Integrated process for simultaneous production of oxo-alcohols and plasticizers

Patent metadata

Field	Value
Publication number	US-9926246-B2
Application number	US-201414888040-A
Country	US
Kind code	B2
Filing date	May 2, 2014
Priority date	May 3, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

Disclosed herein are methods and systems for the simultaneous production of oxo-alcohols comprising n-butanol, isobutanol, and 2-ethylhexanol. Also disclosed are methods and systems for simultaneous production of plasticizers using the disclosed oxo-alcohols.

First claim

What is claimed is:

1. A method for the simultaneous production of oxo-alcohols comprising:
(a) providing a propylene stream and a syngas stream;
(b) hydroformylating the propylene stream and syngas stream to produce a first aldehyde stream comprising n-butanal (NBAL) and isobutanal (IBAL);
(c) aldolizing at least a portion of the NBAL to produce a second aldehyde stream comprising 2-ethylhexenal (EPA); and
(d) mixing at least a portion of the first aldehyde stream and at least a portion of the second aldehyde stream to form a mixed stream and hydrogenating simultaneously the n-butanal (NBAL), isobutanal (IBAL), and 2-ethylhexenal (EPA) in the mixed stream to produce an alcohol stream comprising n-butanol, isobutanol, and 2-ethylhexanol;
wherein the hydrogenating is performed in a single hydrogenation reactor.

2. The method of claim 1 , wherein the hydroformylation is performed in the presence of a hydroformylation catalyst; and wherein the hydroformylation catalyst comprises a tri-phenylphosphine modified Rhodium catalyst.

3. The method according to claim 1 , further comprising separating at least a portion of the first aldehyde stream into a NBAL stream and an IBAL stream.

4. The method of according to claim 1 , wherein the aldolization is performed in the presence of a dimerization catalyst comprising triethylamine catalyst.

5. The method according to claim 1 , further comprising esterifying the alcohol stream with phthalic acid or anhydride to produce a phthalate stream comprising dibutyl phthalate, diisobutyl phthalate, and di-(2-ethylhexyl) phthalate;
wherein the esterification reaction is performed in a single esterification reactor;
wherein the esterification is performed in the presence of an esterification catalyst; and
wherein the esterification catalyst comprises tetraisopropyl titanate catalyst.

6. The method according to claim 1 , further comprising aldolizing at least a portion of the isobutanal (IBAL) stream with formaldehyde to produce a third aldehyde stream comprising hydroxypivaldehyde (HPA).

7. The method of claim 6 , wherein the aldolization is performed in the presence of an amine catalyst, and wherein the amine catalyst comprises triethylamine (TEA).

8. The method according to claim 6 , further comprising hydrogenating at least a portion of the third aldehyde stream to produce neopentylglycol.

9. The method according to claim 1 , wherein the method produces the oxo-alcohols and plasticizers, the method further comprising
(e) esterifying the alcohol stream with phthalic acid or anhydride to produce a phthalate stream comprising dibutyl phthalate, diisobutyl phthalate, and di-(2-ethylhexyl) phthalate;
wherein the esterification reaction is performed in a single catalytic reactor.

10. The method according to claim 6 , wherein the method produces the oxo-alcohols and plasticizers, the method further comprises
(e) wherein the hydrogenating further comprises hydrogenating simultaneously at least a portion of the first aldehyde stream, the second aldehyde stream, and the third aldehyde stream to produce the alcohol stream which further comprises neopentylglycol;
and further comprising
(f) esterifying the alcohol stream which further comprises the neopentylglycol with phthalic acid or anhydride to produce a phthalate stream comprising dibutyl phthalate, diisobutyl phthalate, and di-(2-ethylhexyl) phthalate;
wherein the esterification reaction is performed in a single catalytic reactor.

Assignees

• Saudi Basic Ind Corp

Inventors

• Hashmi Syed Azhar
• Al-Anazi Flaiyh
• Al-Nafissa Abdullah

Classifications

• C07C29/175

  with simultaneous reduction of an oxo group · CPC title

• B01J31/2419

  comprising P as ring member · CPC title

• C07C45/74

  combined with dehydration · CPC title

• B01J25/02

  Raney nickel · CPC title

• C07C45/72

  by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups · CPC title