3-[(E)-dodec-1-enyl]oxolane-2,5-dione

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 liter Parr reactor equipped with a mechanical stirrer, bottom drain valve and distillation apparatus, was charged with NDC (111.0 g, 0.453 moles, 0.121 eq), PPG (211.0 g, 2.768 moles, 0.508 eq; excess 0.232 eq), terpinene-maleic anhydride adduct (42 g, 0.180 moles, 0.048 eq), Rosin-Ar (88 g, 0.249 moles, 0.0667 eq), DDSA (118 g, 0.445 moles, 0.119 eq), SA (53.0 g, 0.453 moles, 0.121 eq) followed by 1.0 g of both Fascat 4100 and Vertec AC422 titanium catalyst. About 0.4 g of hydroquinone were added as a free radical scavenger to prevent crosslinking of resin. The reactor was blanketed with nitrogen and the temperature of the reactor was slowly raised to 170° C. with stirring (once the solids melted). The reaction mixture was maintained for 15 hours under nitrogen at 205° C. while methanol was continuously collected in a collection flask. The reaction mixture was heated to 215° C. and low vacuum was applied. A higher vacuum (<0.1 Torr) was applied. During that time, propylene glycol distilled off and when the softening point of the resin reached 97.8° C., the reactor temperature was reduced to 180° C. and the second portion of terpinene-maleic anhydride (14 g, 0.058 moles, 0.0154 eq) was added. The reaction mixture temperature was slowly raised to 225° C. while under high vacuum for another 10 hours until a softening point of 103.5° C. was achieved. The temperature was then lowered to 190° C. and the polymer was discharged onto a polytetrafluoroethylene (Teflon) pan. A 1 liter Parr reactor equipped with a mechanical stirrer, bottom drain valve distillation apparatus was continuously collected in a collection flask The reaction mixture was heated to 215° C. During that time, propylene glycol distilled off reached 97.8° C. was reduced to 180° C. The reaction mixture temperature was slowly raised to 225° C. while under high vacuum for another 10 hours until a softening point of 103.5° C. was then lowered to 190° C.

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 liter Parr reactor equipped with a mechanical stirrer, bottom drain valve and distillation apparatus, was charged with NDC (111.0 g, 0.453 moles, 0.121 eq), PPG (211.0 g, 2.768 moles, 0.508 eq; excess 0.232 eq), terpinene-maleic anhydride adduct (42 g, 0.180 moles, 0.048 eq), Rosin-Ar (88 g, 0.249 moles, 0.0667 eq), DDSA (118 g, 0.445 moles, 0.119 eq), SA (53.0 g, 0.453 moles, 0.121 eq) followed by 1.0 g of both Fascat 4100 and Vertec AC422 titanium catalyst. About 0.4 g of hydroquinone were added as a free radical scavenger to prevent crosslinking of resin. The reactor was blanketed with nitrogen and the temperature of the reactor was slowly raised to 170° C. with stirring (once the solids melted). The reaction mixture was maintained for 15 hours under nitrogen at 205° C. while methanol was continuously collected in a collection flask. The reaction mixture was heated to 215° C. and low vacuum was applied. A higher vacuum (<0.1 Torr) was applied. During that time, propylene glycol distilled off and when the softening point of the resin reached 97.8° C., the reactor temperature was reduced to 180° C. and the second portion of terpinene-maleic anhydride (14 g, 0.058 moles, 0.0154 eq) was added. The reaction mixture temperature was slowly raised to 225° C. while under high vacuum for another 10 hours until a softening point of 103.5° C. was achieved. The temperature was then lowered to 190° C. and the polymer was discharged onto a polytetrafluoroethylene (Teflon) pan. A 1 liter Parr reactor equipped with a mechanical stirrer, bottom drain valve distillation apparatus was continuously collected in a collection flask The reaction mixture was heated to 215° C. During that time, propylene glycol distilled off reached 97.8° C. was reduced to 180° C. The reaction mixture temperature was slowly raised to 225° C. while under high vacuum for another 10 hours until a softening point of 103.5° C. was then lowered to 190° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A leaf of the transgenic plant was mixed with an extraction buffer solution (50 mM Tris-HCl, pH 6.8, 2% SDS, 6% 2-mercaptoethanol, 10% glycerol) having an amount eight times the weight of the leaf, followed by pulverization. The suspension was centrifuged at 12,000 rpm at 4° C. for 5 minutes, and thereafter, the supernatant was collected. The whole protein (10 μg) derived from each transformant was separated into individual proteins using 12.5% polyacrylamide gel, and the individual proteins were transferred onto Immobillon PVDF membrane (manufactured by Millopore). the supernatant was collected was separated into individual proteins

