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Chemical Modification of Partially Hydrogenated Vegetable Oil To Iowa State University Patents Iowa State University Research Foundation, Inc. 11-13-2008 Chemical Modification of Partially Hydrogenated Vegetable Oil to Improve its Functional Properties to Replace Petroleum Waxes Tong Wang Iowa State University, [email protected] Liping Wang Iowa State University Follow this and additional works at: http://lib.dr.iastate.edu/patents Part of the Food Science Commons, and the Human and Clinical Nutrition Commons Recommended Citation Wang, Tong and Wang, Liping, "Chemical Modification of Partially Hydrogenated Vegetable Oil to Improve its Functional Properties to Replace Petroleum Waxes" (2008). Iowa State University Patents. 18. http://lib.dr.iastate.edu/patents/18 This Patent Application is brought to you for free and open access by the Iowa State University Research Foundation, Inc. at Iowa State University Digital Repository. It has been accepted for inclusion in Iowa State University Patents by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. Chemical Modification of Partially Hydrogenated Vegetable Oil to Improve its Functional Properties to Replace Petroleum Waxes Abstract A novel, chemically-modified partially hydrogenated vegetable oil (PHVO) is described. The PHVO is produced by a three-step reaction process that includes epoxidation, a ringopening reaction, followed by esterification. The modified PHVO has improved kneadability and, if mixed with fully hydrogenated fat(s ), hardness comparable to umnodified PHVO. Disciplines Food Science | Human and Clinical Nutrition This patent application is available at Iowa State University Digital Repository: http://lib.dr.iastate.edu/patents/18 111111 1111111111111111111111111111111111111111111111111111111111111111111111111111 US 20080281115Al (19) United States c12) Patent Application Publication (10) Pub. No.: US 2008/0281115 A1 Wang et al. (43) Pub. Date: Nov. 13, 2008 (54) CHEMICAL MODIFICATION OF PARTIALLY (22) Filed: May 1, 2008 HYDROGENATED VEGETABLE OIL TO IMPROVE ITS FUNCTIONAL PROPERTIES Related U.S. Application Data TO REPLACE PETROLEUM WAXES (60) Provisional application No. 60/917,510, filed on May 11, 2007. (75) Inventors: Tong Wang, Ames, IA (US); Publication Classification Liping Wang, Solana Beach, CA (US) (51) Int. Cl. CllB 3102 (2006.01) C07C 53100 (2006.01) Correspondence Address: MCKEE, VOORHEES & SEASE, P.L.C. (52) U.S. Cl. .......................... 554/149; 554/223; 554/167 801 GRAND AVENUE, SUITE 3200 (57) ABSTRACT DES MOINES, lA 50309-2721 (US) A novel, chemically-modified partially hydrogenated veg­ etable oil (PHVO) is described. The PHVO is produced by a (73) Assignee: IOWA STATE UNIVERSITY three-step reaction process that includes epoxidation, a ring­ RESEARCH FOUNDATION, opening reaction, followed by esterification. The modified INC., Ames, IA (US) PHVO has improved kneadability and, if mixed with fully hydrogenated fat(s ), hardness comparable to umnodified (21) Appl. No.: 12/113,464 PHVO. 140 ----r-----------------------. 120- .....