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Branched trialkylamine precursors, intermediates, products made therefrom and processes of manufacture

a trialkylamine and precursor technology, applied in the field of organic chemistry, can solve the problems of increasing energy and facilities usage, affecting the performance of individual hydrophobes in the mixture, and not being known to perform as well as the mixtures, and achieves the effects of low foaming, effective oily soil and/or stain removal, and mild skin

Inactive Publication Date: 2019-07-18
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes a need for new compositions, such as surfactants, with specific properties including low foaming, mildness to skin, effective removal of oily soil and stains, compatibility with other ingredients in a cleaning formula, high solubility in water, no gelling, ease of formulation, and biodegradability. The patent also describes the use of these compositions for various applications such as oily soil removal and animal fat removal.

Problems solved by technology

The processing of producing detergent alcohols adds considerably to energy and facilities usage and consequently to product cost.
When mixtures of hydrophobes are used to make surfactants, the individual hydrophobes in the mixture are not known to perform as well as the mixtures.

Method used

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  • Branched trialkylamine precursors, intermediates, products made therefrom and processes of manufacture
  • Branched trialkylamine precursors, intermediates, products made therefrom and processes of manufacture
  • Branched trialkylamine precursors, intermediates, products made therefrom and processes of manufacture

Examples

Experimental program
Comparison scheme
Effect test

example 1

of C11 Enal (4-ethyl-2-methyloct-2-enal)

[0350]

[0351]To a solution of NaOH (250 g, 3.12 mol) in water (303 mL) was added tributylmethylammonium chloride (49 g, 0.156 mol). To this solution, a premix solution of 2-ethyl hexaldehyde (500 g, 3.90 mol) and propionaldehyde (190 g, 3.28 mol) was added dropwise over the period of 5 h. The addition was maintained such that the temperature of the reaction did not exceed 55° C. The contents of the reaction were stirred at 50° C. for 12 h. The reaction was cooled to room temperature and the contents were transferred to a separatory funnel. The aqueous layer was separated and the organic layer was washed sequentially with water (500 mL), saturated aq. NH4Cl (500 mL) and water (500 mL). The organic layer was separated, dried over MgSO4 and filtered. The pure enal of this Example was distilled at 85° C. (vapour temperature) under 4 mm reduced pressure.

example 2

of C11 enal 4-ethyl-2-methyloctanal (C11-aldehyde)

[0352]

[0353]The C11-enal obtained in Example 1 was hydrogenated using palladium (Pd)—C (1 mol %) under hydrogen pressure (400 psi) at 120° C. The resultant aldehyde in this Example 2, 4-ethyl-2-methyloctanal, was distilled at 80° C.-85° C. (vapor temperature) under 3 mm reduced pressure.

example 3

of 2,4-diethyl-2-octenal

[0354]Charge a 3 neck, 1 L (liter) flask with Water (133 ml), sodium hydroxide (56.7 g, 1418 mmol), and tetrabutylammonium chloride (25.0 g, 90 mmol). Using a magnetic stir bar, stir to dissolve. Attach a 500 mL liquid dropping funnel charged with butyraldehyde (75.1 g, 1042 mmol) and 2-ethylhexanal (257.2 g, 2006 mmol). Add the aldehyde mixture to the aqueous mixture in the pot dropwise over 2-3 h. After aldehyde addition is complete, pour the mixture into a 1 L separatory funnel. Separate the aqueous layer and wash the organic layer with brine (1×100 mL) and water (2×100 mL). Separate the organic layer, dry over MgSO4, and filter. The crude reaction mixture (190 g) contains 46% 2-ethylhexanal and 33% 2,4-diethyloct-2-enal. This corresponds to 100% conversion of n-butyraldehyde and 56.9% yield, based on moles of butyraldehyde, of 2,4-diethyloctenal.

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Abstract

The invention provides branched hydrophobes for the production of surfactants with improved properties over linear hydrophobes. The invention also provides branched C10-12 enals and aldehydes that are oxidized to branched fatty acids or hydrogenated to branched fatty alcohols and further derivatized to surfactants, through ethoxylation or esterification and other or subsequent reactions. The invention further provides surfactants made from the branched trialkylamine intermediates, including amphoteric, cationic and nonionic surfactants.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority under 35 U.S.C. 119(e) to U.S. Provisional Application Ser. No. 62 / 616,502 filed Jan. 12, 2018, which is incorporated herein by reference in its entirety.FIELD OF THE INVENTION[0002]The invention generally relates to the field of organic chemistry. It particularly relates to branched trialkylamines, products made therefrom, and related methods of manufacturing. It further relates to surfactants made from branched trialkylamines and end-uses therefor.BACKGROUND OF THE INVENTION[0003]There is a commercial need for novel surfactants with desirable properties such as low foaming, effective oily soil removal, performance in cold water, compatibility with other ingredients in a cleaning formula, mildness to skin, and a favorable environmental and safety profile.[0004]A common trialkylamine hydrophobe used to make surfactants is dimethyl alkyl amine, made from C12 and C14 fatty alcohols reacted with dimethylamine...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C211/04C07C229/12A61Q5/02A61Q19/10A61K8/41A61K8/46C07C309/14C07H5/06C11D1/90C11D11/00A61K8/44
CPCC07C211/04C07C229/12A61Q5/02A61Q19/10A61K8/416A61K8/466C07C309/14C07H5/06C11D1/90C11D11/0023C11D11/0017A61K8/44C07C291/04C07C311/32C07C211/08C07C215/10C07C45/62C07C45/74C07C211/63C11D1/75C09K8/584C09K8/524A01N41/08A01N37/44C09D7/63C07C47/21C07C47/02C07C207/02C07C201/00C11D1/83C11D1/835C11D1/94C10L1/18C11D3/3942C11D3/43C11D3/395C11D2111/12C11D2111/14C07C2601/16A01N33/12B01J31/0239C07C45/72C07C209/22C07C211/64
Inventor CLENDENNEN, STEPHANIE KAYBHONDE, VASUDEV R.BILLODEAUX, DAMON RAYBOONE, MATTHEW ALLENDUMOLEIJN, KIMVAN DE VYVER, STIJN SIMONNE PAULMOONEN, KRISTOFBOAZ, NEIL WARREN
Owner EASTMAN CHEM CO
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