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A leaf of the transgenic plant was mixed with an extraction buffer solution (50 mM Tris-HCl, pH 6.8, 2% SDS, 6% 2-mercaptoethanol, 10% glycerol) having an amount eight times the weight of the leaf, followed by pulverization. The suspension was centrifuged at 12,000 rpm at 4° C. for 5 minutes, and thereafter, the supernatant was collected. The whole protein (10 μg) derived from each transformant was separated into individual proteins using 12.5% polyacrylamide gel, and the individual proteins were transferred onto Immobillon PVDF membrane (manufactured by Millopore). the supernatant was collected was separated into individual proteins

Conditions: temp:227.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 5 L-nitrogen-dried Büchi reactor, fitted with a mechanical stirrer, a sampling dip-leg, a vent, a rupture disk, a pressure sensor, a thermocouple well and a nitrogen inlet tube, was charged with propylene tetramer (2000 g, 1.75 eq.) and maleic anhydride (677 g, 1.0 eq.). The maleic anhydride was added as a solid (crushed briquettes from Aldrich) at room temperature. The reactor was then sealed and flushed with nitrogen for 5-10 min (5 psi of nitrogen was left in the reactor) before heat was applied. The mixture was heated up to 225-230° C. while stirring at 1000 rpm, the stirring being initiated when the reaction temperature had reached 55-60° C. The pressure built-up in the reactor was monitored with time and temperature (Pmax=54 psi). Sampling was performed during the course of the reaction until the desired conversion (followed by GC) with respect to maleic anhydride was achieved. After 4.5 hours of reaction, the reaction mass was cooled to 95° C. Butadiene (162 g; supplied by Matheson) was fed into the cooled reaction mixture through the inlet tube. After the butadiene addition, stirring was resumed without applying any additional heat. After two hours of reaction GC analysis showed that the maleic anhydride had been completely reacted. The contents of the reactor at a temperature of 55° C. were then discharged to a nitrogen-padded sample bottle while venting it with nitrogen. Analysis of the crude reaction mixture showed that it contained 54.96 wt % of DDSA, 5.68 wt % of THPA, 39.35 wt % of propylene tetramer and 0.01 wt % of maleic anhydride. Thus the weight ratio of the DDSA to THPA in this crude product was approximately 9.7:1. Unreacted starting materials (mostly residual olefin) were removed by flash distillation under reduced pressure using Kügelrohr equipment at an applied vacuum of 14.8 mmHg. After this purification, the product was a light yellow colored liquid. A 5 L-nitrogen-dried Büchi reactor fitted with a mechanical stirrer The reactor was then sealed flushed with nitrogen for 5-10 min (5 psi of nitrogen was left in the reactor) before heat had reached 55-60° C Sampling was performed during the course of the reaction until the desired conversion (followed by GC) with respect to maleic anhydride After 4.5 hours of reaction the reaction mass was cooled to 95° C stirring After two hours of reaction GC analysis had been completely reacted at a temperature of 55° C. Analysis of the crude reaction mixture were removed by flash distillation under reduced pressure After this purification

