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1. (WO2017098408) METHODS OF REDUCING COLOR IN ALKANOLAMINE COMPOSITIONS AND COMPOSITIONS PRODUCED THEREBY
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CLAIMS

What is claimed is:

1. A method of reducing color in an alkanolamine, the method comprising:

contacting the alkanolamine with a color-reducing amount of a borane complex effective to provide an alkanolamine composition having a Platinum-Cobalt Color Value, Test Method ASTM D1209, of less than 50, preferably less than 30, more preferably 0 to 20.

2. A color-reduced alkanolamine composition, the composition comprising:

triethanolamine and an effective color-reducing amount of a borane complex, wherein the composition has a Platinum-Cobalt Color Value, Test Method ASTM D 1209, of less than 50, preferably less than 30, more preferably 0 to less than or equal to 20.

3. The method or composition of claim 1 or 2, wherein the alkanolamine is a mono(Ci-io alkanol)amine, a di(Ci-io alkanol)amine, a tri(Ci-io alkanol)amine, an N-(Ci-io alkyl) di(C2-4 alkanol)amine, an N,N-di(Ci-io alkyl) (C2 alkanol)amine, an N-(Ci-io alkanol)pyrrolidine, N-(CMO alkanol)imidazolidine, an N-(Ci-io alkanol)piperidine, an N-(Ci-io alkanol)piperazine or a combination comprising at least one of the foregoing;

preferably monoethanolamine, diethanolamine, methyldiethanolamine,

isopropanolamine, diisopropanolamine, (2-hydroxyethyl)piperazine, or a combination comprising at least one of the foregoing.

4. The method or composition of claim 1 or 2, wherein the alkanolamine is a tri(Ci-10 alkanol)amine, preferably triethanolamine.

5. The method or composition of any one or more of claims 1 to 4, wherein:

the borane complex is of the formula

L- BRatb-a

wherein L is ammonia, hydrazine, an organic amine, a thioether, an organic phosphine, or a heterocycle, and each R is independently is a Ci-12 alkyl group, a C3-8 cycloalkyl group, a C3-7 heterocycloalkyl group, a C6-io aromatic group, or a C3-15 heteroaromatic group, optionally wherein any two R form a ring with the boron atom; and a is 0 to 2;

the borane complex is of the formula


wherein G is an ammonium ion, a quaternary ammonium ion, a tertiary sulfonium ion, or a quaternary organic phosphonium ion, c is 1 to 3, x is 1 to 2, y is 2 to 20, and z is 4 to 14; or the borane complex is of the formula

R7

I

B B

I I

R7 B R7

wherein each R7 is independently a Ci-8 alkyl or a Ci-8 alkoxy.

6. The method or composition of any one or more of claims 1 to 5, wherein:

the borane complex is of the formula

L- BH3

wherein L is ammonia or a Ci-24 organic amine, an organic phosphine substituted with three Ci-12 hydrocarbyl groups, a C3-18 heterocycle, or a C2-20 thioether; or

the borane complex is of the formula


wherein

a is 1 or 2, and

each R is independently the same or different, and is a Ci-12 alkyl group, a C3-8 cycloalkyl group, a C3-7 heterocycloalkyl group, a C6-10 aromatic group, or a C3-15 heteroaromatic group, optionally wherein two R form a ring with the boron atom, preferably wherein each R is independently a Ci-6 alkyl group, a C3-6 cycloalkyl group, or a Ce aromatic group.

7. The method or composition of claim 6, wherein L is ammonia or a Ci-24 amine of the formula

N

I

R>

wherein each R1 is the independently

hydrogen or a Ci-8 hydrocarbyl group, optionally wherein any two R1 form a ring with the nitrogen atom, and provided that not all R1 are hydrogen, or

hydrogen, a Ci-8 alkyl group, a C3-8 cycloalkyl group, a C3-7 heterocycloalkyl group, a Ce-18 aromatic group, or a C3-15 heteroaromatic group, or any two R1 together form a C2-6 ring with the nitrogen atom that can optionally have 1 or 2 heteroatoms as ring members, and provided that not all R1 are hydrogen,

more preferably hydrogen or a Ci-6 alkyl group, or two R1 are joined to form a 5- or 6-membered ring with the nitrogen, optionally further containing a nitrogen or oxygen atom as a ring member, and provided that not all R1 are hydrogen

most preferably hydrogen or a Ci-2 alkyl group, or two R1 are joined to form a morpholine, and provided that not all R1 are hydrogen.

