# US 5,350,521 A · Process for separating catalysts from organic solutions, by means of semipermeable membranes

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- Number: US 5,350,521 A
- Document ID: US5350521A
- Status: Granted
- Kind: A
- Application number: 08/111,280
- Filed: 1993-08-24
- Granted: 1994-09-27
- Earliest claimed: 1992-09-01
- Assignees: Eniricerche S.p.A.
- Inventors: Nunzio Andriollo; Giorgio Cassani; Paolo D'Olimpio; Bruno Donno; Marco Ricci
- Web page: https://patentgrep.com/patent/US5350521A

## CPC

- B01J 31/4053: {with recovery of phosphorous catalyst system constituents}
- B01D 61/145: {Ultrafiltration}
- B01J 31/0239: {Quaternary ammonium compounds}
- B01J 31/0268: {Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous}
- B01J 31/34: of chromium, molybdenum or tungsten
- B01J 31/4015: {of catalysts containing metals}
- B01J 31/4061: {involving membrane separation}
- B01J 38/00: Regeneration or reactivation of catalysts, in general
- C07D 301/12: with hydrogen peroxide or inorganic peroxides or peracids
- C07D 301/32: Separation; Purification
- C07D 303/42: Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
- C11B 3/008: {by filtration, e.g. including ultra filtration, dialysis (C11B3/005 takes precedence)}
- C11C 3/006: {by oxidation}
- B01J 2231/72: Epoxidation
- Y02P 20/584: Recycling of catalysts
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Disclosed is a process for separating metal catalysts based on ammonium and phosphonium phosphotungstates from reaction mixtures in which they are dissolved. The process is based on the use of semipermeable membranes and has found an useful application in the separation of the above said catalysts from mixtures obtained from alkenes and soybean oil epoxidation.

## Claims

### Claim 1

An ultrafiltration process for separating catalyst(s) from an organic solution in which the catalyst or catalysts are dissolved, the catalyst(s) consisting essentially of phosphotungstates or arsenotungstates as an anionic portion and ammonium or phosphonium salts as a counter-ion having surfactant characteristics, which process comprises the step of passing the catalyst-containing organic solution through an ultrafiltration membrane having an exclusion molecular weight sufficient to retain some of the catalyst(s) and to form, as a permeate, an organic solution containing a reduced concentration of the dissolved catalyst(s) and, as a retenate, an organic solution having an increased concentration of the dissolved catalyst(s).

### Claim 2 (depends on 1)

Process according to claim 1, wherein the ultrafiltration membrane is based on aluminum oxides or graphite and metal oxides.

### Claim 3 (depends on 1)

Process according to claim 1, wherein the ultrafiltration membrane is based on fluorinated polymers.

### Claim 4 (depends on 1)

Process according to claim 1, wherein the ultrafiltration membrane has an exclusion molecular weight of from 5,000 to 50,000 Da.

### Claim 5 (depends on 4)

Process according to claim 4, characterized in that the ultrafiltration wherein the ultrafiltration membrane has an exclusion molecular weight of from 10,000 to 15,000 Da.

### Claim 6 (depends on 1)

Process according to claim 1, wherein the organic solution containing the dissolved catalyst is filtered before passing the solution through the ultrafiltration membrane.

### Claim 7 (depends on 1)

Process according to claim 1, wherein the organic solution is an alkene solution.

### Claim 8 (depends on 1)

Process according to claim 1, wherein the organic solution is a reaction mixture obtained from a homogeneous catalytic epoxidation of alkenes.

### Claim 9 (depends on 1)

Process according to claim 1, wherein the organic solution is a reaction mixture obtained from a homogeneous catalytic epoxidation of soybean oil.

### Claim 10 (depends on 1)

Process according to claim 1, wherein the temperature of the organic solution is kept at values from 0.degree. to 250.degree. C.

### Claim 11 (depends on 1)

Process according to claim 1, wherein the catalyst concentration is from 100 to 20,000 mg.l.sup.-1 in the retenate and from 0 to 150 mg.l.sup.-1 in the permeate.

### Claim 12 (depends on 1)

Process according to claim 1, wherein the process is carried out in a tangential ultrafiltration device.

### Claim 13 (depends on 1)

Process according to claim 1, wherein the catalyst is selected from the group consisting of tri[(di-n-hexadecyl)-dimethyl]ammonium tetra(diperoxotungsto)phosphate, tri[(di-n-hexadecyl)-dimethyl]ammonium tetra(diperoxotungsto)arsenate, trioctyl methyl ammonium tetra(diperoxotungsto)phosphate, trioctyl methyl ammonium tetra(diperoxotungsto)arsenate, [tributyl(n-hexadecyl)]phosphonium tetra(diperoxotungsto)phosphate, [tributyl(n-hexadecyl)]phosphonium tetra(diperoxotungsto)arsenate, and mixtures thereof.

### Claim 14 (depends on 1)

Process according to claim 1, wherein the process is carried out in a tangential ultrafiltration device equipped with a tubular membrane and wherein the permeate is recycled.

### Claim 15 (depends on 14)

Process according to claim 14, wherein the permeate flow rate is from 10 to 50 m..sup.3.h.sup.-1 per each m.sup.2 of membrane surface.

### Claim 16 (depends on 14)

Process according to claim 14, wherein the process is carried out under pressure in a tangential ultrafiltration device; wherein the ultrafiltration membrane is flat or tubular and has an exclusion molecular weight of from 5000 to 50,000 Da.

### Claim 17 (depends on 16)

Process according to claim 16, wherein the operating pressure is from 0.1 to 1 MPa.

### Claim 18 (depends on 14)

Process according to claim 14, wherein the recycle flow rate linear velocity is from 1 to 10 m.s.sup.-1.