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The raw materials used in this operation were propylene tetramer supplied by Sunoco or Imperial Oil Esso and isoprene (99.5% pure) was supplied by Goodyear. A 1 L-nitrogen-dried stainless steel Parr reactor, fitted with mechanical stirrer, cooling coils, sampling dip-leg, vent, rupture disk, a pressure sensor, a thermocouple well, and a nitrogen inlet tube was charged with maleic anhydride (86.5 g, 1 eq.) and propylene tetramer (370 g, 2.5 eq.). The vessel was then bolted to the reactor frame and the reaction mixture was purged with nitrogen for 5-10 minutes. The mixture was then heated at 200° C. while stirring at 900 rpm, this stirring being initiated when the reaction temperature had reached 55-60° C., the temperature at which maleic anhydride melts. The pressure built-up in the reactor was monitored with time and temperature (Pmax=39 psi). Sampling was performed during the course of the reaction until the desired conversion (followed by GC) with respect to maleic anhydride was achieved. After the reaction was conducted for 4 hours the reaction mass was cooled to 80° C. by means of external cooling coils on the reactor mantel. Then isoprene (33 g) was introduced through the inlet tube into the reaction mixture. After the isoprene addition, stirring was resumed and the reaction mixture was heated at 100° C. for one hour. The GC analysis showed that no residual maleic anhydride remained in the reaction mixture. The hot reaction mixture was then cooled and the reactor was discharged to a nitrogen-padded sample bottle while venting it with nitrogen. Unreacted starting materials (mostly residual olefin and isoprene) were stripped off under reduced pressure using Kügelrohr equipment. Analysis of the purified light yellow liquid product showed that the product was composed of 83 wt % of DDSA and 17 wt % of MTHPA. A 1 L-nitrogen-dried stainless steel Parr reactor, fitted with mechanical stirrer cooling coils sampling dip-leg, vent, rupture disk the reaction mixture was purged with nitrogen for 5-10 minutes had reached 55-60° C. Sampling was performed during the course of the reaction until the desired conversion (followed by GC) with respect to maleic anhydride the reaction mass was cooled to 80° C. by means of external cooling coils on the reactor mantel stirring the reaction mixture was heated at 100° C. for one hour The hot reaction mixture was then cooled

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isolated soy protein (30 g) was dispersed in deionized water. The pH was adjusted to 8.5 with 1 N NaOH and the dispersion was heated to 50° C. Dodecenyl succinic anhydride (18 g) was dissolved in 100 ml of tetrahydrofuran. When the temperature of the soy dispersion reached 50° C., the DDSA/THF solution was added in 5 ml increments over 1 hour with concurrent adjustment of pH to 8.5 with 1 N NaOH. The solution was stirred for an additional hour to hydrolyze any unreacted anhydride. Protein was recovered by precipitation at pH 4.0 with 1 N HCl. The precipitate was washed and filtered three times with deionized water. The protein was dried at 60° C. and finely ground. Isolated soy protein (30 g) reached 50° C. Protein was recovered by precipitation at pH 4.0 with 1 N HCl The precipitate was washed filtered three times with deionized water The protein was dried at 60° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The experiments in Example 3 were repeated with tetrapropenylsuccininc anhydride (DDSA) instead of oleic acid. DDSA was supplied by Milliken Chemicals and had a neutralization number of 406 mg KOH/g. Milliken uses C12 branched-chain olefin derived from propylene tetramer to make DDSA.

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 liter Parr reactor equipped with a mechanical stirrer, bottom drain valve and distillation apparatus, was charged with NDC (111.0 g, 0.453 moles, 0.121 eq), PPG (211.0 g, 2.768 moles, 0.508 eq; excess 0.232 eq), terpinene-maleic anhydride adduct (42 g, 0.180 moles, 0.048 eq), Rosin-Ar (88 g, 0.249 moles, 0.0667 eq), DDSA (118 g, 0.445 moles, 0.119 eq), SA (53.0 g, 0.453 moles, 0.121 eq) followed by 1.0 g of both Fascat 4100 and Vertec AC422 titanium catalyst. About 0.4 g of hydroquinone were added as a free radical scavenger to prevent crosslinking of resin. The reactor was blanketed with nitrogen and the temperature of the reactor was slowly raised to 170° C. with stirring (once the solids melted). The reaction mixture was maintained for 15 hours under nitrogen at 205° C. while methanol was continuously collected in a collection flask. The reaction mixture was heated to 215° C. and low vacuum was applied. A higher vacuum (<0.1 Torr) was applied. During that time, propylene glycol distilled off and when the softening point of the resin reached 97.8° C., the reactor temperature was reduced to 180° C. and the second portion of terpinene-maleic anhydride (14 g, 0.058 moles, 0.0154 eq) was added. The reaction mixture temperature was slowly raised to 225° C. while under high vacuum for another 10 hours until a softening point of 103.5° C. was achieved. The temperature was then lowered to 190° C. and the polymer was discharged onto a polytetrafluoroethylene (Teflon) pan. A 1 liter Parr reactor equipped with a mechanical stirrer, bottom drain valve distillation apparatus was continuously collected in a collection flask The reaction mixture was heated to 215° C. During that time, propylene glycol distilled off reached 97.8° C. was reduced to 180° C. The reaction mixture temperature was slowly raised to 225° C. while under high vacuum for another 10 hours until a softening point of 103.5° C. was then lowered to 190° C.