Phosphate ester-type reaction product and method of preparing same

Claim 2

An organic phosphate ester composition having as a property the ability to increase the viscosity of kerosene when admixed in kerosene with sodium aluminate, said composition being prepared by the process which comprises the reaction of: A. a pentavalent phosphorus compound selected from the group consisting of P 2 O 5 and a mixture of P 2 O 5 with polyphosphoric acid; B. a hydroxy ether of the formula ROR 1 OH wherein R is a C 1 to C 6 alkyl group, R 1 is a C 2 or C 3 alkylene group and the total carbon atoms of R and R 1 range from 3 to about 8; and C. when the total carbon atoms of R and R 1 and is 3 or 4, a long chain substantially unsubstituted monohydric aliphatic alcohol containing at least 5 carbon atoms, but when the total carbon atoms of R and R 1 is 5 to 8, an alcohol selected from the group consisting of a long chain substantially unsubstituted monohydric aliphatic alcohol containing at least 5 carbon atoms, a short chain substantially unsubstituted monohydric aliphatic alcohol containing from 1 to 4 carbon atoms and a mixture of said alcohols, the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 being within the ranges of 0.4:1 to 4.5:1; 0:1 to 4.0:1 and 0:1 to 5.0:1 respectively, said reaction being conducted at temperature ranging from about 70° to about 90° C. for a period of time of from about 1.5 to about 6 hours, and said pentavalent phosphorus compound, hydroxy ether, and alcohol or alcohols being provided in molar ratios and admixed in a sequence effective to provide a reaction product suitable for use in increasing the viscosity of kerosene.

Claim 3

The reaction product of claim 1 wherein each alcohol is unsubstituted.

Claim 4

The reaction product of claim 2 wherein the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to P 2 O 5 are within the ranges of 0.8:1 to 1.8:1; 0:1 to 1.4:1; and 0.9:1 to 2.0:1 respectively.

Claim 5

The reaction product of claim 3 wherein the total mole ratio of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 ranges from about 2.8:1 to about 7.0:1.

Claim 6

The reaction product of claim 1 wherein the pentavalent phosphorus compound is P 2 O 5 .

Claim 7

The reaction product of claim 1 wherein the long chain monohydric alcohol contains from 5 to about 12 carbon atoms.

Claim 8

The reaction product of claim 6 wherein the short chain alcohol is a primary, unsubstituted, straight chain, saturated alcohol.

Claim 9

The reaction product of claim 7 wherein the short chain alcohol is ethanol, methanol, or a mixture thereof, and the long chain alcohol is unsubstituted.

Claim 10

The reaction product of claim 8 wherein the short chain alcohol is methanol.

Claim 11

The reaction product of claim 1 wherein the total mole ratio of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 is about 3.64 to 1.

Claim 12

The reaction product of claim 1 wherein the reaction temperature ranges from about 80° to about 90° C. and the reaction time ranges from about 1.5 to about 3 hours.

Claim 13

The reaction product of claim 1 werein when the total carbon atoms of R and R 1 is 3 or 4 there is also reacted a short chain substantially unsubstituted monohydric aliphatic alcohol containing from 1 to 4 carbon atoms or a mixture of said alcohols.

Claim 14

The reaction product of claim 12 wherein the long chain alcohol is unsubstituted and contains from 5 to 12 carbon atoms, and wherein the short chain alcohol is methanol, ethanol, or a mixture thereof.

Claim 15

An organic phosphate ester composition prepared by the process which comprises the reaction of: A. a pentavalent phosphorus compound, selected from the group consisting of P 2 O 5 and a mixture of P 2 O 5 with polyphosphoric acid; B. a hydroxy ether of the formula ROR 1 OH wherein R is a C 1 to C 6 alkyl group, R 1 is a C 2 or C 3 alkylene group and the total carbon atoms of R and R 1 range from 3 to about 8; and C. when the total carbon atoms of R and R 1 is 3 or 4 a long chain substantially unsubstituted monohydric aliphatic alcohol containing at least 5 carbon atoms and a short chain substantially unsubstituted monohydric aliphatic alcohol containing from one to four carbon atoms; when the total carbon atoms of R and R 1 is five to eight a short chain substantially unsubstituted monohydric aliphatic alcohol containing from one to four carbon atoms; the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 being within the ranges of 0.4:1 to 4.5:1; 0:1 to 4.0:1 and 0:1 to 5:1 respectively, and the total mole ratio of said three components to total P 2 O 5 being from about 2.8:1 to about 7.0:1, said reaction being conducted by first reacting the phosphorus compound with the hydroxy ether, and when the total carbon atoms of R and R 1 is 3 or 4, also with the long chain alcohol for a period of time of from about 5 to about 30 minutes at a temperature of from about 70° to about 90° C., cooling the reaction mixture to below 70° C., adding the short chain alcohol to the reaction mixture and reacting the mixture at a temperature of from about 70° to about 90° C. for a period of time to provide a total reaction time of from about 1.5 to about 6 hours.