- ·-0 100- I I :?C> :::..:::= I t:U) 80- I s I ai I ..e 60- I >~ I :::::.:::::: 40- I C> I o~----~~----~~----~~~--~~-----~~--~ 0 10 20 30 40 50 60 Reaction Time, Hr Patent Application Publication Nov. 13, 2008 Sheet 1 of 12 US 2008/0281115 A1 140 120- .....- ·-0 100- I I ~C) :::..::: I CO{) 80- I s I v I 60- I ..ecC > I :::t::: 40- I C) I 20- 0-r----~~----~~----~~~----~~----~~----~ 0 10 20 30 40 50 60 Reaction Time, Hr Fig.l 160 140- .....- /~----------~------~ 0 / ·- 120- / ~ I C) 100- :::..::: --* sCO{) f 80- J ..ev I cC 60- > + :::t::: C) 40- 20- 0 I I I I 0 5 10 15 20 25 Water to EPKLX Ratio Fig.2 Patent Application Publication Nov. 13, 2008 Sheet 2 of 12 US 2008/0281115 A1 30000---,------------------------, 15000 ' ' ' ' ,.,. ... ' ' 'I .. ~--------------------------------------------- ~-- ---- - --------------------- ......... -~...... ..... -------------------------------------------------- ... , /..... \ /,---------------- .... -15000 ------------- FHSO ; \ ! : ', : ~ : \ : -- 50% OHKLX ~\: : ·.\: : -- 100% OHKLX V \} -40 -20 0 20 40 60 BO 100 Temperature, oC Fig.3A 30000---,------------------------, KLX-OHKLX 15000 r.. ------------------------------------... ,:·'/ ____ ------------------------- __ , ............................... .. -15000 ------------- KLX ·· •.. ___ / --50% OHKLX -- 100% OHKLX -40 -20 0 20 40 60 80 100 Temperature, oC Fig.3B Patent Application Publication Nov. 13, 2008 Sheet 3 of 12 US 2008/0281115 A1 30000----.-------------------------, FHSO-BuoKLX 15000 ~ ...... ; ....... ____ ---------- --~---- ---------- .. ---------- .............. l\ ,.. ' ---------- ----" .. \ ! \ I -15000 \ : ~ : ------------- FHSO ' j ~ l \ : ~ : \ l \ i -- 50% BuoKLX \1 \ { -- 100% BuoKLX ~~ \1 -60 -40 -20 0 20 40 60 80 100 Temperature, oC Fig.3C 30000----.----------------------, KLX-BuoKLX 15000 --~-------_ ........... "' ,,. •. ----------- ~~ .............. -- .. _____________________ - .... ----------------------- ..... ; .............................. ,' ...... : -15000 ------------- KLX .. \·.... _...... -- 50% BuoKLX -- 100% BuoKLX -60 -40 -20 0 20 40 60 80 100 Temperature, oC Fig. 3D '"= ~...... ('D ......= 40000 I _ ~ 'e.... (')- --Beeswax ~.......... 0 --- BuoKLX = 30000 ='"= -----1r-- FHSO 0".... (')- *- KLX ~.......... 0 - OHKLX Slope ~ !:>0 = e/J­ Cparaffin e/J z .§ 20000 0 Csoywax ~ ...... ~ -- EPKLX (.H ~ N 0 0 QO rFJ ('D=­ ('D...... .j;o. 0...... ...... N 0 c 0.8 1.2 1.6 2 rFJ N 0 Distance, mm 0 ..._QO 0 N QO Fig.4 ...... ...... ...... Ul >...... Patent Application Publication Nov. 13, 2008 Sheet 5 of 12 US 2008/0281115 A1 40000 r+- !I- Hardness 30000 - + eon 00 ~ rn .§ 20000 - -I- r-±- ~ -r- 10000 - ..____, 0 I I I I I I I FHSO Cparaffin Beeswax Csoywax KLX EPKLX OHKLX BuoKLX Waxes Fig. SA 350000 ---.------------------------, Slope s 280000 ~ 210000 ff 140000 Er.i 70000 0-+~~~~~~==~~~~~~~~~~~~--~ FHSO Cparaffin Beeswax Csoywax KLX EPKLX OHKLX BuoKLX Waxes Fig.5B 1.00 ---.----------::::------------------, VTP ratio 0.80 0 i 0.60 c... ~ 0.40 0.20 00 00 -+-....1....-....1....-.----J-----L.---r-....L...-...J..........,----1...----1...~.J....__~----1,_----1,_--r--.L...__.I.........r----L..-----L........j FHSO Cparaffin Beeswax Csoywax KLX EPKLX OHKLX BuoKLX Waxes Fig.5C Patent Application Publication Nov. 13, 2008 Sheet 6 of 12 US 2008/0281115 A1 [ 001 c r- c og c=f- r 09 r- ~ I{ Ot 1:::1:1= I ~ ~ oz 0 r- [ 001 c r- 1-C::: og f- 09 ~0 Ot r- 1:::1:1= ---t I I- 0 oz ~ ~ d ~ 0 -~_... r- ca ~ 001 ] • r- og .......0 .