US Pat. No. 9,604,898

OZONOLYSIS OPERATIONS FOR GENERATION OF REDUCED AND/OR OXIDIZED PRODUCT STREAMS

P2 Science, Inc., Woodbr...

1. A method comprising:
a) providing oxygen and hydrogen, wherein said oxygen treated with electricity to generate ozone; wherein said ozone is used
in ozonolysis of a fatty acid or a fatty acid ester in an ozone reactor;

b) inputting said fatty acid into said ozone reactor, in which said fatty acid or fatty acid ester absorbs said ozone, thereby
forming a mixture comprising ozonated product stream comprising one or more compounds selected from ozonide, peroxide, aldehyde,
ester, and acid; and

c) generating partially reduced products comprising a linear alkyl aldehyde and oxygenated products comprising a diacid or
acid-ester from said ozonated product stream by:

i. partially reducing said ozonated product stream after said ozonated product stream enters a hydrogenation chamber to generate
said partially reduced products comprising largely a linear alkyl aldehyde, and contacting said partially reduced products
with water, forming two layers comprising an organic phase while leaving the hydrogenation chamber;

j. fractionating said organic phase to separate said linear alkyl aldehyde from the remaining organic phase; and
k. oxidizing the remaining organic phase after fractionation at step (j) after the remaining organic phase enters into an
oxidation chamber, resulting in the generation of said oxygenated products comprising said diacid or acid-ester;

thereby generating said linear alkyl aldehyde and said diacid or acid-ester from said ozonated product stream,
wherein the linear aldehyde, oxo-acid, oxo-ester, acid-ester, or diacid is more than about 95% pure.

US Pat. No. 9,783,520

MACROCYCLIC COMPOUNDS, POLYMERS, AND METHODS FOR MAKING SAME

P2 SCIENCE, INC., Woodbr...

1. A compound according to Formula I or Formula II:

or a salt thereof, wherein,
R1 is a bond, optionally substituted C1-C12 alkyl, optionally substituted C2-C12 alkenyl, or optionally substituted C2-C12 alkynyl;

R2 is optionally substituted C1-C12 alkyl, optionally substituted C2-C12 alkenyl, or optionally substituted C2-C12 alkynyl;

X is O or NRx;

Rx is hydrogen or optionally substituted C1-C12 alkyl;

Z is hydrogen or

one of the is a double bond and the other is a single bond;
m is an integer between 1 and 10; and
n is an integer between 1 and 100,000.

US Pat. No. 9,682,914

TERPENE-DERIVED ACIDS AND ESTERS AND METHODS FOR PREPARING AND USING SAME

P2 Science, Inc., Woodbr...

1. A method of producing a compound of formula (I):
or a salt thereof, wherein R1 is selected from the group consisting of H, unsubstituted or substituted C1-C10 alkyl, and unsubstituted or substituted C2-C10 alkenyl, and R2 is selected from the group consisting of H, unsubstituted or substituted C1-C10 alkyl, and CORa, in which Ra is H or unsubstituted or substituted C1-C10 alkyl, the method comprising:
reacting a compound having the formula IB
with ozone and subsequently with an oxidant different from ozone to obtain the compound of formula (I) wherein R1 is H; or alternatively
reacting a compound having the formula (IB) with ozone and subsequently with a reductant to obtain a mixture comprising the
compound of formula (I) wherein R1 is H and a compound of formula (IC):

and
separating the compound of formula (I) wherein R1 is H from the compound of formula (IC).

US Pat. No. 10,071,944

FILM OZONOLYSIS IN A TUBULAR OR MULTITUBULAR REACTOR

P2 SCIENCE, INC., Woodbr...

1. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using a tubular falling film reactor with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current, and wherein the gas flow rate is from 10 to 1500 L/min.

US Pat. No. 9,840,449

GUERBET ALCOHOLS AND METHODS FOR PREPARING AND USING SAME

P2 SCIENCE, INC., New Ha...

1. A method of producing a compound of formula I:
or a salt thereof, wherein each R independently is hydrogen or unsubstituted or substituted C1-C20 alkyl, wherein the alkyl
is linear or branched and optionally contains a carbonyl moiety (C?O) within or at the terminus of the alkyl chain, the method
comprising:
ozonolysis of a triglyceride, a fatty acid, or a fatty acid ester to obtain a mono-aldehyde having the formula R—CH2CHO; and
dimerizing the mono-aldehyde to obtain the compound of formula I, wherein the dimerization reaction is performed in an alcohol
aqueous solution.