Claim 16

An organic phosphate ester composition prepared by the process which comprises the reaction of: A. a pentavalent phosphorus compound, selected from the group consisting of P 2 O 5 and a mixture of P 2 O 5 with polyphosphoric acid; B. a hydroxy ether of the formula ROR 1 OH wherein R is a C 1 to C 6 alkyl group, R 1 is a C 2 or C 3 alkylene group and the total carbon atoms of R and R 1 range from 3 to about 8; and C. when the total carbon atoms of R and R 1 is 3 or 4 a long chain substantially unsubstituted monohydric aliphatic alcohol containing at least 5 carbon atoms and a short chain substantially unsubstituted monohydric aliphatic alcohol containing from one to four carbon atoms; when the total carbon atoms of R and R 1 is five to eight a short chain substantially unsubstituted monohydric aliphatic alcohol containing from one to four carbon atoms; the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 being within the ranges of 0.4:1 to 4.5:1; 0:1 to 4.0:1 and 0:1 to 5:1 respectively, and the total mole ratio of said three components to total P 2 O 5 being from about 2.8:1 to about 7.0:1, said reaction being conducted by first reacting the phosphorus compound with the hydroxy ether, and when the total carbon atoms of R and R 1 is 3 or 4, also with the long chain alcohol for a period of time of from about 5 to about 30 minutes at a temperature of from about 70° to about 90° C., cooling the reaction mixture to below 70° C., adding the short chain alcohol to the reaction mixture and reacting the mixture at a temperature of from about 70° to about 90° C. for a period of time to provide a total reaction time of from about 1.5 to about 6 hours.

Claim 17

The reaction product of claim 14 wherein when the total carbon atoms of R and R 1 is five to eight there is also reacted with the pentavalent phosphorus compound and the hydroxy ether a long chain monohydric alcohol containing at least 5 carbon atoms prior to reacting the short chain alcohol.

Claim 18

The reaction product of claim 14 wherein the long chain alcohol has 5 to 12 carbon atoms.

Claim 19

The reaction product of claim 14 wherein the pentavalent phosphorus compound is P 2 O 5 .

Claim 20

The reaction product of claim 14 wherein the short chain alcohol is a primary, unsubstituted, straight chain, saturated alcohol.

Claim 21

The reaction product of claim 18 wherein the short chain alcohol is ethanol, methanol, or a mixture thereof, and the long chain alcohol is unsubstituted.

Claim 22

The reaction product of claim 19 wherein the short chain alcohol is methanol.

Claim 23

The reaction product of claim 19 wherein the short chain alcohol is ethanol.

Claim 24

The reaction product of claim 14 wherein each alcohol is unsubstituted.

Claim 25

The reaction product of claim 22 wherein the long chain alcohol has 5 to 12 carbon atoms; the pentavalent phosphorus compound is P 2 O 5 ; and the short chain alcohol is primary, straight chain, and saturated.

Claim 26

The reaction product of claim 23 wherein said hydroxy ether is selected from the group consisting of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-n-hexyl ether, ethylene glycol monoisobutyl ether, propylene glycol monomethyl ether, propylene glycol monoisobutyl ether, propylene glycol monomethyl ether and mixtures thereof.

Claim 27

The reaction product of claim 24 wherein the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to P 2 O 5 are within the ranges of 0.8:1 to 1.8:1; 0:1 to 1.4:1; and 0.9:1 to 2.0:1 respectively.

Claim 28

The reaction product of claim 25 wherein the short chain alcohol is methanol, ethanol, or a mixture thereof.