~ r- ~ 09 Ot 0~ I oz ~ r- ~ 0 r- 001 r- r og 09 t- ~ 0~ I l---1 Ot 0 r- ~ ~ oz t- 0 I I I 8= 8= 8= 8= 8= = 1.0= ~ =C"':) C'\l= =.......... Patent Application Publication Nov. 13, 2008 Sheet 7 of 12 US 2008/0281115 A1 001 OB 09 ~0 ::::1 ov ~ ~ 06 0 001 OB 09 ~0 ov ~ I 0 06 t:r.:l d ~ 0 0 ·-~ 001] ~• I:... 0 -~ OB '"""' ~ 09 :c~ ov 0 I ~ 06 0 001 OB 09 0~ I ov 0 tiJ ~ 06 0 = = = = = =oooot' =C'? =C\.2 =........ mmj~ 'ado1s Patent Application Publication Nov. 13, 2008 Sheet 8 of 12 US 2008/0281115 A1 ----1 OOl 09 t- 09 ~ Ot CCI= t-----1 oc: ~ t- I---f 0 I ----1 OOl H.. 09 t- r-----1. 09 ~0 H Ot t- 0~ oc: t- --t ~ 1- 0 0 _...= u --...sl \Q I • r 001 0~ .~ ....... ~ r----t 09 f- 1--f 09 ~ 0~ Ot I ~ oc: f- 0 r- I t OOl 09 : f- i 09 I 0 Ot g::ti'J oc: 0 I I Patent Application Publication Nov. 13, 2008 Sheet 9 of 12 US 2008/0281115 A1 40000---,------------------------, ------------- KLX -- EPKLX 30000 ...... ~~_,..... -...... _...~·"'"\ -- OHKLX (------------------------- ---------------------------------------.... -·-·- BuoKLX \ ........... ______ -------------------- ... ~ 20000 {~------------------------- _, r:..:J- gs 10000 ~- --·- -·--- 0 r -· \ -·-·-. -----· ~----·~·r·,.-·-·-·----_J -60 -40 -20 0 20 40 60 80 100 Temperature, C Fig.7 Patent Application Publication Nov. 13, 2008 Sheet 10 of 12 US 2008/0281115 A1 70~----------------------------------------~ D Crystallization 60 ~ Melting ~ 0 50 ai ~ <t:! 0::: 40 C1J ........s <t:! 30 1-o C1J ~ sC1J E-< 20 10 Beeswax Cparaffin Csoywax FHSO KLX EPKLX OHKLX BuoKLX Wax Fig. SA 250 D Crystallization ~ Melting 200 s~ 150 ......., ---s .......; <t:! ::z::C1J 100 50 Beeswax Cparaffin Csoywax FHSO KLX EPKLX OHKLX BuoKLX Wax Fig.8B Patent Application Publication Nov. 13, 2008 Sheet 11 of 12 US 2008/0281115 A1 160.0 --r----------------------, Crystallization 120.0 s~ ---~s ""d- Cl) 00 cC 80.0 Cl) '(ij 0:::_... cC ::z::Cl) 40.0 FHSO-OHKLX • KLX-OHKLX ..• FHSO-BuoKLX )( KLX-BuoKLX 0.0 0 10 20 30 40 50 60 70 80 90 100 %of the modified wax Fig.9A 160.0 Melting s~ 120.0 ---~s ""d- Cl) 80.0 -e0 00 ::il _... cC ::z::Cl) 40.0 FHSO-OHKLX • KLX-OHKLX ..• FHSO-BuoKLX )( KLX-BuoKLX 0.0 0 20 40 60 80 100 %of the modified wax Fig.9B Patent Application Publication Nov. 13, 2008 Sheet 12 of 12 US 2008/0281115 A1 100 80 c...;. 0 v 60 ~ ct:l P:::; .s 40 ~ Q) :::;;! 20 --+-- FHSO-OHKLX - KLX-OHKLX ---&-- FHSD-BuoKLX ---*- KLX-BuoKLX 0 0 20 40 60 80 100 %of the modified wax Fig. lOA 100---.-------------------------, ~ 80 v ~ ~ 60 -+->-~ ~ 40 sct:l -+-> 00 ~ 20 --+-- FHSO-OHKLX - KLX-OHKLX ---&-- FHSD-BuoKLX ---*- KLX-BuoKLX 0~------~--------~------~------~------~ 0 20 40 60 80 100 %of the modified wax Fig. JOB US 2008/0281115 AI Nov. 13, 2008 1 CHEMICAL MODIFICATION OF PARTIALLY [0011] The introduction of hydroxyl (OH) group signifi­ HYDROGENATED VEGETABLE OIL TO cantly improves the cohesiveness of PHVO and increases its IMPROVE ITS FUNCTIONAL PROPERTIES melting range. While the hardness of the modified wax less­ TO REPLACE PETROLEUM WAXES ens, its hardness
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