zetasizer Nano ZS dynamic light scattering instrument was used to measure droplet size and PDI, the results of which are provided in Table 2 and Table 3 below, and represented graphically in FIGS.1A and 1B. Measurements were conducted at 25°C, with at least 7 measurements per sample tested. 3AB was found to provide the smaller droplet size and lower PDI in the emulsion, offering significant advantages for emulsion stability and metalworking performance. The combination of small droplet size and narrow PDI may work synergistically to increase emulsion stability, enhance fluid performance, extend fluid life, and deliver higher-quality machining results. This may make the fluid more reliable and cost-efficient in demanding applications. Table 2. Results of Droplet Size Measurements Table 3. Results of Polydispersity Index (PDI) Measurements -23- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0057] Without being bound by any theory, the smaller droplet size may improve emulsion stability by minimizing coalescence and phase separation. With a higher surface area relative to their volume, smaller droplets may allow emulsifiers to stabilize the oil-water interface, reducing the risk of droplet merging and maintaining emulsion integrity more effectively over time. Additionally, the finer droplet size may promote more uniform distribution of additives, further enhancing fluid performance.

[0058] Without being bound by any theory, the lower PDI may improve stability by minimizing variations in droplet size, making the emulsion less prone to instability. This may reduce the risk of phase separation, providing homogeneity and good performance over extended periods. A lower PDI may also ensure that performance additives are evenly distributed throughout the fluid, increasing their effectiveness, enhancing fluid performance, and reducing the need for frequent adjustments. 3AB's PDI of <0.1 indicates excellent control over the emulsion’s structure, contributing to superior stability, performance, and reliability in metalworking operations. Example4. pH Buffering of Lactic Acid of Exemplary and Comparative Metalworking Fluids

[0059] The effectiveness of 3AB in buffering against acidification was assessed in comparison to AMP, MIPA, and MEA. In this experiment, a 40 mL volume of aqueous solution of 0.1 M amine¾either 3AB, AMP, MIPA, or MEA¾was prepared and stirred gently while measuring pH. The buffering capacity was assessed by titrating, using an autotitrator, measured volumes of 0.1 M aqueous lactic acid solution to the aqueous solution while measuring pH. The pH was recorded after each addition of lactic acid solution. The results of these experiments are illustrated in FIG.2. It was found that 3AB provided significantly better buffering against acidification as compared to MIPA or MEA, and comparable buffering as compared to AMP, at least up through 40 mL addition of 0.1 M lactic acid solution. -24- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781

[0060] 3AB maintained the metalworking buffering zone of pH 8–9.5 in the presence of lactic acid for longer than comparable amino alcohols MIPA and MEA. MIPA and MEA exhibited pH levels approximately 1 unit lower than 3AB under the same lactic acid conditions. Enhanced buffering performance is useful for maintaining fluid integrity, extending fluid life, protecting machinery, reducing part corrosion, and ensuring safe working conditions. Lactic acid acts as a surrogate for acids produced during microbial degradation of metalworking fluids. Sustained buffering in the presence of lactic acid is particularly crucial to prevent excessive acidification, which can lead to premature fluid failure and significant disruptions in metalworking processes. Example 5. Cobalt Leaching of Exemplary and Comparative Metalworking Fluids

[0061] The effectiveness of 3AB in minimizing and / or reducing cobalt leaching from metalworking tools containing cobalt (such as those comprising tungsten carbide particles bonded with cobalt) as compared to AMP, monoisopropanolamine (“MIPA”), and monoethanolamine (“MEA”) was assessed in cobalt leaching tests. In particular, a 1% aqueous solution of 3AB, AMP, MIPA, or MEA, and 1500 ppm of fine cobalt powder were added to each test sample. The pH of each sample was adjusted to approximately 9.5 using acetic acid. The samples were then stirred for 24 hours, filtered, and analyzed using Inductively Coupled Plasma (ICP) emission spectroscopy to measure the amount of cobalt leached (in ppm), the results of which are summarized in Table 4 below and illustrated in FIG.3. As shown in Table 4 and FIG.3, 3AB was found to provide significantly superior cobalt leaching control as compared to MIPA and MEA, and comparable cobalt leaching control as compared to AMP. Table 4. Results of Cobalt Leaching Tests -25- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 Example 6. Aluminum Staining of Exemplary and Comparative Metalworking Fluids