Claim 29

The reaction product of claim 26 wherein the total mole ratio of the short chain alcohol, hydroxy ether and long chain alcohol to P 2 O 5 is about 3.64:1.

Claim 30

The reaction product of claim 27 wherein the short chain alcohol is methanol.

Claim 33

The method of claim 29 wherein each alcohol is unsubstituted.

Claim 34

The method of claim 30 wherein the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to P 2 O 5 are within the ranges of 0.8:1 to 1.8:1; 0:1 to 1.4:1; and 0.9:1 to 2.0:1 respectively.

Claim 35

The method of claim 31 wherein the total mole ratio of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 ranges from about 2.8:1 to about 7.0:1.

Claim 36

The method of claim 29 wherein the pentavalent phosphorus compound is P 2 O 5 .

Claim 37

The method of claim 29 wherein the long chain monohydric alcohol contains from 5 to about 12 carbon atoms.

Claim 38

The method of claim 34 wherein the short chain alcohol is a primary, unsubstituted, straight chain, saturated alcohol.

Claim 39

The method of claim 35 wherein the short chain alcohol is ethanol, methanol, or a mixture thereof, and the long chain alcohol is unsubstituted.

Claim 40

The method of claim 36 wherein the short chain alcohol is methanol.

Claim 41

The method of claim 29 wherein the total mole ratio of the hydroxy ether, the long chain alcohol and the short chain alcohol to total P 2 O 5 is about 3.64 to 1.

Claim 42

The method of claim 29 wherein the reaction temperature ranges from about 80° to about 90° C. and the reaction time ranges from about 1.5 to about 3 hours.

Claim 43

The method of claim 29 wherein when the total carbon atoms of R and R 1 is 3 or 4 there is also reacted a short chain substantially unsubstituted monohydric aliphatic alcohol containing from 1 to 4 carbon atoms or a mixture of said alcohols.

Claim 44

The method of claim 40 wherein the long chain alcohol is unsubstituted and contains from 5 to 12 carbon atoms, and wherein the short chain alcohol is methanol, ethanol, or a mixture thereof.

Claim 47

The method of claim 42 wherein when the total carbon atoms of R and R 1 is five to eight there is also reacted with the pentavalent phosphorus compound and the hydroxy ether a long chain monohydric alcohol containing at least 5 carbon atoms prior to reacting the short chain alcohol.

Claim 48

The method of claim 42 wherein the long chain alcohol has 5 to 12 carbon atoms.

Claim 49

The method of claim 42 wherein the pentavalent phosphorus compound is P 2 O 5 .

Claim 50

The method of claim 42 wherein the short chain alcohol is a primary, unsubstituted, straight chain, saturated alcohol.

Claim 51

The method of claim 46 wherein the short chain alcohol is ethanol, methanol, or a mixture thereof, and the long chain alcohol is unsubstituted.

Claim 52

The method of claim 47 wherein the short chain alcohol is methanol.

Claim 53

The method of claim 47 wherein the short chain alcohol is ethanol.

Claim 54

The method of claim 42 wherein each alcohol is unsubstituted.

Claim 55

The method of claim 50 wherein the long chain alcohol has 5 to 12 carbon atoms; the pentavalent phosphorus compound is P 2 O 5 ; and the short chain alcohol is primary, straight chain, and saturated.

Claim 56

The method of claim 51 wherein said hydroxy ether is selected from the group consisting of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-n-hexyl ether, ethylene glycol monoisobutyl ether, propylene glycol monomethyl ether, propylene glycol monoisobutyl ether, propylene glycol monomethyl ether and mixtures thereof.

Claim 57

The method of claim 52 wherein the individual mole ratios of the hydroxy ether, the long chain alcohol and the short chain alcohol to P 2 O 5 are within the ranges of 0.8:1 to 1.8:1; 0:1 to 1.4:1; and 0.9:1 to 2.0:1 respectively.

Claim 58

The method of claim 53 wherein the short chain alcohol is methanol, ethanol, or a mixture thereof.

Claim 59

The method of claim 54 wherein the total mole ratio of the short chain alcohol, hydroxy ether and long chain alcohol to P 2 O 5 is about 3.64:1.

Claim 60

The method of claim 55 wherein the short chain alcohol is methanol.