US5214168A — Integrated process for epoxide production

Claim 1

Independent Claim 102 words

An integrated process for the production of an epoxide comprising the steps of (a) contacting an aryl-substituted secondary alcohol with molecular oxygen under conditions effective to form an oxidant mixture comprised of the secondary alcohol, an aryl-substituted ketone, and hydrogen peroxide; (b) contacting the oxidant mixture with an olefin and a catalytically effective amount of a titanium silicalite for a time and at a temperature effective to convert the olefin to the epoxide; and (c) reacting the aryl-substituted ketone with hydrogen in the presence of a transition metal hydrogenation catalyst under conditions effective to convert the ketone to the aryl-substituted secondary alcohol.

Claim 2

Dependent Claim 102 words

An integrated process for the production of an epoxide comprising the steps of (a) contacting an aryl-substituted secondary alcohol with molecular oxygen under conditions effective to form an oxidant mixture comprised of the secondary alcohol, an aryl-substituted ketone, and hydrogen peroxide; (b) contacting the oxidant mixture with an olefin and a catalytically effective amount of a titanium silicalite for a time and at a temperature effective to convert the olefin to the epoxide; and (c) reacting the aryl-substituted ketone with hydrogen in the presence of a transition metal hydrogenation catalyst under conditions effective to convert the ketone to the aryl-substituted secondary alcohol.

Claim 3

Dependent Claim 15 words

The process of claim 1 wherein the titanium silicalite has an MFI or MEL topology.

Claim 4

Dependent Claim 27 words

The process of claim 1 wherein the titanium silicalite has a composition corresponding to the chemical formula xTiO.sub.2 ·(1-x) SiO.sub.2 wherein x is from 0.0001 to 0.125.

Claim 5

Dependent Claim 55 words

The process of claim 1 wherein the aryl-substituted secondary alcohol has the general structure: ##STR4## wherein R and R 1 are the same or different and are selected from the group consisting of alkyl, aryl alkyl, and aryl groups with the proviso that at least one of R or R 1 is an aryl group.

Claim 6

Dependent Claim 37 words

The process of claim 1 wherein the aryl-substituted secondary alcohol has the general structure ##STR5## wherein R 2 and R 3 are the same or different and are selected from hydrogen and C 1 -C 10 alkyl.

Claim 7

Dependent Claim 64 words

The process of claim 1 wherein the olefin has the general formula ##STR6## wherein R 1 , R 2 , R 3 , and R 4 are the same or different and are selected from hydrogen, C 1 -C 20 alkyl, C 7 -C 20 aryl alkyl, C 5 -C 12 cycloalkyl, C 6 -C 20 alkyl cycloalkyl and C 6 -C 20 aryl.

Claim 8

Dependent Claim 21 words

The process of claim 1 wherein the amount of titanium silicalite is from 0.01 to 10 grams per mole of olefin.

Claim 9

Dependent Claim 22 words

The process of claim 1 wherein step (b) in said process is conducted at a pressure of between 1 and 100 atmospheres.

Claim 10

Dependent Claim 24 words

The process of claim 1 wherein the molar ratio of Si:Ti in the lattice framework of the titanium silicalite is from 9.5:1 to 99:1.

Claim 11

Dependent Claim 20 words

The process of claim 1 wherein the molar ratio of olefin:hydrogen peroxide in step (b) is from 1.10 to 10:1.

Claim 12

Dependent Claim 13 words

The process of claim 1 wherein methanol is additionally present during step (b).

Claim 13

Dependent Claim 18 words

The process of claim 1 wherein the temperature in step (b) is from 0° C. to 150° C.

Claim 14

Dependent Claim 23 words

The process of claim 1 wherein the titanium silicalite has been treated with an acid-neutralizing agent selected from alkaline substances and silylating agents.

Claim 15

Dependent Claim 26 words

The process of claim 1 comprising the additional step of separating the epoxide from the aryl-substituted secondary alcohol and the aryl-substituted ketone prior to step (c).

Claim 16

Dependent Claim 27 words

The process of claim 1 wherein the transition metal in the transition metal hydrogenation catalyst in step (c}is selected from palladium, platinum, chromium, rhodium, nickel, or ruthenium.

Claim 17

Dependent Claim 21 words

The process of claim 1 wherein step (c) is carried out at a temperature of from 0° C. to 200° C.