[0062] The effectiveness of 3AB in inhibiting or reducing aluminum staining was assessed in comparison to AMP, MIPA, and MEA. In this experiment, coupons of aluminum alloy (356, 2024, 6061, 7075) were sanded on both sides and then partially submerged in 35 mL of 5 wt.% metal working fluid in water containing about 200 ppm total dissolved solids (TDS). The coupons were allowed to age in the metal working fluid solution for 24 hours at about 40°C. Results are illustrated in FIG.4. As shown in FIG.4, 3AB provided comparable or better aluminum staining inhibition than AMP, MIPA, and MEA, across all alloy types.

[0063] The improved inhibition of aluminum staining by 3AB may provide finished parts with better quality, appearance, and longevity. Aluminum’s lightweight and high- performance properties make it a useful material in aerospace, automotive, and general industries, where reducing weight helps lower emissions. For these applications, maintaining low stain and corrosion levels is useful, and formulations containing 3AB achieved these properties. EQUIVALENTS

[0064] While certain embodiments have been illustrated and described, a person with ordinary skill in the art, after reading the foregoing specification, can effect changes, substitutions of equivalents and other types of alterations to the compositions of the present technology as set forth herein. Each aspect and embodiment described above can also have included or incorporated therewith such variations or aspects as disclosed regarding any or all of the other aspects and embodiments.

[0065] The present technology is also not to be limited in terms of the particular aspects described herein, which are intended as single illustrations of individual aspects of the present technology. Many modifications and variations of this present technology can be made without departing from its spirit and scope, as will be apparent to those skilled in the art. Functionally equivalent methods within the scope of the present technology, in addition to those enumerated herein, will be apparent to those skilled in the art from the foregoing descriptions. Such modifications and variations are intended to fall within the scope of the appended claims. It is to be understood that this present technology is not limited to -26- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 particular methods, reagents, compounds, or compositions, which can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only, and is not intended to be limiting. Thus, it is intended that the specification be considered as exemplary only with the breadth, scope and spirit of the present technology indicated only by the appended claims, definitions therein and any equivalents thereof.

[0066] The embodiments, illustratively described herein may suitably be practiced in the absence of any element or elements, limitation or limitations, not specifically disclosed herein. Thus, for example, the terms “comprising,” “including,” “containing,” etc. shall be read expansively and without limitation. Additionally, the terms and expressions employed herein have been used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the claimed technology. Additionally, the phrase “consisting essentially of” will be understood to include those elements specifically recited and those additional elements that do not materially affect the basic and novel characteristics of the claimed technology. The phrase “consisting of” excludes any element not specified.

[0067] In addition, where features or aspects of the disclosure are described in terms of Markush groups, those skilled in the art will recognize that the disclosure is also thereby described in terms of any individual member or subgroup of members of the Markush group. Each of the narrower species and subgeneric groupings falling within the generic disclosure also form part of the technology. This includes the generic description of the technology with a proviso or negative limitation removing any subject matter from the genus, regardless of whether or not the excised material is specifically recited herein.

[0068] As will be understood by one skilled in the art, for any and all purposes, particularly in terms of providing a written description, all ranges disclosed herein also encompass any and all possible subranges and combinations of subranges thereof. Any listed range can be easily recognized as sufficiently describing and enabling the same range being broken down into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each range discussed herein can be readily broken down into a lower third, middle third and upper -27- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 third, etc. As will also be understood by one skilled in the art all language such as “up to,” “at least,” “greater than,” “less than,” and the like, include the number recited and refer to ranges which can be subsequently broken down into subranges as discussed above. Finally, as will be understood by one skilled in the art, a range includes each individual member.

