US4575569A — Alkoxylation of thiols in the presence of a react…

Claim 1

Independent Claim 128 words

A process for the preparation of thiol alkoxylates which comprises (a) mixing (i) a secondary thiol reactant comprising one or more secondary C 6 to C 30 alkane thiols, (ii) a catalytically effective amount of a basic alkoxylation catalyst selected from the group consisting of alkali and alkaline earth metal oxides and hydroxides and mixture thereof, and (iii) between about 10 and 2000 percent by mole, based on catalyst, one or more thiol alkoxylates as are produced by the alkoxylation reaction of C 6 to C 30 alkane thiols and C 2 to C 4 alkylene oxides, (b) evaporating water from the resulting mixture, and (c) contacting the mixture, following water evaporation, with an alkylene oxide reactant comprising one or more C 2 to C 4 alkylene oxides.

Claim 2

Dependent Claim 128 words

A process for the preparation of thiol alkoxylates which comprises (a) mixing (i) a secondary thiol reactant comprising one or more secondary C 6 to C 30 alkane thiols, (ii) a catalytically effective amount of a basic alkoxylation catalyst selected from the group consisting of alkali and alkaline earth metal oxides and hydroxides and mixture thereof, and (iii) between about 10 and 2000 percent by mole, based on catalyst, one or more thiol alkoxylates as are produced by the alkoxylation reaction of C 6 to C 30 alkane thiols and C 2 to C 4 alkylene oxides, (b) evaporating water from the resulting mixture, and (c) contacting the mixture, following water evaporation, with an alkylene oxide reactant comprising one or more C 2 to C 4 alkylene oxides.

Claim 3

Dependent Claim 21 words

The process of claim 1, wherein the alkylene oxides are selected from the group consisting of ethylene oxide and propylene oxide.

Claim 4

Dependent Claim 39 words

The process of claim 2, wherein the quantity of thiol alkoxylates mixed with alkane thiol reactant and basic alkoxylation catalyst in step (a) is between about 20 and 1000 percent by mole, calculated on mols of basic alkoxylation catalyst.

Claim 5

Dependent Claim 19 words

The process of claim 3, wherein the thiol alkoxylates have an average alkylene oxide adduct number less than 5.

Claim 6

Dependent Claim 30 words

The process of claim 4, wherein the evaporation step is conducted under conditions sufficient to lower the water content of the mixture to less than about 50 ppm by weight.

Claim 7

Dependent Claim 27 words

The process of claim 5, wherein water is evaporated by heating the mixture of thiol reactant, catalyst, and promoter to a temperature in excess of 100° C.

Claim 8

Dependent Claim 19 words

The process of claim 6, wherein the mixture is heated under sparging with an inert gas or under vacuum.

Claim 9

Dependent Claim 27 words

The process of claim 7, wherein the mixture is heated to a temperature of at least 20° C. under sparging with nitrogen for at least 10 minutes.

Claim 10

Dependent Claim 39 words

The process of claim 8, wherein the quantity of thiol alkoxylates mixed with alkane thiol reactant and basic alkoxylation catlyst in step (a) is between about 50 and 700 percent by mole, calculated on mols of basic alkoxylation catalyst.

Claim 11

Dependent Claim 59 words

The process of claim 9, wherein the basic alkoxylation catalyst is selected from the group consisting of the oxides and hydroxides of sodium and potassium, the quantity of thiol alkoxylates in the mixture of step (a) is between about 50 and 500 percent by mol, and the thiol alkoxylates have an average alkylene oxide adduct number less than 5.

Claim 12

Dependent Claim 104 words

A process for the preparation of thiol alkoxylates which comprises (a) mixing (i) a secondary thiol reactant comprising one or more secondary C 6 to C 30 alkane thiols, (ii) a catalytically effective amount of one or more basic alkoxylation catalysts, and (iii) between about 10 and 2000 percent by mole, based on catalyst, of one or more thiol alkoxylates as are produced by the alkoxylation reaction of C 6 to C 30 alkane thiols and C 2 to C 4 alkylene oxides, and (b) contacting the mixture with an alkylene oxide reactant comprising one or more C 2 to C 4 alkylene oxides.

Claim 13

Dependent Claim 104 words

A process for the preparation of thiol alkoxylates which comprises (a) mixing (i) a secondary thiol reactant comprising one or more secondary C 6 to C 30 alkane thiols, (ii) a catalytically effective amount of one or more basic alkoxylation catalysts, and (iii) between about 10 and 2000 percent by mole, based on catalyst, of one or more thiol alkoxylates as are produced by the alkoxylation reaction of C 6 to C 30 alkane thiols and C 2 to C 4 alkylene oxides, and (b) contacting the mixture with an alkylene oxide reactant comprising one or more C 2 to C 4 alkylene oxides.