Claim 18

Dependent Claim 20 words

The process of claim 1 wherein step (c) is conducted at a hydrogen pressure of between 1 and 200 atmospheres.

Claim 19

Dependent Claim 19 words

The process of claim 1 wherein step (a) is conducted at a temperature of from 100 to 200° C.

Claim 20

Dependent Claim 19 words

The process of claim 1 wherein step (a) is conducted at a pressure of from 50 to 1000 psig.

Claim 21

Dependent Claim 16 words

The process of claim 1 wherein the oxidant mixture contains less than 4 weight percent water.

Claim 22

Dependent Claim 15 words

The process of claim 1 wherein contacting step (a}is carried out in a liquid phase.

Claim 23

Dependent Claim 175 words

An integrated process for the production of an epoxide comprising the steps of (a) contacting alpha-methyl benzyl alcohol with molecular oxygen at a temperature of from 100° C. to 200° C. and a pressure of from 50 to 1000 psig oxygen to form an oxidant mixture comprised of alpha-methyl benzyl alcohol, acetophenone, and from 1 to 10 weight percent hydrogen peroxide; (b) contacting the oxidant mixture with an olefin and from 0.01 to 10 grams titanium silicalite per mole of olefin having an MEL or MFI topology and a chemical formula xTiO.sub.2 ·(1-x)SiO.sub.2 wherein x is from 0.01 to 0.125, at a temperature of from 0° C. to 150° C. for a time effective to convert the olefin to epoxide; and (c) reacting the acetophenone with hydrogen in the presence of a transition metal hydrogenation catalyst wherein the transition metal is platinum, palladium, chromium, rhodium, nickel or ruthenium at a temperature of from 20° to 150° C. and a hydrogen pressure of from 1 to 200 atmospheres to convert the acetophenone to alpha-methyl benzyl alcohol.

Claim 24

Dependent Claim 175 words

An integrated process for the production of an epoxide comprising the steps of (a) contacting alpha-methyl benzyl alcohol with molecular oxygen at a temperature of from 100° C. to 200° C. and a pressure of from 50 to 1000 psig oxygen to form an oxidant mixture comprised of alpha-methyl benzyl alcohol, acetophenone, and from 1 to 10 weight percent hydrogen peroxide; (b) contacting the oxidant mixture with an olefin and from 0.01 to 10 grams titanium silicalite per mole of olefin having an MEL or MFI topology and a chemical formula xTiO.sub.2 ·(1-x)SiO.sub.2 wherein x is from 0.01 to 0.125, at a temperature of from 0° C. to 150° C. for a time effective to convert the olefin to epoxide; and (c) reacting the acetophenone with hydrogen in the presence of a transition metal hydrogenation catalyst wherein the transition metal is platinum, palladium, chromium, rhodium, nickel or ruthenium at a temperature of from 20° to 150° C. and a hydrogen pressure of from 1 to 200 atmospheres to convert the acetophenone to alpha-methyl benzyl alcohol.

Claim 25

Dependent Claim 24 words

The process of claim 22 wherein the olefin is selected from ethylene, propylene, 1-butene, isobutylene, 2-butene, 1-pentene, cyclohexene, allyl chloride, allyl alcohol, and butadiene.

Claim 26

Dependent Claim 16 words

The process of claim 22 wherein the oxidant mixture contains less than 4 weight percent water.

Claim 27

Dependent Claim 16 words

The process of claim 22 wherein contacting step (a) is carried out in a liquid phase.

Claim 28

Dependent Claim 23 words

The process of claim 22 wherein the Si:Ti molar ratio in the lattice framework of the titanium silicalite is from 9.5:1 to 60:1.

Claim 29

Dependent Claim 28 words

The process of claim 22 comprising the additional step of separating the epoxide from the aryl-substituted secondary alcohol and the aryl-substituted ketone by distillation prior to step (c).

Claim 30

Dependent Claim 23 words

The process of claim 22 wherein the titanium silicalite has been treated with an acid-neutralizing agent selected from alkaline substances and silylating agents.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1996-05-24	1996-11-23	1997-05-25	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2000-05-24	2000-11-23	2001-05-25	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2004-05-24	2004-11-23	2005-05-25	$7700.00	Window Closed / Lapsed

Integrated process for epoxide production

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