[0069] All publications, patent applications, issued patents, and other documents (for example, journals, articles and / or textbooks) referred to in this specification are herein incorporated by reference as if each individual publication, patent application, issued patent, or other document was specifically and individually indicated to be incorporated by reference in its entirety. Definitions that are contained in text incorporated by reference are excluded to the extent that they contradict definitions in this disclosure.

[0070] The present technology may include, but is not limited to, the features and combinations of features recited in the following lettered paragraphs, it being understood that the following paragraphs should not be interpreted as limiting the scope of the claims as appended hereto or mandating that all such features must necessarily be included in such claims: A. A metalworking fluid comprising 3-amino-2-butanol; about 0.1 wt% or greater water; and optionally a base oil. B. The metalworking fluid of Paragraph A, wherein the metalworking fluid comprises about 0.01 wt% to about 20 wt% 3-amino-2-butanol, optionally wherein the metalworking fluid comprises about 10 wt% to about 50 wt% base oil. C. The metalworking fluid of Paragraph A or Paragraph B, wherein the metalworking fluid comprises about 0.01 wt% to about 10 wt% 3-amino-2-butanol. D. The metalworking fluid of any one of Paragraphs A-C, wherein the metalworking fluid is a soluble oil, a semi-synthetic, or a synthetic. -28- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 E. The metalworking fluid of any one of Paragraphs A-D, wherein the base oil comprises a petroleum oil, a hydrotreated naphthenic oil, a hydrotreated paraffinic oils, a synthetic hydrocarbon, a polyalphaolefin, a polyglycol block co-polymer, a vegetable oil, a hydrotreated vegetable oil, a complex ester, a polyol ester, a re-refined base oil, or a combination of any two or more thereof. F. The metalworking fluid of any one of Paragraphs A-E, wherein the metalworking fluid further comprises an emulsifier, a corrosion inhibitor, a biocide, a neutralizing agent, or a combination of any two or more thereof. G. The metalworking fluid of Paragraph F, wherein the metalworking fluid comprises a nonionic emulsifier. H. The metalworking fluid of Paragraph G, wherein the nonionic emulsifier comprises an ethoxylated alcohol, an alkanolamide, an ester, or a combination of any two or more thereof. I. The metalworking fluid of any one of Paragraphs F-H, wherein the metalworking fluid comprises an anionic emulsifier. J. The metalworking fluid of Paragraph I, wherein the anionic emulsifier comprises a sodium sulfonate, fatty acid salt, a succinic acid salt, a succinic anhydride salt, a polymeric emulsifier, or a combination of any two or more thereof. K. The metalworking fluid of Paragraph J, wherein the polymeric emulsifier comprises a polyethylene glycol. L. The metalworking fluid of any one of Paragraphs F-K, wherein the metalworking fluid comprises the corrosion inhibitor, the corrosion inhibitor comprising one or more of a phosphate ester, a sodium sulfonate, a thiadiazole, an alkanolamide, an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”), a 3-amino-2-butanol salt, an other amino alcohol salt, a tall oil fatty acid (TOFA), a diacid, or a combination of any two or more thereof. -29- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 M. The metalworking fluid of any one of Paragraphs F-L, wherein the metalworking fluid comprises the biocide, the biocide comprising a mixture of biocidal compounds, said mixture exhibiting an antibacterial and an antifungal effect. N. The metalworking fluid of any one of Paragraphs A-M, wherein the metalworking fluid is a concentrate to be diluted to about 1 vol% to about 20 vol% of its original concentration with water. O. The metalworking fluid of any one of Paragraphs A-N, further comprising one or more additives selected from the group consisting of colorants; viscosity-altering agents; lubricants, buffers, anti-oxidants, coupling agents, defoamers, anti-misting agents, or a combination of any two or more thereof. P. The metalworking fluid of any one of Paragraphs A-O, further comprising a neutralizing agent. Q. The metalworking fluid of Paragraph P, wherein the neutralizing agent comprises one or more of a metal hydroxide, an alkyl amine, or an other amino alcohol. R. The metalworking fluid of Paragraph P or Paragraph Q, wherein the neutralizing agent comprises one or more of monoisopropanolamine (MIPA), diglycolamine (DGA), MEA (monoethanolamine), TEA (triethanolamine), 2-amino-2-methyl-1-propanol (AMP), 2-amino-1-butanol (2AB), 2-amino-2-ethyl-1,3-propanediol (AEPD), methyldiethanolamine (MDEA), tris(hydroxymethyl)aminomethane (TRIS), dicyclohexylamine (DCHA), 3-amino-4-octanol (3A4O), 3-amino-3-methyl-2- butanol, or a combination of any two or more thereof. S. The metalworking fluid of any one of Paragraphs L-R, wherein the other amino alcohol comprises one or more of 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, 2-amino-1- butanol, 2-amino-2-ethyl-1,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3- (ethylamino)-butan-2-ol, or a combination of any two or more thereof. -30- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 T. The metalworking fluid of any one of Paragraphs L-S, wherein the metalworking fluid comprises at least about 0.01 wt% of the other amino alcohol. U. The metalworking fluid of any one of Paragraphs A-T, wherein the metalworking fluid comprises less than 2 wt% secondary amine. V. The metalworking fluid of any one of Paragraphs A-U, wherein the 3-amino-2-butanol has a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24. W. The metalworking fluid of any one of Paragraphs A-V, wherein the metalworking fluid has a pH between about 7 and about 12, optionally wherein the metalworking fluid has a pH between about 8 and about 10. X. The metalworking fluid of any one of Paragraphs A-W, wherein the metalworking fluid inhibits staining of nonferrous metal workpiece which the fluid contacts during metalworking operation. Y. The metalworking fluid of any one of Paragraphs A-X, wherein the metalworking fluid inhibits cobalt leaching of cobalt containing metal workpiece and / or carbide toll which the fluid contacts during metalworking operation. Z. The metalworking fluid of any one of Paragraphs A-Y, wherein the metalworking fluid inhibits cools and / or lubricates during metalworking operations. AA. A method comprising adding to a composition an effective amount of 3-amino-2- butanol to raise the pH of the composition, stabilize the composition, and / or at least partially neutralize an acidic compound in the composition, the composition comprising an aqueous dispersion comprising a base oil and / or an emulsifier. AB. A composition for use in metalworking fluids and metalworking applications, the composition comprising about 30 wt% to about 99.99 wt% 3-amino-2-butanol; and about 0.01 wt% to about 70 wt% water. -31- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 AC. The composition for use of Paragraph AB, wherein the composition further comprises an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”). AD. The composition for use of Paragraph AB or Paragraph AC, wherein the composition is for use in metal removal, metal forming, metal cleaning, and / or metal treating, optionally wherein the composition is for use in cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and / or protecting (i) one or more metals, and / or (ii) one or more metal alloys. AE. The composition for use of Paragraph AC or Paragraph AD, the composition comprising about 0.01 wt% to about 60 wt% of the other amino alcohol. AF. The composition for use of any one of Paragraphs AC-AE, comprising not more than 1 wt% of the other amino alcohol. AG. The composition for use of any one of Paragraphs AB-AF, comprising about 70 wt% to about 95 wt% 3-amino-2-butanol and about 5 wt% to about 30 wt% water. AH. The composition for use of any one of Paragraphs AC-AG, comprising about 90 wt% 3- amino-2-butanol, about 10 wt% water, and less than 1 wt% of the other amino alcohol. AI. The composition for use of any one of Paragraphs AB-AH, wherein the composition comprises less than 2 wt% secondary amine. AJ. The composition for use of any one of Paragraphs AC-AI, wherein the composition further comprises not more than 5 wt% of the other amino alcohol. AK. The composition for use of any one of Paragraphs AC-AJ, wherein the other amino alcohol is 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2- propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3- propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof. -32- 4935-4281-6551 v.4 Atty. Dkt. No.: 109691-0781 AL. The composition for use of any one of Paragraphs AC-AK, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol. AM. The composition for use of any one of Paragraphs AC-AL, wherein the composition comprises 3-(ethylamino)-butan-2-ol in addition to 3-amino-2-butanol. AN. The composition for use of any one of Paragraphs AB-AM, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

