Olefins and methods for making the same

A method for making a mono-olefin terpene feedstock comprising:

• a) in a first stage, reacting a conjugated terpene comprising at least one conjugated diene and at least one olefinic bond in addition to the at least one conjugated diene with hydrogen in the presence of a first catalyst under a first condition suitable to preferentially hydrogenate at least one olefinic bond in the at least one conjugated diene to produce a partially hydrogenated intermediate, wherein the first condition comprises a type of first catalyst, a first catalyst loading, a reaction temperature, and a hydrogen pressure;
• and
• b) in a second stage, reacting the partially hydrogenated intermediate with hydrogen in the presence of a second catalyst under a second condition to produce a mono-olefin terpene feedstock comprising at least about 60% mono-olefins and less than about 25% alkanes, wherein the second condition comprises a type of second catalyst, a second catalyst loading, a reaction temperature, and a hydrogen pressure;
• and
• wherein at least one of the type of catalyst, catalyst loading, reaction temperature, and hydrogen pressure is varied between the first stage and the second stage such that all but one of the olefinic double bonds of the partially hydrogenated intermediate are hydrogenated in the second stage;
• wherein in the second stage, the type of the second catalyst, the second catalyst loading, the reaction temperature, or the hydrogen pressure is controlled to produce the mono-olefin terpene feedstock comprising at least about 60% mono-olefins and less than about 25% alkanes;
• and
• wherein the conjugated terpene is selected from the group consisting of a conjugated C15 terpene, a conjugated C20 terpene, and a conjugated C30 terpene.

A method for making a mono-olefin terpene feedstock comprising:

• a) in a first stage, reacting a conjugated terpene comprising at least one conjugated diene and at least one olefinic bond in addition to the at least one conjugated diene with hydrogen in the presence of a first catalyst under a first condition suitable to preferentially hydrogenate at least one olefinic bond in the at least one conjugated diene to produce a partially hydrogenated intermediate, wherein the first condition comprises a type of first catalyst, a first catalyst loading, a reaction temperature, and a hydrogen pressure;
• and
• b) in a second stage, reacting the partially hydrogenated intermediate with hydrogen in the presence of a second catalyst under a second condition to produce a mono-olefin terpene feedstock comprising at least about 55% mono-olefins and less than about 10% di-olefins, wherein the second condition comprises a type of second catalyst, a second catalyst loading, a reaction temperature, and a hydrogen pressure;
• and
• wherein at least one of the type of catalyst, catalyst loading, reaction temperature, and hydrogen pressure is varied between the first stage and the second stage such that all but one of the olefinic double bonds of the partially hydrogenated intermediate are hydrogenated in the second stage;
• wherein in the second stage, the type of the second catalyst, the second catalyst loading, the reaction temperature, or the hydrogen pressure is controlled to produce the mono-olefin terpene feedstock comprising at least about 55% mono-olefins and less than about 10% di-olefins;
• and
• wherein the conjugated terpene is selected from the group consisting of a conjugated C15 terpene, a conjugated C20 terpene, and a conjugated C30 terpene.

A method for making an olefinic feedstock comprising:

• a) in a first stage, reacting C15-C30 conjugated alkenes comprising at least one conjugated diene and at least one additional olefinic bond with hydrogen in the presence of a first catalyst under a first condition suitable to preferentially hydrogenate at least one olefinic bond in the at least one conjugated diene to produce partially hydrogenated intermediates, wherein the first condition comprises a type of first catalyst, a first catalyst loading, a reaction temperature, and a hydrogen pressure;
• and
• b) in a second stage, reacting the partially hydrogenated intermediates with hydrogen in the presence of a second catalyst under a second condition to produce an olefinic feedstock comprising at least about 55% mono-olefins, wherein the second condition comprises a type of second catalyst, a second catalyst loading, a reaction temperature, and a hydrogen pressure;
• wherein the type of catalyst, catalyst loading, reaction temperature, or hydrogen pressure is varied between the first stage and the second stage such that hydrogenation of partially hydrogenated intermediates having more than one olefinic bond is favored over hydrogenation of partially hydrogenated intermediates having one olefinic bond in the second stage;
• and
• wherein the hydrogen pressure in the second stage is about 10 to 100 psig.

A method for making an olefinic feedstock comprising:

• a) in a first stage, reacting C15-C30 conjugated alkenes comprising at least one conjugated diene and at least one additional olefinic bond with hydrogen in the presence of a first catalyst under a first condition suitable to preferentially hydrogenate at least one olefinic bond in the at least one conjugated diene to produce partially hydrogenated intermediates, wherein the conditions are selected such that 5% or less of the partially hydrogenated intermediates contain conjugated carbon-carbon double bonds, wherein the first condition comprises a type of first catalyst, a first catalyst loading, a reaction temperature, and a hydrogen pressure;
• and
• b) in a second stage, reacting the partially hydrogenated intermediates with hydrogen in the presence of a second catalyst under a second condition to produce an olefinic feedstock comprising at least about 55% mono-olefins, wherein the second condition comprises a type of second catalyst, a second catalyst loading, a reaction temperature, and a hydrogen pressure;
• wherein the type of catalyst, catalyst loading, reaction temperature, or hydrogen pressure is varied between the first stage and the second stage such that hydrogenation of partially hydrogenated intermediates having more than one olefinic bond is favored over hydrogenation of partially hydrogenated intermediates having one olefinic bond in the second stage.