Claim 14

Dependent Claim 28 words

The process of claim 11, wherein the basic alkoxylation catalyst is selected from the group consisting of alkali and alkaline earth metal oxides and hydroxides and mixtures thereof.

Claim 15

Dependent Claim 21 words

The process of claim 12, wherein the alkylene oxides are selected from the group consisting of ethylene oxide and propylene oxide.

Claim 16

Dependent Claim 39 words

The process of claim 13, wherein the quantity of thiol alkoxylates mixed with alkane thiol reactant and basic alkoxylation catalyst in step (a) is between about 20 and 1000 percent by mole, calculated on moles of basic alkoxylation catalyst.

Claim 17

Dependent Claim 19 words

The process of claim 14, wherein the thiol alkoxylates have an average alkylene oxide adduct number less than 5.

Claim 18

Dependent Claim 28 words

The process of claim 15, wherein the one or more basic alkoxylation catalysts are selected from the group consisting of the oxides and hydroxides of sodium and potassium.

Claim 19

Dependent Claim 37 words

The process of claim 16, wherein the quantity of thiol alkoxylates mixed with alkane thiol reactant and basic alkoxylation catalyst in step (a) is between about 50 and 500 percent by mole, calculated on moles of catalyst.

Claim 20

Dependent Claim 138 words

In a process for the preparation of thiol alkoxylates which comprises steps for (a) mixing a thiol reactant comprising one or more C 6 to C 30 alkane thiols with a catalytically-effective amount of one or more basic alkoxylation catalysts and (b) contacting the resulting mixture with an alkylene oxide reactant comprising one or more alkylene oxide compounds, wherein the mixture of the thiol reactant and the one or more basic alkoxylation catalysts in step (a) is characterized as a heterogeneous mixture, the improvement which comprises admixingin step (a) the thiol reactant and the one or more basic alkoxylation catalysts with between about 10 and 2000 percent by mole, calculated on moles of catalyst, of one or more thiol alkoxylates as are produced by the alkoxylation reaction of C 6 to C 30 alkane thiols with alkylene oxide.

Claim 21

Dependent Claim 138 words

In a process for the preparation of thiol alkoxylates which comprises steps for (a) mixing a thiol reactant comprising one or more C 6 to C 30 alkane thiols with a catalytically-effective amount of one or more basic alkoxylation catalysts and (b) contacting the resulting mixture with an alkylene oxide reactant comprising one or more alkylene oxide compounds, wherein the mixture of the thiol reactant and the one or more basic alkoxylation catalysts in step (a) is characterized as a heterogeneous mixture, the improvement which comprises admixingin step (a) the thiol reactant and the one or more basic alkoxylation catalysts with between about 10 and 2000 percent by mole, calculated on moles of catalyst, of one or more thiol alkoxylates as are produced by the alkoxylation reaction of C 6 to C 30 alkane thiols with alkylene oxide.

Claim 22

Dependent Claim 31 words

The process of claim 18, wherein the one or more basic alkoxylation catalysts are selected from the group consisting of alkali and alkaline earth metal oxides and hydroxides and mixtures thereof.

Claim 23

Dependent Claim 83 words

The process of claim 19, wherein the thiol reactant consists essentially of one or more alkane thiols having carbon numbers in the range from about 8 to 18, inclusive, the alkylene oxide reactant consists essentially of one or more alkylene oxides selected from the group consisting of ethylene oxide and propylene oxide, and the one or more admixed thiol alkoxylates are as produced by the alkoxylation reaction of C 8 to C 18 alkane thiols with ethylene oxide, propylene oxide or mixtures thereof.

Claim 24

Dependent Claim 34 words

The process of claim 20, wherein the quantity of thiol alkoxylates admixed with the thiol reactant and the one or more catalysts is sufficient to solubilize the one or more catalysts in the mixture.

Claim 25

Dependent Claim 35 words

The process of claim 21 which additionally comprises a process step for evaporating water from the mixture of thiol reactant, catalyst and thiol alkoxylate before contacting this mixture with alkylene oxide reactant in step (b).

Claim 26

Dependent Claim 25 words

The process of claim 22, wherein the basic alkoxylation catalyst is selected from the group consisting of the oxides and hydroxides of sodium and potassium.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1989-03-10	1989-09-09	1990-03-11	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1993-03-10	1993-09-09	1994-03-11	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1997-03-10	1997-09-09	1998-03-11	$7700.00	Window Closed / Lapsed

Alkoxylation of thiols in the presence of a reaction promoter

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