# US 2014/0194647 A1 · Process for preparing di-substituted succinates

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0194647 A1
- Document ID: US20140194647A1
- Status: Published application
- Kind: A1
- Application number: 14/239,882
- Filed: 2012-08-23
- Published: 2014-07-10
- Earliest claimed: 2011-08-29
- Assignees: Saudi Basic Industries Corporation
- Inventors: Jaiprakash Brijlal Sainani; Mahesh Davadra
- Web page: https://patentgrep.com/patent/US20140194647A1

## CPC

- C08F 4/76: selected from titanium, zirconium, hafnium, vanadium, niobium or tantalum
- C07C 51/09: from carboxylic acid esters or lactones
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 67/343: by increase in the number of carbon atoms
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The invention relates to a process for preparing (2,3) disubstituted succinates that allows (2,3) disubstituted succinates to be obtained in good purity and with acceptable reaction yields. The (2) and (3) substitutions may be the same or different. The process comprises reacting a haloacetate with a malonic acid ester into a tricarboxylate, which is further reacted to a (2,3) disubstituted tricarboxylate, hydrolysed, decarboxylated and optionally esterified. Esterified (2,3) disubstituted succinic esters may be used as internal donor in Ziegler-Natta type catalysts for the polymerisation of olefins.

## Claims

### Claim 1

A process for preparing a 2,3 disubstituted succinate comprising the steps of:
a) reacting a compound [1] of formula
with a compound [2] of formula
to form a compound [3] of formula
followed by
b) reacting compound [3] with a compound of formula R2-X to form a compound [4] of formula
and
c) reacting compound [4] with a compound of formula R3-X to form a 2,3 disubstituted tricarboxylate compound [5] of formula
followed by
d) first hydrolysing compound [5] using an inorganic base and then decarboxylating the hydrolysed compound using an inorganic acid to yield a 2,3 disubstituted succinic acid compound [6] of formula
wherein R and R1 may be the same or different and are selected from the group consisting of branched or linear C1-C10 hydrocarbons, and
R2 and R3 may be the same or different and are selected from the group consisting of C1-C20 linear or branched alkyl, alkenyl, cycloalkyl, and alkylaryl, optionally containing heteroatoms, and
X is a halogen.

### Claim 2 (depends on 1)

The process according to claim 1 further comprising a step e) wherein at least one carboxylic acid groups of compound [6] is esterified using a compound of general formula R5-OH to obtain compound [7], wherein R5 is a C1-C20 linear or branched alkyl, alkenyl, cycloalkyl or alkylaryl group, optionally containing heteroatoms.

### Claim 3 (depends on 1)

The process according to claim 1 wherein compound [1] is used in an amount of 0.9-1.1 equivalents of compound [2].

### Claim 4 (depends on 1)

The process according to claim 1 wherein the amounts of R2-X and R3-X in steps b) and c) respectively are chosen such that in compound [5] an average molar ratio between R2 and R3 is from about 1 to about 2.

### Claim 5 (depends on 1)

The process according to claim 1 wherein steps b) and c) are carried out in a reaction medium comprising a protic solvents.

### Claim 6 (depends on 1)

The process according to claim 1 wherein the steps a), b) and c) are carried out in the presence of a base which may be the same or different for each of said steps and is a metal hydride having formula MH or a metal alkoxide of formula MOR4, wherein M is a metal of Group I of the Periodic Table of elements and R4 is selected from C1-C15 hydrocarbon groups.

### Claim 7 (depends on 6)

The process according to claim 6 wherein M is sodium or potassium.

### Claim 8 (depends on 1)

The process according claim 1 wherein the base is a metal alkoxide in step a) and a metal hydride in steps b) and c).

### Claim 9 (depends on 1)

The process according to claim 1 wherein the base in steps a), b) and c) is added in an amount of 1-2.5 equivalents based on the amount of the respective starting materials compound [2], compound [3] and compound [4].

### Claim 10 (depends on 1)

The process according claim 1 wherein the temperature in step a) is from 40° C. to 150° C. and wherein the temperature in steps b) and C) is from 10° C. to 100° C. and wherein the temperature in step d) is from 50° C. to 100° C. and wherein the temperature in step e) is from 40° C. to 110° C.

### Claim 11 (depends on 2)

Method for preparing a Ziegler Natta type catalyst comprising preparing the 2,3 disubstituted succinate according to claim 2 and reacting said 2,3 disubstituted succinate with a transition metal compound and a magnesium or silica containing support.