US 10,118,880 B2 · Process for the preparation of higher alcohols from ethanol and N-hexanol by guerbet condensation

Abstract

The present disclosure generally relates to processes for preparation of n-butanol, n-octanol and n-decanol from a reaction mixture comprising ethanoi and n-hexanol by Guerbet condensation. In some aspects, the present disclosure relates to improvements in n-octanol and n-decanol yield and selectivity by the selection of process reaction conditions such as, but not limited to, mole ratio of n-hexanol to ethanol. The present disclosure further generally relates to integrated processes for preparation of n-butanol in a n-butanol reactor from a reaction mixture comprising ethanol and hydrogen to produce a n-butanol product stream by Geurbet condensation comprising n-butanol and n-hexanol and for preparation of n-octanol in a n-octanol reactor from a reaction mixture comprising ethanol, n-hexanol and hydrogen to produce a n-octanol product stream by Geurbet condensation comprising n-butanol, n-hexanol and n-octanol. A predominant proportion of the n-hexanol contained in the n-butanol and n-octanol product streams is isolated and recycled to the n-octanol reaction mixture. In some aspects, the present disclosure relates to improvements in n-octanol and n-butanol yield and selectivity by the selection of process reaction conditions such as, but not limited to, mole ratio of n-hexanol to ethanol and recovery and recycle of n-hexanol.

Claims20

Dependent claims

A method of preparing n-octanol, the method comprising:

forming an octanol reaction mixture gas comprising a source of ethanol, a source of hydrogen, and a source of n-hexanol comprising at least 50 mole percent recovered n-hexanol, the octanol reaction mixture comprising a mole ratio ethanol to n-hexanol of from about 0.3:1 to about 3:1;
reacting the octanol reaction mixture gas in a continuous method by contact with a Guerbet heterogeneous metal oxide catalyst in a gas phase octanol reactor having a fixed catalyst bed at a reaction temperature of from about 150° C. to 450° C. and a reaction pressure of from about 10 to about 200 bara to form an octanol reactor product stream comprising ethanol, water, n-butanol, n-hexanol, n-octanol and hydrogen wherein the selectivity to n-octanol is at least 10% on a carbon basis and wherein the selectivity n-butanol is at least 10% on a carbon basis;
and
fractionating the octanol reactor product stream to form recovered n-hexanol, a n-butanol product stream and a n-octanol product stream.

1 more element

A continuous process for preparing n-butanol and n-octanol, the process comprising:

(a) (1) forming a gas phase n-butanol reaction mixture comprising a source of ethanol and a source of hydrogen, (2) reacting the gas phase n-butanol reaction mixture by contact with a Guerbet heterogeneous metal oxide catalyst in a gas-phase n-butanol reactor at a reaction temperature of from about 150° C. to 450° C. and a reaction pressure of from about 10 to about 200 bara to form a n-butanol reactor product stream comprising n-butanol and n-hexanol and (3) fractionating the n-butanol reactor product stream to form a n-butanol product stream and a recovered n-hexanol stream;
and
(b) (1) forming a gas phase n-octanol reaction mixture comprising a source of n-hexanol, a source of ethanol and a source of hydrogen, (2) reacting the gas phase n-octanol reaction mixture by contact with a Guerbet catalyst in a gas phase n-octanol reactor at a reaction temperature of from about 150° C. to 450° C. and a reaction pressure of from about 10 to about 200 bara to form a n-octanol reactor product stream comprising n-octanol, n-butanol and n-hexanol and (3) fractionating the n-octanol reactor product stream to form a n-octanol product stream, a recovered n-hexanol stream and a n-butanol product stream, wherein the source of n-hexanol comprises at least a portion of the n-hexanol stream recovered from the n-butanol reactor product stream.

A facility for manufacturing n-butanol and n-octanol from a source of ethanol and a source of n-hexanol, the facility comprising:

(a) a n-butanol reactor system comprising at least one gas phase reactor having a fixed catalyst bed containing a Guerbet heterogeneous metal oxide catalyst, the reactor comprising (1) an inlet for the input of a n-butanol reactor system feed stream gas comprising a source of ethanol and a source of hydrogen, (2) a reaction zone containing a heterogeneous catalyst for contact with the catalyst to form a n-butanol reactor product stream, and (3) an outlet for the discharge of a n-butanol reactor system product stream, the n-butanol reactor product stream comprising ethanol, water, n-butanol, n-hexanol, and hydrogen, wherein the n-butanol reactor system is operational at a reaction temperature of from about 150° C. to 450° C. and at a reaction pressure of from about 10 to about 200 bara;
(b) a n-octanol reactor system comprising at least one gas phase reactor having a fixed catalyst bed, the reactor comprising (1) an inlet for the input of a n-octanol reactor feed stream gas comprising a source of ethanol, a source of n-hexanol and a source of hydrogen, (2) a reaction zone containing a Guerbet heterogeneous metal oxide catalyst for contact with the reactor feed stream to form a n-octanol reactor product stream, and (3) an outlet for the discharge of the n-octanol reactor product stream, the n-octanol reactor product stream comprising ethanol, water, n-butanol, n-hexanol, n-octanol and hydrogen, wherein the n-octanol reactor system is operational at a reaction temperature of from about 150° C. to 450° C. and at a reaction pressure of from about 10 to about 200 bara;
(c) a first system for fractionating the n-butanol reactor product stream and the n-octanol reactor product stream, wherein the first fractionating system comprises a distillation column or a flash column that forms (1) a first fractionated stream comprising at least 95 mole percent each of the water, the ethanol and the hydrogen contained in the n-butanol reactor product stream and the n-octanol reactor product stream and (2) a second fractionated stream comprising at least 95 mole percent each of the n-butanol, the n-hexanol and the n-octanol contained in the n-butanol reactor stream and the n-octanol reactor product stream;
(d) a second system for fractionating the second fractionated stream, wherein the second fractionating system comprises a distillation column that forms (1) a n-butanol enriched stream comprising at least 95 mole percent of the n-butanol contained in the second fractionated stream and (2) a fourth fractionated stream comprising at least 95 mole percent each of the n-hexanol and the n-octanol contained in the second fractionated stream;
and
(e) a third system for fractionating the fourth fractionated stream, wherein the third fractionating system comprises a distillation column that forms (1) a recovered n-hexanol stream comprising at least 95 mole percent of the n-hexanol contained in the fourth fractionated stream, wherein the recovered n-hexanol stream is interconnected with the source of n-hexanol for the n-octanol reactor system and at least a portion of the recovered n-hexanol is recycled to the n-octanol reactor feed stream and (2) a n-octanol stream comprising at least 95 mole percent of the n-octanol contained in the fourth fractionated stream.

3 more elements

Dependencies are inferred from the claim text.

Process for the preparation of higher alcohols from ethanol and N-hexanol by guerbet condensation

Life of this patent

Process for the preparation of higher alcohols from ethanol and N-hexanol by guerbet condensation

Life of this patent

Abstract

Claims20