# US 8,785,694 B2 · Processes for the preparation of di-(2-aminoethyl) formal, di-(3-aminopropyl) formal, and related molecules

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- Number: US 8,785,694 B2
- Document ID: US8785694B2
- Status: Granted
- Kind: B2
- Application number: 13/910,612
- Filed: 2013-06-05
- Published: 2013-12-05
- Granted: 2014-07-22
- Earliest claimed: 2012-06-05
- Assignees: Connora Technologies, Inc.
- Applicants: Stefan J. Pastine
- Inventors: Stefan J. Pastine
- Web page: https://patentgrep.com/patent/US8785694B2

## CPC

- C07C 213/02: by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- Y02P 20/584: Recycling of catalysts
- Y02W 30/62: Plastics recycling; Rubber recycling
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02W: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT

## Abstract

Disclosed herein are hardeners for use in making cleavable epoxy compositions, including compositions wherein components in contact with epoxy composition can be recovered, as well as methods of making such hardeners.

## Claims

### Claim 1

A process of chemical synthesis for the preparation of di-(3-aminopropyl) formal acetal X:
said process comprising catalytic hydrogenation of a compound of formula
to produce the di-(3-aminopropyl) formal acetal X.

### Claim 2 (depends on 1)

The process of chemical synthesis of claim 1, wherein 2 molar equivalents of the compound of formula IX and 1 molar equivalent of paraformaldehyde are used.

### Claim 3 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation occurs under aqueous reaction conditions.

### Claim 4 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation uses a catalyst including, as an active component, a metal selected from the group consisting of Ru, Rh, Pd, and Pt.

### Claim 5 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation uses a catalyst including, as an active component, a metal selected from the group consisting of Cu, Cr, Co, Ni, and Fe.

### Claim 6 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation uses a catalyst including, as an active component, a bimetallic catalyst comprising one or more transition metals and/or noble metals.

### Claim 7 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted in liquid phase.

### Claim 8 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted at temperatures between 20° C. and 200° C.

### Claim 9 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted at hydrogen pressure between 1 and 1000 atmospheres.

### Claim 10 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted at a temperate between 60° C. and 150° C.

### Claim 11 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted under hydrogen pressure between 10 atmospheres and 110 atmospheres.

### Claim 12 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted in the presence of ammonia.

### Claim 13 (depends on 12)

The process of chemical synthesis of claim 12, wherein the ammonia is present in an amount between 1 mole to 20 moles per mole of the compound of Formula IX used.

### Claim 14 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted in the presence of anhydrous ammonia.

### Claim 15 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted in the presence of aqueous ammonia.

### Claim 16 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation is conducted in the presence of a solvent selected from the group consisting of methanol, ethanol, and dioxane.

### Claim 17 (depends on 1)

The process of chemical synthesis of claim 1, further comprising removing hydrogenation catalyst.

### Claim 18 (depends on 17)

The process of chemical synthesis of claim 17, wherein the hydrogenation catalyst is removed via filtration.

### Claim 19 (depends on 1)

The process of chemical synthesis of claim 1, further comprising purifying di-(3-aminopropyl) formal acetal of formula X.

### Claim 20 (depends on 19)

The process of chemical synthesis of claim 19, wherein di-(3-aminopropyl) formal acetal X is purified via distillation.

### Claim 21 (depends on 20)

The process of chemical synthesis of claim 20, wherein the distillation is conducted under reduced pressure.

### Claim 22 (depends on 1)

The process of chemical synthesis of claim 1, wherein the catalytic hydrogenation uses a catalyst selected from the group consisting of Raney catalysts and chromite catalysts.