8. The method or composition of claim 7, wherein L is an organic phosphine of formula

P

I

R3

wherein each R3 is independently

a Ci-12 hydrocarbyl group,

preferably a Ci-8 alkyl group, a C3-8 cycloalkyl group, or a C6-10 aromatic group, more preferably a Ci-6 alkyl group or Ce aromatic group,

most preferably a C1-4 alkyl group or Ce aromatic group.

9. The method or composition of claim 6, wherein L is a C2-20 thioether of the formula


wherein each R2 is independently

a Ci-io hydrocarbyl group,

preferably a Ci-8 alkyl group, a C3-8 cycloalkyl group, a C3-7 heterocycloalkyl group, a C6-10 aromatic group, or a C3-15 heteroaromatic group,

more preferably a Ci-6 alkyl group,

most preferably a C1-2 alkyl group.

10. The method or composition of claim 6, wherein L is

a C3-18 aliphatic heterocycle with 3 to 12 ring members wherein 1, 2, or 3 ring members are each independently nitrogen, oxygen, phosphorus, silicon, or sulfur;

preferably a C3-12 aliphatic heterocycle with 3 to 8 ring members wherein 1, 2, or 3 ring members are each independently nitrogen, oxygen, or sulfur,

more preferably a C3-12 aliphatic heterocycle with 5 to 7 ring members wherein 1 or 2 ring members are each independently nitrogen, oxygen, or sulfur,

still more preferably


wherein

each R4 is independently a Ci-6 alkyl group, a Ci-6 alkoxy group, a halogen, nitrile, or nitro group,

R5 is hydrogen or a Ci-6 alkyl group,

e is 0 to 4, preferably 0,

f is 0 to 3, preferably 0,

n is 1 to 2, and

m is 1 to 2, preferably 2;

most preferably an aliphatic heterocycle of the formulas


11. The method or composition of claim 6, wherein L is

a C3-18 aromatic heterocycle with 1 to 3 rings and 5 to 14 ring members wherein 1, 2, or 3 ring members are each independently nitrogen, oxygen, or sulfur;

preferably a C3-18 aromatic heterocycle with 1 or 2 rings and 5 to 10 ring members wherein 1, 2, or 3 ring members are each independently nitrogen, oxygen, or sulfur,

more preferably a C3-18 aromatic heterocycle with 1 ring and 5 or 6 ring members wherein 1, 2, 3 ring members are each independently nitrogen, oxygen, or sulfur,

most preferably an aromatic heter of the formula


wherein

each R6 is independently a Ci-12 hydrocarbyl group, preferably a Ci-8 alkyl group, a C3-8 cycloalkyl group, or a C6-io aromatic group, more preferably a Ci-6 alkyl group, and

f is 0 to 5;

most preferably wherein L is pyridine.

12. The method or composition of claim 6, wherein L is ammonia, dimethylamine, trimethylamine, triethylamine, tetrahydrofuran, morpholine, or pyridine.

13. The method of any one or more of claims 1 to 11, wherein contacting is with 1 to 5,000 ppm by weight of the borane complex, or 5 to 2,000 ppm, or 5 to 1,000 ppm, based on the weight of the alkanolamine.

14. The method or composition of any one or more of claims 1 to 13, wherein the borane complex is dissolved in a solvent before contacting, preferably an aqueous or alcoholic solvent, preferably an aqueous or a Ci-2 alcoholic solvent.

15. The method or composition of claim 13, wherein the concentration of the borane complex in the solvent is 1 to 30 wt%, based on total weight of the components, preferably 1 to 20 wt%, more preferably 1 to 20 wt%, even more preferably 1 to 10 wt%.

16. The method or composition of any one or more of claims 1 to 15, further comprising mixing the alkanolamine and the borane complex during or after the contacting.

17. The method or composition of any one or more of claims 1 to 16, wherein the contacting is at 20°C to 250°C, preferably 20°C to 40°C, more preferably 20°C to 30°C; andfor 10 minutes to 50 hours.

18. The method or composition of any one or more of claims 1 to 17, wherein the Platinum-Cobalt Color Value, Test Method ASTM D1209, does not increase by more than 40%, preferably more than 30%, or more preferably more than 20% for a period of six months to eight years, or one to eight years, or two to eight years, or three to seven years, or four to six years, after storage at room temperature.

19. The method or composition of any one or more of claims 1 to 18, wherein the Platinum-Cobalt Color Value, Test Method ASTM D1209, does not increase by more than 40%, preferably more than 30%, more preferably more than 20% for a period of one month to three years, or one month to two years, or three months to one year, or 4 to 8 months after storage at 45°C.

20. The composition of any one or more of claims 2 to 18, comprising less than 5 wt% of water, preferably less than 1 wt% of water, based on the total weight of the

triethanolamine.