[0071] Other embodiments are set forth in the following claims, along with the full scope of equivalents to which such claims are entitled. -33- 4935-4281-6551 v.4

Claims

Atty. Dkt. No.: 109691-0781 WHAT IS CLAIMED IS:

1. A metalworking fluid comprising 3-amino-2-butanol; and about 0.1 wt% or greater water.

2. The metalworking fluid of Claim 1, wherein the metalworking fluid further comprises a base oil.

3. The metalworking fluid of Claim 2, wherein the metalworking fluid comprises about 10 wt% to about 50 wt% base oil.

4. The metalworking fluid of Claim 1, wherein the metalworking fluid comprises about 0.01 wt% to about 20 wt% 3-amino-2-butanol.

5. The metalworking fluid of Claim 1, wherein the metalworking fluid comprises about 0.01 wt% to about 10 wt% 3-amino-2-butanol.

6. The metalworking fluid of Claim 1, wherein the metalworking fluid is a soluble oil, a semi-synthetic, or a synthetic.

7. The metalworking fluid of Claim 1, wherein the base oil comprises a petroleum oil, a hydrotreated naphthenic oil, a hydrotreated paraffinic oils, a synthetic hydrocarbon, a polyalphaolefin, a polyglycol block co-polymer, a vegetable oil, a hydrotreated vegetable oil, a complex ester, a polyol ester, a re-refined base oil, or a combination of any two or more thereof.

8. The metalworking fluid of Claim 1, wherein the metalworking fluid further comprises an emulsifier, a corrosion inhibitor, a biocide, a neutralizing agent, or a combination of any two or more thereof.

9. The metalworking fluid of Claim 8, wherein the metalworking fluid comprises a nonionic emulsifier. -34- 4935-4281-6551 v.4Atty. Dkt. No.: 109691-0781 10. The metalworking fluid of Claim 9, wherein the nonionic emulsifier comprises an ethoxylated alcohol, an alkanolamide, an ester, or a combination of any two or more thereof.

11. The metalworking fluid of any Claim 8, wherein the metalworking fluid comprises an anionic emulsifier.

12. The metalworking fluid of Claim 11, wherein the anionic emulsifier comprises a sodium sulfonate, fatty acid salt, a succinic acid salt, a succinic anhydride salt, a polymeric emulsifier, or a combination of any two or more thereof.

13. The metalworking fluid of Claim 12, wherein the polymeric emulsifier comprises a polyethylene glycol.

14. The metalworking fluid of Claim 8, wherein the metalworking fluid comprises the corrosion inhibitor, the corrosion inhibitor comprising one or more of a phosphate ester, a sodium sulfonate, a thiadiazole, an alkanolamide, an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”), a 3-amino-2-butanol salt, an other amino alcohol salt, a tall oil fatty acid (TOFA), a diacid, or a combination of any two or more thereof.

15. The metalworking fluid of Claim 8, wherein the metalworking fluid comprises the biocide, the biocide comprising a mixture of biocidal compounds, said mixture exhibiting an antibacterial and an antifungal effect.

16. The metalworking fluid of Claim 1, wherein the metalworking fluid is a concentrate to be diluted to about 1 vol% to about 20 vol% of its original concentration with water.

17. The metalworking fluid of Claim 1, further comprising one or more additives selected from the group consisting of colorants; viscosity-altering agents; lubricants, buffers, anti-oxidants, coupling agents, defoamers, anti-misting agents, or a combination of any two or more thereof.

18. The metalworking fluid of Claim 1, further comprising a neutralizing agent. -35- 4935-4281-6551 v.4Atty. Dkt. No.: 109691-0781 19. The metalworking fluid of Claim 18, wherein the neutralizing agent comprises one or more of a metal hydroxide, an alkyl amine, or an other amino alcohol.