US Pat. No. 10,011,582

SUBSTITUTED DELTA-LACTONES AND METHODS OF PREPARING SAME

P2 SCIENCE, INC., Woodbr...

1. A method of producing a compound of formula A,wherein the is a single bond or a double bond and RA is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl; the method comprising:(i) when the compound of formula A is of formula I:
reacting a compound of formula II:
with ozone to obtain a compound of formula III;wherein R1 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl and R2 is H, unsubstituted or substituted C1-C20 alkyl, or unsubstituted or substituted C2-C20 alkenyl;reacting the compound of formula III with a compound of formula IV:
in the presence of a metal to produce a reaction mixture, wherein Y is halo and R3 is unsubstituted or substituted C1-C20 alkyl unsubstituted or substituted C2-C20 alkenyl, or unsubstituted or substituted aryl; andoptionally treating the reaction mixture with an acid and/or heat to obtain the compound of formula I wherein R1 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl; or alternatively,(ii) when the compound of formula A is of formula V:
reacting a compound of formula VI
with ozone to obtain a compound of formula VII;wherein R5 is unsubstituted or substituted C1-C20 alkyl or unsubstituted or substituted C2-C20 alkenyl and R6 is unsubstituted or substituted C1-C10 alkyl;reacting the compound of formula VII with a compound of formula VIII: R4—X (VIII) in the presence of a metal to produce a reaction mixture, wherein X is halo and R4 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl; and
optionally treating the reaction mixture with an acid and/or heat to obtain the compound of formula V wherein R4 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl.
US Pat. No. 10,072,233

FRAGRANCE AND FLAVOR COMPOSITIONS COMPRISING NEOPENTYL GLYCOL DIACETATE

P2 SCIENCE, INC., Woodbr...

1. A fragrance composition comprising neopentyl glycol diacetate.

US Pat. No. 10,059,801

POLYETHERS, POLYAMINES, POLYTHIOETHERS, AND METHODS FOR MAKING SAME

P2 SCIENCE, INC., Woodbr...

1. A compound according to Formula I:
or a salt thereof, wherein,
R1 is a bond, optionally substituted C2-C12 alkyl, optionally substituted C2-C12 alkenyl, or optionally substituted C2-C12 alkynyl;
X is O, NH, or S;
one of the is a double bond and the other is a single bond; and
n is an integer between 2 and 100, provided that the compound of Formula I is not a compound wherein R1 is a bond, X is O and n is 2.

US Pat. No. 10,071,941

TERPENE-DERIVED COMPOUNDS AND METHODS FOR PREPARING AND USING SAME

P2 SCIENCE, INC., Woodbr...

1. A compound of Formula IV:
or a salt (hereof, wherein one of the is a single bond and the other is double bound, and R3 is unsubslitutcd or substituted C1-C10 alkyl,
wherein the compound is selected from 2,3,7-trimethyloct-6-en-2-ol, 2,3,7- trimcthyloct-7-en-2-ol, and salts thereof.
US Pat. No. 10,399,954

PREPARATION OF 3-HYDROXY-3,6-DIMETHYLHEXAHYDROBENZOFURAN-2-ONE AND DERIVATIVES THEREOF

P2 SCIENCE, INC., Woodbr...

1. A method of producing an ?-hydroxylactone, comprising the steps of:(a) forming a cyanohydrin intermediate from a hydroxy-ketone, wherein the hydroxy-ketone is 1-(2-hydroxy-4-methyl-cyclohexyl)ethanone, via cyanohydrin formation, wherein said cyanohydrin intermediate comprises a nitrile; and
(b) hydrolyzing and lactonizing said nitrile of said cyanohydrin intermediate in the presence of an aqueous acid to generate an ?-hydroxylactone, wherein said ?-hydroxylactone is 3-hydroxy-3,6-dimethylhexahydrobenzofuran-2-one.
US Pat. No. 10,428,001

FILM OZONOLYSIS IN A TUBULAR OR MULTITUBULAR REACTOR

P2 SCIENCE, INC., Woodbr...

1. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using an industrial scale tubular falling film reactor with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current, and wherein the ozonolysis occurs continuously without accumulation of large amounts of hazardous intermediates, and wherein the tubes are cooled by flow of a coolant; andwherein the gas flow rate is from 10 to 1500 L/min in each of said tube or tubes.

US Pat. No. 10,280,131

TERPENE-DERIVED ACIDS AND ESTERS AND METHODS FOR PREPARING AND USING SAME

P2 SCIENCE, INC., Woodbr...

1. A compound selected from the group consisting of:and salts thereof.