20. The metalworking fluid of Claim 18, wherein the neutralizing agent comprises one or more of monoisopropanolamine (MIPA), diglycolamine (DGA), MEA (monoethanolamine), TEA (triethanolamine), 2-amino-2-methyl-1-propanol (AMP), 2-amino-1-butanol (2AB), 2-amino-2-ethyl-1,3-propanediol (AEPD), methyldiethanolamine (MDEA), tris(hydroxymethyl)aminomethane (TRIS), dicyclohexylamine (DCHA), 3-amino-4-octanol (3A4O), 3-amino-3-methyl-2- butanol, or a combination of any two or more thereof.

21. The metalworking fluid of Claim 14, wherein the other amino alcohol comprises one or more of 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2- propanol, 2-amino-2-methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3- propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.

22. The metalworking fluid of Claim 14, wherein the metalworking fluid comprises at least about 0.01 wt% of the other amino alcohol.

23. The metalworking fluid of Claim 1, wherein the metalworking fluid comprises less than 2 wt% secondary amine.

24. The metalworking fluid of Claim 1, wherein the 3-amino-2-butanol has a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.

25. The metalworking fluid of Claim 1, wherein the metalworking fluid has a pH between about 7 and about 12.

26. The metalworking fluid of Claim 1, wherein the metalworking fluid inhibits staining of nonferrous metal workpiece which the fluid contacts during metalworking operation. -36- 4935-4281-6551 v.4Atty. Dkt. No.: 109691-0781 27. The metalworking fluid of Claim 1, wherein the metalworking fluid inhibits cobalt leaching of cobalt containing metal workpiece and / or carbide toll which the fluid contacts during metalworking operation.

28. The metalworking fluid of Claim 1, wherein the metalworking fluid inhibits cools and / or lubricates during metalworking operations.

29. A method comprising adding to a composition an effective amount of 3-amino-2-butanol to raise the pH of the composition, stabilize the composition, and / or at least partially neutralize an acidic compound in the composition, the composition comprising an aqueous dispersion comprising a base oil and / or an emulsifier.

30. A composition for use in metalworking fluids and metalworking applications, the composition comprising about 30 wt% to about 99.99 wt% 3-amino-2-butanol; and about 0.01 wt% to about 70 wt% water.

31. The composition for use of Claim 30, wherein the composition is for use in cutting, grinding, boring, turning, milling, machining, drawing, stamping, forming, rolling, cleaning, and / or protecting a metal and / or a metal alloy.

32. The composition for use of Claim 30, wherein the composition further comprises an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”).

33. The composition for use of Claim 32, the composition comprising about 0.01 wt% to about 60 wt% of the other amino alcohol.

34. The composition for use of Claim 32, comprising not more than 1 wt% of the other amino alcohol.

35. The composition for use of Claim 30, comprising about 70 wt% to about 95 wt% 3- amino-2-butanol and about 5 wt% to about 30 wt% water.

36. The composition for use of Claim 30, comprising about 90 wt% 3-amino-2-butanol, about 10 wt% water, and less than 1 wt% of the other amino alcohol. -37- 4935-4281-6551 v.4Atty. Dkt. No.: 109691-0781 37. The composition for use of Claim 30, wherein the composition comprises less than 2 wt% secondary amine.

38. The composition for use of Claim 32, wherein the composition further comprises not more than 5 wt% of the other amino alcohol.

39. The composition for use of Claim 32, wherein the other amino alcohol is 3-amino-3- methyl-2-butanol, 2-aminoethanol, triethanolamine, 1-amino-2-propanol, 2-amino-2- methyl-1-propanol, 2-amino-1-butanol, 2-amino-2-ethyl-1,3-propanediol, 3- (ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.

40. The composition for use of Claim 39, wherein the composition comprises at least about 0.01 wt% of the other amino alcohol.

41. The composition for use of Claim 39, wherein the composition 3-(ethylamino)-butan-2- ol in addition to 3-amino-2-butanol.

42. The composition for use of Claim 30, wherein the composition exhibits a biobased content of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24. -38- 4935-4281-6551 v.4

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